Cistus albidus L.: History
View Latest Version
Please note this is an old version of this entry, which may differ significantly from the current revision.
Contributor:
Daniel Raus de Baviera
,
Antonio Ruiz-Canales
,
Enrique Barrajón-Catalán

Cistus albidus is one of the approximately 20 species of the Cistus genus. The genus’ name is derived from the ancient Greek term kistos. It is supposed that the name alludes to the woody capsule fruits. Evergreen in its Mediterranean homeland and between 50 and 250 centimeters tall, this shrub is called albidus, not because of the colour of its flowers, but because its leaves are finely covered with white hair (trichomes).

  • phytochemistry
  • pharmacology
  • polyphenols
  • terpenes
  • traditional uses

1. Botanical Characteristics

From the morphological point of view, C. albidus (Figure 1) is characterized by having five sepals, five pink to purple petals, up to 150 yellow stamens, pollen with a thin exine up to 1.4 μm thick, a long style that reaches or exceeds the stamens, and three cellular polysperm capsules. The hermaphroditic, actinomorphic, and hypogynous flowers, which appear from February to July, normally reach a diameter of four to six centimeters and develop individually or in umbels of usually five to seven [1]. The five sepals are ovate-lanceolate and hairy. The five petals, on the other hand, are delicate and slightly wrinkled. The flowers open in the morning and after a few hours the plant loses its petals. The flowers rarely last more than a day. A single adult bush can produce more than 1000 flowers per flowering period, depending on age [2].
The ovate-lanceolate leaves are arranged opposite each other and are usually 20–50 mm long and 8–30 mm wide; however, specimens with leaves exceeding 100 mm long and more than 50 mm wide have also been found by the authors. They are sessile, with a smooth margin, but may occasionally have a slightly wavy edge. Foliar veins are composed of three to five principal veins with a strong central vein. Adaxis veins are sunken, while veins on the abaxial surface are raised.
Plants 12 02988 g001
Figure 1. Typical Mediterranean landscape with a predominance of C. albidus, called jaral (left). Detail of flowers and leaves of C. albidus in spring (right). Images were captured by the authors.
Due to its morphological adaptation to an extremely dry climate within Mediterranean regions and a pronounced resistance to abiotic stress in general, C. albidus could be considered a malacophilous xerophyte. During dry periods, these plants reduce the growth of relatively long and wide hairy leaves until only short, narrow leaves remain. At the same time, the hairiness (trichomes) of the leaves of these plants is increased. In general, these processes significantly reduce respiration, which is an effective protection mechanism against dehydration [3][4].

Vegetative Development

C. albidus has developed mechanisms that allow it to withstand severe summer droughts. These mechanisms consist in part of a reduction in leaf area and angle [3], combined with an increase in root mass per leaf area and modification of stomatal conductance [5]. On the other hand, the link between tocopherols and jasmonates appears to be primarily responsible for the regulation of biotic and abiotic stress responses [6]. It was observed that, under water stress, C. albidus increases enzymes related to redox homeostasis, such as oxidized ascorbate reductase, glyoxalase, superoxide dismutase, and isoflavone reductase, which was related to a reduction in oxidative stress in C. albidus exposed to drought and the ability to recover quickly after re-irrigation [7]. The interaction of these mechanisms allows this species to resist the adverse Mediterranean climate conditions with only little photoinhibition [6].
Furthermore, C. albidus belongs to the nanophanerophytes (a subgroup of phanerophytes). These are plants whose overwintering buds are above the level of the snow cover. In contrast to the macrophanerophytes, they do not rise above the level of the surrounding vegetation. They are therefore partially sheltered from the wind. Due to this fact, a more than 2 m high specimen was discovered in the Valle y Carrascoy Regional Park in Murcia, surrounded by shrubs up to 3 m high.
The vegetative development of this species, which normally lives for about 14 years [8] and was found to reach 17 [9] or even 25 years [2], is characterized by two types of lateral shoots, dolichoblasts and brachyblasts. Dolichoblasts are long shoots with large leaves, which are produced when climatic conditions are benign (availability of water and absence of frost), which is usually between the end of February to May and from September to December. Brachyblasts are short shoots that develop throughout the year in the axils of leaves of dolichoblast shoots [10]. The fall of the leaves of this marcescent species is acropetic.
Sexual reproduction begins at about the age of one year. The flowers of this partially self-incompatible species [11] normally last around 12 h but may last up to two days on the plant, especially in rainy weather with high relative air humidity. This seems to be due to the fact that the apoidea, its main pollinators [11], do not fly in humid environmental conditions. It has been further shown that zeatin is the substance that modulates the speed of floral development, depending on the age of the plants [12].
Fruiting takes place from May to August. The capsules contain an average of about 80 seeds, with exceptions found by the authors from fewer than 10 seeds to more than 140, and generally mature from August to December [10][11], but in warmer regions such as the Spanish Levant, for example, the first capsules usually mature at the end of May. Mature capsules spread their seeds close to parent plants as they lack expansion mechanisms. Studies suggest that C. albidus seeds experience a combination of physical and physiological dormancy [13]. Although physical dormancy was broken and water was available, the seeds seemed able to partially control their dormancy and germination capacity [13]. Under optimal conditions, germination takes between five and ten days and is epigeal [14].
Like other plants typical of fire-prone regions, C. albidus is generally considered pyrophytic [15], especially since the heat generated by fire is thought to facilitate breaking physical dormancy due to the hard seed coat [8][16][17]; thus, it is one of the first shrubs to emerge after a fire. Development is therefore rapid within the first five years and then progressively slows down [8]. However, the scarification of the seeds, by soil particles, (through dragging by water flow) also softens the hard cover of the seeds, making them permeable to water [18], thus overcoming physical dormancy [18][19]. In addition, it is common to find this species along the edges of watercourses with temporary flows. This seems to be its dispersal strategy since forest fires do not facilitate the spatial expansion of this species. Very specific conditions must be met for the seeds to viably survive forest fires and also break the integument. For this reason, C. albidus could be considered an opportunistic pioneer plant.
Regarding the influence of the soil on the development of C. albidus, together with C. creticus, it is the only taxon of the purple-pink clade capable of growing independently in calcareous and acidic soils. However, C. albidus grows best on calcareous soils in Mediterranean climates [20][21]. Studies reported that no significant qualitative or quantitative differences were found in the polyphenolic profile between the cultivation of C. albidus in different types of soil [20][22], while the concentration of terpenes was influenced by soil conditions, showing lower yields in calcareous soils [23]. However, higher concentrations of polyphenols were not associated with lower soil fertility [24]. This suggests that the genetic influence of this species on the biosynthesis of phytochemicals may be stronger than the influence of soil parameters. This was confirmed by a recent study, where C. albidus exhibited a low translocation of Pb and Cd to aerial parts from heavy-metal-contaminated soil [25], making this species also suitable for plantations under problematic soil conditions.

2. Phytochemical Constituents

The main constituents of C. albidus-derived products belong to the groups of terpenes and polyphenols. Other organic compounds have also been detected. To date, more than 200 secondary metabolites have been reported in C. albidus samples. In this review, 153 terpenoids, including 31 monoterpenes, 109 sesquiterpenes, 9 diterpenes, and 3 tetraterpenes, and their respective derivatives were found. In addition, 58 polyphenols, including 19 phenolic acids, 17 flavonols, 11 flavanols, 3 ellagitannins, 3 anthocyanins, 2 flavones, 1 anthocyanidin, 1 flavanone, and 1 hydrolysable tannin, were found. Moreover, 8 fatty acids, 7 alkanes, and various other compounds were found in the literature and discussed in the present study.
The irregular presence of reported compounds–analyses were often very heterogeneous—is possibly due to seasonal variation and the analytical methods used. Secondary metabolites reported so far have been determined under a wide variety of conditions, making it sometimes difficult to compare among the studies. For example, some metabolites, such as punicalagin derivatives or some diterpenes, were only found in a small number of studies [20][26]. The results depend on multiple factors, such as the method of analysis, the season and hours of the day of collection, and the type of processing, among others, and some of these factors are not detailed in many studies. However, on the other hand, there are a number of compounds that practically all authors found in significant amounts, being thus characteristic of this species. These more common compounds will be highlighted in the following sections.
The various compound structures detected in C. albidus are described below, headed by the terpenes and paying particular attention to the essential oils (mono- and sesquiterpenes). Phenylpropanoids detected in essential oils are also briefly discussed. Furthermore, di- and tetraterpenes are described. The second large group of substances, polyphenols, are examined more closely, especially flavonols, flavanols, ellagitannins, and phenolic acids. The carbonyl compounds and alkanes found so far are then listed. Finally, proven phytohormones and various fatty acids are described. However, the latter is not part of the secondary metabolism but is included here for its supposed importance as a potential bioavailability enhancer.

2.1. Terpenes

2.1.1. Mono- and Sesquiterpenes from the Essential Oils

Terpenes, a very large but heterogeneous group of naturally occurring secondary metabolites in C. albidus, represent the group with the most compounds identified in this species. Among them, the most abundant were the sesquiterpenes; they were, in addition, the largest class of identified compounds in C. albidus. While monoterpenes were found to contribute, to a certain extent, together with aldehydes, to the characteristic odor of this species (they are among the main components of floral aromas), the sesquiterpenes play a signaling role in the defense mechanisms of this species, acting as herbivore repellents or through the attraction of predators. Diterpenes are also synthesized for defense purposes and serve as precursors for vitamins and hormones such as tocopherols and gibberellins. Finally, tetraterpenes contribute to the pigmentation of flowers and fruits, playing an essential role in the pollination and distribution of seeds. As an antioxidant, it protects C. albidus from oxidative stress caused by adverse growing conditions [5].
The ISO definition for essential oils is “Product obtained from a natural raw material of plant origin, by steam distillation, by mechanical processes from the epicarp of citrus fruits, or by dry distillation, after separation of the aqueous phase—if any—by physical processes” [27].
Essential oils from fresh aerial parts of C. albidus were generally obtained in low yields of 0.01–0.1% (w/w) [28][29][30] by steam distillation. The seeds, in particular, contain very small amounts of essential oil, sometimes insufficient to be analyzed, with a yield of less than 0.01% [30]. The concentration of terpenes depends fundamentally on soil conditions (the more calcareous, the lower the yield), climatic factors, and the season [23]. Analysis of seasonal variation in terpene composition shows strong interannual variability, with the highest emission rates in autumn and spring and the lowest in summer and winter, leading to maximum values of stored terpenes in autumn and winter, while the spring and summer values showed minimum levels [29]. Table 1 shows the list of the terpenoids identified in C. albidus samples, including information about their previously published pharmacological activity. The compounds most frequently found in the analyses of the extracted terpenes (w/w), and therefore representative of this species, whether in leaves, pollen, flowers, flowering tops, or stems, are α-zingiberene (7.4–20.7%), aromadendrene (1.0–10.6%), ar-curcumene (8.3–13.2%), and germacrene D (1.0–7.9%) [28][30][31][32][33][34][35]. Among the terpenes in leaves, flowering tops, and flowers, monoterpenes were only present in small quantities and sometimes only in traces, while sesquiterpenes were the most abundant [28][30][31].
Table 1. Identified terpenes in Cistus albidus. Table includes the structure for each compound along with the references in which it was identified and its pharmacological activity (including the references for this activity). 🌱: aerial parts, including leaves and twigs; ✿: flowering tops, flowers, petals, and sepals; 𐩕: pollen. n/a: reliable data are not available.
No Compound Structure/Class Presence in Analytical Reference Pharmacology
1 cis-α-Bergamotene polycyclic monoterpene hydrocarbon 🌱✿ [30][31][35] n/a
2 trans-α-Bergamotene 🌱 [29][30]
3 Borneol polycyclic
monoterpene
alcohol		 🌱 [34] blood brain barrier (BBB) permeability improvement,
intercellular tight junction (TJ) loosening [36]
4 Camphor oxygenated polycyclic monoterpene 🌱 [32] analgesic, antinociceptive [37];
antimicrobial,
antiviral [38];
anticancer [39];
antitussive [40];
skin penetration enhancer [41];
5 Carene polycyclic monoterpene
hydrocarbon		 🌱✿ [34] antiviral [42];
enhances bone mineralization [43];
anti-inflammatory [44];
6 Carvacrol monocyclic monoterpene alcohol 🌱✿ [31] antibacterial (64);
antifungal [45];
antioxidant [46];
anticancer [47];
anti-inflammatory, analgesic [48];
antiobesity [49];
hepatoprotective [50];
spasmolytic [51];
vasorelaxant [52];
7 β-Cyclocitral oxygenated monocyclic monoterpene 🌱 [35] n/a
8 p-Cymene monocyclic
monoterpene
hydrocarbon		 🌱 [31][32] anti-inflamatory, antinociceptive, antioxidant [53];
antidiabetic [54];
9 p-Cymenene monocyclic
monoterpene
hydrocarbon		 🌱✿ [32] n/a
10 Isobornyl formate oxygenated polycyclic monoterpene 🌱 [32] n/a
11 (D-)Limonene monocyclic monoterpene hydrocarbon 🌱✿ [29][30][31][32] anticancer, anticholesterol [55];
antidepressant [56];
12 Linalool acyclic monoterpene
alcohol		 🌱✿ [33][34] antibacterial, antifungal [57];
anxiolytic [58];
anticancer, antioxidant [59];
analgesic [60];
anti-inflammatory [61];
13 cis-linalool oxide oxygenated
heteromonocyclic
monoterpene		 [33] n/a
14 Myrcene acyclic monoterpene hydrocarbon 🌱 [31][33] analgesic,
antinociceptive [62];
15 Neryl acetate acyclic monoterpene hydrocarbon 🌱✿ [35] n/a
16 (E)-Ocimene acyclic monoterpene hydrocarbon 🌱✿ [31] anticancer [63];
anticonvulsant [64];
17 (Z)-β-Ocimene [31] anticancer [63];
antibacterial [65];
18 α-Phellandrene monocyclic
monoterpene
hydrocarbon		 🌱 [31] antifungal [66];
antidepressant [67];
anti-inflammatory,
antihyperalgesic [67][68],
analgesic, antinociceptive [68];
anticancer [69];
19 β-Phellandrene ✿ [31] n/a
20 α-Pinene polycyclic
monoterpene
hydrocarbon		 🌱 [29][31][33] antifungal, anti-inflammatory, antioxidant [70];
anticancer [71];
anti-Leishmania [72];
gastroprotective [73][74];
antibacterial [75];
antiviral [76];
neuroprotective [77];
21 β-Pinene 🌱✿ [29] anticancer [78];
antimicrobial [79];
gastroprotective [74];
neuroprotective [80];
22 Piperitone oxygenated monocyclic monoterpene 𐩕 [31] n/a
23 Sabinene polycyclic monoterpene hydrocarbon 🌱 [31] n/a
24 cis-Sabinene hydrate oxygenated polycyclic monoterpene [31]
25 Safranal oxygenated monocyclic monoterpene 🌱 [35] antioxidant [81];
antimicrobial [82];
anticonvulsant [83];
antidepressant, anxiolytic [84];
gastroprotective [85];
26 α-Terpinene monocyclic
monoterpene
hydrocarbon		 🌱 [31] antioxidant [86];
antimicrobial [87];
27 Δ-Terpinene 🌱✿ [34] n/a
28 γ-Terpinene ✿ [31] antimicrobial [87];
29 α-Terpineol monocyclic
monoterpene
alcohol		 ✿𐩕 [31][32][34][35][88] antioxidant, anticancer,
antinociceptive, anticonvulsant, sedative, antibronchitis, antihypertensive, vasorelaxant, cardioprotective [89];
30 4-Terpineol 🌱 [31][35] antimicrobial [90];
gastroprotective [91];
31 Thymol monocyclic
monoterpene
hydrocarbon		 🌱✿ [31][32] anti-inflammatory, antioxidant, antimicrobial, immunostimulatory, anticancer [92];
cardioprotective [93];
antihypertensive [52];
antihyperglycemic [94];
antinociceptive [95];
gastroprotective [96];
anxiolytic [97];
32 Abscisic acid oxygenated
monocyclic
sesquiterpene		 🌱 [98][99] antidiabetic [100];
antinociceptive [101];
33 α-Amorphene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32][35] n/a
34 Aromadendrene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [29][30][35] antimicrobial [102];
35 allo-Aromadendrene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [22][23][28][30][31][32][33][34][35]
36 allo-Aromadendrene epoxide oxygenated
polycyclic
sesquiterpene		 🌱 [35]
37 Bisabola-2,10-diene(1-9)oxide oxygenated
polycyclic sesquiterpene		 🌱 [35] n/a
38 β-Bisabolene monocyclic
sesquiterpene hydrocarbon		 [30] anticancer [103]
39 epi-α-Bisabolol monocyclic
sesquiterpene
alcohol		 🌱✿ [28][30][31][35] anti-inflammatory [104];
antimicrobial [105];
anticancer [106];
40 α-Bisabolol 🌱 [23][35] n/a
41 β-Bisabolol 🌱✿ [30] n/a
42 β-Bourbonene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [22][23][28][29][31][32][33][34][35] n/a
43 1,5-di-epi-Bourbonene (α or β) 🌱 [35]
44 Bulnesol polycyclic
sesquiterpene
alcohol		 🌱✿ [31] n/a
45 Cadalene polycyclic
sesquiterpene
hydrocarbon		 🌱 [35] n/a
46 Cadina-1,4-diene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [30][35] n/a
47 α-Cadinene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32][35] n/a
48 cis-γ-Cadinene 🌱✿𐩕 [31]
49 trans-γ-Cadinene 🌱 [28]
50 γ-Cadinene 🌱 [33][34][35]
51 δ-Cadinene 🌱✿𐩕 [23][28][30][31][32][34][35]
52 α-Cadinol polycycylic
sesquiterpene
alcohol		 🌱✿ [23][30][31][35] antifungal [107];
53 T-Cadinol [28][31][35][108] anticancer [109]
54 α-Calacorene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32][35] n/a
55 β-Calacorene [35]
56 Calamenene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32][35] anticancer [109];
57 Caryophylladienol I polycyclic
sesquiterpene
alcohol		 🌱 [35] n/a
58 Caryophylladienol II [35]  
59 β-Caryophyllene polycyclic
sesquiterpene
hydrocarbon		 🌱✿𐩕 [22][23][28][29][30][31][32][33][34][35] antioxidant, antimicrobial, antitumor, anticancer [110];
anti-inflammatory,
neuroprotective [111];
anxiolytic, antidepressant [112];
anticonvulsant [113];
analgesic [114];
60 β-Caryophyllene
epoxide		 oxygenated
polycyclic
sesquiterpene		 🌱 [23][28][30][31][35] anticancer, analgesic [114];
61 Caryophyllenol II polycyclic
sesquiterpene
alcohol		 🌱 [35] n/a
62 8,14-Cedranoxide oxygenated
sesquiterpene		 🌱 [28] n/a
63 α-Cedrene polycyclic
sesquiterpene
hydrocarbon		 🌱 [29] n/a
64 α-Copaene polycyclic
sesquiterpene
hydrocarbon		 🌱 [22][28][29][31][32][34][35] antioxidant, anticancer [115];
neuroprotective [116];
65 β-Copaene 🌱✿𐩕 [28][32][35]
66 α-Corocalene polycyclic
sesquiterpene hydrocarbon		 🌱 [35] n/a
67 α-Cubebene polycyclic
sesquiterpene hydrocarbon		 🌱✿ [22][31][35] antioxidant,
neuroprotective [117];
antimicrobial [118];
anti-inflammatory [119];
68 β-Cubebene 🌱 [22][28][31]  
69 Cubebol polycyclic
sesquiterpene
alcohol		 🌱 [35] n/a
70 4-epi-Cubebol [35]
71 1,10-di-epiCubenol polycyclic
sesquiterpene
alchohol		 🌱✿ [28][31][35] n/a
72 Cubenol 🌱 [35]
73 1-epi-Cubenol 🌱✿ [28][31][35]
74 ar-Curcumen-15-al oxygenated monocyclic sesquiterpene 🌱 [28][35] n/a
75 ar-Curcumene monocyclic
sesquiterpene hydrocarbon		 🌱✿ [22][23][28][29][30][31][32][33][34][35][108] n/a
76 β-Curcumene ✿ [30]  
77 γ-Curcumene 🌱✿ [30][31]  
78 Curcuphenol monocyclic
sesquiterpene
alcohol		 🌱✿ [30][35] anticancer [120];
79 Cyclosativene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [31] n/a
80 Dehydrosesquicineole oxygenated
polycyclic
sesquiterpene		 🌱 [35] n/a
81 Bicyclo-Elemene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32] n/a
82 β-Elemene monocyclic
sesquiterpene
hydrocarbon		 🌱 [30][35] anticancer, anti-inflammatory [121];
83 γ-Elemene 🌱 [30]
84 δ-Elemene 🌱✿ [30][31][32]
85 Elemol monocyclic
sesquiterpene
alcohol		 🌱 [23][30][31] n/a
86 β-Eudesma 4(15), 7 dien-1β-ol polycyclic
sesquiterpene
alcohol		 🌱 [35] n/a
87 α-Eudesmol 🌱 [28] neuroprotective [122];
88 β-Eudesmol 🌱✿ [28][30] anti-allergic,
anti-inflammatory [123];
anticancer [124];
89 γ-Eudesmol 🌱✿ [30][31] n/a
90 10-epi-γ-Eudesmol [30][31] n/a
91 Kunseaol monocyclic
sesquiterpene
alcohol		 🌱 [35] n/a
92 Bicyclo-Germacrene polycyclic
sesquiterpene
hydrocarbon		 🌱 [35] n/a
93 Germacrene B monocyclic
sesquiterpene
hydrocarbon		 🌱 [29][30]  
94 Germacrene D 🌱✿𐩕 [22][23][29][30][31][33][34][35] anticancer [125];
anti-inflammatory,
analgesic [126];
antioxidant [127];
95 Iso-Germacrene D 🌱 [35]  
96 β-Germacrenol monocyclic
sesquiterpene
alcohol		 🌱 [35] n/a
97 Globulol polycyclic
sesquiterpene
alcohol		 🌱✿ [28][30] n/a
98 α-Guaia-6,10(14)-diene-4β-ol polycyclic
sesquiterpene
alcohol		 🌱 [35] n/a
99 Guaiene polycyclic
sesquiterpene
hydrocarbon		 🌱 [28] n/a
100 Guaiol polycyclic
sesquiterpene
alcohol		 🌱✿ [30][31] n/a
101 α-Gurjunene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [29][31][33][34] n/a
102 β-Gurjunene [31]
103 β-Himachalene polycyclic
sesquiterpene
hydrocarbon		 ✿𐩕 [31] n/a
104 α-Humulene monocyclic
sesquiterpene
hydrocarbon		 🌱✿ [22][23][28][29][30][31][33][34][35] antitumor,
anti- inflammatory,
antimicrobial [128];
105 Iso-Calamendiol polycyclic
sesquiterpene
alcohol		 🌱 [35] n/a
106 Iso-Italicene polycyclic
sesquiterpene
hydrocarbon		 🌱 [28] n/a
107 Juniper camphor polycyclic
sesquiterpene
alcohol		 🌱✿ [31] n/a
108 Ledol polycyclic
sesquiterpene
alcohol		 🌱 [35][88] n/a
109 α-Longipinene polycyclic
sesquiterpene
hydrocarbon		 🌱 [28] n/a
110 cis-Muurola-4(14),5-diene polycyclic
sesquiterpene
hydrocarbon		 🌱✿ [31][35] n/a
111 α-Muurolene [22][30][31][32][34]  
112 γ-Muurolene [28][31][35]  
113 14-hydroxi-α-Muurolene polycyclic
sesquiterpene
alcohol		 🌱 [28] n/a
114 α-Muurolol 🌱✿ [31]
115 epi-α-Muurolol [30]
116 T-Muurolol [23][28][31][31][35]
117 E-Nerolidol acyclic
sesquiterpene
alcohol		 🌱✿ [30] antihyperlipidemic, anti-inflammatory, anti-uterine fibroids [129];
anticancer [130];
118 (E)-Nuciferol moncyclic
sesquiterpene
alcohol		 🌱 [35] n/a
119 β-Oplopenone oxygenated
polycyclic
sesquiterpene		 🌱 [35] n/a
120 Salvial-4(14)-en-1-one oxygenated
polycyclic
sesquiterpene		 🌱 [35] n/a
121 α-Santalene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32] n/a
122 cis-α-Santalol polycyclic
sesquiterpene
alcohol		 🌱 [28] antihyperglycemic,
antioxidant [131];
123 Selin-11-en-4-α-ol polycyclic
sesquiterpene
alcohol		 🌱 [88] anxiolytic,
sedative [132];
124 Selina-3,7(11)-diene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32] n/a
125 α-Selinene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32] n/a
126 β-Sesquiphellandrene monocyclic
sesquiterpene
hydrocarbon		 🌱✿ [23][29][31][35] anticancer [133];
antioxidant [134];
127 trans-Sesquisabinene
hydrate		 polycyclic
sesquiterpene
alcohol		 🌱 [30] n/a
128 Shyobunone oxygenated
monocyclic
sesquiterpene		 🌱 [22][35] neuroprotective,
acetyl-cholinesterase
inhibition [135];
129 6-epi-Shyobunone [35]
130 iso-Shyobunone [35]
131 Spathulenol polycyclic
sesquiterpene
alcohol		 🌱✿ [28][30][31][35] neuroprotective [136];
antibacterial, antioxidant,
anti-inflammatory,
anticancer [137];
132 Spathulenol isomer 🌱 [30]
133 ar-Turmerol monocyclic
sesquiterpene
alcohol		 🌱✿ [28][30] n/a
134 Valerianol polycyclic
sesquiterpene
alcohol		 🌱✿ [31] n/a
135 Viridiflorol polycyclic
sesquiterpene
alcohol		 🌱✿ [30][35] anti-arthritic,
analgesic, antinociceptive [138];
anticancaer [139];
antioxidant, antibacterial,
anti-inflammatory [140];
136 Xanthorrhizol monocyclic
sesquiterpene
alcohol		 🌱 [28][35] anticancer [141];
antimicrobial, antibacterial [142];
antihypolipidemic [143];
anti-inflammatory [144];
137 α-Ylangene polycyclic
sesquiterpene
hydrocarbon		 🌱 [32] n/a
138 β-Ylangene 🌱 [35]  
139 α-Zingiberene monocyclic
sesquiterpene
hydrocarbon		 🌱✿𐩕 [22][23][28][29][30][31][32][33][34][35] analgesic, neuroprotective [145];
anticancer [146];
anti-inflammatory [147];
140 Zingiberenol monocyclic
sesquiterpene
alcohol		 🌱 [35] n/a
141 15,16-Dinorlabd-8(20)-en-13-one oxygenated
diterpene		 🌱 [88] n/a
142 Geranyl-p-cymene monocyclic
diterpene
hydrocarbon		 🌱 [35] n/a
143 Geranyl α-terpinene monocyclic
diterpene
hydrocarbon		 🌱 [35] n/a
144 Geranyl linalool acyclic
diterpene
alcohol		 🌱 [35] n/a
145 Gibberellin oxygenated
polycyclic
diterpene		 🌱 [4] n/a
146 Manool polycyclic
diterpene
alcohol		 🌱 [88] antioxidant, anti-inflammatory [148]; anticancer [149];
antihypertensive [150];
cardioprotective [151];
147 Manoyl oxide polycyclic
oxygenated
diterpene		 🌱 [108] anticancer [152];
148 13-epi-Manoyl oxide [29][35][108]
149 Methyl Neoabietate oxygenated
polycyclic
diterpene		 🌱 [29] n/a
150 lutein oxygenated
polycyclic
tetraterpene		 🌱 [4] antioxidant, anti-inflammatory, neuroprotective [153];
anticancer [154];
hepatoprotective [155];
cardiopreotective [156];
151 neoxanthin oxygenated
polycyclic
tetraterpene		 🌱 [4] antihyperlipidemic [157];
152 zeaxanthin oxygenated
polycyclic
tetraterpene		 🌱 [4] n/a
The following quantities refer to the w/w of the extracted oil. Oxygenated sesquiterpenes ranged from 44.8% in aerial parts (twigs, leaves, flowers) [28] to 67.1% in leaves [31]. Hydrocarbon sesquiterpenes were found from 22.5% in flowers [31] to 48.6% in aerial parts including flowers [28]. Within representative sesquiterpenes in leaves, α-zingiberene is the most abundant and was extracted from 5.9% [31] to 14.8% [30], followed by α-bisabolol with values ranging from 1.9% [30] to 11.4% [28]. Further ar-curcumene was obtained from 8.3% [28] to 10.6% [30], and β-bourbonene showed a presence from a residual 0.1% [30] up to 8.7% [28].
The essential oil compositions of the aerial parts (stems and leaves) of C. albidus showed only quantitative differences. However, the flowers’ (petals’) essential oil has a different composition, with mainly α-zingiberene, α-cadinol, ar-curcumene, and δ-cadinene [30][31], while the composition of the isolated pollen contained α-zingiberene, δ-cadinene, and germacrene D within the most abundant compounds [31].
Since the analyzed samples come from different places with different climatic and soil conditions, were collected on different dates, and were sometimes analyzed by different methods, comparison of their compositions is only possible to a very limited extent. In addition to these limitations, it must also be taken into account that the species of the Cistus subgenus hybridize with each other, which may also have an impact on the composition of the synthesized compounds if species purity has not been ensured beforehand.

2.1.2. Phenylpropanoids from the Essential Oils

Phenylpropanoids are compounds that are built from an aromatic benzene ring and a chain of three carbon atoms and often have hydroxyl and methoxy groups on the aromatic ring. Many phenylpropanoids are natural substances that are formed in plants and microorganisms through the shikimate biosynthetic pathway, with phenylalanine and tyrosine as intermediate compounds [158]. In addition to terpenes, phenylpropanoids are a frequent component of essential oils and represent the majority of natural phenolic substances or their precursors. The phenolpropanoids identified so far in C. albidus are eugenol [31][35][159] and chavicol [32].

2.1.3. Diterpenes

As for the diterpenes present in C. albidus, these are not usually detected in most analyses, because they belong to the non-volatile terpenes. This is mainly because the analytical methods described are not suitable for detecting non-volatile substances and not because of the absence of these compounds. The diterpenes detected so far are geranyl linalool, geranyl α-terpinene, geranyl p-cymene and 13-epi-mannoyloxide [35], methyl neoabietate [29], 15,16-dinorlabd-8(20)-en-13-one, manool [88], and manoyl oxide [108]. The latter was found in the aerial parts, including the stems, unlike 15,16-dinorlabd-8(20)-en-13-one and manool, which were obtained only from the leaves.

2.1.4. Tetraterpenes

Tetraterpenes are vital for plant growth, protection against stress, and successful reproduction. So far, lutein, neoxanthin, and zeaxanthin have been identified in C. albidus [4].

2.2. Phenolic Compounds

Phenolic compounds are based on the phenol structure. In general, these compounds can be divided into seven subgroups: simple phenols, hydroxybenzoic acids, hydroxycinnamic acids, coumarins, flavonoids, lignans, and lignins [160]. The concentration of these phenolic substances in plant foods depends, in part, on the plant species, the climate, and the degree of maturity [161]. In the present work, the analytical focus of phenolic compounds lies on the group of hydroxybenzoic acids (basic structure C6-C1), hydroxycinnamic acids (basic structure C6-C3) (Figure 2), and flavonoids (basic structure C6-C3-C6) as they are the most frequent polyphenolic groups present in C. albidus samples (Figure 3).
Plants 12 02988 g005
Figure 2. Structures of hydroxybenzoic and hydroxycinnamic acids.
Plants 12 02988 g006
Figure 3. Basic structure of flavonoids with their three characteristic rings which are formed by different biosynthetic pathways. The B ring is derived from the shikimate pathway via phenylalanine.
In general terms, the polyphenolic composition of C. albidus, is very similar to that of other members of the Cistus subgenus, such as C. crispus and C. × incanus (hybrid of C. albidus × C. criticus) [20]. A semi-quantitative analysis of the composition of extracts from C. albidus, C. clusii, C. ladanifer, and C. salviifolius revealed small differences between them [159] and a series of substances that occur exclusively in C. albidus, namely caftaric acid, prunin, and 5-O-caffeoylquinic acid glucoside [162].

2.2.1. Flavonoids

Flavonoids contribute to overall fruit color and flavor in plants [160]. In the form of flavones, they are responsible for the yellow hues of the inner petals in the flowers and of the stamens and, in the form of anthocyanidins, for the purple-pink colored petals of C. albidus. Flavones often appear as co-pigments of anthocyanins. The interaction of both types of dye explains the simultaneous appearance of yellow and red in different flowers. The flavonoids found so far are flavonols, flavones, flavanols, and tannins (Figure 4).
Plants 12 02988 g007
Figure 4. Structure of flavonoids with their three characteristic rings.
Flavonols and flavones occur in C. albidus’ aerial parts as free algycones and glycosides. They are responsible for yellow color nuances and are usually tasteless. Flavonols are distinguished from flavones by the presence of a 3-hydroxyl group (Figure 4). Phenolic substances of the flavonol subclass are present in all plant organs of C. albidus. Characteristic representatives of these compounds in C. albidus are kaempferol, quercetin, myricetin, myricitrin (myricetin-3-O-rhamnoside), and quercitrin (quercetin-3-O-rhamnoside) [20]. High contents of myricetin glycoside (7 mg/g dry weight) were detected in C. albidus aerial parts, with myricetin-3-O-rhamnoside being the primary derivative of myricetin with 83% of total myricetin composition, followed by quercetin glycoside (2 mg/g dry weight), with quercetin-3-O-rhamnoside being the most abundant derivative of quercetin, constituting 80% of the total quercetin composition [26]. The only flavones detected so far are diglycosylated apigenin [20] and the isoflavone glycitin 6″-O-malonate [162].
Flavanols are found predominantly in the leaves of C. albidus and contribute particularly to the astringent taste of extracts. Compounds belonging to this subclass have two asymmetrically substituted carbon atoms and can therefore exist as diastereomeric 5,7,3-,4-tetrahydroxyflavanols, catechin and epicatechin. A third hydroxyl group on ring B also results in 5,7,3,4,5-pentahydroxyflavanol gallocatechin, or correspondingly epigallocatechin (Figure 4). Among the polymeric flavanols, the most relevant compounds in C. albidus are prodelphinidins such as (epi-)gallocatechins. Procyanidins are other representative flavanols contained in C. albidus leaves. Within these oligomeric compounds, (epi-)catechins are most common in C. albidus aerial parts [20]. However, combinations of prodelphinidins and procyanidins have also been detected. So far, the following flavan-3-ol compounds have been found: (+)-catechin, (−)-epicatechin, (−)-(epi)gallocatechin, (−)-(epi)gallocatechin-(epi)catechin dimer, (−)-(epi)gallocatechin, and (−)-(epi)gallocatechin-(epi)gallocatein dimer [20][163].
Tannins are water-soluble, slightly acidic oligomers of polyphenols. They are able to form water-insoluble complexes with protein molecules. In the past, this property of C. albidus was used to tan animal skin in leather production [164]. Based on the chemical structure of the monomeric building blocks, tannins present in C. albidus could be divided into two groups, the condensed and the hydrolyzable tannins.
The first group includes the proanthocyanidins (flavanols) already described, which are also known as condensed tannins. They consist of polymerized flavonoid phenols, such as catechins, epicatechin, anthocyanins, and so on. They are correspondingly polymers whose monomeric units consist of phenolic flavans, mostly catechin (flavan-3-ol).
The second group represents hydrolyzable tannins, which are hydrolyzed by the action of acids. These compounds exist as various polyhydroxy compounds, for example as sugar esterified with a phenolic acid [160]. Within this group, hexahydroxydiphenoyl-D-glucose (HHDP-Glc) was detected in C. albidus [20]. When the phenolic acid is gallic acid, the compound is called gallotannin. If, on the other hand, esterification with hexahydroxydiphenic acid occurs, this compound is called ellagitannin. Ellagitannins were not found in C. albidus aerial parts, except for a residual presence of glucogallin, pedunculagin, and punicalagin gallate [20][26].

2.2.2. Phenolic Acids

Phenolic acids are understood as the hydroxylated derivatives of benzoic acids (hydroxybenzoic acids) and cinnamic acids (hydroxycinnamic acids). Their highest concentration in plants is found in the outer leaves. In C. albidus aerial parts, glucogallin [20][26] and gallic acid [20][165] were found. Within the category of phenolic acid derivatives, 5-O-caffeoyl quinic acid glucoside, caffeoylquinic glycoside [162], and uralenneoside and rhamnoside of hydroxyferulic acid [20] have also been detected.

2.3. Carbonylic Compounds

Aldehydes are odoriferous aromatic substances in plants. These often arise from substances containing linolenic acid during harvesting, crushing, or preparation [166]. The aliphatic aldehydes, octanal [31], nonanal, and decanal [31][35], were exclusively identified in pollen and may be responsible for the typical sweet smell of the flowers [167]. On the other hand, tetradecanal, undecanal, and dodecanal were present in the aerial parts [35]. These compounds may contribute to the typical sweetish odor of C. albidus with its undertone of oranges, lemons, and roses [167][168].

2.4. Phytohormones and Vitamin E

Tocopherols and tocotrienols are also present in leaves and seeds. More than 75% of the vitamin E present in the seeds was in the form of α-tocopherol, followed by α-tocotrienol and γ-tocopherol [4][13][99], which is the immediate precursor of α-tocopherol. Phytohormone and vitamin studies further revealed the presence of the jasmonates 12-oxo-phytodienoic acid (OPDA), jasmonic acid (JA), and jasmonoyl-isoleucine (JA-Ile) and plastochormanol-8 [6], carotenoids, and abscisic acid, with α-tocopherol being the most abundant [2]. A negative correlation was revealed between vitamin E and OPDA accumulation in C. albidus under winter conditions, while a positive correlation was found between JA and α-tocopherol [6]. A significant positive correlation was also detected between hydration and total leaf chlorophylls due to the protection mechanism of tocopherols from the photosynthetic apparatus. Therefore, higher levels of α-tocopherol were observed under abiotic stress conditions and when the leaves showed an orientation more perpendicular to the solar rays [2][3][6][169].
Drought stress can induce an increase in the concentrations of abscisic acid and H2O2 in the leaves, inducing an increase in ascorbic acid, maintaining and even decreasing the oxidative state of ascorbate, thus protecting plants from oxidative damage [5][170]. In addition, cytokinins that act as nitric oxide scavengers and are involved in the modulation of the abscisic acid response have been reported [4].
C. albidus seeds obtained from mature plants showed higher concentrations of α-tocopherol, JA, and salicylic acid than those obtained from younger plants. Auxin (indole-3-acetic acid) content was also significantly higher in seeds from older plants. Gibberellic acid GA4 and its precursor GA24 were also found in seeds [2]. No differences were detected between the concentration of cytokinins in seeds from older and younger plants, except for zeatin, which was significantly higher in seeds from older plants. Zeatin was the main form of cytokinin found in the seeds of C. albidus [2].

2.5. Alkanes

Among the volatile compounds isolated from aerial parts of C. albidus, tricosan [35], tetracosan [29], pentacosan [23], octacosan [29], and docosan [23][29] were found. n-Tridecane was present in petals, and n-tetradecane was identified in both petals and pollen, while n-hexadecane was detected only in pollen, and n-pentadecane was found in leaves [23][29][35].

2.6. Other Compounds: Fatty and Carboxylic Acids

Although fatty acids are products of the primary metabolism, they are described here for the role they may play in the bioavailability of pharmacologically active compounds, as described below. Among the fatty acids found in the aerial parts of C. albidus are tetradecanoic, primaric and pentadecanoic acid [29], nonanoic acid [88], palmitic acid [35], and butanoic acid [31]. The fatty acid composition of the seeds showed significantly higher levels of polyunsaturated fatty acids as well as very-long-chain saturated fatty acids for older plants due to their higher levels of linoleic acid [2]. In addition, the carboxylic acids methacrylic acid [88] and quinic acid [159][162] were identified.

3. Preparation Methods of the C. albidus Extracts

Studies of the pharmacological properties of traditional medicines based on C. albidus preparations are related to the presence of terpenoids and polyphenols. In order to understand the use that has been given to C. albidus traditionally, it is necessary to first review the preparation methods used in popular medicine of this plant due to their influence on the pharmacological effect. 6.1. Traditional Preparations For the different applications, traditionally, only the aerial parts of C. albidus were harvested, mainly the leaves, but also flowers, flower buds, and to a lesser extent stems. The traditional preparation of C. albidus varies from an infusion to a prolonged decoction, while the dose usually used is around 3 g per 100 mL of water, taking a cup (150 mL) two or three times a day [171]. Within traditional preparations, decoction is the most used technique. It consists of boiling the plant material for a certain period of time and letting it rest afterwards. This method is primarily suitable for thermostable and water-soluble phytochemicals. During decoction, several compounds undergo chemical modifications. For example, catechins undergo epimerization, which is a change in their configuration relative to one of their stereogenic centres. Epimers, specifically epicatechins and epigallocatechins, have been shown to have important health benefits. It has been found that this epimerization occurs more readily in water with alkaline pH values than in purified water [172]. In addition, it has been shown that at temperatures greater than 98ºC, epimerization occurs faster than its degradation [173], so it can be deduced that the traditional preparation of C. albidus is the most effective way to extract catechins and their epimers. However, for green tea, the levels of epicatechin, epicatechin gallate, epigallocatechin, and epigallocatechin gallate were reported to increase only during the first 3 to 5 min of preparation (infusion at 85ºC), and the proportion of these flavonoids decreased as time increased. In contrast, another study found that levels of catechin, gallocatechin, and gallocatechin gallate increased continuously with the length of preparation time [174]. Taking these results into account, the pharmacological activities referred to in traditional use could be optimized by limiting the decoction time. Nonetheless, thermolabile compounds are lost in the decoction process. As a result, monoterpenes should not be contained in the resulting extract. Sesquiterpenes, however, would not be affected by extracting temperatures around 100 degrees but by low solubility in water due to their lipophilic character. It can therefore be assumed that terpenes play a minor role in the traditional decoction of plant material. On the other side, probably in order to use the entire compound spectrum of the plant, based on both terpenes and polyphenols, the dried and crushed leaves sometimes were used directly (orally) [175][176][177][178][179]. This usage ensures that the resulting medicine is rich in polyphenols terpenes and other volatiles. However, a loss of several terpenes and oxidative reactions could be induced by the drying process, as reported for other species as Cannabis sativa [180][181].

4. Therapeutical Uses

4.1. Traditional Uses

Plant resources have always been an integral part of human society throughout history. Until the middle of the last century, traditional medicines provided an alternative and inexpensive source of primary health care for the rural population. However, with access to synthetic drugs, a large number of medicinal plants became obsolete, the memory of which in the population, after only two generations, is being lost. One of these medicinal plants is C. albidus, which has been used in traditional folk medicine for a variety of illnesses [171][182][183][184], especially for the treatment of fever, diarrhea and other gastrointestinal illnesses [185], skin diseases, rheumatism, and various inflammatory diseases [165]. For the sake of completeness, it is mentioned here that C. albidus has also been used as a tanning agent [164], as an insect repellent, and as a substitute for tobacco, highly appreciated, moreover, for its hypotensive effect [31][184][186]. The decoction of leaves was traditionally used in the Spanish Levant as a tranquilizer, in the Baixa Plana as a sedative [171], and as a remedy against Parkinson’s symptoms in Mallorca [187][188]. To relieve toothache, mouthwashes were made with a decoction of its leaves and flowers. A sip of the resulting liquid, once cold, was kept in the mouth for some time [179][189][190][191]. In addition, the decoction of the aerial parts was used as an external antiseptic, for wounds and skin infections [190][191][192][193]. In the Spanish Basque Country, several uses were reported. For example, decoction was applied for the treatment of ulcers and for the treatment of gangrene, and fresh leaves were used directly on the wound for disinfection [194]. In the Mediterranean region, the decoction of the aerial parts (leaves, stems, and flowers) has been used to regulate blood pressure [195][196]. It has also been a frequent remedy for hemorrhoids and to treat bruises and varicose veins [187]. The decoction of flowers and leaves has also been popularly used as an analgesic for oral infections [293 and for hepatoprotection in Granada and Mallorca [187][195]. The decoction of the fresh aerial parts, including the flowers, was used as a remedy against colds and flu infections, and against bronchitis [175][187][196] and whooping cough [171]. In the Spanish peninsula, C. albidus decoction has also been used as a remedy for osteoarthritis in the province of Jaen [179] and for rheumatism in the Valencian community and the Province of Jaen [189][197]. In addition, it was used as an external antiseptic for wound healing and skin infections in the provinces of Castellon, Mallorca, and Almería [171][187][190], and in Morocco [176][178]. In Sardinia (Italy), a traditional use is reported in poultices and ointments, which were applied directly to the wound [198]. In cases of gastrointestinal infections, in Almería (Spain), an infusion of dried leaves was prepared to reduce abdominal pain [190][195]. Against colic, in Castilla-La Mancha and Murcia (Spain) an infusion of young and tender shoots was administered, but it was also supplied by oral ingestion of the powder of dry leaves for treatment [175]. The dried leaf powder also served as an antidiarrheal in Jaen [179]. Infusions of fresh flowers and leaves have been used as an antiseptic for the urinary tract in Murcia [199] and also as an anti-inflammatory for orchitis in Valencia [200].

This entry is adapted from the peer-reviewed paper 10.3390/plants12162988

References

  1. Guzmán, B.; Vargas, P. Long-Distance Colonization of the Western Mediterranean by Cistus ladanifer (Cistaceae) despite the Absence of Special Dispersal Mechanisms. J. Biogeogr. 2009, 36, 954–968.
  2. Müller, M.; Siles, L.; Cela, J.; Munné-Bosch, S. Perennially Young: Seed Production and Quality in Controlled and Natural Populations of Cistus albidus Reveal Compensatory Mechanisms That Prevent Senescence in Terms of Seed Yield and Viability. J. Exp. Bot. 2014, 65, 287–297.
  3. Pérez-Llorca, M.; Casadesús, A.; Müller, M.; Munné-Bosch, S. Leaf Orientation as Part of the Leaf Developmental Program in the Semi-Deciduous Shrub, Cistus albidus L.: Diurnal, Positional, and Photoprotective Effects During Winter. Front. Plant Sci. 2019, 10, 767.
  4. Pérez-Llorca, M.; Casadesús, A.; Munné-Bosch, S.; Müller, M. Contrasting Patterns of Hormonal and Photoprotective Isoprenoids in Response to Stress in Cistus albidus during a Mediterranean Winter. Planta 2019, 250, 1409–1422.
  5. Munné-Bosch, S.; Jubany-Marí, T.; Alegre, L. Enhanced Photo- and Antioxidative Protection, and Hydrogen Peroxide Accumulation in Drought-Stressed Cistus clusii and Cistus albidus Plants. Tree Physiol. 2003, 23, 1–12.
  6. Casadesús, A.; Bouchikh, R.; Pérez-Llorca, M.; Munné-Bosch, S. Linking Jasmonates with Vitamin E Accumulation in Plants: A Case Study in the Mediterranean Shrub Cistus albidus L. Planta 2021, 253, 36.
  7. Brossa, R.; Pintó-Marijuan, M.; Francisco, R.; López-Carbonell, M.; Chaves, M.M.; Alegre, L. Redox Proteomics and Physiological Responses in Cistus albidus Shrubs Subjected to Long-Term Summer Drought Followed by Recovery. Planta 2015, 241, 803–822.
  8. Roy, J.; Sonie, L. Germination and Population Dynamics of Cistus Species in Relation to Fire. J. Appl. Ecol. 1992, 29, 647.
  9. Casadesús, A.; Bouchikh, R.; Munné-Bosch, S. Contrasting Seasonal Abiotic Stress and Herbivory Incidence in Cistus albidus L. Plants Growing in Their Natural Habitat on a Mediterranean Mountain. J. Arid Environ. 2022, 206, 104842.
  10. Cabezudo, B.; Pérez Latorre, A.V.; Navarro, T.; Nieto Caldera, J.M. Estudios Fenomorfológicos En La Vegetación Del Sur de España. II. Alcornocales Mesomediterráneos. (Montes de Málaga, Málaga). Acta Bot. Malacit. 1993, 18, 179–188.
  11. Blasco, S.; Mateu, I. Flowering and Fruiting Phenology and Breeding System of Cistus albidus L. Acta Bot. Gallica 1995, 142, 245–251.
  12. Hernández, I.; Miret, J.A.; Van Der Kelen, K.; Rombaut, D.; Van Breusegem, F.; Munné-Bosch, S. Zeatin Modulates Flower Bud Development and Tocopherol Levels in Cistus albidus (L.) Plants as They Age. Plant Biol. 2015, 17, 90–96.
  13. Siles, L.; Müller, M.; Cela, J.; Hernández, I.; Alegre, L.; Munné-Bosch, S. Marked Differences in Seed Dormancy in Two Populations of the Mediterranean Shrub, Cistus albidus L. Plant Ecol. Divers. 2017, 10, 231–240.
  14. Rizzotto, M. Ricerche tassonomiche e corologiche sulle Cistaceae. 1: Il genere Cistus L. in Italia. Webbia 1979, 33, 343–378.
  15. Robles, C.; Dutoit, T.; Bonin, G. Inhibition Mechanisms and Successional Processes: A Case Study of Cistus albidus L. in Provence. Ecosyst. Sustain. Dev. 1998, 1, 437–446.
  16. Thanos, A.C.; Geroghiou, K.; Kadis, C.; Pantazi, C. Cistaceae: A plant family with hard seeds. Isr. J. Bot. 1993, 41, 251–263.
  17. Trabaud, L.; Oustric, J. Heat Requirements for Seed Germination of Three Cistus Species in the Garrigue of Southern France. Flora 1989, 183, 321–325.
  18. Trabaud, L.; Renard, P. Do light and litter influence the recruitment of cistus spp. Stands? Isr. J. Plant Sci. 1999, 47, 1–9.
  19. Baskin, J.M.; Baskin, C.C. A Classification System for Seed Dormancy. Seed Sci. Res. 2004, 14, 1–16.
  20. Barrajón-Catalán, E.; Fernández-Arroyo, S.; Roldán, C.; Guillén, E.; Saura, D.; Segura-Carretero, A.; Micol, V. A Systematic Study of the Polyphenolic Composition of Aqueous Extracts Deriving from Several Cistus Genus Species: Evolutionary Relationship: Polyphenolic Characterization of Cistus Aqueous Extracts. Phytochem. Anal. 2011, 22, 303–312.
  21. Polunin, O.; Schauer, T.; Everard, B. Pflanzen Europas; BLV-Bestimmungsbuch; BLV(-Verl. Ges.): München, Germany, 1971; ISBN 978-3-405-10929-5.
  22. Ormeño, E.; Baldy, V.; Ballini, C.; Fernandez, C. Production and Diversity of Volatile Terpenes from Plants on Calcareous and Siliceous Soils: Effect of Soil Nutrients. J. Chem. Ecol. 2008, 34, 1219–1229.
  23. Robles, C.; Garzino, S. Essential Oil Composition of Cistus albidus Leaves. Phytochemistry 1998, 48, 1341–1345.
  24. Castells, E.; Peñuelas, J. Is There a Feedback between N Availability in Siliceous and Calcareous Soils and Cistus albidus Leaf Chemical Composition? Oecologia 2003, 136, 183–192.
  25. El Mamoun, I.; Mouna, F.; Mohammed, A.; Najib, B.; Zine-El Abidine, T.; Abdelkarim, G.; Didier, B.; Laurent, L.; Abdelaziz, S. Zinc, Lead, and Cadmium Tolerance and Accumulation in Cistus libanotis, Cistus albidus and Cistus salviifolius: Perspectives on Phytoremediation. Remediat. J. 2020, 30, 73–80.
  26. Lukas, B.; Jovanovic, D.; Schmiderer, C.; Kostas, S.; Kanellis, A.; Gómez Navarro, J.; Aytaç, Z.; Koç, A.; Sözen, E.; Novak, J. Intraspecific Genetic Diversity of Cistus creticus L. and Evolutionary Relationships to Cistus albidus L. (Cistaceae): Meeting of the Generations? Plants 2021, 10, 1619.
  27. ISO Standard No. 9235:2013; International Organization for Standardization Aromatic Natural Raw Materials. ISO: Geneva, Switzerland, 2013.
  28. Bechlaghem, K.; Allali, H.; Benmehdi, H.; Aissaoui, N.; Flamini, G. Chemical Analysis of the Essential Oils of Three Cistus Species Growing in North- West of Algeria. Agric. Conspec. Sci. 2019, 84, 283–293.
  29. Llusià, J.; Peñuelas, J.; Ogaya, R.; Alessio, G. Annual and Seasonal Changes in Foliar Terpene Content and Emission Rates in Cistus albidus L. Submitted to Soil Drought in Prades Forest (Catalonia, NE Spain). Acta Physiol. Plant. 2010, 32, 387–394.
  30. Palá-Paúl, J.; Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Sanz, J. Seasonal Variation in Chemical Composition of Cistus albidus L. from Spain. J. Essent. Oil Res. 2005, 17, 19–22.
  31. Maccioni, S.; Baldini, R.; Cioni, P.L.; Tebano, M.; Flamini, G. In Vivo Volatiles Emission and Essential Oils from Different Organs and Pollen Of Cistus albidus from Caprione (Eastern Liguria, Italy). Flavour Fragr. J. 2007, 22, 61–65.
  32. Morales-Soto, A.; Oruna-Concha, M.J.; Elmore, J.S.; Barrajón-Catalán, E.; Micol, V.; Roldán, C.; Segura-Carretero, A. Volatile Profile of Spanish Cistus Plants as Sources of Antimicrobials for Industrial Applications. Ind. Crops Prod. 2015, 74, 425–433.
  33. Ormeño, E.; Mévy, J.P.; Vila, B.; Bousquet-Mélou, A.; Greff, S.; Bonin, G.; Fernandez, C. Water Deficit Stress Induces Different Monoterpene and Sesquiterpene Emission Changes in Mediterranean Species. Relationship between Terpene Emissions and Plant Water Potential. Chemosphere 2007, 67, 276–284.
  34. Ormeño, E.; Bousquet-Mélou, A.; Mévy, J.-P.; Greff, S.; Robles, C.; Bonin, G.; Fernandez, C. Effect of Intraspecific Competition and Substrate Type on Terpene Emissions from Some Mediterranean Plant Species. J. Chem. Ecol. 2007, 33, 277–286.
  35. Paolini, J.; Tomi, P.; Bernardini, A.-F.; Bradesi, P.; Casanova, J.; Kaloustian, J. Detailed Analysis of the Essential Oil from Cistus albidus L. by Combination of GC/RI, GC/MS and 13C-NMR Spectroscopy. Nat. Prod. Res. 2008, 22, 1270–1278.
  36. Gao, H.; Gao, X. Brain Targeted Drug Delivery Systems: A Focus on Nanotechnology and and Nanoparticulates; Academic Press: London, UK, 2019; ISBN 978-0-12-814002-4.
  37. Xu, H.; Blair, N.T.; Clapham, D.E. Camphor Activates and Strongly Desensitizes the Transient Receptor Potential Vanilloid Subtype 1 Channel in a Vanilloid-Independent Mechanism. J. Neurosci. Off. J. Soc. Neurosci. 2005, 25, 8924–8937.
  38. Chen, W.; Vermaak, I.; Viljoen, A. Camphor—A Fumigant during the Black Death and a Coveted Fragrant Wood in Ancient Egypt and Babylon—A Review. Molecules 2013, 18, 5434–5454.
  39. Banerjee, S.; Welsch, C.W.; Rao, A.R. Modulatory Influence of Camphor on the Activities of Hepatic Carcinogen Metabolizing Enzymes and the Levels of Hepatic and Extrahepatic Reduced Glutathione in Mice. Cancer Lett. 1995, 88, 163–169.
  40. Laude, E.A.; Morice, A.H.; Grattan, T.J. The Antitussive Effects of Menthol, Camphor and Cineole in Conscious Guinea-Pigs. Pulm. Pharmacol. 1994, 7, 179–184.
  41. Liu, H.; Zhou, Y.; Sun, Y.; Sheng, X.; Zhang, J.; Zhang, Z.; Ding, J. Effect of Menthol and Camphor on Permeation of Compound Diphenhydramine Cream in Vitro. Cent South Pharm. 2011, 9, 97–101.
  42. Patra, J.K.; Das, G.; Bose, S.; Banerjee, S.; Vishnuprasad, C.N.; Pilar Rodriguez-Torres, M.; Shin, H. Star Anise (Illicium verum): Chemical Compounds, Antiviral Properties, and Clinical Relevance. Phytother. Res. 2020, 34, 1248–1267.
  43. Jeong, J.-G.; Kim, Y.S.; Min, Y.K.; Kim, S.H. Low Concentration of 3-Carene Stimulates the Differentiation of Mouse Osteoblastic MC3T3-E1 Subclone 4 Cells. Phytother. Res. 2008, 22, 18–22.
  44. Gil, M.L.; Jimenez, J.; Ocete, M.A.; Zarzuelo, A.; Cabo, M.M. Comparative Study of Different Essential Oils of Bupleurum gibraltaricum Lamarck. Pharmazie 1989, 44, 284–287.
  45. Pina-Vaz, C.; Gonçalves Rodrigues, A.; Pinto, E.; Costa-de-Oliveira, S.; Tavares, C.; Salgueiro, L.; Cavaleiro, C.; Gonçalves, M.J.; Martinez-de-Oliveira, J. Antifungal Activity of Thymus Oils and Their Major Compounds. J. Eur. Acad. Dermatol. Venereol. 2004, 18, 73–78.
  46. Aeschbach, R.; Löliger, J.; Scott, B.C.; Murcia, A.; Butler, J.; Halliwell, B.; Aruoma, O.I. Antioxidant Actions of Thymol, Carvacrol, 6-Gingerol, Zingerone and Hydroxytyrosol. Food Chem. Toxicol. 1994, 32, 31–36.
  47. Jayakumar, S.; Madankumar, A.; Asokkumar, S.; Raghunandhakumar, S.; Gokula dhas, K.; Kamaraj, S.; Divya, M.G.J.; Devaki, T. Potential Preventive Effect of Carvacrol against Diethylnitrosamine-Induced Hepatocellular Carcinoma in Rats. Mol. Cell. Biochem. 2012, 360, 51–60.
  48. Hotta, M.; Nakata, R.; Katsukawa, M.; Hori, K.; Takahashi, S.; Inoue, H. Carvacrol, a Component of Thyme Oil, Activates PPAR alpha and Gamma and Suppresses COX-2 Expression. J. Lipid Res. 2010, 51, 132–139.
  49. Cho, S.; Choi, Y.; Park, S.; Park, T. Carvacrol Prevents Diet-Induced Obesity by Modulating Gene Expressions Involved in Adipogenesis and Inflammation in Mice Fed with High-Fat Diet. J. Nutr. Biochem. 2012, 23, 192–201.
  50. Decker, K.; Keppler, D. Galactosamine Induced Liver Injury. Prog. Liver Dis. 1972, 4, 183–199.
  51. Boskabady, M.H.; Jandaghi, P. Relaxant Effects of Carvacrol on Guinea Pig Tracheal Chains and Its Possible Mechanisms. Pharmazie 2003, 58, 661–663.
  52. Peixoto-Neves, D.; Silva-Alves, K.S.; Gomes, M.D.M.; Lima, F.C.; Lahlou, S.; Magalhães, P.J.C.; Ceccatto, V.M.; Coelho-de-Souza, A.N.; Leal-Cardoso, J.H. Vasorelaxant Effects of the Monoterpenic Phenol Isomers, Carvacrol and Thymol, on Rat Isolated Aorta. Fundam. Clin. Pharmacol. 2010, 24, 341–350.
  53. Quintans-Júnior, L.; Moreira, J.C.F.; Pasquali, M.A.B.; Rabie, S.M.S.; Pires, A.S.; Schröder, R.; Rabelo, T.K.; Santos, J.P.A.; Lima, P.S.S.; Cavalcanti, S.C.H.; et al. Antinociceptive Activity and Redox Profile of the Monoterpenes (+)-Camphene, p -Cymene, and Geranyl Acetate in Experimental Models. ISRN Toxicol. 2013, 2013, 459530.
  54. Arabloei Sani, M.; Yaghmaei, P.; Hajebrahimi, Z.; Hayati Roodbari, N. Therapeutic Effect of P-Cymene on Lipid Profile, Liver Enzyme, and Akt/Mtor Pathway in Streptozotocin-Induced Diabetes Mellitus in Wistar Rats. J. Obes. 2022, 1–12.
  55. Sun, J. D-Limonene: Safety and Clinical Applications. Altern. Med. Rev. J. Clin. Ther. 2007, 12, 259–264.
  56. Lorigooini, Z.; Boroujeni, S.N.; Sayyadi-Shahraki, M.; Rahimi-Madiseh, M.; Bijad, E.; Amini-Khoei, H. Limonene through Attenuation of Neuroinflammation and Nitrite Level Exerts Antidepressant-Like Effect on Mouse Model of Maternal Separation Stress. Behav. Neurol. 2021, 2021, 8817309.
  57. Pattnaik, S.; Subramanyam, V.R.; Bapaji, M.; Kole, C.R. Antibacterial and Antifungal Activity of Aromatic Constituents of Essential Oils. Microbios 1997, 89, 39–46.
  58. Linck, V.M.; da Silva, A.L.; Figueiró, M.; Caramão, E.B.; Moreno, P.R.H.; Elisabetsky, E. Effects of Inhaled Linalool in Anxiety, Social Interaction and Aggressive Behavior in Mice. Phytomedicine 2010, 17, 679–683.
  59. Jana, S.; Patra, K.; Sarkar, S.; Jana, J.; Mukherjee, G.; Bhattacharjee, S.; Mandal, D.P. Antitumorigenic Potential of Linalool Is Accompanied by Modulation of Oxidative Stress: An in Vivo Study in Sarcoma-180 Solid Tumor Model. Nutr. Cancer 2014, 66, 835–848.
  60. Sugawara, Y.; Hara, C.; Aoki, T.; Sugimoto, N.; Masujima, T. Odor Distinctiveness between Enantiomers of Linalool: Difference in Perception and Responses Elicited by Sensory Test and Forehead Surface Potential Wave Measurement. Chem. Senses 2000, 25, 77–84.
  61. Peana, A.T.; D’Aquila, P.S.; Panin, F.; Serra, G.; Pippia, P.; Moretti, M.D.L. Anti-Inflammatory Activity of Linalool and Linalyl Acetate Constituents of Essential Oils. Phytomedicine 2002, 9, 721–726.
  62. Jansen, C.; Shimoda, L.M.N.; Kawakami, J.K.; Ang, L.; Bacani, A.J.; Baker, J.D.; Badowski, C.; Speck, M.; Stokes, A.J.; Small-Howard, A.L.; et al. Myrcene and Terpene Regulation of TRPV1. Channels 2019, 13, 344–366.
  63. Bomfim, L.M.; Menezes, L.R.A.; Rodrigues, A.C.B.C.; Dias, R.B.; Gurgel Rocha, C.A.; Soares, M.B.P.; Neto, A.F.S.; Nascimento, M.P.; Campos, A.F.; Silva, L.C.R.C.e.; et al. Antitumour Activity of the Microencapsulation of Annona vepretorum Essential Oil. Basic Clin. Pharmacol. Toxicol. 2016, 118, 208–213.
  64. Sayyah, M.; Nadjafnia, L.; Kamalinejad, M. Anticonvulsant Activity and Chemical Composition of Artemisia dracunculus L. Essential Oil. J. Ethnopharmacol. 2004, 94, 283–287.
  65. Pulaj, B.; Mustafa, B.; Nelson, K.; Quave, C.L.; Hajdari, A. Chemical Composition and in Vitro Antibacterial Activity of Pistacia terebinthus Essential Oils Derived from Wild Populations in Kosovo. BMC Complement. Altern. Med. 2016, 16, 147.
  66. Zhang, J.; Sun, H.; Chen, S.; Zeng, L.; Wang, T. Anti-Fungal Activity, Mechanism Studies on α-Phellandrene and Nonanal against Penicillium cyclopium. Bot. Stud. 2017, 58, 13.
  67. Piccinelli, A.C.; Santos, J.A.; Konkiewitz, E.C.; Oesterreich, S.A.; Formagio, A.S.N.; Croda, J.; Ziff, E.B.; Kassuya, C.A.L. Antihyperalgesic and Antidepressive Actions of (R)-(+)-Limonene, α-Phellandrene, and Essential Oil from Schinus terebinthifolius Fruits in a Neuropathic Pain Model. Nutr. Neurosci. 2015, 18, 217–224.
  68. Lima, D.F.; Brandão, M.S.; Moura, J.B.; Leitão, J.M.R.S.; Carvalho, F.A.A.; Miúra, L.M.C.V.; Leite, J.R.S.A.; Sousa, D.P.; Almeida, F.R.C. Antinociceptive Activity of the Monoterpene α-Phellandrene in Rodents: Possible Mechanisms of Action. J. Pharm. Pharmacol. 2012, 64, 283–292.
  69. Lin, J.-J.; Lu, K.-W.; Ma, Y.-S.; Tang, N.-Y.; Wu, P.-P.; Wu, C.-C.; Lu, H.-F.; Lin, J.-G.; Chung, J.-G. Alpha-Phellandrene, a Natural Active Monoterpene, Influences a Murine WEHI-3 Leukemia Model in Vivo by Enhancing Macrophague Phagocytosis and Natural Killer Cell Activity. In Vivo 2014, 28, 583–588.
  70. Karthikeyan, R.; Kanimozhi, G.; Prasad, N.R.; Agilan, B.; Ganesan, M.; Srithar, G. Alpha Pinene Modulates UVA-Induced Oxidative Stress, DNA Damage and Apoptosis in Human Skin Epidermal Keratinocytes. Life Sci. 2018, 212, 150–158.
  71. Hou, J.; Zhang, Y.; Zhu, Y.; Zhou, B.; Ren, C.; Liang, S.; Guo, Y. α-Pinene Induces Apoptotic Cell Death via Caspase Activation in Human Ovarian Cancer Cells. Med. Sci. Monit. 2019, 25, 6631–6638.
  72. Rodrigues, K.A.d.F.; Amorim, L.V.; Dias, C.N.; Moraes, D.F.C.; Carneiro, S.M.P.; Carvalho, F.A.d.A. Syzygium Cumini (L.) Skeels Essential Oil and Its Major Constituent α-Pinene Exhibit Anti-Leishmania Activity through Immunomodulation in Vitro. J. Ethnopharmacol. 2015, 160, 32–40.
  73. Pinheiro, M.A.; Magalhães, R.; Torres, D.; Cavalcante, R.; Mota, F.X.; Oliveira Coelho, E.A.; Moreira, H.; Lima, G.; da Costa Araújo, P.; Cardoso, J.L.; et al. Gastroprotective Effect of Alpha-Pinene and Its Correlation with Antiulcerogenic Activity of Essential Oils Obtained from Hyptis Species. Pharmacogn. Mag. 2015, 11, 123.
  74. Matthews Jucá, D.; da Silva, M.; Palheta Junior, R.; de Lima, F.; Okoba, W.; Lahlou, S.; de Oliveira, R.; dos Santos, A.; Magalhães, P. The Essential Oil of Eucalyptus tereticornis and Its Constituents, α- and β-Pinene, Show Accelerative Properties on Rat Gastrointestinal Transit. Planta Med. 2011, 77, 57–59.
  75. Utegenova, G.; Pallister, K.; Kushnarenko, S.; Özek, G.; Özek, T.; Abidkulova, K.; Kirpotina, L.; Schepetkin, I.; Quinn, M.; Voyich, J. Chemical Composition and Antibacterial Activity of Essential Oils from Ferula L. Species against Methicillin-Resistant Staphylococcus aureus. Molecules 2018, 23, 1679.
  76. Yang, Z.; Wu, N.; Zu, Y.; Fu, Y. Comparative Anti-Infectious Bronchitis Virus (IBV) Activity of (-)-Pinene: Effect on Nucleocapsid (N) Protein. Molecules 2011, 16, 1044–1054.
  77. Zamyad, M.; Abbasnejad, M.; Esmaeili-Mahani, S.; Mostafavi, A.; Sheibani, V. The Anticonvulsant Effects of Ducrosia anethifolia (Boiss) Essential Oil Are Produced by Its Main Component Alpha-Pinene in Rats. Arq. Neuropsiquiatr. 2019, 77, 106–114.
  78. Wang, Y.; Wu, C.; Zhang, Q.; Shan, Y.; Gu, W.; Wang, S. Design, Synthesis and Biological Evaluation of Novel β-Pinene-Based Thiazole Derivatives as Potential Anticancer Agents via Mitochondrial-Mediated Apoptosis Pathway. Bioorg. Chem. 2019, 84, 468–477.
  79. Liao, S.; Shang, S.; Shen, M.; Rao, X.; Si, H.; Song, J.; Song, Z. One-Pot Synthesis and Antimicrobial Evaluation of Novel 3-Cyanopyridine Derivatives of (−)-β-Pinene. Bioorg. Med. Chem. Lett. 2016, 26, 1512–1515.
  80. Felipe, C.F.B.; Albuquerque, A.M.S.; de Pontes, J.L.X.; de Melo, J.Í.V.; Rodrigues, T.C.M.L.; de Sousa, A.M.P.; Monteiro, Á.B.; Ribeiro, A.E.d.S.; Lopes, J.P.; de Menezes, I.R.A.; et al. Comparative Study of Alpha- and Beta-Pinene Effect on PTZ-Induced Convulsions in Mice. Fundam. Clin. Pharmacol. 2019, 33, 181–190.
  81. Assimopoulou, A.N.; Sinakos, Z.; Papageorgiou, V.P. Radical Scavenging Activity of Crocus sativus L. Extract and Its Bioactive Constituents. Phytother. Res. 2005, 19, 997–1000.
  82. Pintado, C.; de Miguel, A.; Acevedo, O.; Nozal, L.; Novella, J.L.; Rotger, R. Bactericidal Effect of Saffron (Crocus sativus L.) on Salmonella enterica during Storage. Food Control 2011, 22, 638–642.
  83. Hosseinzadeh, H.; Talebzadeh, F. Anticonvulsant Evaluation of Safranal and Crocin from Crocus sativus in Mice. Fitoterapia 2005, 76, 722–724.
  84. Hosseinzadeh, H.; Noraei, N.B. Anxiolytic and Hypnotic Effect of Crocus sativus Aqueous Extract and Its Constituents, Crocin and Safranal, in Mice. Phytother. Res. 2009, 23, 768–774.
  85. Kianbakht, S.; Mozaffari, K. Effects of Saffron and Its Active Constituents, Crocin and Safranal, on Prevention of Indomethacin Induced Gastric Ulcers in Diabetic and Nondiabetic Rats. JMPIR 2009, 8, 30–38.
  86. Rudbäck, J.; Bergström, M.A.; Börje, A.; Nilsson, U.; Karlberg, A.-T. α-Terpinene, an Antioxidant in Tea Tree Oil, Autoxidizes Rapidly to Skin Allergens on Air Exposure. Chem. Res. Toxicol. 2012, 25, 713–721.
  87. Baldissera, M.D.; Grando, T.H.; Souza, C.F.; Gressler, L.T.; Stefani, L.M.; da Silva, A.S.; Monteiro, S.G. In Vitro and in Vivo Action of Terpinen-4-Ol, γ-Terpinene, and α-Terpinene against Trypanosoma evansi. Exp. Parasitol. 2016, 162, 43–48.
  88. Fadel, H.; Kebbi, S.; Chalchat, J.-C.; Figueredo, G.; Chalard, P.; Benayache, F.; Ghedadba, N.; Benayache, S. Identification of Volatile Components and Antioxidant Assessment of the Aerial Part Extracts from an Algerian Cistus albidus L. of the Aures Region. J. New Technol. Mater. 2020, 10, 38–46.
  89. Khaleel, C.; Tabanca, N.; Buchbauer, G. α-Terpineol, a Natural Monoterpene: A Review of Its Biological Properties. Open Chem. 2018, 16, 349–361.
  90. Couladis, M.; Chinou, I.B.; Tzakou, O.; Petrakis, P.V. Composition and Antimicrobial Activity of the Essential Oil Of Hypericum rumeliacum Subsp.Apollinis (Boiss. & Heldr.). Phytother. Res. 2003, 17, 152–154.
  91. Souza, R.; Cardoso, M.; Menezes, C.; Silva, J.; De Sousa, D.; Batista, J. Gastroprotective Activity of α-Terpineol in Two Experimental Models of Gastric Ulcer in Rats. Daru J. Fac. Pharm. Tehran Univ. Med. Sci. 2011, 19, 277–281.
  92. Nagoor Meeran, M.F.; Javed, H.; Al Taee, H.; Azimullah, S.; Ojha, S.K. Pharmacological Properties and Molecular Mechanisms of Thymol: Prospects for Its Therapeutic Potential and Pharmaceutical Development. Front. Pharmacol. 2017, 8, 380.
  93. Nagoor Meeran, M.F.; Jagadeesh, G.S.; Selvaraj, P. Thymol, a Dietary Monoterpene Phenol Abrogates Mitochondrial Dysfunction in β-Adrenergic Agonist Induced Myocardial Infarcted Rats by Inhibiting Oxidative Stress. Chem. Biol. Interact. 2016, 244, 159–168.
  94. Saravanan, S.; Pari, L. Role of Thymol on Hyperglycemia and Hyperlipidemia in High Fat Diet-Induced Type 2 Diabetic C57BL/6J Mice. Eur. J. Pharmacol. 2015, 761, 279–287.
  95. Mendes, S.S.; Bomfim, R.R.; Jesus, H.C.R.; Alves, P.B.; Blank, A.F.; Estevam, C.S.; Antoniolli, A.R.; Thomazzi, S.M. Evaluation of the Analgesic and Anti-Inflammatory Effects of the Essential Oil of Lippia gracilis Leaves. J. Ethnopharmacol. 2010, 129, 391–397.
  96. Bukovská, A.; Cikoš, Š.; Juhás, Š.; Il’ková, G.; Rehák, P.; Koppel, J. Effects of a Combination of Thyme and Oregano Essential Oils on TNBS-Induced Colitis in Mice. Mediators Inflamm. 2007, 1–9.
  97. Bhandari, S.S.; Kabra, M.P. To Evaluate Anti-Anxiety Activity of Thymol. J. Acute Dis. 2014, 3, 136–140.
  98. López-Carbonell, M.; Gabasa, M.; Jáuregui, O. Enhanced Determination of Abscisic Acid (ABA) and Abscisic Acid Glucose Ester (ABA-GE) in Cistus albidus Plants by Liquid Chromatography-Mass Spectrometry in Tandem Mode. Plant Physiol. Biochem. 2009, 47, 256–261.
  99. Pérez-Llorca, M.; Caselles, V.; Müller, M.; Munné-Bosch, S. The Threshold between Life and Death in Cistus albidus L. Seedlings: Mechanisms Underlying Drought Tolerance and Resilience. Tree Physiol. 2021, 41, 1861–1876.
  100. Bassaganya-Riera, J.; Skoneczka, J.; Kingston, D.G.J.; Krishnan, A.; Misyak, S.A.; Guri, A.J.; Pereira, A.; Carter, A.B.; Minorsky, P.; Tumarkin, R.; et al. Mechanisms of Action and Medicinal Applications of Abscisic Acid. Curr. Med. Chem. 2010, 17, 467–478.
  101. Mollashahi, M.; Abbasnejad, M.; Esmaeili-Mahani, S. Phytohormone Abscisic Acid Elicits Antinociceptive Effects in Rats through the Activation of Opioid and Peroxisome Proliferator-Activated Receptors β/δ. Eur. J. Pharmacol. 2018, 832, 75–80.
  102. Mulyaningsih, S.; Sporer, F.; Zimmermann, S.; Reichling, J.; Wink, M. Synergistic Properties of the Terpenoids Aromadendrene and 1,8-Cineole from the Essential Oil of Eucalyptus globulus against Antibiotic-Susceptible and Antibiotic-Resistant Pathogens. Phytomedicine 2010, 17, 1061–1066.
  103. Yeo, S.K.; Ali, A.Y.; Hayward, O.A.; Turnham, D.; Jackson, T.; Bowen, I.D.; Clarkson, R. β-Bisabolene, a Sesquiterpene from the Essential Oil Extract of Opoponax (Commiphora guidottii), Exhibits Cytotoxicity in Breast Cancer Cell Lines: Anti-tumour properties of β-bisabolene. Phytother. Res. 2016, 30, 418–425.
  104. Maurya, A.K.; Singh, M.; Dubey, V.; Srivastava, S.; Luqman, S.; Bawankule, D.U. α-(-)-Bisabolol Reduces pro-Inflammatory Cytokine Production and Ameliorates Skin Inflammation. Curr. Pharm. Biotechnol. 2014, 15, 173–181.
  105. van Zyl, R.L.; Seatlholo, S.T.; van Vuuren, S.F.; Viljoen, A.M. The Biological Activities of 20 Nature Identical Essential Oil Constituents. J. Essent. Oil Res. 2006, 18, 129–133.
  106. Seki, T.; Kokuryo, T.; Yokoyama, Y.; Suzuki, H.; Itatsu, K.; Nakagawa, A.; Mizutani, T.; Miyake, T.; Uno, M.; Yamauchi, K.; et al. Antitumor Effects of α-Bisabolol against Pancreatic Cancer. Cancer Sci. 2011, 102, 2199–2205.
  107. Ho, C.-L.; Liao, P.-C.; Wang, E.I.-C.; Su, Y.-C. Composition and Antifungal Activities of the Leaf Essential Oil of Neolitsea parvigemma from Taiwan. Nat. Prod. Commun. 2011, 6, 1357–1360.
  108. Mastino, P.M.; Marchetti, M.; Costa, J.; Usai, M. Comparison of Essential Oils from Cistus Species Growing in Sardinia. Nat. Prod. Res. 2017, 31, 299–307.
  109. Takei, M.; Umeyama, A.; Arihara, S. T-Cadinol and Calamenene Induce Dendritic Cells from Human Monocytes and Drive Th1 Polarization. Eur. J. Pharmacol. 2006, 537, 190–199.
  110. Dahham, S.; Tabana, Y.; Iqbal, M.; Ahamed, M.; Ezzat, M.; Majid, A.; Majid, A. The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna. Molecules 2015, 20, 11808–11829.
  111. Ojha, S.; Javed, H.; Azimullah, S.; Haque, M.E. β-Caryophyllene, a Phytocannabinoid Attenuates Oxidative Stress, Neuroinflammation, Glial Activation, and Salvages Dopaminergic Neurons in a Rat Model of Parkinson Disease. Mol. Cell. Biochem. 2016, 418, 59–70.
  112. Bahi, A.; Al Mansouri, S.; Al Memari, E.; Al Ameri, M.; Nurulain, S.M.; Ojha, S. β-Caryophyllene, a CB2 Receptor Agonist Produces Multiple Behavioral Changes Relevant to Anxiety and Depression in Mice. Physiol. Behav. 2014, 135, 119–124.
  113. de Oliveira, C.C.; de Oliveira, C.V.; Grigoletto, J.; Ribeiro, L.R.; Funck, V.R.; Grauncke, A.C.B.; de Souza, T.L.; Souto, N.S.; Furian, A.F.; Menezes, I.R.A.; et al. Anticonvulsant Activity of β-Caryophyllene against Pentylenetetrazol-Induced Seizures. Epilepsy Behav. 2016, 56, 26–31.
  114. Fidyt, K.; Fiedorowicz, A.; Strządała, L.; Szumny, A. β-Caryophyllene and β-Caryophyllene Oxide-Natural Compounds of Anticancer and Analgesic Properties. Cancer Med. 2016, 5, 3007–3017.
  115. Türkez, H.; Çelik, K.; Toğar, B. Effects of Copaene, a Tricyclic Sesquiterpene, on Human Lymphocytes Cells in Vitro. Cytotechnology 2014, 66, 597–603.
  116. Turkez, H.; Togar, B.; Tatar, A. Tricyclic Sesquiterpene Copaene Prevents H2O2-Induced Neurotoxicity. J. Intercult. Ethnopharmacol. 2014, 3, 21.
  117. Park, S.Y.; Park, S.J.; Park, N.J.; Joo, W.H.; Lee, S.-J.; Choi, Y.-W. α-Iso-Cubebene Exerts Neuroprotective Effects in Amyloid Beta Stimulated Microglia Activation. Neurosci. Lett. 2013, 555, 143–148.
  118. Lee, S.K.; Kim, S.D.; Lee, H.Y.; Baek, S.-H.; Ko, M.J.; Son, B.G.; Park, S.; Choi, Y.W.; Bae, Y.-S. α-Iso-Cubebene, a Natural Compound Isolated from Schisandra chinensis Fruit, Has Therapeutic Benefit against Polymicrobial Sepsis. Biochem. Biophys. Res. Commun. 2012, 426, 226–231.
  119. Baek, S.E.; Jang, E.J.; Choi, J.M.; Choi, Y.W.; Kim, C.D. α-Iso-Cubebene Attenuates Neointima Formation by Inhibiting HMGB1-Induced Monocyte to Macrophage Differentiation via Suppressing ROS Production. Int. Immunopharmacol. 2022, 111, 109121.
  120. Rodrigo, G.; Almanza, G.R.; Cheng, Y.; Peng, J.; Hamann, M.; Duan, R.-D.; Åkesson, B. Antiproliferative Effects of Curcuphenol, a Sesquiterpene Phenol. Fitoterapia 2010, 81, 762–766.
  121. Bai, Z.; Yao, C.; Zhu, J.; Xie, Y.; Ye, X.-Y.; Bai, R.; Xie, T. Anti-Tumor Drug Discovery Based on Natural Product β-Elemene: Anti-Tumor Mechanisms and Structural Modification. Molecules 2021, 26, 1499.
  122. Asakura, K.; Matsuo, Y.; Oshima, T.; Kihara, T.; Minagawa, K.; Araki, Y.; Kagawa, K.; Kanemasa, T.; Ninomiya, M. ω-Agatoxin IVA-Sensitive Ca2+ Channel Blocker, α-Eudesmol, Protects against Brain Injury after Focal Ischemia in Rats. Eur. J. Pharmacol. 2000, 394, 57–65.
  123. Moon, P.-D.; Han, N.-R.; Lee, J.S.; Kim, H.-Y.; Hong, S.; Kim, H.-J.; Yoo, M.-S.; Kim, H.-M.; Jeong, H.-J. β-Eudesmol Inhibits Thymic Stromal Lymphopoietin through Blockade of Caspase-1/NF-ΚB Signal Cascade in Allergic Rhinitis Murine Model. Chem. Biol. Interact. 2018, 294, 101–106.
  124. Narahara, C.; Saeheng, T.; Chaijaroenkul, W.; Dumre, S.P.; Na-Bangchang, K.; Karbwang, J. β-Eudesmol Induces the Expression of Apoptosis Pathway Proteins in Cholangiocarcinoma Cell Lines. J. Res. Med. Sci. Off. J. Isfahan Univ. Med. Sci. 2020, 25, 7.
  125. Dhyani, P.; Sati, P.; Sharma, E.; Attri, D.C.; Bahukhandi, A.; Tynybekov, B.; Szopa, A.; Sharifi-Rad, J.; Calina, D.; Suleria, H.A.R.; et al. Sesquiterpenoid Lactones as Potential Anti-Cancer Agents: An Update on Molecular Mechanisms and Recent Studies. Cancer Cell Int. 2022, 22, 305.
  126. Guedes, J.B.; do Nascimento, A.L.; Costa, W.K.; de Veras, B.O.; de Aguiar, J.C.R.d.O.F.; Navarro, D.M.d.A.F.; Napoleão, T.H.; da Silva, M.V.; de Oliveira, A.M.; Correia, M.T.d.S. Eugenia gracillima Essential Oil Has Pharmaceutical Applications in Pain and Inflammation without Toxic Effects in Mice. J. Ethnopharmacol. 2023, 303, 115941.
  127. Casiglia, S.; Bruno, M.; Bramucci, M.; Quassinti, L.; Lupidi, G.; Fiorini, D.; Maggi, F. Kundmannia sicula (L.) DC: A Rich Source of Germacrene D. J. Essent. Oil Res. 2017, 29, 437–442.
  128. Mendes De Lacerda Leite, G.; De Oliveira Barbosa, M.; Pereira Lopes, M.J.; De Araújo Delmondes, G.; Bezerra, D.S.; Araújo, I.M.; Carvalho De Alencar, C.D.; Melo Coutinho, H.D.; Peixoto, L.R.; Barbosa-Filho, J.M.; et al. Pharmacological and Toxicological Activities of α-Humulene and Its Isomers: A Systematic Review. Trends Food Sci. Technol. 2021, 115, 255–274.
  129. Sabir, U.; Irfan, H.M.; Alamgeer Ullah, A.; Althobaiti, Y.S.; Alshehri, F.S.; Niazi, Z.R. Downregulation of Hepatic Fat Accumulation, Inflammation and Fibrosis by Nerolidol in Purpose Built Western-Diet-Induced Multiple-Hit Pathogenesis of NASH Animal Model. Biomed. Pharmacother. 2022, 150, 112956.
  130. Dong, J.-R.; Chang, W.-W.; Chen, S.-M. Nerolidol Inhibits Proliferation of Leiomyoma Cells via Reactive Oxygen Species-Induced DNA Damage and Downregulation of the ATM/Akt Pathway. Phytochemistry 2021, 191, 112901.
  131. Misra, B.B.; Dey, S. Evaluation of in Vivo Anti-Hyperglycemic and Antioxidant Potentials of α-Santalol and Sandalwood Oil. Phytomedicine 2013, 20, 409–416.
  132. Garlet, Q.I.; Souza, C.F.; Rodrigues, P.; Descovi, S.N.; Martinez-Rodríguez, G.; Baldisserotto, B.; Heinzmann, B.M. GABAa Receptor Subunits Expression in Silver Catfish (Rhamdia Quelen) Brain and Its Modulation by Nectandra grandiflora Nees Essential Oil and Isolated Compounds. Behav. Brain Res. 2019, 376, 112178.
  133. Tyagi, A.K.; Prasad, S.; Yuan, W.; Li, S.; Aggarwal, B.B. Identification of a Novel Compound (β-Sesquiphellandrene) from Turmeric (Curcuma longa) with Anticancer Potential: Comparison with Curcumin. Investig. New Drugs 2015, 33, 1175–1186.
  134. Zhao, J.; Zhang, J.; Yang, B.; Lv, G.-P.; Li, S.-P. Free Radical Scavenging Activity and Characterization of Sesquiterpenoids in Four Species of Curcuma Using a TLC Bioautography Assay and GC-MS Analysis. Molecules 2010, 15, 7547–7557.
  135. Martins, R.M.G.; Xavier-Júnior, F.H.; Barros, M.R.; Menezes, T.M.; de Assis, C.R.D.; de Melo, A.C.G.R.; Veras, B.O.; Ferraz, V.P.; Filho, A.A.M.; Yogui, G.T.; et al. Impact on Cholinesterase-Inhibition and in Silico Investigations of Sesquiterpenoids from Amazonian Siparuna guianensis Aubl. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2021, 252, 119511.
  136. Manjima, R.B.; Ramya, S.; Kavithaa, K.; Paulpandi, M.; Saranya, T.; Harysh Winster, S.B.; Balachandar, V.; Arul, N. Spathulenol Attenuates 6-Hydroxydopamine Induced Neurotoxicity in SH-SY5Y Neuroblastoma Cells. Gene Rep. 2021, 25, 101396.
  137. do Nascimento, K.F.; Moreira, F.M.F.; Alencar Santos, J.; Kassuya, C.A.L.; Croda, J.H.R.; Cardoso, C.A.L.; Vieira, M.d.C.; Góis Ruiz, A.L.T.; Ann Foglio, M.; de Carvalho, J.E.; et al. Antioxidant, Anti-Inflammatory, Antiproliferative and Antimycobacterial Activities of the Essential Oil of Psidium guineense Sw. and Spathulenol. J. Ethnopharmacol. 2018, 210, 351–358.
  138. de Matos Balsalobre, N.; dos Santos, E.; Mariano dos Santos, S.; Arena, A.C.; Konkiewitz, E.C.; Ziff, E.B.; Nazari Formagio, A.S.; Leite Kassuya, C.A. Potential Anti-Arthritic and Analgesic Properties of Essential Oil and Viridiflorol Obtained from Allophylus edulis Leaves in Mice. J. Ethnopharmacol. 2023, 301, 115785.
  139. Akiel, M.A.; Alshehri, O.Y.; Aljihani, S.A.; Almuaysib, A.; Bader, A.; Al-Asmari, A.I.; Alamri, H.S.; Alrfaei, B.M.; Halwani, M.A. Viridiflorol Induces Anti-Neoplastic Effects on Breast, Lung, and Brain Cancer Cells through Apoptosis. Saudi J. Biol. Sci. 2022, 29, 816–821.
  140. Trevizan, L.N.F.; Nascimento, K.F.d.; Santos, J.A.; Kassuya, C.A.L.; Cardoso, C.A.L.; Vieira, M.d.C.; Moreira, F.M.F.; Croda, J.; Formagio, A.S.N. Anti-Inflammatory, Antioxidant and Anti-Mycobacterium tuberculosis Activity of Viridiflorol: The Major Constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk. J. Ethnopharmacol. 2016, 192, 510–515.
  141. Oon, S.F.; Nallappan, M.; Tee, T.T.; Shohaimi, S.; Kassim, N.K.; Sa’ariwijaya, M.S.F.; Cheah, Y.H. Xanthorrhizol: A Review of Its Pharmacological Activities and Anticancer Properties. Cancer Cell Int. 2015, 15, 100.
  142. Mordukhova, E.A.; Kim, D.; Kim, W.-G.; Hwang, J.-K.; Pan, J.-G. The Food-Grade Antimicrobial Xanthorrhizol Targets the Enoyl-ACP Reductase (FabI) in Escherichia coli. Bioorg. Med. Chem. Lett. 2020, 30, 127651.
  143. Oon, S.F.; Nallappan, M.; Kassim, N.K.; Shohaimi, S.; Sa’ariwijaya, M.S.F.; Tee, T.T.; Cheah, Y.H. Hypolipidemic Activities of Xanthorrhizol Purified from Centrifugal TLC. Biochem. Biophys. Res. Commun. 2016, 478, 1403–1408.
  144. Cho, J.Y.; Hwang, J.-K.; Chun, H.S. Xanthorrhizol Attenuates Dextran Sulfate Sodium-Induced Colitis via the Modulation of the Expression of Inflammatory Genes in Mice. Life Sci. 2011, 88, 864–870.
  145. Borgonetti, V.; Governa, P.; Manetti, F.; Galeotti, N. Zingiberene, a Non-Zinc-Binding Class I HDAC Inhibitor: A Novel Strategy for the Management of Neuropathic Pain. Phytomedicine 2023, 111, 154670.
  146. Bou, D.; Lago, J.; Figueiredo, C.; Matsuo, A.; Guadagnin, R.; Soares, M.; Sartorelli, P. Chemical Composition and Cytotoxicity Evaluation of Essential Oil from Leaves of Casearia sylvestris, Its Main Compound α-Zingiberene and Derivatives. Molecules 2013, 18, 9477–9487.
  147. Ferreira, B.A.; Silva, R.F.; de Moura, F.B.R.; Narduchi, C.T.; Deconte, S.R.; Sartorelli, P.; Tomiosso, T.C.; Lago, J.H.G.; Araújo, F. de A. α-Zingiberene, a Sesquiterpene from Essential Oil from Leaves of Casearia sylvestris, Suppresses Inflammatory Angiogenesis and Stimulates Collagen Deposition in Subcutaneous Implants in Mice. Nat. Prod. Res. 2022, 36, 5858–5862.
  148. Ravera, S.; Esposito, A.; Degan, P.; Caicci, F.; Manni, L.; Liguori, A.; Bisio, A.; Iobbi, V.; Schito, A.; Traverso, C.E.; et al. The diterpene manool extracted from Salvia tingitana lowers free radical production in retinal rod outer segments by inhibiting the extramitochondrial F1 F0 ATP synthase. Cell Biochem. Funct. 2021, 39, 528–535.
  149. Nicolella, H.D.; de Oliveira, P.F.; Munari, C.C.; Costa, G.F.D.; Moreira, M.R.; Veneziani, R.C.S.; Tavares, D.C. Differential Effect of Manool—A Diterpene from Salvia officinalis, on Genotoxicity Induced by Methyl Methanesulfonate in V79 and HepG2 Cells. Food Chem. Toxicol. 2014, 72, 8–12.
  150. Monteiro, A.S.e.N.; Campos, D.R.; Albuquerque, A.A.S.; Evora, P.R.B.; Ferreira, L.G.; Celotto, A.C. Efeito Do Diterpeno Manool Sobre a Pressão Arterial e Reatividade Vascular Em Ratos Normotensos e Hipertensos. Arq. Bras. Cardiol. 2020, 115, 669–677.
  151. Castro, C.H.; Pontes, C.N.R. Efeitos Cardiovasculares Do Diterpeno Manool Em Ratos Normotensos e Hipertensos. Arq. Bras. Cardiol. 2020, 115, 678–679.
  152. Angelopoulou, D.; Demetzos, C.; Dimas, C.; Perdetzoglou, D.; Loukis, A. Essential Oils and Hexane Extracts from Leaves and Fruits of Cistus monspeliensis. Cytotoxic Activity of Ent-13-Epi-Manoyl Oxide and Its Isomers. Planta Med. 2001, 67, 168–171.
  153. Kim, J.-H.; Na, H.-J.; Kim, C.-K.; Kim, J.-Y.; Ha, K.-S.; Lee, H.; Chung, H.-T.; Kwon, H.J.; Kwon, Y.-G.; Kim, Y.-M. The Non-Provitamin A Carotenoid, Lutein, Inhibits NF-KappaB-Dependent Gene Expression through Redox-Based Regulation of the Phosphatidylinositol 3-Kinase/PTEN/Akt and NF-KappaB-Inducing Kinase Pathways: Role of H(2)O(2) in NF-KappaB Activation. Free Radic. Biol. Med. 2008, 45, 885–896.
  154. Zhang, W.-L.; Zhao, Y.-N.; Shi, Z.-Z.; Cong, D.; Bai, Y.-S. Lutein Inhibits Cell Growth and Activates Apoptosis via the PI3K/AKT/MTOR Signaling Pathway in A549 Human Non-Small-Cell Lung Cancer Cells. J. Environ. Pathol. Toxicol. Oncol. Off. 2018, 37, 341–350.
  155. Li, S.; Ding, Y.; Niu, Q.; Xu, S.; Pang, L.; Ma, R.; Jing, M.; Feng, G.; Tang, J.X.; Zhang, Q.; et al. Lutein Has a Protective Effect on Hepatotoxicity Induced by Arsenic via Nrf2 Signaling. BioMed Res. Int. 2015, 2015, 315205.
  156. Ouyang, B.; Li, Z.; Ji, X.; Huang, J.; Zhang, H.; Jiang, C. The Protective Role of Lutein on Isoproterenol-Induced Cardiac Failure Rat Model through Improving Cardiac Morphology, Antioxidant Status via Positively Regulating Nrf2/HO-1 Signalling Pathway. Pharm. Biol. 2019, 57, 529–535.
  157. Okada, T.; Nakai, M.; Maeda, H.; Hosokawa, M.; Sashima, T.; Miyashita, K. Suppressive Effect of Neoxanthin on the Differentiation of 3T3-L1 Adipose Cells. J. Oleo Sci. 2008, 57, 345–351.
  158. Teuscher, E. Biogene Arzneimittel: Lehrbuch der Pharmazeutischen Biologie; 2020; ISBN 978-3-8047-3607-8. Available online: https://www.amazon.de/Biogene-Arzneimittel-Lehrbuch-Pharmazeutischen-Biologie/dp/3804736076 (accessed on 10 August 2023).
  159. Tomás-Menor, L.; Morales-Soto, A.; Barrajón-Catalán, E.; Roldán-Segura, C.; Segura-Carretero, A.; Micol, V. Correlation between the Antibacterial Activity and the Composition of Extracts Derived from Various Spanish Cistus Species. Food Chem. Toxicol. 2013, 55, 313–322.
  160. Sticher, O.; Heilmann, J.; Zündorf, I.; Hänsel, R.; Steinegger, E. Pharmakognosie—Phytopharmazie; 10., völlig neu Bearbeitete Auflage.; Wissenschaftliche Verlagsgesellschaft: Stuttgart, Germany, 2015; ISBN 978-3-8047-3144-8.
  161. Belitz, H.-D.; Grosch, W.; Schieberle, P. Lehrbuch der Lebensmittelchemie; Springer-Lehrbuch; Sechste, Vollständig Überarbeitete Auflage; Springer: Berlin/Heidelberg, Germany, 2008; ISBN 978-3-540-73201-3.
  162. Mastino, P.; Marchetti, M.A.; Costa, J.; Juliano, C.; Usai, M. Analytical Profiling of Phenolic Compounds in Extracts of Three Cistus Species from Sardinia and Their Potential Antimicrobial and Antioxidant Activity. Chem. Biodivers. 2021, 18, e2100053.
  163. Qa’dan, F.; Petereit, F.; Nahrstedt, A. Prodelphinidin Trimers and Characterization of a Proanthocyanidin Oligomer from Cistus albidus. Pharmazie 2003, 58, 416–419.
  164. Wiesner, J.V. Die Rohstoffe des Pflanzenreiches; Verlag W. Engelmann: Leipzig, Berlin, Germany, 1921.
  165. Gonçalves, S.; Gomes, D.; Costa, P.; Romano, A. The Phenolic Content and Antioxidant Activity of Infusions from Mediterranean Medicinal Plants. Ind. Crops Prod. 2013, 43, 465–471.
  166. Legrum, W. Riechstoffe, Zwischen Gestank und Duft: Vorkommen, Eigenschaften und Anwendung von Riechstoffen und deren Gemischen; Studienbücher Chemie; 1. Aufl.; Vieweg + Teubner: Wiesbaden, Germany, 2011; ISBN 978-3-8348-1245-2.
  167. Fahlbusch, K.-G.; Hammerschmidt, F.-J.; Panten, J.; Pickenhagen, W.; Schatkowski, D.; Bauer, K.; Garbe, D.; Surburg, H. Flavors and Fragrances. In Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA, Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2003; p. a11_141. ISBN 978-3-527-30673-2.
  168. Fenaroli, G.; Burdock, G.A. Fenaroli’s Handbook of Flavor Ingredients, 4th ed.; CRC Press: Boca Raton, FL, USA, 2002; ISBN 978-0-8493-0946-5.
  169. Oñate, M.; Munné-Bosch, S. Loss of Flower Bud Vigour in the Mediterranean Shrub, Cistus albidus L. at Advanced Developmental Stages. Plant Biol. 2010, 12, 475–483.
  170. Jubany-Mari, T.; Munne-Bosch, S.; Lopez-Carbonell, M.; Alegre, L. Hydrogen Peroxide Is Involved in the Acclimation of the Mediterranean Shrub, Cistus albidus L., to Summer Drought. J. Exp. Bot. 2008, 60, 107–120.
  171. Mulet Pascual, L. Estudio Etnobotánico de La Provincia de Castellón; Diputación de Castellón: Castellón, Spain, 1991; ISBN 978-84-86895-24-2.
  172. Wang, H. Epimerisation of Catechins in Green Tea Infusions. Food Chem. 2000, 70, 337–344.
  173. Wang, R.; Zhou, W.; Jiang, X. Reaction Kinetics of Degradation and Epimerization of Epigallocatechin Gallate (EGCG) in Aqueous System over a Wide Temperature Range. J. Agric. Food Chem. 2008, 56, 2694–2701.
  174. Saklar, S.; Ertas, E.; Ozdemir, I.S.; Karadeniz, B. Effects of Different Brewing Conditions on Catechin Content and Sensory Acceptance in Turkish Green Tea Infusions. J. Food Sci. Technol. 2015, 52, 6639–6646.
  175. Verde, A.; Fajardo, J.; Obón, C.; Cebrían, F.; Rivera, D. Guía de las Plantas Medicinales de Castilla-La Mancha; Altabán Ediciones: Albacete, Spain, 2008; ISBN 987-84-96465-53-4.
  176. Alami Merrouni, I.; Kharchoufa, L.; Bencheikh, N.; Elachouri, M. Ethnobotanical Profile of Medicinal Plants Used by People of North-Eastern Morocco: Cross-Cultural and Historical Approach (Part I). Ethnobot. Res. Appl. 2021, 21, 1–45.
  177. Las Plantas En La Cultura Popular de La Provincia de Albacete; Fajardo, J.; Verde, A.; Rivera, D.; Obón, C. (Eds.) Serie I—Estudios; Instituto de Estudios Albacetenses “Don Juan Manuel” de la Excma; Diputacioń de Albacete: Albacete, Spain, 2000; ISBN 978-84-95394-08-8.
  178. Ajjoun, M.; Kharchoufa, L.; Alami Merrouni, I.; Elachouri, M. Moroccan Medicinal Plants Traditionally Used for the Treatment of Skin Diseases: From Ethnobotany to Clinical Trials. J. Ethnopharmacol. 2022, 297, 115532.
  179. Fernández Ocaña, A.M. Estudio Etnobotánico En El Parque Natural de Las Sierras de Cazorla, Segura y Las Villas; Investigación Química de Un Grupo de Especies Interesantes, Departamento de Biología Animal, Vegetal y Ecología, Facultad de Ciencias Experimentales, Universidad de Jaén: Jáen, Spain, 2000.
  180. Fiorini, D.; Molle, A.; Nabissi, M.; Santini, G.; Benelli, G.; Maggi, F. Valorizing Industrial Hemp (Cannabis sativa L.) by-Products: Cannabidiol Enrichment in the Inflorescence Essential Oil Optimizing Sample Pre-Treatment Prior to Distillation. Ind. Crops Prod. 2019, 128, 581–589.
  181. Ross, S.A.; ElSohly, M.A. The Volatile Oil Composition of Fresh and Air-Dried Buds of Cannabis sativa. J. Nat. Prod. 1996, 59, 49–51.
  182. Alcaraz Ariza, F.J.; Le Houérou, H.-N. Flora Básica de la Región de Murcia; Sociedad Cooperativa de Enseñanza Severo Ochoa: Murcia, Spain, 2002; ISBN 978-84-600-9378-7.
  183. Stübing, G.; Peris, J.B. Plantas Medicinales de la Comunidad Valenciana; Generalitat Valenciana, Conselleria de Medio Ambiete: Valencia, Spain, 1998; ISBN 978-84-482-1805-8.
  184. Segarra i Durà, E. Etnobotànica Farmacèutica de Gàtova; Universitat de València: València, Spain, 2008; ISBN 978-84-370-6976-0.
  185. Pardo de Santayana, M. Inventario Español de los Conocimientos Tradicionales Relativos de la Biodiversidad: Primera fase: Introducción, Metodología y Fichas; Ministerio para la Transición Ecológica: Madrid, Spain, 2014; ISBN 978-84-491-1401-4.
  186. Ledesma, J. Estudio Del Uso Tradicional de Las Plantas Silvestres En La Sierra de Montsant; Trabajo Fin de Carrera, Escuela de Ingeniería Forestal de Lleida: Lleida, Spain, 2004.
  187. Carrió Cabrer, M.E. Contribució a l’etnobotànica de Mallorca; La Biodiversitat Vegetal i La Seva Gestió En Una Illa Mediterrània, Universidad de Barcelona: Barcelona, Spain, 2013.
  188. Carrió, E.; Vallès, J. Ethnobotany of Medicinal Plants Used in Eastern Mallorca (Balearic Islands, Mediterranean Sea). J. Ethnopharmacol. 2012, 141, 1021–1040.
  189. Belda, A.; Zaragozí, B.; Belda, I.; Martínez, J.; Seva, E. Traditional Knowledge of Medicinal Plants in the Serra de Mariola Natural Park, South-Eastern Spain. Afr. J. Tradit. Complement. Altern. Med. 2013, 10, 299–309.
  190. Martínez-Lirola, M.J.; González-Tejero, M.R.; Molero-Mesa, J. Ethnobotanical Resources in the Province of Almeria, Spain: Campos de Nijar. Econ. Bot. 1996, 50, 40–56.
  191. Torres-Montes, F. Nombres y Usos Tradicionales de Las Plantas Silvestres En Almería (Estudio Linguistico y Etnografico); Diputación de Almería e Instituto de Estudios Almerienses: Almería, Spain, 2004; ISBN 978-84-8108-313-2.
  192. Alarcόn, R.; Pardo-de-Santayana, M.; Priestley, C.; Morales, R.; Heinrich, M. Medicinal and Local Food Plants in the South of Alava (Basque Country, Spain). J. Ethnopharmacol. 2015, 176, 207–224.
  193. Ortuño Moya, I.M. Etnobotánica de Los Villares y Valdepeñas de Jaén (Sur de La Península Ibérica); Universidad de Jaén—Departamento de Biología Animal, Vegetal y Ecología, Facultad de Ciencias Experimentales: Jaén, Spain, 2004.
  194. Goicoetxea Marcaida, A. Etnobotánica y Medicina Popular en el País Vasco; Pastor: Madrid, Spain, 2017; ISBN 978-84-95461-61-2.
  195. González-Tejero García, M.R. Investigaciones Etnobotánicas En La Provincia de Granada; Departamento de Biología Vegetal, Facultad de Farmacia, Universidad de Granada: Granada, Spain, 1989.
  196. Rivera, D.; Alcaraz, F.; Verde, A.; Fajardo, J.; Obón, C. Las Plantas en la Cultura Popular; SOMEHN (Sociedad Mediterránea de Historia Natural): Murcia, Spain, 2008; ISBN 978-84-931786-0-4.
  197. Guzmán, A. Aproximación a La Etnobotánica de La Provincia de Jaén; Departamento de Biología Vegetal, Universidad de Granada: Granada, Spain, 1997.
  198. Atzei, A.D. Le Piante Nella Tradizione Popolare Della Sardegna: Documentazione Sugli Usi Alimentari, Aromatizzanti, Profumieri, Artigianali, Cosmetici, Medicinali, Veterinari, Magici, Ornamentali, Rituali, Religiosi, Tintori, Antiparassitari e Vari, Delle Piante; C. Delfino: Sassari, Italy, 2003; ISBN 978-88-7138-298-2.
  199. Rivera, D.; Robleda, A.; Obón, C.; Cano, F. Introducción al Mundo de Las Plantas Medicinales En Murcia, 1st ed.; Ayuntamiento de Murcia: Murcia, Spain, 1994; ISBN 978-84-606-1922-2.
  200. Pellicer, J. Costumari Botànic: Recerques Etnobotàniques a Les Comarques Centrals Valencianes; Farga monogràfica, 2nd ed.; Edicions del Bullent: Picanya, Spain, 2000; ISBN 978-84-96187-13-9.
More
© Text is available under the terms and conditions of the Creative Commons Attribution (CC BY) license; additional terms may apply. By using this site, you agree to the Terms and Conditions and Privacy Policy.
This entry is offline, you can click here to edit this entry!
Video Production Service
Feedback