Pectolinarin and Pectolinarigenin

Pectolinarin and Pectolinarigenin: History

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Subjects: Biochemistry & Molecular Biology

Contributor:

Thamere Cheriet

Balkeis Ben-Bachir

Oumelkhir Thamri

Ramdane Seghiri

Ines Mancini

Flavonoids are metabolites widely distributed in plants and commonly present in foods, such as fruits and vegetables. Pectolinarin, which belongs to the flavone subclass, has attracted considerable attention due to its presence in many medicinal plants. It has turned out to be a good biological agent especially due to its antioxidant, anti-inflammatory, antidiabetic, and antitumor activities, evaluated both in vitro and in vivo. Its aglycone, the metabolite pectolinarigenin, is also known for a series of biological properties including anti-inflammatory and antidiabetic effects. In the first overview on the two metabolites here presented, their collection, isolation and the results of their biological evaluation are reported

flavonoids
flavones
anticancer

1. Definition

Flavonoids are metabolites widely distributed in plants and commonly present in foods, such as fruits and vegetables. Based on several evidences, flavonoids have been associated with the role of preventing and managing current diseases such as cancers, diabetes, and cardiovascular disorders.

Pectolinarin, which belongs to the flavone subclass, has attracted considerable attention due to its presence in many medicinal plants. It has turned out to be a good biological agent especially due to its antioxidant, anti-inflammatory, antidiabetic, and antitumor activities, evaluated both in vitro and in vivo. Its aglycone, the metabolite pectolinarigenin, is also known for a series of biological properties including anti-inflammatory and antidiabetic effects.

2. Introduction

The glycosylated flavone pectolinarin was first isolated from Linaria vulgaris [2], a known medicinal Chinese herb used for the internal treatement of digestion problems and urinary disorders, in the external treatment of haemorrhoids, venous skin ulcer, as well as for the washing of festering wounds and skin rashes. It has also displayed anti-inflammatory effect [3] and has been used to treat coughs and asthma [4]. The structure of pectolinarin was determined to be a rutinoside conjugate of pectolinarigenin (=5,7-dihydroxy-4,6-dimethoxyflavone, C₁₇H₁₄O₆) at the 7-O position (pectolinarigenin-7-O-rutinoside, C₂₉H₃₄O₁₅) (Figure 1).

Antibiotics 09 00417 g001 550

Figure 1. Molecular structures of pectolinarin and pectolinarigenin.

Later, pectolinarin and its aglycone pectolinarigenin were identified as the major constituents in many medicinal herbs from different genera around the world. Several studies reported so far prove that the presence of these two flavones has an important role in affecting the biological properties of the following herbs: i) the Korean herb Cirsium setidens (Dunn) Nakai employed for the treatment of hemostasis, hematemesis, hematuria and hypertension [5]; ii) the Chinese herb Cirsium chanroenicum used for detoxification, to treat fever and to enhance blood circulation [6]; iii) Cirsium japonicum DC. employed as an anti-hemorrhagic and uretic agent, as well as prescribed to treat liver and uterine tumours, and leukemia [7]; iv) Kickxia ramosissima (Wall.) Janch., used in Pakistan folk medicine as diuretic and against kidney stones [8], fever and rheumatism [9], and during management of snake and scorpion bites [10]; v) Lantana camara L., used for the treatment of various human ailments, such as ulcers, malaria, influenza, tumors, swellings, bilious fever, eczema eruptions, stomach ache, toothache, and as antiseptic for wounds [11]; and vi) Picnomon acama (L.) Cass., used in Greek folk medicine as hemostatic and spasmolytic agent [12].

Due to the structural similarity of pectolinarigenin to known potent flavonoids such as acacetin (5,7-dihydroxy-4′-methoxyflavone, C₁₆H₁₂O₅), hispidulin (4′,5,7-trihydroxy-6-methoxyflavone, C₁₆H₁₂O₆) and scutellarein (5,6,7,4′-tetrahydroxyflavone, C₁₅H₁₀O₆) and based on the numerous data reported for both pectolinarin and pectolinarigenin, the aim of this work is to provide a comprehensive overview focusing on their isolation.

3. Isolation of Pectolinarin and Pectolinarigenin

Over the last 113 years from its first report [2], pectolinarin was isolated in most cases from the aerial parts of 87 plants belonging to 29 differents genera distributing widely around the world. Most of these plants are used in folk medicine in different parts of the world. Table 1 gathers the 87 plants from which pectolinarin was isolated.

Table 1. Isolation of pectolinarin from the indicated plants, classified according to family, genus and species, and place of collection.

Genus	Species	Collection Place	Reference
Family: Adoxaceae
Viburnum	V. cotinifolium V. mullaha	Kashmir/India Indian Himalayan region	[13] [14]
Family: Asteraceae
Cirsium	C. subcoriaceum C. japonicum C. setosum C. rivulare C. lineare C. nipponicum C. setidens C. pendulum C. chanroenicum C. rhinoceros C. coloradense C. arisanense C. tioganum C. oleraceum C. microspicatum C. babanum C. kagamontanum C. inundatum C. dipsacolepis C. brevicaule C. yezoense C. kamtschaticum C. pectinellum C. bitchuense C. senjonse C. spicatum C. yezonese C. vallis-demonii C. gratiosum C. indundatum C. otayae C. purpuratum C. spinosissimum C. spinosum C. ferum C. kawakamii C. wallichii C. yoshizawae C. matsumurae C. brevistylum C. chlorolepis	Pahuatlan/Mexico Daejeon/S. Korea, Oberndorf/Austria, Chengdu/China, Henan/China Oberndorf/Austria Bialystok/Poland Daejeon/S. Korea Daejeon/S. Korea Daejeon, Wonju, Pyongchang-gun, Gangwondo, Jeongseon-gun, Yanggu/S. Korea Daejeon/S. Korea Daejeon, Sancheong/S. Korea Jeongseon-gun, Jeju Island/S. Korea Laramie/USA Laramie/USA, Vitebsk/Belarus Nemuro, Hatimandake, Memanbetsu, Onsen Kyushu, Hokkaido/Japan Wyoming/USA, Japan Mount Akaishi, Mount Senmai, Shizuoka, Takanomori, Nekura Valley/Japan, Vitebsk/Belarus, Mount Shirouma/Japan la Dotze/Switzerland Hsien/Taiwan Nemuro, Mount Shirouma /Japan, Mount Ali, Chiayi Hsien/Taiwan Ku Kuan, Taichung Haien/Taiwan Mount Shirouma, Mount Hakusan ad pedem/Japan Vancouver/Canada Seongnam/Korea	[15] [7,16–20] [18] [21] [19] [19,22] [19,23–26] [19] [19,26,27] [28,29] [30] [30–32] [16] [33,34] [17,31,35–37] [35] [38] [34] [39] [16,40,41] [41] [35] [34,40] [42] [43]
Duranta	D. plumieri	Rajshahi/Bangladesh	[44]
Hemistepta	H. lyrata	Kangwon/S. Korea	[45]
Picnomon	P. acarna	Mount Hortiatis/Greece	[46]
Family: Bignoniaceae
Distictella	D. elongata	Minas Gerais State/Brazil	[47]
Markhamia	M. lutea	Benguluru/India	[48]
Family: Buddlejaceae
Buddleja	B. officinalis	Anhui/China	[49]
Family: Ericaceae
Rhododendron	R. arboreum	Aligarh/India	[50]
Family: Gesneriaceae
Corallodiscus	C. flabellate	Kunming/China	[51]
Aeschynanthus	A. moningeriae	Jinhua/China	[52]
Family: Lamiaceae
Leucosceptrum	L. canum	Tibet/China	[53]
Teucrium	T. hyrcanicum	Sicily/Italy	[54]
Family: Lythraceae
Lawsonia	L. inermis	Thanjavur/India	[55]
Family: Moraceae
Clerodedrum	C. phlomides	Tamil Nadu/India	[56]
Family: Orchidaceae
Oncidium	O. baueri	Londrina/Brazil	[57,58]
Family: Orobanchaceae
Melampyrum	M. roseum	Suwon/S. Korea	[59]
Family: Plantaginaceae
Scoparia	S. dulcis	Nanning/China	[60]
Family: Poaceae
Oryza	O. sativa	a)	[61]
Family: Ranunculaceae
Trollius	T. ledebourii	Hebei/China	[62]
Family: Rosaceae
Kerria	K. japonica var.	Chongqing/China	[63]
Crataegus	C. laevigata	Bremen/Germany	[64]
Family: Santalaceae
Thesium	T. chinense	Anhui/China	[65]
Family: Scrophulariaceae
Linaria	L. vulgaris L. japonica L. reflexa L. vulgariformis L. popovii L. kurdica L. sessili L. kokanica L. haelava L. simplex L. genistifolia L. dalmatica	Sofia/Bulgaria, Tachkent/Uzbekistan Heilongjiang/China Tottori Prefecture/Japan Constantine/Algeria, Calabria/Italy Tachkent/Uzbekistan Pamir/Tajikistan Mansoura/Egypt Sofia/Bulgaria	[2,66–68] [69–71] [72–75] [66] [76] [77] [67]
	L. scariosa	Msila/Algeria	[78]
Kickxia	K. elatine K. heterophylla K. ramosissima K. abhaica K. spuria K. aegyptiaca	Dustlik/Uzbekistan Mansoura/Egypt Ankara/Turkey Baljurashi/Saudi Arabia Appennines hills/Italy Saudi Arabia	[79] [80] [81,82] [83] [84] [85]
Family: Verbenaceae
Morus	M. alba L.	Hongseong/Korea	[86]
Lantana L. camara		Taichung/Taiwan, Palampur/India, Karachi/Pakistan, Ceará state/Brazil, Manado/Indonesia, Okinawa/Japan	[87–92]
Lippia L. rubella		Minas Gerais/Brazil	[93]
Family: Winteraceae
Tasmannia	T. lanceolata	Go Wild Harvest/Australia	[94]

^a Not found.

Pectolinarigenin is the aglycone part of pectolinarin, which is obtained by hydrolysis reaction [73]. It is also a natural product, isolated and identified from 136 plantes of 71 differents genera. The data are summarized in Table 2, indicating that pectolinarigenin was isolated from 20 different families, especially from Asteraceae with 33 genera and 64 species (47.1%), Lamiaceae with 9 genera and 19 species (14%) and Verbenaceae with 4 genera and 10 species (8%).

Table 2. Isolation of pectolinarigenin from the indicated plants, classified according to family, genus and species, and place of collection.

Genus	Species	Collection Place	Reference
Family: Apiaceae
Coriandrum	C. sativum	Faisalabad/Pakistan	[99]
Family: Aspleniaceae
Asplenium	A. glaucophyllum	West Malysia	[100]
	A. normale	West Malaysia	[101]
Family: Asteraceae
Achillea	A. collina	wet lowland meadows/UK	[102]
	A. asplenifolia
Ajania	A. potaninii	Gansu/China	[103]
Ambrosia	A. camphorate	Baja California/Mexico	[104]
Arnica	A. angustifolia	northwest Canada and Alaska	[105]
	A. Montana	California/USA	[106]
	A. chamissonis	Graines Voltz/France	[107]
	A. montana	Šumava Mounts/Czech	[108]
Artemisia	A. mongolica	Gansu/China	[109]
	A. judaica	St. Catherine, Sinai/Egypt	[110]
	A. monosperma	Cairo/Egypt
	A. herba-alba	Mount Moses/Egypt
	A. xerophytica	South Gobi Aimak/Mongolia	[111]
	A. glabella	Karaganda/Kazakhstan	[112]
	A. vestita	Lhasa/Tibet	[113]
Baccharis	B. trinervis	Costa Rica	[114]
	B. decussata	Venezuela	[115]
	B. concave		[116]
	B. uncinella	Campos do Jordão/Brazil	[117]
	B. conferta	Veracruz/Mexico	[118]
Centaurea	C. alexandrina	Alexandria/Egypt	[119]
	C. aspera	Ribera Baixa/Spain	[120]
	C. cariensis		[121]
	C. collina	Valencia/Spain	[122]
	C. sadleriana	Jakabszállás/Hungary	[123]
	C. moesiaca	Malashevska planina/Bulgaria	[124]
	C. behen	Iran	[125]
Chromolaena	C. odorata	Chonburi/Thailand	[126]
Chrysanthemum	C. pacificum	Tsukuba/Japan	27
	C. shiwogiku	Muroto-misaki/Japan
	C. kinokuniense	Tsukuba/Japan
	C. rupestre	Mount Mikuni/Japan
Cirsium	C. setidens	Jeongseon-gun, Halla of jejudo, Daejeon, Kangwon, Yanggu/S. Korea; Guerrero/Mexico;	[19,24–28,127]
	C. chanroenicum	Daejeon, Ulsan, Sancheong/S. Korea	[26,128]
	C. japonicum	Jiang Xi/China	[129]
	C. arvense	Musa Khel Bannu/Pakistan	[130]
	C. nipponicum	Suwon/S. Korea	[131]
	C. rhinoceros		[132]
Dichrocephala	D. integrifolia	Shanghai/China	[133]
Dugaldia	D. pinetorum	Nuevo Lebn/Mexico	[134]
Eriocephalus	E. giessii	Aus-Koppies/Namibia	[135]
Eupatorium	E. cannabinum	Gronigen/Netherlands	[136]
	E. odoratum	Kuala Pilah/Malaysia	[137,138]
	E. semiserratum	Arkansas/USA	[139]
Fragrant	F. Eupatorium	Guangxi/China	[140]
Grindelia	G. glutinosa	Poconchile, Valle de Liuta, Tarapaca/Chile	[141]
Gutierrezia	G. mandonii	Salta/Argentina	[142]
Helenium	H. integrifolium		[143]
Heterotheca	H. latifolia	San Luis/Argentina	[144]
Hemistepta	H. lyrata	Kangwon/S. Korea	[45]
Hymenoxys	H. jamesii	Coconino/USA	[145]
Iva	I. nevadensis	Tonopah/USA	[146]
	I. frutescens	Franklin/USA	[147]
Jungia	J. polita	San Martin/Argentina	[148]
Olearia	O. paniculata	Dunedin/New Zealand	[149]
Onopordon	O. corymbosum	Barracas, Castellon/Spain	[150]
	O. nervosum	a)	[151]
Santolina	S. chamaecyparissus	Lyon/France	[152]
	S. pinnata	Pisa/Italy	[153]
Saussurea	S. elegans	Murghab/Tajikistan	[154]
Schkuhria	S. pinnata	Cordoba/Argentina	[155]
Seriphidium	S. santolium	Xinjiang Uigour/China	[156]
Stevia	S. laxiflora	Cuernavaca, Morelos/Mexico	[157]
Vernonia	V. cinerea	Pahang/Malaysia	[158]
Family: Betulaceae
Alnus	A. glutinosa	Darmstadt/Germany	[159]
	A. japonica		[160]
Betula	B. ermanii		[159]
	B. verrucosa	a)	[161]
	B. pubescens	Biebrza/Poland	[162]
	B. pendula
Family: Bignoniaceae
Millingtonia	M. hortensis	Khon Kaen/Thailand	[163]
Family: Blechnaceae
Brainea	B. insignis	Yunnan/China	[164]
Family: Boraginaceae
Eriodictyon	E. tomentosum	Placer Co./USA	[165]
Family: Fabaceae
Adesmia	A. grandiflora	a)	[166]
	A. trijuga
	A. horrida
	A. retrofracta
Ononis	O. fruticosa	Los Castanõs/Spain	[167]
	O. natrix
	O. rotundifolia	a)	[168]
Trifolium	T. pratense	Trout Lake/USA	[169]
Family: Lamiaceae
Leucosceptrum	L. canum	a)	[170]
Mentha	M. pulegium	Petite Kabylie/Algeria	[171]
	M. suaveolens
Ocimum	O. americanum	Royal Botanic Gardens, Kew/England	[172]
Otostegia	O. fruticosa	St. Catherine/Egypt	[173]
Salvia	S. trilobu	Marmara island/Turkey	[174]
	S. hypoleuca	Elbruz moun/Russia	[175]
	S. pedicellata	a)	[176]
	S. yosgadensis	Sultanhani/Turkey	[177]
	S. plebeia	a)	[178]
	S. pilifera	Berit Mount/Turkey	[179]
	S. tomentosa	Sofia/Bulgaria	[180]
	S. argentea
Scutellaria	S. polyodon	a)	[181]
	S. przewalskii	Susamyr/Kyrgyzstan	[182]
Sideritis	S. gomerae	Canary islands/Spain	[183]
Teucrium	T. chamaedrys	Eskisehir/Turkey	[184]
Thymus	T. longicaulis	Sar planina/Macedonia	[185]
	T. glabrescens	Skopje/Macedonia
Family: Lythraceae
Lawsonia	L. inermis	Thanjavur/India	[153]
Family: Nothofagaceae
Nothofagus	N. dombeyi	Altos de Lircay/Chile	[186]
Family: Orobanchaceae
Striga	S. passargei	a)	[187]
	S. aspera	a)	[188]
Family: Padaliacea
Sesamum	S. indicum	Gambang/Malaysia	[189]
Family: Plantaginaceae
Digitalis	D. trojana	Kizilcahamam, DemirkOy/Turkey	[190]
	D. orientalis
	D. lanata	a)	[191]
Hebe	H. cupressoides	Dunedin/New Zealand	[192]
Veronica	V. chamaedrys	Rila Mount/Bulgaria	[193]
Veronicastrum	V. latifolium	Yongkang/China	[194]
Family: Portulacaceae
Portulaca	P. oleracea	Tianjin/China	[195]
Family: Ranunculaceae
Trollius	T. chinensis	Hebei/China	[196]
Family: Rosaceae
Rosa	R. damascena	Plovdiv/Bulgaria	[197]
	R. rugosa	Botanischer Garten der TU Darmstadt/Germany	[198]
Family: Scrophulariaceae
Buddleia	B. macrostachya	Sibsagar/India	[199]
Kickxia	K. ramosissima	Takht-e-Nusrati/Pakistan	[200–202]
Limnophila	L. aromatica	Ho Chi Minh/Vietnam	[203]
Linaria	L. vulgaris	Ukrania; China	[68,204]
	L. reflexa	Constantine/Algeria	[73]
	L. kurdica	Ukrania	[204]
	L. scariosa	Msila/Algeria	[78]
Family: Verbenaceae
Clerodendrum	C. siphonenthus	Calcutta, Kalyani/India	[205,206]
	C. phlomidis	Pondicherry, Alanthurai/India	[205–210]
	C. serratum	Bhilai/India	[211]
	C. inerme	Pondicherry/India	[212,213]
	C. neriifolium	a)	[214]
	C. indicum	a)Khao Kho/Thailand	[215,216]
Duranta	D. repens	a)	[217]
	D. plumieri	a)	[44,218]
Lantana	L. camara	Taichung/Taiwan, Palampur/India, Karachi/Pakistan, Ceará state/Brazil, Manado/Indonesia, Okinawa/Japan	[87–92]
Lippia	L. citriodora	Athens/Greece	[219]
Family: Zosteraceae
Phyllospadix	P. japonica	Omaezaki/Japan	[220]

^a) not found.

This entry is adapted from the peer-reviewed paper 10.3390/antibiotics9070417

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