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    Topic review

    Pectolinarin and Pectolinarigenin

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    Submitted by: thamere cheriet

    Definition

    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

    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 [1], 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 [2] and has been used to treat coughs and asthma [3]. 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 [4]; ii) the Chinese herb Cirsium chanroenicum used for detoxification, to treat fever and to enhance blood circulation [5]; iii) Cirsium japonicum DC. employed as an anti-hemorrhagic and uretic agent, as well as prescribed to treat liver and uterine tumours, and leukemia [6]; iv) Kickxia ramosissima (Wall.) Janch., used in Pakistan folk medicine as diuretic and against kidney stones [7], fever and rheumatism [8], and during management of snake and scorpion bites [9]; 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 [10]; and vi) Picnomon acama (L.) Cass., used in Greek folk medicine as hemostatic and spasmolytic agent [11].

    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 [1], 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 Kashmir/India [12]
    V. mullaha Indian Himalayan region [13]
    Family: Asteraceae
    Cirsium C. subcoriaceum Pahuatlan/Mexico [14]
    C. japonicum Daejeon/S. Korea, Oberndorf/Austria, Chengdu/China, Henan/China [6][15][16][17][18][19]
      Oberndorf/Austria  
      Bialystok/Poland  
      Daejeon/S. Korea  
    C. setosum Daejeon/S. Korea [17]
    C. rivulare Daejeon, Wonju, Pyongchang-gun, Gangwondo, Jeongseon-gun, Yanggu/S. Korea [20]
    C. lineare Daejeon/S. Korea [18]
    C. nipponicum Daejeon, Sancheong/S. Korea [18][21]
    C. setidens Jeongseon-gun, Jeju Island/S. Korea [18][22][23][24][25]
      Laramie/USA  
      Laramie/USA, Vitebsk/Belarus  
    C. pendulum Nemuro, Hatimandake, Memanbetsu, Onsen Kyushu, Hokkaido/Japan [18]
    C. chanroenicum   [18][25][26]
    C. rhinoceros   [27][28]
    C. coloradense Wyoming/USA, Japan [29]
    C. arisanense Mount Akaishi, Mount Senmai, Shizuoka, Takanomori, Nekura Valley/Japan, Vitebsk/Belarus,  
    C. tioganum Mount Shirouma/Japan  
    C. oleraceum la Dotze/Switzerland [29][30][31]
      Hsien/Taiwan  
    C. microspicatum Nemuro, Mount Shirouma /Japan, Mount Ali, Chiayi Hsien/Taiwan [15]
    C. babanum Ku Kuan, Taichung Haien/Taiwan  
    C. kagamontanum Mount Shirouma, Mount Hakusan ad pedem/Japan  
    C. inundatum Vancouver/Canada  
    C. dipsacolepis Seongnam/Korea  
    C. brevicaule    
    C. yezoense    
    C. kamtschaticum    
    C. pectinellum    
    C. bitchuense   [32][33]
    C. senjonse   [16][30][34][35][36]
    C. spicatum    
    C. yezonese    
    C. vallis-demonii    
    C. gratiosum    
    C. indundatum    
    C. otayae   [34]
    C. purpuratum    
    C. spinosissimum   [37]
    C. spinosum   [33]
    C. ferum   [38]
    C. kawakamii   [15][39][40]
    C. wallichii   [40]
    C. yoshizawae   [34]
    C. matsumurae   [33]
    C. brevistylum   [41]
    C. chlorolepis   [42]
    Duranta D. plumieri Rajshahi/Bangladesh [43]
    Hemistepta H. lyrata Kangwon/S. Korea [44]
    Picnomon P. acarna Mount Hortiatis/Greece [45]
    Family: Bignoniaceae
    Distictella D. elongata Minas Gerais State/Brazil [46]
    Markhamia M. lutea Benguluru/India [47]
    Family: Buddlejaceae
    Buddleja B. officinalis Anhui/China [48]
    Family: Ericaceae
    Rhododendron R. arboreum Aligarh/India [49]
    Family: Gesneriaceae
    Corallodiscus C. flabellate Kunming/China [50]
    Aeschynanthus A. moningeriae Jinhua/China [51]
    Family: Lamiaceae
    Leucosceptrum L. canum Tibet/China [52]
    Teucrium T. hyrcanicum Sicily/Italy [53]
    Family: Lythraceae
    Lawsonia L. inermis Thanjavur/India [54]
    Family: Moraceae
    Clerodedrum C. phlomides Tamil Nadu/India [55]
    Family: Orchidaceae
    Oncidium O. baueri Londrina/Brazil [56][57]
    Family: Orobanchaceae
    Melampyrum M. roseum Suwon/S. Korea [58]
    Family: Plantaginaceae
    Scoparia S. dulcis Nanning/China [59]
    Family: Poaceae
    Oryza O. sativa a) [60]
    Family: Ranunculaceae
    Trollius T. ledebourii Hebei/China [61]
    Family: Rosaceae
    Kerria K. japonica var. Chongqing/China [62]
    Crataegus C. laevigata Bremen/Germany [63]
    Family: Santalaceae
    Thesium T. chinense Anhui/China [64]
    Family: Scrophulariaceae
    Linaria L. vulgaris Sofia/Bulgaria, Tachkent/Uzbekistan [1][65][66][67]
    L. japonica Heilongjiang/China [68][69][70]
    L. reflexa Tottori Prefecture/Japan [71][72][73][74]
    L. vulgariformis Constantine/Algeria, Calabria/Italy [65]
    L. popovii Tachkent/Uzbekistan  
    L. kurdica    
    L. sessili   [75]
    L. kokanica Pamir/Tajikistan  
    L. haelava   [76]
    L. simplex Mansoura/Egypt [66]
    L. genistifolia Sofia/Bulgaria  
    L. dalmatica    
      L. scariosa Msila/Algeria [77]
    Kickxia K. elatine Dustlik/Uzbekistan [78]
    K. heterophylla Mansoura/Egypt [79]
    K. ramosissima Ankara/Turkey [80][81]
    K. abhaica Baljurashi/Saudi Arabia [82]
      Appennines hills/Italy  
    K. spuria Saudi Arabia [83]
    K. aegyptiaca   [84]
    Family: Verbenaceae
    Morus M. alba L. Hongseong/Korea [85]
    Lantana L. camara Taichung/Taiwan, Palampur/India, Karachi/Pakistan, Ceará state/Brazil, Manado/Indonesia, Okinawa/Japan [86][87][88][89][90][91]
    Lippia L. rubella Minas Gerais/Brazil [92]
    Family: Winteraceae
    Tasmannia T. lanceolata Go Wild Harvest/Australia [93]

    a Not found.

    Pectolinarigenin is the aglycone part of pectolinarin, which is obtained by hydrolysis reaction [72]. 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 [94]
    Family: Aspleniaceae
    Asplenium A. glaucophyllum West Malysia [95]
      A. normale West Malaysia [96]
    Family: Asteraceae
    Achillea A. collina wet lowlandmeadows/UK [97]
      A. asplenifolia    
    Ajania A. potaninii Gansu/China [98]
    Ambrosia A. camphorate Baja California/Mexico [99]
    Arnica A. angustifolia northwestCanada and Alaska [100]
      A. Montana California/USA [101]
      A. chamissonis Graines Voltz/France [102]
      A. montana Šumava Mounts/Czech [103]
    Artemisia A. mongolica Gansu/China [104]
      A. judaica St. Catherine, Sinai/Egypt [105]
      A. monosperma Cairo/Egypt  
      A. herba-alba Mount Moses/Egypt  
      A. xerophytica South Gobi Aimak/Mongolia [106]
      A. glabella Karaganda/Kazakhstan [107]
      A. vestita Lhasa/Tibet [108]
    Baccharis B. trinervis Costa Rica [109]
      B. decussata Venezuela [110]
      B. concave   [111]
      B. uncinella Campos do Jordão/Brazil [112]
      B. conferta Veracruz/Mexico [113]
    Centaurea C. alexandrina Alexandria/Egypt [114]
      C. aspera Ribera Baixa/Spain [115]
      C. cariensis   [116]
      C. collina Valencia/Spain [117]
      C. sadleriana Jakabszállás/Hungary [118]
      C. moesiaca Malashevska planina/Bulgaria [119]
      C. behen Iran [120]
    Chromolaena C. odorata Chonburi/Thailand [121]
    Chrysanthemum C. pacificum Tsukuba/Japan [26]
      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; [18][23][24][25][26][27][122]
      C. chanroenicum Daejeon, Ulsan, Sancheong/S. Korea [25][123]
      C. japonicum Jiang Xi/China [124]
      C. arvense Musa Khel Bannu/Pakistan [125]
      C. nipponicum Suwon/S. Korea [126]
      C. rhinoceros   [127]
    Dichrocephala D. integrifolia Shanghai/China [128]
    Dugaldia D. pinetorum Nuevo Lebn/Mexico [129]
    Eriocephalus E. giessii Aus-Koppies/Namibia [130]
    Eupatorium E. cannabinum Gronigen/Netherlands [131]
      E. odoratum Kuala Pilah/Malaysia [132][133]
      E. semiserratum Arkansas/USA [134]
    Fragrant F. Eupatorium Guangxi/China [135]
    Grindelia G. glutinosa Poconchile, Valle deLiuta, Tarapaca/Chile [136]
    Gutierrezia G. mandonii Salta/Argentina [137]
    Helenium H. integrifolium   [138]
    Heterotheca H. latifolia San Luis/Argentina [139]
    Hemistepta H. lyrata Kangwon/S. Korea [44]
    Hymenoxys H. jamesii Coconino/USA [140]
    Iva I. nevadensis Tonopah/USA [141]
      I. frutescens Franklin/USA [142]
    Jungia J. polita San Martin/Argentina [143]
    Olearia O. paniculata Dunedin/New Zealand [144]
    Onopordon O. corymbosum Barracas, Castellon/Spain [145]
      O. nervosum a) [146]
    Santolina S. chamaecyparissus Lyon/France [147]
      S. pinnata Pisa/Italy [148]
    Saussurea S. elegans Murghab/Tajikistan [149]
    Schkuhria S. pinnata Cordoba/Argentina [150]
    Seriphidium S. santolium Xinjiang Uigour/China [151]
    Stevia S. laxiflora Cuernavaca, Morelos/Mexico [152]
    Vernonia V. cinerea Pahang/Malaysia [153]
    Family: Betulaceae
    Alnus A. glutinosa Darmstadt/Germany [154]
      A. japonica   [155]
    Betula B. ermanii   [154]
      B. verrucosa a) [156]
      B. pubescens Biebrza/Poland [157]
      B. pendula    
    Family: Bignoniaceae
    Millingtonia M. hortensis Khon Kaen/Thailand [158]
    Family: Blechnaceae
    Brainea B. insignis Yunnan/China [159]
    Family: Boraginaceae
    Eriodictyon E. tomentosum Placer Co./USA [160]
    Family: Fabaceae
    Adesmia A. grandiflora a) [161]
      A. trijuga    
      A. horrida    
      A. retrofracta    
    Ononis O. fruticosa Los Castanõs/Spain [162]
      O. natrix    
      O. rotundifolia a) [163]
    Trifolium T. pratense Trout Lake/USA [164]
    Family: Lamiaceae
    Leucosceptrum L. canum a) [165]
    Mentha M. pulegium Petite Kabylie/Algeria [166]
      M. suaveolens    
    Ocimum O. americanum RoyalBotanic Gardens, Kew/England [167]
    Otostegia O. fruticosa St. Catherine/Egypt [168]
    Salvia S. trilobu Marmara island/Turkey [169]
      S. hypoleuca Elbruz moun/Russia [170]
      S. pedicellata a) [171]
      S. yosgadensis Sultanhani/Turkey [172]
      S. plebeia a) [173]
      S. pilifera Berit Mount/Turkey [174]
      S. tomentosa Sofia/Bulgaria [175]
      S. argentea    
    Scutellaria S. polyodon a) [176]
      S. przewalskii Susamyr/Kyrgyzstan [177]
    Sideritis S. gomerae Canary islands/Spain [178]
    Teucrium T. chamaedrys Eskisehir/Turkey [179]
    Thymus T. longicaulis Sar planina/Macedonia [180]
      T. glabrescens Skopje/Macedonia  
    Family: Lythraceae
    Lawsonia L. inermis Thanjavur/India [148]
    Family: Nothofagaceae
    Nothofagus N. dombeyi Altos de Lircay/Chile [181]
    Family: Orobanchaceae
    Striga S. passargei a) [182]
      S. aspera a) [183]
    Family: Padaliacea
    Sesamum S. indicum Gambang/Malaysia [184]
    Family: Plantaginaceae
    Digitalis D. trojana Kizilcahamam, DemirkOy/Turkey [185]
      D. orientalis    
      D. lanata a) [186]
    Hebe H. cupressoides Dunedin/New Zealand [187]
    Veronica V. chamaedrys Rila Mount/Bulgaria [188]
    Veronicastrum V. latifolium Yongkang/China [189]
    Family: Portulacaceae
    Portulaca P. oleracea Tianjin/China [190]
    Family: Ranunculaceae
    Trollius T. chinensis Hebei/China [191]
    Family: Rosaceae
    Rosa R. damascena Plovdiv/Bulgaria [192]
      R. rugosa Botanischer Garten der TU Darmstadt/Germany [193]
    Family: Scrophulariaceae
    Buddleia B. macrostachya Sibsagar/India [194]
    Kickxia K. ramosissima Takht-e-Nusrati/Pakistan [195][196][197]
    Limnophila L. aromatica Ho Chi Minh/Vietnam [198]
    Linaria L. vulgaris Ukrania; China [67][199]
      L. reflexa Constantine/Algeria [72]
      L. kurdica Ukrania [199]
      L. scariosa Msila/Algeria [77]
    Family: Verbenaceae
    Clerodendrum C. siphonenthus Calcutta, Kalyani/India [200][201]
      C. phlomidis Pondicherry, Alanthurai/India [200][201][202][203][204][205]
      C. serratum Bhilai/India [206]
      C. inerme Pondicherry/India [207][208]
      C. neriifolium a) [209]
      C. indicum a)Khao Kho/Thailand [210][211]
    Duranta D. repens a) [212]
      D. plumieri a) [43][213]
    Lantana L. camara Taichung/Taiwan, Palampur/India, Karachi/Pakistan, Ceará state/Brazil, Manado/Indonesia, Okinawa/Japan [86][87][88][89][90][91]
    Lippia L. citriodora Athens/Greece [214]
    Family: Zosteraceae
    Phyllospadix P. japonica Omaezaki/Japan [215]
    1. a) not found.

    This entry is adapted from 10.3390/antibiotics9070417

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