Pectolinarin and Pectolinarigenin: Comparison
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Please note this is a comparison between Version 2 by Felix Wu and Version 1 by thamere cheriet.

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

[12][13]

[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]

[14][15]

[6][15][16][17][18][19][7,16–20]

 

 

 

[18]

]

[21]

[18]

[

[19]

20

]

[21]

[19,22]

[19,23–26]

[

17

[

18

]

[19]

[18][21][19,22]

[18][22][23][24][25][19,23–26]

 

 

 

 

[19]

[19,26,27]

[

18

]

[19]

[

18

]

[

25

]

[

26

]

[19,26,27]

 

[28,29]

[

27

]

[

28

]

[28,29]

 

[30]

[

29

]

[30]

 

 

[30–32]

[

29

]

[

30

]

[

31

]

[30–32]

 

[16]

[

15

]

[16]

 

 

 

 

 

 

 

 

[33,34]

[

32

]

[

33

]

[33,34]

 

[17,31,35–37]

[

16

]

[

30

]

[

34

]

[

35

]

[

36

]

[17,31,35–37]

 

 

 

 

 

[35]

[

34

]

[35]

 

[38]

[34]

[39]

[16,40,41]

[

37

]

[38]

[

33

]

[34]

[

38

]

[39]

[

15

]

[

39

]

[

40

]

[16,40,41]

 

 

 

[41]

[35]

[34,40]

[

40

]

[41]

[

34

]

[35]

[

33

]

[

39

]

[34,40]

 

[42]

[43]

[

41

]

[42]

[

42

]

[43]

Duranta

D. plumieri

Rajshahi/Bangladesh

[44]

[43][44]

Hemistepta

H. lyrata

Kangwon/S. Korea

[45]

[44][45]

Picnomon

P. acarna

Mount Hortiatis/Greece

[46]

[45][46]

Family: Bignoniaceae

Distictella

D. elongata

Minas Gerais State/Brazil

[47]

[46][47]

Markhamia

M. lutea

Benguluru/India

[48]

[47][48]

Family: Buddlejaceae

Buddleja

B. officinalis

Anhui/China

[49]

[48][49]

Family: Ericaceae

Rhododendron

R. arboreum

Aligarh/India

[50]

[49][50]

Family: Gesneriaceae

Corallodiscus

C. flabellate

Kunming/China

[51]

[50][51]

Aeschynanthus

A. moningeriae

Jinhua/China

[52]

[51][52]

Family: Lamiaceae

Leucosceptrum

L. canum

Tibet/China

[53]

[52][53]

Teucrium

T. hyrcanicum

Sicily/Italy

[54]

[53][54]

Family: Lythraceae

Lawsonia

L. inermis

Thanjavur/India

[55]

[54][55]

Family: Moraceae

Clerodedrum

C. phlomides

Tamil Nadu/India

[56]

[55][56]

Family: Orchidaceae

Oncidium

O. baueri

Londrina/Brazil

[57,58]

[56][57][57,58]

Family: Orobanchaceae

Melampyrum

M. roseum

Suwon/S. Korea

[59]

[58][59]

Family: Plantaginaceae

Scoparia

S. dulcis

Nanning/China

[60]

[59][60]

Family: Poaceae

Oryza

O. sativa

a)

[61]

[60][61]

Family: Ranunculaceae

Trollius

T. ledebourii

Hebei/China

[62]

[61][62]

Family: Rosaceae

Kerria

K. japonica var.

Chongqing/China

[63]

[62][63]

Crataegus

C. laevigata

Bremen/Germany

[64]

[63][64]

Family: Santalaceae

Thesium

T. chinense

Anhui/China

[65]

[64][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]

[2][65][66][67][2,66–68]

 

 

[69–71]

[

68

][69][70][69–71]

 

[72–75]

[

71

]

[

72][73][74][72–75]

 

[66]

[

65

]

[66]

 

 

[76]

[

75

]

[76]

 

[77]

[67]

[

76

]

[77]

[

66

]

[67]

 

 

L. scariosa

Msila/Algeria

[78]

[77][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]

[79]

[79][80][81,82]

[83]

[78

[80][81][81,82]

[82][83]

 

[84]

[

83

]

[84]

 

[85]

[

84

]

[85]

Family: Verbenaceae

Morus

M. alba L.

Hongseong/Korea

[86]

[85][86]

Lantana L. camara

Taichung/Taiwan, Palampur/India, Karachi/Pakistan, Ceará state/Brazil, Manado/Indonesia, Okinawa/Japan

[87–92]

[86][87][88][89][90][91][87–92]

Lippia L. rubella

Minas Gerais/Brazil

[93]

[92][93]

Family: Winteraceae

Tasmannia

T. lanceolata

Go Wild Harvest/Australia

[94]

[93][94]

a Not found.

Pectolinarigenin is the aglycone part of pectolinarin, which is obtained by hydrolysis reaction [72][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]

[94][99]

Family: Aspleniaceae

Asplenium

A. glaucophyllum

West Malysia

[100]

[95][100]

 

A. normale

West Malaysia

[101]

[96][101]

Family: Asteraceae

Achillea

A. collina

wet lowland

meadows/UK

[102]

[97][102]

 

A. asplenifolia

 

 

Ajania

A. potaninii

Gansu/China

[103]

[98][103]

Ambrosia

A. camphorate

Baja California/Mexico

[104]

[99][104]

Arnica

A. angustifolia

northwest

Canada and Alaska

[105]

[100][105]

 

A. Montana

California/USA

[106]

[101][106]

 

A. chamissonis

Graines Voltz/France

[107]

[102][107]

 

A. montana

Šumava Mounts/Czech

[108]

[103][108]

Artemisia

A. mongolica

Gansu/China

[109]

[104][109]

 

A. judaica

St. Catherine, Sinai/Egypt

[110]

[105][110]

 

A. monosperma

Cairo/Egypt

 

 

A. herba-alba

Mount Moses/Egypt

 

 

A. xerophytica

South Gobi Aimak/Mongolia

[111]

[106][111]

 

A. glabella

Karaganda/Kazakhstan

[112]

[107][112]

 

A. vestita

Lhasa/Tibet

[113]

[108][113]

Baccharis

B. trinervis

Costa Rica

[114]

[109][114]

 

B. decussata

Venezuela

[115]

[110][115]

 

B. concave

 

[116]

[111][116]

 

B. uncinella

Campos do Jordão/Brazil

[117]

[112][117]

 

B. conferta

Veracruz/Mexico

[118]

[113][118]

Centaurea

C. alexandrina

Alexandria/Egypt

[119]

[114][119]

 

C. aspera

Ribera Baixa/Spain

[120]

[115][120]

 

C. cariensis

 

[121]

[116][121]

 

C. collina

Valencia/Spain

[122]

[117][122]

 

C. sadleriana

Jakabszállás/Hungary

[123]

[118][123]

 

C. moesiaca

Malashevska planina/Bulgaria

[124]

[119][124]

 

C. behen

Iran

[125]

[120][125]

Chromolaena

C. odorata

Chonburi/Thailand

[126]

[121][126]

Chrysanthemum

C. pacificum

Tsukuba/Japan

27

[26][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]

[18][23][24][25][26][27][122][19,24–28,127]

 

C. chanroenicum

Daejeon, Ulsan, Sancheong/S. Korea

[26,128]

[25][123][26,128]

 

C. japonicum

Jiang Xi/China

[129]

[124][129]

 

C. arvense

Musa Khel Bannu/Pakistan

[130]

[125][130]

 

C. nipponicum

Suwon/S. Korea

[131]

[126][131]

 

C. rhinoceros

 

[132]

[127][132]

Dichrocephala

D. integrifolia

Shanghai/China

[133]

[128][133]

Dugaldia

D. pinetorum

Nuevo Lebn/Mexico

[134]

[129][134]

Eriocephalus

E. giessii

Aus-Koppies/Namibia

[135]

[130][135]

Eupatorium

E. cannabinum

Gronigen/Netherlands

[136]

[131][136]

 

E. odoratum

Kuala Pilah/Malaysia

[137,138]

[132][133][137,138]

 

E. semiserratum

Arkansas/USA

[139]

[134][139]

Fragrant

F. Eupatorium

Guangxi/China

[140]

[135][140]

Grindelia

G. glutinosa

Poconchile, Valle de

Liuta, Tarapaca/Chile

[141]

[136][141]

Gutierrezia

G. mandonii

Salta/Argentina

[142]

[137][142]

Helenium

H. integrifolium

 

[143]

[138][143]

Heterotheca

H. latifolia

San Luis/Argentina

[144]

[139][144]

Hemistepta

H. lyrata

Kangwon/S. Korea

[45]

[44][45]

Hymenoxys

H. jamesii

Coconino/USA

[145]

[140][145]

Iva

I. nevadensis

Tonopah/USA

[146]

[141][146]

 

I. frutescens

Franklin/USA

[147]

[142][147]

Jungia

J. polita

San Martin/Argentina

[148]

[143][148]

Olearia

O. paniculata

Dunedin/New Zealand

[149]

[144][149]

Onopordon

O. corymbosum

Barracas, Castellon/Spain

[150]

[145][150]

 

O. nervosum

a)

[151]

[146][151]

Santolina

S. chamaecyparissus

Lyon/France

[152]

[147][152]

 

S. pinnata

Pisa/Italy

[153]

[148][153]

Saussurea

S. elegans

Murghab/Tajikistan

[154]

[149][154]

Schkuhria

S. pinnata

Cordoba/Argentina

[155]

[150][155]

Seriphidium

S. santolium

Xinjiang Uigour/China

[156]

[151][156]

Stevia

S. laxiflora

Cuernavaca, Morelos/Mexico

[157]

[152][157]

Vernonia

V. cinerea

Pahang/Malaysia

[158]

[153][158]

Family: Betulaceae

Alnus

A. glutinosa

Darmstadt/Germany

[159]

[154][159]

 

A. japonica

 

[160]

[155][160]

Betula

B. ermanii

 

[159]

[154][159]

 

B. verrucosa

a)

[161]

[156][161]

 

B. pubescens

Biebrza/Poland

[162]

[157][162]

 

B. pendula

 

 

Family: Bignoniaceae

Millingtonia

M. hortensis

Khon Kaen/Thailand

[163]

[158][163]

Family: Blechnaceae

Brainea

B. insignis

Yunnan/China

[164]

[159][164]

Family: Boraginaceae

Eriodictyon

E. tomentosum

Placer Co./USA

[165]

[160][165]

Family: Fabaceae

Adesmia

A. grandiflora

a)

[166]

[161][166]

 

A. trijuga

 

 

 

A. horrida

 

 

 

A. retrofracta

 

 

Ononis

O. fruticosa

Los Castanõs/Spain

[167]

[97][167]

 

O. natrix

 

 

 

O. rotundifolia

a)

[168]

[162][168]

Trifolium

T. pratense

Trout Lake/USA

[169]

[163][169]

Family: Lamiaceae

Leucosceptrum

L. canum

a)

[170]

[164][170]

Mentha

M. pulegium

Petite Kabylie/Algeria

[171]

[165][171]

 

M. suaveolens

 

 

Ocimum

O. americanum

Royal

Botanic Gardens, Kew/England

[172]

[166][172]

Otostegia

O. fruticosa

St. Catherine/Egypt

[173]

[167][173]

Salvia

S. trilobu

Marmara island/Turkey

[174]

[168][174]

 

S. hypoleuca

Elbruz moun/Russia

[175]

[169][175]

 

S. pedicellata

a)

[176]

[170][176]

 

S. yosgadensis

Sultanhani/Turkey

[177]

[171][177]

 

S. plebeia

a)

[178]

[172][178]

 

S. pilifera

Berit Mount/Turkey

[179]

[173][179]

 

S. tomentosa

Sofia/Bulgaria

[180]

[174][180]

 

S. argentea

 

 

Scutellaria

S. polyodon

a)

[181]

[175][181]

 

S. przewalskii

Susamyr/Kyrgyzstan

[182]

[176][182]

Sideritis

S. gomerae

Canary islands/Spain

[183]

[177][183]

Teucrium

T. chamaedrys

Eskisehir/Turkey

[184]

[178][184]

Thymus

T. longicaulis

Sar planina/Macedonia

[185]

[179][185]

 

T. glabrescens

Skopje/Macedonia

 

Family: Lythraceae

Lawsonia

L. inermis

Thanjavur/India

[153]

[148][153]

Family: Nothofagaceae

Nothofagus

N. dombeyi

Altos de Lircay/Chile

[186]

[180][186]

Family: Orobanchaceae

Striga

S. passargei

a)

[187]

[181][187]

 

S. aspera

a)

[188]

[182][188]

Family: Padaliacea

Sesamum

S. indicum

Gambang/Malaysia

[189]

[183][189]

Family: Plantaginaceae

Digitalis

D. trojana

Kizilcahamam, DemirkOy/Turkey

[190]

[180][190]

 

D. orientalis

 

 

 

D. lanata

a)

[191]

[184][191]

Hebe

H. cupressoides

Dunedin/New Zealand

[192]

[185][192]

Veronica

V. chamaedrys

Rila Mount/Bulgaria

[193]

[186][193]

Veronicastrum

V. latifolium

Yongkang/China

[194]

[187][194]

Family: Portulacaceae

Portulaca

P. oleracea

Tianjin/China

[195]

[188][195]

Family: Ranunculaceae

Trollius

T. chinensis

Hebei/China

[196]

[189][196]

Family: Rosaceae

Rosa

R. damascena

Plovdiv/Bulgaria

[197]

[190][197]

 

R. rugosa

Botanischer Garten der TU Darmstadt/Germany

[198]

[191][198]

Family: Scrophulariaceae

Buddleia

B. macrostachya

Sibsagar/India

[199]

[192][199]

Kickxia

K. ramosissima

Takht-e-Nusrati/Pakistan

[200–202]

[193][194][195][200–202]

Limnophila

L. aromatica

Ho Chi Minh/Vietnam

[203]

[196][203]

Linaria

L. vulgaris

Ukrania; China

[68,204]

[67][197][68,204]

 

L. reflexa

Constantine/Algeria

[73]

[72][73]

 

L. kurdica

Ukrania

[204]

[197][204]

 

L. scariosa

Msila/Algeria

[78]

[77][78]

Family: Verbenaceae

Clerodendrum

C. siphonenthus

Calcutta, Kalyani/India

[205,206]

[198][199][205,206]

 

C. phlomidis

Pondicherry, Alanthurai/India

[205–210]

[198][199][200][201][202][203][205–210]

 

C. serratum

Bhilai/India

[211]

[204][211]

 

C. inerme

Pondicherry/India

[212,213]

[205][206][212,213]

 

C. neriifolium

a)

[214]

[207][214]

 

C. indicum

a)Khao Kho/Thailand

[215,216]

[208][215,216]

Duranta

D. repens

a)

[217]

[209][217]

 

D. plumieri

a)

[44,218]

[43][210][44,218]

Lantana

L. camara

Taichung/Taiwan, Palampur/India, Karachi/Pakistan, Ceará state/Brazil, Manado/Indonesia, Okinawa/Japan

[87–92]

[86][87][88][89][90][91][87–92]

Lippia

L. citriodora

Athens/Greece

[219]

[211][219]

Family: Zosteraceae

Phyllospadix

P. japonica

Omaezaki/Japan

[220]

[212][220]
  1. a) not found.

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