FLAVONOIDS FROM ASTRAGALUS GENUS
HTML Full TextFLAVONOIDS FROM ASTRAGALUS GENUS
Dilip Gorai1, Shyamal K. Jash 2 and Rajiv Roy *3
Department of Chemistry 1, Bolpur College, Bolpur, Birbhum-731204, West Bengal, India
Department of Chemistry 2, Saldiha College, Saldiha, Bankura-722173, West Bengal, India
Independent researcher 3, Ph.D, Bhatgonna (Dignagar), Burdwan-713128, West Bengal, India
ABSTRACT: In this review our main focus is on flavonoid groups which are one of the main active constituents found with other active constituents like saponins and polysaccharides, while poisonous groups are nitro-compounds, indolizidine alkaloids and the seleniferous derivatives in Astragalus genus. It is well established fact that flavonoid possess many biological activity such as antiallergic, anti-inflammatory, antitumor, antiviral, antioxidant anticancer including anticarcinogenic and prodifferentiative activities. Many flavonoids, including those which are phytoalexins, provide plants with a defense against viral infections. The estrogenic action of many isoflavones is well known and mixtures of flavonoids are commonly used commercially to reduce capillary fragility. Astragalus root is a very old and well known drug in traditional Chinese medicine and have been used to improve resistance to infections and to aid in immunological disorders and viral infections, and also used as hepatoprotective, heart tonic, nephritis and diabetes. This review reports all flavonoids isolated till date which is nearly about 131 from 60 species of Astragalus genus; these flavonoid are further characterized and classified into flavones, flavonols, flavanones, flavan-4-ols, isoflavones, isoflavans, petrocarpans and miscellaneous
Keywords: |
Astragalus, Species, Flavonoids, Biological activity, Review
INTRODUCTION: Astragalus L. is the largest genus in the Legmninosae (Fabaceae) family and one of the largest genera of vascular plants on Earth, comprising ca. 2500 species of herbs or shrubs, mostly perennial, grouped into more than 100 subdivisions 1. Astragalus is cosmopolitan, distributed in cool, temperate, arid and semiarid continental region of South-Western Asia (the largest centre of distribution with 1000-1500 spp.), Sino-Himalayan region (500 spp.), Western-North and South America (with 400-450 and 100 spp., respectively), Europe, North Africa and Australia 2.
Astragalus plants are annual or perennial stemmed herbs or small shrubs (up to 150-200 cm), growing from underground roots. The leaves are alternate, imparipennate or paripennate, sometimes terminating in a spine. Flowers are leguminous, in racemic or axellary clusters, sessile or pedicellate. The fruit is a legume pod, usually dehiscent, with kidney shaped seeds 3.
In Western Asia A. gummifer is used as an emulsifier, stabilizer and thickening agent in pharmaceuticals and foodstuffs. A few species are edible (as raw and cooked roots of A. canadensis L., legumes of A. caryocarpus, seed of A. edulis, or leaves from A. glycyphyllos used as substitute for tea) 4, but a large number of Astragalus species are poisonous (e.g., A. mollissimus Torr.), especially for liverstock and wild animals. In many cases the toxins may be transferred to humans through meat or milk 5. Astragalus root is a very old and well known drug in traditional Chinese medicine and have been used to improve resistance to infections and to aid in immunological disorders and viral infections, and also used as hepatoprotective, heart tonic, nephritis and diabetes. Herbal practitioners may also suggest using this herb during treatment with chemotherapy as it stimulates the immune systems. The active constituents of Astragalus are saponins, flavonoids, and polysaccharides, while poisonous groups are nitro-compounds, indolizidine alkaloids and the seleniferous derivatives 6, 7.
In this review our main focus is on flavonoid groups which are one of the main active constituents found in Astragalus genus, because flavonoids possess many biological activity such as antiallergic, anti-inflammatory, antitumor, antiviral, antioxidant anticancer including anticarcinogenic and prodifferentiative activities. Many flavonoids, including those which are phytoalexins, provide plants with a defense against viral infections. The estrogenic action of many isoflavones is well known and mixtures of flavonoids are commonly used commercially to reduce capillary fragility 7a, 7b.
This review reports all flavonoid isolated till date which is nearly about 131 from 60 species of Astragalus genus, these flavonoid are further characterized and classified into flavones, flavonols, flavanones, flavan-4-ols, isoflavones, isoflavans, petrocarpans and miscellaneous.
MATERIALS AND METHODS:
The Flavonoid isolated and identified from Astragalus genus, were searched across the Medline (National Library of Medicine) and Science Direct databases, Pubmed, ACS, pols-one, Wiley chem. abstract, Springer link, RSC, Google and Google Scholar. The data were updated to 2015, using the search terms Astragalus Flavonoid, flavones, flavonols, flavanones, flavan-4-ols, isoflavones and petrocarpans from Astragalus genus, phytochemical, chemical constituents, from Astragalus as keywords. In addition, the reference lists of all papers identified were thoroughly reviewed.
RESULTS AND DISCUSSION:
List of Flavonoid(s) & their Structure(s) from Astragalus species: The purpose of this review is to present an overview of isolated flavonoids from species of Astragalus Genus, and there biological activity reported up to date 2015. This review reports 131 flavonoids from 60 species of Astragalus genus which are further characterized and classified into flavones (Table 2)-strc.no.1-18; flavonols (Table 3)-strc.no.19-77; flavanones (Table 4)-strc.no.78-81; flavan-4-ols (Table 5)-strc.no.82-83; isoflavones (Table 6)-strc.no.84-105; isoflavans (Table 7)-strc.no.106-118; petrocarpans (Table 8)-strc.no. 119-128 and miscelleneaous (Table 9)-strc.no.129-131. All of these are compiled in Table 1 and 2 and Fig. 1-7 8-103.
TABLE 1: LIST OF FLAVONOIDS ISOLATED
Compound name & Strc.no. | Plant species | Ref. |
Flavones | ||
Apigenin (1) | A. ammodendron Bunge
A. macropterum DC. A. floccosifolius Summ. A. tracicus Griseb. Astragalus spp. A. bombycinus A. verrucosus A. propinquus |
8
9 10 11 12 13,14 15,14 16,14 |
Apigenin 7-O-β-D-apio (1→2)-O-β-D-glc (2) | A. cicer L. | 17 |
Apigenin 7-O-β-D-glucopyranoside (3) | A. bombycinus | 13,14 |
Apigenin 7-O-gentobioside (4) | A. bombycinus | 13,14 |
Apigenin 7-O-β-D-rutinoside (5) | A. onobrychis L. | 18 |
Apigenin-8-C-glucoside (Vitexin) (6) | Astragalus spp.
A. corniculatus |
12
19,14 |
Baiealin (7) | A. membranaceus Bunge | 20 |
Cosmosiin (8) | A. ammodendron Bunge
A. caucasieus Pall. A. falcatus Lam. A. galegiformis L. A. kadshorensis Bunge A. maximus Willd. A. macropterum DC. |
8
21 21 21 21 21 9 |
Cynaroside (9) | Astragalus spp.
A. circassicus Grossh. |
12
22 |
Isovitexin (10) | Astragalus spp. | 12 |
Luteolin (11) | Astragalus spp.
A.quisqualis Bunge A.kabadianus Lipsky A.coluteocarpus Boiss. A.sinicus L. A. bombycinus A. propinquus |
12
23 24 25 26 13,14 16,14 |
Luteolin-8-C-glucoside [Orientin] (12) | Astragalus spp.
A. corniculatus |
12
19,14 |
Luteolin 7-O-β-D-glucopyranoside (13) | A. bombycinus | 13,14 |
Salvigenin (14) | A. propinquus | 16,14 |
Zapotinin (15) | A. adsurgens Pall. | 27 |
5,7,2'-Trihydroxyflavone (16) | A. cruciatus | 28,14 |
7-Hydroxyflavone (17) | A. microcephalus | 29,14 |
5,2',4'-Trihydroxy-flavone-8-C-L-arabino pyranoside-7-O-β-Dglucopyranoside (18) | A. bombycinus | 13,14 |
Flavonols | ||
[kaempferol 3-O-β-gal-3,4-di-(O-α-L-rha)] (19) | A. caucasicus Pall.
A. caucasieus Pall. A. falcatus Lam. A. kadshorensis Bunge A. maximus Willd. A. galegiformis L. |
30
21 21 21 21 21 |
Astragalin (20) | A. galegiformis L.
A. torrentum Bunge A. foccosifolius Summ. A. subrobustus A. bornmullerianus B. Fedtsch. A. dipelta A. capliosus Boriss. A. sevangensis Grossh. A. circassicus Gross. A. bungeanus A. goktschaicus A. arguricus Bunge A. lasioglottis M. Bieb. A. brachycarpus M. Bieb. A. polygala Pall. A. testiculatus Pall. A. caucasieus Pall. A. falcatus Lam. A. kadshorensis Bunge A. maximus Willd. A. galegifolius L. Astragalus spp. A. adsurgens Pall. A. karakuschensis Gontsch. A. aitosensis M.B. A. complanatus R.Br. A. asper A. hamosus |
21,32,31,14
33 10 34 35
36 37 22 22 22 22 22 38 39 39 40 21 21 21 21,41 41 12 27 42 43 44 45,14 46,14 |
Astragaloside (21) | A. torrentum Bunge
A. onobrychis L. A. brachycarpus M. Bieb. Astragalus spp. A. dasyanthus Pall. A. publiflorus DC. A. quisqualis Bunge A. novoasanicus Klokov |
33
18,38 39 12 47 48 49 50 |
Astrasikokioside I (kaempferol 3-O-α-L-rha (1 →6)-[α-L-rha(l→2)]-β-D-gal 7-O-α-L-rha (22) | A. cornplanatus R.Br. | 51 |
Cacticin (23) | A. kabadianus Lipsky
A. floccosifolius Summ |
24
10 |
Cannabiscitrin (24) | A. complanatus R.Br. | 52 |
Complanatin[rhamnocitrin 3-O-β-D-glc 4'-O-(3'-O-dihydrophaseoyl-)-β-D-glc) (25) | A. cornplanatus R.Br.
|
16 |
Complanatuside (26) | A. cornplanatus R.Br. | 16, 52 |
Dactilin (27) | A. galegformis L.
A. lasiogloftis M .Bieb. |
53
38 |
Flagaloside C (28) | A. galegiformis | 31,14 |
Flagaloside D (29) | A. galegiformis | 31,14 |
5,7,4'-trihydroxy-3,3'-dimethoxyflavone (30) | A. centralpinus Braun-
Blanquet |
49 |
Hyperin (Quercetin 3-O-β-D-gal) (31) | A. brachycarpus M. Bieb.
A. karakuschensrs Gontsch. A. subrobustus A. coluleocarpus Boiss. A. rnocroplerum DC. A. eupeplus Bameby A. babofagi Popov A. sevangensis Grossh. A. circassicus Grossh. A. bungeanus A. goktschaicus A. arguricus Bunge A. quisqualis Bunge A. corniculatus |
54, 55
42 34 25 9 56 57 22 22 22 22 22 23 19,14 |
lsoquereitrin (32) | A. membranaceus Bunge
A. karakuschensis Gontseh. A. onobrychis L. A. brachycarpus M. Bieb. A. adsurgens Pall. A. bornmullerianus B. Fedtseh. A. sevangensis Grossh. A. circassicus Grossh. A. bungeanus A. goktschaicus A. arguricus Bunge |
58
42 18,38 19 27 35
22 22 22 22 22 |
Isorhamnetin (33) | Astragalus spp.
A. austrosibirrcus Schischk A. mongholicus Bunge A. dasyanrhus Pall. A. membranaceus Bunge A. foccosfolius Summ. A. kabadianus Lipsky A. corniculatus A. hamosus |
59
60 61 47 45 10 24 19,14 46,14 |
Isorhamnetin 3-O-β-D-glc (34) | A. kabadianus Lipsky
A. adsurgens Pall. A. capriosus Boriss. A. jloccosrfolius Summ. A. cicer L. A. miser vat. Oblongfolius (Rydb.) Cronq. A. propinguus Schischkin A. pubfloms DC. A. karakuschensis Gontsch A. mongholrcus Bunge A. aitosensis M.B. |
24
62 37 10 17 63
64 65 42 66 43 |
Isorharnnetin 3,7-di-O-β-D-glc (35) | A. galegijomis L. | 53 |
Isorhamnetin 3-O-β-D-glc,7-O-α-rha (36) | A. adsurgens Pall.
A. austrosrbirrcus Schischk |
62
67 |
Kaempferide (37) | A. complanatus R.Br. | 44 |
Kaempferide 3-O-α-L-ara (38) | A. complanatus R.Br. | 44 |
Kaempferol (39) | A. macropterum DC.
A. babatagi Popov A. eupeplus Bameby A. torrenhrm Bunge A. floccosfolius Summ. A. quisqualis Bunge A. ausnosibrricus Schischk A. bachycarpus M. Bieb. Ashagalus spp. A. ammodendron Bunge A. onobrychis L. A. himaloyanus Klotz A. membranaceus Bunge A. kabadranus Lipky A. coluteocopus Boiss. A. subrobustus A. bornmullerianus B. Fedtsc A. corniculatus A. asper A. galegformis |
9
57 56 33 10 23 60 68 59 8 18 69 45 24 25 34 35 19,14 45,14 31,14 |
Kaempferol 3-O-β-xyl (40) | A. caucasieus Pall.
A. falcarus Lam. A. kadshorensis Bunge A. maximus Willd. A. galegformis L. |
21
21 21 21 21 |
Kaempferol 3,4'-di-O-β-glc (41) | A. complanatus R.Br. | 52 |
Kaempferol 3-O-β-xyl-(l→2)-O-β-D-glc (42) | A. complanatus R.Br. | 52 |
Kaempferol 3-O-α-A-rha-(l→2)-β-D-gal 7-O-α-A-rha (43) | A. shikokianus
|
51
|
Kaempferol 3-O-β-D-rutinoside7-O-α-L-rha (44) | A. cicer L. | 17 |
Kaempferol 3-O-β-D-apiof-(l→2)-β-D-glc; 4'-O-β-D-glc (45) | A. complanatus R.Br. | 52 |
Kaempferol 3-O-robinobioside (46) | A. verrucosus | 15,14 |
7-O-Methyl-kaempferol-4'-β-D-galactopyrano side (47) | A. hamosus | 46,14 |
Kumatakenin (48) | A. centralpinus Braun-
Blanquet |
49 |
Myricetin (49) | A. complanatus R.Br. | 52 |
Myricetin 3-O-β-D-glc (50) | A. complanatus R.Br. | 52 |
Myricetin 3-O-β-D-xyl-(l→2)-β-D-glc (51) | A. complanatus R.Br. | 52 |
Myricomplanoside (52) | A. complanatus R.Br. | 44 |
Narcissin (53) | A. torrenfum Bunge
A. centralpinus Braun- Blanquet A. daryanthus Pall. A. propinguus Schischkin A. galegformis L. A. maximus Willd. |
33
49
70 64 32 71 |
Neocomplanoside (54) | A. complanatus R.Br | 44 |
Nicotiflorin (55) | A. onobrychis L.
A. caucasieus Pall. A. falcam Lam. A. kadshorensis Bunge A. maximus Willd. A. galegformis L. A. ammodendmn Bunge A. adsurgens Pall. |
18
21 21 21 21 21 8 62 |
Populnin (56) | A. dipelta
A. floccosfolius Summ. A. polygola Pall. |
36
10 39 |
Quercetin (57) | A. macroprerum DC.
A. babatagi Popov A. eupeplus Bameby A. torrenfum Bunge A. captiosus Boriss. A. guisqualis Bunge A. bachycarpus M. Bieb. Astragalus spp. A. mongholicus Bunge A. onobrychis L. A. himaloyonus Klotz A. membranaceus Bunge A. kabadianus Lipsky A. coluteocarps Boiss. A. subrobusrus A. bornmullerianus B. Fedtasch A. asper A. corniculatus |
9
57 56 33 37 23 68 59 61 18 69 45 24 25 34 35
19,14 45,14 |
Quercetin 3-O-robinobioside (58) | A. capriosus Boriss | 72 |
Quercetin 3-O-rob 7-O-α-L-rha (Clovin) (59) | A. shikokianus | 51 |
Quercetin-3-O-β-D-glucopyranoside (60) | A. corniculatus
A. asper |
19,14
45,14 |
Quercetin-3,7-di-β-D-glucopyranoside-4'-O-α-L-rhamnopyranoside (61) | A. bombycinus | 13,14 |
Quercetin-3,7-di-O-β-D-glucopyranoside (62) | A. bombycinus | 13,14 |
Quercetin 3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside (63) | A. bombycinus | 13,14 |
Quercitrin (64) | A. floccosfolius Summ.
A. sewngensis Grossh. A. circassicus Grossh. A. Bungeanus A. gokfschaicus A. arguricus Bunge A. babatagi Popov A. bornmullerranus B. Fedtsch. |
10
22 22 22 22 22 57 35 |
Quercimeritrin (65) | A. asper | 45,14 |
Rhamnetin (66) | A. floccosfolius Summ. | 10
|
Rhamnetin 3-O-β-D-gal (67) | A. floccoslfolius Summ. | 10
|
Rhamnocitrin (68) | A. mongholicus Bunge
|
61
|
Rhamnocitrin 3-O-β-D-glc (69) | A. complanatus R.Br
A. membranaceus Bunge |
44,73 58,74 |
Rhamnocitrin 3-O-β-D-apiof-(1→2)-PD-glc (70) | A. complanatus R.Br | 52 |
Rhamnocitrin 3-O-β-D-apiof-(1→2)-β-D-glc-4’O-β-D-glc (71) | A. complanatus R.Br | 52 |
Rhamnoeitrin-3-O-(5-O-p-coumaroyl-β-D-apiof-(1→2)-β-D-glc) (72) | A. complanatus R.Br | 75 |
Rhamnocitrin 3-O-(5'-O-feruloyl-β-D-apiof-(1→2)-β-D-glc) (73) | A. complanatus R.Br | 75 |
Robinin (74) | A. caucasieus Pall.
A. falcatus Lam. A. kadshorensis Bunge A. maximus Willd. A. galegformis L. A. shikokianus |
21
21 21 21 21 51 |
Rutin (Quercetin 3-rutinoside) (75) | A. macroprerum M3.
A. eupeplus Bameby A. babatagi Popov A. torrentum Bunge A. jloccosfolius Summ. A. quisqualis Bunge A. onobrychis L. A. himalayanus Klotz A. kabadianus Lipsky A. coluteocarpus Boiss. A. bornmullerianus B. Fedtsch. A. sevangensis Grossh. A. circassicus Grossh. A. bungeanus A. goktschaicus A. arguricus Bunge A. captiosus Boriss. A. adrurgem Pall. A. iasioglo Mis.Bieb. A. aitosensis M.B. A. propinpus Schischkin A. asper A. cruciatus A. verrucosus |
9
56 57 33 10 23 18 69 24 25 35
22 22 22 22 22 37 27 38 43 64 45,14 28,14 15,14 |
Tamarixin (76) | A. mongholicus Bunge | 66 |
Trifolin (77) | A. brachycarpus M. Bieb.
A. caucasieus Pall. A. falcatus Lam. A. kadshorensis Bunge A. maximus Willd. A. galegfiolius L. A. subrobustus A. dipelta A. sevangensis Grossh. A. circassicus Grossh. A. bungeanus A. goklschaicus A. arguricus Bunge A. torrentum Bunge A. adrurgens Pall. |
68
21 21 21 21,41 21 34 36 22 22 22 22 22 33 62 |
Flavanones | ||
3',7-dihydroxyflavanone (78) | A. centralpinus Braun-
Blanquet |
49 |
Naringenin (79) | A. sinicus L. | 26 |
Eriodyctiol-7-O-glucoside (80) | A. corniculatus | 19,14 |
Liquiritigenin (81) | A. membranaceus | 76,14 |
Flavan-4-ol | ||
4',5-dimethoxy-7-hydroxyflavan-4-o1 (82) | A. centralpinus Braun-
Blanquet |
49 |
(3R,4R)-3-(2-Hydroxy-3,4-dimethoxyphenyl )-chroman-4,7-diol-7-O-β-D glucopyranoside (83) | A. membranaceus | 44,14 |
Isoflavones | ||
Acicerone (84) | A. cicer L. | 77,78,79 |
Afrorrmosin (85) | A. membranaceus Bunge | 27 |
Ammopiptanoside A (86) | A. membranaceus | 80,14 |
Biochanin A (87) | A. cicer L. | 78 |
Calycosin (88) | A. membranaceus Bunge
A. mongholicus A. cicer L. A. complanatus R.Br. |
81,20,82,83,84,85
52,14 78 52 |
Calycosin 7-O-β- glucoside (89) | A. complanatus R.Br.
A. membranaceus Bunge |
52,73
86,20,87 |
Calycosin 7-O-β-D-{6''-[(E)-but-2-enoyl]}-glucoside (90) | A. membracaceus | 80,14 |
Calycosin 7-O-β-D-(6''-acetyl)-glucoside (91) | A. membracaceus | 80,14 |
Cajanin (92) | A. cicer L. | 77,78,79 |
Daidzein (93) | A. sinicus L.
A. bombycinus A. verrucosus |
26
88 15 |
7,3'-dihydroxy-8,4'-dimethoxyisoflavone (94) | A. membranaceus Bunge | 20 |
8,3'-dihydroxy-7,4'-dimethoxyisoflavone (95) | A. membranaceus Bunge | 20,85 |
Formononetin (96) | A. membranaceus Bunge
A. mongholicus A. cicer L. A. clusii Boiss. |
81,20,21,83,89,90,85
52 78 91 |
Odoration (97) | A. membranaceus Bunge | 81 |
Odoration 7-O-β-glc (98) | A. membranaceus Bunge
A. mongholicus |
20
52 |
Ononin (99) | A. complanatus R.Br.
A. membracaceus A. verrucosus A. microcephalus A. mongholicus A. membranaceus |
52,73
80,14 15,14 92,14 93,14 44,14 |
Pratensein (100) | A. verrucosus
A. membranaceus var. mongholicus |
15,14
94,14
|
Pratensein 7-O-β-D-glucopyranoside (101) | A. membranaceus
var. mongholicus |
94,14 |
Pseudobaptigenin (102) | A. cicer L. | 78 |
6ꞌꞌ-Acetylononin (103) | A. membranaceus | 80,14 |
7,5'-Dihydroxy-3'-methoxy-isoflavone-7-O-β-D-glucopyranoside (104) | A. membranaceus
var. mongholicus |
94,14 |
7-Hydroxy-3',5'-dimethoxyisoflavone (105) | A. peregrinus | 95,14 |
Isoflavans | ||
Astraeiecran (106) | A. cicer L. | 96,77,78,79 |
(3R)·8,2'-dihydroxy-7,4'-dimethoxy isoflavane (107) | A. membranaceus Bunge | 97,85 |
2'-hydroxy-5' ,6'-dimethoxy- 7-O-,8-D-glc (108) | A. membranaceus Bunge | 83 |
Isomucronulatol (109) | A. mongholicus Bunge
A. membracaceus |
98
80,14 |
Isomucronulatol 7-O-β-D-glc (110) | A. cicer L.
A. membracaceus |
96
80,14 |
Isomucronulatol 5'-hydroxy-2',5'-di-O-β-D-glc (111) | A. membranaceus Bunge
A. mongholicus Bunge |
99,85
98 |
lsomueronulatol 7,2'-di- O-β-glc (112) | A. mongholicus Bunge | 98 |
(3R)-7,2',3'-trihydroxy-4'-methoxyiso flavane (113) | A. membranaceus Bunge | 97 |
(R)-3-(5-Hydroxy-2,3,4-trimethoxyphenyl)-chroman-7-ol (114) | A. membranaceus | 80,14 |
7-O-methylisomueronulatol (115) | A. membranaceus Bunge
A. mongholicus Bunge |
100
98 |
(3S)-8-methoxyvestitol (116) | A. alexadrinus Boiss.
A. trigonus DC. |
101
101 |
Mucronulatol (117) | A. cicer L.
A. adsurgens Pall. |
96,77,78,79
27 |
Spherosin (118) | A. orbiculatus Ledeb.
A. alexadrinus Boiss. A. trigonus DC. |
102
101 101 |
Pterocarpans | ||
Maackiain (119) | A. cicer L.
A. membranaceus Bunge A. mongholicus Bunge A. trojanus Stev. |
77,78,79
77,78,79 77,78,79 77,78,79 |
Medicarpin (120) | A. cicer L. | 78 |
(6aR, l laR)-10-hydroxy-3,9,10 dimeth oxypterocarpan (121) | A. membranaceus Bunge | 100 |
(6aR, l laR)- 3,9,10-trimethoxypterocarpan (122) | A.membranaceus Bunge
A.mongholicus Bunge |
98
100 |
(–)-Methylinissolin 3-O-β-D-(6'-acetyl)glucoside (123) | A. membranaceus | 80,14 |
(–)-Methylinissolin 3-O-β-D-{6'-[(E)-but-2-enoyl]}-glucoside (124) | A. membranaceus | 80,14 |
(–)-Methylinissolin 3-O-β-D-glucoside (125) | A. membranaceus | 80,14 |
Licoagroside D (126) | A. membranaceus | 80,14 |
Vesticarpan (127) | A. membranaceus | 80,14 |
(–)-Methylinissolin (128) | A. membranaceus | 80,14 |
Miscelleneaous | ||
Sulfuretin (129) | A. microcephalus | 29,14 |
Isoliquiritigenin (130) | A. membranaceus | 76,14 |
Pendulone (131) | A. membranaceus | 80,14,103 |
TABLE 2: LIST OF ASTRAGALUS SPECIES FROM WHERE FLAVONOIDS WERE ISOLATED
Astragalus Species | ||
A. adsurgens Pall. | A. corniculatus | A. miser Hook. |
A. aitosensis M.B. | A. cruciatus | A. mongholicus Bunge |
A. alexadrinus Boiss. | A. dasyanthus Pall. | A. mongholicus Bunge |
A. ammodendron Bunge | A. dipelta Bunge | A. novasanicus Klokov |
A. arguricus Bunge | A. eupeplus Bameby | A. onobrychis L. |
A. asper | A. falcatus Lam. | A. orbiculatus Ledeb. |
A. austrosibiricus Schischk | A. floccosifolius Sumn. | A. polygala Pall. |
A. babatagi Popov | A. galegiformis L. | A. propinquus Schischkin |
A. bachycarpus M. Bieb. | A. goktschaicus | A. pubiflorus DC. |
A. bombycinus | A. himalayanus Klotz | A. quisqualis Bunge |
A. bommuellerianus B. Fedtsch. | A. hamosus | A. sevangensis Grossh. |
A. bungeanus Boiss. | A. kabadianus Lipsky | A. shikokianus |
A. captiosus Boriss. | A. kadshorensis Bunge | A. sinicus L. |
A. caucasicus Pall. | A. karakuschensis Gontsch. | A. subrobustus |
A. centralpinus Braun-Blanquet | A. lasioglottis M. Bieb. | A. testiculars Pall. |
A. cicer L. | A. macropterum DC. | A. torrentumi Bunge |
A. circassicus Grossh. | A. maximus Willd. | A. tracicus |
A. clusii Boiss. | A. membranaceus Bunge | A. trigonus DC. |
A. coluteocarpus Boiss. | A. membranaceus Bunge | A. verrucosus |
A. complanatus R.Br. | A. microcephalus | Astragalus spp. |
Structures of flavonoids isolated:
FIG.1: FLAVONES (STRC.NO.1-18)
FIG.2: FLAVONOLS (STRC.NO.19-77)
FIG.3: FLAVANONES & FLAVAN-4-OL (STRC.NO.77-83)
FIG.4: ISOFLAVONES (STRC.NO.84-105)
FIG.5: ISOFLAVANS (STRC.NO.106-118)
FIG.6: PTEROCARPANS (STRC.NO.119-128)
FIG.7: MISCELLENEAOUS (STRC.NO.129-131)
Biological Activities of the Astragalus Genus:
Flavonoids from Astragalus spp. show a significant antiexudative effect 104, while flavonoid complex from A.centralpinus possess a marked spasmolitic action and account for a moderate, but long-standing reduction of the arterial pressure. The total flavonoids content from A. lasioglottis show a high biological activity decreasing the cholesterol and triglyceride levels in animals with experimental hyperlipidemia 105. Isoflavonoids are best known for being estrogenic, antimicrobial or insecticidal 106. They are involved with diverse biological activities, including disease resistance, and, potentially, photosensibilization 78. Calycosin 88, and formononetin 96, as isoflavones isolated from the roots of A. membranaceus, inhibit lecithin peroxidation which was induced both by hydroxy radical generation by interation of haemoglobin and hydrogen peroxide and by superoxide anion generation by xanthine/xanthine oxidase 83, 82.
Afrorrmosin 85, calycosin 88 and odoratin 96, isolated from the same source have antioxidative activity and prevent lipid peroxidation (all the tested isoflavones have a methoxy group at 4' position) 81. Other isoflavonoids do not show inhibitory effects on lecithin peroxidations. These results demonstrated that hydroxyl group at the 7 and 3' positions on isoflavones, which have a methoxy group on the C-4', are necessary for the antioxidant properties, because isoflavones which have a methoxyl group at the 6 and 4' positions, have no inibitory effects on LPOs 82.
On the other hand, the experimental data showed that the total flavonoids of Astragalus and calycosin 88 could inhibit the proliferation of K562 cells 107. The total flavonoids of A. mongholicus are the active components, which benefit cardiovascular disease attributed to the potent antioxidant activity in improving the atherosclerosis profile 108. Isoflavones, calycosin 88, and formononetin 96, from the Astragalus root, could promote dimethyl arginine dimethylaminohydrolase-2 protein and mRNA expressions in Madin Darby Canine Kidney (MDCK) II cells, and up regulate the neuronal nitric oxide synthase levels 109. Calycosin-7-O-β-D-glucoside 89, from A. membranaceus showed anti-lipid peroxidative activities 110.
CONCLUSION: The present review deals with up to date literature on flavonoids isolated from Astragalus genus as well as different biological activities exhibited by the isolated flavonoid constituents. We are quite optimistic that this review article will surely stimulate present day researcher to undertake more systematic research work on this important genus for isolation of flavonoids so as to discover other significant more biological activities of the plants.
CONFLICT OF INTEREST: The authors declare no conflict of interest.
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How to cite this article:
Gorai D, Jash SK and Roy R: Flavonoids from Astragalus Genus. Int J Pharm Sci Res 2016; 7(7): 2732-47.doi: 10.13040/IJPSR.0975-8232.7(7).2732-47.
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2732-47
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English
IJPSR
Dilip Gorai, Shyamal K. Jash and Rajiv Roy *
Department of Chemistry, Bolpur College, Bolpur, Birbhum, West Bengal, India
royrajiv35@gmail.com
10 February, 2016
02 April, 2016
26 May, 2016
10.13040/IJPSR.0975-8232.7(7).2732-47
01 July 2016