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.
REFERENCES:
- Boissier E. Flora Orientalis 1872; 2: 316.
- Pignatti S. In Flora d'ltalia, Edagricole Ed.: Bologna 1982, Vol. 1 pp 650-662.
- Tutin TG., Heywood VH., Burges NA., Mooze DM., Valeutine DH., Walters SM., Webb DA. In Flora Europea, Cambridge Univ Press: Cambridge 1972; 2: 108-124.
- Motta F. In Nel mondodel la Natura-Enciclopedia di Scienze Natural i, Motta F Ed., 1962; 222-224.
- Rios JL., Waterman PG. Phytoterapy Research 1997; 77: 411-418.
- Tang W Eisenbrand G. Chinese Drugs of Plant Origin Springer-Verlag: Berlin 1992.
- Southom IW. In Phytochemical Dictionary of the Leguminosae, Bisby FA., Buckingam J., Harbone JB. Eds, Chapman & Hall: London 1994; 87-107.
7a Mabry TJ., Ulebelen A. Journal of Agricultural Food Chemistry 1980; 28: 188-195.
7b Middleton EJ. International Journal Pharmacognosy 1996; 34: 344-348.
- Khozhambergenova P., Blinova KF. Khim Prir Soedin 1980; 4: 566-567.
- Yasinov RK. Khim Prir Soedin 1986; 4: 513-514.
- Yasinov RK., Syrovezhko NV., Yakovlev GP., Ovcharenko SN. Khim Prir Soedin 1984; 4: 523-524.
- Ionkova I., Nikolov S., Panova D. Probl Farm 1984; 12: 43-47.
- Krivenchuk PE., Litvinenko VI., Maksyutina NP Deryugina LI., Tikhonov AI Darmograi VN. Fenol'nye Soedin Ikh Biol Funkts Mater Vses Simp 1st 1966; 104-108.
- Ibrahim LF., Marzouk MM., Hussein SR., Kawashty SA., Mahmoud K., Saleh NAM. Flavonoid constituents and biological screening of Astragalus bombycinus Boiss Natural Product Research 2013; 27: 386-393.
- Xiaoxia Li Lu Qu Yongzhe Dong Lifeng Han Erwei Liu Shiming Fang Yi Zhang Tao Wang A Review of Recent Research Progress on the Astragalus Genus Molecules 2014; 19: 18850-18880.
- Pistelli L., Giachi I., Lepori E., Bertoli A Further saponins and flavonoids from Astragalus verrucosus Moris Pharm Biol 2003; 41: 568-572.
- Chaturvedula VSP., Prakash I. Flavonoids from Astragalus propinquus Journal of Chemical Pharmaceutical Research 2013; 5: 261-265.
- Alaniya MD., Aneli DN., Paudin AV., Komelin RV., Khim Prir Soedin 1983; 4: 528.
- Benbassat N., Nikolov St. Planta Medica 1995; 61: 100.
- Krasteva I., Nikolov S. Flavonoids in Astragalus corniculatus Quimica Nova 2008; 31: 59-60
- Song C., Zheng Z., Liu D., Hu Z., Sheng W. Zhiwu Xuebao 1997; 39: 764-768.
- Alaniya MD., Komissarenko NF., Kemertelidze EP. Izv Akad Nauk Gruz SSR Ser Khim 1976; 2: 31-38.
- Guzhva NN., Luk'yanchikova MS., Kazarov AL. Khim Prir Soedin 1985; i: 411-412.
- Yasinov RK., Syrovekhko NV., Yakovlev GP. Khim Prir Soedin 1983; i: 387-388.
- Yasinov RK., Khaitov IKh. Khim Prir Soedin 1988; 5: 450-451.
- Yasinov RK., Aripova ZT. Khim Prir Soedin 1987; i: 454-455.
- Gao B-L., Lou W-J., Chen Y-X., Fan Q-S., Cao C-J., Shen S-S., Jin R-Z. Zhiwu Shengli Xuebao 1998; 24: 220-224.
- Sun L., Zheng S., Shen X. Xibei Shifan Daxue Xuebao Ziran Kexueban 1994; 30: 52-54.
- Benchadi W., Haba H., Lavaud C., Harakat D., Benkhaled M Secondary metabolites of Astragalus cruciatus Link and their chemotaxonomic significance Rec Nat Prod 2013; 7: 105-113.
- Kavtaradze NS., Alaniya MD., Mshvildadze VD., Skhirtladze AV., Lavoie S., Pichette A Flavonoids from Astragalus microcephalus Chemistry of Natural Compound 2011; 46: 971-973.
- Alaniya MD., Komissarenko NF., Kemertelidze EP., Khim Prir Soedin 1975; II: 351-354.
- [31] Alaniya MD., Kavtaradze NS., Bassarello C., Skhirtladze AV., Pizza C., Kutateladze I. Flavonoid glycosides from Astragalus galegiformis leaves Chemistry of Natural Compound 2006; 42: 681-685.
- Tsepkova NA., Svechnikova AN., Bandyukova VA Khalmatov KhKh. Khim Prir Soedin 1972; 5: 661.
- Guzhva NN., Dzhumyrko SF., Kazarov AL. Khim Prir Soedin 1984; 6: 522-523.
- Guzhva NN., Luk'yanchikov MS., Dranik LI. Khim Prir Soedin 1987; 5: 455.
- Yasinov RK., Syrovezhko NV., Yakovlev GP. Khim Prir Soedin 1986; d: 781-782.
- Luk'yanchikov MS., Guzhva NN., Elisevich DM. Khim Prir Soedin 1987; i: 453-454.
- Guzhva NN., Ushakov VB., Luk'yanchikov MS., Sarkisov LS., Khim Prir Soedin 1986; 6: 783-784.
- Kazarov AL., Luk'yanchikov MS., Dzhumyrko SF., Kompantsev VA., Khim Prir Soedin 1981 (i) 388-9 CA 95:147130
- Kazarov AL., Dzhumyrko SF., Sergeeva TA., Kompantsev VA. Khim Prir Soedin 1981; 3: 391-392.
- Sidel'nikova VI. Khim Prir Soedin 1978; i: 387-388.
- Alaniya MD., Komissarenko NF., Kemertelidze EP. Khim Prir Soedin 1972 (6) 802 CA 78:94813
- Guzhva NN., Sarkisov LS., Dzhumyrsko SF., Prudnik YV. Khim Prir Soedin 1990; 5: 406-407.
- Ionkova I. Planta Medica 1990; 56: 581.
- Cui BL., Lu YR., Wei LX. Yaoxue Xuebao 1989; 24: 189-193.
- Guzhva NN. Flavonoids and hydroxycinnamic acids from Astragalus asper Chemistry of Natural Compound 2010; 46: 303-304.
- Alaniya MD., Kavtaradze NS., Bassarello C., Skhirtladze AV., Pizza C., Kutateladze I. Flavonoids from Astragalus hamosus Natural Product Research 2007; 21: 392-395.
- Khoron'ko AT., Glyzin VI. Khim Prir Soedin 1973; P: 430-431.
- Deryugina LI., Maksyutina NP., Krivenchuk PE. Khim Prir Soedin 1966; 2: 394-399.
- Marechkova L., Kumanova B. Probl Farm 1981; P: 63-74.
- Deryugina LI., Maksyutina NP., Krivenchuk PE. Khim Prir Soedin1968; 4: 254-255.
- Yahara S Kohjyouma M Kohoda H. Phytochemistry 2000; 53: 469-471.
- Cui B., Nakamura M., Kinjo J., Nohara T. Chemical & Pharmaceutical Bulletin 1993; 41: 178-182.
- Alaniya MD., Komissarenko NF., Kemertelidze EP. Soobshch Akad Nauk Gruz SSR 1975; 80: 625-628.
- Alaniya MD. Khim Prir Soedin 1976; 6: 813.
- Ibragimova N Kh., Kozhabekova SS. Probl Farm Nauki Prakt., Mater S'ezdaFarm Kaz 1st 1975; 224-227.
- Yasinov RK. Khim Prir Soedin 1986; 3: 376-377.
- Yasinov RK., Yakovlev GP. Khim Prir Soedin 1986; 5: 373-374.
- Ma Y., Tian Z., Fan C, Meng R. Shenyang Yaoxueyuan Xuebao 1991; 8: 121-123.
- Khozhambergenova P., Blinova KF. Khim Prir Soedin 1979; 5: 726-727.
- Polyakova LV., Ershova EA., Rastit Resur 1996; 32: 74-79.
- Dungerdorzh D., Petrenko VV., Deryugina LI. Khim Prir Soedin 1974; 7: 250-251.
- Komissarenko NF., Polyakova LV. Khim Prir Soedin 1987; 2: 302-304.
- Norris FA., Stermitz FR. Phytochemistry 197; 9: 229-230.
- Dunzerdorzh D., Petrenko VV. Khim Prir Soedin 1973; 2: 272.
- Deryugina LI., Krivenchuk PE., Maksyutina NP. Farm Zh (Kiev) 1966; 27: 41-45.
- Lu S., Zhu Y., Wu S. Zhongcaoyao 1990; 27: 249-250.
- Polyakova LV., Yershova EA. Rastit Resur 1996; 32: 81-87.
- Alaniya MD., Kemertelidze EP. Izv Akad Nauk Gruz SSR Ser Khim 1981; 7: 125-130.
- Gupta RK., Singh J., Santani DD. Fitoterapia 1995; 66: 376.
- Khoron'ko AT. Khim Prir Soedin 1974; 10: 88-89.
- Imomnazarov BA., Isaev MI., Saboiev SS., Abubakirov NK. Khim Prir Soedin 1990; 6: 783-787.
- Gupta RK., Singh J., Santani DD. Indian Drugs 1993; 30: 595.
- Yamaki M., Kashihara M., Takagi S. Shoyakugaku Zasshi 1991; 45: 261-262.
- Tian Z., Ma Y., Meng R., Li B., Shenyang Yaoxueyuan Xuebao 1993; 10: 24-26.
- Cui B., Nakamura M., Kinjo J., Nohara T. Chemical & Pharmaceutical Bulletin 1992; 40: 1943-1945.
- Li W., Sun YN., Yan XT., Yang SY., Kim S., Lee YM., Koh YS., Kim YH. Flavonoids from Astragalus membranaceus and their inhibitory effects on LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells Archive of Pharmaceutical Research 2014; 37: 186-192.
- Lenssen AW., Martin SS., Townsend CE., Hawkins B. Photochemistry 1994; 36: 1185-1187.
- Lenssen AW., Townsend CE., Martm SS. Crop Science 1995; 3: 756-776.
- Martin SS., Townsend CE., Lenssen AW:, Biochem System EcoL 1994 22 657-661
- Zhang LJ., Liu HK., Hsiao PC., Kuo LMY., Lee I-J., Wu TS., Chiou WF., Kuo YH
- New isoflavonoid glycosides and related constituents from Astragali Radix (Astragalus membranaceus) and their inhibitory activity on nitric oxide production J Agric Food Chem 2011 59 1131-1137
- Shirataki Y., Takao M., Yoshida S., Toda S. Phytotherapy Research 1997; 77: 603-605.
- Toda S., Shirataki Y. Phytotherapy Research 1998; 72: 59-61.
- Yu X., Liu X. Zhiwu Ziyuan Yu Huanjing 1993; 2: 40-43.
- Baratta MT., Ruberto G. Planta Medica. 1997; 63: 280-282.
- Zheng Z., Song C, Liu T., Hu Z. Yaoxue Xuebao 1998; 33: 148-151.
- Baek N-L, Kim Y S., Kyung J S., Park K H. Saengyak Hakhoechi 1996; 27: 111-116.
- Tang W Eisenbrand G. Chinese Drugs of Plant Origin Springer-Verlag: Berlin 1992
- Agzamova MA: Isaev MI. Chemistry of Natural Compound 1998; 34: A11-A19.
- Agzamova MA: Isaev MI. Chemistry of Natural Compound 1998; 34: 155-159.
- Yu Z., Liu X., Dai J., Pu Q. Tianran Chanwu Yanjiu Yu Kaifa 1994; 6: 1-5.
- Marco JL., Sanz J., Rodriguez B. An Quim Ser C 1983; 79: 94-95.
- Fathiazad F., Movafeghi A., Khosropanah MK. Flavonol glycosides from the leaves of Astragalus microcephalus International Journal of Bioscience 2012; 2: 23-28.
- Yu DH., Bao YM., Wei C., An LJ. Studies of chemical constituents and their antioxidant activities from Astragalus mongholicus Bunge Biomed Environ Sci 2005; 18: 297-301.
- Du X., Bai Y., Liang H., Wang Z., Zhao Y., Zhang Q., Huang L. Solvent effect in 1H-NMR spectra of 3'-hydroxy-4'-methoxy isoflavonoids from Astragalus membranaceus var mongholicus Magnetic Resonance Chemistry 2006; 44: 708-712.
- Abd El-Latif RR., Shabana MH., El-Gandour AH., Mansour RM., Sharaf M. A new isoflavone from Astragalus peregrinus Chemistry of Natural Compound 2003; 39: 536-537.
- Ingham JL., Dewick PM. Phytochemistry 1980; 19: 1767-1770.
- Song C, Zheng Z., Liu D., Hu Z. Zhiwu Xuebao 1997; 39: 486-488.
- Subamas A., Oshima Y., Hikino H. Phytochemistry 1991; 30: 2777-2780.
- He Z- Q., Findlay J A. Journal of Natural Product 1991; 54: 810-815.
- Song C, Zheng Z., Liu D., Hu Z., Sheng W., Zhiwu Xuebao 1997 39 1169-1171 CA 130:78683
- El-Sebakhy N., Asaad AM., Abdallah RM., Toaima SM., Abdel-Kader MS., Stermitz FR. Phytochemistry 1994; 36: 1387-1389
- Tadzhibaev MM., Lutfullin KI., Mirzamatov RT. Khim Prir Soedin 1988; 5: 457-458.
- Leyla Maamria Hamada Haba Catherine Lavaud Dominique Harakat Mohammed Benkhaled. An isoflavane and saponins from Astragalus depressus Journal of Serb Chemical Society 2015; 80: 137-142.
- Lipkan GM., Maksyutina NP. Farm Zh (Kiev) 1973; 28: 59-90.
- Luk'yanchikov MS. Khim Prir Soedin 1984 (7) 43-45.
- Harbone JB. In The Flavonoids-Advances in Research since 1980, Chapman and Hall: London 1988.
- Zhang D., Zhuang Y., Pan J., Wang H., Li H., Yu Y., Wang D. Investigation of effects and mechanisms of total flavonoids of Astragalus and calycosin on human erythroleukemia cells. Oxid Med Cell Longev 2012; 2012 209843
- Wang D., Zhuang Y., Tian Y., Thomas GN., Ying M. Tomlinson B Study of the effects of total flavonoids of Astragalus on atherosclerosis formation and potential mechanisms. Oxid Med Cell Longev 2012 2012 doi:org/101155/2012/282383
- Bai F., Makino T., Kono K., Nagatsu A., Ono T., Mizukami H. Calycosin and formononetin from astragalus root enhance dimethylarginine dimethylaminohydrolase 2 and nitric oxide synthase expressions in Madin Darby Canine Kidney II cells. Journal of Natural Medicine 2013; 67: 782-789.
- Kim EJ., Yang KS Antilipidperoxidative activity of Astragalus membranaceus Yakhak Hoechi 2005; 49: 11-19
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