ASTRAGALIN

Structure

2D structure of ASTRAGALIN
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 5282102

Names and identifiers

Name

ASTRAGALIN

Also reported as

KAEMPFEROL-3-O-BETA-D-GLUCOSIDE = ASTRAGALIN

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

SMILES

C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O

General information

Molecular formula

C21H20O11

Molecular weight

448.38 g/mol

Monoisotopic mass

448.1006 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
Yes

Chemical classification: NPClassifier (Kim et al., 2021)

Plants with the compound

Plant Plant part Amount Reference
Acer negundo L. bark -
Backheet, E.Y., Enaam, Y. (2003). Gallotannin and flavonoid glycosides from the stem bark of Acer negundo L. Bull Pharm Sci Assiut Univ, 26(1), 77-82 doi:10.21608/bfsa.2003.65470
Agrimonia eupatoria L. subsp. eupatoria aerial parts 23-24 ppm
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Althaea cannabina L. flower -
Gudei, J., Dzido, T.H. (1991). Quantitative determination of flavonoid glycosides in leaves and flowers from some species of Althaea genus using the hplc technique. Acta Pol Pharm, 48(3/4), 59-62
Althaea cannabina L. leaf -
Gudei, J., Dzido, T.H. (1991). Quantitative determination of flavonoid glycosides in leaves and flowers from some species of Althaea genus using the hplc technique. Acta Pol Pharm, 48(3/4), 59-62
Arabidopsis thaliana (L.) Heynh. - -
Gupta, D.R., Dhiman, R.P. (1985). Chemical investigation of Arabidopsis thaliana (L.) Heynh. Pharmazie, 40(5), 365
Arctium minus (Hill) Bernh. - -
Saleh, N.A.M., Bohm, B.A. (1971). Flavonoids of Arctium minus (Compositae). Experientia, 27, 1494 doi:10.1007/bf02154314
Arnica montana L. subsp. montana flower -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Artemisia alba Turra root -
Marco, J.A., Barbera, O., Sanchez-parareda, J. (1987). Flavonol and coumarin glycosides from Artemisia incanescens. J Nat Prod, 50(4), 774-775 doi:10.1021/np50052a045
Artemisia annua L. - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Artemisia annua L. aerial parts -
Wright,C.W.(Ed)2002.Medicinal&Aromatic Plants-Industrial Profiles.Artemisia.344pp.Maffei,M.(Ed)2002.Vetiveria.The Genus Vetiveria.Taylor&Francis.NY,NY.191pp.Southwell,I.,Lowe,R.(Eds)1999.Tea Tree.The Genus Melaleuca.Harwood Acad.Pub.Amsterdam,Netherlands.
Bellis perennis L. flower -
Gudej, J., Nazaruk, J. (2001). Flavonol glycosides from the flowers of Bellis perennis. Fitoterapia, 72(7), 839-840 doi:10.1016/s0367-326x(01)00309-4
Bidens frondosa L. leaf -
Karikome, H., Ogawa, K., Sashida, Y. (1992). New acylated glucosides of chalcone from the leaves of Bidens frondosa. Chem Pharm Bull, 40(3), 689-691 doi:10.1248/cpb.40.689
Briza media L. leaf -
Williams, C.A., Murray, B.G. (1972). Flavonoid variation in the genus Briza. Phytochemistry, 11, 2507-2512 doi:10.1016/s0031-9422(00)88526-x
Cichorium intybus L. - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Cichorium intybus L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Cirsium vulgare (Savi) Ten. subsp. vulgare leaf -
Mcgowan, S.G., Wallace, J.W. (1972). Flavonoids and phenolic acids from Cirsium lanceolatum. Phytochemistry, 11, 1503-1504 doi:10.1016/s0031-9422(00)90119-5
Corylus avellana L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Crocus vernus (L.) Hill flower -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Cuscuta campestris Yunck. aerial parts -
Loffler, C., Czygan, F.C., Proksch, P. (1997). Phenolic constituents as taxonomic markers in the genus Cuscuta (Cuscutaceae). Biochem Syst Ecol, 25(4), 297-303 doi:10.1016/s0305-1978(97)00015-x
Daucus carota L. root -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Daucus carota L. seed -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Emerus major Mill. subsp. major flower -
Harborne, J.B., Boardley, M. (1983). Trisubstituted flavonol glycosides in Coronilla Emerus flowers. Phytochemistry, 22(2), 622-625 doi:10.1016/0031-9422(83)83074-x
Equisetum arvense L. aerial parts -
Jim Duke's personal files.
Equisetum arvense L. leaf -
Jim Duke's personal files.
Equisetum telmateia Ehrh. - -
Geiger, H., Lang, U., Britsch, E., Mabry, T.J., Suhr-schucker, U., Velde, G.V., Waldrum, H. (1978). The flavone glycosides of Equisetum telmateja. Phytochemistry, 17, 336-337 doi:10.1016/s0031-9422(00)94189-x
Equisetum telmateia Ehrh. seedling -
Beckert, C., Veit, M., Geiger, H., Czygan, F.C. (1993). Flavonoids of Equisetum sylvaticum, Equisetum pratense, and Equisetum x bowmanii. Planta Med Suppl, 59, A696-A697 doi:10.1055/s-2006-959988
Eryngium campestre L. aerial parts -
Kartnig, T., Wolf, J. (1993). Flavonoids from the aboveground parts of Eryngium compestre. Planta Med, 59(3), 285-286
Eupatorium cannabinum L. subsp. cannabinum - -
Stefanovic, M., Solaia, B., Dermanovic, M., Milovanovic, M. (1986). Chemical investigation of the plant species of Eupatorium cannabinum L. (compositae). J Serb Chem Soc, 51(12), 575-581
Eupatorium cannabinum L. subsp. cannabinum aerial parts -
Elema, E.T., Schripsema, J., Malingre, T.M. (1989). Flavones and flavonol glycosides from Eupatorium cannabinum L. Pharm Weekbl(Sci Ed), 11(5), 161-164 doi:10.1007/bf01959464
Eupatorium cannabinum L. subsp. cannabinum leaf -
Pagani, F., Romussi, G. (1967). On the constituents of Eupatorium cannabinum L. var. syriacum (Jacq.). Farmaco Ed Prat, 22, 771-785
Euphorbia helioscopia L. subsp. helioscopia aerial parts -
El-salam, N.A.A., El-sayed, M.A., Khafagy, S.M. (1975). Spectrophotometric estimation of individual flavone glycosides in three Euphorbia species. Pharmazie, 30, 402
Euphorbia maculata L. aerial parts -
Agata, I., Hatano, T., Nakaya, Y., Sugaya, T., Nishibe, S., Yoshida, T., Okuda, T. (1991). Tannins and related polyphenols of Euphorbiaceous plants. viii. eumaculin a and eusupinin a, and accompanying polyphenols from Euphorbia maculata L. and E. supina rafin. Chem Pharm Bull, 39(4), 881-883 doi:10.1248/cpb.39.881
Euphorbia peplus L. - -
Rizk, A.M., Hammouda, F.M., El-nasr, M.M.S., Abou-youssef, A.A. (1980). Phytochemical investigation of Euphorbia peplus. constituents of egyptian Euphorbiaceae. part 8. Fitoterapia, 51, 223-227
Euphorbia peplus L. aerial parts -
El-salam, N.A.A., El-sayed, M.A., Khafagy, S.M. (1975). Spectrophotometric estimation of individual flavone glycosides in three Euphorbia species. Pharmazie, 30, 402
Fagus sylvatica L. exudate -
Tissut, M., Ravanel, P. (1980). Assessment of flavonols in adult leaves of several vegetative vacuoles. Phytochemistry, 19, 2077-2081
Fagus sylvatica L. leaf -
Dietrichs, H.H., Schaich, E. (1963). Flavonol glucosides in the buds and leaves of rotbuche (Fagus sylvatica L.). Naturwissenschaften, 50, 478
Fallopia convolvulus (L.) Á.Löve leaf -
Kim, M.H., Park, J.H., Park, C.W. (2000). Flavonoid chemistry of Fallopia section fallopia (Polygonaceae). Biochem Syst Ecol, 28(5), 433-441 doi:10.1016/s0305-1978(99)00084-8
Humulus lupulus L. fruit -
CRC Handbook of Medicinal Herbs and/or CRC Handbook of Proximate Analyses
Larix decidua Mill. leaf -
Niemann, G.J. (1975). Main flavonoids in needles of Larix decidua. Phytochemistry, 14, 1436 doi:10.1016/s0031-9422(00)98649-7
Laserpitium latifolium L. leaf -
Vereskovskii, V.V., Kuznetsova, Z.P., Loznukho, I.V., Sokolov, I.V., Osokin, D.M. (1993). Phenolic compounds of Laserpitium latifolium. Chem Nat Comp, 28(6), 631-632 doi:10.1007/bf00630451
Lathyrus pratensis L. subsp. pratensis flower -
Reynaud, J., Blaise, S., Jay, M., Cartier, D. (1982). Response of flavonoid metabolism to environmental selection pressure in diverse populations of Lathyrus pratensis L. Taxon, 31, 684-690
Lathyrus pratensis L. subsp. pratensis leaf -
Ismaili, A., Reynaud, J., Jay, M., Raynaud, J. (1981). Flavonoids of Lathyrus pratensis (Leguminosae). Plant Med Phytother, 15, 155-159 doi:10.1016/0031-9422(81)84073-3
Lepidium draba L. subsp. draba - -
Kurkin, V.A., Zapesochnaya, G.G., Krivenchuk, P.E. (1981). Flavonoids of orobus vernus, Lepidium draba and Lepidium ruderale. Khim Prir Soedin, 17(5), 661-662
Lepidium draba L. subsp. draba flower -
Kurkin, V.A., Zapesochnaya, G.G., Krivenchuk, P.E. (1981). Flavonoids of orobus vernus,Lepidium draba and Lepidium ruderale. Khim Prir Soedin, 17(5), 661-662
Lotus corniculatus L. leaf -
Reynaud, J., Jay, M., Raynaud, J. (1982). Flavonoid glycosides of Lotus corniculatus (Leguminosae). Phytochemistry, 21, 2604-2605 doi:10.1016/0031-9422(82)85271-0
Lotus tenuis Waldst. & Kit. ex Willd. - -
Wagner, M.L., Strittmatter, C.D., Kade, M., Rivero, M., Ricco, R.A., Gurni, A.A. (1996). Phytochemical survey of Lotus tenuis Waldst. and Kit. Phyton(Buenos Aires), 58(1/2), 141-146
Lotus tenuis Waldst. & Kit. ex Willd. flower -
Strittmatter, C.D., Wagner, M.L., Kade, M., Gurni, A.A. (1992). Identification of Lotus tenuis (Waldst. et Kit.) flavonoids. Biochem Syst Ecol, 20(7), 685-687 doi:10.1016/0305-1978(92)90025-9
Lotus tenuis Waldst. & Kit. ex Willd. leaf -
Strittmatter, C.D., Wagner, M.L., Kade, M., Gurni, A.A. (1992). Identification of Lotus tenuis (Waldst. et Kit.) flavonoids. Biochem Syst Ecol, 20(7), 685-687 doi:10.1016/0305-1978(92)90025-9
Lotus tenuis Waldst. & Kit. ex Willd. stem -
Strittmatter, C.D., Wagner, M.L., Kade, M., Gurni, A.A. (1992). Identification of Lotus tenuis (Waldst. et Kit.) flavonoids. Biochem Syst Ecol, 20(7), 685-687 doi:10.1016/0305-1978(92)90025-9
Matricaria chamomilla L. essential oil -
Mericli, A.H., Korkmaz, Y. (1992). Flavonoids of a Matricaria chamomilla var. recutica sample with no chamazulene in the volatile oil. Acta Pharm Turc, 34(3), 71-73
Morus alba L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Mutarda arvensis (L.) D.A.German flower -
Ali, A.A., Hassanean, H.A., Mohammed, M.H., Kamel, M.S., Elkhayat, E.S. (2000). Chemical and biological studies of Sinapis arvensis growing in egypt. Bull Pharm Sci Assiut Univ, 23(2), 99-109 doi:10.21608/bfsa.2000.66323
Papaver rhoeas L. subsp. rhoeas flower -
Hillenbrand, M., Zapp, J., Becker, H. (2004). Depsides from the petals of Papaver rhoeas. Planta Med, 70(4), 380-382 doi:10.1055/s-2004-818956
Parietaria officinalis L. - -
Circosta, C., Limardi, F., Occhiuto, F. (1992). Antibronchospastic activity of flavonol glycosides of different extracts from Parietaria officinalis L. Riv Ital Eppos, 3(7), 42-48
Parietaria officinalis L. flower -
Budzianowski, J., Skrzypczak, L., Walkowiak, D. (1985). Flavonoids of Parietaria officinalis. J Nat Prod, 48(2), 336-337 doi:10.1021/np50038a033
Persicaria lapathifolia (L.) Delarbre subsp. lapathifolia - -
Park, S.H., Oh, S.R., Jung, K.Y., Lee, I.S., Ahn, K.S., Kim, J.H., Kim, Y.S., Lee, J.J., Lee, H.K. (1999). Acylated flavonol glycosides with anti-complement activity from Persicaria lapathifolia. Chem Pharm Bull, 47(10), 1484-1486 doi:10.1248/cpb.47.1484
Persicaria lapathifolia (L.) Delarbre subsp. lapathifolia aerial parts -
Smolarz, H.D. (2002). Flavonoids from Polygonum lapathifolium ssp. tomentosum. Pharmaceutical Biol, 40(5), 390-394 doi:10.1076/phbi.40.5.390.8455
Persicaria maculosa Gray leaf -
Isobe, T., Noda, Y. (1987). A chematoxonomic study of flavonoids from japanese Polygonum species. Yakugaku Zasshi, 107(12), 1001-1004 doi:10.1248/yakushi1947.107.12_1001
Petasites hybridus (L.) G.Gaertn., B.Mey. & Scherb. subsp. hybridus leaf -
ANON. 1948-1976. The Wealth of India raw materials. Publications and Information Directorate, CSIR, New Delhi. 11 volumes.
Phytolacca americana L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Prunus persica (L.) Batsch - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Pteridium aquilinum (L.) Kuhn subsp. aquilinum - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Pyrus communis L. subsp. pyraster (L.) Ehrh. - -
No reference
Quercus cerris L. leaf -
Romussi, G., Ciarallo, G., Parodi, B. (1988). A glycoside from Quercus cerris L. Pharmazie, 43(4), 294-295
Rosa canina L. fruit -
List, P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979.
Salix alba L. pollen -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Sambucus nigra L. - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Sambucus nigra L. flower -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Sanicula europaea L. aerial parts -
Cisowski, W., Bieganowska, M.L. (1986). Hplc analysis of flavonoid compounds from both Meum athamanticum Jacq. and Sanicula europaea L. herbs. Herba Pol, 32(3/4), 155-159
Solidago gigantea Aiton flower -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Solidago virgaurea L. subsp. virgaurea leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Urtica dioica L. - 20 ppm
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Urtica dioica L. flower -
Jim Duke's personal files.
Vaccinium myrtillus L. fruit -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Vaccinium myrtillus L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Viburnum lantana L. fruit -
Guichard, J.P., Regerat, F., Pourrat, H. (1976). Flavones and anthocyanins in fruits of Viburnum lanata. Plant Med Phytother, 10, 105
Vitis ×instabilis Ardenghi, Galasso, Banfi & Lastrucci leaf -
Moore, M.O., Giannasi, D.E. (1987). Foliar flavonoids of selected Vitis taxa in the southeastern united states. Biochem Syst Ecol, 15(1), 79-83 doi:10.1016/0305-1978(87)90085-8