APIGENIN

Structure

2D structure of APIGENIN
2D structure
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3D model

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

Names and identifiers

Name

APIGENIN

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

SMILES

C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O

General information

Molecular formula

C15H10O5

Molecular weight

270.24 g/mol

Monoisotopic mass

270.0528 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
No

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

Plants with the compound

Plant Plant part Amount Reference
Achillea millefolium L. subsp. millefolium - -
List, P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979.
Agrimonia eupatoria L. subsp. eupatoria - -
Newall, C. A., Anderson, L. A. and Phillipson, J. D. 1996. Herbal Medicine - A Guide for Health-care Professionals. The Pharmaceutical Press, London. 296pp.
Arabidopsis thaliana (L.) Heynh. - -
Bhushan, R., Dhiman, R.P. (1984). Study of natural products of some plants of garhwal region. Trans Indian Soc Desert Techno Univ Cen Desert Studies, 9(2), 93-94
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.
Ballota nigra L. subsp. meridionalis (Bég.) Bég. aerial parts -
Seidel, V., Verholle, M., Malard, Y., Tillequin, F., Fruchart, J-C., Duriez, P., Bailleul, F., Teissier, E. 2000. Phenylpropanoids from Ballota nigra L. Inhibit in vitro LDL Peroxidation. Phytotherapy Research, 14(2): 93-98.
Bellis perennis L. flower -
Gudej, J., Nazaruk, J. (1997). Apigenin glycosidoesters from flowers of Bellis perennis L. Acta Pol Pharm, 54(3), 233-235
Betonica officinalis L. aerial parts -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
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
Carduus pycnocephalus L. subsp. pycnocephalus aerial parts -
Amer, M.M.A., Salama, O.M., Omar, A.A. (1985). Flavonoids of Cardus pycnocephalus. Fitoterapia, 56(1), 61
Cerastium holosteoides Fr. aerial parts -
Darmograi, V.N. (1979). Flavonoids of some species of the genera Arenaria and Cerastium. Chem Nat Comp, 15(1), 78 doi:10.1007/bf00570864
Cichorium intybus L. aerial parts -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Cirsium arvense (L.) Scop. leaf -
Wollenweber, E., Mann, K., Hochwart, S., Yatskievych, G. (1989). Exudate flavonoids in miscellaneous Asteraceae. Phytochem Bull, 21(2), 19-23
Crataegus monogyna Jacq. flower -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Crataegus monogyna Jacq. fruit -
Newall, C. A., Anderson, L. A. and Phillipson, J. D. 1996. Herbal Medicine - A Guide for Health-care Professionals. The Pharmaceutical Press, London. 296pp.
Crataegus monogyna Jacq. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Cymbalaria muralis G.Gaertn., B.Mey. & Scherb. subsp. muralis aerial parts -
Romussi, G., Fontana, N., Detommasi, N. (1996). Flavonoids from Cymbalaria muralis Gaernt. Phytother Res, 10, S84-S85
Daphne laureola L. leaf -
Touati, D., Fkih-tetouani, S. (1993). Flavonoids of Daphne laureola L. Plant Med Phytother, 26(1), 43-48
Daucus carota L. fruit -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Equisetum arvense L. - -
Bisset, N.G., ed. 1994. Herbal Drugs and Phytopharmaceuticals. CRC Press. Boca Raton, FL. 566 pp.
Erigeron canadensis L. - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Ervilia hirsuta (L.) Opiz aerial parts -
Kovaleva, A.M., Kovalev, V.N., Shestko, I.E. (1987). Flavonoids of some species of vetch. Chem Nat Comp, 22(6), 724 doi:10.1007/bf00598367
Glechoma hederacea L. - -
Jim Duke's personal files.
Globularia bisnagarica L. aerial parts -
Klimek, B. (1988). Acylated 6-hydroxyluteolin diglucosides from Globularia elongata. Phytochemistry, 27(1), 255-258 doi:10.1016/0031-9422(88)80626-5
Juniperus communis L. - -
Newall, C. A., Anderson, L. A. and Phillipson, J. D. 1996. Herbal Medicine - A Guide for Health-care Professionals. The Pharmaceutical Press, London. 296pp.
Lathyrus pratensis L. subsp. pratensis flower -
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
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
Matricaria chamomilla L. - -
Oliveira, L.J., Pintoneto, N., Tavares, M.F.M. (2001). Critical assessment of electrolyte systems for the capillary electrophoresis analysis of phenolic compounds in herbal extracts. J Microcol Sep, 13(6), 227-235 doi:10.1002/mcs.1047
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
Matricaria chamomilla L. flower -
Carle, R., Dolle, B., Reinhard, E. (1989). A new approach to the production of chamomile extract. Planta Med, 55(6), 540-543 doi:10.1055/s-2006-962089
Matricaria chamomilla L. flower -
Exner, J., Reiching, J., Cole, T.C.H., Becker, H. (1981). Methylated flavonoid-aglycones from Matricariae Flos. Planta Med, 41, 198-200 doi:10.1055/s-2007-971700
Matricaria chamomilla L. flower -
Fonseca, F.N., Tavares, M.F.M. (2004). Validation of a capillary electrophoresis method for the quantitative determination of free and total apigenin in extracts of Chamomilla recutita. Phytochem Anal, 15(1), 65-70 doi:10.1002/pca.744
Matricaria chamomilla L. flower -
Hava, M., Janku, I. (1958). Bronchodilator action of apigenin. Arch Int Pharmacodyn Ther, 117, 23
Matricaria chamomilla L. flower -
Kolinek, J., Kolinkova, B., Proksa, B. (1986). Aqueous extract of Matricaria chamomilla. Patent Czech 231,474
Matricaria chamomilla L. flower -
Maier, R., Carle, R., Kreis, W., Reinhard, E. (1993). Purification and characterization of a flavone 7-o-glucoside-specific glucosidease from ligulate florets of Chamomilla recutita. Planta Med, 59(5), 436-441 doi:10.1055/s-2006-959727
Matricaria chamomilla L. flower -
Redaelli, C., Formentini, L., Santaniello, E. (1981). Reversed-phase high-performance liquid chromatography analysis of apigenin and its glucosides in flowers of Matricaria chamomilla and chamomile extracts. Planta Med, 42, 288-292 doi:10.1055/s-2007-971643
Medicago sativa L. aerial parts 70 ppm
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Mentha spicata L. leaf -
List, P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979.
Onopordum acanthium L. subsp. acanthium flower -
Karl, C., Mueller, G., Pedersen, P.A. (1976). On the phytochemistry of the flowers of Onopordon acanthium L. (cotton thistle). Dtsch Apoth Ztg, 116, 57-59
Onopordum acanthium L. subsp. acanthium flower -
Karl, C., Muller, G., Pedersen, P.A. (1976). Zur phytochemie der bluten von Onopordon acanthium L.(eselsdistel). Dtsch Apoth Ztg, 116, 57
Pilosella officinarum F.W.Schultz & Sch.Bip. - -
Shelyuto, V.L., Bondarenko, V.G., Glyzin, V.I. (1977). Search for biologically active substances in plants of the flora of the belorussian ssr. Mater S'Ezda Farm B Ssr 3Rd, 152-153
Pilosella officinarum F.W.Schultz & Sch.Bip. flower -
Barnaulov, O.D., Manicheva, O.A., Shelyuto, V.L., Konopleva, M.M., Glyzin, V.I. (1985). Effect of flavonoids on development of experimental gastric dystrophies in mice. Khim Farm Zh, 18(8), 935-941 doi:10.1007/bf00779271
Plantago major L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Populus ×canadensis Moench nothosubsp. canadensis flower -
Wang, X., Wang, H., Wang, Q. (2000). Chemical constituents of male inflorescence of Populus canadensis Moench. Zhongguo Yaoke Daxue Xuebao, 31(3), 171-173
Populus tremula L. bud -
Sokolov, I.V., Torgov, I.V. (1991). Flavonoid aglycons in propolis and its sources. Chem Nat Comp, 26(4), 468 doi:10.1007/bf00599014
Populus tremula L. bud -
Wollenweber, E. (1975). Flavonoid distribution and systematics in the genus Populus. Biochem Syst Ecol, 3, 35
Primula veris L. subsp. columnae (Ten.) Maire & Petitm. flower -
Karl, C., Muller, G., Pedersen, P.A. (1981). Flavonoids in the flowers of Primula officinalis. Planta Med, 41, 96-99
Salix alba L. bark -
Pedersen, M. 1987. Nutritional Herbology. Pederson Publishing. Bountiful, Utah. 377 pp.
Salix alba L. leaf -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Stellaria media (L.) Vill. aerial parts -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Succisa pratensis Moench - -
Kowalczyk, A., Krzyanowska, J. (1999). Preliminary antifungal activity of some Dipsacaceae family plants. Herba Pol, 45(2), 101-107
Tanacetum vulgare L. subsp. vulgare - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Triticum aestivum L. subsp. aestivum seed -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Verbascum phlomoides L. flower -
Papay, V., Toth, L., Osvath, K., Bujtas, G.Y. (1980). On the flavonoids from Verbascum phlomoides L. Pharmazie, 35, 334-335
Veronica chamaedrys L. subsp. chamaedrys - -
Gusev, N.F., Teslov, S.V., Guseva, N.M. (1974). Flavonoids of Veronica genus plants. Chem Nat Comp, 10(4), 531
Veronica chamaedrys L. subsp. chamaedrys aerial parts -
Nikolova, M., Gevrenova, R., Ivancheva, S. (2003). External flavonoid aglycones from Veronica chamaedrys L. (Scrophyulariaceae). Acta Pharm(Zagreb), 53(2), 145-149
Viburnum lantana L. leaf -
Godeau, R.P., Pelissier, Y., Sors, C., Fouraste, I. (1978). Study of the flavonoids of the leaves of Viburnum lantana and Viburnum tinus. Plant Med Phytother, 12, 296-304
Vicia sativa L. aerial parts -
Kovaleva, A.M., Kovalev, V.N., Shestko, I.E. (1987). Flavonoids of some species of vetch. Chem Nat Comp, 22(6), 724 doi:10.1007/bf00598367
Vicia segetalis Thuill. aerial parts -
Kovaleva, A.M., Kovalev, V.N., Shestko, I.E. (1987). Flavonoids of some species of vetch. Chem Nat Comp, 22(6), 724 doi:10.1007/bf00598367