APIGENIN-6-8-DI-C-GLYCOSIDE

Structure

2D structure of APIGENIN-6-8-DI-C-GLYCOSIDE
2D structure
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3D model

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

Names and identifiers

Name

APIGENIN-6-8-DI-C-GLYCOSIDE

Also reported as

APIGENIN-6-C-BETA-D-GLUCOPYRANOSYL-8-C-BETA-D-GALACTOPYRANOSIDE; VICENIN-2

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one

SMILES

C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O

General information

Molecular formula

C27H30O15

Molecular weight

594.52 g/mol

Monoisotopic mass

594.1585 Da

Classification

Pathway:
Superclass:
Class:
Glycoside:
No

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

Plants with the compound

Plant Plant part Amount Reference
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.
Bryonia dioica Jacq. leaf -
Proliac, A., Chaboud, A., Raynaud, J. (1989). Isolation and identification of 6-c-glucosyl-7-o-glucosyl-apigenin and 6,8,di-c-glucosylapigenin from the leaves of Bryonia dioica (Cucurbitaceae). Pharm Acta Helv, 64(7), 207-208
Cerastium arvense L. subsp. suffruticosum (L.) Ces. - -
Dubois, (1981). Contribution to a study of c-glycoflavonoids in the Caryophyllaceae, in particular in Cerastium arvense L. Bull Trav Soc Pharm(Lyon), 25(1/4), 46-49
Cerastium arvense L. subsp. suffruticosum (L.) Ces. - -
Dubois, M.A., Zoll, A., Bouillant, M.L., Delaveau, P. (1982). Di-c-glycosylflavones from Cerastium arvense ssp. arvense new for Caryophyllaceae. Planta Med, 46, 56-57 doi:10.1055/s-2007-970020
Cerastium arvense L. subsp. suffruticosum (L.) Ces. aerial parts -
Dubois, M.A., Zoll, A., Markham, K.R., Bouillant, M.L., Dellamonica, G., Chopin, J. (1984). 6-c-beta-d-glucopyranosyl-8-c-beta-d-galactopyranosylapigenin from Cerastium arvense. Phytochemistry, 23(3), 706-707 doi:10.1016/s0031-9422(00)80422-7
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. leaf 3 ppm
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.
Vicia sativa L. aerial parts -
Gamal-eldeen, A.M., Kawashty, S.A., Ibrahim, L.F., Shabana, M.M., El-negoumy, S.I. (2004). Evaluation of antioxidant, anti-inflammatory, and antinociceptive properties of aerial parts of Vicia sativa and its flavonoids J Nat Remedies, 4(1), 81-96
Vicia segetalis Thuill. aerial parts -
Gamal-eldeen, A.M., Kawashty, S.A., Ibrahim, L.F., Shabana, M.M., El-negoumy, S.I. (2004). Evaluation of antioxidant, anti-inflammatory, and antinociceptive properties of aerial parts of Vicia sativa and its flavonoids J Nat Remedies, 4(1), 81-96
Viola arvensis Murray subsp. arvensis - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Viola tricolor L. - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.