APIGENIN-7-O-BETA-D-GLUCOSYL-6-C-GLUCOSYL

Structure

2D structure of APIGENIN-7-O-BETA-D-GLUCOSYL-6-C-GLUCOSYL
2D structure
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3D model

Drawn and modelled with RDKit, 3D viewer 3Dmol.js. PubChem CID 441381

Names and identifiers

Name

APIGENIN-7-O-BETA-D-GLUCOSYL-6-C-GLUCOSYL

Also reported as

SAPONARIN

IUPAC name

5-hydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-7-(((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=CC(=O)C3=C(C(=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)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:
Yes

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

Plants with the compound

Plant Plant part Amount Reference
Alliaria petiolata (M.Bieb.) Cavara & Grande - -
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Arrhenatherum elatius (L.) P.Beauv. ex J.Presl & C.Presl subsp. elatius leaf -
Jay, M., Ismaili, A. (1989). Flavones and c-glycosylflavones from the leaves of some Arrhenatherum species. Phytochemistry, 28(11), 3035-3037 doi:10.1016/0031-9422(89)80274-2
Bryonia dioica Jacq. - -
Krauze-baranowska, M., Cisowski, W. (1994). High-performance liquid chromatographic determination of flavone c-glycosides in some species of the Cucurbitaceae family. J Chromatogr A, 675(1/2), 240-243 doi:10.1016/0021-9673(94)85278-2
Bryonia dioica Jacq. aerial parts -
Krauze, M., Cisowski, W. (1991). C-glycosides of apigenin from Bryonia alba L. Pol J Chem, 65(12), 2289-2290
Bryonia dioica Jacq. aerial parts -
Krauze-baranowska, M., Cisowski, W. (1995). Flavone c-glycosides from Bryonia alba and B. dioica. Phytochemistry, 39(3), 727-729 doi:10.1016/0031-9422(95)00069-j
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
Dipsacus fullonum L. - -
List, P.H. and Horhammer, L., Hager's Handbuch der Pharmazeutischen Praxis, Vols. 2-6, Springer-Verlag, Berlin, 1969-1979.
Saponaria officinalis L. aerial parts -
Bukharov, V.G., Shcherbak, S.P. (1969). Triterpene glycosides from Saponaria officinalis. Chem Nat Comp, 5, 324-326 doi:10.1007/bf00595069
Saponaria officinalis L. leaf -
Plouvier, V. (1966). Flavone heterosides: kaempferol 3-rhamnoglucoside myricitrin linarin and saponarin. C R Acad Sci Ser D, 262, 1368-1371
Stellaria media (L.) Vill. aerial parts 2 ppm
Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
Succisa pratensis Moench leaf -
Plouvier, V. (1966). Flavone heterosides: kaempferol 3-rhamnoglucoside myricitrin linarin and saponarin. C R Acad Sci Ser D, 262, 1368-1371
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.