CHEMICAL INVESTIGATION OF TRITERPENE GLYCOSIDES OF BERRIES OF COMMON IVY
Искендеров (Iskenderov), Гаибверди (Gaibverdi) Баширович (Bashirovich)
Мусаева (Musaeva), Саида (Saida) Шамиловна (Shamilovna)
- Publisher: Altai State University
Khimiia rastitel'nogo syr'ia (Chemistry of plant raw material)
(issn: 1029-5143, eissn: 1029-5151)
Hedera helix L., berries, triterpene glycosides, α-, β-hederin, pentaoside | Hedera helix L.; ягоды; тритерпеновые гликозиды; α-, β-гедерины; пентаозид
Was found the presence of four triterpene glycosides named with increasing of their polarity as glycosides A, B, C, D by thin layer chromatography in the extract of berries of common ivy (Hedera helix L.) of the family Araliaceae. Using the method of fractional extraction from raw material are obtained two fractions: low polar (glycosides A and B) and polar (glycosides C and D). Total number of sums triterpene glycosides is 3,71%. Individual glycoside were isolated from respective fractions by adsorption column chromatography on silica gel. Glycoside A – composition С41Н66О11, M.P. 228–230 °C, +17,8° (c 0,5; 80% ethanol); glycoside B – composition С41Н66О12, M.P. 236–238 °C, +16,2° (c 0,7; 80% ethanol); glycoside C – composition С58Н94О25, M.P. 188–190 °C, +9° (c 0,1; 50% ethanol); glycoside D – composition С58Н94О26, M.P. 190–192 °C, +7° (c 0,15; 50% ethanol). By classical chemical methods, IR spectroscopy and thin layer chromatography is established the identity of low-polarity biosides and chemical nature of the polar triterpene glycosides. Glycoside A has the chemical structure as 3-O-alpha-L-rhamnnopyranosyl-(1→2)-O-alpha-L-arabinopyranoside oleanolic acid and it is known glycoside β-hederin. Glycoside B has a similar carbon chain, and as aglycone contains hederagenin, was identified as α-hederin. Polar glycosides C and D are the pentaosides of hederagenin and oleanolic acid, respectively. The carbohydrate chains include: 2 moles of L-arabinose, one mole of D-glucose, D-galactose and L-rhamnose. Both glycosides are monodesmosides.