Medicinal flowers. III. Marigold. (1): hypoglycemic, gastric emptying inhibitory, and gastroprotective principles and new oleanane-type triterpene oligoglycosides, calendasaponins A, B, C, and D, from Egyptian Calendula officinalis.
The methanolic extract and its 1-butanol-soluble fraction from the flowers of Calendula officinalis were found to show a hypoglycemic effect, inhibitory activity of gastric emptying, and gastroprotective effect. From the 1-butanol-soluble fraction, four new triterpene oligoglycosides, calendasaponins A, B, C, and D, were isolated, together with eight known saponins, seven known flavonol glycosides, and a known sesquiterpene glucoside. Their structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, glycosides A, B, C, D, and F, exhibited potent inhibitory effects on an increase in serum glucose levels in glucose-loaded rats, gastric emptying in mice, and ethanol- and indomethacin-induced gastric lesions in rats. Some structure-activity relationships are discussed.
Yoshikawa
M
M
Kyoto Pharmaceutical University, Japan. shoyaku@mb.kyoto-phu.ac.jp
Murakami
T
T
Kishi
A
A
Kageura
T
T
Matsuda
H
H
D000818:Animals; D000897:Anti-Ulcer Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D001786:Blood Glucose / Q000378:metabolism; D020838:Calendula / Q000737:chemistry*; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D004534:Egypt; D000431:Ethanol; D005746:Gastric Emptying / Q000187:drug effects*; D005951:Glucose Tolerance Test; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification; D007004:Hypoglycemic Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D007213:Indomethacin; D051379:Mice; D008969:Molecular Sequence Data; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000302:isolation & purification* / Q000494:pharmacology*; D013276:Stomach Ulcer / Q000139:chemically induced / Q000517:prevention & control
D000897:Anti-Ulcer Agents; D001786:Blood Glucose; D006027:Glycosides; D007004:Hypoglycemic Agents; D012503:Saponins; D000431:Ethanol; D007213:Indomethacin