Sweet pregnane glycosides from Telosma procumbens.
An intensely sweet polyoxypregnane glycoside, telosmoside A15 (15), was isolated from an Asian Asclepiadaceae plant, Telosma procumbens, collected in Vietnam. This is the first time a sweet pregnane glycoside has been found, and its sweetness intensity is 1000 times greater than that of sucrose. From the same plant, 17 other new glycosides were isolated, having the same aglycone; they are named telosmosides A1-A14 (1-14) and A16-A18 (16-18). Some of these glycosides are also sweet, but others are tasteless or bitter. Chemical structures of the 18 glycosides were determined, and the structure-taste relationship was discussed.
Huan
V D
VD
Institute of Pharmaceutical Sciences, Faculty of Medicine, Hiroshima University, Japan.
Ohtani
K
K
Kasai
R
R
Yamasaki
K
K
Tuu
N V
NV
D005959:Glucosidases / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D011278:Pregnanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013549:Sweetening Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013649:Taste / Q000187:drug effects; D014744:Vietnam
D006027:Glycosides; D011278:Pregnanes; D013549:Sweetening Agents; C432958:telosmoside A15; D005959:Glucosidases