Antisweet Natural Products. XII. Structures of Sitakisosides XI-XX from Stephanotis lutchuensis KOIDZ. var. japonica

From the fresh stem of Stephanotis lutchuensis var. japonica, ten new oleanane-type triterpenoid glycosides, named sitakisosides XI-XX (1-10), were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. The results show that all have a 3-O-β-D-xylopyrano...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 45; no. 1; pp. 62 - 67
Main Authors YOSHIKAWA, Kazuko, MIZUTANI, Aki, KAN, Yukiko, ARIHARA, Shigenobu
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1997
Maruzen
Japan Science and Technology Agency
Subjects
antisweet substance
Asclepiadaceae
Biological and medical sciences
Carbohydrate Sequence
Flavoring Agents - administration & dosage
Flavoring Agents - chemistry
General pharmacology
Humans
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Sequence Data
N-methylanthranilic acid
oleanane triterpene
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Extracts - chemistry
Plant Stems - chemistry
Plants - chemistry
Saponins - chemistry
Saponins - isolation & purification
sitakisoside
Stephanotis lutchuensis var. japonica
Sucrose - administration & dosage
Sucrose - antagonists & inhibitors
Taste - drug effects
Asia
Japan
Pentacyclic compound
Pharmacognosy
Organoleptic properties
Asclepiadaceae
Alcohol
Disaccharide
Stem
Medicinal plant
Saponin
Dicotyledones
Angiospermae
Plant origin
Triterpene
Isolation
Sweet taste
Spermatophyta
Glycoside
Ethylenic compound
Trisaccharide
Structural analysis
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Summary:From the fresh stem of Stephanotis lutchuensis var. japonica, ten new oleanane-type triterpenoid glycosides, named sitakisosides XI-XX (1-10), were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. The results show that all have a 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl moiety and the aglycones of sitakisosides XI-XV, XVI and XVII, XVIII and XIX, and XX are sitakisogenin, chichipegenin, marsglobiferin and longispinogenin, respectively. Sitakisosides XI-XIII, XVI and XVIII, having an acyl group, showed antisweet activity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.45.62