Cucurbitane glycosides from Hemsleya panacis-scandens rhizomes

• Published in: Phytochemistry (Oxford) Vol. 41; no. 4; pp. 1169 - 1174
• Main Authors: Kubo, Hideo, Ohtani, Kazuhiro, Kasai, Ryoji, Yamasaki, Kazuo, Nie, Rui-Lin, Tanaka, Osamu
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01-03-1996; Elsevier
• Subjects: Biological and medical sciences; Chemical constitution; Fundamental and applied biological sciences. Psychology; Plant physiology and development; rhizomes; cucurbitane glycosides; Cucurbitaceae; scandenosides R8-R11; perseapicroside A; Hemsleya panacis-scandens; scandenogenins E; sweet natural glycoside; scandenogenins D; Molecular structure; Dicotyledones; Angiospermae; Rhizome; Bitter taste; Isolation; Sweet taste; Spermatophyta; Glycoside; Natural compound
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/0031-9422(95)00722-9

From the rhizomes of
Hemsleya panacis-scandens, four new cucurbitane glycosides and a known glycoside, perseapicroside A, were isolated. The structures of these new glycosides, named scandenosides R8-R11, were determined as the
3-O-β-
d-glucopyranoside
-26-O-β-
d-glucopyranoside
of 3β,26-dihydroxycucurbit-5-en-11-one, the
2-O-β-
d-glucopyranoside
of 2β,3α,16α-trihydroxy-22,23,24,25,26,27-hexanorcucurbit-5-ene-11,20-dione, the
3-O-β-
d-glucopyranoside
of 2
β,3
α,20(
S),26,27-pentahydroxy-16
α,23(
S)-epoxycucurbita-5,24-dien-11-one and the
3-O-β-
d-glucopyranoside
-26-O-β-
gentiobioside
of 3β,11α,26-trihydroxy-5β,6β-epoxycucurbit-24-ene by spectroscopic and chemical methods. The structure of perseapicroside A was shown to be incorrect.