Turpinionosides A-E: megastigmane glucosides from leaves of Turpinia ternata Nakai.
From leaves of Turpenia ternata (Staphylaceae), one megastigmane and seven of its glucosides (1-8) were isolated. Megastigmane and two of the glucosides were found to be known compounds, namely, 3S,5R,6R,9S-tetrahydroxymegastigmane (1), corchoionoside C (2), and icariside B4 (3). The structures of compounds 4-8 (turpinionosides A-E, respectively) were elucidated by means of spectroscopic analyses, and then their absolute structures were determined by the modified Mosher's method to be (3S,5R,6S,9S)-3,6,9-trihydroxymegastigman-7-ene 3-O- and 9-O-beta-D-glucopyranosides (4, 5, respectively), (1S,3S,5R,6S,9R)-3,9,12-trihydroxymegastigmane 3-O-beta-D-glucopyranoside (6), (3S,4R,9R)-3,4,6-trihydroxymegastigman-5-ene 3-O-beta-D-glucopyranoside (7), and (2S,9R)-2,9-dihydroxymegastigman-5-en-4-one 2-O-beta-D-glucopyranoside (8).
Yu
Qian
Q
Institute of Pharmaceutical Science, Hiroshima University Faculty of Medicine, Japan.
Otsuka
Hideaki
H
Hirata
Eiji
E
Shinzato
Takakazu
T
Takeda
Yoshio
Y
D002855:Chromatography, Thin Layer; D005947:Glucose / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet
D005960:Glucosides; D005947:Glucose