Novel Polyoxygenated Spirostanol Glycosides from the Rhizomes of Helleborus orientalis

✍ Scribed by Yoshihiro Mimaki; Kazuki Watanabe; Chiseko Sakuma; Hiroshi Sakagami; Yutaka Sashida

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: German
• Weight: 184 KB
• Volume: 86
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200390040

✦ Synopsis

Abstract

The two new polyoxygenated spirostanol bisdesmosides 1 and 2 and the new trisdesmoside 3, named hellebosaponin A (1), B (2), and C (3), respectively, were isolated from the MeOH extract of the rhizomes of Helleborus orientalis. The structures of the new compounds were elucidated as (1__β__,3__β__,23__S__,24__S__)‐21‐(acetyloxy)‐24‐[(β‐D‐fucopyranosyl)oxy]‐3,23‐dihydroxyspirosta‐5,25(27)‐dien‐1‐yl O‐β‐D‐apiofuranosyl‐(1→3)‐O‐(4‐O‐acetyl‐α‐L‐rhamnopyranosyl)‐(1→2)‐O‐[β‐D‐xylopyranosyl‐(1→3)]‐α‐L‐arabinopyranoside (1), (1__β__,3__β__,23__S__,24__S__)‐ 21‐(acetyloxy)‐24‐{[O‐β‐D‐glucopyranosyl‐(1→4)‐β‐D‐fucopyranosyl]oxy}‐3,23‐dihydroxyspirosta‐5,25(27)‐dien‐1‐yl O‐β‐D‐apiofuranosyl‐(1→3)‐O‐(4‐O‐acetyl‐α‐L‐rhamnopyranosyl)‐(1→2)‐O‐[β‐D‐xylopyranosyl‐(1→3)]‐ α‐L‐arabinopyranoside (2), and (1__β__,3__β__,23__S__,24__S__)‐24‐[(β‐D‐fucopyranosyl)oxy]‐21‐{[O‐β‐D‐glucopyranosyl‐(1→2)‐β‐D‐galactopyranosyl]oxy}‐3,23‐dihydroxyspirosta‐5,25(27)‐dien‐1‐yl O‐β‐D‐apiofuranosyl‐(1→3)‐O‐(4‐O‐acetyl‐α‐L‐rhamnopyranosyl)‐(1→2)‐O‐[β‐D‐xylopyranosyl‐(1→3)]‐α‐L‐arabinopyranoside (3), respectively, on the basis of detailed spectroscopic studies and chemical evidence.