Two New Cytotoxic Nonsulfated Pentasaccharide Holostane (=20-Hydroxylanostan-18-oic Acid γ-Lactone) Glycosides from the Sea Cucumber Holothuria grisea
✍ Scribed by Guo-Quan Sun; Ling Li; Yang-Hua Yi; Wei-Hua Yuan; Bao-Shu Liu; Yi-Yi Weng; Shi-Long Zhang; Peng Sun; Zeng-Lei Wang
- Book ID
- 102259832
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- German
- Weight
- 190 KB
- Volume
- 91
- Category
- Article
- ISSN
- 0018-019X
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Two new lanostane‐type nonsulfated pentasaccharide triterpene glycosides, 17‐dehydroxyholothurinoside A (1) and griseaside A (2), were isolated from the sea cucumber Holothuria grisea. Their structures were elucidated by spectroscopic methods, including 2D‐NMR and MS experiments, as well as chemical evidence. Compounds 1 and 2 possess the same pentasaccharide moieties but differ slightly in their side chains of the holostane‐type triterpene aglycone. The structures of the two new glycosides were established as (3__β__,12__α__)‐22,25‐epoxy‐3‐{(O‐β‐D‐glucopyranosyl‐(1→4)‐O‐[O‐3‐O‐methyl‐β‐D‐glucopyranosyl‐(1→3)‐O‐β‐D‐glucopyranosyl‐(1→4)‐6‐deoxy‐β‐D‐glucopyranosyl‐(1→2)]‐β‐D‐xylopyranosyl)oxy}‐12,20‐dihydroxylanost‐9(11)‐en‐18‐oic acid γ‐lactone (1) and (3__β__,12__α__)‐3‐{(O‐β‐D‐glucopyranosyl‐(1→4)‐O‐[O‐3‐O‐methyl‐β‐D‐glucopyranosyl‐(1→3)‐O‐β‐D‐glucopyranosyl‐(1→4)‐6‐deoxy‐β‐D‐glucopyranosyl‐(1→2)]‐β‐D‐xylopyranosyl)oxy}‐12,20,22‐trihydroxylanost‐9(11)‐en‐18‐oic acid γ‐lactone (2). The 17‐dehydroxyholothurinoside A (1) and griseaside A (2) exhibited significant cytotoxicity against HL‐60, BEL‐7402, Molt‐4, and A‐549 cancer cell lines.