Journal
JOURNAL OF NATURAL PRODUCTS
Volume 71, Issue 10, Pages 1677-1685Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np800173c
Keywords
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Funding
- Presidium of the Russian Academy of Sciences Molecular and Cell Biology
- President of the Russian Federation [NSH-6491.2006.4]
- RFBR [06-04-96016]
- FEB RAS [06-III-B-05-128, 06-III-A-05-122]
- FEBRAS-UBRAS [06-2Y-0-05-009]
- NATO [CBP.NR.CLG. 992737]
- ECOQUIM from Spain [REN2002-12006-E/ANT, REN2003-00545, CGL2004-03356/ANT]
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Five new triterpene glycosides, liouvillosides A(1) (1), A(2) (2), A(3) (3), B-1 (4), and B-2 (5), have been isolated from the Antarctic sea cucumber Staurocucumis liouviellei along with the known liouvilloside A (6), isolated earlier from the same species, and hemoiedemosides A (7) and B (8), isolated earlier from the Patagonian sea cucumber Hemioedema spectabilis. The isolation was carried out using a new chromatographic procedure including application of ion-pair reversed-phase chromatography followed by chiral chromatography on a cyclodextrin ChiraDex column. The structures of the new glycosides were elucidated using extensive NMR spectroscopy (H-1 and C-13 NMR spectrometry, DEPT, H-1-H-1 COSY, HMBC, HMQC, and NOESY), ESI-FTMS, and CID MS/MS, and chemical transformations. Glycosides 1-3 are disulfated tetraosides and glycosides 4 and 5 are trisulfated tetraosides. Glycosides 2 and 3 contain 3-O-methylquinovose, found for the first time as a natural monosaccharide in sea cucumber glycosides. On the basis of analyses of glycoside structures a taxonomic revision is proposed.
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