Triterpene Glycosides from Antarctic Sea Cucumbers. 1. Structure of Liouvillosides A1, A2, A3, B1, and B2 from the Sea Cucumber Staurocucumis liouvillei: New Procedure for Separation of Highly Polar Glycoside Fractions and Taxonomic Revision

被引：34

作者：

Antonov, Alexandr S. ^{[1
]}

Avilov, Sergey A. ^{[1
]}

Kalinovsky, Anatoly I. ^{[1
]}

Anastyuk, Stanislav D. ^{[1
]}

Dmitrenok, Pavel S. ^{[1
]}

Evtushenko, Evgeny V. ^{[1
]}

Kalinin, Vladimir I. ^{[1
]}

Smirnov, Alexey V. ^{[2
]}

Taboada, Sergi ^{[3
]}

Ballesteros, Manuel ^{[3
]}

Avila, Conxita ^{[3
]}

Stonik, Valentin A. ^{[1
]}

机构：

[1] Russian Acad Sci, Far E Div, Pacific Inst Bioorgan Chem, Vladivostok 690022, Russia

[2] Russian Acad Sci, Inst Zool, St Petersburg 199164, Russia

[3] Univ Barcelona, Fac Biol, Dept Anim Biol Invertebrates, E-08028 Barcelona, Spain

来源：

JOURNAL OF NATURAL PRODUCTS | 2008年 / 71卷 / 10期

关键词：

D O I：

10.1021/np800173c

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

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.

引用

页码：1677 / 1685

页数：9

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