Feroxosides A-B, two norlanostane tetraglycosides from tbe Caribbean sponge Ectyoplasia ferox

被引：34

作者：

Campagnuolo, C ^{[1
]}

Fattorusso, E ^{[1
]}

Taglialatela-Scafati, O ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

来源：

TETRAHEDRON | 2001年 / 57卷 / 18期

关键词：

marine metabolites; terpene glycosides; NMR spectroscopy; stereochemistry;

D O I：

10.1016/S0040-4020(01)00287-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Feroxosides A and B, have been isolated from the polar extract of the Caribbean sponge Ectyoplasia ferox. Their structures have been determined to be unusual C-4 nor-lanostane triterpenes glycosylated with a rhamnose containing tetrasaccharide chain, by interpretation of spectral data and chemical degradation. Absolute stereochemistry at C-23 has been determined by application of the modified Mosher method for secondary alcohols. Feroxosides A-B are moderately cytotoxic (IC50 19 mug/mL) against murine monocyte-macrophage cell line. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4049 / 4055

页数：7

共 9 条

[1] Ulososide B, a new unusual norlanostane-triterpene glycoside and its genuine aglycone from the Madagascar sponge Ulosa sp. [J].

Antonov, AS ;

Kalinovsky, AI ;

Stonik, VA .

TETRAHEDRON LETTERS, 1998, 39 (22) :3807-3808

[2]

Cafieri F, 1999, EUR J ORG CHEM, V1999, P231

[3] ERYLOSIDE-E FROM AN ATLANTIC SPONGE ERYLUS-GOFFRILLERI [J].

GULAVITA, NK ;

WRIGHT, AE ;

KELLYBORGES, M ;

LONGLEY, RE ;

YARWOOD, D ;

SILLS, MA .

TETRAHEDRON LETTERS, 1994, 35 (25) :4299-4302

[4] A TRITERPENE TETRASACCHARIDE, FORMOSIDE, FROM THE CARIBBEAN CHORISTIDA SPONGE ERYLUS-FORMOSUS [J].

JASPARS, M ;

CREWS, P .

TETRAHEDRON LETTERS, 1994, 35 (41) :7501-7504

[5]

KOBAYASHI M, 1991, CHEM PHARM BULL, V39, P2867

[6] TUMOR INHIBITORS .82. BRUCEANTIN, A NEW POTENT ANTILEUKEMIC SIMAROUBOLIDE FROM BRUCEA-ANTIDYSENTERICA [J].

KUPCHAN, SM ;

BRITTON, RW ;

ZIEGLER, MF ;

SIGEL, CW .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :178-179

[7] HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[8] Wondosterols A-C, three steroidal glycosides from a Korean marine two-sponge association [J].

Ryu, G ;

Choi, BW ;

Lee, BH ;

Hwang, KH ;

Lee, UC ;

Jeong, DS ;

Lee, NH .

TETRAHEDRON, 1999, 55 (46) :13171-13178

[9] Two new spirostanol saponins from Allium tuberosum [J].

Sang, SM ;

Lao, AN ;

Wang, HC ;

Chen, ZL .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (07) :1028-1029

← 1 →