AGELASPHINS, NOVEL ANTITUMOR AND IMMUNOSTIMULATORY CEREBROSIDES FROM THE MARINE SPONGE AGELAS-MAURITIANUS

被引：378

作者：

NATORI, T

MORITA, M

AKIMOTO, K

KOEZUKA, Y

机构：

[1] Pharmaceutical Research Laboratory, Kirin Brewery Co., Ltd., Takasaki, Gunma, 370-12

来源：

TETRAHEDRON | 1994年 / 50卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)86991-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New glycosphingolipids, named agelasphins (1-8), have been isolated by antitumor and immunostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mauritianus. Strongly active agents in agelasphins had characteristic ol-galactosylceramide structures, the isolation of which from natural products has not previously been reported. The absolute configurations of agelasphins were elucidated by the total synthesis.

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页码：2771 / 2784

页数：14

相关论文

共 15 条

[1] SYNTHESIS AND STEREOCHEMISTRY OF AGELASPHIN-9B [J].

AKIMOTO, K ;

NATORI, T ;

MORITA, M .

TETRAHEDRON LETTERS, 1993, 34 (35) :5593-5596

[2] ANTIMICROBIAL METABOLITES FROM A PACIFIC SPONGE, AGELAS SP [J].

CAPON, RJ ;

FAULKNER, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) :1819-1822

[3]

De Haan J.W, 1973, MAGN RESON CHEM, V5, P147, DOI [10.1002/mrc.1270050309, DOI 10.1002/MRC.1270050309]

[4] METHODS FOR METHANOLYSIS OF SPHINGOLIPIDS AND DIRECT DETERMINATION OF LONG-CHAIN BASES BY GAS CHROMATOGRAPHY [J].

GAVER, RC ;

SWEELEY, CC .

JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1965, 42 (04) :294-&

[5]

HIGUCHI R, 1990, LIEBIGS ANN CHEM, P51

[6] GLUCOSYLCERAMIDE HAVING A NOVEL TRI-UNSATURATED LONG-CHAIN BASE FROM THE SPERMATOZOA OF THE STARFISH, ASTERIAS-AMURENSIS [J].

IRIE, A ;

KUBO, H ;

HOSHI, M .

JOURNAL OF BIOCHEMISTRY, 1990, 107 (04) :578-586

[7] CHEMISTRY AND FUNCTIONAL MOIETY OF A FRUITING-INDUCING CEREBROSIDE IN SCHIZOPHYLLUM-COMMUNE [J].

KAWAI, G ;

IKEDA, Y .

BIOCHIMICA ET BIOPHYSICA ACTA, 1983, 754 (03) :243-248

[8] TOTAL SYNTHESIS OF (2S,3S,4R)-N-TETRACOSANOYL-2-AMINO-1,3,4-OCTADECANETRIOL, A CERAMIDE PART OF WHEAT-FLOUR GLYCOSYL CERAMIDES [J].

KOIKE, K ;

NAKAHARA, Y ;

OGAWA, T .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (03) :663-667

[9] A HIGHLY STEREOSELECTIVE SYNTHESIS OF 2(S), 3(R), 4E- AND 2(S), 3(R), 4Z-N-TETRACOSANOYLSPHINGENINE FROM D-GLUCOSE .41. [J].

KOIKE, K ;

NUMATA, M ;

SUGIMOTO, M ;

NAKAHARA, Y ;

OGAWA, T .

CARBOHYDRATE RESEARCH, 1986, 158 :113-123

[10] AN EFFICIENT METHOD FOR GLUCOSYLATION OF HYDROXY COMPOUNDS USING GLUCOPYRANOSYL FLUORIDE [J].

MUKAIYAMA, T ;

MURAI, Y ;

SHODA, S .

CHEMISTRY LETTERS, 1981, (03) :431-432