Clavaminols G-N, six new marine sphingoids from the Mediterranean ascidian Clavelina phlegraea

被引：48

作者：

Aiello, Anna ^{[1
]}

Fattorusso, Ernesto ^{[1
]}

Giordano, Antonella ^{[1
]}

Menna, Marialuisa ^{[1
]}

Navarrete, Carmen ^{[2
]}

Munoz, Eduardo ^{[2
]}

机构：

[1] Univ Naples Federico 2, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

[2] Univ Cordoba, Dept Biol Celular Fisiol & Inmunol, E-14004 Cordoba, Spain

来源：

TETRAHEDRON | 2009年 / 65卷 / 22期

关键词：

AMINO-ALCOHOLS; ABSOLUTE-CONFIGURATION; ACYCLIC ALKENES; XESTOSPONGIA SP; SPONGE; BIOSYNTHESIS;

D O I：

10.1016/j.tet.2009.03.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

An exhaustive examination of the chemical constituents of the Mediterranean ascidian Clavelina phlegraea led to the isolation of clavaminols G-N (1-6), a new series of amino alcohols, which expand the family of modified marine sphingoids. Structures of the novel compounds 1-6 have been elucidated by spectroscopic analysis and chemical derivatization: bioactivities of compounds 1-6 have also been investigated and comparison of their pharmacological properties with those of previously isolated clavaminols A-F allowed us to perform an assessment of simple structure-activity relationships. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4384 / 4388

页数：5

共 17 条

[1]

Clavaminols A-F, novel cytotoxic 2-amino-3-alkanols from the ascidian Clavelina phlegraea [J].

Aiello, Anna ;

Fattorusso, Ernesto ;

Giordano, Antonella ;

Menna, Marialuisa ;

Navarrete, Carmen ;

Munoz, Eduardo .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (08) :2920-2926

[2]

Coriacenins: A new class of long alkyl chain amino alcohols from the Mediterranean sponge Clathrina coriacea [J].

Casapullo, A ;

Fontana, A ;

Cimino, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7415-7419

[3]

Haliclonacyclamines A and B, cytotoxic alkaloids from the tropical marine sponge Haliclona sp. [J].

Charan, RD ;

Garson, MJ ;

Brereton, IM ;

Willis, AC ;

Hooper, JNA .

TETRAHEDRON, 1996, 52 (27) :9111-9120

[4]

Antifungal alkyl amino alcohols from the tropical marine sponge Haliclona n. sp. [J].

Clark, RJ ;

Garson, MJ ;

Hooper, JNA .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (12) :1568-1571

[5]

The marine compound spisulosine, an inhibitor of cell proliferation, promotes the disassembly of actin stress fibers [J].

Cuadros, R ;

de Garcini, EM ;

Wandosell, F ;

Faircloth, G ;

Fernández-Sousa, JM ;

Avila, J .

CANCER LETTERS, 2000, 152 (01) :23-29

[6]

(2R,3R,7Z)-2-Aminotetradec-7-ene-1,3-diol, a new amino alcohol from the Caribbean sponge Haliclona vansoesti [J].

Devijver, C ;

Salmoun, N ;

Daloze, D ;

Braekman, JC ;

De Weerdt, WH ;

De Kluijver, MJ ;

Gomez, R .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (07) :978-980

[7]

DORMAN DE, 1971, J ORG CHEM, V36, P2757

[8]

Obscuraminols, new unsaturated amino alcohols from the tunicate Pseudodistoma obscurum:: structure and absolute configuration [J].

Garrido, L ;

Zubía, E ;

Ortega, MJ ;

Naranjo, S ;

Salvá, J .

TETRAHEDRON, 2001, 57 (21) :4579-4588

[9]

2 EPIMERIC ALIPHATIC AMINO-ALCOHOLS FROM A SPONGE, XESTOSPONGIA SP [J].

GULAVITA, NK ;

SCHEUER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :366-369

[10]

C-13 NMR chemical shift prediction of the sp(3) carbon atoms in the alpha position relative to the double bond in acyclic alkenes [J].

Ivanciuc, O ;

Rabine, JP ;

CabrolBass, D ;

Panaye, A ;

Doucet, JP .

JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1997, 37 (03) :587-598

← 1 2 →