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

被引：47

作者：

Aiello, Anna

Fattorusso, Ernesto

Giordano, Antonella

Menna, Marialuisa

Navarrete, Carmen

Munoz, Eduardo

机构：

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

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 08期

关键词：

marine natural products; amino alcohols; cytotoxic compounds; ascidians;

D O I：

10.1016/j.bmc.2007.02.015

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The chemical investigation of the Mediterranean ascidian Clavelina phlegraea has led to the isolation of six new 2-amino-3-alkanol derivatives, clavaminols A-F (1-6). Their stereo structures were established by analysis of spectroscopic data and chemical conversion. Clavaminols A, B, C, and F were tested for their cytotoxic and pro-apoptotic properties and clavaminol A was shown to be the more potent cytotoxic compound of this series inducing cell death through activation of the apoptotic machinery. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：2920 / 2926

页数：7

相关论文

共 16 条

[1] Cyclin-dependent kinase-1: linking apoptosis to cell cycle and mitotic catastrophe [J].

Castedo, M ;

Perfettini, JL ;

Roumier, T ;

Kroemer, G .

CELL DEATH AND DIFFERENTIATION, 2002, 9 (12) :1287-1293

[2] 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

[3] 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

[4] 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

[5]

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

[6] Control of apoptotic DNA degradation [J].

Ferri, KF ;

Kroemer, G .

NATURE CELL BIOLOGY, 2000, 2 (04) :E63-E64

[7] 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

[8] 2 EPIMERIC ALIPHATIC AMINO-ALCOHOLS FROM A SPONGE, XESTOSPONGIA SP [J].

GULAVITA, NK ;

SCHEUER, PJ .

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

[9] 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

[10] CRUCIGASTERINS, NEW POLYUNSATURATED AMINO-ALCOHOLS FROM THE MEDITERRANEAN TUNICATE PSEUDODISTOMA-CRUCIGASTER [J].

JARESERIJMAN, EA ;

BAPAT, CP ;

LITHGOWBERTELLONI, A ;

RINEHART, KL ;

SAKAI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5732-5737