Kulokekahilide-2, a cytotoxic depsipeptide from a cephalaspidean mollusk Philinopsis speciosa

被引：68
作者：
Nakao, Y
Yoshida, WY
Takada, Y
Kimura, J
Yang, L
Mooberry, SL
Scheuer, PJ
机构：
[1] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
[2] Univ Hawaii, Canc Res Ctr Hawaii, Nat Prod Program, Honolulu, HI 96813 USA
[3] Aoyama Gakuin Univ, Coll Sci & Engn, Dept Chem, Sagamihara, Kanagawa 2298558, Japan
来源：
JOURNAL OF NATURAL PRODUCTS | 2004年 / 67卷 / 08期
关键词：
D O I：
10.1021/np049949f
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.
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页码：1332 / 1340
页数：9
相关论文
共 35 条
[1]  
BASHA A, 1977, TETRAHEDRON LETT, V22, P3815
[2]   STRUCTURE ELUCIDATION OF THE ANTIBIOTIC DESERTOMYCIN THROUGH THE USE OF NEW TWO-DIMENSIONAL NMR TECHNIQUES [J].
BAX, A ;
ASZALOS, A ;
DINYA, Z ;
SUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :8056-8063
[3]   1,2-ANTI DIASTEREOSELECTIVE REDUCTION OF 2-ALKYL-3-HYDROXY-KETONES VIA THEIR SILYL ETHERS [J].
BLOCH, R ;
GILBERT, L ;
GIRARD, C .
TETRAHEDRON LETTERS, 1988, 29 (09) :1021-1024
[4]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[5]   2 POLYPROPIONATE METABOLITES FROM THE CEPHALASPIDEAN MOLLUSK PHILINOPSIS-SPECIOSA [J].
COVAL, SJ ;
SCHULTE, GR ;
MATSUMOTO, GK ;
ROLL, DM ;
SCHEUER, PJ .
TETRAHEDRON LETTERS, 1985, 26 (44) :5359-5362
[6]   AN INTRIGUING C-16-ALKADIENONE-SUBSTITUTED 2-PYRIDINE FROM A MARINE MOLLUSK [J].
COVAL, SJ ;
SCHEUER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :3024-3025
[7]   ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE [J].
DANDA, H ;
HANSEN, MM ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :173-181
[8]   A stereochemical model for merged 1,2- and 1,3-asymmetric induction in diastereoselective Mukaiyama aldol addition reactions and related processes [J].
Evans, DA ;
Dart, MJ ;
Duffy, JL ;
Yang, MG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4322-4343
[9]   C-13 NMR CHEMICAL-SHIFT CORRELATIONS IN 1,3-DIOL ACETONIDES - IMPLICATIONS FOR THE STEREOCHEMICAL ASSIGNMENT OF PROPIONATE-DERIVED POLYOLS [J].
EVANS, DA ;
RIEGER, DL ;
GAGE, JR .
TETRAHEDRON LETTERS, 1990, 31 (49) :7099-7100
[10]   ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
BARTROLI, J ;
SHIH, TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129
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