Briarellins J-P and polyanthellin A:: New eunicellin-based diterpenes from the gorgonian coral Briareum polyanthes and their antimalarial activity

被引：54

作者：

Ospina, CA

Rodríguez, AD

Ortega-Barria, E

Capson, TL

机构：

[1] Univ Puerto Rico, Dept Chem, Rio Piedras, PR 00931 USA

[2] Florida State Univ, Cell & Mol Biol Pathogens Unit, Inst Trop Med & Hlth Sci, Balboa, Panama

[3] Smithsonian Trop Res Inst, Balboa, Ancon, Panama

来源：

JOURNAL OF NATURAL PRODUCTS | 2003年 / 66卷 / 03期

关键词：

D O I：

10.1021/np0204500

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A new chemical study of the hexane extract of the gorgonian Briareum polyanthes collected in Puerto Rico afforded 10 new diterpenes of the eunicellin class, briarellins 1-9 and polyanthellin A (10), along with the known diterpene briarellin D (11). The structures and relative stereochemistry of metabolites 1-10 were assigned on the basis of NMR studies, chemical methods, and comparisons to the spectral properties of 11. A reassessment of prior structural assignment for briarellin A and two known sclerophytin-type diterpenes, 13 and 14, is proposed. Antimalarial tests on 1-6 and 8-12 indicated that they were active against Plasmodium falciparum.

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页码：357 / 363

页数：7

相关论文

共 31 条

[11] MOLECULAR-STRUCTURES OF THE BRIANTHEINS, NEW INSECTICIDAL DITERPENES FROM BRIAREUM-POLYANTHES [J].

GRODE, SH ;

JAMES, TR ;

CARDELLINA, JH ;

ONAN, KD .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (26) :5203-5207

[12] Synthetic approach to analogues of the original structure of sclerophytin A [J].

Jung, ME ;

Pontillo, J .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) :6848-6851

[13] A general strategy for the synthesis of cladiellin diterpenes: Enantioselective total syntheses of 6-acetoxycladiell-7(16),11-dien-3-ol (deacetoxyalcyonin acetate), cladiell-11-ene-3,6,7-triol, sclerophytin A, and the initially purported structure of sclerophytin A [J].

MacMillan, DWC ;

Overman, LE ;

Pennington, LD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9033-9044

[14]

Mancini I, 2000, HELV CHIM ACTA, V83, P1561, DOI 10.1002/1522-2675(20000705)83:7<1561::AID-HLCA1561>3.0.CO

[15]

2-H

[16] Chemical inhibitors of cyclin-dependent kinases [J].

Meijer, L .

TRENDS IN CELL BIOLOGY, 1996, 6 (10) :393-397

[17] APPLICATION OF 2-DIMENSIONAL NMR-SPECTROSCOPY IN THE STRUCTURAL DETERMINATION OF MARINE NATURAL-PRODUCTS - ISOLATION AND TOTAL STRUCTURAL ASSIGNMENT OF 4-DEOXYASBESTININ DITERPENES FROM THE CARIBBEAN GORGINIAN BRIAREUM-ASBESTINUM [J].

MORALES, JJ ;

LORENZO, D ;

RODRIGUEZ, AD .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (05) :1368-1382

[18] Total synthesis of the supposed structure of (-)-sclerophytin A and an improved route to (-)-7-deacetoxyalcyonin acetate [J].

Overman, LE ;

Pennington, LD .

ORGANIC LETTERS, 2000, 2 (17) :2683-2686

[19] Synthesis of the alleged structure of sclerophytin A. The setting of two oxygen bridges within the fused cyclodecanol B ring is not nature's way [J].

Paquette, LA ;

Moradei, OM ;

Bernardelli, P ;

Lange, T .

ORGANIC LETTERS, 2000, 2 (13) :1875-1878

[20] NEW BRIAREIN DITERPENES FROM THE CARIBBEAN GORGONIANS ERYTHROPODIUM-CARIBAEORUM AND BRIAREUM SP [J].

PORDESIMO, EO ;

SCHMITZ, FJ ;

CIERESZKO, LS ;

HOSSAIN, MB ;

VANDERHELM, D .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2344-2357

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