Plakortides I-L, four new cyclic peroxides from an undescribed Jamaican sponge Plakortis sp (Homosclerophorida, Plakinidae)

被引：34

作者：

Hu, JF

Gao, HF

Kelly, M

Hamann, MT ^{[1
]}

机构：

[1] Univ Mississippi, Sch Pharm, Dept Pharmacognosy, University, MS 38677 USA

[2] Natl Inst Water & Atmospher Res Ltd, Auckland, New Zealand

[3] Univ Mississippi, Sch Pharm, Natl Ctr Dev Nat Prod, University, MS 38677 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 46期

基金：

美国国家卫生研究院;

关键词：

biologically active compounds; marine metabolites; peroxides; stereochemistry;

D O I：

10.1016/S0040-4020(01)00947-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Four new polyketide-derived cyclic peroxides, plakortides I (1), J (2), K (3) and L (4), were isolated from an undescribed sponge of the genus Plakortis collected at Discovery Bay, Jamaica. The structures were elucidated by spectral analysis including the 2D NMR techniques. The relative stereochemistry of the plakortides was established by NOESY NMR experiments. Plakortide 1 (1) represents the first report of a polyketide-derived cyclic peroxide with an alpha,beta -unsarurated ketone moiety in the side chain and exhibits significant antimalarial activity against the W2 Clone of Plasmodium falciparum with an IC50 of 570 ng mL(-1) and a selectivity index of > 8.4. (C) 2001 Elsevier Science Ltd. All rights reserved.

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收藏

页码：9379 / 9383

页数：5

相关论文

共 15 条

[1] New polyketides from the Sponge plakortis sp. [J].

Braekman, JC ;

Daloze, D ;

De Groote, S ;

Fernandes, JB ;

Van Soest, RWM .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (08) :1038-1042

[2] STRUCTURAL AND STEREOCHEMICAL STUDIES ON MARINE NORTERPENE CYCLIC PEROXIDES [J].

CAPON, RJ ;

MACLEOD, JK .

TETRAHEDRON, 1985, 41 (16) :3391-3404

[3] Antileishmanial cyclic peroxides from the Palauan sponge Plakortis aff. angulospiculatus [J].

Compagnone, RS ;

Piña, IC ;

Rangel, HR ;

Dagger, F ;

Suárez, AI ;

Reddy, MVR ;

Faulkner, DJ .

TETRAHEDRON, 1998, 54 (13) :3057-3068

[4] PLAKORTOLIDE, A CYTOTOXIC PEROXYLACTONE FROM A PLAKORTIS SPONGE [J].

DAVIDSON, BS .

TETRAHEDRON LETTERS, 1991, 32 (49) :7167-7170

[5] CYTOTOXIC 5-MEMBERED CYCLIC PEROXIDES FROM A PLAKORTIS SPONGE [J].

DAVIDSON, BS .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6722-6724

[6] 2 NEW BIOACTIVE CYCLIC PEROXIDES FROM THE MARINE SPONGE PLAKORTIS-ANGULOSPICULATUS [J].

GUNASEKERA, SP ;

GUNASEKERA, M ;

GUNAWARDANA, GP ;

MCCARTHY, P ;

BURRES, N .

JOURNAL OF NATURAL PRODUCTS, 1990, 53 (03) :669-674

[7] Cyclic polyketide peroxides and acyclic diol analogues from the sponge Plakortis lita [J].

Harrison, B ;

Crews, P .

JOURNAL OF NATURAL PRODUCTS, 1998, 61 (08) :1033-1037

[8] PLAKORTIN, AN ANTIBIOTIC FROM PLAKORTIS-HALICHONDRIOIDES [J].

HIGGS, MD ;

FAULKNER, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) :3454-3457

[9] Plakortides, novel cyclic peroxides from the sponge Plakortis halichondrioides: Activators of cardiac SR-CA(2+)-pumping ATPase [J].

Patil, AD ;

Freyer, AJ ;

Carte, B ;

Johnson, RK ;

Lahouratate, P .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (03) :219-223

[10] New peroxylactones from the Jamaican sponge Plakinastrella onkodes, with inhibitory activity against the AIDS opportunistic parasitic infection Toxoplasma gondii [J].

Perry, TL ;

Dickerson, A ;

Khan, AA ;

Kondru, RK ;

Beratan, DN ;

Wipf, P ;

Kelly, M ;

Hamann, MT .

TETRAHEDRON, 2001, 57 (08) :1483-1487