Novel cyclopropyl diketones and 14-membered macrolides from the soil fungus Hamigera avellanea BCC 17816

被引：30

作者：

Isaka, Masahiko ^{[1
]}

Chinthanom, Panida ^{[1
]}

Veeranondha, Sukitaya ^{[1
]}

Supothina, Sumalee ^{[1
]}

Luangsa-ard, J. Jennifer ^{[1
]}

机构：

[1] Natl Ctr Genet Engn & Biotechnol BIOTEC, Klongluang 12120, Pathumthani, Thailand

来源：

TETRAHEDRON | 2008年 / 64卷 / 49期

关键词：

Hamigera avellanea; Resorcylic acid lactone; Antimalarial activity; Anticancer activity;

D O I：

10.1016/j.tet.2008.09.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two novel cyclopropyl diketones, hamavellone A (1) and B (2), and two new 14-membered nonaketide macrolactones, hamigeromycin A (3) and B (4), together with six known compounds, 89-250904-F1 (radicicol analogue A, 5), pseurotin A (6), emodin (7), omega-hydroxyemodin (8), and emodin bianthrones (9 and 10) were isolated from the soil fungus Hamigera avellanea BCC 17816. The structures of the new compounds were defined by analysis of NMR and MS data. The absolute stereochemistry of 3 was addressed by chemical correlation to 5. Hamavellone B (2) exhibited antimalarial activity with an IC50 of 5.2 mu g/nnL, whereas it also showed comparable cytotoxicity. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：11028 / 11033

页数：6

共 23 条

[1]

ABEGAZ B, 1988, B CHEM SOC ETHIOPIA, V2, P15

[2] ISOLATION AND STRUCTURE OF PSEUROTIN-A, A MICROBIAL METABOLITE OF PSEUDEUROTIUM-OVALIS STOLK WITH AN UNUSUAL HETEROSPIROCYCLIC SYSTEM [J].

BLOCH, P ;

TAMM, C .

HELVETICA CHIMICA ACTA, 1981, 64 (01) :304-315

[3]

BLOCH P, 1976, HELV CHIM ACTA, V59, P133, DOI 10.1002/hlca.19760590114

[4] Pinpointing pseurotins from a marine-derived Aspergillus as tools for chemical genetics using a synthetic lethality yeast screen [J].

Boot, Claudia M. ;

Gassner, Nadine C. ;

Compton, Jennifer E. ;

Tenney, Karen ;

Tamble, Craig M. ;

Lokey, R. Scott ;

Holman, Theodore R. ;

Crews, Phillip .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (10) :1672-1675

[5] Hamigerone and dihydrohamigerone: Two acetate-derived, antifungal metabolites from Hamigera avellanea [J].

Breinholt, J ;

Kjoer, A ;

Olsen, CE ;

Rassing, BR ;

Rosendahl, CN .

ACTA CHEMICA SCANDINAVICA, 1997, 51 (12) :1241-1244

[6]

BREINHOLT J, 1996, Patent No. 9626199

[7] Improved green fluorescent protein reporter gene-based microplate screening for antituberculosis compounds by utilizing an acetamidase promoter [J].

Changsen, C ;

Franzblau, SG ;

Palittapongarnpim, P .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2003, 47 (12) :3682-3687

[8] Modular synthesis of radicicol a and related resorcylic acid lactones, potent kinase inhibitors [J].

Dakas, Pierre-Yves ;

Barluenga, Sofia ;

Totzke, Frank ;

Zirrgiebel, Ute ;

Winssinger, Nicolas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (36) :6899-6902

[9] QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE [J].

DESJARDINS, RE ;

CANFIELD, CJ ;

HAYNES, JD ;

CHULAY, JD .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :710-718

[10] Nematicidal resorcylides from the aquatic fungus Caryospora callicarpa YMF1.01026 [J].

Dong, Jinyan ;

Zhu, Yanhui ;

Song, Hongchuan ;

Li, Ru ;

He, Hongping ;

Liu, Haiyang ;

Huang, Rong ;

Zhou, Yongping ;

Wang, Le ;

Cao, Yi ;

Zhang, Keqin .

JOURNAL OF CHEMICAL ECOLOGY, 2007, 33 (05) :1115-1126

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