HLE-Inhibitory Alkaloids with a Polyketide Skeleton from the Marine-Derived Fungus Coniothyrium cereale

被引:33
作者
Elsebai, Mahmoud Fahmi [1 ,2 ]
Natesan, Lavanya [1 ]
Kehraus, Stefan [1 ]
Mohamed, Ietidal E. [1 ]
Schnakenburg, Gregor [3 ]
Sasse, Florenz [4 ]
Shaaban, Saad [4 ]
Guetschow, Michael [5 ]
Koenig, Gabriele M. [1 ]
机构
[1] Univ Bonn, Inst Pharmaceut Biol, D-53115 Bonn, Germany
[2] Mansoura Univ, Fac Pharm, Dept Pharmacognosy, Mansoura, Egypt
[3] Univ Bonn, Inst Inorgan Chem, Dept Xray Crystallog, D-53121 Bonn, Germany
[4] Helmholtz Ctr Infect Res, Dept Biol Chem, D-38124 Braunschweig, Germany
[5] Univ Bonn, Inst Pharmaceut, D-53121 Bonn, Germany
来源
JOURNAL OF NATURAL PRODUCTS | 2011年 / 74卷 / 10期
关键词
PENICILLIUM-HERQUEI; DEOXYHERQUEINONE; METABOLITES;
D O I
10.1021/np2004227
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The marine endophytic fungus Coniothyrium cereale produces the structurally unusual polyketide-type alkaloids (-)-cereolactam (1) and (-)-cereoaldomine (3), incorporating a lactam and an imine functionality, respectively, as well as the related metabolite (-)-trypethelone (2). Compounds 1 and 3 showed selective inhibition of human leukocyte elastase with IC(50) values of 9.28 and 3.01 mu M, respectively. Compound 2 was found to be inhibitory toward Mycobacterium phlei, Staphylococcus aureus, and Escherichia coli and also cytotoxic against mouse fibroblast cells (IC(50) = 7.5 mu M).
引用
收藏
页码:2282 / 2285
页数:4
相关论文
共 10 条
[1]   METABOLITES PRODUCED BY THE SCLERODERRIS CANKER FUNGUS, GREMMENIELLA-ABIETINA .4. BIOSYNTHETIC-STUDIES [J].
AYER, WA ;
PEDRAS, MS ;
WARD, DE .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (04) :760-764
[2]   Absolute configurations of naturally occurring quinones: Ventilagone and dunnione [J].
Cooke, Raymond G. ;
Ghisalberti, Emilio L. ;
Johnson, Brian L. ;
Raston, Colin L. ;
Skelton, Brian W. ;
White, Allan H. .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2006, 59 (12) :925-930
[3]   Antimicrobial phenalenone derivatives from the marine-derived fungus Coniothyrium cereale [J].
Elsebai, Mahmoud Fahmi ;
Kehraus, Stefan ;
Lindequist, Ulrike ;
Sasse, Florenz ;
Shaaban, Saad ;
Guetschow, Michael ;
Josten, Michaele ;
Sahl, Hans-Georg ;
Koenig, Gabriele M. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) :802-808
[4]   Neutrophil Elastase, Proteinase 3, and Cathepsin G as Therapeutic Targets in Human Diseases [J].
Korkmaz, Brice ;
Horwitz, Marshall S. ;
Jenne, Dieter E. ;
Gauthier, Francis .
PHARMACOLOGICAL REVIEWS, 2010, 62 (04) :726-759
[5]  
MATHEY A, 1980, LIEBIGS ANN CHEM, V5, P779
[6]   ISOLATION OF (-)-DUNNIONE FROM LEAVES OF CALCEOLARIA-INTEGRIFOLIA MURR (FAM SCROPHULARIACEAE) [J].
RUEDI, P ;
EUGSTER, CH .
HELVETICA CHIMICA ACTA, 1977, 60 (03) :945-947
[7]  
Sheldrick G. M., 1997, SHELXL 97
[8]   BIOSYNTHESIS OF DEOXYHERQUEINONE IN PENICILLIUM-HERQUEI FROM [C-13]ACETATE AND [C-13]MALONATE - ASSEMBLY PATTERN OF ACETATE INTO PHENALENONE RING-SYSTEM [J].
SIMPSON, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (07) :258-260
[9]   C-13 NUCLEAR MAGNETIC-RESONANCE STRUCTURAL AND BIOSYNTHETIC-STUDIES ON DEOXYHERQUEINONE AND HERQUEICHRYSIN, PHENALENONE METABOLITES OF PENICILLIUM-HERQUEI [J].
SIMPSON, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (05) :1233-1238
[10]   Three antibacterial naphthoquinone analogues from cultured mycobiont of lichen Astrothelium sp [J].
Sun, Li Yan ;
Liu, Zhen Liang ;
Zhang, Tao ;
Niu, Shu Bin ;
Zhao, Zun Tian .
CHINESE CHEMICAL LETTERS, 2010, 21 (07) :842-845