Oximoaspergillimide, a Fungal Derivative from a Marine Isolate of Aspergillus sp.

被引:17
作者
Cardoso-Martinez, Faviola [1 ]
de la Rosa, Jose M. [1 ]
Diaz-Marrero, Ana R. [1 ]
Darias, Jose [1 ]
D'Croz, Luis [2 ,3 ]
Cerella, Claudia [2 ,4 ]
Diederich, Marc [5 ]
Cueto, Mercedes [1 ]
机构
[1] CSIC, Inst Prod Nat & Agrobiol, Tenerife 38206, Spain
[2] Univ Panama, Dept Biol Marina & Limnol, Panama City, Panama
[3] Smithsonian Trop Res Inst, Balboa, Panama
[4] Hop Kirchberg, Lab Biol Mol & Cellulaire Canc, L-2540 Luxembourg, Luxembourg
[5] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
基金
新加坡国家研究基金会;
关键词
Natural products; Structure elucidation; Alkaloids; Oximes; Antimicrobial activity; Cytotoxicity; SEDIMENT-DERIVED FUNGUS; ALGICOLOUS ISOLATE; METABOLITES; BIOSYNTHESIS; STEROIDS;
D O I
10.1002/ejoc.201403668
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new alkaloid, oximoaspergillimide (1), and the known neohydroxyaspergillic (2) and neoaspergillic (3) acids, have been isolated from the extract of a cultured marine-derived fungus (strain CF07002) identified as a member of the genus Aspergillus. The structure of 1 was determined by interpretation of NMR spectroscopic data, and confirmed by synthesis. The antimicrobial and cytotoxic activities of compounds 1-3 were evaluated.
引用
收藏
页码:2256 / 2261
页数:6
相关论文
共 39 条
[11]   CONFORMATIONAL-ANALYSIS OF KETOXIMES BY APPLICATION OF C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
GENESTE, P ;
DURAND, R ;
KAMENKA, JM ;
BEIERBECK, H ;
MARTINO, R ;
SAUNDERS, JK .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (14) :1940-1946
[12]   NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY - USE OF C-13 SPECTRA TO ESTABLISH CONFIGURATIONS OF OXIMES [J].
HAWKES, GE ;
HERWIG, K ;
ROBERTS, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (08) :1017-1028
[13]   A chemical epigenetics approach for engineering the in situ biosynthesis of a cryptic natural product from Aspergillus niger [J].
Henrikson, Jon C. ;
Hoover, Ashley R. ;
Joyner, P. Matthew ;
Cichewicz, Robert H. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (03) :435-438
[14]   Unraveling the Bastarane and Isobastarane Oximo Amide Configurations and Associated Macrocycle Conformations: Implications of Their Influence on Bioactivities [J].
Inman, Wayne D. ;
Crews, Philip .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (03) :402-410
[15]   Disulfide- and Multisulfide-Containing Metabolites from Marine Organisms [J].
Jiang, Cheng-Shi ;
Mueller, Werner E. G. ;
Schroeder, Heinz C. ;
Guo, Yue-Wei .
CHEMICAL REVIEWS, 2012, 112 (04) :2179-2207
[16]   Copper mediated oxidation of amides to imides by Selectfluor [J].
Jin, Zhuang ;
Xu, Bo ;
Hammond, Gerald B. .
TETRAHEDRON LETTERS, 2011, 52 (16) :1956-1959
[17]   PULCHERRIMIN, THE PIGMENT OF CANDIDA PULCHERRIMA [J].
KLUYVER, AJ ;
VANDERWALT, JP ;
VANTRIET, AJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1953, 39 (07) :583-593
[18]   C-13 NMR STUDY OF ALIPHATIC AMIDES AND OXIMES - SPIN-LATTICE RELAXATION-TIMES AND FAST INTERNAL MOTIONS [J].
LEVY, GC ;
NELSON, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (14) :4897-&
[19]  
Liu D, 2000, J CLIN MICROBIOL, V38, P471
[20]   Synthesis of 1,2-Diketones from β-Keto Nitriles via a Protection-Oxidative-Decyanation-Deprotection Protocol [J].
Liu, Yu ;
Yun, Xiliu ;
Zhang-Negrerie, Daisy ;
Huang, Jianhui ;
Du, Yunfei ;
Zhao, Kang .
SYNTHESIS-STUTTGART, 2011, (18) :2984-2994