Omphalotins B, C and D, nematicidal cyclopeptides from Omphalotus olearius.: Absolute configuration of omphalotin A.

被引:48
作者
Büchel, E
Martini, U
Mayer, A
Anke, H
Sterner, O
机构
[1] Univ Lund, Div Organ Chem 2, S-22100 Lund, Sweden
[2] Univ Kaiserslautern, Lehrbereich Biotechnol, D-67663 Kaiserslautern, Germany
关键词
D O I
10.1016/S0040-4020(98)00209-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The isolation and structure determination by spectroscopic methods of omphalotins B (2a), C (2b) and D (2c), containing oxidised glycine, valine, isoleucine and tryptophan, from extracts of the basidiomycete Omphalotus olearius is described. All amino acids of omphalotin A (1) were shown to have L configuration. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5345 / 5352
页数:8
相关论文
共 11 条
[1]  
ALBERT R, 1990, CHEM STRUCT BIOL, P437
[2]   STEREOCHEMISTRY OF THE 4-HYDROXYISOLEUCINE FROM TRIGONELLA-FOENUM-GRAECUM [J].
ALCOCK, NW ;
CROUT, DHG ;
GREGORIO, MVM ;
LEE, E ;
PIKE, G ;
SAMUEL, CJ .
PHYTOCHEMISTRY, 1989, 28 (07) :1835-1841
[3]  
GIEREN A, 1974, LIEBIGS ANN CHEM, P1561, DOI 10.1002/jlac.197419741004
[4]   OKARAMINE-C, A NEW INSECTICIDAL INDOLE ALKALOID FROM PENICILLIUM-SIMPLICISSIMUM [J].
HAYASHI, H ;
FUJIWARA, T ;
MURAO, S ;
ARAI, M .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (12) :3143-3145
[5]   REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC RESOLUTION OF NON-ESTERIFIED ENANTIOMERIC AMINO-ACIDS BY DERIVATIZATION WITH 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE AND 2,3,4-TRI-O-ACETYL-ALPHA-D-ARABINO-PYRANOSYL ISOTHIOCYANAT [J].
KINOSHITA, T ;
KASAHARA, Y ;
NIMURA, N .
JOURNAL OF CHROMATOGRAPHY, 1981, 210 (01) :77-81
[6]   Himastatin, a new antitumor antibiotic from Streptomyces hygroscopicus .3. Structural elucidation [J].
Leet, JE ;
Schroeder, DR ;
Golik, J ;
Matson, JA ;
Doyle, TW ;
Lam, KS ;
Hill, SE ;
Lee, MS ;
Whitney, JL ;
Krishnan, BS .
JOURNAL OF ANTIBIOTICS, 1996, 49 (03) :299-311
[7]   Omphalotin, a new cyclic peptide with potent nematicidal activity from Omphalotus olearius .1. Fermentation and biological activity [J].
Mayer, A ;
Anke, H ;
Sterner, O .
NATURAL PRODUCT LETTERS, 1997, 10 (01) :25-32
[8]  
NAKAGAWA M, 1981, CHEM PHARM BULL, V29, P1013
[9]   VALID MODEL FOR MECHANISM OF OXIDATION OF TRYPTOPHAN TO FORMYLKYNURENINE - 25 YEARS LATER [J].
NAKAGAWA, M ;
WATANABE, H ;
KODATO, S ;
OKAJIMA, H ;
HINO, T ;
FLIPPEN, JL ;
WITKOP, B .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1977, 74 (11) :4730-4733
[10]   ANTINEOPLASTIC AGENTS .277. ISOLATION AND STRUCTURE OF PHAKELLISTATIN-3 AND ISOPHAKELLISTATIN-3 FROM A REPUBLIC-OF-COMOROS MARINE SPONGE [J].
PETTIT, GR ;
TAN, R ;
HERALD, DL ;
CERNY, RL ;
WILLIAMS, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07) :1593-1595