PRODUCTION, ISOLATION AND STRUCTURE DETERMINATION OF A NOVEL BETA-GLUCOSIDASE INHIBITOR, CYCLOPHELLITOL, FROM PHELLINUS SP

被引:147
作者
ATSUMI, S
UMEZAWA, K
IINUMA, H
NAGANAWA, H
NAKAMURA, H
IITAKA, Y
TAKEUCHI, T
机构
[1] Institute of Microbial Chemistry, Shinagawa-ku, Tokyo 141
[2] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223, Kanagawa
[3] Laboratory of Biophysics, School of Pharmaceutical Sciences, Teikyo University, Tsukui-gun, 199-01, Kanagawa, Sagamiko-machi
关键词
D O I
10.7164/antibiotics.43.49
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
In the course of our screening of β-glucosidase inhibitor, a culture filtrate of a mushroom, Phellinus sp. strongly inhibited the enzyme activity. The active substance was isolated through charcoal separation, column chromatography and crystallization. Spectroscopic and crystallographic analysis revealed that it had a novel cyclitol structure, (1S, 2R, 3S, 4R, 5R, 6R)-5-hydroxymethyl-7-oxabicyclo[4,1,0]heptane-2,3,4-triol, and we named it cyclophellitol. It inhibited almond-derived β-glucosidase with an IC50 of 0.8 μg/ml. © 1990, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.
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页码:49 / 53
页数:5
相关论文
共 11 条
[1]  
DETAMA R, 1987, PHARMACOL THERAPEUT, V33, P221
[2]   DETERMINATION OF ABSOLUTE CONFIGURATION AND DELTAF'' VALUES FOR LIGHT-ATOM STRUCTURES [J].
ENGEL, DW .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1972, B 28 (MAY15) :1496-&
[3]   INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE [J].
GRUTERS, RA ;
NEEFJES, JJ ;
TERSMETTE, M ;
DEGOEDE, REY ;
TULP, A ;
HUISMAN, HG ;
MIEDEMA, F ;
PLOEGH, HL .
NATURE, 1987, 330 (6143) :74-77
[4]  
HUMPHRIES MJ, 1986, CANCER RES, V46, P5215
[5]  
INOUE S, 1967, TETRAHEDRON, V23, P2125
[6]  
MAIN P, 1978, MULTAN SYSTEM COMPUT
[7]  
ROE JH, 1955, J BIOL CHEM, V212, P335
[8]   CASTANOSPERMINE, A TETRAHYDROXYLATED ALKALOID THAT INHIBITS BETA-GLUCOSIDASE AND BETA-GLUCOCEREBROSIDASE [J].
SAUL, R ;
CHAMBERS, JP ;
MOLYNEUX, RJ ;
ELBEIN, AD .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1983, 221 (02) :593-597
[9]   INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS SYNCYTIUM FORMATION AND VIRUS-REPLICATION BY CASTANOSPERMINE [J].
WALKER, BD ;
KOWALSKI, M ;
GOH, WC ;
KOZARSKY, K ;
KRIEGER, M ;
ROSEN, C ;
ROHRSCHNEIDER, L ;
HASELTINE, WA ;
SODROSKI, J .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (22) :8120-8124
[10]  
1983, PLUTO CAMBRIDGE CRYS