QUANTITATIVE-ANALYSIS OF THE ANTIMICROBIAL ACTIVITY AND MEMBRANE-PERTURBATION POTENCY OF ANTIFOULING PARASUBSTITUTED ALKYLPHENOLS

被引:5
作者
ETOH, H [1 ]
BAN, N [1 ]
FUJIYOSHI, J [1 ]
MURAYAMA, N [1 ]
SUGIYAMA, K [1 ]
WATANABE, N [1 ]
SAKATA, K [1 ]
INA, K [1 ]
MIYOSHI, H [1 ]
IWAMURA, H [1 ]
机构
[1] KYOTO UNIV, DEPT AGR CHEM, SAKYO KU, KYOTO 606, JAPAN
关键词
D O I
10.1271/bbb.58.467
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
To better understand the antifouling action of para-substituted phenolic compounds, the antimicrobial activity, which is known to be related to the antifouling activity, was examined with Trychophyton mentagrophytes. The effect of phenolic compounds on mitochondrial swelling was also investigated to elucidate their membrane-perturbation action. The variation of each activity was quantitatively analyzed by a regression analysis, using hydrophobic substituent parameter pi. Each activity varied parabolically with increasing hydrophobicity of the para-substituent, the optimum pi value being ca. 3.5-4.0. The introduction of a bulky substituent to the ortho position resulted in a drastic decrease in each activity. It is therefore likely that the antimicrobial activity is due to perturbation of the membrane structure. Considering the good correlation between the antifouling and antimicrobial activities of para-substituted phenols, the antifouling activity is assumed to be related to perturbation of the membrane structure and/or function.
引用
收藏
页码:467 / 469
页数:3
相关论文
共 13 条
[1]  
BEATRICE MC, 1980, J BIOL CHEM, V255, P8663
[2]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[3]   RHO-SIGMA-PI ANALYSIS . METHOD FOR CORRELATION OF BIOLOGICAL ACTIVITY + CHEMICAL STRUCTURE [J].
HANSCH, C ;
FUJITA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) :1616-&
[4]   AROMATIC SUBSTITUENT CONSTANTS FOR STRUCTURE-ACTIVITY CORRELATIONS [J].
HANSCH, C ;
LEO, A ;
UNGER, SH ;
KIM, KH ;
NIKAITANI, D ;
LIEN, EJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (11) :1207-1216
[5]  
Hansch C., 1979, SUBSTITUENT CONSTANT
[6]   STRUCTURE OF RESINOSIDES FROM EUCALYPTUS-RESINIFERA AS REPELLENTS AGAINST THE BLUE MUSSEL, MYTILUS-EDULIS [J].
HYODO, S ;
ETOH, H ;
YAMASHITA, N ;
SAKATA, K ;
INA, K .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1992, 56 (01) :138-138
[7]   AN IMPROVED ASSAY-METHOD FOR ANTIFOULING SUBSTANCES USING THE BLUE MUSSEL, MYTILUS-EDULIS [J].
INA, K ;
TAKASAWA, R ;
YAGI, A ;
YAMASHITA, N ;
ETOH, H ;
SAKATA, K .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (12) :3319-3321
[8]   INTERACTION OF ALKYL AMMONIUM DERIVATIVES WITH RED-CELLS - HEMOLYSIS AND SODIUM-PUMP INHIBITION STUDIES [J].
KLEIN, RA ;
ELLORY, JC .
JOURNAL OF MEMBRANE BIOLOGY, 1980, 55 (02) :123-131
[9]   ENZYMIC HYDROLYSIS OF ADENOSINE TRIPHOSPHATE BY LIVER MITOCHONDRIA .1. ACTIVITIES AT DIFFERENT PH VALUES [J].
MYERS, DK ;
SLATER, EC .
BIOCHEMICAL JOURNAL, 1957, 67 :558-572
[10]  
PRINGLE MJ, 1981, MOL PHARMACOL, V19, P49