酚类物质及其化学修饰物抗真菌的构效关系研究
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摘要
本研究选择了果蔬采后难控制的三种致腐病原真菌：引起高温下果蔬迅速软腐
的匍枝根霉（Rhizopus stolonifer）、引起中低温下果蔬软腐的半裸镰刀菌（Fusarium
semitecum）及低温冷藏下的优势病原交链孢（Alternaria alternata）为供试菌，选用
酚类物质及合成一系列酚类物质衍生物共30种为供试药剂，进行药效实验，对药剂
的化学结构与抗菌性能关系进行相关分析，并对其机理做了探讨。结果为：（1）邻
位、对位多元酚，（邻苯二酚，对苯二酚，邻苯三酚）对这三种病原真菌的抑制作用
比一元酚（苯酚）的作用强，间位多元酚（间苯二酚，间苯三酚）的作用最弱。二
元酚作用比对应三元酚强。（2）邻位、对位二元酚中的一个羟基被羧基取代后，其
抑菌性能大大减弱。邻羟基苯甲酸的抑菌性能比对羟基苯甲酸强。（3）对羟基苯甲
酸羧基酯化后，极大地提高了抑菌性能，而邻羟基苯甲酸羧基酯化后，抑菌性能反
而减弱，但随着酯链长度达到5-6个碳原子时，其抗菌性能比邻羟基苯甲酸强。二者
在酯化烷链的碳原子数达到5-6个时，其抑菌性能最强，当酯化烷链的碳原子数超
过7个时（碳链长度≥7）其抗菌性能迅速降低。对羟基苯甲酸酯的抗菌性能比邻羟
基苯甲酸酯的作用强得多。（4）酚（一元酚，二元酚，三元酚）乙酰化后，抑菌性
能发生变化，间位多元酚乙酰化后，抑茵性能增强，其它酚乙酰化后，抑菌性能均
有所下降。（5）在诱导培养基上，匍枝根霉，半裸镰刀菌均能产生多聚半乳糖醛酸
酶（PG），果胶甲酯酶（PME），和纤维素酶（cellulase），在诱导培养基中匍枝根霉
比半裸镰刀菌产的PG，PME高，而半裸镰刀菌比匍枝根霉产的cellulase高。其中含
1％果胶诱导培养基诱导病原菌产生的各酶活性均比含1％CMC诱导物诱导病原菌产的
酶活性高。果胶在诱导病原产PG，PME方面特别显著。（6）苯环上对二元取代物对产
酶表现明显抑制作用，20mg/L的对苯二酚，对羟基苯甲酸丁酯分别对半裸镰刀菌，
匍枝根霉的产酶有明显地抑制，而对酶活性有微弱抑制（7）贮藏实验证明，对羟基
苯甲酸已酯对控制半裸镰刀菌，匍枝根霉，对羟基苯甲酸戊酯对控制交链孢引起的
腐烂有一定的控制。
The tests on effects of phenols and their derivatives were conducted on Rhizopus stolonifer,Fusarium semitecum,A hernaria alternata .The relationship between chemical structure of phenolic compounds and antifungal activity was analysed. The mechanism of antifungal was discussed. These results showed that: (1 )p-polyhydroxyphenolic,opolyhydroxyphenolic(pyrocatechal,hydroquinone,pyrogallol) had better effect than phenol,m-polyhydroxy phenolic(resoricinol ,phloroglucinnol) was the least effect.(2) After one of hydroxyl group of pyrocatedchol and hydroquinone was substituted for carboxyl group , They were greatly less effective against these fungal.(3)After P-hydroxy benzoic acid was esterificated,the antifungal efficiency of it was obviously increased,but salicylic acid had not the same effect .They showed the strongest inhibitory effect when the length of esterification alkyl reached 5-6 carbon atoms.When the number of the carbon atoms exceeded 7(c~7)their antifungal efficiency were rather worse.p-hydroxy ben
zoic acids esters had l~etter effective against the fungal than o-hydroxy benzoic acid esters .After phenol and polyhydroxy phenolic were esterificated,the effect were worse except. M-polyhydroxy phenolic (4) Rhizopus stolorn抐er,Fusarium semitecum were able to produce PG,PME,cellulase in medium.It was found that the CWDE activity(PG,PME,cellulase) produced by the two pathogens was higher in
medium containing 1% pectin than in medium containing 1%CMC.Pectin were able to make the two pathogens produce more PG,PME than CMC.(5) 2Omg/L hydroquinone,Buty-p-hydroxy benzoate respectively inhibit Fusarium
semitecum Rhizopus stolonifer to produce
CWDE(PG,PME,cellulase)(6)Hexyl-p-hydroxy benzoate could contro~ soft rot by Fusarium semitecum and Rhizopus stolonifer,and Heptylic-p-hydroxy benzoate could control soft rot by Alternaria alternata.
的匍枝根霉（Rhizopus stolonifer）、引起中低温下果蔬软腐的半裸镰刀菌（Fusarium
semitecum）及低温冷藏下的优势病原交链孢（Alternaria alternata）为供试菌，选用
酚类物质及合成一系列酚类物质衍生物共30种为供试药剂，进行药效实验，对药剂
的化学结构与抗菌性能关系进行相关分析，并对其机理做了探讨。结果为：（1）邻
位、对位多元酚，（邻苯二酚，对苯二酚，邻苯三酚）对这三种病原真菌的抑制作用
比一元酚（苯酚）的作用强，间位多元酚（间苯二酚，间苯三酚）的作用最弱。二
元酚作用比对应三元酚强。（2）邻位、对位二元酚中的一个羟基被羧基取代后，其
抑菌性能大大减弱。邻羟基苯甲酸的抑菌性能比对羟基苯甲酸强。（3）对羟基苯甲
酸羧基酯化后，极大地提高了抑菌性能，而邻羟基苯甲酸羧基酯化后，抑菌性能反
而减弱，但随着酯链长度达到5-6个碳原子时，其抗菌性能比邻羟基苯甲酸强。二者
在酯化烷链的碳原子数达到5-6个时，其抑菌性能最强，当酯化烷链的碳原子数超
过7个时（碳链长度≥7）其抗菌性能迅速降低。对羟基苯甲酸酯的抗菌性能比邻羟
基苯甲酸酯的作用强得多。（4）酚（一元酚，二元酚，三元酚）乙酰化后，抑菌性
能发生变化，间位多元酚乙酰化后，抑茵性能增强，其它酚乙酰化后，抑菌性能均
有所下降。（5）在诱导培养基上，匍枝根霉，半裸镰刀菌均能产生多聚半乳糖醛酸
酶（PG），果胶甲酯酶（PME），和纤维素酶（cellulase），在诱导培养基中匍枝根霉
比半裸镰刀菌产的PG，PME高，而半裸镰刀菌比匍枝根霉产的cellulase高。其中含
1％果胶诱导培养基诱导病原菌产生的各酶活性均比含1％CMC诱导物诱导病原菌产的
酶活性高。果胶在诱导病原产PG，PME方面特别显著。（6）苯环上对二元取代物对产
酶表现明显抑制作用，20mg/L的对苯二酚，对羟基苯甲酸丁酯分别对半裸镰刀菌，
匍枝根霉的产酶有明显地抑制，而对酶活性有微弱抑制（7）贮藏实验证明，对羟基
苯甲酸已酯对控制半裸镰刀菌，匍枝根霉，对羟基苯甲酸戊酯对控制交链孢引起的
腐烂有一定的控制。
The tests on effects of phenols and their derivatives were conducted on Rhizopus stolonifer,Fusarium semitecum,A hernaria alternata .The relationship between chemical structure of phenolic compounds and antifungal activity was analysed. The mechanism of antifungal was discussed. These results showed that: (1 )p-polyhydroxyphenolic,opolyhydroxyphenolic(pyrocatechal,hydroquinone,pyrogallol) had better effect than phenol,m-polyhydroxy phenolic(resoricinol ,phloroglucinnol) was the least effect.(2) After one of hydroxyl group of pyrocatedchol and hydroquinone was substituted for carboxyl group , They were greatly less effective against these fungal.(3)After P-hydroxy benzoic acid was esterificated,the antifungal efficiency of it was obviously increased,but salicylic acid had not the same effect .They showed the strongest inhibitory effect when the length of esterification alkyl reached 5-6 carbon atoms.When the number of the carbon atoms exceeded 7(c~7)their antifungal efficiency were rather worse.p-hydroxy ben
zoic acids esters had l~etter effective against the fungal than o-hydroxy benzoic acid esters .After phenol and polyhydroxy phenolic were esterificated,the effect were worse except. M-polyhydroxy phenolic (4) Rhizopus stolorn抐er,Fusarium semitecum were able to produce PG,PME,cellulase in medium.It was found that the CWDE activity(PG,PME,cellulase) produced by the two pathogens was higher in
medium containing 1% pectin than in medium containing 1%CMC.Pectin were able to make the two pathogens produce more PG,PME than CMC.(5) 2Omg/L hydroquinone,Buty-p-hydroxy benzoate respectively inhibit Fusarium
semitecum Rhizopus stolonifer to produce
CWDE(PG,PME,cellulase)(6)Hexyl-p-hydroxy benzoate could contro~ soft rot by Fusarium semitecum and Rhizopus stolonifer,and Heptylic-p-hydroxy benzoate could control soft rot by Alternaria alternata.
引文
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11．伞丽萍等，1997，水杨酸保鲜大久保桃初探，食品科学，(7)：61-63
12．李雄彪，1993，植物细胞壁，北京大学出版社
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2．E．吕克著，1988，食品抗菌添加剂性质、应用、效果，上海翻译出版公司
3．陈捷等，1996，酚类物质和代谢对瓜果腐霉菌产生的细胞壁降解酶活性影响，植物病理学报，26(2)：171-176
4．陈捷，1996，植物病理学报，26(1)：55-61
5．陈尚武，1994，新疆农业大学硕士学位论文
6．方仲达编著，1977，植病研究法，农业出版社
7．谷利一，1965，香川大农纪要，18，9
8．蒋传葵等，1982，工具酶活力测定，上海科学技术出版社
9．李大春，1991，南京农业大学硕士学位论文集，19-21
10．李德红，潘瑞炽，1995，水杨酸在植物体内的作用，31(2)：144
11．伞丽萍等，1997，水杨酸保鲜大久保桃初探，食品科学，(7)：61-63
12．李雄彪，1993，植物细胞壁，北京大学出版社
13．刘秀娟，1995，酚类物质对两种潜伏炭疽菌化生长和繁殖影响，真菌学报，14(4)：277-282
14．罗忠录等，1987，哈密瓜贮运保鲜剂筛选的研究，食品科学，(3)：43-46
15．吕翠玲等，1995，常用食品防腐剂抗菌作用的研究，微生物学通报，22(1)：36-41
16．慕立义主编，1991，植物化学保护研究方法，中国农业出版社
17．宁正祥等，1997，食品防腐剂的抗菌机理及构效关系，广州食品工业科技，13卷：1-4
18．宁正祥等，1994，食品科学，(4)：60
19．宁正祥等，1995，应用化学学报
20．山本 出等主编，1990，农药的设计与开发指南(第一册)，化学工业出版社
21．谭龙飞等，1995，酸型防腐剂分子解离度对其抗菌活性影响的研究，食品与机械，(4)：24-26
22．王颖等，1993，毒理学，新疆八一农学院动物医学系药理毒理教研室
23．吴文君编著，1988，植物化学保护实验技术导论，陕西科学技术出版社
24．许遵乐等，有机化学实验，中山大学出版社
25．新疆农业大学化学组编，《有机化学实验》
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