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林产化学与工业 ›› 2015, Vol. 35 ›› Issue (6): 33-38.doi: 10.3969/j.issn.0253-2417.2015.06.006

• 研究报告 • 上一篇    下一篇

羧酸桃金娘烷醇酯的合成及抑菌活性研究

廖圣良, 商士斌, 司红燕, 沈明贵, 饶小平, 宋湛谦   

  1. 中国林业科学研究院 林产化学工业研究所;生物质化学利用国家工程实验室;国家林业局 林产化学工程重点开放性实验室;江苏省 生物质能源与材料重点实验室, 江苏 南京 210042
  • 收稿日期:2014-10-28 出版日期:2015-12-25 发布日期:2015-12-28
  • 通讯作者: 宋湛谦,研究员,博士生导师,主要从事天然产物化学研究;E-mail:songzq@hotmail.com E-mail:songzq@hotmail.com
  • 作者简介:廖圣良(1988—),男,江西赣州人,博士生,主要研究方向为天然资源化学与利用
  • 基金资助:
    国家自然科学基金云南联合基金项目(U1202265)

Synthesis and Antibacterial Activities of Carboxylic Myrtanyl Esters

LIAO Sheng-liang, SHANG Shi-bin, SI Hong-yan, SHEN Ming-gui, RAO Xiao-ping, SONG Zhan-qian   

  1. Institute of Chemical Industry of Forest Products, CAF; National Engineering Lab.for Biomass Chemical Utilization; Key and Open Lab.of Forest Chemical Engineering, SFA;Key Lab.of Biomass Energy and Material, Jiangsu Province, Nanjing 210042, China
  • Received:2014-10-28 Online:2015-12-25 Published:2015-12-28

摘要: β-蒎烯为原料,经硼氢化氧化反应合成了桃金娘烷醇,桃金娘烷醇与羧酸在N,N'-二环己基碳酰亚胺/4-二甲氨基吡啶(DCC/DMAP)的催化作用下反应,生成了8个羧酸桃金娘烷醇酯新化合物:乙酸桃金娘烷醇酯(4a)、丙酸桃金娘烷醇酯(4b)、正丁酸桃金娘烷醇酯(4c)、正戊酸桃金娘烷醇酯(4d)、环己烷羧酸桃金娘烷醇酯(4e)、苯甲酸桃金娘烷醇酯(4f)、对甲苯甲酸桃金娘烷醇酯(4g)、对甲氧基苯甲酸桃金娘烷醇酯(4h)。借助FT-IR、1H NMR和ESI-MS对产物进行了结构表征,通过琼脂稀释法对所合成的化合物进行了抑菌活性测试。结果表明,在该系列羧酸桃金娘烷醇酯中,化合物4b、4c、4f、4g4h对革兰氏阳性菌金黄色葡萄球菌(Staphylococcus aureus)具有一定的抑菌活性,最小抑菌浓度(MIC)为256 mg/L,化合物4a、4b、4c4e对革兰氏阴性菌大肠埃希氏菌(Escherichia coli)具有抑菌活性,MIC为128~256 mg/L。其中,化合物4aE.coli的MIC为128 mg/L 与新洁尔灭相当。相对于原料β-蒎烯和中间体桃金娘烷醇而言,该系列酯类化合物在抑菌活性上具有一定的提升。

关键词: 松节油, β-蒎烯, 桃金娘烷醇, 酯类, 抑菌

Abstract: Myrtanol was prepared via hydroboration-oxidation reaction from β-pinene, then eight novel carboxylic myrtanyl esters (myrtanyl acetate(4a), myrtanyl propionate(4b), myrtanyl butyrate(4c), myrtanyl valerate(4d), myrtanyl cyclohexanecarboxylate(4e), myrtanyl benzoate(4f), myrtanyl p-methylbenzoate(4g) and myrtanyl p-methoxybenzoate(4h) were obtained through the reaction of myrtanol and carboxylic acids using N, N'-dicyclohexylcarbodiimide/dimethylaminopyridine (DCC/DMAP) as catalyst.Structure characterizations were achieved by FT-IR, 1H NMR and ESI-MS.Antibacterial activity assays were carried out by agar dilution method.The results showed that compounds 4b, 4c, 4f, 4g and 4h exhibited inhibitory activities (MIC was 256 mg/L) against the Gram positive bacterial Staphylococcus aureus, and compounds 4a, 4b, 4c and 4e exhibited inhibitory activities (MICs were ranged from 128 to 256 mg/L) against the Gram negative bacterial Escherichia coli.more importantly.Compound 4a showed comparable activity (MIC was 128 mg/L) to that of bromogeramine against E.coli.Comparing with the starting compound β-pinene and the intermediate myrtanol, this series of esters showed better antibacterial activities.

Key words: turpentine, β-pinene, myrtanol, ester, antibacterial

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