Enzymatic synthesis of caffeic acid phenethyl ester analogues in ionic liquid

被引：40

作者：

Kurata, Atsushi ^{[1
]}

Kitamura, Yuki ^{[1
]}

Irie, Shiori ^{[1
]}

Takemoto, Shintaro ^{[1
]}

Akai, Yoshiaki ^{[1
]}

Hirota, Yoshitaka ^{[1
]}

Fujita, Tokio ^{[1
]}

Iwai, Kazuya ^{[2
]}

Furusawa, Mina ^{[2
]}

Kishimoto, Noriaki ^{[1
]}

机构：

[1] Kinki Univ, Grad Sch Appl Biol Chem, Nara 6318505, Japan

[2] UCC Ueshima Coffee Co Ltd, R&D Ctr, Takatsuki, Osaka 5690036, Japan

来源：

JOURNAL OF BIOTECHNOLOGY | 2010年 / 148卷 / 2-3期

关键词：

Caffeic acid phenethyl ester analogue; Ionic liquid; Microbial lipase; Transesterification; Antiproliferative activity; LIPASE-CATALYZED TRANSESTERIFICATION; TRANSFORMATIONS; ANTIOXIDANT; INHIBITORS; APOPTOSIS; PROPOLIS; CELLS;

D O I：

10.1016/j.jbiotec.2010.05.007

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：

An efficient procedure for transesterification of methyl caffeate was developed to produce caffeic acid phenethyl ester analogues with Candida antarctica lipase B using an ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, as a solvent. The system provided 48.8 mM 2-cyclohexylethyl caffeate and 46.9 mM 3-cyclohexylpropyl caffeate with conversion yields of 97.6% and 93.8%, respectively. Reusability of the system was investigated, and the yield of 4-phenylbutyl caffeate was increased from 30.4 to 45.7 mM when the transesterification was carried out under reduced pressure to remove a by-product, methanol. Additionally, we showed that both 2-cyclohexylethyl caffeate and 3-cyclohexylpropyl caffeate exhibit strong antiproliferative activities, which are comparable to that of 5-fluorouracil by MTT assay. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：133 / 138

页数：6

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