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Food Chem. 2019 May 15;280:27-33. doi: 10.1016/j.foodchem.2018.12.035. Epub 2018 Dec 16.

Characterization of enzymes specifically producing chiral flavor compounds (R)- and (S)-1-phenylethanol from tea (Camellia sinensis) flowers.

Author information

1
Guangdong Provincial Key Laboratory of Applied Botany & Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, China; College of Advanced Agricultural Sciences, University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
2
Guangdong Provincial Key Laboratory of Applied Botany & Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, China.
3
Guangdong Food and Drug Vocational College, Longdongbei Road 321, Tianhe District, Guangzhou 510520, China.
4
Guangdong Provincial Key Laboratory of Applied Botany & Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, China; College of Advanced Agricultural Sciences, University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. Electronic address: zyyang@scbg.ac.cn.

Abstract

1-Phenylethanol is a chiral flavor compound that has enantiomers, (R)- and (S)-1-phenylethanol, with different flavor properties. Given that isolating these enantiomers from plants is low yielding and costly, enzymatic synthesis presents an alternative approach. However, the genes/enzymes that specifically produce (R)- and (S)-1-phenylethanol in plants are unknown. To identify these enzymes in tea (Camellia sinensis) flowers, 21 short chain dehydrogenase (SDR) genes were isolated from tea flowers, cloned, and functionally characterized. Several recombinant SDRs in Escherichia coli exhibited activity for converting acetophenone to (S)-1-phenylethanol (CsSPESs, >99.0%), while only one SDR produced (R)-1-phenylethanol (CsRPES, 98.6%). A pair of homologue enzymes (CsSPES and CsRPES) showed a strong preference for NADPH cofactor, with optimal enzymatic reaction conditions of 45-55 °C and pH 8.0. Identification of the tea flower-derived gene responsible for specific synthesis of (R)- and (S)-1-phenylethanolsuggests enzymatic synthesis of enantiopure 1-phenylethanol is possible using a plant-derived gene.

KEYWORDS:

1-Phenylethanol; 1-Phenylethanol (PubChem CID: 7409); Acetophenone (PubChem CID: 7410); Aroma; Camellia sinensis; Chiral; Ethyl n-decanoate (PubChem CID: 8048); Short chain dehydrogenase; Tea

PMID:
30642496
DOI:
10.1016/j.foodchem.2018.12.035
[Indexed for MEDLINE]

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