Identification and characterization of N9-methyltransferase involved in converting caffeine into non-stimulatory theacrine in tea

Yue-Hong Zhang, Yi-Fang Li, Yongjin Wang, Li Tan, Zhi-Qin Cao, Chao Xie, Guo Xie, Hai-Biao Gong, Wan-Yang Sun, Shu-Hua Ouyang, Wen-Jun Duan, Xiaoyun Lu, Ke Ding, Hiroshi Kurihara, Dan Hu (), Zhi-Min Zhang (), Ikuro Abe () and Rong-Rong He ()
Additional contact information
Yue-Hong Zhang: Jinan University
Yi-Fang Li: Jinan University
Yongjin Wang: Jinan University
Li Tan: Jinan University
Zhi-Qin Cao: Jinan University
Chao Xie: Jinan University
Guo Xie: University of Electronic Science and Technology of China
Hai-Biao Gong: Jinan University
Wan-Yang Sun: Jinan University
Shu-Hua Ouyang: Jinan University
Wen-Jun Duan: Jinan University
Xiaoyun Lu: Jinan University
Ke Ding: Jinan University
Hiroshi Kurihara: Jinan University
Dan Hu: Jinan University
Zhi-Min Zhang: Jinan University
Ikuro Abe: The University of Tokyo
Rong-Rong He: Jinan University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Caffeine is a major component of xanthine alkaloids and commonly consumed in many popular beverages. Due to its occasional side effects, reduction of caffeine in a natural way is of great importance and economic significance. Recent studies reveal that caffeine can be converted into non-stimulatory theacrine in the rare tea plant Camellia assamica var. kucha (Kucha), which involves oxidation at the C8 and methylation at the N9 positions of caffeine. However, the underlying molecular mechanism remains unclear. Here, we identify the theacrine synthase CkTcS from Kucha, which possesses novel N9-methyltransferase activity using 1,3,7-trimethyluric acid but not caffeine as a substrate, confirming that C8 oxidation takes place prior to N9-methylation. The crystal structure of the CkTcS complex reveals the key residues that are required for the N9-methylation, providing insights into how caffeine N-methyltransferases in tea plants have evolved to catalyze regioselective N-methylation through fine tuning of their active sites. These results may guide the future development of decaffeinated drinks.

Date: 2020
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DOI: 10.1038/s41467-020-15324-7

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