Novel methylated flavoalkaloids from Echa 1 green tea inhibit fat accumulation and enhance stress resistance in Caenorhabditis elegans

Chen-Hui Chen; Jing-Ya Yu; Zi Yang; Jia-Ping Ke; Yan Qi; Yi Yang; Biao Gao; Guangmin Yao; Guan-Hu Bao

doi:10.1016/j.foodchem.2023.135643

Novel methylated flavoalkaloids from Echa 1 green tea inhibit fat accumulation and enhance stress resistance in Caenorhabditis elegans

Food Chem. 2023 Jul 1:413:135643. doi: 10.1016/j.foodchem.2023.135643. Epub 2023 Feb 8.

Authors

Chen-Hui Chen¹, Jing-Ya Yu², Zi Yang³, Jia-Ping Ke⁴, Yan Qi⁵, Yi Yang⁶, Biao Gao⁷, Guangmin Yao⁸, Guan-Hu Bao⁹

Affiliations

¹ Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: 2826156094@qq.com.
² Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: 1012990702@qq.com.
³ Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: 544597115@qq.com.
⁴ Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: 705180175@qq.com.
⁵ Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: 1985123561@qq.com.
⁶ Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: 1072692038@qq.com.
⁷ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: 276794932@qq.com.
⁸ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: gyap@mail.hust.edu.cn.
⁹ Natural Products Laboratory, International Joint Laboratory of Tea Chemistry and Healthy Effects, State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China. Electronic address: baoguanhu@ahau.edu.cn.

PMID: 36773353
DOI: 10.1016/j.foodchem.2023.135643

Abstract

Methylation is a common structural modification of catechins in tea, which can improve the bioavailability of catechins. Flavoalkaloids are catechin derivatives with a nitrogen containing five-membered ring at the C-6 or C-8 position. Here we isolated three new methylated flavoalkaloids from Echa 1 green tea (Camellia sinensis cv. Echa 1) and synthesized another four new methylated flavoalkaloids. The structures of the new ester-type methylated catechins (etmc)-pyrrolidinone A-G (1-7) were elucidated by various spectroscopic techniques, including nuclear magnetic resonance (NMR), optical rotation, infrared, UV-vis, experimental and calculated circular dichroism (CD) spectra, and high-resolution mass. Among them, 6 and 7 showed the strongest α-glucosidase inhibitory activity and significantly lowered lipid content of Caenorhabditis elegans with 73.50 and 67.39% inhibition rate, respectively. Meanwhile, 6 and 7 also exhibited strong antioxidant activity in vitro and stress resistance to heat, oxidative stress, and UV irradiation in nematodes.

Keywords: (D, L)-4-chlorophenylalanine (PubChem CID4652); (l)-ascorbic acid (PubChem CID54670067); (–)-Epigallocatechin gallate (EGCG, PubChem CID65064); (–)-epicatechin gallate (ECG, PubChem CID107905); Anti-obesity; Antiaging; Camellia sinensis; Methylated catechins; N, N-dimethylformamide (DMF, PubChem CID6228); N-ethyl-2-pyrrolidinone; acarbose (PubChem CID41774); dimethyl sulfate (DMS, PubChem CID6497); iodomethane (CH(3)I, PubChem CID6328); l-theanine (PubChem CID439378); orlistat (PubChem CID3034010).

MeSH terms

Animals
Antioxidants
Caenorhabditis elegans
Camellia sinensis* / chemistry
Catechin*
Tea / chemistry

Substances

Tea
Catechin
Antioxidants