Increasing structure diversity of farnesylated chalcones by a fungal aromatic prenyltransferase

Ying Wu; Shiyunhua Qian; Xiang Zhou; Shu-Ming Li; Chun-Mao Yuan; Song Yang; Kang Zhou

doi:10.1016/j.phytochem.2024.114149

Increasing structure diversity of farnesylated chalcones by a fungal aromatic prenyltransferase

Phytochemistry. 2024 May 18:224:114149. doi: 10.1016/j.phytochem.2024.114149. Online ahead of print.

Authors

Ying Wu¹, Shiyunhua Qian¹, Xiang Zhou², Shu-Ming Li³, Chun-Mao Yuan⁴, Song Yang⁵, Kang Zhou⁶

Affiliations

¹ School of Pharmaceutical Sciences, Key Laboratory of Plant Resource Conservation and Germplasm Innovation in Mountainous Region, Ministry of Education, Guizhou University, Guiyang, 550025, China.
² Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, Centre for R&D of Fine Chemicals, Guizhou University, Guiyang, 550025, China.
³ Institut für Pharmazeutische Biologie und Biotechnologie, Fachbereich Pharmazie, Philipps-Universität Marburg, Robert-Koch-Str. 4, Marburg, 35037, Germany.
⁴ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, China. Electronic address: yuanchunmao01@126.com.
⁵ Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, Centre for R&D of Fine Chemicals, Guizhou University, Guiyang, 550025, China. Electronic address: jhzx.msm@gmail.com.
⁶ School of Pharmaceutical Sciences, Key Laboratory of Plant Resource Conservation and Germplasm Innovation in Mountainous Region, Ministry of Education, Guizhou University, Guiyang, 550025, China; State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang, 550014, China. Electronic address: kangzhouzj@126.com.

PMID: 38763314
DOI: 10.1016/j.phytochem.2024.114149

Abstract

Farnesylated chalcones were favored by researchers due to their different biological activities. However, only five naturally occurring farnesylated chalcones were described in the literature until now. Here, the farnesylation of six chalcones by the Aspergillus terreus aromatic prenyltransferase AtaPT was reported. Fourteen monofarnesylated chalcones (1F1-1F5, 2F1-2F3, 3F1, 3F2, 4F1, 4F2, 5F1, 6F1, and 6F2) and a difarnesylated product (2F3) were obtained, enriching the diversity of natural farnesylated chalcones significantly. Ten of them are C-farnesylated products, which complement O-farnesylated chalcones by chemical synthesis. Fourteen products have not been reported prior to this study. Nine of the produced compounds (1F2-1F5, 2F1-2F3, 5F1, and 6F1) exhibited inhibitory effect on α-glucosidase with IC₅₀ values ranging from 24.08 ± 1.44 to 190.0 ± 0.28 μM. Among them, compounds 2F3 with IC₅₀ value at 24.08 ± 1.44 μM and 1F4 with IC₅₀ value at 30.09 ± 0.59 μM showed about 20 times stronger than the positive control acarbose with an IC₅₀ at 536.87 ± 24.25 μM in α-glucosidase inhibitory assays.

Keywords: Enzyme catalysis; Farnesylated chalcones; Farnesylations; Prenyltransferases; α-glucosidase.