Iridoid constituents from the branches of Viburnum chinshanense and their inhibitory effects on α-amylase and α-glucosidase

Jia Chen; Yiyuan Tang; Hongjuan Zhou; Jianhua Shao; Wei Ji; Mengya Yang; Chunchao Zhao

doi:10.1016/j.phytochem.2023.113893

Iridoid constituents from the branches of Viburnum chinshanense and their inhibitory effects on α-amylase and α-glucosidase

Phytochemistry. 2023 Dec:216:113893. doi: 10.1016/j.phytochem.2023.113893. Epub 2023 Oct 10.

Authors

Jia Chen¹, Yiyuan Tang², Hongjuan Zhou³, Jianhua Shao⁴, Wei Ji⁵, Mengya Yang⁶, Chunchao Zhao⁷

Affiliations

¹ Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: chartishchen@hotmail.com.
² Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: 1206901447@qq.com.
³ Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: 2269981433@qq.com.
⁴ Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: jhshao@yzu.edu.cn.
⁵ Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: 2212228711@qq.com.
⁶ Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: 3119329639@qq.com.
⁷ Joint International Research Laboratory of Agriculture and Agri-Product Safety of the Ministry of Education, Yangzhou University, Yangzhou, 225009, China. Electronic address: cczhao@yzu.edu.cn.

PMID: 37820889
DOI: 10.1016/j.phytochem.2023.113893

Abstract

Ten previously undescribed iridoid constituents, viburnshosins A-E (1-5) and viburnshosides A-E (6-10), together with one known analogue (11), were isolated from the branches of Viburnum chinshanense. Their structures were unambiguously elucidated by a comprehensive analysis of 1D and 2D NMR data, together with HRESIMS spectroscopic data. The absolute configurations of compounds 1-10 were assigned by means of the calculated ECD spectra. Interestingly, compounds 2 and 3 are the first iridoids with an unusual C-3-C-7 oxo bridge. Compounds 4, 5, and 10 displayed remarkable inhibitory effects against α-amylase (IC₅₀: 38.42, 37.65, and 21.64 μM, respectively) and α-glucosidase (IC₅₀: 12.97, 19.34, and 25.71 μM, respectively), comparable to those of the positive control acarbose (IC₅₀: 39.75 and 23.66 μM, respectively). The interaction modes of compounds 4 and 10 with two enzymes were analyzed by molecular modeling.

Keywords: Adoxaceae; Iridoid; Viburnum chinshanense; α-Amylase inhibition; α-Glucosidase inhibition.

MeSH terms

Glycoside Hydrolase Inhibitors / chemistry
Iridoids / chemistry
Molecular Structure
Viburnum* / chemistry
Viburnum* / metabolism
alpha-Amylases
alpha-Glucosidases* / metabolism

Substances

alpha-Glucosidases
Iridoids
Glycoside Hydrolase Inhibitors
alpha-Amylases