Two new phenylethanoid glycosides from Ginkgo biloba leaves and their tyrosinase inhibitory activities

Penghua Shu; Yingying Fei; Junping Li; Anqi Liu; Lingxiang Zhang; Haoying Niu; Wanrong Liu; Xialan Wei; Fugang Xiao; Zhihong Xu

doi:10.1016/j.carres.2020.108059

Two new phenylethanoid glycosides from Ginkgo biloba leaves and their tyrosinase inhibitory activities

Carbohydr Res. 2020 Aug:494:108059. doi: 10.1016/j.carres.2020.108059. Epub 2020 Jun 16.

Authors

Penghua Shu¹, Yingying Fei², Junping Li², Anqi Liu², Lingxiang Zhang², Haoying Niu², Wanrong Liu², Xialan Wei³, Fugang Xiao⁴, Zhihong Xu⁵

Affiliations

¹ School of Chemistry and Chemical Engineering, Xuchang University, Xuchang, China. Electronic address: shupenghua@yeah.net.
² School of Chemistry and Chemical Engineering, Xuchang University, Xuchang, China.
³ School of Information Engineering, Xuchang University, Xuchang, China.
⁴ Food and Bioengineering College, Xuchang University, Xuchang, China.
⁵ School of Chemistry and Chemical Engineering, Xuchang University, Xuchang, China. Electronic address: xuzhihong1980@xcu.edu.cn.

PMID: 32569850
DOI: 10.1016/j.carres.2020.108059

Abstract

Two undescribed phenylethanoid glycosides, Ginkgoside C (1) and D (2), together with ten known glycosides (3-12) were isolated from Ginkgo biloba leaves. Their structures were characterized by physical data analyses such as NMR, HRESIMS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory activities. At a concentration of 25 μM, compounds 2, 4, 5, 6, and 11 showed obvious mushroom tyrosinase inhibition activities, with %inhibition values of 19.12 ± 2.59%, 25.79 ± 1.83%, 16.07 ± 1.07%, 24.46 ± 1.10%, 18.64 ± 3.62%, respectively, with kojic acid used as the positive control (27.50 ± 2.72%).

Keywords: Antioxidants; Ginkgo biloba; Glycosides; Hydrolysis; Tyrosinase.

MeSH terms

Agaricales / enzymology
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Ginkgo biloba / chemistry*
Glycosides / chemistry
Glycosides / isolation & purification
Glycosides / pharmacology*
Molecular Conformation
Monophenol Monooxygenase / antagonists & inhibitors*
Monophenol Monooxygenase / metabolism
Phenylethyl Alcohol / chemistry
Phenylethyl Alcohol / isolation & purification
Phenylethyl Alcohol / pharmacology*
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
Plant Leaves / chemistry

Substances

Enzyme Inhibitors
Glycosides
Plant Extracts
Monophenol Monooxygenase
Phenylethyl Alcohol