Triterpenoids and meroterpenoids with α-glucosidase inhibitory activities from the fruiting bodies of Ganoderma australe

Jiao-Cen Guo; Li Yang; Qing-Yun Ma; Ya-Zhe Ge; Fan-Dong Kong; Li-Man Zhou; Fei Zhang; Qing-Yi Xie; Zhi-Fang Yu; Hao-Fu Dai; You-Xing Zhao

doi:10.1016/j.bioorg.2021.105448

Triterpenoids and meroterpenoids with α-glucosidase inhibitory activities from the fruiting bodies of Ganoderma australe

Bioorg Chem. 2021 Dec:117:105448. doi: 10.1016/j.bioorg.2021.105448. Epub 2021 Oct 22.

Authors

Jiao-Cen Guo¹, Li Yang¹, Qing-Yun Ma¹, Ya-Zhe Ge², Fan-Dong Kong³, Li-Man Zhou³, Fei Zhang¹, Qing-Yi Xie¹, Zhi-Fang Yu⁴, Hao-Fu Dai⁵, You-Xing Zhao⁶

Affiliations

¹ Haikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, CATAS, Haikou 571101, China.
² Haikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, CATAS, Haikou 571101, China; College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China.
³ Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, School of Chemistry and Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, China.
⁴ College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. Electronic address: yuzhifang@njau.edu.cn.
⁵ Hainan Academy of Tropical Agricultural Resource, CATAS, Haikou 571101, China. Electronic address: daihaofu@itbb.org.cn.
⁶ Haikou Key Laboratory for Research and Utilization of Tropical Natural Products, Institute of Tropical Bioscience and Biotechnology, CATAS, Haikou 571101, China. Electronic address: zhaoyouxing@itbb.org.cn.

PMID: 34736135
DOI: 10.1016/j.bioorg.2021.105448

Abstract

Macrofungi Ganoderma is a valuable medicinal fungus resource for human health and longevity in China. In this study, ten undescribed compounds including seven lostane-type triterpenoids, ganodaustralic acids A ∼ G (1-7), one pair of meroterpenoid enantiomers, (-)-6'-O-ethyllingzhiol (8) and (+)-6'-O-ethyllingzhiol (9), and one polyhydroxylated sterol, 3-O-acetyl-fomentarol C (10), together with eight known compounds (11-18), were isolated from the fruiting bodies of Ganoderma australe. The structures of the new compounds were elucidated by extensive spectroscopic analysis as well as NMR and electronic circular dichroism (ECD) calculations. Compounds 4, 8, 9, and 12 showed significant α-glucosidase inhibitory activities with IC₅₀ values in the range of 4.1-11.7 μM, which were superior to that of positive control acarbose (213 μM). Only compound 7 exhibited weak cytotoxicity against SGC-7901 cells.

Keywords: Ganoderma australe; Meroterpenoids; Triterpenoids; α-glucosidase inhibitory activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Fruiting Bodies, Fungal / chemistry
Ganoderma / chemistry*
Glycoside Hydrolase Inhibitors / chemistry
Glycoside Hydrolase Inhibitors / isolation & purification
Glycoside Hydrolase Inhibitors / pharmacology*
Humans
Molecular Structure
Structure-Activity Relationship
Terpenes / chemistry
Terpenes / isolation & purification
Terpenes / pharmacology*
alpha-Glucosidases / metabolism*

Substances

Antineoplastic Agents
Glycoside Hydrolase Inhibitors
Terpenes
alpha-Glucosidases

Supplementary concepts

Ganoderma australe