α-Glucosidase inhibition of sesquiterpenoids from the heartwood of Mansonia gagei

Huong Thi Thu Le; Yusuke Hioki; Ade Danova; Van-Kieu Nguyen; Thuc-Huy Duong; Masaki Kita; Warinthorn Chavasiri

doi:10.1016/j.phytochem.2023.113778

α-Glucosidase inhibition of sesquiterpenoids from the heartwood of Mansonia gagei

Phytochemistry. 2023 Sep:213:113778. doi: 10.1016/j.phytochem.2023.113778. Epub 2023 Jun 25.

Authors

Huong Thi Thu Le¹, Yusuke Hioki², Ade Danova³, Van-Kieu Nguyen⁴, Thuc-Huy Duong⁵, Masaki Kita², Warinthorn Chavasiri⁶

Affiliations

¹ Department of Chemistry, Ho Chi Minh City University of Education, 280 an Duong Vuong Street, District 5, Ho Chi Minh City, 700000, Viet Nam. Electronic address: huongltt@hcmue.edu.vn.
² Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya, 464-8601, Japan.
³ Organic Chemistry Division, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, JI. Ganesha 10, Bandung, West Java, 40132, Indonesia.
⁴ Institute of Fundamental and Applied Sciences, Duy Tan University, Ho Chi Minh City, 700000, Viet Nam; Faculty of Natural Sciences, Duy Tan University, Da Nang, 550000, Viet Nam.
⁵ Department of Chemistry, Ho Chi Minh City University of Education, 280 an Duong Vuong Street, District 5, Ho Chi Minh City, 700000, Viet Nam.
⁶ Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand; Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand. Electronic address: warinthorn.c@chula.ac.th.

PMID: 37364707
DOI: 10.1016/j.phytochem.2023.113778

Abstract

Nine undescribed sesquiterpenoids, along with ten known compounds, were isolated from the ethyl acetate extract of Mansonia gagei heartwood. Their structures were determined by spectroscopic data analysis (FTIR, 1D, 2D NMR, and HRESIMS), and their absolute configurations were established by ECD calculation. The isolated compounds were evaluated for their inhibitory effect against α-glucosidase from yeast. The results showed that mansonone U, mansonialactam, heliclactone and mansonone S exhibited exceptionally potent activities when compared to the positive control, acarbose, with IC₅₀ values of 12.38 ± 0.71, 0.20 ± 0.05, 13.12 ± 2.85, and 12.05 ± 1.91 μM, respectively. Among them, mansonialactam possessed the most potent inhibitory activity against yeast α-glucosidase, and it showed an uncompetitive inhibition mode.

Keywords: Mansonia gagei J.R.Drumm. Malvaceae; Sesquiterpenoids; Uncompetitive inhibition; α-Glucosidase inhibitory activity.

MeSH terms

Glycoside Hydrolase Inhibitors / pharmacology
Magnetic Resonance Spectroscopy
Malvaceae* / chemistry
Molecular Structure
Saccharomyces cerevisiae
Sesquiterpenes* / chemistry
Sesquiterpenes* / pharmacology
alpha-Glucosidases

Substances

alpha-Glucosidases
Sesquiterpenes
Glycoside Hydrolase Inhibitors