Gagones A-F: Six prenylated chalcones from the heartwood of Mansonia gagei

Huong Thi Thu Le; Lam H Nguyen; Tuan H Nguyen; Van-Kieu Nguyen; Ade Danova; Thanh N Truong; Warinthorn Chavasiri

doi:10.1016/j.phytochem.2022.113516

Gagones A-F: Six prenylated chalcones from the heartwood of Mansonia gagei

Phytochemistry. 2023 Feb:206:113516. doi: 10.1016/j.phytochem.2022.113516. Epub 2022 Nov 15.

Authors

Huong Thi Thu Le¹, Lam H Nguyen², Tuan H Nguyen³, Van-Kieu Nguyen⁴, Ade Danova⁵, Thanh N Truong⁶, Warinthorn Chavasiri⁷

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 Institute for Computational Science and Technology, Ho Chi Minh City, 700000, Viet Nam.
³ Faculty of Chemical Engineering, Ho Chi Minh City University of Technology, 268 Ly Thuong Kiet Street, District 10, Ho Chi Minh City, 700000, Viet Nam.
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 Organic Chemistry Division, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, JI. Ganesha 10, Bandung, West Java, 40132, Indonesia.
⁶ Department of Chemistry, University of Utah, Salt Lake City, UT, 84112, USA.
⁷ Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand. Electronic address: warinthorn.c@chula.ac.th.

PMID: 36395879
DOI: 10.1016/j.phytochem.2022.113516

Abstract

Six undescribed prenylated chalcones gagones A-F were isolated from the acetone fraction of Mansonia gagei heartwood. Their structures were unambiguously established based on spectroscopic analysis (HRESIMS, 1D and 2D NMR), as well as comparison to literature data. Their absolute configurations were elucidated using DP4 and electronic circular dichroism calculations. Isolated compounds were evaluated for their inhibitory activity against α-glucosidase and DPPH assay. All of the tested compounds exhibited better activity than that of acarbose (IC₅₀ 93.6 ± 0.5 μM). Among them, gagone D exhibited the highest α-glucosidase inhibitory with the IC₅₀ value of 3.6 ± 0.4 μM. For antioxidant activity, gagones A-C, and E showed more active than that of ascorbic acid (IC₅₀ 30.2 ± 0.5 μM) with the IC₅₀ values of 13.2 ± 0.7, 20.1 ± 0.4, 19.3 ± 0.5 and 12.8 ± 0.2 μM, respectively.

Keywords: Antioxidant; Calculated NMR and ECD; Mansonia gagei J.R.Drumm. Malvaceae; Prenylated chalcones; α-Glucosidase inhibitory activity.

MeSH terms

Chalcones* / pharmacology
Magnetic Resonance Spectroscopy
Malvaceae* / chemistry
Molecular Structure
alpha-Glucosidases

Substances

Chalcones
alpha-Glucosidases