Aporphine alkaloids and a naphthoquinone derivative from the leaves of Phaeanthus lucidus Oliv. and their α-glucosidase inhibitory activity

Passakorn Teerapongpisan; Virayu Suthiphasilp; Pakit Kumboonma; Tharakorn Maneerat; Thidarat Duangyod; Rawiwan Charoensup; Phunrawie Promnart; Surat Laphookhieo

doi:10.1016/j.phytochem.2024.114020

Aporphine alkaloids and a naphthoquinone derivative from the leaves of Phaeanthus lucidus Oliv. and their α-glucosidase inhibitory activity

Phytochemistry. 2024 Apr:220:114020. doi: 10.1016/j.phytochem.2024.114020. Epub 2024 Feb 15.

Authors

Passakorn Teerapongpisan¹, Virayu Suthiphasilp², Pakit Kumboonma³, Tharakorn Maneerat⁴, Thidarat Duangyod⁵, Rawiwan Charoensup⁵, Phunrawie Promnart⁶, Surat Laphookhieo⁷

Affiliations

¹ Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
² Department of Industrial Technology and Innovation Management, Faculty of Science and Technology, Pathumwan Institute of Technology, Bangkok, 10330, Thailand.
³ Department of Applied Chemistry, Faculty of Science and Liberal Arts, Rajamangala University of Technology Isan, Nakhon Ratchasima, 30000, Thailand.
⁴ Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Medicinal Plant Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand.
⁵ Medicinal Plant Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
⁶ School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
⁷ Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Medicinal Plant Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand. Electronic address: surat.lap@mfu.ac.th.

PMID: 38364883
DOI: 10.1016/j.phytochem.2024.114020

Abstract

Three previously undescribed aporphine alkaloids, phaeanthuslucidines E-G, one previously undescribed naphthoquinone derivative, phaeanthusnaphthoquinone, and three known compounds were isolated from an EtOAc extract of the leaves of Phaeanthus lucidus Oliv. The structures of all previously undescribed compounds were established through extensive spectroscopic investigations and high-resolution mass spectroscopy. The 6aR configuration of phaeanthuslucidines E-G was assigned by comparing their ECD spectra and specific rotation values with the reported known compounds. Some isolated compounds were evaluated for their α-glucosidase inhibitory activity. Among these compounds, phaeanthuslucidine E showed the highest α-glucosidase inhibitory activity with an IC₅₀ value of 17.9 ± 0.4 μM. The molecular docking of phaeanthuslucidine E was further studied.

Keywords: Annonaceae; Aporphine alkaloids; Naphthoquinone; Phaeanthus lucidus; α-Glucosidase inhibitory activity.

MeSH terms

Alkaloids* / chemistry
Alkaloids* / pharmacology
Aporphines* / chemistry
Aporphines* / pharmacology
Glycoside Hydrolase Inhibitors / pharmacology
Molecular Docking Simulation
Molecular Structure
alpha-Glucosidases

Substances

alpha-Glucosidases
Alkaloids
Aporphines
Glycoside Hydrolase Inhibitors