Derrisrobustones A-D, isoflavones from the twig extract of Derris robusta (DC.) Benth. and their α-glucosidase inhibitory activity.

Cholpisut Tantapakul, Virayu Suthiphasilp, Apirak Payaka, Boonyanoot Chaiyosang, David J Harding, Worrapong Phuphong, Sarawut Tontapha, Surat Laphookhieo

Journal: Phytochemistry 2022;198():113168

PMID: 35331731

Full Text on Elsevier Science View on PubMed

Abstract

Three previously undescribed isoflavones, derrisrobustones A-C, and a previously undescribed natural isoflavone, derrisrobustone D, along with eight known isoflavones, were isolated from the twig extract of Derris robusta (DC.) Benth. All structures were identified by extensive spectroscopic analysis. Derrisrobustones A-C were obtained as scalemic mixtures and were resolved by chiral HPLC. The (1″R, 2″R) absolute configuration of (+)-derrisrobustone B was established by single-crystal X-ray crystallography using Cu Kα radiation. The absolute configurations of derrisrobustones A and C were determined by analysis of experimental and calculated ECD data. All compounds were evaluated for their α-glucosidase inhibitory activity. Of these, derrubone displayed the best α-glucosidase inhibitory activity with an IC value of 64.2 μM.

Address: The Research Unit of Natural Product Utilization, School of Science, Walailak University, Thasala, Nakhon Si Thammarat, 80160, Thailand.; Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Tasud, Muang, Chiang Rai, 57100, Thailand.; School of Science, Walailak University, Thasala, Nakhon Si Thammarat, 80160, Thailand.; Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, 40002, Thailand.; Functional Materials and Nanotechnology Center of Excellence, Walailak University, Thasala, Nakhon Si Thammarat, 80160, Thailand.; Institute of Nanomaterials Research and Innovation for Energy, Khon Kaen University, Khon Kaen, 40002, Thailand.; Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Tasud, Muang, Chiang Rai, 57100, Thailand; Medicinal Plant Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand. Electronic address: [email protected].

DOI: 10.1016/j.phytochem.2022.113168

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MeSH Terms: Derris, Isoflavones, Molecular Structure, Plant Extracts, alpha-Glucosidases