Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Virayu Suthiphasilp; Tharakorn Maneerat; Thidarat Duangyod; Rawiwan Charoensup; Raymond J Andersen; Stephen G Pyne; Surat Laphookhieo

doi:10.1016/j.heliyon.2020.e05791

Polyoxygenated seco-cyclohexenes derivatives from flower and leaf extracts of Desmos cochinchinensis and their α-glucosidase inhibitory activity

Heliyon. 2020 Dec 23;6(12):e05791. doi: 10.1016/j.heliyon.2020.e05791. eCollection 2020 Dec.

Authors

Virayu Suthiphasilp¹, Tharakorn Maneerat^{1

2}, Thidarat Duangyod^{2

3}, Rawiwan Charoensup^{2

3}, Raymond J Andersen⁴, Stephen G Pyne⁵, Surat Laphookhieo^{1

2}

Affiliations

¹ Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
² Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand.
³ School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
⁴ Department of Chemistry and Department of Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036, Main Mall, Vancouver, BC, V6T 1Z1, Canada.
⁵ School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales, 2522, Australia.

Abstract

Phytochemical investigations from the flower and leaf extracts of D. cochinchinensis resulted in the isolation and structural elucidation of five new polyoxygenated seco-cyclohexene derivatives, desmoscochinchinenes A-E (1-5), together with 11 known compounds (6-16). The structures on the new compounds were elucidated from their spectroscopic data, including UV, IR, NMR, and HRESITOFMS. Some of the isolated compounds were evaluated for their α-glucosidase inhibitory activities. Chrysin (9), pinocembrin 7-O-benzoate (12), and (-)-(5R)-desmoscochinoxepinone B (16) inhibited α-glucosidase better than the standard control (acarbose, IC₅₀ = 83.5 μM) with IC₅₀ values of 5.7, 33.8, 53.3 μM, respectively.

Keywords: Annonaceae; Desmos cochinchinensis; Seco-cyclohexenes; α-Glucosidase inhibitory activity.