Dimeric aporphine alkaloids from the twigs of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner

Passakorn Teerapongpisan; Virayu Suthiphasilp; Piyaporn Phukhatmuen; Narawadee Rujanapun; Boonyanoot Chaiyosang; Sarawut Tontapha; Tharakorn Maneerat; Brian O Patrick; Thidarat Duangyod; Rawiwan Charoensup; Raymond J Andersen; Surat Laphookhieo

doi:10.1016/j.phytochem.2023.113586

Dimeric aporphine alkaloids from the twigs of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner

Phytochemistry. 2023 Mar:207:113586. doi: 10.1016/j.phytochem.2023.113586. Epub 2023 Jan 9.

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 Medicinal Plant Innovation Center of Mae Fah, Luang University, Chiang Rai, 57100, Thailand.
⁴ 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.
⁵ Institute of Nanomaterials Research and Innovation for Energy, Khon Kaen University, Khon Kaen, 40002, Thailand.
⁶ 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.
⁷ Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
⁸ 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.
⁹ Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada; Department of Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada. Electronic address: raymond.andersen@ubc.ca.
¹⁰ 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: 36632950
DOI: 10.1016/j.phytochem.2023.113586

Abstract

A phytochemical investigation of the twig extract of Trivalvaria costata (Hook.f. & Thomson) I.M.Turner has identified ten undescribed dimeric aporphine alkaloids, trivalcostatines A-J, one undescribed isoquinoline alkaloid, trivalcostaisoquinoline, and four known aporphine alkaloids. Their structures were elucidated by detailed analysis of NMR and HRESITOFMS data. Three of the dimeric aporphine structures were confirmed by single crystal X-ray diffraction analysis. All of the dimeric aporphine alkaloids were isolated as mixtures of atropisomers. Several of them were resolved by chiral-phase HPLC and the absolute configurations of the pure atropisomers were assigned by calculated and experimental ECD analysis. Bidebilines A and B, heteropsine, and urabaine showed α-glucosidase inhibitory activities with IC₅₀ values in the range of 4.1-11 μM.

Keywords: Alkaloids; Annonaceae; Dimeric aporphine alkaloids; Trivalvaria costata; α-Glucosidase inhibitory activity.

MeSH terms

Alkaloids* / chemistry
Alkaloids* / pharmacology
Annonaceae* / chemistry
Aporphines* / chemistry
Aporphines* / pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure

Substances

Aporphines
Alkaloids