Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities
Virayu Suthiphasilp,
Moses Egoh Betangah,
Passakorn Teerapongpisan,
Narawadee Rujanapun,
Boonyanoot Chaiyosang,
Sarawut Tontapha,
Pakit Kumboonma,
Brian O. Patrick,
Raymond J. Andersen,
Rawiwan Charoensup,
Thidarat Duangyod,
Phunrawie Promnart,
Tharakorn Maneerat,
Surat Laphookhieo
Affiliations
Virayu Suthiphasilp
Department of Industrial Technology and Innovation Management, Faculty of Science and Technology, Pathumwan Institute of Technology, Bangkok, 10330, Thailand
Moses Egoh Betangah
Center of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand
Passakorn Teerapongpisan
Futuristic Science Research Center, School of Science, Walailak University, Nakhon Si Thammarat, 80160, Thailand; Center of Excellence for Advanced Research in Future-Oriented Sciences (CEAR-FOS), Walailak University, Nakhon Si Thammarat, 80160, Thailand
Narawadee Rujanapun
Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand
Boonyanoot Chaiyosang
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
Sarawut Tontapha
Institute of Nanomaterials Research and Innovation for Energy, Khon Kaen University, Khon Kaen, 40002, Thailand
Pakit Kumboonma
Department of Applied Chemistry, Faculty of Science and Liberal Arts, Rajamangala University of Technology Isan, Nakhon Ratchasima, 30000, Thailand
Brian O. Patrick
Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada
Raymond J. Andersen
Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada
Rawiwan Charoensup
Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, Thailand
Thidarat Duangyod
Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Integrative Medicine, Mae Fah Luang University, Chiang Rai, 57100, Thailand
Phunrawie Promnart
School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand
Tharakorn Maneerat
Center of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand
Surat Laphookhieo
Center of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai, 57100, Thailand; Corresponding author. Center of Chemical Innovation for Sustainability (CIS), and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
Phytochemical investigation of the leaf extract of Uvaria grandiflora Roxb. ex Hornem led to the isolation and identification of two new highly oxygenated cyclohexenes, uvariagrandols A (1) and B (2), together with seven known compounds (3–9). Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. The (1S,2S,3R,6S) absolute configuration of uvariagrandols A and B was established by the comparison of the experimental and calculated electronic circular dichroism (ECD). (+)-Grandifloracin (9) displayed cytotoxicity against SW480 and K562 cell lines with IC50 values of 154.9 and 60.9 μM, respectively. 6-Methoxyzeylenol (5) had α-glucosidase inhibitory activity with the IC50 value of 34.1 μM.
