Rotenoids and isoflavones from the leaf and pod extracts of Millettia brandisiana Kurz

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

doi:10.1016/j.phytochem.2022.113440

Rotenoids and isoflavones from the leaf and pod extracts of Millettia brandisiana Kurz

Phytochemistry. 2022 Dec:204:113440. doi: 10.1016/j.phytochem.2022.113440. Epub 2022 Sep 18.

Affiliations

¹ Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
² Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; 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 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.
⁸ 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.
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: 36130672
DOI: 10.1016/j.phytochem.2022.113440

Abstract

Phytochemical investigations of the leaf and pod extracts of Millettia brandisiana Kurz led to the isolation and identification of four previously undescribed rotenoids, (-)-(6aS,12aS)-millettiabrandisins A-C and (-)-(6aS,12aS)-6-deoxyclitoriacetal, two previously undescribed isoflavones, millettiabrandisins D and E, and 20 known compounds. The structures of previously undescribed compounds were determined on the basis of NMR and MS data. The absolute configurations of (-)-(6aS,12aS)-millettiabrandisins A-C were determined from the comparison of their experimental and calculated ECD spectra. (-)-(6aR,12aR)-12a-Hydroxy-α-toxicarol was also confirmed by X-ray crystallographic data. Some isolated compounds were evaluated for their cytotoxicity against three cancer cell lines, including lung cancer (A549), colorectal cancer (SW480), and leukemic cells (K562). Of these, α-toxicarol displayed the best cytotoxicity against lung cancer (A549) and leukemic cells (K562) with the IC₅₀ values of 104.4 and 67.5 μM, respectively. 6″,6″-Dimethylchromene-[2″,3″:7,8]-flavone showed the highest cytotoxicity against colorectal cancer (SW480) with an IC₅₀ value of 97.2 μM.

Keywords: Cytotoxicity; Isoflavones; Leguminosae; Millettia brandisiana; Rotenoids.