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Title: Styryllactones from Goniothalamus tamirensis
Authors: Pornphimol Meesakul
Wuttichai Jaidee
Christopher Richardson
Raymond J. Andersen
Brian O. Patrick
Anthony C. Willis
Chatchai Muanprasat
Jin Wang
Xiaoguang Lei
Sarinya Hadsadee
Siriporn Jungsuttiwong
Stephen G. Pyne
Surat Laphookhieo
College of Chemistry and Molecular Engineering, Peking University
Ubon Rajathanee University
Mae Fah Luang University
Peking University
Mahidol University
University of Wollongong
The University of British Columbia
Australian National University
Keywords: Agricultural and Biological Sciences;Biochemistry, Genetics and Molecular Biology
Issue Date: 1-Mar-2020
Citation: Phytochemistry. Vol.171, (2020)
Abstract: © 2019 Elsevier Ltd The phytochemical investigation of the twig and leaf extracts of Goniothalamus tamirensis led to the isolation and identification of 15 compounds including three rare previously undescribed styryllactones, goniotamirenones A-C, together with 12 known compounds. (Z)-6-Styryl-5,6-dihydro-2-pyranone and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one are reported here for the first time as previously undescribed natural products. Their structures were elucidated by spectroscopic methods. Goniotamirenone A was synthesized via a [2 + 2] cycloaddition reaction of 6-styrrylpyran-2-one in quantitative yield. The absolute configurations of goniotamirenones B and C were identified from experimental and calculated ECD data, while the absolute configurations of (−)–5-acetoxygoniothalamin, (−)-isoaltholactone, parvistone E, and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one were identified by single-crystal X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with relevant compounds reported in the literature. (−)–5-Acetoxygoniothalamin exhibited potent cytotoxicity against the colon cancer cell line (HCT116) with an IC50 value of 8.6 μM which was better than the standard control (doxorubicin, IC50 = 9.7 μM), while (Z)-6-styryl-5,6-dihydro-2-pyranone was less active with an IC50 value of 22.1 μM.
ISSN: 00319422
Appears in Collections:Scopus 2020

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