Publication: Styryllactones from Goniothalamus tamirensis
Issued Date
2020-03-01
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ISSN
00319422
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2-s2.0-85077324138
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Mahidol University
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SCOPUS
Bibliographic Citation
Phytochemistry. Vol.171, (2020)
Suggested Citation
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 Styryllactones from Goniothalamus tamirensis. Phytochemistry. Vol.171, (2020). doi:10.1016/j.phytochem.2019.112248 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/49508
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Title
Styryllactones from Goniothalamus tamirensis
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.