Styryllactones from Goniothalamus tamirensis,Phytochemistry

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Styryllactones from Goniothalamus tamirensis
Phytochemistry ( IF 3.2 ) Pub Date : 2020-03-01 , DOI: 10.1016/j.phytochem.2019.112248
Pornphimol Meesakul ₁ , Wuttichai Jaidee ₂ , Christopher Richardson ₃ , Raymond J Andersen ₄ , Brian O Patrick ₄ , Anthony C Willis ₅ , Chatchai Muanprasat ₆ , Jin Wang ₇ , Xiaoguang Lei ₈ , Sarinya Hadsadee ₉ , Siriporn Jungsuttiwong ₉ , Stephen G Pyne ₃ , Surat Laphookhieo ₂

Affiliation

Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand.
School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
Research School of Chemistry, The Australian National University, Canberra, ACT, 2601, Australia.
Division of Preclinical Sciences, Chakri Naruebodindra Medical Institute, Faculty of Medicine Ramathibodi Hospital, Mahidol University, Bangpli, Samutprakarn, 10540, Thailand; Excellent Center of Drug Discovery, Faculty of Science, Mahidol University, Rajathevi, Bangkok, 10400, Thailand.
College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China; Peking-Tsinghua Center for Life Science, Peking University, Beijing, 100871, China.
Center for Organic Electronic and Alternative Energy, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, 34190, Thailand.

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.

中文翻译：

来自 Goniothalamus tamirensis 的苯乙烯内酯

对 Goniothalamus tamirensis 的树枝和叶子提取物的植物化学研究导致了 15 种化合物的分离和鉴定，包括三种罕见的以前未描述的苯乙烯内酯，goniotamirenones AC，以及 12 种已知化合物。(Z)-6-Styryl-5,6-dihydro-2-pyranone 和 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one 在这里首次报道为以前未描述的天然产品。它们的结构是通过光谱方法阐明的。Goniotamirenone A 通过 6-styrrylpyran-2-one 的 [2 + 2] 环加成反应以定量收率合成。从实验和计算的 ECD 数据中确定了 goniotamirenones B 和 C 的绝对构型，而 (-)-5-acetoxygoniothalamin、(-)-isoaltholactone、parvistone E、和 5-(1-羟基-3-苯基-烯丙基)-二氢-呋喃-2-one 通过使用 Cu Kα 辐射的单晶 X 射线衍射分析进行鉴定。其他相关化合物的绝对构型是通过将它们的 ECD 光谱与文献中报道的相关化合物进行比较来确定的。(-)-5-Acetoxygoniothalamin 对结肠癌细胞系 (HCT116) 表现出有效的细胞毒性，IC50 值为 8.6 μM，优于标准对照（多柔比星，IC50 = 9.7 μM），而 (Z)-6-苯乙烯基-5,6-dihydro-2-pyranone 的活性较低，IC50 值为 22.1 μM。

更新日期：2020-03-01

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