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Evaluation of Diarylheptanoid–Terpene Adduct Enantiomers from Alpinia officinarum for Neuroprotective Activities
Journal of Natural Products ( IF 3.3 ) Pub Date : 2018-01-11 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00803
Hui Liu 1, 2, 3 , Zhen-Long Wu 1, 2, 3 , Xiao-Jun Huang 1, 2, 3 , Yinghui Peng 2, 3 , Xiaojie Huang 2, 3 , Lei Shi 2, 3 , Ying Wang 1, 2, 3 , Wen-Cai Ye 1, 2, 3
Affiliation  

Two pairs of new diarylheptanoid–monoterpene adduct enantiomers, (±)-alpininoids A and B [(±)-1 and (±)-2], as well as three pairs of new diarylheptanoid–sesquiterpene adduct enantiomers, (±)-alpininoids C–E [(±)-3–(±)-5], together with four known diarylheptanoids (69) were isolated from the rhizomes of Alpinia officinarum. Their structures with absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses and computational calculation methods. The skeletons of these cyclohexene-containing hybrid natural products were hypothesized to be generated via a crucial Diels–Alder cycloaddition between the diarylheptanoids (7 and 8) and terpenes, of which 1 represents a new carbon skeleton. All isolated compounds were evaluated for their neuroprotective effects against MPP+ (1-methyl-4-phenylpyridinium)-induced cortical neuron injury. At a concentration of 16 μM, (+)-1 significantly increased cell viability when compared with MPP+ treatment alone.

中文翻译:

从二芳基庚萜烯加合物对映体的评价高良姜用于神经保护活动

两对新的二芳基庚烷-单萜加合物对映体,(±)-Apininoids A和B [(±)-1和(±)-2 ],以及三对新的二芳基庚烷-倍半萜烯-倍半萜烯加合物对映体,(±)-类萜素C-E [(±) - 3 - (±) - 5 ],与四种已知二芳基庚(一起6 - 9)从的根茎中分离高良姜。在全面的光谱分析和计算计算方法的基础上,阐明了它们具有绝对构型的结构。假设这些含环己烯的杂化天然产物的骨架是通过二芳基庚烷之间的关键Diels-Alder环加成反应生成的(78)和萜烯,其中1代表新的碳骨架。评估所有分离的化合物对MPP +(1-甲基-4-苯基吡啶)诱导的皮质神经元损伤的神经保护作用。与单独的MPP +治疗相比,浓度为16μM时,(+)- 1显着提高了细胞活力。
更新日期:2018-01-11
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