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Bioactive Asarone-Derived Phenylpropanoids from the Rhizome of Acorus tatarinowii Schott
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-08 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00457 En Gao 1 , Zheng-Qun Zhou 1 , Jian Zou 1 , Yang Yu 1 , Xiao-Lin Feng 1 , Guo-Dong Chen 1 , Rong-Rong He 1 , Xin-Sheng Yao 1 , Hao Gao 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2017-11-08 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00457 En Gao 1 , Zheng-Qun Zhou 1 , Jian Zou 1 , Yang Yu 1 , Xiao-Lin Feng 1 , Guo-Dong Chen 1 , Rong-Rong He 1 , Xin-Sheng Yao 1 , Hao Gao 1
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Eight new (1a/1b, 2a, 3a, 4a/4b, and 5a/5b) and seven known (2b, 3b, and 6–10) asarone-derived phenylpropanoids, a known asarone-derived lignan (12), and four known lignan analogues (11 and 13–15) were isolated from the rhizome of Acorus tatarinowii Schott. The structures were elucidated via comprehensive spectroscopic analyses, modified Mosher’s method, and quantum chemical calculations. Compounds 1–8 were present as enantiomers, and 1–5 were successfully resolved via chiral-phase HPLC. Compounds 1a/1b were the first cases of asarone-derived phenylpropanoids with an isopropyl C-3 side-chain tethered to a benzene core from nature. Hypoglycemic, antioxidant, and AChE inhibitory activities of 1–15 were assessed by the α-glucosidase inhibitory, ORAC, DPPH radical scavenging, and AChE inhibitory assays, respectively. All compounds except 3a showed α-glucosidase inhibitory activity. Compound 3b has the highest α-glucosidase inhibitory effect with an IC50 of 80.6 μM (positive drug acarbose IC50 of 442.4 μM). In the antioxidant assays, compounds 13–15 exhibited ORAC and DPPH radical scavenging activities. The results of the AChE inhibitory assay indicated that all compounds exhibited weak AChE inhibitory activities.
中文翻译：
生物活性的Asarus tatarinowii Schott的根状茎的Asarone衍生的苯丙烷类化合物。
八个新（1A / 1B，2A，3A，4A / 4B和5A /图5B）和七个已知的（图2b，图3b，和6 - 10）细辛醚衍生苯丙，已知细辛醚衍生的木酚素（12），和四个已知的木酚素类似物（11和13 - 15）获自的根茎中分离石菖蒲肖特。通过全面的光谱分析，改进的Mosher方法和量子化学计算来阐明结构。化合物1 – 8作为对映异构体存在，而1 – 5通过手性液相色谱法成功分离。化合物1a / 1b是最早从Asarone衍生的苯丙烷类化合物，其异丙基C-3侧链从自然界拴在苯核上。分别通过α-葡萄糖苷酶抑制，ORAC，DPPH自由基清除和AChE抑制试验评估了1 – 15的降血糖，抗氧化剂和AChE抑制活性。除3a外的所有化合物均显示出α-葡萄糖苷酶抑制活性。化合物3b具有最高的α-葡萄糖苷酶抑制作用，IC 5080.6μM（阳性药物阿卡波糖IC 50为442.4μM）。在抗氧化剂测定中，化合物13 - 15个表现出ORAC和DPPH自由基清除活性。AChE抑制试验的结果表明，所有化合物均显示出弱的AChE抑制活性。
更新日期：2017-11-08
中文翻译：
生物活性的Asarus tatarinowii Schott的根状茎的Asarone衍生的苯丙烷类化合物。
八个新（1A / 1B，2A，3A，4A / 4B和5A /图5B）和七个已知的（图2b，图3b，和6 - 10）细辛醚衍生苯丙，已知细辛醚衍生的木酚素（12），和四个已知的木酚素类似物（11和13 - 15）获自的根茎中分离石菖蒲肖特。通过全面的光谱分析，改进的Mosher方法和量子化学计算来阐明结构。化合物1 – 8作为对映异构体存在，而1 – 5通过手性液相色谱法成功分离。化合物1a / 1b是最早从Asarone衍生的苯丙烷类化合物，其异丙基C-3侧链从自然界拴在苯核上。分别通过α-葡萄糖苷酶抑制，ORAC，DPPH自由基清除和AChE抑制试验评估了1 – 15的降血糖，抗氧化剂和AChE抑制活性。除3a外的所有化合物均显示出α-葡萄糖苷酶抑制活性。化合物3b具有最高的α-葡萄糖苷酶抑制作用，IC 5080.6μM（阳性药物阿卡波糖IC 50为442.4μM）。在抗氧化剂测定中，化合物13 - 15个表现出ORAC和DPPH自由基清除活性。AChE抑制试验的结果表明，所有化合物均显示出弱的AChE抑制活性。
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