Novel N-oxide derivatives of benzyltetrahydroisoquinoline alkaloid from the tubers of Stephania viridiflavens H.S. Lo et M. Yang
Novel N-oxide derivatives of benzyltetrahydroisoquinoline alkaloid from the tubers of Stephania viridiflavens H.S. Lo et M. Yang
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DOI：
10.1016/j.phytol.2011.11.001
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发表时间：
2012-03
影响因子：
1.7
通讯作者：
Mao-sheng Zhang;Fumei Yang;Dao-ping Wang;Jian-xin Zhang;Qian-yun Sun;Guang-yi Liang;W. Pan
中科院分区：
文献类型：
--
作者：
Mao-sheng Zhang;Fumei Yang;Dao-ping Wang;Jian-xin Zhang;Qian-yun Sun;Guang-yi Liang;W. Pan
药用植物绿黄千金藤的植物化学研究。Lo et M. Yang领导分离出两种新的天然苄基四氢异喹啉生物碱，（+）-1S，2 R-劳丹尼定-Nβ-氧化物2和（+）-1S，2S-劳丹尼定-Nα-氧化物3，沿着还有四种已知的苄基四氢异喹啉生物碱：（+）-劳丹尼定1、（+）-牛心果碱4、（+）-1S，2 R-牛心果碱-Nβ-氧化物5和（+）-1S，2S-牛心果碱-Nα-氧化物6。这些化合物的结构和立体化学的基础上确定的光谱方法，也证实了部分合成。为了检测推定的乙酰胆碱酯酶（AChE）抑制或细胞毒性活性，进行了各种生物测定，N-氧化物衍生物（5和6）表现出比相应的游离碱更强的细胞毒性。
An investigation on the phytochemistry of the medicinal plant Stephania viridiflavens H.S. Lo et M. Yang led to isolate two new naturally occurring benzyltetrahydroisoquinoline alkaloids, (+)-1S, 2R-laudanidine-Nβ-oxide 2 and (+)-1S, 2S-laudanidine-Nα-oxide 3, along with four known benzyltetrahydroisoquinoline alkaloids: (+)-laudanidine 1, (+)-reticuline 4, (+)-1S, 2R-reticuline-Nβ-oxide 5 and (+)-1S, 2S-reticuline-Nα-oxide 6. The structure and the stereochemistry of these compounds were determined on the basis of spectroscopic methods and also confirmed by partial synthesis. To examine putative acetycholinesterase (AChE) inhibitory or cytotoxic activities, various bioassays were performed, the N-oxide derivatives (5 and 6) demonstrated more potent cytotoxicity than the corresponding free base.