(-)-Kunstleramide，一种来自 Beilschmiedia kunstleri gamble 树皮的新型抗氧化剂和细胞毒性二烯酰胺。

(-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of Beilschmiedia kunstleri gamble.

机构信息

Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia.

出版信息

Molecules. 2012 Apr 5;17(4):4197-208. doi: 10.3390/molecules17044197.

DOI:10.3390/molecules17044197

PMID:22481540

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268565/

Abstract

A new dienamide, (2E,4E)-7-(3',4'-dimethoxyphenyl)-N-ethyl-6-(R)-hydroxyhepta- 2,4-dienamide, named (-)-kunstleramide (1), were isolated from the bark of Beilschmiedia kunstleri Gamble together with one neolignan: (+)-kunstlerone (2) and seven known alkaloids: (+)-nornuciferine (3), (-)-isocaryachine (4), (+)-cassythicine (5), (+)-laurotetanine (6), (+)-boldine (7), noratherosperminine (8), (+)-N-demethylphyllocaryptine (9). Their structures were established from spectroscopic techniques, most notably 1D- and 2D-NMR, UV, IR, OR, circular dichroism (CD) spectra and LCMS-IT-TOF. (-)-Kunstleramide (1) exhibited very poor dose-dependent inhibition of DPPH activity, with an IC₅₀ value of 179.5 ± 4.4 μg/mL, but showed a moderate cytotoxic effect on MTT assays of A375, A549, HT-29, PC-3 and WRL-68 with EC₅₀ values of 64.65, 44.74, 55.94, 73.87 and 70.95 µg/mL, respectively.

摘要

从 Beilschmiedia kunstleri Gamble 的树皮中分离得到一种新的二烯酰胺化合物，（2E，4E）-7-（3'，4'-二甲氧基苯基）-N-乙基-6-（R）-羟基庚-2,4-二烯酰胺，命名为（-）kunstleramide（1），同时还分离得到一种新的木脂素：（+）-kunstlerone（2）和七种已知生物碱：（+）-nornuciferine（3），（-）-isocaryachine（4），（+）-cassythicine（5），（+）-laurotetanine（6），（+）-boldine（7），noratherosperminine（8），（+）-N-去甲石蒜碱（9）。其结构通过光谱技术，特别是 1D 和 2D-NMR、UV、IR、OR、圆二色性（CD）光谱和 LCMS-IT-TOF 确定。（-）kunstleramide（1）对 DPPH 活性表现出很差的剂量依赖性抑制作用，IC₅₀值为 179.5 ± 4.4 µg/mL，但对 A375、A549、HT-29、PC-3 和 WRL-68 的 MTT 测定表现出中等的细胞毒性作用，EC₅₀值分别为 64.65、44.74、55.94、73.87 和 70.95 µg/mL。