来自三瓣暗罗（Pseuduvaria trimera (Craib)）叶和嫩枝的细胞毒性阿朴啡生物碱。

Cytotoxic aporphine alkaloids from leaves and twigs of Pseuduvaria trimera (Craib).

作者信息

Sesang Wuttikrai, Punyanitya Sittiporn, Pitchuanchom Siripit, Udomputtimekakul Phansuang, Nuntasaen Narong, Banjerdpongchai Ratana, Wudtiwai Benjawan, Pompimon Wilart

机构信息

Laboratory of Natural Products, Center for Innovation in Chemistry, Faculty of Science, Lampang Rajabhat University, Lampang 52100, Thailand.

Science and Technology Research Institute, Chiang Mai University, Chiang Mai 53000, Thailand.

出版信息

Molecules. 2014 Jun 25;19(7):8762-72. doi: 10.3390/molecules19078762.

DOI:10.3390/molecules19078762

PMID:24968332

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270962/

Abstract

From ethyl acetate-methanol extracts of leaves and twigs of Pseuduvaria trimera a new aporphine alkaloid; 8-hydroxy-1,4,5-trimethoxy-7-oxoaporphine or 8-hydroxyartabonatine C (1) was isolated, together with the known 1,2,3-trimethoxy-4,5-dioxo-6a,7-dehydroaporphine (ouregidione, 2). Their structures were elucidated by a combination of spectral methods; mainly 2D NMR; IR and MS. Compounds 1 and 2 exhibited cytotoxic activity with IC50 values of 26.36±5.18 μM and 12.88±2.49 μM, respectively, for human hepatocellular carcinoma HepG2 cells, and 64.75±4.45 and 67.06±3.5 μM, respectively, for human breast cancer MDA-MB231 cells. Both compounds displayed anti-cancer activity but less than that of doxorubicin; a conventional chemotherapeutic drug, the IC50 levels of which were 2.21±1.72 and 1.83±0.09 μM for HepG2 and MDA-MB231 cells, respectively.

摘要

从三叶暗罗叶和嫩枝的乙酸乙酯 - 甲醇提取物中分离出一种新的阿朴啡生物碱；8 - 羟基 - 1,4,5 - 三甲氧基 - 7 - 氧代阿朴啡或8 - 羟基阿他波宁C（1），以及已知的1,2,3 - 三甲氧基 - 4,5 - 二氧代 - 6a,7 - 脱氢阿朴啡（欧瑞吉酮，2）。通过多种光谱方法相结合阐明了它们的结构；主要是二维核磁共振、红外光谱和质谱。化合物1和2对人肝癌HepG2细胞表现出细胞毒性活性，IC50值分别为26.36±5.18 μM和12.88±2.49 μM，对人乳腺癌MDA - MB231细胞的IC50值分别为64.75±4.45和67.06±3.5 μM。这两种化合物均显示出抗癌活性，但低于阿霉素；一种传统化疗药物，其对HepG2和MDA - MB231细胞的IC50水平分别为2.21±1.72和1.83±0.09 μM。