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新的环阿屯烷三萜类化合物来自倒卵叶花椒树皮:分离、结构阐明及其细胞毒性。

New ring-A modified cycloartane triterpenoids from Dysoxylum malabaricum bark: Isolation, structure elucidation and their cytotoxicity.

机构信息

Department of Pharmaceutical Engineering and Technology, Indian Institute of Technology (Banaras Hindu University), Varanasi 221005, Uttar Pradesh, India.

Centre of Experimental Medicine and Surgery, Institute of Medical Sciences, Banaras Hindu University, Varanasi 221005, Uttar Pradesh, India.

出版信息

Steroids. 2024 May;205:109390. doi: 10.1016/j.steroids.2024.109390. Epub 2024 Feb 16.

DOI:10.1016/j.steroids.2024.109390
PMID:38367679
Abstract

The Genus Dysoxylum (Meliaceae) consists of approximately 80 species that are abundant in structurally diverse triterpenoids. The present study focused on isolating new triterpenoids from the bark of Dysoxylum malabaricum, one of the predominant species of Dysoxylum present in India. The methanol-dichloromethane bark extract was subjected to LCMS profiling followed by silica gel column chromatography and HPLC analysis to target new compounds. Two new ring A-modified cycloartane-type triterpenoids (1 and 2) were isolated from the bark extract. Spectroscopic methods like NMR, HRESIMS data, and electronic circular dichroism calculations elucidated the structuresandabsolute configurations of the isolated compounds. These compounds were evaluated for their cytotoxic potential against breast cancer cells and displayed notable cytotoxicity. Compound 1 exhibited the highest cytotoxicity against the MDA-MB-231 cells and induced apoptotic cell death. Also, it was able to inhibit glucose uptake and increase nitric oxide production in breast cancer cells.

摘要

该属 Dysoxylum(芸香科)由约 80 种组成,富含结构多样的三萜类化合物。本研究集中于从 Dysoxylum malabaricum 的树皮中分离新的三萜类化合物,Dysoxylum malabaricum 是印度主要的 Dysoxylum 物种之一。甲醇-二氯甲烷树皮提取物进行 LCMS 分析,然后进行硅胶柱层析和 HPLC 分析,以靶向新化合物。从树皮提取物中分离出两种新的 A 环修饰的环阿屯烷型三萜(1 和 2)。通过 NMR、HRESIMS 数据和电子圆二色性计算等光谱方法阐明了分离化合物的结构和绝对构型。这些化合物的细胞毒性进行了评估,以评估其对乳腺癌细胞的潜在作用,并显示出明显的细胞毒性。化合物 1 对 MDA-MB-231 细胞的细胞毒性最高,诱导细胞凋亡。此外,它还能够抑制乳腺癌细胞中的葡萄糖摄取并增加一氧化氮的产生。

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