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

IF 2.1 4区医学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Steroids Pub Date : 2024-02-16 DOI:10.1016/j.steroids.2024.109390

Nivedita Bhardwaj , Priyamvada Gupta , Nancy Tripathi , Sanheeta Chakrabarty , Ashish Verma , Sanju Kumari , Vibhav Gautam , G. Ravikanth , Shreyans K. Jain

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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 structures and absolute 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.

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Dysoxylum malabaricum 树皮中新的环-A 改性环莰烷三萜类化合物：分离、结构阐释及其细胞毒性

Dysoxylum 属（旋花科）由大约 80 个物种组成，这些物种富含结构多样的三萜类化合物。本研究的重点是从 Dysoxylum malabaricum（印度主要的 Dysoxylum 物种之一）树皮中分离出新的三萜类化合物。对甲醇-二氯甲烷树皮提取物进行了 LCMS 分析，然后进行了硅胶柱层析和 HPLC 分析，以确定新的化合物。从树皮提取物中分离出了两种新的环 A 改性环安坦类三萜类化合物（1 和 2）。核磁共振、HRESIMS 数据和电子圆二色性计算等光谱方法阐明了分离出的化合物的结构和绝对构型。评估了这些化合物对乳腺癌细胞的细胞毒性潜力，结果显示它们具有显著的细胞毒性。化合物 1 对 MDA-MB-231 细胞的细胞毒性最高，能诱导细胞凋亡。此外，它还能抑制乳腺癌细胞对葡萄糖的摄取并增加一氧化氮的产生。

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来源期刊

Steroids 医学-内分泌学与代谢

CiteScore

5.10

自引率

3.70%

发文量

120

审稿时长

73 days

期刊介绍： STEROIDS is an international research journal devoted to studies on all chemical and biological aspects of steroidal moieties. The journal focuses on both experimental and theoretical studies on the biology, chemistry, biosynthesis, metabolism, molecular biology, physiology and pharmacology of steroids and other molecules that target or regulate steroid receptors. Manuscripts presenting clinical research related to steroids, steroid drug development, comparative endocrinology of steroid hormones, investigations on the mechanism of steroid action and steroid chemistry are all appropriate for submission for peer review. STEROIDS publishes both original research and timely reviews. For details concerning the preparation of manuscripts see Instructions to Authors, which is published in each issue of the journal.