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

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

Journal: Steroids 2024;205():109390

PMID: 38367679

Full Text on Elsevier Science View on PubMed

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.

Address: 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.; Department of Biomedical Engineering, Indian Institute of Technology (Banaras Hindu University), Varanasi 221005, Uttar Pradesh, India.; S.M. Sehgal Foundation Center for Biodiversity and Conservation, Ashoka Trust for Research in Ecology and the Environment, Bangalore 560064, Karnataka, India.; Department of Pharmaceutical Engineering and Technology, Indian Institute of Technology (Banaras Hindu University), Varanasi 221005, Uttar Pradesh, India. Electronic address: [email protected].

DOI: 10.1016/j.steroids.2024.109390

Link outs

Free resources

Medical:

https://medlineplus.gov/breastcancer.html

Miscellaneous:

https://assays.cancer.gov/CPTAC-1474

Subscription / membership required

Full Text Sources:

MeSH Terms: Female, Humans, Antineoplastic Agents, Phytogenic, Breast Neoplasms, Meliaceae, Molecular Structure, Plant Bark, Plant Extracts, Triterpenes, Methanol, Hydrocarbons, Chlorinated