Indole alkaloids from the leaves of Ravenia spectabilis engl. with activity against pancreatic cancer cell line. (June 2021)

• Record Type: Journal Article
• Authors: Tabassum, Fatema; Hasan, Choudhury Mahmood; Masud, Mohammad Mehedi; Jamshidi, Shirin; Rahman, Khondaker Miraz; Ahsan, Monira
• Is Part Of: Phytochemistry. Volume 186(2021)
• Publication Date: 2021-06
• Subjects: Ravenia spectabilis Engl. -- Rutaceae -- Indole alkaloid -- Pancreatic cancer -- Molecular modelling -- DNA interactive agents; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2021.112744
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Two previously undescribed indole alkaloids, 3-prenyl-5(3-keto-but-1-enyl) indole and 3-prenyl-indole-5-carbaldehyde, the structurally-related 3, 5-diprenyl indole and four known alkaloids were isolated from the leaves of Ravenia spectabilis Engl. Structures were elucidated based on nuclear magnetic resonance (1D and 2D NMR) spectroscopic and mass spectrometric analysis. The previously undescribed compounds isolated were subsequently screened against the HeLa (human cervical cancer), MIA PaCa-2 (human pancreatic adenocarcinoma) and A549 (lung cancer) cell lines. Among the isolated compounds, 3, 5-diprenyl indole was the most cytotoxic across all three cell lines (MIA PaCa-2 IC50 = 9.5 ± 2.2 μM). Molecular modelling studies suggested DNA intercalation as the mode of action of these compounds. Graphical abstract: Indole alkaloids from Ravenia spectabilis Engl. inhibits growth of pancreatic cancer cell line. Molecular modelling suggests DNA intercalation as the mechanism of action. Image 1 Highlights: Ravenia spectabilis Engl. is cultivated in gardens as an ornamental plant. Two previously undescribed and five previously described indole alkaloids were isolated. Previously undescribed compounds show notable activity against a pancreatic cancer cell line, MIA-PaCa-2. Molecular modelling suggests DNA intercalation as the mode of action.