Tabassum Fatema, Hasan Choudhury Mahmood, Masud Mohammad Mehedi, Jamshidi Shirin, Rahman Khondaker Miraz, Ahsan Monira
Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka, 1000, Bangladesh; Department of Pharmacy, Northern University Bangladesh, Dhaka, 1205, Bangladesh.
Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka, 1000, Bangladesh.
Phytochemistry. 2021 Jun;186:112744. doi: 10.1016/j.phytochem.2021.112744. Epub 2021 Mar 26.
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 IC = 9.5 ± 2.2 μM). Molecular modelling studies suggested DNA intercalation as the mode of action of these compounds.
从美丽拉文木（Ravenia spectabilis Engl.）的叶子中分离出两种此前未被描述的吲哚生物碱，即3-异戊烯基-5(3-氧代-丁-1-烯基)吲哚和3-异戊烯基吲哚-5-甲醛，以及结构相关的3,5-二异戊烯基吲哚和四种已知生物碱。通过核磁共振（一维和二维核磁共振）光谱和质谱分析阐明了其结构。随后，对分离出的此前未被描述的化合物针对人宫颈癌HeLa细胞系、人胰腺腺癌MIA PaCa-2细胞系和肺癌A549细胞系进行了筛选。在分离出的化合物中，3,5-二异戊烯基吲哚对所有这三种细胞系的细胞毒性最大（MIA PaCa-2细胞系的半数抑制浓度IC = 9.5 ± 2.2 μM）。分子模拟研究表明，这些化合物的作用方式为DNA嵌入。
