A Bis-benzopyrroloisoquinoline Alkaloid Incorporating a Cyclobutane Core and a Chlorophenanthroindolizidine Alkaloid with Cytotoxic Activity from Ficus fistulosa var. tengerensis.
Amjad Ayad Qatran Al-KhdhairawiPremanand KrishnanChun-Wai MaiFelicia Fei-Lei ChungChee-Onn LeongKien-Thai YongKam-Weng ChongYun-Yee LowToh-Seok KamKuan-Hon LimPublished in: Journal of natural products (2017)
Tengerensine (1), isolated as a racemate and constituted from a pair of bis-benzopyrroloisoquinoline enantiomers, and tengechlorenine (2), purified as a scalemic mixture and constituted from a pair of chlorinated phenanthroindolizidine enantiomers, were isolated from the leaves of Ficus fistulosa var. tengerensis, along with three other known alkaloids. The structures of 1 and 2 were determined by spectroscopic data interpretation and X-ray diffraction analysis. The enantiomers of 1 were separated by chiral-phase HPLC, and the absolute configurations of (+)-1 and (-)-1 were established via experimental and calculated ECD data. Compound 1 is notable in being a rare unsymmetrical cyclobutane adduct and is the first example of a dimeric benzopyrroloisoquinoline alkaloid, while compound 2 represents the first naturally occurring halogenated phenanthroindolizidine alkaloid. Compound (+)-1 displayed a selective in vitro cytotoxic effect against MDA-MB-468 cells (IC50 7.4 μM), while compound 2 showed pronounced in vitro cytotoxic activity against all three breast cancer cell lines tested (MDA-MB-468, MDA-MB-231, and MCF7; IC50 values of 0.038-0.91 μM).
Keyphrases
- breast cancer cells
- cell cycle arrest
- capillary electrophoresis
- ionic liquid
- cell death
- electronic health record
- high resolution
- ms ms
- mass spectrometry
- induced apoptosis
- big data
- pi k akt
- simultaneous determination
- molecular docking
- computed tomography
- data analysis
- young adults
- signaling pathway
- high performance liquid chromatography
- artificial intelligence
- tandem mass spectrometry
- liquid chromatography
- gas chromatography
- solid phase extraction
- anti inflammatory