Chemical constituents and biological activities of Boesenbergia stenophylla, Polyalthia bullata and Prismatomeris glabra / Phoebe Sussana Primus

Phoebe Sussana , Primus (2024) Chemical constituents and biological activities of Boesenbergia stenophylla, Polyalthia bullata and Prismatomeris glabra / Phoebe Sussana Primus. PhD thesis, Universiti Malaya.

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Abstract

The chemical constituents from the rhizome of Boesenbergia stenophylla and the root of Polyalthia bullata and Prismatomeris glabra have been investigated. The extraction of the compounds was carried out using n-hexane, chloroform and ethanol followed by the isolation using chromatographic techniques such as column chromatography (CC), centrifugal thin layer chromatography (CTLC) and preparative thin layer chromatography (PTLC). Structural elucidations of the compounds were established through spectroscopic methods; 1D-NMR (1H,13C, DEPT-135), 2D-NMR (COSY, HSQC, HMBC), UV, IR and MS with comparison from the published data. 25 chemical compounds were successfully isolated from these three species. The B. stenophylla rhizome extract yielded three new compounds, stenophyllol A 458, stenophyllol B 459 and stenophyllol C 460 and five known compounds namely, (E)-7-(4-hydroxy-3-methoxyphenyl)-1-phenylhept-4-en-3-one 461, 5R-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-phenylheptan-3-one 462, 1,7-diphenylhept-4-en-3-one 463, 3,5,7-trihydroxyflavone 464, and oleic acid 465. Extraction and isolation on the root of Polyalthia bullata resulted in the isolation of eight chemical compounds, that is one new oxoaporhine alkaloid 5-methyl-liridine 466, six known alkaloids that is liriodenine 223, 11-methoxy-liriodenine 467, lysicamine 222, onychine 271, 5-hydroxy-6-methoxy-onychine 274, 8-methoxy-eupolauridine 237, and a methyl stearate 468. The investigation of the crude extract on the root of Prismatomeris glabra has resulted in the isolation of nine chemical compounds, which two of the compounds are new compounds with bisanthraquinone skeleton namely glabraquinone A 469 and glabraquinone B 470, six known anthraquinones, 1-hydroxy-2-methoxy-6-methyl-anthraquinone 471, 1,2-dimethoxy-7-methyl-anthraquinone 472, lucidin 379, nordamnacanthal 397, damnacanthal 398, 2-carboxaldehyde-3-hydroxy-anthraquinone396, and catechol diethyl ether 473. Compounds 459, 461, 463, 223, 469, 472, and 473were subjected to in vitro neuroblastoma cell viability assay using N2a cell line. Compounds 459, 461, and 223 displayed excellent in vitro anti-neuroblastoma activitywhich reduces the cell viability to 30%, 20%, 22%, respectively.

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