Chemical constituents and biological activities of the aerial parts of Piper erecticaule C.DC. have been studied for the first time. Fractionation and purification of the extracts afforded aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4), piperolactam D (5), together with terpenoids of β-sitosterol, β-sitostenone, taraxerol, and lupeol. The structures of these compounds were obtained by analysis of their spectroscopic data, as well as the comparison with that of reported data. Acetylcholinesterase inhibitory activity revealed that compounds 1 and 3 showed strong AChE inhibitory effects with the percentage inhibition of 75.8% and 74.8%, respectively.Resumen: Se estudiaron por primera vez los constituyentes químicos y actividad biológica de las partes aéreas de Piper erecticaule C.DC. El fraccionamiento y la purificación de los extractos proporcionaron aristolactama AII (1), aristolactama BII (2), piperolactama A (3), piperolactama C (4), piperolactama D (5), junto con terpenoides de β-sitosterol, β-sitostenona, taraxerol, y el lupeol. Las estructuras de estos compuestos se obtuvieron mediante el análisis de sus datos espectroscópicos, así como mediante la comparación con datos ya informados. La actividad inhibidora de la acetilcolinesterasa reveló que los compuestos 1 y 3 mostraron un potente efecto inhibidor de la AChE con un porcentaje de inhibición del 75.8% y 74.8%, respectivamente. Este artículo puede ser citado como / This article must be cited as: WMNHW Salleh, N Abdullah, NA Hashim, HY Khong, S Khamis. 2019 Aporphine alkaloids from Piper erecticaule and acetylcholinesterase inhibitory activity. Bol Latinoam Caribe Plant Med Aromat 18 (5): 527 -532.
Background: Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In the present study, we attempted to isolate the phytochemicals from Piper caninum and Piper magnibaccum and evaluate their tyrosinase inhibitory activity. Methods: Phytochemical constituents of the extracts were investigated using various chromatographic and spectroscopic methods. The structures of the isolated phytochemicals were established by analysis of their spectroscopic data, as compared to that of reported data. Tyrosinase inhibitory activity was also tested on the extracts and selected compounds using mushroom tyrosinase as the enzyme. Results: Fractionation and purification of the extracts of Piper caninum and Piper magnibaccum afforded nine known compounds which were cepharanone A (1), cepharadione A (2), aristolactam AII (3), 5,7-dimethoxyflavone (4), 24-methylenecycloartan-3-one (5), β-sitosterol (6), piperumbellactam A (7), 24S-ethylcholesta-5,22,25-trien-3β-ol (8) and stigmast-3,6-dione (9). Ethyl acetate extracts from leaves of P. magnibaccum gave the highest inhibition value at 48.35%, while the tested compounds displayed weak tyrosinase activity compared to the positive control, kojic acid. Conclusion: These phytochemical results suggested that the extracts could assist as a potential source of bioactive compounds. Further research is needed in which the extract could possibly be exploited for pharmaceutical use.
The study was aimed to investigate the chemical components of stem and fruit volatile oils of Piper. maingayi Hk. with their antioxidant and antityrosinase activities. GC and GC-MS analysis of the essential oils obtained from the fresh stem and fruit of P. maingayi Hk. resulted in the identification of 34 and 18 components accounting for 83.6% and 78.7% of the total amount, respectively. Sesquiterpene hydrocarbons and oxygenated sesquiterpenes were the most highly represented classes as the former ranging from 64.7% to 70.7%, and the latter varying from 7.4% to 8.6%. The main constituents of the stem oil were: β-caryophyllene (26.2%), a-cedrene (8.4%), caryophyllene oxide (6.7%) and cis-calamenene (6.2%), while the fruit oil was dominated by δ-cadinene (22.6%), β-caryophyllene (18.8%), a-copaene (11.2%) and a-cadinol (7.1%). The stem and fruit of P. maingayi oils showed significant value for antioxidant and antityrosinase activities.
Chemical constituents and lipoxygenase inhibitory activity of the aerial part of Piper stylosum have been studied. Fractionation and purification of the extracts afforded five lignans, identified as yangambin (1), sesamin (2), syringaresinol (3), pinoresinol (4), and medioresinol (5), together with other constituents; 4-allyl resorcinol, β-sitosterol, β-sitostenone, taraxerol, vanilin, and vanilic acid. The structures of these compounds were established by analysis of their spectral data, as compared to that of reported compounds. The lipoxygenase inhibitory activity of the extracts and isolated lignans were also evaluated.
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