Sesquiterpenes, flavonoids, shikimic acid derivatives and pyrrolizidine alkaloids from Senecio kingii Hook

Twenty-four compounds including eleven eremophilanolides (1–11), one eremophilane (13), five shikimic acid derivatives (14–18), six flavonoids (19–24), and the macrocyclic unsaturated pyrrolizidine alkaloid integerrimine (25) were isolated from Senecio kingii, an endemic species from the Magallanes Region (Chile). Compounds 3, 5, 6, 8–11 and 13–18 have not been previously reported as natural products. Their molecular structures were determined by NMR spectroscopic analysis and comparison with published NMR data. An X-ray-analysis of compound 3 has been performed. Their insecticidal and antifungal activities were tested, being compound 3 the strongest insect antifeedant. Compounds 6, 9 and 18 were moderate antifungals.

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Bibliographic Details
Main Authors: Ruiz-Vasquez, Liliana, Reina, Matías, López-Rodríguez, Matías, Giménez, Cristina, Cabrera, Raimundo, Cuadra, Pedro, Fajardo, Víctor, González-Coloma, Azucena
Other Authors: Ministerio de Economía y Competitividad (España)
Format: artículo biblioteca
Published: Elsevier 2015-09
Subjects:Pyrrolizidine Alkaloids, Senecio Kingii, Structure–activity, Asteraceae, Flavonoids, Shikimic Acid Derivatives, Eremophilanolides,
Online Access:http://hdl.handle.net/10261/181115
http://dx.doi.org/10.13039/501100008792
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100003329
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Summary:Twenty-four compounds including eleven eremophilanolides (1–11), one eremophilane (13), five shikimic acid derivatives (14–18), six flavonoids (19–24), and the macrocyclic unsaturated pyrrolizidine alkaloid integerrimine (25) were isolated from Senecio kingii, an endemic species from the Magallanes Region (Chile). Compounds 3, 5, 6, 8–11 and 13–18 have not been previously reported as natural products. Their molecular structures were determined by NMR spectroscopic analysis and comparison with published NMR data. An X-ray-analysis of compound 3 has been performed. Their insecticidal and antifungal activities were tested, being compound 3 the strongest insect antifeedant. Compounds 6, 9 and 18 were moderate antifungals.