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

Liliana Ruiz-Vásquez; Matías Reina; M. López-Rodríguez; Cristina Giménez; Raimundo Cabrera; Pedro Cuadra; Víctor Fajardo; Azucena González-Coloma

doi:10.1016/j.phytochem.2015.06.019

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

Liliana Ruiz-Vásquez, Matías Reina, M. López-Rodríguez, Cristina Giménez, Raimundo Cabrera, Pedro Cuadra, Víctor Fajardo, Azucena González-Coloma

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

19 Citas (Scopus)

Resumen

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.

Idioma original	Inglés
Páginas (desde-hasta)	245-253
Número de páginas	9
Publicación	Phytochemistry
Volumen	117
DOI	https://doi.org/10.1016/j.phytochem.2015.06.019
Estado	Publicada - 22 jun. 2015
Publicado de forma externa	Sí

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10.1016/j.phytochem.2015.06.019

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@article{18e9b6761b7e4262ba43c8c3d350feab,

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

abstract = "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.",

keywords = "Asteraceae, Eremophilanolides, Flavonoids, Pyrrolizidine alkaloids, Senecio kingii, Shikimic acid derivatives, Structure-activity",

author = "Liliana Ruiz-V{\'a}squez and Mat{\'i}as Reina and M. L{\'o}pez-Rodr{\'i}guez and Cristina Gim{\'e}nez and Raimundo Cabrera and Pedro Cuadra and V{\'i}ctor Fajardo and Azucena Gonz{\'a}lez-Coloma",

note = "Publisher Copyright: {\textcopyright} 2015 Published by Elsevier Ltd.",

year = "2015",

month = jun,

day = "22",

doi = "10.1016/j.phytochem.2015.06.019",

language = "English",

volume = "117",

pages = "245--253",

journal = "Phytochemistry",

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T1 - Sesquiterpenes, flavonoids, shikimic acid derivatives and pyrrolizidine alkaloids from Senecio kingii Hook

AU - Ruiz-Vásquez, Liliana

AU - Reina, Matías

AU - López-Rodríguez, M.

AU - Giménez, Cristina

AU - Cabrera, Raimundo

AU - Cuadra, Pedro

AU - Fajardo, Víctor

AU - González-Coloma, Azucena

PY - 2015/6/22

Y1 - 2015/6/22

N2 - 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.

AB - 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.

KW - Asteraceae

KW - Eremophilanolides

KW - Flavonoids

KW - Pyrrolizidine alkaloids

KW - Senecio kingii

KW - Shikimic acid derivatives

KW - Structure-activity

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U2 - 10.1016/j.phytochem.2015.06.019

DO - 10.1016/j.phytochem.2015.06.019

M3 - Article

C2 - 26101146

AN - SCOPUS:84934926046

SN - 0031-9422

VL - 117

SP - 245

EP - 253

JO - Phytochemistry

JF - Phytochemistry

ER -

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

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