Complete 1H NMR assignments of pyrrolizidine alkaloids and a new eudesmanoid from Senecio polypodioides

Claudia Villanueva-Cañongo; Nury Pérez-Hernández; Beatriz Hernández-Carlos; Ernestina Cedillo-Portugal; Pedro Joseph-Nathan; Eleuterio Burgueño-Tapia

doi:10.1002/mrc.4054

Complete ¹H NMR assignments of pyrrolizidine alkaloids and a new eudesmanoid from Senecio polypodioides

Claudia Villanueva-Cañongo, Nury Pérez-Hernández, Beatriz Hernández-Carlos, Ernestina Cedillo-Portugal, Pedro Joseph-Nathan, Eleuterio Burgueño-Tapia

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

Chemical investigation of the aerial parts of Senecio polypodioides lead to the isolation of the new eudesmanoid 1β-angeloyloxyeudesm-7-ene-4β, 9α-diol (1) and the known dirhamnosyl flavonoid lespidin (3), while from roots, the known 7β-angeloyloxy-1-methylene-8α-pyrrolizidine (5) and sarracine N-oxide (6), as well as the new neosarracine N-oxide (8), were obtained. The structure of 1 and 8 was elucidated by spectral means. Complete assignments of the ¹H NMR data for 5, 6, sarracine (7), and 8 were made using one-dimensional and two-dimensional NMR experiments and by application of the iterative full spin analysis of the PERCH NMR software.

Original language	English
Pages (from-to)	251-257
Number of pages	7
Journal	Magnetic Resonance in Chemistry
Volume	52
Issue number	5
DOIs	https://doi.org/10.1002/mrc.4054
State	Published - May 2014

Keywords

1β-angeloyloxyeudesm-7-ene-4β,9α- diol
7β-angeloyloxy-1-methylene-8α-pyrrolizidine
Senecio polypodioides
neosarracine N-oxide
sarracine
sarracine N-oxide

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title = "Complete 1H NMR assignments of pyrrolizidine alkaloids and a new eudesmanoid from Senecio polypodioides",

abstract = "Chemical investigation of the aerial parts of Senecio polypodioides lead to the isolation of the new eudesmanoid 1β-angeloyloxyeudesm-7-ene-4β, 9α-diol (1) and the known dirhamnosyl flavonoid lespidin (3), while from roots, the known 7β-angeloyloxy-1-methylene-8α-pyrrolizidine (5) and sarracine N-oxide (6), as well as the new neosarracine N-oxide (8), were obtained. The structure of 1 and 8 was elucidated by spectral means. Complete assignments of the 1H NMR data for 5, 6, sarracine (7), and 8 were made using one-dimensional and two-dimensional NMR experiments and by application of the iterative full spin analysis of the PERCH NMR software.",

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author = "Claudia Villanueva-Ca{\~n}ongo and Nury P{\'e}rez-Hern{\'a}ndez and Beatriz Hern{\'a}ndez-Carlos and Ernestina Cedillo-Portugal and Pedro Joseph-Nathan and Eleuterio Burgue{\~n}o-Tapia",

year = "2014",

month = may,

doi = "10.1002/mrc.4054",

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AU - Villanueva-Cañongo, Claudia

AU - Pérez-Hernández, Nury

AU - Hernández-Carlos, Beatriz

AU - Cedillo-Portugal, Ernestina

AU - Joseph-Nathan, Pedro

AU - Burgueño-Tapia, Eleuterio

PY - 2014/5

Y1 - 2014/5

N2 - Chemical investigation of the aerial parts of Senecio polypodioides lead to the isolation of the new eudesmanoid 1β-angeloyloxyeudesm-7-ene-4β, 9α-diol (1) and the known dirhamnosyl flavonoid lespidin (3), while from roots, the known 7β-angeloyloxy-1-methylene-8α-pyrrolizidine (5) and sarracine N-oxide (6), as well as the new neosarracine N-oxide (8), were obtained. The structure of 1 and 8 was elucidated by spectral means. Complete assignments of the 1H NMR data for 5, 6, sarracine (7), and 8 were made using one-dimensional and two-dimensional NMR experiments and by application of the iterative full spin analysis of the PERCH NMR software.

AB - Chemical investigation of the aerial parts of Senecio polypodioides lead to the isolation of the new eudesmanoid 1β-angeloyloxyeudesm-7-ene-4β, 9α-diol (1) and the known dirhamnosyl flavonoid lespidin (3), while from roots, the known 7β-angeloyloxy-1-methylene-8α-pyrrolizidine (5) and sarracine N-oxide (6), as well as the new neosarracine N-oxide (8), were obtained. The structure of 1 and 8 was elucidated by spectral means. Complete assignments of the 1H NMR data for 5, 6, sarracine (7), and 8 were made using one-dimensional and two-dimensional NMR experiments and by application of the iterative full spin analysis of the PERCH NMR software.

KW - 1β-angeloyloxyeudesm-7-ene-4β,9α- diol

KW - 7β-angeloyloxy-1-methylene-8α-pyrrolizidine

KW - Senecio polypodioides

KW - neosarracine N-oxide

KW - sarracine

KW - sarracine N-oxide

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U2 - 10.1002/mrc.4054

DO - 10.1002/mrc.4054

M3 - Artículo

SN - 0749-1581

VL - 52

SP - 251

EP - 257

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

IS - 5

ER -

Complete ¹H NMR assignments of pyrrolizidine alkaloids and a new eudesmanoid from Senecio polypodioides

Abstract

Keywords

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