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

• Published in: Magnetic resonance in chemistry Vol. 52; no. 5; pp. 251 - 257
• Main Authors: Villanueva-Cañongo, Claudia, Pérez-Hernández, Nury, Hernández-Carlos, Beatriz, Cedillo-Portugal, Ernestina, Joseph-Nathan, Pedro, Burgueño-Tapia, Eleuterio
• Format: Journal Article
• Language: English
• Published: England Blackwell Publishing Ltd 01.05.2014; Wiley Subscription Services, Inc
• Subjects: 1β-angeloyloxyeudesm-7-ene-4β; 1β‐angeloyloxyeudesm‐7‐ene‐4β,9α‐diol; 7β-angeloyloxy-1-methylene-8α-pyrrolizidine; 9α-diol; iterative 1H NMR analysis; Magnetic Resonance Spectroscopy; Molecular Structure; neosarracine N-oxide; Plant Roots - chemistry; Protons; Pyrrolizidine Alkaloids - chemistry; Pyrrolizidine Alkaloids - isolation & purification; Reference Standards; sarracine; sarracine N-oxide; Senecio - chemistry; Senecio polypodioides; Sesquiterpenes, Eudesmane - chemistry; Sesquiterpenes, Eudesmane - isolation & purification; Software; iterative 1H NMR analysis; 7β-angeloyloxy-1-methylene-8α-pyrrolizidine; neosarracine N-oxide; sarracine; Senecio polypodioides; 1β-angeloyloxyeudesm-7-ene-4β,9α-diol; sarracine N-oxide
• ISSN: 0749-1581; 1097-458X
• DOI: 10.1002/mrc.4054

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. Copyright © 2014 John Wiley & Sons, Ltd. Chemical investigation of Senecio polypodioides lead to the isolation of new neosarracine N‐oxide (8) and eudesmanoid 1β‐angeloyloxyeudesm‐7‐ene‐4β,9α‐diol (1), as well as the known lespidin (3), 7β‐angeloyloxy‐1‐methylene‐8α‐pyrrolizidine (5), and sarracine N‐oxide (6). Complete 1H NMR assignments of 5, 6, sarracine (7), and 8 using iterative full spin analysis of the PERCH NMR software were done.