Repositorio
Institucional

Baggio, Ricardo

Paz, Cristian#Heydenreich, Matthias#Schmidt, Bernd#Vadra, Nahir

Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria

INT UNION CRYSTALLOGRAPHY

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY

en

As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new beta-agarofuran sesquiterpenes, namely (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9-dihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b] oxepine-5,10-diylbis(furan-3-carboxylate), C27H32O11, (II), (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-9-hydroxy-2,2,5a, 9-tetramethyloctahydro-2H-3,9a-methanobenzo[ b] oxepine-5,10-diyl bis(furan-3-carboxylate), C27H32O10, (III), and (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-10-(benzoyloxy)-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate, C29H34O9, (IV), obtained from the seeds of Maytenus boaria and closely associated with a recently published relative [Paz et al. (2017). Acta Cryst. C73, 451-457]. In the (isomorphic) structures of (II) and (III), the central decalin system is esterified with an acetate group at site 1 and furoate groups at sites 6 and 9, and differ at site 8, with an OH group in (II) and no substituent in (III). This position is also unsubstituted in (IV), with site 6 being occupied by a benzoate group. The chirality of the skeletons is described as 1S, 4S, 5S, 6R, 7R, 8R, 9R, 10S in (II) and 1S, 4S, 5S, 6R, 7R, 9S, 10S in (III) and (IV), matching the chirality suggested by NMR studies. This difference in the chirality sequence among the title structures (in spite of the fact that the three skeletons are absolutely isostructural) is due to the differences in the environment of site 8, i.e. OH in (II) and H in (III) and (IV). This diversity in substitution, in turn, is responsible for the differences in the hydrogen-bonding schemes, which is discussed.

Artículo original

Funding for this research was provided by: University of La Frontera, Ministerio de Educacion of Chile (Program MECE Superior Education), ANPCyT (project No. PME 2006-01113, for the purchase of the Oxford Gemini CCD diffractometer).

El financiamiento para esta investigación fue otorgado por: Universidad de La Frontera, Ministerio de Educación de Chile (Programa MECE Educación Superior), ANPCyT (proyecto N° PME 2006-01113, para la compra del difractómetro CCD Oxford Gemini).

10.1107/S2053229618005429

pdf

Celastraceae# Maytenus boaria# sesquiterpene# dihydro-beta-agarofuran# crystal structure# NMR# DSC

http://dx.doi.org/10.1107/S2053229618005429

Chemistry, Multidisciplinary# Crystallography

Celastráceas# Maytenus boaria# sesquiterpeno# dihidro-beta-agarofurano# estructura cristalina# RMN# DSC

Química Orgánica

Otras Especialidades de la Química

Botánica

WOS:000431429300007

Three new dihydro-β-agarofuran sesquiterpenes from the seeds of <i>Maytenus boaria</i>

http://hdl.handle.net/11336/182495

Artículo original

version publicada

INT UNION CRYSTALLOGRAPHY

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY

Química Multidisciplinaria# Cristalografía

2053-2296

en

UFRO#MINEDUC MECE#ANPCyT 2006-01113

UFRO

MINEDUC MECESUP

ANPCyT PME 2006-01113

Funding for this research was provided by: University of La Frontera, Ministerio de Educacion of Chile (Program MECE Superior Education), ANPCyT (project No. PME 2006-01113, for the purchase of the Oxford Gemini CCD diffractometer).

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dorada#verde

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