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

As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new β-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-diyl bis(furan-3-carboxylate),...

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Autores principales:	Paz, C., Heydenreich, M., Schmidt, B., Vadra, N., Baggio, R.
Formato:	JOUR
Materias:	Celastraceae crystal structure dihydro-β-agarofuran DSC Maytenus boaria NMR sesquiterpene Aromatic compounds Carboxylation Chirality Hydrogen bonds Metabolites Musculoskeletal system Nuclear magnetic resonance Olefins Organic pollutants Organic solvents Acetate groups Isostructural NMR studies OH group Secondary metabolites Sesquiterpenes Crystal structure dihydroagarofuran furan furan derivative chemistry hydrogen bond isolation and purification Maytenus nuclear magnetic resonance spectroscopy plant seed stereoisomerism X ray crystallography Crystallography, X-Ray Furans Hydrogen Bonding Magnetic Resonance Spectroscopy Seeds Stereoisomerism
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_20532296_v74_n5_p564_Paz
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_20532296_v74_n5_p564_Paz
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spelling	todo:paper_20532296_v74_n5_p564_Paz2023-10-03T16:39:04Z Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria Paz, C. Heydenreich, M. Schmidt, B. Vadra, N. Baggio, R. Celastraceae crystal structure dihydro-β-agarofuran DSC Maytenus boaria NMR sesquiterpene Aromatic compounds Carboxylation Chirality Hydrogen bonds Metabolites Musculoskeletal system Nuclear magnetic resonance Olefins Organic pollutants Organic solvents Acetate groups Celastraceae Isostructural Maytenus boaria NMR studies OH group Secondary metabolites Sesquiterpenes Crystal structure dihydroagarofuran furan furan derivative sesquiterpene chemistry hydrogen bond isolation and purification Maytenus nuclear magnetic resonance spectroscopy plant seed stereoisomerism X ray crystallography Crystallography, X-Ray Furans Hydrogen Bonding Magnetic Resonance Spectroscopy Maytenus Seeds Sesquiterpenes Stereoisomerism As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new β-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-diyl bis(furan-3-carboxylate), C 27 H 32 O 11 , (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), C 27 H 32 O 10 , (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, C 29 H 34 O 9 , (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. © International Union of Crystallography, 2018 JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_20532296_v74_n5_p564_Paz
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Celastraceae crystal structure dihydro-β-agarofuran DSC Maytenus boaria NMR sesquiterpene Aromatic compounds Carboxylation Chirality Hydrogen bonds Metabolites Musculoskeletal system Nuclear magnetic resonance Olefins Organic pollutants Organic solvents Acetate groups Celastraceae Isostructural Maytenus boaria NMR studies OH group Secondary metabolites Sesquiterpenes Crystal structure dihydroagarofuran furan furan derivative sesquiterpene chemistry hydrogen bond isolation and purification Maytenus nuclear magnetic resonance spectroscopy plant seed stereoisomerism X ray crystallography Crystallography, X-Ray Furans Hydrogen Bonding Magnetic Resonance Spectroscopy Maytenus Seeds Sesquiterpenes Stereoisomerism
spellingShingle	Celastraceae crystal structure dihydro-β-agarofuran DSC Maytenus boaria NMR sesquiterpene Aromatic compounds Carboxylation Chirality Hydrogen bonds Metabolites Musculoskeletal system Nuclear magnetic resonance Olefins Organic pollutants Organic solvents Acetate groups Celastraceae Isostructural Maytenus boaria NMR studies OH group Secondary metabolites Sesquiterpenes Crystal structure dihydroagarofuran furan furan derivative sesquiterpene chemistry hydrogen bond isolation and purification Maytenus nuclear magnetic resonance spectroscopy plant seed stereoisomerism X ray crystallography Crystallography, X-Ray Furans Hydrogen Bonding Magnetic Resonance Spectroscopy Maytenus Seeds Sesquiterpenes Stereoisomerism Paz, C. Heydenreich, M. Schmidt, B. Vadra, N. Baggio, R. Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria
topic_facet	Celastraceae crystal structure dihydro-β-agarofuran DSC Maytenus boaria NMR sesquiterpene Aromatic compounds Carboxylation Chirality Hydrogen bonds Metabolites Musculoskeletal system Nuclear magnetic resonance Olefins Organic pollutants Organic solvents Acetate groups Celastraceae Isostructural Maytenus boaria NMR studies OH group Secondary metabolites Sesquiterpenes Crystal structure dihydroagarofuran furan furan derivative sesquiterpene chemistry hydrogen bond isolation and purification Maytenus nuclear magnetic resonance spectroscopy plant seed stereoisomerism X ray crystallography Crystallography, X-Ray Furans Hydrogen Bonding Magnetic Resonance Spectroscopy Maytenus Seeds Sesquiterpenes Stereoisomerism
description	As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new β-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-diyl bis(furan-3-carboxylate), C 27 H 32 O 11 , (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), C 27 H 32 O 10 , (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, C 29 H 34 O 9 , (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. © International Union of Crystallography, 2018
format	JOUR
author	Paz, C. Heydenreich, M. Schmidt, B. Vadra, N. Baggio, R.
author_facet	Paz, C. Heydenreich, M. Schmidt, B. Vadra, N. Baggio, R.
author_sort	Paz, C.
title	Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria
title_short	Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria
title_full	Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria
title_fullStr	Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria
title_full_unstemmed	Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria
title_sort	three new dihydro-β-agarofuran sesquiterpenes from the seeds of maytenus boaria
url	http://hdl.handle.net/20.500.12110/paper_20532296_v74_n5_p564_Paz
work_keys_str_mv	AT pazc threenewdihydrobagarofuransesquiterpenesfromtheseedsofmaytenusboaria AT heydenreichm threenewdihydrobagarofuransesquiterpenesfromtheseedsofmaytenusboaria AT schmidtb threenewdihydrobagarofuransesquiterpenesfromtheseedsofmaytenusboaria AT vadran threenewdihydrobagarofuransesquiterpenesfromtheseedsofmaytenusboaria AT baggior threenewdihydrobagarofuransesquiterpenesfromtheseedsofmaytenusboaria
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Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria

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