Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)

Vázquez,Erika; Martínez,Esteban M.; Cogordán,Juan Antonio; Delgado,Guillermo

Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)

Lupeol, oleanolic acid, stigmasterol, β-sitosterol, β-sitosteryl-β-D-glucopyranoside, catechin, epicatechin, and 8-C-β-D-glucopyranosylapigenin (vitexin) were isolated from the acetonic extract of the leaves of Ochroma pyramidale (balsa wood, Bombacaceae), a tree noted by its exceedingly light wood. ¹H and 13C NMR of 8-C-β-D-glucopyranosyl-apigenin (vitexin) at room temperature exhibited doubling of some signals, suggesting the presence of atropisomers. ¹H NMR spectra at 70 °C showed one set of signals, confirming the presence of rotational isomers at room temperature. Molecular modelling using AM1 methods, established the two conformations of minimum energy for vitexin, which correspond to the -ac (ω = -94 °) and +ac (ω = + 96 °) arrangement along the C(2")-C(1")-C(8)-C(7) bonds.

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Main Authors:	Vázquez,Erika, Martínez,Esteban M., Cogordán,Juan Antonio, Delgado,Guillermo
Format:	Digital revista
Language:	English
Published:	Sociedad Química de México A.C. 2002
Online Access:	http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0583-76932002000300014
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spelling	oai:scielo:S0583-769320020003000142017-02-15Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)Vázquez,ErikaMartínez,Esteban M.Cogordán,Juan AntonioDelgado,Guillermo Ochroma pyramidale balsa wood Bombacaceae triterpenes phenols sterols conformational analysis mollecular modeling vitexin Lupeol, oleanolic acid, stigmasterol, β-sitosterol, β-sitosteryl-β-D-glucopyranoside, catechin, epicatechin, and 8-C-β-D-glucopyranosylapigenin (vitexin) were isolated from the acetonic extract of the leaves of Ochroma pyramidale (balsa wood, Bombacaceae), a tree noted by its exceedingly light wood. ¹H and 13C NMR of 8-C-β-D-glucopyranosyl-apigenin (vitexin) at room temperature exhibited doubling of some signals, suggesting the presence of atropisomers. ¹H NMR spectra at 70 °C showed one set of signals, confirming the presence of rotational isomers at room temperature. Molecular modelling using AM1 methods, established the two conformations of minimum energy for vitexin, which correspond to the -ac (ω = -94 °) and +ac (ω = + 96 °) arrangement along the C(2")-C(1")-C(8)-C(7) bonds.info:eu-repo/semantics/openAccessSociedad Química de México A.C.Revista de la Sociedad Química de México v.46 n.3 20022002-09-01info:eu-repo/semantics/articletext/htmlhttp://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0583-76932002000300014en
institution	SCIELO
collection	OJS
country	México
countrycode	MX
component	Revista
access	En linea
databasecode	rev-scielo-mx
tag	revista
region	America del Norte
libraryname	SciELO
language	English
format	Digital
author	Vázquez,Erika Martínez,Esteban M. Cogordán,Juan Antonio Delgado,Guillermo
spellingShingle	Vázquez,Erika Martínez,Esteban M. Cogordán,Juan Antonio Delgado,Guillermo Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)
author_facet	Vázquez,Erika Martínez,Esteban M. Cogordán,Juan Antonio Delgado,Guillermo
author_sort	Vázquez,Erika
title	Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)
title_short	Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)
title_full	Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)
title_fullStr	Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)
title_full_unstemmed	Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)
title_sort	triterpenes, phenols, and other constituents from the leaves of ochroma pyramidale (balsa wood, bombacaceae): preferred conformations of 8-c-β-d-glucopyranosyl-apigenin (vitexin)
description	Lupeol, oleanolic acid, stigmasterol, β-sitosterol, β-sitosteryl-β-D-glucopyranoside, catechin, epicatechin, and 8-C-β-D-glucopyranosylapigenin (vitexin) were isolated from the acetonic extract of the leaves of Ochroma pyramidale (balsa wood, Bombacaceae), a tree noted by its exceedingly light wood. ¹H and 13C NMR of 8-C-β-D-glucopyranosyl-apigenin (vitexin) at room temperature exhibited doubling of some signals, suggesting the presence of atropisomers. ¹H NMR spectra at 70 °C showed one set of signals, confirming the presence of rotational isomers at room temperature. Molecular modelling using AM1 methods, established the two conformations of minimum energy for vitexin, which correspond to the -ac (ω = -94 °) and +ac (ω = + 96 °) arrangement along the C(2")-C(1")-C(8)-C(7) bonds.
publisher	Sociedad Química de México A.C.
publishDate	2002
url	http://www.scielo.org.mx/scielo.php?script=sci_arttext&pid=S0583-76932002000300014
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Triterpenes, Phenols, and Other Constituents from the leaves of Ochroma pyramidale (Balsa Wood, Bombacaceae): Preferred Conformations of 8-C-β-D-Glucopyranosyl-apigenin (vitexin)

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