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Phytochemistry. 2017 Aug;140:166-173. doi: 10.1016/j.phytochem.2017.04.013. Epub 2017 May 10.

Oleanane-type glycosides from Pittosporum tenuifolium "variegatum" and P. tenuifolium "gold star".

Author information

1
Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France; Laboratorio de Productos Naturales, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela.
2
Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France.
3
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, 812-8582, Japan.
4
Institut des Sciences Moléculaires, CNRS-UMR 5255 & Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 rue Robert Escarpit, 33607 Pessac Cedex, France.
5
Laboratorio de Productos Naturales, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida 5101, Venezuela.
6
Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd Jeanne d'Arc, BP 87900, 21079 Dijon Cedex, France. Electronic address: m-a.lacaille-dubois@u-bourgogne.fr.

Abstract

The phytochemical study of two cultivars of Pittosporum tenuifolium Banks & Sol. ex Gaertn, "variegatum" and "gold star", led to the isolation of eight oleanane-type glycosides: seven previously undescribed and a known one. Their aglycons are oxygenated oleanane derivatives as barringtogenol C, camelliagenin A, hederagenin, and 22α-hydroxyoleanolic acid. Their structures were established by 2D NMR spectroscopic techniques and mass spectrometry as 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21-O-angeloyl-22-O-acetylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-21,22-di-O-angeloylbarringtogenol C, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl-22-O-angeloylcamelliagenin A, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-22-O-[(6-O-acetyl)-β-D-glucopyranosyl]camelliagenin A, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 4)]-β-D-glucuronopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-arabinofuranosyl-(1 → 4)-β-D-glucuronopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 4)]-β-D-glucuronopyranosyl-22α-hydroxyoleanolic acid 28-O-β-D-glucopyranosyl ester, and the known ilexoside XLIX. These results represent a significative contribution to the chemotaxonomy of the genus Pittosporum, highlighting hederagenin-type saponins as chemotaxonomic markers of P. tenuifolium cultivars.

KEYWORDS:

NMR; Oleanane-type glycosides; Pittosporaceae; Pittosporum tenuifolium “gold star”; Pittosporum tenuifolium “variegatum”

PMID:
28500929
DOI:
10.1016/j.phytochem.2017.04.013
[Indexed for MEDLINE]

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