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

Mayra Rengifo Carrillo, Anne Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Laurent Pouységu, Stéphane Quideau, Carmelo Rosquete Porcar, Marie Aleth Lacaille-Dubois

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)166-173
Number of pages8
JournalPhytochemistry
Volume140
DOIs
Publication statusPublished - Aug 1 2017

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Rosales
Glycosides
Gold
gold
Stars
glycosides
Esters
esters
Pittosporum
chemotaxonomy
Acids
acids
Saponins
Phytochemicals
cultivars
saponins
phytopharmaceuticals
Mass spectrometry
Mass Spectrometry
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Cite this

Oleanane-type glycosides from Pittosporum tenuifolium “variegatum” and P. tenuifolium “gold star”. / Rengifo Carrillo, Mayra; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Pouységu, Laurent; Quideau, Stéphane; Rosquete Porcar, Carmelo; Lacaille-Dubois, Marie Aleth.

In: Phytochemistry, Vol. 140, 01.08.2017, p. 166-173.

Research output: Contribution to journalArticle

Rengifo Carrillo, M, Mitaine-Offer, AC, Miyamoto, T, Tanaka, C, Pouységu, L, Quideau, S, Rosquete Porcar, C & Lacaille-Dubois, MA 2017, 'Oleanane-type glycosides from Pittosporum tenuifolium “variegatum” and P. tenuifolium “gold star”', Phytochemistry, vol. 140, pp. 166-173. https://doi.org/10.1016/j.phytochem.2017.04.013
Rengifo Carrillo, Mayra ; Mitaine-Offer, Anne Claire ; Miyamoto, Tomofumi ; Tanaka, Chiaki ; Pouységu, Laurent ; Quideau, Stéphane ; Rosquete Porcar, Carmelo ; Lacaille-Dubois, Marie Aleth. / Oleanane-type glycosides from Pittosporum tenuifolium “variegatum” and P. tenuifolium “gold star”. In: Phytochemistry. 2017 ; Vol. 140. pp. 166-173.
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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.",
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AU - Miyamoto, Tomofumi

AU - Tanaka, Chiaki

AU - Pouységu, Laurent

AU - Quideau, Stéphane

AU - Rosquete Porcar, Carmelo

AU - Lacaille-Dubois, Marie Aleth

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N2 - 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.

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