Triterpenoid Saponins from the Cultivar “Green Elf” of Pittosporum tenuifolium |
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Authors: | David Pertuit Anne-Claire Mitaine-Offer Tomofumi Miyamoto Chiaki Tanaka Christine Belloir Loïc Briand Marie-Aleth Lacaille-Dubois |
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Institution: | 1.PEPITE EA 4267, Laboratoire de Pharmacognosie, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, BP 87900, CEDEX, 21079 Dijon, France; (D.P.); (M.-A.L.-D.);2.Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812-8582, Japan; (T.M.); (C.T.);3.Centre des Sciences du Goût et de l’Alimentation, AgroSup Dijon, CNRS, INRAE, Université de Bourgogne Franche-Comté, CEDEX, 21065 Dijon, France; (C.B.); (L.B.) |
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Abstract: | Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic Pittosporum tenuifolium (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-O-β-d-glucopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, 3-O-β-d-galactopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and the known 3-O-β-d-glucopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C (Eryngioside L). From the roots, the known 3-O-β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyloleanolic acid (Sandrosaponin X) was identified. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR experiments and mass spectrometry (ESI-MS). According to their structural similarities with gymnemic acids, the inhibitory activities on the sweet taste TAS1R2/TAS1R3 receptor of an aqueous ethanolic extract of the leaves and roots, a crude saponin mixture, 3-O-β-d-glucopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and Eryngioside L were evaluated. |
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Keywords: | Pittosporum tenuifolium Pittosporaceae barringtogenol C TAS1R2/TASR3 sweet taste taste inhibitor |
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