Structural analysis of oleanane‐type saponins from the roots of <i>Wisteria frutescens</i>

Champy, Anne Sophie; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Papini, Anna Maria; Lacaille‐Dubois, Marie‐Aleth

doi:10.1002/mrc.4550

Cited by 4 publications

(4 citation statements)

References 8 publications

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“… H (J in Hz) (br s), confirmed the -equatorial orientation of the H-22. The structure of the aglycon of 1 was thus recognized to be the 22-Oacetyl-3,22,24-trihydroxyolean-12-en-30-oic acid, previously described in W. frutescens [2], W. brachybotrys [5], and Millettia speciosa Champ. ex Benth.…”

Section:  Cmentioning

confidence: 73%

“…[19] or Medicago L. [20] for example, showed that monodesmosidic oleanane-type saponins with glucuronic acid linked at the C-3 position are very common to this family. More specifically, the sequence 3-O--D-glucuronopyranosyl-22-Oacetyl-3,22,24-trihydroxyolean-12-en-30-oic acid is found in saponins isolated from Wisteria [2,5], Derris Wall. [21], and Millettia Wight & Arn.…”

Section:  Cmentioning

confidence: 99%

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Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”

Champy

Mitaine-Offer

Paululat

et al. 2017

Natural Product Communications

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Five oleanane-type saponins were isolated from two cultivars of Wisteria floribunda (Willd.) DC. (Fabaceae): From the roots of Wisteria floribunda “macrobotrys”, one new oleanane derivative elucidated as 3- O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl-22- O-acetyl-3p,22p,24-trihydroxyolean-12-en-30-oic acid, and two known glycosides, and from the roots of Wisteria floribunda “rosea”, two known ones. Their structures were elucidated by a detailed 600 MHz NMR analysis including 1D and 2D NMR (1H, 13C, COSY, TOCSY, ROESY, HSQC, HMBC) experiments and mass spectrometry. Chemotaxonomic conclusions were proposed.

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Section:  Cmentioning

confidence: 73%

Section:  Cmentioning

confidence: 99%

Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”

Champy

Mitaine-Offer

Paululat

et al. 2017

Natural Product Communications

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“…and Glycyrrhiza L. belong to the Faboideae subfamily, so they are phylogenetically very close [8]. Moreover, oleanane-type glycosides isolated from Wisteria species like W. frutescens [9], W. floribunda cultivars [10], and W. brachybotrys [11], showed some structural similarities with glycyrrhizin [12]: a β-carboxyl group at position C-30, a ketone function, and a 3-O-β-D-glucuronopyranosyl moiety.…”

Section: Introductionmentioning

confidence: 99%

Activation of a Sweet Taste Receptor by Oleanane-Type Glycosides from Wisteria sinensis

et al. 2022

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The phytochemical study of Wisteria sinensis (Sims) DC. (Fabaceae), commonly known as the Chinese Wisteria, led to the isolation of seven oleanane-type glycosides from an aqueous-ethanolic extract of the roots. Among the seven isolated saponins, two have never been reported before: 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl-22-O-acetylolean-12-ene-3β,16β,22β,30-tetrol, and 3-O-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosylwistariasapogenol A. Based on the close structures between the saponins from W. sinensis, and the glycyrrhizin from licorice, the stimulation of the sweet taste receptor TAS1R2/TAS1R3 by these glycosides was evaluated.

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“…3 Previous phytochemical studies on P. eetveldeana showed the presence of saponins in the seeds 4 with oleanolic acid or hederagenin as aglycone and glucose, rhamnose, and arabinose as sugar units. In a continuation of our studies on natural saponins from the plants of the Fabaceae family, 5,6 we decided to examine the saponins from the stem bark of P. eetveldeana De Wild. & Th.…”

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Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

Pertuit

Kapundu

Mitaine-Offer

et al. 2019

Natural Product Communications

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Two previously undescribed triterpenoid saponins together with 4 known ones were isolated from the stem bark of Pentaclethra eetveldeana De Wild. & Th. Dur. Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments in combination with mass spectrometry as 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosylhederagenin.

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Structural analysis of oleanane‐type saponins from the roots of Wisteria frutescens

Cited by 4 publications

References 8 publications

Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”

Triterpene Saponins from Wisteria floribunda “macrobotrys” and “rosea”

Activation of a Sweet Taste Receptor by Oleanane-Type Glycosides from Wisteria sinensis

Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

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