Millettia dubia De Wild. (Fabaceae): Structural analysis of the oleanane-type glycosides and stimulation of the sweet taste receptors TAS1R2/TAS1R3.

From the root barks of a Central African tree Millettia dubia De Wild. (Fabaceae), ten previously undescribed oleanane-type glycosides were isolated by various chromatographic protocols. Their structures were elucidated by spectroscopic methods, mainly 2D NMR experiments and mass spectrometry, as mono- and bidesmosidic glycosides of mesembryanthemoidigenic acid, hederagenin and oleanolic acid.

Phytochemical, Geographical, and Pharmacological Retrospect of Genus .

Background: Genus (Apiaceae) known as hedge parsley, encompasses 11-13 species distributed worldwide and shows potential pharmacological uses. Its phytochemical pattern is highly diversified including many phenolic and terpenic compounds.

Objective: This research-review provides new highlighting of structural organizations, structure-activity trends, taxonomical, tissue and geographical distribution of phytocompounds of genus from extensive statistical analyses of available data.

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

The phytochemical study of (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--α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranosyl-22--acetylolean-12-ene-3β,16β,22β,30-tetrol, and 3--β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosylwistariasapogenol A.

Oleanane-type glycosides isolated from the trunk barks of the Central African tree Millettia laurentii.

Seven previously undescribed oleanane-type glycosides were isolated from the trunk barks of a Central African tree named Millettia laurentii De Wild (Fabaceae). After the extraction from the barks, the isolation and purification of these compounds were achieved using various solid/liquid chromatographic methods. Their structures were established mainly by 1D and 2D NMR (COSY, TOCSY, ROESY, HSQC, HMBC) and mass spectrometry (ESI-MS), as 3-O-β-D-glucuronopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-β-D-glucuronopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-[β-d-xylopyranosyl-(1 → 2)]-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 2)]-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosylechinocystic acid, 3-O-α-L-arabinofuranosyl-(1 → 2)-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyloleanolic acid, 3-O-β-D-apiofuranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 2)]-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyloleanolic acid.

Triterpenoid Saponins from the Cultivar "Green Elf" of .

Four oleanane-type glycosides were isolated from a horticultural cultivar "Green Elf" of the endemic (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3--β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C, 3--β-d-galactopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C, and the known 3--β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21--angeloyl-28--acetylbarringtogenol C (Eryngioside L). From the roots, the known 3--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).