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).

Steroidal glycosides from the Vietnamese cultivar Cordyline fruticosa "Fairchild red".

A phytochemical study of Cordyline fruticosa "Fairchild red" (Asparagaceae) from Vietnam, led to the isolation of fourteen steroidal glycosides, including twelve previously undescribed along with two known ones. Ten compounds were obtained by successive solid/liquid chromatographic methods from an aqueous-ethanolic extract of the roots, and four from the aerial parts. Their structures were elucidated mainly by spectroscopic analysis 2D NMR and mass spectroscopy (ESI-MS), as spirostanol glycosides, 5α-spirost-25(27)-ene-1β,3β,4α-triol 1-O-β-D-fucopyranoside, 5α-spirost-(25)27-ene-1β,3β,4α-triol 1-O-β-D-xylopyranoside, 5α-spirost-(25)27-ene-1β,3β,4α-triol 1-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranoside, 5α-spirost-(25)27-ene-1β,3β,4α-triol 1-O-α-L-rhamnopyranosyl-(1 → 2)-(4-O-sulfo)-β-D-fucopyranoside, 5α-spirost-25(27)-ene-1β,3β-diol 1-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranoside, and 5α-spirost-25(27)-ene-1β,3β-diol 1-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranoside.

Anti-phytopathogen terpenoid glycosides from the root bark of Chytranthus macrobotrys and Radlkofera calodendron.

Chytranthus macrobotrys and Radlkofera calodendron are two Sapindaceae characterized by a lack of phytochemical data. Both root barks from the two Sapindaceae species were processed by ethanol extraction followed by the isolation of their primary constituents by liquid chromatography. This process yielded four previously undescribed terpenoid glycosides together with eight known analogues.

β-Amyrin Synthase1 Controls the Accumulation of the Major Saponins Present in Pea (Pisum sativum).

The use of pulses as ingredients for the production of food products rich in plant proteins is increasing. However, protein fractions prepared from pea or other pulses contain significant amounts of saponins, glycosylated triterpenes that can impart an undesirable bitter taste when used as an ingredient in foodstuffs. In this article, we describe the identification and characterization of a gene involved in saponin biosynthesis during pea seed development, by screening mutants obtained from two Pisum sativum TILLING (Targeting Induced Local Lesions IN Genomes) populations in two different genetic backgrounds.

A review on the phytopharmacological studies of the genus Polygala.

Ethnopharmacological Relevance: The genus Polygala, the most representative genus of the Polygalaceae family, comprises more than 600 species from all over the world of which around 40 are distributed in China, some of them, being used in the Traditional Chinese Medicine system.

Aim Of The Review: We intend to discuss the current knowledge about the traditional uses, and the newest phytochemical and pharmacological achievements with tentative elucidation of the mechanism of action on the genus Polygala covering the period 2013-2019 to provide a scientific support to the traditional uses, and to critically analyze the reported studies to obtain new insights for further researches.

Materials And Methods: The data were systematically collected from the scientific electronic data bases including SciFinder, Scopus, Elsevier, PubMed and Google Scholar.

Cytotoxic glycosides from the roots of Weigela x "Bristol Ruby".

Seven oleanane-type glycosides were extracted and isolated by various chromatographic methods from the roots of Weigela x "Bristol Ruby" (1-7), six previously undescribed (1-6) and a known one (7). Their structures were assigned by spectroscopic analysis mainly 2D NMR and mass spectrometry (ESIMS). Selected triterpenoid glycosides (1-3, 6, 7) displayed a good cytotoxic activity against a mouse colon cancer cell line CT26.

Updated insights into the mechanism of action and clinical profile of the immunoadjuvant QS-21: A review.

Background: Vaccine adjuvants are compounds that significantly enhance/prolong the immune response to a co-administered antigen. The limitations of the use of aluminium salts that are unable to elicite cell responses against intracellular pathogens such as those causing malaria, tuberculosis, or AIDS, have driven the development of new alternative adjuvants such as QS-21, a triterpene saponin purified from Quillaja saponaria.

Purpose: The aim of this review is to attempt to clarify the mechanism of action of QS-21 through either receptors or signaling pathways in vitro and in vivo with special emphasis on the co-administration with other immunostimulants in new adjuvant formulations, called adjuvant systems (AS).

Hederagenin glycosides from the fruits of Blighia unijugata.

A phytochemical investigation of Blighia unijugata led to the isolation of eleven hederagenin glycosides. Among these compounds, six are previously undescribed, two are described in their native forms for the first time and three are known whereas firstly isolated from Blighia unijugata. The structure of the undescribed compounds was elucidated on the basis of 2D NMR and mass spectrometry analyses as 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-3-O-acetyl-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester and 3-O-β-D-xylopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester.

Steroidal saponins from the aerial parts of Cordyline fruticosa L. var. strawberries.

A new sulfated steroidal derivative (fruticogenin A: 1-sulfo-australigenin-3-sodium sulphate, 1) and three new steroidal saponins named fruticoside K (3-sulfo-spirostan-25(27)-ene-1β,3β-diol-1-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-fucopyranoside], 2), fruticoside L (3-sulfo-spirostan-25(27)-ene-1β,3β,6α-triol-1-O-[α-L-rhamnopyranosyl-(1 → 4)-β-D-fucopyranoside], 3) and fruticoside M (spirostan-25(27)-ene-1β,3α-diol-1-O-[α-L-rhamnopyranosyl-(1 → 2)-α-L-rhamnopyranoside], 4) were isolated from the aerial parts of Cordyline fruticosa L. var. strawberries.

Steroidal glycosides from Ornithogalum dubium Houtt.

The phytochemical study of Ornithogalum dubium Houtt. (Asparagaceae) led to the isolation of five undescribed steroidal glycosides together with two known ones. Their structures were established by using NMR analysis and mass spectrometry as (25R)-3β-hydroxyspirost-5-en-1β-yl O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranoside, (25S)-3β-hydroxyspirost-5-en-1β-yl O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, (22S)-16β-[(α-L-rhamnopyranosyl)oxy]-22-hydroxycholest-5-en-3β-yl O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside, (22S,23S)-1β,3β,11α,16β,23-pentahydroxy-5α-cholest-24-en-22β-yl β-D-glucopyranoside, (22S,23S)-3β-[(β-D-glucopyranosyl)oxy]-22,23-dihydroxy-5α-cholest-24-en-16β-yl O-α-L-rhamnopyranosyl)-(1 → 4)-β-D-glucopyranoside.

Terpenoid glycosides from the root's barks of Eriocoelum microspermum Radlk. ex Engl.

Eight undescribed triterpenoid saponins together with a known one, and two undescribed sesquiterpene glycosides were isolated from root's barks of Eriocoelum microspermum. Their structures were elucidated by spectroscopic methods including 1D and 2D experiments in combinaison with mass spectrometry as 3-O-α-L-rhamnopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 4)-[α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin 28-O-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-β-D-xylopyranosyl-(1 → 4)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-α-L-arabinopyranosylhederagenin, 1-O-{β-D-xylopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 6)}-[β-D-xylopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(2E,6E)-farnes-1-ol, 1-O-{β-D-glucopyranosyl-(1 → 3)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 6)}-[β-D-xylopyranosyl-(1 → 3)]-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl-(2E,6E)-farnes-1-ol. These results represent a contribution to the chemotaxonomy of the genus Eriocoelum highlighting farnesol glycosides as chemotaxonomic markers of the subfamily of Sapindoideae in the family of Sapindaceae.

Oleanane-type glycosides from the roots of Weigela florida "rumba" and evaluation of their antibody recognition.

Three triterpene glycosides were isolated from the roots of Weigela florida "rumba" (Bunge) A. DC.: two previously undescribed 3-O-β-d-xylopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→4)]-β-d-xylopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyloleanolic acid (1) and 3-O-β-d-xylopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-xylopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid (2), and one isolated for the first time from a natural source 3-O-β-d-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyloleanolic acid (3).

Isolation and identification of new anthraquinones from Rhamnus alaternus L and evaluation of their free radical scavenging activity.

From the butanolic and the ethyl acetate extracts of Rhamnus alaternus L root bark and leaves, three new anthraquinone glycosides, alaternosides A-C (1,4,6,8 tetrahydroxy-3 methyl anthraquinone 1-O-ß-D-glucopyranosyl-4,6-di-O-α-L-rhamnopyranoside (1); 1,2,6,8 tetrahydroxy-3 methyl anthraquinone 8-O-ß-D-glucopyranoside (2) and 1, 6 dihydroxy-3 methyl 6 [2'-Me (heptoxy)] anthraquinone (3)) were isolated and elucidated together with the two known anthraquinone glycosides, Physcion-8-O-rutinoside (4) and emodin-6-O-α-L-rhamnoside (5) as well as with the known kaempferol-7-methylether (6), β-sitosterol (7) and β-sitosterol-3-O-glycoside (8). Their chemical structures were elucidated using spectroscopic methods (1D-, 2D-NMR and FAB-MS). Free radical scavenging activity of the isolated compounds was evaluated by their ability to scavenge DPPH free radicals.

New perspectives for natural triterpene glycosides as potential adjuvants.

Background: Triterpene glycosides are a vast group of secondary metabolites widely distributed in plants including a high number of biologically active compounds. The pharmacological potential is evaluated by using many bioassays particularly in the field of cancerology, immunology, and microbiology. The adjuvant concept is well known for these molecules in vaccines, but there is little preclinical evidence to support this concept in the management of cancer, infections and inflammation.

Triterpene saponins from Billia rosea.

Five previously undescribed triterpene saponins, billiosides A-E, and a known analogue, were isolated from the seeds of Billia rosea (Planch. & Linden) C. Ulloa & P.

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

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.

Triterpenoid saponins from the roots of Spergularia marginata.

Phytochemical investigations of the roots of Spergularia marginata had led to the isolation of four previously undescribed triterpenoid saponins, a known one and one spinasterol glycoside. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 3)-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester, 3-O-β-D-glucopyranosyl-(1 → 4)-3-O-sulfate-β-D-glucuronopyranosyl echinocystic acid 28-O-α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranosyl 21-O-acetyl acacic acid. Their cytotoxicity was evaluated against two human cancer cell lines SW480 and MCF-7.

New pregnane and phenolic glycosides from Solenostemma argel.

From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D - and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.