Triterpene glycosides from plants for antibody recognition

Effects of the flavonoids extracted from Spergularia purpurea Pers. on arterial blood pressure and renal function in normal and hypertensive rats

The antihypertensive and diuretic effects of the flavonoids extracted from Spergularia purpurea Pers. (SP) were studied both in normotensive (NTR) and spontaneously hypertensive conscious rats (SHR). Daily oral administration of the flavonoid mixture (5 mg/kg for 1 week) exhibited a significant decrease in blood pressure with variation coefficient (Delta) of 20 in SHR rats and 11 in NTR rats. The systolic and diastolic blood pressure decreased significantly and respectively with 17 and 24% in SHR, and with 11 and 16% in NTR. The flavonoid mixture enhanced significantly the water excretion in hypertensive (P<0.001) and normal rats (P<0.001). Furthermore, oral administration of flavonoids mix…

Secondary metabolites from polar fractions of Piper umbellatum.

Seven known secondary metabolites were isolated from the methanol extract of the branches of Piper umbellatum. The identification of these compounds was mainly achieved by 2D NMR spectroscopic techniques and FAB-MS. Among them, the known cepharadiones A and B can be considered as chemotaxonomic markers of the genus Piper.

New terpenoid glycosides from Eriocoelum microspermum

New ursolic and betulinic derivatives as potential cytotoxic agents.

Fifteen new ursolic and betulinic triterpenoids, bearing various functionalities at C-3 and C-28 were synthesized as potential cytotoxic agents. All compounds were obtained by a hemisynthetic route via ursolic and betulinic acids. Preliminary screening of these compounds on human HT 29 colon cancer cells revealed inhibitory activity for three of them. Beta-D-Glucopyranosyl-3beta-hydroxyurs-12(13)-en-28-oate 1c, 3beta-3-(3-pyridyl)-prop-2-enoyloxyurs-12(13)-en-28-oic acid 1i and the potassium salt of 3beta-cinnamoyloxylup-20(29)-en-28-oic acid 2d demonstrated cytotoxic activity in the micromolar range: 8.0, 45.0 and 8.0 microM, respectively.

Triterpene Saponins from the Fruits of Phytolacca rugosa (Phytolaccaceae)

Four known serjanic acid glycosides were isolated from the fruits of Phytolacca rugosa and characterized mainly by 2D NMR spectroscopy and mass spectrometry. This aglycon has a chemotaxonomic significance for the genus Phytolacca.

Characterization of the biosynthesis of saponins during seed development in peas (Pisum sativum)

National audience; 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 which can impart a bitter taste to the final food product. Bitter flavours are currently either removed by energy-requiring physico-chemical treatments or masked by additives. We are in the process of identifying and characterizing the genes involved in saponin biosynthesis during pea seed development, with the objective of identifying mutants in which seed saponins no longer accumulate. To do this we have applied a saponin extraction protoco…

Triterpene Saponins from the Roots of Achyranthes bidentata

Three saponins, oleanolic acid-28- O -s-D-glucopyranoside (1), chikusetsusaponin V (2), and 3- O -s-D-glucopyranosyl-oleanolic acid-28- O -s-D-glucopyranoside (3) were isolated from the roots of Achyranthes bidentata Blume (Amaranthaceae). No activity was shown in the granulocyte phagocytosis test nor in the test of the potentiation of the cytotoxicity of cisplatin in human colon cancer cells. This is the first report of compounds 1, 2 and 3 isolated from Achyranthes species. Furthermore, the NMR data of 2 completed the partially published data.

Grain legumes for human consumption: management of off-flavours

International audience

Antinociceptive Effects of Turkish Endemic Eryngium kotschyi Boiss. Roots by Bioactivity Guided Fractionation

Eryngium species (Apiaceae) are well known plants in ethnobotanical culture throughout world and also in Turkey. They are used as antitussive, diuretic as well as for analgesic and antiinflammatory purposes in traditional medicine. This study aimed to evaluate the antinociceptive activity of endemic Eryngium kotschyi Boiss. root extracts by bioguided fractionation. The antinociceptive activity of the extracts/fractions/compound was studied in mice using acetic acid induced writhing test and and hot plate test. The methanolic extract was sequentially partitioned with hexane, dichloromethane and water saturated n-butanol. Among the fractions, the n-BuOH fraction showed the most significant re…

Antioxidant effect of Ajuga iva aqueous extract in streptozotocin-induced diabetic rats.

The purpose of this study was to investigate the possible antioxidant effect of an aqueous extract of Ajuga iva (Ai) in streptozotocin (STZ)-induced diabetic rats. Twelve diabetic rats were divided into two groups fed a casein diet supplemented or not with Ai (0.5%), for 4 weeks. In vitro, the Ai extract possessed a very high antioxidant effect (1 mg/ml was similar to those of trolox 300 mmol/l). The results indicated that plasma thiobarbituric acid reactive substances (TBARS) values were reduced by 41% in Ai-treated compared with untreated diabetic rats. TBARS concentrations were lower 1.5-fold in liver, 1.8-fold in heart, 1.9-fold in muscle and 2.1-fold in brain in Ai-treated than untreat…

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 a…

Steroidal saponins and flavan-3-ol glycosides from Dioscorea villosa

New Steroidal Alkaloids from Solanum Hypomalacophyllum

Two new steroidal alkaloids (1-2) have been isolated from the leaves and roots of Solanum hypomalacophyllum Bitter, respectively. Their structures have been elucidated as deacetoxysolaphyllidine-3- O-β-D-glucopyranoside (1) and 4-keto-5,6-dihydro-(20 S)-verazine (2). Furthermore, two known steroidal alkaloids, 20 R-verazine and 20 S-verazine, and the common secondary metabolites oleanolic acid and β-sitosterol were isolated from the roots, whereas deacetoxysolaphyllidine was obtained from the leaves.

Effect of an aqueous extract of Ajuga iva on glycaemia, reverse cholesterol transport and atherogenic ratios in rats with streptozotocin-induced diabetes

ChemInform Abstract: Two Triterpene Saponins from Achyranthes bidentata.

Bidentatoside II (1) and chikusetsusaponin V methyl ester (2) are two further triterpene saponins isolated from the roots of Achyranthes bidentata. Chemical and homo and heteronuclear two-dimensional (2D) NMR techniques have led to the structural elucidation of 1 which is a new seco-glycoside of oleanolic acid and the full 1H- and 13C-NMR assignments of 2. These compounds did not show any potentiation of the in vitro cytotoxicity of cisplatin in the HT 29 human colon cancer cell line.

ChemInform Abstract: Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetana Pom.

A new sesquiterpene ester, tunetanin A (1), a new sesquiterpene coumarin, tunetacoumarin A (2), together with eight known compounds, i.e., coladin (3), coladonin (4), isosmarcandin (5), 13-hydroxyfeselol (6), umbelliprenin (7) propiophenone (8), beta-sitosterol (9), and stigmasterol (10), were isolated from the roots of Ferula tunetana. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D- and 2D-NMR experiments and MS analysis, as well as by comparison with published data. The cytotoxicity of compounds 1-7 towards two human colon cancer cell lines, HT-29 and HCT 116, was evaluated. Compounds 3, 4, and 6 showed weak cytotoxic activities.

Bioactive saponins from plants: An update

Plant saponins are a group of naturally occuring triterpene or steroid glycosides which include a large number of biologically and pharmacologically active compounds. Saponins have been shown in both in vitroand in vivoexperimental test systems during the last decade to possess a broad spectrum of biological and pharmacological activities. This review will summarize some of the recent advances concerning cancer-related activity, immunostimulating, immunoadjuvant, antihepatotoxic, antiphlogistic, antiallergic, molluscicidal, hemolytic, antifungal, antiviral, and hypoglycemic activities. In addition, the effects on the cardiovascular system and the central nervous system will be discussed tog…

Effect of aqueous extract of Ajuga iva supplementation on plasma lipid profile and tissue antioxidant status in rats fed a high-cholesterol diet

Abstract The present study was designed to explore the possible antioxidant and hypolipidemic effects of the aqueous extract of Ajuga iva (0.5% in the diet) in rats fed a high-cholesterol (1%) diet (HCD). The results indicated that the HCD-Ai versus HCD treatment led to many changes in biochemical parameters. They showed a decrease of plasma total cholesterol (TC) and VLDL-cholesterol but an increase of HDL2-cholesterol. The triacylglycerol contents were reduced in plasma and in VLDL. The lipid peroxidation determined by TBARS was decreased by 75% in plasma. TBARS in liver, heart and kidneys were highly reduced excepted in the adipose tissue. Ajuga iva treatment enhanced superoxide dismutas…

Steroidal Saponins from the Fruits of Cestrum ruizteranianum

Seven spirostane and furostane-type glycosides were isolated from the aqueous methanolic extract of the fruits of Cestrum ruizteranianum and characterized mainly by 2D NMR spectroscopy and mass spectrometry. These known saponins belong to the Δ5-spirostene and Δ5-furostene series and are reported in this species for the first time.

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

Abstract 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. The mutations studied are located in a gene designated PsBAS1 (β-amyrin s…

ChemInform Abstract: Two New Retigerane-Type Sesterterpenoids from the Lichen Leprocaulon microscopicum.

Two new compounds (I) and (II) are isolated, possessing a rare pentacyclic carbon skeleton typical for lichen metabolism, and quite unusual in the vegetal kingdom.

Constituents isolated from Polyscias fulva

Dracoside, a New Steroidal Saponin fromHelleborus purpurascens

Abstract A new steroidal saponin, 1-O-[6-O-acetyl-β-D-galactopyranosyl]-24-O-[β-D-apiofuranosyl-(1→3)-4-O-acetyl-α-L-rhamnopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-arabinopyranosyl]-dracogenin, was isolated from the roots of Helleborus purpurascens and named dracoside. Structure elucidation was performed by chemical transformations and various spectroscopic methods, mainly 2D NMR techniques (COSY, HMQC, HMBC).

A new ecdysteroid and other constituents from two Dioscorea species

Phytochemical investigation of the rhizome of Dioscorea dumetorum has led to the isolation by several chromatographic steps on normal and reversed phase silica gel of a new ecdysteroid, (20R)-5β,11α,20-trihydroxyecdysone (1), and two known ecdysteroids, ajugasterone C (2) and herkesterone (3). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR (COSY, TOCSY, HSQC and HMBC). This is the first report on the occurrence of phytoecdysteroids in the Dioscoreaceae family. These compounds were devoid of antifungal activity against three Candida species (Candida albicans, Candida glabrata and Candida tropicalis, MIC > 200 μg/ml).

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

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.

Supporting information - Supplemental material for Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana

Supplemental material, Supporting information for Triterpenoid Saponins From the Stem Bark of Pentaclethra eetveldeana by David Pertuit, Mpuza Kapundu, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Clément Delaude, and Marie-Aleth Lacaille-Dubois in Natural Product Communications

Cytotoxic glycosides from the roots of Weigela x “Bristol Ruby”

International audience; 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.

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. Their structures were established on the basis of 1D and 2D NMR data, mass spectrometry and chemical methods. Compounds 2 and 4 exhibited weak …

Antinociceptive and anti-inflammatory activities of Acacia pennata wild (Mimosaceae)

The butanolic fraction of dried leaves of Acacia pennata (Mimosaceae) was tested for analgesic and anti-inflammatory activities in animal models. It showed significant protective effects against chemical stimuli (acetic acid and formalin) in the mouse. It also produced a significant increase of the threshold of sensitivity to pressure-induced pain in the rats. The extract revealed an inhibitory effect in carrageenin-induced rat paw oedema in the late phase. The results suggested that a peripheral mechanism is involved in the analgesic, associated to anti-inflammatory effect (NSAIDs-like). Among the class of compounds characterized in this fraction, flavonoids may be mainly responsible for t…

Changes in antioxidant defense status in hypercholesterolemic rats treated with Ajuga iva.

Abstract The aim of the study was to investigate the effect of aqueous extract of Ajuga iva ( Ai ) on serum and tissues lipid peroxidation as well as antioxidant enzymes activities in red blood cells (RBC) and tissues, in high hypercholesterolemic rats (HC). Male Wistar rats ( n =12) were fed on 1% cholesterol-enriched diet for 15 d. After this adaptation phase, hypercholesterolemic rats (total cholesterol=6.5±0.6 mol/l) were divided into two groups fed the same diet and treated or not with Ai for 15 d. Thiobarbituric acid reactive substances (TBARS) concentrations in serum, LDL-HDL 1 , HDL 2 and HDL 3 were respectively, 5-, 7.8-, 2.3- and 5-fold lower in Ai treated than untreated hyperchol…

A review of the biological and pharmacological activities of saponins.

Summary This paper reviews the important biological and pharmacological activities of saponins reported over the last few years. These include cancer-related activity, as well as antiphlogistic and antiallergic, immunomodulating, antihepatotoxic, antiviral, hypoglycemic, antifungal and molluscicidal activities. The action of saponins on the cardiovascular, central nervous, and endocrine systems and other miscellaneous effects are also discussed.

Portulaca oleracea reduces triglyceridemia, cholesterolemia, and improves lecithin: cholesterol acyltransferase activity in rats fed enriched-cholesterol diet.

Abstract Purpose The effects of Portulaca oleracea ( Po ) lyophilized aqueous extract were determined on the serum high-density lipoproteins (HDL 2 and HDL 3 ) amounts and composition, as well as on lecithin: cholesterol acyltansferase (LCAT) activity. Methods Male Wistar rats ( n  = 12) were fed on 1% cholesterol-enriched diet for 10 days. After this phase, hypercholesterolemic rats (HC) were divided into two groups fed the same diet supplemented or not with Portulaca oleracea ( Po -HC) (0.5%) for four weeks. Results Serum total cholesterol (TC) and triacylglycerols (TG), and liver TG values were respectively 1.6-, 1.8-, and 1.6-fold lower in Po -HC than in HC group. Cholesterol concentrat…

Beneficial effects of a methanolic extract of Globularia alypum on glycaemia, lipid peroxidation and antioxidant enzymes activities in rats with streptozotocin-induced diabetes

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

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. After successive purifications by various chromatographic methods, like solid/liquid chromatographic methods, vacuum liquid chromatography (VLC), medium pressure liquid chromatography (MPLC), on normal and reverse phase (RP-18 silica gel), and size exclusion chromatography on Sephadex L, their structures were elucidated by an extensive 600 MHz NMR analysis including 1D and 2D NMR experiments as well as ESI-MS. Among the seven isolated saponins, two have never been reported before : 3…

Oleanane-type saponins from the roots of Wisteria floribunda macrobotrys

Hypoglycaemic effect of Spergularia purpurea in normal and streptozotocin-induced diabetic rats

Single and repeated oral administration of the water extracts of Spergularia purpurea (SP) at a dose of 10 mg/kg were tested on hypoglycaemic activity in normal and streptozotocin-induced diabetic rats. In normal rats, the water extract of SP decreased significantly the plasma glucose levels 4 h after single oral administration (P0.01), and one week after repeated oral administration (P0.05). A significant decrease of plasma glucose levels was observed 6 h after a single oral administration of the water extract of S. purpurea in severe hyperglycaemic rats (n=6) from 22.78+/-0.60 to 11.21+/-0.49 mmol/l (P0.001). On other hand, water extract of S. purpurea normalised plasma glucose levels aft…

A review on the phytopharmacological studies of the genus Polygala

Abstract 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. Mat…

Saponins as immunoadjuvants and immunostimulants

Saponins are either triterpene or steroid glycosides widely distributed in the plant and animal kingdom and include a large number of biologically active compounds. Most of them have surface-active and cholesterol-binding properties.

Chemical constituents from Phlomis bovei Noë and their chemotaxonomic significance

Abstract A phytochemical investigation of the leaves and roots of Phlomis bovei Noe (Lamiaceae) led to the isolation of sixteen compounds, including iridoids (1, 2, 3), megastigmanes (4, 5), phenylpropanoids (6, 7, 8, 9, 10), lignans (11, 12, 13, 14), a nortriterpene (15), and a phenyl glucoside (16). Compounds (1, 2, 4, 5, 6, 10) were obtained from the leaves and compounds (1, 2, 3, 7, 8, 9, 11, 12, 13, 14, 15, 16) were isolated from the roots. Compounds 1 and 2 were found both in the leaves and in roots. The compounds were identified by analysis of 1D- (1H, 13C), 2D-NMR (1H–1H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data, mass spectrometry (ESI- and HR-ESI-MS), and by comparison wit…

A dammarane-type saponin from the roots of Ampelozizyphus amazonicus.

A new C31 dammarane-type triterpenoid saponin has been isolated from the roots of Ampelozizyphus amazonicus. Its structure was elucidated to be ampelozigenin-15 alpha-O-acetyl- 3-O-alpha-L-rhamnopyranosyl-(1--2)-beta-D-glucopyranoside by 1D and 2D NMR spectroscopic methods, and by chemical transformations. Ampelozigenin is a novel triterpene, (20R,22R)-16 beta,22:16 alpha, 30-diepoxydammar-24(24')- methylene-3 beta, 15 alpha, 20-triol.

Triterpenoid saponins from the cultivar “Green Elf” of Pittosporum tenuifolium

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-glucopyra…

Induction of Neuronal Differentiation in Neurosphere Stem Cells by Ellagic Acid Derivatives

A bioassay-guided fractionation of methanol extracts of stem barks, combined with screening based on Epidermal Growth Factor (EGF)-responsive neural stem cells (erNSCs) differentiation assay, has been used. This study resulted in the isolation of 3,3′-di- O-methylellagic acid 1, 3,3′-di- O-methyl ellagic acid-4- O-β-D-xylopyranoside 2, ellagic acid 3, and arjunolic acid 4. Among them, compounds 1 and 2 exhibit potent induction of neuronal differentiation in neurosphere stem cells with no cytotoxic effect. These results indicate that compounds 1 and 2 may be useful as pharmacological agents for the treatment of neurodegenerative diseases. These compounds may account, for the use of T. super…

Glycoside derivatives of scopoletin and β-sitosterol from Hymenodictyon floribundum

La génétique au service du goût : caractérisation de mutants pour l'accumulation de saponines et l'activité lipoxygènase dans la graines de pois (Pisum sativum)

International audience

Secoiridoids and Xanthones fromGentianella nitida

From Gentianella nitida twelve known metabolites were isolated and identified by HPLC-UV and/or by spectroscopic methods as secologanoside, amaroswerin, amarogentin (secoiridoids), isoorientin (C-glucosylflavone), mangiferin, demethylbellidifolin 8-O-glucoside, norswertianine 1-O-glucoside, swertianine 1-O-primeveroside, swertianine 8-O-glucoside, norswertianine, demethylbellidifolin, and swertianine (xanthone glycosides and aglycones). Secologanoside is reported here for the first time in Gentianaceae species ; the antioxidant mangiferin was obtained as the major compound in good yield.

Natural Triterpene Glycosides for Antibody Recognition

Multiple sclerosis is an autoimmune disease that affects the central nervous system. The key role of the glycosylation in disease pathogenesis has been previously studied and the synthetic N-glucosylated peptide CSF114(Glc) proved its efficiency in autoantibody recognition in the sera of multiple sclerosis patients. Herein, pure natural triterpene glycosides containing different glycosyl moieties were isolated and tested in multiple sclerosis patientsʼ sera to better understand the role of glycosylation. They were selected taking into account the nature and complexity of their osidic part. Five triterpene glycosides were isolated from several plants with more than 95 % purity. The interacti…

Two New Oleanane-type Saponins from Hydrocotyle multifida

A phytochemical study of a Venezuelan species Hydrocotyle multifida led to the isolation of five oleanane-type glycosides: two previously undescribed and three known ones. 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-glucuronopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyrano-syloleanolic acid. These results represent a significative contribution to the chemotaxonomy of the Hydrocotyle genus.