Studies on the constituents of a Brazilian folk infusion. Isolation and structure elucidation of new triterpene saponins from Ilex amara leaves

The isolation of three new triterpene saponins 3beta-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-2-O-acetylara-binopyranosylolean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl ester (2), 3beta-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-O-arabinopyranosylurs-12-en-28-oic acid (3), and 3beta-O-beta-D-glucopyranosyl-(1-->2)-beta-D-O-galactopyranosylurs-12-en-28-oic acid (4) together with five known saponins and one flavonoid glycoside from the aqueous infusion of flex amara (Vellozo) Loes. leaves is reported. All structures were elucidated by spectroscopic methods, including the concerted application of one-dimensional (H-1, TOCSY, C-13, and C-13 DEPT NMR) and two-dimensional NMR techniques (DQF-COSY, HSQC, and HMBC).

Estudo químico de chás brasileiros

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Triterpenes and saponins from Rudgea viburnioides

A novel triterpene; viburgenin (1), has been isolated from an extract of the ripe fruit rinds of Rudgea viburnioides, together with the known saponins, arjunglucoside I and trachelosperosides B-1 and E-l, and the triterpenes trachelosperogenin B (2) and arjungenin. Compound 2 was previously obtained as a product from enzymatic hydrolysis, and it is reported for the first time as a natural product. The structure of compound 1 was determined as 2α,3β,19α,23,24-pentahydroxyurs-12-ene by extensive use of 1D and 2D NMR spectroscopic methods. Compound 1 exhibited moderate antifungal activity against Cladosporium cladosporioides.

Triterpene benzoates from the bark of Picramnia teapensis (Simaroubaceae)

Two new benzoic acid esters of triterpene alcohols [lup-20 (29)-en-28-oic acid 3 alpha, 7 beta -dibenzoate and 3 alpha -hydroxy-lup-20(29)-en-28-ic acid 7 beta -benzoate] were isolated from the stem bark of Picramnia teapensis Tul. The structures of these compounds were established on the basis of spectral analyses. Other known compounds, beta -sitosterol, estigmasterol, lupeol and epilupeol, were identified in mixture by GC-MS. The triterpene esters have not shown in-vitro inhibitory effect on the growth of Leucoagaricus gongylophorus (Fisher), referred also as Leucocoprinus gongylophorus (Heim), syn Rozites gongylophora (Moller), the symbiotic fungus cultivated by the leaf-cutting ant Atta sexdens L.

Use of Saponins as an Effective Surface Modifier in Cellulose Nanocomposites

The present paper deals with the extraction of saponins from the pericarp of Sapindus mukorossi to use as compatibilizer in nanocomposites. The nanofibrils extracted from banana fibres are utilized as reinforcement of nanocomposite. These nanofibers were treated with Saponin, GPS (3-Glycidoxypropyltrimethoxysilane) and APS (3-Aminopropyltriethoxysilane) to compare the effectiveness of surface treatment. The effectiveness of surface modification was reflected on the increase in mechanical (tensile test, flexural modulus, impact test) properties and decrease in the RMS (Roughness Measurement System) roughness investigation by SFM (Scanning force microscopy) analysis.

Oleanane Saponins and Glycerogalactolipids from the Leaves of Guapira graciliflora

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Preparative droplet counter-current chromatography for the separation of the new nor-seco-triterpene and pentacyclic triterpenoids from Qualea parviflora

The methanolic extract of the bark of the medicinal plant Qualea parviflora (Vochysiaceae) contains new nor-seco-triterpene and pentacyclic triterpenoids. They were separated in a preparative scale using droplet counter-current chromatography. The optimum solvent used was composed of a mixture of CHCl3/MeOH/H2O (43:37:20, v/v) in the descending mode and led to a successful separation of the new compound 28-nor-17, 22-seco-2 alpha, 3 beta, 19, 22, 23-pentahydroxy-Delta(12)-olecinane, besides the known triterpenoids bellericagenin B, bellericaside B and arjunglucoside I. Identification was performed by ESI-MS, H-1 NMR and C-13 NMR analyses.

Complete Assignments of ¹H and 13C-NMR Spectra of the 3,4-seco-Triterpene Canaric Acid isolated from Rudgea jasminoides

O ácido canárico 1 foi isolado das folhas de Rudgea jasminoides. A substância isolada é um derivado triterpênico do tipo seco-lupano e teve sua estrutura elucidada com base nos dados espectrais, principalmente em experimentos de RMN a 1D e 2D. O sitosterol, o estigmasterol e os ácidos ursólico e oleanólico também foram isolados.

Saponins, IL12 and BCG adjuvant in the FML-vaccine formulation against murine visceral leishmaniasis

The FML antigen of Leishmania donovani, in combination with either Riedel de Haen (R), QuilA, QS21 saponins, IL12 or BCG, was used in vaccination of an outbred murine model against visceral leishmaniasis (VL). Significant and specific increases in anti-FML IgG and IgM responses were detected for all adjuvants, and in anti-FML IgG1, IgG2a and IgG2b and delayed type of hypersensitivity to L. donovani lysate (DTH), only for all saponins and IL12. The QS21-FML and QuilA-FML groups achieved the highest IgG2a response. QuilA-FML developed the strongest DTH and QS21-FML animals showed the highest serum IFN-gamma concentrations. The reduction of parasitic load in the liver in response to each FML-vaccine formulation was: 52% (P < 0.025) for BCG-FML, 73% (P < 0.005) for R-FML, 93% (P < 0.005) for QuilA-FML and 79.2% (P < 0.025) for QS21-FML treated animals, respectively. Protection was specific for R-FML and QS21-FML while the QuilA saponin treatment itself induced 69% of LDU reduction. The FML-saponin vaccines promote significant, specific and strong protective effects against murine visceral leishmaniasis. BCG-FML induced minor and non-specific protection while IL 12-FML, although enhancing the specific antibody and IDR response, failed to reduce the parasitic load of infected animals. (C) 2002 Elsevier B.V. Ltd. All rights reserved.

Hepatogenous photosensitization of ruminants by Brachiaria decumbens and Panicum dichotomiflorum in the absence of sporidesmin: Lithogenic saponins may be responsible

As part of a study of plants involved in crystal-associated hepatogenous photosensitization diseases, samples of Brachiaria decumbens and Panicum dichotomiflorum on which cattle and goats had recently been photosensitized were analyzed. The level of saponins associated with these photosensitization outbreaks were determined by GC-MS. Only low levels of Pithomyces chartarum spores were present on the B decumbens, and all isolates obtained failed to produce sporidesmin.

Pharmacognostical evaluation of fruits of Solanum lycocarpum A. St.-Hill. (Solanaceae)

This study describes the chemical and physical-chemical profile of plant drug and ethanolic extract obtained from fruits of Solanum lycocarpum A. St.-Hill. (Solanaceae). The physical and chemical analysis involved the granulometry determination, non-compacted apparent density, loss on drying in oven and in infrared scale, pH, ash values and extractive values. The results determined the physical-chemical characteristics of the drug plant. It was also carried out the microbiological control of the plant drug. The preliminary phytochemical screening featured the presence of tannins, flavonoids and saponins in the plant drug and alkaloids and steroids in the ethanolic exctract. The solamargine and solasonine glycoalkaloids were identified through TLC and GC/ MS. The levels of total phenols and tannins were quantified in the extract (8.90% and 6,85% respectively). Such studies contribute to the chemical identification and quality control of S. lycocarpum fruits. © 2010 Phcog.net.

Production of the Quinone-Methide Triterpene Maytenin by In Vitro Adventitious Roots of Peritassa campestris (Cambess.) ACSm. (Celastraceae) and Rapid Detection and Identification by APCI-IT-MS/MS

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

New steroidal saponins and antiulcer activity from Solanum paniculatum L.

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)