Crystalline structure of mangiferin, a C-glycosyl-substituted 9H-xanthen-9-one isolated from the stem bark of Mangifera indica

The crystalline structure of mangiferin (= 2-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one; 1), a biologically active xanthenone C-glycoside, isolated from the stem bark of Mangifera indica (Anacardiaceae), was unambiguously determined by single-crystal X-ray diffraction (XRD). The crystal structure is summarized as follows: triclinic, P1, a = 7.6575(5), b = 11.2094(8), c = 11.8749(8) angstrom, alpha = 79.967(5), beta = 87.988(4), gamma = 72.164(4)degrees, V = 955.3(1) angstrom(3), and Z = 2. The structure also shows two molecules in the asymmetric unit cell and five crystallization H2O molecules. The packing is stabilized by several intermolecular H-bonds involving either the two symmetry-independent mangiferin molecules 1a and 1b, or the H2O ones.

Effect of mangiferin on the development of periodontal disease: Involvement of lipoxin A(4), anti-chemotaxic action in leukocyte rolling

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

15种獐牙菜属植物中主要药用成分的高效液相色谱测定

对青藏高原和云贵高原的15种獐牙菜属植物进行了3种苦味苷,即獐牙菜苦苷(swertiamarin)、龙胆苦苷(gentiopicroside)、苦龙苷(amarogentin)、一种黄酮苷-当药黄素(swertisin)、及5种(口山) 山酮苷-芒果苷(mangiferin)、当药醇苷(swertianolin)、7-O-[α-L-吡喃鼠李糖-(1→2)-β-D-吡喃木糖]-1,8-二羟基-3-甲氧基(口山) 山酮(7-O-[α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl]-1,8-dihydroxy-3-methoxyxanthone)、7-O-β-D-吡喃木糖-1,8-二羟基-3-甲氧基(口山) 山酮(7-O-β-D-xylopyranosyl-l,8-dihydroxy-3-methoxyxanthone)、3-O-β-D-吡喃葡萄糖-1,8-二羟基-5-甲氧基(口山) 山酮(3-O-β-D-glucopyranosyl-1,8- dihydroxy-5-methoxyxanth-one)等9种主要药效成分同时进行了高效液相色谱的含量测定(Kromasil C18柱,甲醇-水梯度洗脱,二级管阵列检测);并对其主要药效成分的分布进行了比较。

Separation and determination of flavone and xanthone glycosides in Tibetan folk medicinal species Swertia mussotii and S-franchetiana by capillary electrophoresis

The contents of five pharmacologically active flavone and xanthone glycosides, namely, swertianolin, swertisin, isoorientin, mangiferin, and 7-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-1,8-dihydroxy-3-methoxyxanthone, extracted from Tibetan folk medicinal species Swertia mussotii and S. franchetiana were determined by capillary electrophoresis with diode-array detection. The separation of five components has been optimized with a capillary column with a total length of 48.5 cm and effective length of 40 cm (50 mu m i.d). The influence of the running buffer, the sodium dodecyl sulfonate (SDS) concentration, organic modifier, etc. on the resolution was evaluated. The background electrolyte contained 30 mM borate buffer, 28 mM SDS, 1.0% (v/v) acetonitrile, and was adjusted to pH 9.0 with 0.1 M NaOH. A good baseline resolution was obtained for the separation of five components within 5 min with the working voltage of 24 kV and a column temperature of 25 degrees C. The established method was rapid and reproducible for the separation and determination of five flavone and xanthone glycosides from the extracts of S. mussotii and franchetiana plant samples.

Separation and determination of the major active components in Tibetan folk medicinal species Swertia franchetiana by HPLC with DAD

A sensitive and specific reversed-phase high performance liquid chromatography (RP-HPLC) method with diode array detection (DAD) was established for the quantitative determination of the nine active components, namely, swertiamarin (SWM, 1), mangiferin (MA, 2), gentipicroside (GE, 3), sweroside (SWO, 4), isoorientin (IS, 5), swertisin (SWS, 6), swertianolin (SWN, 7), 7-O-[alpha-L-rhamnopyranosyl-1 -> 2)-beta-D-xylopyranosyl]-1,8-dihydroxy-3-methoxyxanthone (RX, 8), and bellidifolin (BE, 9) used as the external standard, in Tibetan folk medicinal species Swertia franchetiana. Based on the baseline chromatographic separation of most components from the methanolic extract of Swertia franchetiana on a reversed-phase Eclipse XDB-C8 column with water-acetonitrile-formic acid as mobile phase, the nine components were identified by comparison with standard samples and qualified by using the external standard method with DAD at 254 nm. The correlation coefficients of all the calibration curves were found to be higher than 0.9980. The relative standard deviations (RSDs) of the peak areas and retention times for the nine standards were less than 2.07% and 2.86%, respectively.

Variation of active constituents of an important Tibet folk medicine Swertia mussotii Franch. (Gentianaceae) between artificially cultivated and naturally distributed

Concentrations of seven phytochemical constituents (swertiamarin, mangiferin, swertisin, oleanolic acid, 1,5,8-trihydroxy-3methoxyxanthone, 1,8-dihydroxy-3,7-dimethoxyxanthone and 1,8-dihydroxy-3,5-dimethoxyxanthone) of "ZangYinChen" (Swertia mussotii, a herb used in Tibetan folk medicine) were determined and compared in plants collected from naturally distributed high-altitude populations and counterparts that had been artificially cultivated at low altitudes. Levels of mangiferin, the most abundant active compound in this herb, were significantly lower in cultivated samples and showed a negative correlation with altitude. The other constituents were neither positively nor negatively correlated with cultivation at low altitude. Concentrations of all of the constituents varied substantially with growth stage and were highest at the bud stage in the cultivars, but there were no distinct differences between flowering and fruiting stages in this respect. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

Lack of altitudinal trends in phytochemical constituents of Swertia franchetiana (Gentianaceae)

Diverse biological characters commonly vary with altitude in species that have a wide altitudinal distribution, partly at least as a result of adaptation to differences in aridity, but whether such variation exists for phytochemical constituents remains unknown. Therefore, levels of seven important phytochemical constituents of Swertia franchetiana (swertiamarin, oleanolic acid, swertisin, mangiferin, 1,5,8-trihydroxy-3-methoxyxanthone, 1,8-dihydroxy-3,7-dimethoxyxanthone and 1,8-dihydroxy-3,5-dimethoxyxanthone) were studied and statistically compared, using materials collected from sites ranging from 2200 to 3960 m in altitude. Swertiamarin was the most abundant in all samples, then mangiferin, oleanolic acid and the other three xanthones. Throughout the distributional range of this species, no altitudinal trend was detected for other constituents except 1,8-dihydroxy-3,7-dimethoxyxanthone, which showed a negative correlation with altitude. However, the concentration of 1, 8-dihydroxy-3,7-dimethoxyxanthone and mangiferin showed a significantly latitudinal and longitudinal correlation. (C) 2004 Elsevier Ltd. All rights reserved.

The mer-[RuCl(3)(dppb)(H(2)O)] complex: A versatile tool for synthesis of Ru(II) compounds

The complex mer-[RuCl(3)(dppb)(H(2)O)] [dppb = 1,4-bis(diphenylphosphino)butane] was used as a precursor in the synthesis of the complexes tc-[RuCl(2)(CO)(2)(dppb)], ct-[RuCl(2)(CO)(2)(dppb)]. cis-[RuCl(2)(dppb)(Cl-bipy)], [RuCl(2Ac4mT)(dppb)] (2Ac4mT = N(4)-meta-tolyl-2-acetylpyridine thiosemicarbazone ion) and trans-[RuCl(2)(dppb)(mang)] (mang = mangiferin or 1,3,6,7-tetrahydroxyxanthone-C2-beta-D-glucoside) complexes. For the synthesis of Run complexes, the Ru(III) atom in mer-[RuCl(3)(dppb)(H(2)O)] may be reduced by H(2)(g), forming the intermediate [Ru(2)Cl(4)(dppb)(2)], or by a ligand (such as H2Ac4mT or mangiferin). The X-ray structures of the cis-[RuCl(2)(dppb)(Cl-bipy)], tc-[RuCl(2)(CO)(2)(dppb)] and [RuCl(2Ac4mT)(dPpb)] complexes were determined. (C) 2010 Elsevier Ltd. All rights reserved.

Polyphenols with Antiulcerogenic Action from Aqueous Decoction of Mango Leaves (Mangifera indica L.)

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

Antiviral activities of plants occurring in the state of Minas Gerais, Brazil: Part 2. Screening Bignoniaceae species

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)

Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products

By determining the hydrogen peroxide (H2O2) released in cultures of peritoneal macrophage cells from Swiss mice, we evaluated the action of 27 vegetable compounds (pristimerin, tingenone, jatrophone, palustric acid, lupeol, cladrastin, ocoteine, boldine, tomatine, yohimbine, reserpine, escopoletin, esculine, plumericin, diosgenin, deoxyschizandrin, p-arbutin, mangiferin, and others) using a 2 mg/ml solution of each compound (100 mug/well). Macrophages are cells responsible for the development of the immunological response reaction, liberating more than one hundred compounds into the extracellular environment. Among these are the various cytokines and the intermediate compounds of nitrogen (NO) and oxygen (H2O2). This coordinated sequence of biochemical reactions is known as the oxidative burst. When we compared the results with those obtained with zymosan (an important stimulator of H2O2) we observed that the compounds showing the highest activity were substances 2 (tingenone), 16 (reserpine) and 20. Other substances such as compounds 1, 4, 5, 6, 8, 12, 13, 14, 15, 17, 19, 23, 24, 26, and 27 also showed a certain activity, but with less intensity than the aforementioned ones. Compounds 3, 7, 9, 10, 11, 18, 21, 22 and 25 presented no activity. These results suggest that natural products (mainly tingenone and reserpine and others) with different chemical structures are strong immunological modulators. However, further tests are needed to determine the 'oxidative burst' in future studies.

New antioxidant C-glucosylxanthones from the stems of Arrabidaea samydoides

Three new C-glucosylxanthones, 2-(2'-O-trans-caffeoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (1), 2-(2'-O-trans-cinnamoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (2), and 2-(2'-O-trans-coumaroyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (3), were isolated from the stems of Arrabidaea samydoides, in addition to three known C-glucosylxanthones, mangiferin (4), 2-(2'-O-benzoyl)-C-beta-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (5), and muraxanthone (6). Their chemical structures were assigned on the basis of MS and 1D and 2D NMR experiments. Xanthones 1-6 showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity evidenced by redox properties measured on ElCD-HPLC.

Avaliação da mangiferina na periodontite induzida em ratos

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Avaliação do potencial efeito cicatrizante gástrico e antiartrítico da mangiferina, uma xantona glicosilada da Mangifera indica

Rheumatoid arthritis (RA) is a chronic illness with great potential to cause comorbidities resulting from cumulative inflammatory activities, and it contributes with the increase of disabilities and death of patients. It affects 1 to 2% of world population and usually occurs between 30 and 50 years of age. Among existing therapeutic options for the disease non-steroidal anti-inflammatory drugs (NSAIDs) still play an important part in the treatment, being widely used by patients to relieve pain and stiffness. However, this class of drugs causes many adverse gastrointestinal effects, such as dyspepsia, heartburn, nausea and vomit, and its use is one of the most common causes of peptic ulcers. Mangiferin (a glicosilated xanthone extracted mainly from the bark of Mangifera indica L.) is the main compound of an aqueous extract made from the bark stem of the mango tree. Previous studies conducted by our research group prove the anti-inflammatory action of mangiferin on an animal model of periodontitis, and its gastroprotective action has been described before. Considering these informations this study evaluated mangiferin’s potential on the treatment of RA and on gastric ulcer healing in animal models, and analyzed toxicity parameters to assure efficacy and safety of the compound as potential new drug for the treatment of the disease. RA was induced in rats by subcutaneous injection of bovine collagen and Freund’s complete adjuvant. This method presented low incidence of RA in rats, but we were able to induce the disease in 60 to 70% of the animals. Due to the wide use of NSAIDs and its potential to cause peptic ulcers, we induced gastric ulcer on arthritic rats to analyze mangiferin’s gastric healing effect. After 14 days of treatment we noticed small increase of the lesion area of animals treated with mangiferin or ibuprofen, when compared to the animals... (Complete abstract click electronic access below)