Chemical constituents from Sidastrum paniculatum and evaluation of their leishmanicidal activity

Teles, Yanna Carolina Ferreira; Chaves, Otemberg Souza; Agra, Maria de Fátima; Batista, Leônia Maria; Queiroz, Aline Cavalcanti de; Araújo, Morgana Vital de; Alexandre-Moreira, Magna Suzana; Braz-Filho, Raimundo; Souza, María de Fátima Vanderlei de

doi:10.1016/j.bjp.2015.02.002

Cited by 14 publications

(8 citation statements)

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“…Thus, we hypothesized that BSG would be an effective candidate to stimulate ceramide synthesis in the epidermis via the activation of an estrogen signaling cascade that may be associated with the enhanced gene expression of sphingolipid metabolizing enzymes. BSG is a phytosterol glycoside that is found in various plants [ 26 – 29 ] and has also been reported to exhibit several bioactivities such as anti-diabetic [ 30 ], anti-tumor [ 31 , 32 ] and analgesic [ 33 ] effects.…”

Section: Introductionmentioning

confidence: 99%

β-Sitosterol 3-O-D-glucoside increases ceramide levels in the stratum corneum via the up-regulated expression of ceramide synthase-3 and glucosylceramide synthase in a reconstructed human epidermal keratinization model

et al. 2021

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β-Sitosterol 3-O-d-glucoside (BSG) is known to act as an agonist by binding to estrogen receptors, and estrogen has been reported to enhance the activity of β-glucocerebrosidase, an epidermal ceramide metabolizing enzyme. In this study, we determined whether BSG up-regulates ceramide levels in the stratum corneum (SC) of a reconstructed human epidermal keratinization (RHEK) model. Treatment with BSG significantly increased the total ceramide content by 1.2-fold compared to that in the control in the SC of the RHEK model, accompanied by a significant increase of the ceramide species, Cer[EOS] by 2.1-fold compared to that in the control. RT-PCR analysis demonstrated that BSG significantly up-regulated the mRNA expression levels of serine palmitoyltransferase (SPT)2, ceramide synthase (CerS)3, glucosylceramide synthase (GCS) and acid sphingomyelinase by 1.41–1.89, 1.35–1.44, 1.19 and 2.06-fold, respectively, compared to that in the control in the RHEK model. Meanwhile, BSG significantly down-regulated the mRNA expression levels of sphingomyelin synthase (SMS)2 by 0.87–0.89-fold. RT-PCR analysis also demonstrated that BSG significantly up-regulated the mRNA expression levels of CerS3 and GCS by 1.19–1.55 and 1.20-fold, respectively, but not of SPT2 and significantly down-regulated that of SMS2 by 0.74-fold in HaCaT keratinocytes. Western blotting analysis revealed that BSG significantly increased the protein expression levels of CerS3 and GCS by 1.78 and 1.28–1.32-fold, respectively, compared to that in the control in HaCaT cells. These findings indicate that BSG stimulates ceramide synthesis via the up-regulated expression levels of CerS3 and GCS in the glucosylceramide pathway, which results in a significantly increased level of total ceramides in the SC accompanied by significantly increased levels of acylceramide species such as Cer[EOS].

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Section: Introductionmentioning

confidence: 99%

β-Sitosterol 3-O-D-glucoside increases ceramide levels in the stratum corneum via the up-regulated expression of ceramide synthase-3 and glucosylceramide synthase in a reconstructed human epidermal keratinization model

et al. 2021

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“…The chromatographic fractionation of the methanolic extract of this species afforded sitosterol-3- O - β - d -glucoside ( 2 ) and stigmasterol-3- O - β - d -glucoside ( 3 ) as an inseparable mixture (with a ratio of 1:1), and the new compound 1 . The chemical structure of compounds 2 and 3 was determined based on spectral analysis and comparisons with relevant literature [ 6 ]. These compounds were also found in other Lagochilus species viz.…”

Section: Resultsmentioning

confidence: 99%

“…L. inebrians and L. gypsaceus [7]. Further investigations of the methanolic extract of L. setulosus afforded pinitol (4) and an inseparable mixture (with a ratio of 1.2:1) of 6β-hydroxyl-7-epi-loganin (5) and chlorotuberoside (6). Most recently, the iridoid glycoside 5 has been reported from several species of Eremostachys [8,9] and Picconia excelsa [10].…”

Section: Chemical Composition Of L Setulosusmentioning

confidence: 99%

Sugar Containing Compounds and Biological Activities of Lagochilus setulosus

et al. 2021

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Phytochemical investigation of the methanolic extract obtained from the aerial parts of Lagochilus setulosus (Lamiaceae) afforded the new compound 1-methoxy-3-O-β-glucopyranosyl-α-l-oliose (1) together with five known glycosides, namely sitosterol-3-O-β-glucoside (2), stigmasterol-3-O-β-glucoside (3), pinitol (4), 6β-hydroxyl-7-epi-loganin (5), and chlorotuberoside (6). The structures of these compounds were elucidated by extensive spectroscopic analyses, especially HR-MS, 1D and 2D NMR spectroscopy. The in vitro cytotoxic activity of the methanolic extract and the isolated compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and crystal violet (CV) staining assays. In addition, the antifungal activities of the components were evaluated against Botrytis cinerea, Septoria tritici, and Phytophthora infestans. The anthelmintic potential was determined against Caenorhabditis elegans nematodes. Neither the extract nor the isolated compounds showed promising activity in all the bioassays.

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“…Steroids are widespread in plants and play an important role as components of vegetable cell walls and membranes. They have been previously been reported in many Malvaceae species, such as Sidastrum paniculatum, Wissadula periplocifolia, Sida rhombifolia, Sida galheirensis, Bakeridesia pickelli, and Herissantia crispa (Teles et al, 2015;Chaves et al, 2013;Silva et al, 2006;Costa et al, 2007;Costa et al, 2009 (Farruque et al, 2003). Triterpenes have been reported in Malvaceae species, and hopane triterpenes have recently been reported in Wissadula periplocifolia and Sidastrum paniculatum Teles et al, 2015).…”

Section: Structural Elucidation Of the Isolated Compoundsmentioning

confidence: 97%

“…Previous phytochemical studies of Sidastrum have reported the presence of steroids, triterpenes, and phenolic compounds (Cavalcante et al, 2010;Teles et al, 2015). We previously reported the isolation from S. micranthum of tiliroside, 4'-methoxy-5,7-dihydroxyflavone (acacetin), and 7,4′-di-O-methylisoscutellarein, as well as other phenolic compounds (Gomes et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Phytoconstituents from Sidastrum micranthum (A. St.-Hil.) Fryxell (Malvaceae) and antimicrobial activity of pheophytin a

Gomes

Teles

Pereira

et al. 2015

Braz. J. Pharm. Sci.

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Sidastrum micranthum (A. St.-Hil.) Fryxell, a member of the Malvaceae family, is called malva preta in Brazil. As this species is commonly used to treat bronchitis, cough, and asthma, better knowledge of its chemical compounds is important. The phytochemical study of its hexane extract, using chromatographic techniques, led to isolation of six compounds: the triterpene isoarborinol, a mixture of sitosterol and stigmasterol, sitosterol-3-O-β-D-glucopyranoside, pheophytin a, and 132-hydroxy-(132-S)-pheophytin a. Structural identification of these compounds was carried out using spectroscopic methods such as IR and 1D and 2D NMR (HOMOCOSY, HMQC, HMBC, and NOESY). Compounds isolated from S. micranthum were screened for their in vitro antifungal and antibacterial activity against twenty fungal and bacterial standard strains. Pheophytin a exhibited antimicrobial action against all microorganisms tested.

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Chemical constituents from Sidastrum paniculatum and evaluation of their leishmanicidal activity

Cited by 14 publications

References 53 publications

β-Sitosterol 3-O-D-glucoside increases ceramide levels in the stratum corneum via the up-regulated expression of ceramide synthase-3 and glucosylceramide synthase in a reconstructed human epidermal keratinization model

β-Sitosterol 3-O-D-glucoside increases ceramide levels in the stratum corneum via the up-regulated expression of ceramide synthase-3 and glucosylceramide synthase in a reconstructed human epidermal keratinization model

Sugar Containing Compounds and Biological Activities of Lagochilus setulosus

Phytoconstituents from Sidastrum micranthum (A. St.-Hil.) Fryxell (Malvaceae) and antimicrobial activity of pheophytin a

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