Pallidol, a resveratrol dimer from Cissus pallida

Khan, Mohammad Zafar; Nabi, Shah G.; Prakash, Suraj; Zaman, Asif

doi:10.1016/s0031-9422(00)81180-2

Cited by 87 publications

(52 citation statements)

References 13 publications

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“…Ac 2 O (0.83 ml) and Et 3 N (1.23 ml) were then added and the reaction mixture kept at ambient temperature for 24 h. The reaction was then quenched with NaHCO 3 (30 ml) and the organics extracted with 9,149.5,147.9,147.4,140.6,133.6,128.7,121.8,115.4,115.1,61.2,55.7,21.11,21.09 and 19.95 (3 x COCH 3 ). All other spectral data are identical to those previously reported by Khan et al (1986 …”

Section: S2 Experimentalsupporting

confidence: 85%

Pallidol hexaacetate ethyl acetate monosolvate

Mao

Taylor

et al. 2013

Acta Cryst E

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The entire molecule of pallidol hexaacetate {systematic name: (±)-(4bR,5R,9bR,10R)-5,10-bis[4-(acetyloxy)phenyl]-4b,5,9b,10-tetrahydroindeno[2,1-a]indene-1,3,6,8-tetrayl tetraacetate} is completed by the application of twofold rotational symmetry in the title ethyl acetate solvate, C40H34O12·C4H8O2. The ethyl acetate molecule was highly disordered and was treated with the SQUEEZE routine [Spek (2009). Acta Cryst. D65, 148–155]; the crystallographic data take into account the presence of the solvent. In pallidol hexaacetate, the dihedral angle between the fused five-membered rings (r.m.s. deviation = 0.100 Å) is 54.73 (6)°, indicating a significant fold in the molecule. Significant twists between residues are also evident as seen in the dihedral angle of 80.70 (5)° between the five-membered ring and the pendent benzene ring to which it is attached. Similarly, the acetate residues are twisted with respect to the benzene ring to which they are attached [C—O(carboxy)—C—C torsion angles = −70.24 (14), −114.43 (10) and −72.54 (13)°]. In the crystal, a three-dimensional architecture is sustained by C—H...O interactions which encompass channels in which the disordered ethyl acetate molecules reside

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Section: S2 Experimentalsupporting

confidence: 85%

Pallidol hexaacetate ethyl acetate monosolvate

Mao

Taylor

et al. 2013

Acta Cryst E

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“…Os estilbenos são comuns em Gnetaceae, Dipterocarpaceae e Vitaceae (Khan et al, 1986). O resveratrol é encontrado em várias plantas (Hart, 1981), mas uvas e produtos relacionados são consideradas as fontes mais importantes, e nelas o teor desse composto depende da variedade e das condições ecológicas do cultivo (Kallithraka et al, 2001;Sun et al, 2006).…”

Section: Resultsunclassified

Biciclogermacreno, resveratrol e atividade antifúngica em extratos de folhas de Cissus verticillata (L.) Nicolson & Jarvis (Vitaceae)

Silva¹,

Oniki²,

Agripino³

et al. 2007

Rev. bras. farmacogn.

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RESUMO:Cissus verticillata L. (Vitaceae) tem sido empregada popularmente como antidiabética. Nessa espécie foi também detectada atividade fungitóxica. O objetivo do presente trabalho foi realizar a identifi cação dos compostos fungitóxicos em extratos de folhas. O extrato etanólico foi submetido a fracionamento com solventes de diferentes polaridades (hexano, clorofórmio, acetato de etila e butanol) e seu efeito antifúngico foi analisado frente a Cladosporium sphaerospermum. Os extratos em clorofórmio e acetato de etila mostraram atividade, e foram fracionados por cromatografi a em coluna e cromatografi a preparativa em placas de sílica, respectivamente. Três terpenóides foram isolados do extrato em clorofórmio; um deles foi identifi cado, por análise em CG-EM, como um sesquiterpeno, o biciclogermacreno. O composto ativo do extrato em acetato de etila foi identifi cado, por análises em CLAE, como o estilbeno resveratrol.Unitermos: Cissus verticillata, Vitaceae, atividade fungitóxica, sesquiterpeno, estilbeno.ABSTRACTS: "Bicyclogermacrene, resveratrol and fungitoxic activity on leaves extracts of Cissus verticillata L. Nicolson & Jarvis (Vitaceae)". Cissus verticillata L. (Vitaceae) is popularly employed as hypoglicemic and it shows fungitoxic activity. This work aims at identifi cation of fungitoxic compounds on extracts of leaves. The ethanol extract was partitioned using solvents of different polarities (hexane, chloroform, ethyl acetate and butanol) and its fungitoxic activity was analysed upon Cladosporium sphaerospermum. The chloroform and ethyl acetate extracts showed activity and they were fractionated by column chromatography and preparative TLC, respectively. Three terpenoids were isolated from the chloroform extract, one of them identifi ed by GLC-MS analysis as sesquiterpene bicyclogermacrene. The active compound of the ethyl acetate extract was identifi ed by HPLC analyses as stilbene resveratrol.

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“…The structures of the three compounds were identified by direct comparison of the one and two-dimensional 1 H-and 13 C-NMR, mass and other physical and spectroscopic data with previously reported data. [13][14][15] Cell Culture and Transfection HeLa and HEK293 cells were grown in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10% fetal bovine serum, penicillin (100 units/ml), and streptomycin (100 mg/ml) at 37°C in a humidified atmosphere of 5% CO 2 and 95% air. HEK293 and HeLa cell lines stably expressing the human 5-HT 6 R, were selected with 800 mg/ml of G-418 and hygromycin, respectively, and maintained with 400 mg/ml of each selection drug.…”

Section: Plant Materialsmentioning

confidence: 99%

Stilbene Derivatives as Human 5-HT6 Receptor Antagonists from the Root of Caragana sinica

Kim

et al. 2010

Biological & Pharmaceutical Bulletin

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Serotonin (5-hydroxytryptamine, 5-HT) is an important neurotransmitter found in both the central and peripheral nervous systems.1-3) 5-HT mediates its diverse physiological responses via at least 16 different 5-HT receptors that are grouped into seven distinct subfamilies, the 5-HT 1-7 receptors. The human 5-HT receptor subtype 6 (5-HT 6 R) is one of the most recently cloned receptors among the known 5-HT receptors and belongs to the family of G-protein-coupled receptors (GPCRs) that positively couple to adenylate cyclase. [4][5][6] The 5-HT 6 R is mainly found in the central nervous system (CNS), and its abundant distribution in the limbic region, which participates in the control of mood and emotion, has generated much interest. 7,8) Despite intensive research attempts to identify selective 5-HT 6 ligands, only a very limited number of antagonists has progressed to clinical development. Furthermore, the cellular mechanisms underlying 5-HT 6 R-mediated behavioral changes are not well understood in the CNS. We previously developed a reliable cell-based high-throughput screening (HTS) method and screened synthetic chemical compounds to identify ligands of the 5-HT 6 R.9) This HTS method measures 5-HT-induced Ca 2ϩ increases using a promiscuous Ga 15 protein that facilitates coupling of Ga S -coupled receptors to phospholipase C and consequent intracellular Ca 2ϩ release, which is subsequently detected using an FDSS6000 96-well fluorescence plate reader. We furthermore utilized the FDSS6000 system to examine the functions of the 5-HT 6 R and its interacting proteins in several mammalian cell lines. 10,11) In the present study, as part of our continued efforts to identify novel 5-HT 6 ligands, we used the FDSS6000 system to screen natural products. Among a library of natural products examined, we found that the ethyl acetate fraction from the root of Caragana sinica (537-18BE) showed the strongest inhibition on the 5-HT 6 R. The genus Caragana is a member of the family Fabaceae and is widely distributed throughout the Euro-Asian continent. More than 10 species in this genus have a long history of use in traditional medicines, and the medicinal use of Caragana species was first noted when C. sinica has been traditionally used in the treatment of asthenia syndrome, vascular hypertension, leukorrhagia, bruises and contused wounds. Recent in vivo and/or in vitro studies have provided some support for other traditional uses, e.g. anti-cancer, anti-inflammatory, phytoestrogenic, immunostimulant and immunosuppressant activities. 12) However, further studies to identify the active components and verify the pharmacological activities are needed. Therefore, we further isolated 537-18BE to find active components for 5-HT 6 R-mediated Ca 2ϩ responses activity and found that three stilbene derivatives, (ϩ)-a-viniferin, miyabenol C and pallidol, produced an antagonistic effect to the 5-HT 6 R in the human 5-HT 6 R stably expressed HeLa and HEK293 cells. MATERIALS AND METHODS Plant MaterialsThe root of C. sinica was collected at ...

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Pallidol, a resveratrol dimer from Cissus pallida

Cited by 87 publications

References 13 publications

Pallidol hexaacetate ethyl acetate monosolvate

Pallidol hexaacetate ethyl acetate monosolvate

Biciclogermacreno, resveratrol e atividade antifúngica em extratos de folhas de Cissus verticillata (L.) Nicolson & Jarvis (Vitaceae)

Stilbene Derivatives as Human 5-HT6 Receptor Antagonists from the Root of Caragana sinica

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