ChemInform Abstract: Synthesis, Structure Elucidation and H<sup>+</sup>/K<sup>+</sup>‐ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives.

Huang, Nianyu; Chen, Lei; Liao, Z.; Fang, Hubiao; Wang, Junzhi; Zou, Kun

doi:10.1002/chin.201221203

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“…Bisabolangelone, as esquiterpene isolated from ther oots of Angelica polymorpha Maximw ith the traditional Tujia medicine nameofZijinsha [2], displayed attractive bioactivitysuch as anti-feeding and insecticidal effect [3][4][5]. Recently,wefound bisabolangelonealsoexhibited remarkably preventive and therapeutic action on gastric ulcer, and its anti-ulcer mechanism might be related to inhibition of the H + /K + -ATPase and reduction of the secretion of H + [6].However, it was found to be moderate acutetoxic towardsmicei.g administrated with the LD 50 of 76.60 mg/kg in our previous reports [7].With the aim of studying the relationship between its structure and H + /K + -ATPase inhibition activity, especially for decreasing its acute toxicity, the catalytic hydrogen reduction of bisabolangelone were undertaken [8]. The H + ,K + -ATPase inhibitory activity for the target compound was better than bisabolangelone andt he commercial omeprazole with the IC 50 of 23.21 mmol/L [8][9].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

Yang¹,

al.²

2012

Zeitschrift für Kristallographie - New Crystal Structures

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Source of materialThebisabolangelone (0.26g,1.0 mmol)and Pd/C (0.05g,10% w/w)was dissolvedinEtOH(20 ml)at25°Cunder dry nitrogen atmosphere, then hydrogen gas (99%) was bubbled into the vigorous stirred solution (300 ml/minute) for 2.0 hu ntil the bisabolangelone was completely consumed. Filtration of the catalyst and removing the solvents at reduced pressure give white solids, which was purified by columnchromatography on silica with ethylacetate/petroleum ether (1:3) as eluent to give four pure target compound as colourless needles (0.21 g). X-ray quality crystals were obtained by the vapor diffusion of diethyl ether into a solution of the target compound in EtOAc at room temperature, and the colourless orthorhombic crystal with dimensions of 0.23´0.18´0.16 mm wasselectedfor measurement. Diffraction data of the single-crystal were collected at 296(2) KonaRigaku Mecury CCDd iffractometere quippedw ithag raphite-monochromatic Mo Ka (l =0.71073 Å) by Crystal clear software. Atotal of 2766 reflections were collected in the range of 2.74°£ q £ 25.01°by using an w-scan mode, of which 6799 were unique with R int =0.0659 and 2198 were observed with I>2s(I).Empirical absorption corrections were applied. The structures were solved by direct methods using SHELX programs [11]. All of the nonhydrogen atomswere located from the difference Fourier maps, and then refined anisotropically with SHELXL97 via afull-matrix least-square procedure [11].The hydrogen atomswere added according to the theoretically model. Experimental detailsThe positionsofall Hatoms were determined geometrically and refinedu sing ar idingm odel with C-H =0 .93-0.97 Åa nd U iso (methyl H) =1.5 U eq (C) and 1.2 U eq for other Hatoms.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

Yang¹,

al.²

2012

Zeitschrift für Kristallographie - New Crystal Structures

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ChemInform Abstract: Synthesis, Structure Elucidation and H⁺/K⁺‐ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives.

Abstract: Among a variety of reduction derivatives, the compounds (I) and (II) exhibit better inhibitory activity against H+/K+‐ATPase than omeprazole.

Cited by 1 publication

References 1 publication

Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

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ChemInform Abstract: Synthesis, Structure Elucidation and H+/K+‐ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives.

Abstract: Among a variety of reduction derivatives, the compounds (I) and (II) exhibit better inhibitory activity against H+/K+‐ATPase than omeprazole.

Cited by 1 publication

References 1 publication

Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

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ChemInform Abstract: Synthesis, Structure Elucidation and H⁺/K⁺‐ATPase Inhibitory Activity of Bisabolangelone Reduction Derivatives.