Nine bisabolangelone reduction derivatives were synthesized and separated as potential anti-ulcer agent. Their structures were characterized by 2D NMR, IR, ESI-MS, elemental analysis and single-crystal X-ray diffracti...Nine bisabolangelone reduction derivatives were synthesized and separated as potential anti-ulcer agent. Their structures were characterized by 2D NMR, IR, ESI-MS, elemental analysis and single-crystal X-ray diffraction analysis. Preliminarily H＋/K＋-ATPase activity evaluation indicated that all the target compounds had a certain inhibitory effect, and compounds Ⅱ and IV exhibited the better inhibitory activity against H＋/K＋-ATPase than bisabolangelone and the commercial omeprazole with the IC50 of 23.21 and 65.32 pmol/L, respectively. The initial structure-activity analysis suggested that the presence of carbonyl group in six-membered ring and double bond in side-chain seemed to be necessary to the activity.展开更多
The title compound of（3S,4R,Z）-3,6-dimethyl-2-（3-methylbut-2-enylidene）-2,3,3a,4,7,7a-hexahydrobenzofuran-3,4-diol,C15H22O3,as a potential gastric cytoprotective agent has been synthesized by the reduction of bisa...The title compound of（3S,4R,Z）-3,6-dimethyl-2-（3-methylbut-2-enylidene）-2,3,3a,4,7,7a-hexahydrobenzofuran-3,4-diol,C15H22O3,as a potential gastric cytoprotective agent has been synthesized by the reduction of bisabolangelone in methanol with sodium borohydride.The title compound was characterized by IR and NMR spectra.Meanwhile,the crystal was obtained and determined by X-ray single-crystal diffraction.Crystal data：monoclinic system,space group P21 with a = 6.0692（12）,b = 8.9954（18）,c = 13.182（3） ,β = 92.59（3）°,V = 718.9（2） 3,Z = 2,F（000） = 272,Dc = 1.156 g/cm3,μ = 0.633 mm-1,R = 0.0362 and wR = 0.1051 for 9490 independent reflections（Rint = 0.0172） and 2461 observed reflections（I 2σ（I））.Intermolecular O-H…O interactions link the molecules into one-dimensional infinite chains running along the b axis,which contributes to the stability of the crystal structure.展开更多
To investigate the anti-ulcer effect of bisabolangelone reduction derivatives, the sesquiterpene was further proceeded with dihydroxylation reaction. The structure of the target compound was characterized by IR, ESI-M...To investigate the anti-ulcer effect of bisabolangelone reduction derivatives, the sesquiterpene was further proceeded with dihydroxylation reaction. The structure of the target compound was characterized by IR, ESI-MS, 2D NMR and elemental analysis, and its absolute configuration was confirmed with a Flack parameter of 0.08（16） by X-ray crystallography using a Cu radiation source. Compound（3）, C（15）H（26）O5, crystal data： monoclinic system, space group P21, a = 11.467（2）, b = 6.0303（12）, c = 11.711（2） A, β = 99.70（3）°, V = 798.3（3） A3, Z = 2, F（000） = 312, Dc = 1.191 g/cm3, μ = 0.723 mm-1） R = 0.0303 and wR = 0.0797 for 2590 independent reflections（Rint = 0.0164） and 2563 observed ones（I 〉 2σ（I））.展开更多
基金Project supported by the National Natural Science Foundation of China （No. 30970296）, the Scientific and Technological Research Project of Hubei Provincial Department of Education （No. Q20111210）, the Doctoral Startup Foundation of China Three Gorges University （No. KJ2009B046） and the Preresearch Foundation of College of Chemistry and Life Sciences （No. HY0905）.
文摘Nine bisabolangelone reduction derivatives were synthesized and separated as potential anti-ulcer agent. Their structures were characterized by 2D NMR, IR, ESI-MS, elemental analysis and single-crystal X-ray diffraction analysis. Preliminarily H＋/K＋-ATPase activity evaluation indicated that all the target compounds had a certain inhibitory effect, and compounds Ⅱ and IV exhibited the better inhibitory activity against H＋/K＋-ATPase than bisabolangelone and the commercial omeprazole with the IC50 of 23.21 and 65.32 pmol/L, respectively. The initial structure-activity analysis suggested that the presence of carbonyl group in six-membered ring and double bond in side-chain seemed to be necessary to the activity.
基金supported by the National Natural Science Foundation of China (No. 30970296,30870254)Scientific and Technological Research Project of Hubei Provincial Department of Education (Q20111210)+1 种基金Doctoral Startup Foundation of China Three Gorges University (No. KJ2009B046)Pre-research Foundation of College of Chemistry and Life Sciences (No. HY0905)
文摘The title compound of（3S,4R,Z）-3,6-dimethyl-2-（3-methylbut-2-enylidene）-2,3,3a,4,7,7a-hexahydrobenzofuran-3,4-diol,C15H22O3,as a potential gastric cytoprotective agent has been synthesized by the reduction of bisabolangelone in methanol with sodium borohydride.The title compound was characterized by IR and NMR spectra.Meanwhile,the crystal was obtained and determined by X-ray single-crystal diffraction.Crystal data：monoclinic system,space group P21 with a = 6.0692（12）,b = 8.9954（18）,c = 13.182（3） ,β = 92.59（3）°,V = 718.9（2） 3,Z = 2,F（000） = 272,Dc = 1.156 g/cm3,μ = 0.633 mm-1,R = 0.0362 and wR = 0.1051 for 9490 independent reflections（Rint = 0.0172） and 2461 observed reflections（I 2σ（I））.Intermolecular O-H…O interactions link the molecules into one-dimensional infinite chains running along the b axis,which contributes to the stability of the crystal structure.
基金supported by the National Natural Science Foundation of China(No.21602123)China Scholarship Council(No.201508420062)Youth Talent Development Foundation of China Three Gorges University
文摘To investigate the anti-ulcer effect of bisabolangelone reduction derivatives, the sesquiterpene was further proceeded with dihydroxylation reaction. The structure of the target compound was characterized by IR, ESI-MS, 2D NMR and elemental analysis, and its absolute configuration was confirmed with a Flack parameter of 0.08（16） by X-ray crystallography using a Cu radiation source. Compound（3）, C（15）H（26）O5, crystal data： monoclinic system, space group P21, a = 11.467（2）, b = 6.0303（12）, c = 11.711（2） A, β = 99.70（3）°, V = 798.3（3） A3, Z = 2, F（000） = 312, Dc = 1.191 g/cm3, μ = 0.723 mm-1） R = 0.0303 and wR = 0.0797 for 2590 independent reflections（Rint = 0.0164） and 2563 observed ones（I 〉 2σ（I））.
