The anti-ulcer activities of bisabolangelone from Angelica polymorpha

Wang, Junzhi; Zhu, Liebin; Zou, Kun; Cheng, Fan; Dan, Feijun; Guo, Zhiyong; Zheng-jun, Cai; Yang, Ji-Min

doi:10.1016/j.jep.2009.02.048

Cited by 38 publications

(23 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently,wefound bisabolangelonealso exhibited remarkable 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 + [8].However, it was found to be moderately acutetoxic towards mice, e.g. administrated with the LD 50 of 76.60 mg/kg in our previous reports [9].With the aim of studying the relationship between its structure and H + /K + -ATPase inhibitiona ctivity, especiallyf or decreasingi ts acute toxicity, the catalytic hydrogenationofbisabolangelone was undertaken.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (3S,Z)-3-hydroxy-3,6-dimethyl-2-(3-methylbutylidene)- 3,3a,7,7a-tetrahydrobenzofuran-4(2H)-one, C15H22O3

Fang¹,

Chen²,

Huang³

et al. 2012

Zeitschrift Für Kristallographie - New Crystal Structures

Self Cite

View full text Add to dashboard Cite

Source of materialBisabolangelone(0.25 g, 1.0mmol) and Pd/C(0.02 g, 10 % w/w) weredissolved in MeOH (20 ml) at 10°C under dry nitrogen atmosphere, then hydrogen gas (99 %) was bubbled into the vigorously stirred solution (100 ml/minute) for 0.5 hu ntil the bisabolangelone wasconsumed. Thecatalystwas filtered off and thesolventsevaporatedatreduced pressure to give awhite solid, whichw as purified by column chromatography on silica with ethylacetate/petroleum ether (1:6) as eluent to give thepuretargetcompoundascolorless needles (0.18 g). X-ray quality crystals were obtained by vapor diffusion of diethyl ether into asolution of the target compound in CHCl 3 at room temperature, and the colorless orthorhombic crystal was selected for measurement. ExperimentalAllofthe non-hydrogen atoms were located from the difference Fourier maps,and then refined anisotropically [1].The hydrogen atomswere added according to the theoretical model. The positionsofall Hatoms were determined geometrically andrefined using ar iding model with d(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.The structure was checked with PLATON [2]. The absolute configuration of the title crystal structure could not be determined using data collectedwithMoK a radiation(Flackparameter x =2(3)).The huge R values are presumably caused by the poor quality of thecrystal.Wehave been fortunate to obtain the single crystals from the very limited amount of material synthesized through reducing of bisabolangelone, which was isolated from the roots of Angelica polymorpha Maxim. DiscussionThe H + /K + -ATPasei st he proton pump responsible for gastric acid secretion [ 3].B isabolangelone,asesquiterpene isolated from the roots of Angelica polymorpha Maxim with the traditional Tujia medicine name of Zijinsha [4], displayed attractive bioactivity such as anti-feeding and insecticidal effect [5][6][7]. Recently,wefound bisabolangelonealso exhibited remarkable 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 + [8].However, it was found to be moderately acutetoxic towards mice, e.g. administrated with the LD 50 of 76.60 mg/kg in our previous reports [9].With the aim of studying the relationship between its structure and H + /K + -ATPase inhibitiona ctivity, especiallyf or decreasingi ts acute toxicity, the catalytic hydrogenationofbisabolangelone was undertaken. Therefore, the structure determination of the title compound was conducted by X-ray single-crystal analysis for the first time. Compared with the crystal structure of bisabolangelone [10], most bond lengths in the crystal were in the normalrange of single or double bonds. The bond angles containing unsaturated bonds in ÐO1-C1-C2, ÐC2-C3-C7 and ÐC11-C9-C8 ranged from 121°to 128°. The torsion angles of C4-C5-C5-C8a nd O2-C5-C6-C1 were equal to 86.7(3)°and 157.9(3)°, respectively. Theside chain of 3-methylbutylidene in tetrahydrofuran ring disordere...

show abstract

Section: Discussionmentioning

confidence: 99%

Crystal structure of (3S,Z)-3-hydroxy-3,6-dimethyl-2-(3-methylbutylidene)- 3,3a,7,7a-tetrahydrobenzofuran-4(2H)-one, C15H22O3

Fang¹,

Chen²,

Huang³

et al. 2012

Zeitschrift Für Kristallographie - New Crystal Structures

Self Cite

View full text Add to dashboard Cite

show abstract

“…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

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…The bisabolangelone was extracted and isolated from the roots of Angelica polymorpha Maxim. [10] Column chromatography was performed using 200-300 mesh silica gel.…”

Section: Materials and Physical Measurementsmentioning

confidence: 99%

“…[8] Recently, we found bisabolangelone also exhibited remarkably preventive and therapeutic action on gastric ulcer, [9] and its anti-ulcer mechanism might be related to inhibition of the H ＋ /K ＋ -ATPase and reduction of the secretion of H ＋ . [10] Unfortunately, it was also found to be moderate acute toxic towards mice i.g. administrated with the LD 50 of 76.60 mg/kg in our previous reports.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

Self Cite

View full text Add to dashboard Cite

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 IC 50 of 23.21 and 65.32 µmol/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.

show abstract

The anti-ulcer activities of bisabolangelone from Angelica polymorpha

Cited by 38 publications

References 9 publications

Crystal structure of (3S,Z)-3-hydroxy-3,6-dimethyl-2-(3-methylbutylidene)- 3,3a,7,7a-tetrahydrobenzofuran-4(2H)-one, C15H22O3

Crystal structure of (3S,Z)-3-hydroxy-3,6-dimethyl-2-(3-methylbutylidene)- 3,3a,7,7a-tetrahydrobenzofuran-4(2H)-one, C15H22O3

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

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

Contact Info

Product

Resources

About

The anti-ulcer activities of bisabolangelone from Angelica polymorpha

Cited by 38 publications

References 9 publications

Crystal structure of (3S,Z)-3-hydroxy-3,6-dimethyl-2-(3-methylbutylidene)- 3,3a,7,7a-tetrahydrobenzofuran-4(2H)-one, C15H22O3

Crystal structure of (3S,Z)-3-hydroxy-3,6-dimethyl-2-(3-methylbutylidene)- 3,3a,7,7a-tetrahydrobenzofuran-4(2H)-one, C15H22O3

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

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

Contact Info

Product

Resources

About

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