Mesaconitine (BioDeep_00000000085)

   

PANOMIX_OTCML-2023


代谢物信息卡片


[(1S,2R,3R,4R,5R,6S,7S,8R,9R,10S,13R,14R,16S,17S,18R)-8-acetyloxy-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate

化学式: C33H45NO11 (631.299246)
中文名称: 美沙乌头碱, 中乌头碱, 新乌头碱, 新乌碱, 中乌头碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 0.63%

分子结构信息

SMILES: CC(=O)OC12C3C(CC(C3OC(=O)C4=CC=CC=C4)(C(C1O)OC)O)C56C(CC(C7(C5C(C2C6N(C7)C)OC)COC)O)OC
InChI: InChI=1S/C33H45NO11/c1-16(35)45-33-21-18(13-31(39,28(43-6)26(33)37)27(21)44-29(38)17-10-8-7-9-11-17)32-20(41-4)12-19(36)30(15-40-3)14-34(2)25(32)22(33)23(42-5)24(30)32/h7-11,18-28,36-37,39H,12-15H2,1-6H3/t18-,19-,20+,21-,22+,23+,24-,25+,26+,27-,28+,30+,31-,32+,33-/m1/s1

描述信息

Mesaconitine is a diterpenoid.
Mesaconitine is a natural product found in Aconitum anthora, Aconitum napellus, and other organisms with data available.
Origin: Plant; SubCategory_DNP: Terpenoid alkaloids, Diterpene alkaloid, Aconitum alkaloid
Annotation level-1
Mesaconitine is the main active component of genus aconitum plants. IC50 value: Target: in vitro: In HUVECs, 30 microM mesaconitine increased the [Ca(2+)](i) level in the presence of extracellular CaCl(2) and NaCl, and the response was inhibited by KBR7943. Mesaconitine increased intracellular Na(+) concentration level in HUVECs. The [Ca(2+)](i) response by mesaconitine was inhibited by 100 microM D-tubocurarine [1]. Mesaconitine at 30 microM inhibited 3 microM phenylephrine-induced contraction in the endothelium-intact, but not endothelium-denuded, aortic rings [2]. MA promoted the alpha-MT-induced decrease in NE levels in hippocampus, medulla oblongata plus pons and spinal cord [3].
Mesaconitine is the main active component of genus aconitum plants. IC50 value: Target: in vitro: In HUVECs, 30 microM mesaconitine increased the [Ca(2+)](i) level in the presence of extracellular CaCl(2) and NaCl, and the response was inhibited by KBR7943. Mesaconitine increased intracellular Na(+) concentration level in HUVECs. The [Ca(2+)](i) response by mesaconitine was inhibited by 100 microM D-tubocurarine [1]. Mesaconitine at 30 microM inhibited 3 microM phenylephrine-induced contraction in the endothelium-intact, but not endothelium-denuded, aortic rings [2]. MA promoted the alpha-MT-induced decrease in NE levels in hippocampus, medulla oblongata plus pons and spinal cord [3].

同义名列表

9 个代谢物同义名

mesaconitine hydrobromide, (1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-isomer of mesaconitine; N-desethyl-N-methylaconitine; XUHJBXVYNBQQBD-TUWOXVOMSA-N; Japaconitine B; Japaconitine A; Mesaconitine; [(1S,2R,3R,4R,5R,6S,7S,8R,9R,10S,13R,14R,16S,17S,18R)-8-acetyloxy-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate; Aconitane-3,8,13,14,15-pentol, 1,6,16-trimethoxy-4-(methoxymethyl)-20-methyl-, 8-acetate 14-benzoate, (1alpha,3alpha,6alpha,14alpha,15alpha,16beta)-; [(1S,4R,5R,6S,7S,8R,9R,10R,13R,14R,16S,18R)-8-acetyloxy-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate



数据库引用编号

37 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

25 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Hongyan Luo, Fangfang Zan, Jin Cui. Effect of microneedle roller on promoting transdermal absorption of crossbow-medicine liquid via transdermal administration of Traditional Chinese Medicine and the safety of crossbow-medicine needle therapy: An experimental study. Journal of ethnopharmacology. 2023 Jun; ?(?):116751. doi: 10.1016/j.jep.2023.116751. [PMID: 37295573]
  • Xiaocui Li, Weiqing Hou, Tingting Lin, Jiadong Ni, Huawei Qiu, Yu Fu, Zhongxiang Zhao, Caihua Yang, Na Li, Hua Zhou, Rong Zhang, Zhongqiu Liu, Ling Fu, Lijun Zhu. Neoline, fuziline, songorine and 10-OH mesaconitine are potential quality markers of Fuzi: In vitro and in vivo explorations as well as pharmacokinetics, efficacy and toxicity evaluations. Journal of ethnopharmacology. 2023 Mar; 303(?):115879. doi: 10.1016/j.jep.2022.115879. [PMID: 36370966]
  • Qi Wang, Jing Peng, Yang Liu, Yang Tian, Jie Li, Yao-Yao Ren, Jian Gu, Rui Tan. [Therapeutic effects of alkaloids in Tibetan medicine Bangna (Aconiti Penduli et Aconiti Flavi Radix) on osteoarthritis rats and mechanisms]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Sep; 47(17):4715-4722. doi: 10.19540/j.cnki.cjcmm.20220207.704. [PMID: 36164879]
  • Qian Chen, Kai Zhang, Mingjie Jiao, Jiakang Jiao, Dongling Chen, Yihui Yin, Jia Zhang, Fei Li. Study on the Mechanism of Mesaconitine-Induced Hepatotoxicity in Rats Based on Metabonomics and Toxicology Network. Toxins. 2022 07; 14(7):. doi: 10.3390/toxins14070486. [PMID: 35878224]
  • Yue Li, Dongming Yan, Jingyi Jin, Bo Tan, Xi Chen, Bin Zou, Guochao Song, Fengyi Weng, Chenghai Liu, Furong Qiu. Clarify the potential cholestatic hepatotoxicity components from Chinese Herb Medicine and metabolism's role via hBSEP vesicles and S9/hBSEP vesicles. Toxicology in vitro : an international journal published in association with BIBRA. 2022 Apr; 80(?):105324. doi: 10.1016/j.tiv.2022.105324. [PMID: 35101544]
  • Shu-Shong Hsu, Wei-Zhe Liang. Cytotoxic Effects of Mesaconitine, the Aconitum carmichaelii Debx Bioactive Compound, on HBEC-5i Human Brain Microvascular Endothelial Cells: Role of Ca2+ Signaling-Mediated Pathway. Neurotoxicity research. 2021 Apr; 39(2):256-265. doi: 10.1007/s12640-020-00249-2. [PMID: 32588354]
  • Yana Shi, Yi Zhao, Junxiang Qian, Zhiyuan Dong, Guosong Wen, Dake Zhao, Edward J Kennelly. Aconitum Diterpenoid Alkaloid Profiling to Distinguish between the Official Traditional Chinese Medicine (TCM) Fuzi and Adulterant Species Using LC-qToF-MS with Chemometrics. Journal of natural products. 2021 03; 84(3):570-587. doi: 10.1021/acs.jnatprod.0c00851. [PMID: 33496169]
  • Zemin Yang, Yanke Lin, Chong Su, Shuai Wang, Lu Gao, Jingpan Lin, Zhigang Wang, Baojian Wu. Pharmacokinetics-based chronoefficacy of Fuzi against chronic kidney disease. The Journal of pharmacy and pharmacology. 2021 Mar; 73(4):535-544. doi: 10.1093/jpp/rgaa060. [PMID: 33793835]
  • Jiaojiao Cong, Yiling Ruan, Qinglin Lyu, Xiaohui Qin, Xinming Qi, Wenyuan Liu, Lifeng Kang, Junying Zhang, Chunyong Wu. A proton-coupled organic cation antiporter is involved in the blood-brain barrier transport of Aconitum alkaloids. Journal of ethnopharmacology. 2020 Apr; 252(?):112581. doi: 10.1016/j.jep.2020.112581. [PMID: 31968215]
  • Zemin Yang, Yanke Lin, Lu Gao, Ziyue Zhou, Shuai Wang, Dong Dong, Baojian Wu. Circadian clock regulates metabolism and toxicity of Fuzi(lateral root of Aconitum carmichaeli Debx) in mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Feb; 67(?):153161. doi: 10.1016/j.phymed.2019.153161. [PMID: 31911401]
  • Yufei He, Zihong Wei, Xiaoyan Ci, Ying Xie, Xiulin Yi, Yong Zeng, Yazhuo Li, Changxiao Liu. Effects of liquorice on pharmacokinetics of aconitine in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2019 Dec; 49(12):1485-1493. doi: 10.1080/00498254.2019.1579007. [PMID: 30741588]
  • Weiming Xu, Min Zhang, Hongwu Liu, Kun Wei, Ming He, Xiangyang Li, Deyu Hu, Song Yang, Yuguo Zheng. Antiviral activity of aconite alkaloids from Aconitum carmichaelii Debx. Natural product research. 2019 May; 33(10):1486-1490. doi: 10.1080/14786419.2017.1416385. [PMID: 29271255]
  • Haolong Liu, Feng Qiu, Haiyu Zhao, Baolin Bian, Lei Wang. Simultaneous high-performance liquid chromatography with tandem mass spectrometry quantification of six bioactive components in rat plasma after oral administration of Yougui pill. Journal of separation science. 2019 May; 42(10):1867-1877. doi: 10.1002/jssc.201800772. [PMID: 30868717]
  • Xingxing Zong, Xiaojing Yan, Jian-Lin Wu, Zhongqiu Liu, Hua Zhou, Na Li, Liang Liu. Potentially Cardiotoxic Diterpenoid Alkaloids from the Roots of Aconitum carmichaelii. Journal of natural products. 2019 04; 82(4):980-989. doi: 10.1021/acs.jnatprod.8b01039. [PMID: 30892884]
  • Fugeng Zhang, Yu Zhang, Xiaofeng Li, Shaoqiang Zhang, Mingdan Zhu, Wuxun Du, Xuefeng Xiao. Research on Q-markers of Qiliqiangxin capsule for chronic heart failure treatment based on pharmacokinetics and pharmacodynamics association. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 May; 44(?):220-230. doi: 10.1016/j.phymed.2018.03.003. [PMID: 29699844]
  • Bing Yu, Yi Cao, Yao-Kang Xiong. Pharmacokinetics of aconitine-type alkaloids after oral administration of Fuzi (Aconiti Lateralis Radix Praeparata) in rats with chronic heart failure by microdialysis and ultra-high performance liquid chromatography-tandem mass spectrometry. Journal of ethnopharmacology. 2015 May; 165(?):173-9. doi: 10.1016/j.jep.2015.01.057. [PMID: 25708163]
  • Shuai Song, Qingfa Tang, Huiling Huo, Hancheng Li, Xuefeng Xing, Jiabo Luo. Simultaneous quantification and pharmacokinetics of alkaloids in Herba Ephedrae-Radix Aconiti Lateralis extracts. Journal of analytical toxicology. 2015 Jan; 39(1):58-68. doi: 10.1093/jat/bku113. [PMID: 25324527]
  • Yogini Jaiswal, Zhitao Liang, Alan Ho, LaiLai Wong, Peng Yong, Hubiao Chen, Zhongzhen Zhao. Distribution of toxic alkaloids in tissues from three herbal medicine Aconitum species using laser micro-dissection, UHPLC-QTOF MS and LC-MS/MS techniques. Phytochemistry. 2014 Nov; 107(?):155-74. doi: 10.1016/j.phytochem.2014.07.026. [PMID: 25172517]
  • Yu V Nesterova, T N Povet'yeva, N I Suslov, G N Zyuz'kov, S V Pushkarskii, S G Aksinenko, E E Schultz, S S Kravtsova, A V Krapivin. Analgesic activity of diterpene alkaloids from Aconitum baikalensis. Bulletin of experimental biology and medicine. 2014 Aug; 157(4):488-91. doi: 10.1007/s10517-014-2598-6. [PMID: 25110090]
  • Bo Sun, Ming Zhang, Qi Zhang, Kunpeng Ma, Haijing Li, Famei Li, Fangting Dong, Xianzhong Yan. Metabonomics study of the effects of pretreatment with glycyrrhetinic acid on mesaconitine-induced toxicity in rats. Journal of ethnopharmacology. 2014 Jul; 154(3):839-46. doi: 10.1016/j.jep.2014.05.010. [PMID: 24846827]
  • Wen-Wen Peng, Wen Li, Jun-Song Li, Xiao-Bing Cui, Yong-xin Zhang, Guang-Ming Yang, Hong-Mei Wen, Bao-Chang Cai. The effects of Rhizoma Zingiberis on pharmacokinetics of six Aconitum alkaloids in herb couple of Radix Aconiti Lateralis-Rhizoma Zingiberis. Journal of ethnopharmacology. 2013 Jul; 148(2):579-86. doi: 10.1016/j.jep.2013.04.056. [PMID: 23707213]
  • Jin-Ming Zhang, Wan Liao, Yu-xin He, Yao He, Dong Yan, Chao-Mei Fu. Study on intestinal absorption and pharmacokinetic characterization of diester diterpenoid alkaloids in precipitation derived from fuzi-gancao herb-pair decoction for its potential interaction mechanism investigation. Journal of ethnopharmacology. 2013 May; 147(1):128-35. doi: 10.1016/j.jep.2013.02.019. [PMID: 23506993]
  • Ling Ye, Xiaoshan Yang, Zhen Yang, Song Gao, Taijun Yin, Wei Liu, Feng Wang, Ming Hu, Zhongqiu Liu. The role of efflux transporters on the transport of highly toxic aconitine, mesaconitine, hypaconitine, and their hydrolysates, as determined in cultured Caco-2 and transfected MDCKII cells. Toxicology letters. 2013 Feb; 216(2-3):86-99. doi: 10.1016/j.toxlet.2012.11.011. [PMID: 23200901]
  • Rui-Qing Wen, Dong-Hui Li, Xin Zhao, Jia-Bo Wang, Yan-Ling Zhao, Ping Zhang, Zhi-Yong Sun, Dan Yan, Xiao-He Xiao, Yu-Zhen Ren, Fei Li, Jie Du, Hai-Yan Zhou. [Rationality of the processing methods of aconiti lateralis radix (Fuzi) based on chemical analysis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2013 Feb; 48(2):286-90. doi: ". [PMID: 23672028]
  • Kohei Kazuma, Motoyoshi Satake, Katsuhiro Konno. [Case of fatal aconite poisoning, and its background]. Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan. 2013; 54(6):419-25. doi: 10.3358/shokueishi.54.419. [PMID: 24389474]
  • Ping Cui, Han Han, Rui Wang, Li Yang. Identification and determination of Aconitum alkaloids in Aconitum herbs and Xiaohuoluo pill using UPLC-ESI-MS. Molecules (Basel, Switzerland). 2012 Aug; 17(9):10242-57. doi: 10.3390/molecules170910242. [PMID: 22926305]
  • Na Li, Rong Tsao, Zhigang Sui, Jingwei Ma, Zhiqiang Liu, Zhongying Liu. Intestinal transport of pure diester-type alkaloids from an aconite extract across the Caco-2 cell monolayer model. Planta medica. 2012 May; 78(7):692-7. doi: 10.1055/s-0031-1298368. [PMID: 22411726]
  • Hong-Fei Zhang, Yan-Ping Shi. Preparation of Fe3O4 nanoparticle enclosure hydroxylated multi-walled carbon nanotubes for the determination of aconitines in human serum samples. Analytica chimica acta. 2012 Apr; 724(?):54-60. doi: 10.1016/j.aca.2012.02.039. [PMID: 22483209]
  • Yu V Nesterova, T N Povetieva, N I Suslov, V V Zhdanov, T Yu Hrichkova, E V Udut, A S Chaykovskiy, N N Gaydamovich, T I Andreeva, A M Dygai. Regeneratory characteristics of complex extract and isolated diterpene alkaloids of Aconitum baikalense. Bulletin of experimental biology and medicine. 2012 Feb; 152(4):439-43. doi: 10.1007/s10517-012-1548-4. [PMID: 22803106]
  • Xin Dong, Shu-Min Wang, Xiao-Ming Li, Feng-Rui Song, Zhi-Qiang Liu, Shu-Ying Liu. [Determination of content changes of three diester-diterpenoid alkaloids in compatibility of radix aconiti laterlis preparata and Rhizoma pinelliae, Fructus trichosanthis, Bulbus fritillariae, Radix ampelopsis, Rhizoma bletillae by HPLC]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Dec; 34(12):1891-4. doi: ". [PMID: 22500426]
  • Zhuo Liu, Xing Yan, Chun-Xia Xu, Da-Bin Hou, Xiao-Hong Yuan. [Extraction technology of diester-type alkaloids from Radix Aconiti lateralis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Nov; 34(11):1781-4. doi: ". [PMID: 22506406]
  • Yi Bao, Fan Yang, Xiurong Yang. CE-electrochemiluminescence with ionic liquid for the facile separation and determination of diester-diterpenoid aconitum alkaloids in traditional Chinese herbal medicine. Electrophoresis. 2011 Jun; 32(12):1515-21. doi: 10.1002/elps.201100040. [PMID: 21692082]
  • Hong Shen, Ling-ying Zhu, Nan Yao, Jie Wu. [The effect of the compatibility of Radix Aconiti Laterlis and radix glycyrrhizae on pharmacokinatic of aconitine, mesaconitine and hypacmitine in rat plasma]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Jun; 34(6):937-42. doi: . [PMID: 22017011]
  • Ligang Zhao, Liang Fang, Yan Li, Ni Zheng, Yongnan Xu, Jinghua Wang, Zhonggui He. Effect of (E)-2-isopropyl-5-methylcyclohexyl octadec-9-enoate on transdermal delivery of Aconitum alkaloids. Drug development and industrial pharmacy. 2011 Mar; 37(3):290-9. doi: 10.3109/03639045.2010.510141. [PMID: 21054218]
  • Yang Yang, Juan Chen, Yan-Ping Shi. Determination of aconitine, hypaconitine and mesaconitine in urine using hollow fiber liquid-phase microextraction combined with high-performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Oct; 878(28):2811-6. doi: 10.1016/j.jchromb.2010.08.032. [PMID: 20846913]
  • Chao Wang, Yu-guang Wang, Qian-de Liang, Wei-qing Rang, Yue Gao. [Analysis of chemical composition in the combination of monkshood and pinellia by UPLC/Q-TOFMS with multivariate statistical analysis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Oct; 45(10):1301-6. doi: . [PMID: 21348310]
  • Ping-ping Chen, Ning Zhao, Xiu-ling Xu, Ye-ping Ruan, Ying-hui Wei, Fan-zhu Li. [Analysis on the metabolites of mesaconitine in the rat urine by liquid chromatography and electrospray ionization mass spectrometry]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Aug; 45(8):1043-7. doi: . [PMID: 21351593]
  • Hai-Yan Zhou, Lan Sun, Run-Huai Zhao, Lei Zhang, Yong Yang, Qi Chang. [Evaluation of the accumulation of dry substance and active componentsevaluation of the accumulation of dry substance and active components of Radix Aconiti Lateralis Praeparata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Apr; 33(4):487-9. doi: ". [PMID: 20845771]
  • Jing-Zheng Song, Quan-Bin Han, Chun-Feng Qiao, Paul Pui-Hay But, Hong-Xi Xu. Development and validation of a rapid capillary zone electrophoresis method for the determination of aconite alkaloids in aconite roots. Phytochemical analysis : PCA. 2010 Mar; 21(2):137-43. doi: 10.1002/pca.1168. [PMID: 19810124]
  • Bo Sun, Ling Li, Shengming Wu, Qi Zhang, Haijing Li, Hebing Chen, Famei Li, Fangting Dong, Xianzhong Yan. Metabolomic analysis of biofluids from rats treated with Aconitum alkaloids using nuclear magnetic resonance and gas chromatography/time-of-flight mass spectrometry. Analytical biochemistry. 2009 Dec; 395(2):125-33. doi: 10.1016/j.ab.2009.08.014. [PMID: 19683504]
  • Lei-ping He, Bin Di, Ying-xiang Du, Fang Yan, Meng-xiang Su, Hua-qing Liu, Lin-jun You. Development and validation of a high-performance liquid chromatography-tandem mass spectrometry method for the rapid simultaneous quantification of aconitine, mesaconitine, and hypaconitine in rat plasma after oral administration of Sini decoction. Journal of analytical toxicology. 2009 Nov; 33(9):588-94. doi: 10.1093/jat/33.9.588. [PMID: 20040133]
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