Isosteviol (BioDeep_00000229947)

 

Secondary id: BioDeep_00000895085

PANOMIX_OTCML-2023 Antitumor activity natural product


代谢物信息卡片


(4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-Trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid

化学式: C20H30O3 (318.21948299999997)
中文名称: 异甜菊醇
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 50%

分子结构信息

SMILES: CC12CCC3C4(CCCC(C4CCC3(C1)CC2=O)(C)C(=O)O)C
InChI: InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1

描述信息

Isosteviol is a diterpenoid.
Isosteviol is a natural product found in Ceriops decandra with data available.
See also: Stevia rebaudiuna Leaf (part of).
Isosteviol ((-)-Isosteviol) is a derivative of Stevioside through acid catalyzed hydrolysis of Stevioside. Isosteviol inhibits DNA polymerase and DNA topoisomerase and has antibacterial, anticancer and anti-tuberculosis effects[1][2][3][4].
Isosteviol ((-)-Isosteviol) is a derivative of Stevioside through acid catalyzed hydrolysis of Stevioside. Isosteviol inhibits DNA polymerase and DNA topoisomerase and has antibacterial, anticancer and anti-tuberculosis effects[1][2][3][4].

同义名列表

16 个代谢物同义名

(4R,4aS,6aR,9S,11aR,11bS)-4,9,11b-Trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid; (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid; 17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4.ALPHA.,8.BETA.,13.BETA.)-; 17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4-alpha,8-beta,13-beta)-; 17-NORKAURAN-18-OIC ACID, 13-METHYL-16-OXO-, (4alpha,8beta,13beta)-; (4-alpha,8-beta,13-beta)-13-Methyl-16-oxo-17-norkauran-18-oic acid; (4-alpha,8-beta,13-beta)-13-methyl-16-oxo-17-norkauran-18-oicacid; (4alpha,8beta,13beta)-13-methyl-16-oxo-17-norkauran-18-oic acid; 17-Nor-8-beta,13-beta-kauran-18-oic acid, 13-methyl-16-oxo-; 17-Norkauran-18-oic acid, 13-methyl-16-oxo-, (4a,8b,13b)-; ent-16-ketobeyeran-19-oic acid; Ketoisostevic Acid; (-)-Isosteviol; iso-steviol; Isosteviol; (-)-Isosteviol;iso-Steviol



数据库引用编号

14 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)

11 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

  • J Z Altamimi, N A Alfaris, G M Alshammari, R I Alagal, D H Aljabryn, M A Yahya. Isosteviol attenuates streptozotocin-mediated diabetic nephropathy in rats by upregulating and stimulating adenosine monophosphate-activated protein kinase. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 2023 Jun; 74(3):. doi: 10.26402/jpp.2023.3.06. [PMID: 37661183]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Ying Mei, Hui Hu, Liangjun Deng, Xiaoou Sun, Wen Tan. Isosteviol sodium attenuates high fat/high cholesterol-induced myocardial dysfunction by regulating the Sirt1/AMPK pathway. Biochemical and biophysical research communications. 2022 09; 621(?):80-87. doi: 10.1016/j.bbrc.2022.06.044. [PMID: 35810595]
  • Ying Mei, Hui Hu, Liangjun Deng, Xiaoou Sun, Wen Tan. Therapeutic effects of isosteviol sodium on non-alcoholic fatty liver disease by regulating autophagy via Sirt1/AMPK pathway. Scientific reports. 2022 07; 12(1):12857. doi: 10.1038/s41598-022-16119-0. [PMID: 35896572]
  • Shanping Wang, Jiandong Huang, Keai Sinn Tan, Liangjun Deng, Fei Liu, Wen Tan. Isosteviol Sodium Ameliorates Dextran Sodium Sulfate-Induced Chronic Colitis through the Regulation of Metabolic Profiling, Macrophage Polarization, and NF-κB Pathway. Oxidative medicine and cellular longevity. 2022; 2022(?):4636618. doi: 10.1155/2022/4636618. [PMID: 35126813]
  • Shanping Wang, Keai Sinn Tan, Huimin Beng, Fei Liu, Jiandong Huang, Yihe Kuai, Rui Zhang, Wen Tan. Protective effect of isosteviol sodium against LPS-induced multiple organ injury by regulating of glycerophospholipid metabolism and reducing macrophage-driven inflammation. Pharmacological research. 2021 10; 172(?):105781. doi: 10.1016/j.phrs.2021.105781. [PMID: 34302975]
  • Gertrud E Morlock, Julia Heil. HI-HPTLC-UV/Vis/FLD-HESI-HRMS and bioprofiling of steviol glycosides, steviol, and isosteviol in Stevia leaves and foods. Analytical and bioanalytical chemistry. 2020 Sep; 412(24):6431-6448. doi: 10.1007/s00216-020-02618-4. [PMID: 32328691]
  • Ayorinde Adehin, Keai Sinn Tan, Chengjuan Zou, Zhiqiang Lu, Yue Lin, Dongfang Wang, Qing Cheng, Wen Tan. A compartmental approach to isosteviol's disposition in Sprague-Dawley rats. Naunyn-Schmiedeberg's archives of pharmacology. 2020 06; 393(6):1003-1011. doi: 10.1007/s00210-019-01757-5. [PMID: 31820053]
  • U A Ogorodnova, A S Sapunova, O A Timofeeva, V F Mironov. Stevioside Has the Maximum Biological Activity among Natural Stevia Diterpenes. Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections. 2020 May; 492(1):79-82. doi: 10.1134/s0012496620030060. [PMID: 32632831]
  • Yang Shi, Bo-Wen Pan, Wen-Chao Li, Qing Wang, Qiong Wu, Meng Pan, Hong-Zheng Fu. Synthesis and biological evaluation of Isosteviol derivatives as FXa inhibitors. Bioorganic & medicinal chemistry letters. 2020 01; 30(2):126585. doi: 10.1016/j.bmcl.2019.07.044. [PMID: 31859158]
  • Ying Mei, Yihe Kuai, Hui Hu, Fei Liu, Bo Liu, Xiaoou Sun, Wen Tan. Isosteviol Sodium Attenuates High Fat/High Cholesterol-Induced Kidney Dysfunction by Inhibiting Inflammation, Oxidative Stress and Apoptosis. Biological & pharmaceutical bulletin. 2020; 43(8):1172-1178. doi: 10.1248/bpb.b19-01028. [PMID: 32741937]
  • Hongwei Yi, Deyi Xu, Xudong Wu, Fang Xu, Lin Lin, Huiping Zhou. Isosteviol Protects Free Fatty Acid- and High Fat Diet-Induced Hepatic Injury via Modulating PKC-β/p66Shc/ROS and Endoplasmic Reticulum Stress Pathways. Antioxidants & redox signaling. 2019 06; 30(17):1949-1968. doi: 10.1089/ars.2018.7521. [PMID: 30484323]
  • C Gardana, P Simonetti. Determination of steviol glycosides in commercial extracts of Stevia rebaudiana and sweeteners by ultra-high performance liquid chromatography Orbitrap mass spectrometry. Journal of chromatography. A. 2018 Nov; 1578(?):8-14. doi: 10.1016/j.chroma.2018.09.057. [PMID: 30287064]
  • Yang Yang, Qisheng Zhong, Hao Zhang, Canlong Mo, Jinting Yao, Taohong Huang, Ting Zhou, Wen Tan. Lipidomics study of the protective effects of isosteviol sodium on stroke rats using ultra high-performance supercritical fluid chromatography coupling with ion-trap and time-of-flight tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2018 Aug; 157(?):145-155. doi: 10.1016/j.jpba.2018.05.022. [PMID: 29800902]
  • Huey-En Tzeng, Po-Hao Huang, Chun-Hao Tsai, Gregory J Tsay, Yi-Ju Lee, Tsurng-Juhn Huang, Tzu-Hung Lin, Ying-Ming Chiu, Yi-Ying Wu. Isosteviol Derivative Inhibits Osteoclast Differentiation and Ameliorates Ovariectomy-Induced Osteoporosis. Scientific reports. 2018 07; 8(1):11190. doi: 10.1038/s41598-018-29257-1. [PMID: 30046042]
  • Sheng-Gao Tang, Xiao-Yu Liu, Ji-Ming Ye, Ting-Ting Hu, Ying-Ying Yang, Ting Han, Wen Tan. Isosteviol ameliorates diabetic cardiomyopathy in rats by inhibiting ERK and NF-κB signaling pathways. The Journal of endocrinology. 2018 07; 238(1):47-60. doi: 10.1530/joe-17-0681. [PMID: 29720537]
  • Baxter Hepburn Kachingwe, Yow-Shieng Uang, Tsurng-Juhn Huang, Li-Hsuan Wang, Shwu-Jiuan Lin. Development and validation of an LC-MS/MS method for quantification of NC-8 in rat plasma and its application to pharmacokinetic studies. Journal of food and drug analysis. 2018 01; 26(1):401-408. doi: 10.1016/j.jfda.2017.09.003. [PMID: 29389580]
  • Lara Testai, Irina Strobykina, Victor V Semenov, Marina Semenova, Eleonora Da Pozzo, Alma Martelli, Valentina Citi, Claudia Martini, Maria C Breschi, Vladimir E Kataev, Vincenzo Calderone. Mitochondriotropic and Cardioprotective Effects of Triphenylphosphonium-Conjugated Derivatives of the Diterpenoid Isosteviol. International journal of molecular sciences. 2017 Sep; 18(10):. doi: 10.3390/ijms18102060. [PMID: 28954424]
  • Julian P Wald, Gertrud E Morlock. Quantification of steviol glycosides in food products, Stevia leaves and formulations by planar chromatography, including proof of absence for steviol and isosteviol. Journal of chromatography. A. 2017 Jul; 1506(?):109-119. doi: 10.1016/j.chroma.2017.05.026. [PMID: 28552425]
  • Dinar R Gabdrakhmanov, Mikhail A Voronin, Lucia Ya Zakharova, Alexander I Konovalov, Ravil N Khaybullin, Irina Yu Strobykina, Vladimir E Kataev, Dzhigangir A Faizullin, Natalia E Gogoleva, Tatiana A Konnova, Vadim V Salnikov, Yuriy F Zuev. Supramolecular design of biocompatible nanocontainers based on amphiphilic derivatives of a natural compound isosteviol. Physical chemistry chemical physics : PCCP. 2013 Oct; 15(39):16725-35. doi: 10.1039/c3cp51511g. [PMID: 23985972]
  • Sreemanti Das, Jayeeta Das, Asmita Samadder, Anisur Rahman Khuda-Bukhsh. Dihydroxy-isosteviol methyl ester from Pulsatilla nigricans induces apoptosis in HeLa cells: its cytoxicity and interaction with calf thymus DNA. Phytotherapy research : PTR. 2013 May; 27(5):664-71. doi: 10.1002/ptr.4768. [PMID: 22744955]
  • Deyi Xu, Min Xu, Lin Lin, Shasha Rao, Jiping Wang, Andrew K Davey. The effect of isosteviol on hyperglycemia and dyslipidemia induced by lipotoxicity in rats fed with high-fat emulsion. Life sciences. 2012 Jan; 90(1-2):30-8. doi: 10.1016/j.lfs.2011.10.010. [PMID: 22075495]
  • V E Kataev, I Iu Strobykina, O V Andreeva, B F Garifullin, R R Sharipova, V F Mironov, R V Chestnova. [Synthesis and antituberculosis activity of the derivatives of glycoside steviolbioside from the plant Stevia rebaudiana and diterpenoid isosteviol containing hydrazone, hydrazide and pyridinoyl moieties]. Bioorganicheskaia khimiia. 2011 Jul; 37(4):542-51. doi: 10.1134/s1068162011030095. [PMID: 22096997]
  • Hongping Jin, Jacobus P Gerber, Jiping Wang, Min Ji, Andrew K Davey. Oral and i.v. pharmacokinetics of isosteviol in rats as assessed by a new sensitive LC-MS/MS method. Journal of pharmaceutical and biomedical analysis. 2008 Nov; 48(3):986-90. doi: 10.1016/j.jpba.2008.06.015. [PMID: 18701231]
  • I Nordentoft, P B Jeppesen, J Hong, R Abudula, K Hermansen. Isosteviol increases insulin sensitivity and changes gene expression of key insulin regulatory genes and transcription factors in islets of the diabetic KKAy mouse. Diabetes, obesity & metabolism. 2008 Sep; 10(10):939-49. doi: 10.1111/j.1463-1326.2007.00836.x. [PMID: 18201205]
  • Deyi Xu, Wenfeng Du, Lei Zhao, Andrew K Davey, Jiping Wang. The neuroprotective effects of isosteviol against focal cerebral ischemia injury induced by middle cerebral artery occlusion in rats. Planta medica. 2008 Jun; 74(8):816-21. doi: 10.1055/s-2008-1074557. [PMID: 18553271]
  • J Ma, Z Ma, J Wang, R W Milne, D Xu, A K Davey, A M Evans. Isosteviol reduces plasma glucose levels in the intravenous glucose tolerance test in Zucker diabetic fatty rats. Diabetes, obesity & metabolism. 2007 Jul; 9(4):597-9. doi: 10.1111/j.1463-1326.2006.00630.x. [PMID: 17587403]
  • Deyi Xu, Yongfang Li, Jiping Wang, Andrew K Davey, Shuangjie Zhang, Allan M Evans. The cardioprotective effect of isosteviol on rats with heart ischemia-reperfusion injury. Life sciences. 2007 Jan; 80(4):269-74. doi: 10.1016/j.lfs.2006.09.008. [PMID: 17055001]