Yangonin (BioDeep_00000000418)

   

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid .gamma.-lactone

化学式: C15H14O4 (258.0892044)
中文名称: 甲氧醉椒素, 麻醉椒素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 6.52%

分子结构信息

SMILES: COC1=CC=C(C=C1)C=CC2=CC(=CC(=O)O2)OC
InChI: InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+

描述信息

Yangonin is a member of 2-pyranones and an aromatic ether.
Yangonin is a natural product found in Piper methysticum, Ranunculus silerifolius, and Piper majusculum with data available.
See also: Piper methysticum root (part of).
Yangonin is found in beverages. Yangonin is found in kava root (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002).
Found in kava root (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
Yangonin exhibits affinity for the human recombinant cannabinoid CB1 receptor with an IC50 and a Ki of 1.79 μM and 0.72 μM, respectively.
Yangonin exhibits affinity for the human recombinant cannabinoid CB1 receptor with an IC50 and a Ki of 1.79 μM and 0.72 μM, respectively.

同义名列表

29 个代谢物同义名

5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid .gamma.-lactone; 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid gamma-lactone; 2H-Pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)-; 2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)-; 2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-; 2H-PYRAN-2-ONE, 4-METHOXY-6-((1E)-2-(4-METHOXYPHENYL)ETHENYL)-; 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one #; 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one, 9CI; 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one; (E)-4-Methoxy-6-[2-(4-Methoxyphenyl)Ethenyl]Pyran-2-one; 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-METHOXY-6-((E)-2-(4-METHOXYPHENYL)ETHENYL)PYRAN-2-ONE; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2-pyranone; 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]pyran-2-one; 4-Methoxy-6-(.beta.-(p-anisyl)vinyl)-.alpha.-pyrone; (E)-4-Methoxy-6-(4-methoxystyryl)-2H-pyran-2-one; 4-Methoxy-6-(beta-(p-anisyl)vinyl)-alpha-pyrone; 2H-PYRAN-2-ONE, 4-METHOXY-6-(p-METHOXYSTYRYL)-; 4-Methoxy-6-(p-methoxystyryl)-2H-pyran-2-one; 4-Methoxy-6-(4-methoxystyryl)-a-pyrone; Yangonin, analytical standard; XLHIYUYCSMZCCC-VMPITWQZSA-N; YANGONIN [MI]; Methoxyxerin; Tox21_202547; Yangonin; Demethoxyyangonin;5,6-Dehydrokavain



数据库引用编号

20 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)

47 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

  • 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]
  • Philip W Melchert, Yuli Qian, Qingchen Zhang, Brandon O Klee, Chengguo Xing, John S Markowitz. In vitro inhibition of carboxylesterase 1 by Kava (Piper methysticum) Kavalactones. Chemico-biological interactions. 2022 Apr; 357(?):109883. doi: 10.1016/j.cbi.2022.109883. [PMID: 35278473]
  • Lina Kong, Renchao Dong, Kai Huang, Xiaohui Wang, Dalong Wang, Nan Yue, Changyuan Wang, Pengyuan Sun, Jiangning Gu, Haifeng Luo, Kexin Liu, Jingjing Wu, Huijun Sun, Qiang Meng. Yangonin modulates lipid homeostasis, ameliorates cholestasis and cellular senescence in alcoholic liver disease via activating nuclear receptor FXR. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Sep; 90(?):153629. doi: 10.1016/j.phymed.2021.153629. [PMID: 34304130]
  • Antonio Celentano, Callisthenis Yiannis, Rita Paolini, Pangzhen Zhang, Camile S Farah, Nicola Cirillo, Tami Yap, Michael McCullough. Kava constituents exert selective anticancer effects in oral squamous cell carcinoma cells in vitro. Scientific reports. 2020 09; 10(1):15904. doi: 10.1038/s41598-020-73058-4. [PMID: 32985597]
  • Callisthenis Yiannis, Kevin Huang, An Nhien Tran, Cathy Zeng, Emily Dao, Oliver Baselyous, Muaaz Adil Mithwani, Rita Paolini, Nicola Cirillo, Tami Yap, Michael McCullough, Antonio Celentano. Protective effect of kava constituents in an in vitro model of oral mucositis. Journal of cancer research and clinical oncology. 2020 Jul; 146(7):1801-1811. doi: 10.1007/s00432-020-03253-3. [PMID: 32435894]
  • Jonna Berry, Ashley Gilbert, Justin Grodnitzky. Cases of Kava Impairment in Iowa Drivers. Journal of forensic sciences. 2019 Nov; 64(6):1943-1949. doi: 10.1111/1556-4029.14130. [PMID: 31305953]
  • Xiaohui Wang, Ting Fu, Junqiao Wang, Changyuan Wang, Kexin Liu, Jingjing Wu, Huijun Sun, Xiaodong Ma, Pengyuan Sun, Qiang Meng. Hepatoprotection of yangonin against hepatic fibrosis in mice via farnesoid X receptor activation. International immunopharmacology. 2019 Oct; 75(?):105833. doi: 10.1016/j.intimp.2019.105833. [PMID: 31450152]
  • H M P Dilrukshi Herath, Sarah Preston, Abdul Jabbar, Jose Garcia-Bustos, Russell S Addison, Sasha Hayes, Topul Rali, Tao Wang, Anson V Koehler, Bill C H Chang, Andreas Hofmann, Rohan A Davis, Robin B Gasser. Selected α-pyrones from the plants Cryptocarya novoguineensis (Lauraceae) and Piper methysticum (Piperaceae) with activity against Haemonchus contortus in vitro. International journal for parasitology. Drugs and drug resistance. 2019 04; 9(?):72-79. doi: 10.1016/j.ijpddr.2018.12.006. [PMID: 30739078]
  • Renchao Dong, Xiaobo Yang, Changyuan Wang, Kexin Liu, Zhihao Liu, Xiaodong Ma, Huijun Sun, Xiaokui Huo, Ting Fu, Qiang Meng. Yangonin protects against non-alcoholic fatty liver disease through farnesoid X receptor. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Feb; 53(?):134-142. doi: 10.1016/j.phymed.2018.09.006. [PMID: 30668392]
  • Ying Liu, Jensen A Lund, Susan J Murch, Paula N Brown. Single-Lab Validation for Determination of Kavalactones and Flavokavains in Piper methysticum (Kava). Planta medica. 2018 Nov; 84(16):1213-1218. doi: 10.1055/a-0637-2400. [PMID: 29940660]
  • Adele Murauer, Markus Ganzera. Quantitative Determination of Lactones in Piper methysticum (Kava-Kava) by Supercritical Fluid Chromatography. Planta medica. 2017 Aug; 83(12-13):1053-1057. doi: 10.1055/s-0043-100632. [PMID: 28095587]
  • Alessia Ligresti, Rosaria Villano, Marco Allarà, István Ujváry, Vincenzo Di Marzo. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand. Pharmacological research. 2012 Aug; 66(2):163-9. doi: 10.1016/j.phrs.2012.04.003. [PMID: 22525682]
  • Xuesen Li, Zhongbo Liu, Xia Xu, Christopher A Blair, Zheng Sun, Jun Xie, Michael B Lilly, Xiaolin Zi. Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in mice. PloS one. 2012; 7(2):e31213. doi: 10.1371/journal.pone.0031213. [PMID: 22347450]
  • Yan Li, Hu Mei, Qiangen Wu, Suhui Zhang, Jia-Long Fang, Leming Shi, Lei Guo. Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicological sciences : an official journal of the Society of Toxicology. 2011 Dec; 124(2):388-99. doi: 10.1093/toxsci/kfr235. [PMID: 21908763]
  • Rolf Teschke, Vincent Lebot. Proposal for a kava quality standardization code. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Oct; 49(10):2503-16. doi: 10.1016/j.fct.2011.06.075. [PMID: 21756963]
  • Yuma Iwai, Kouki Murakami, Yasuyuki Gomi, Toshihiro Hashimoto, Yoshinori Asakawa, Yoshinobu Okuno, Toyokazu Ishikawa, Dai Hatakeyama, Noriko Echigo, Takashi Kuzuhara. Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts. PloS one. 2011; 6(5):e19825. doi: 10.1371/journal.pone.0019825. [PMID: 21625478]
  • Valerie Robinson, Wilma F Bergfeld, Donald V Belsito, Curtis D Klaassen, James G Marks, Ronald C Shank, Thomas J Slaga, Paul W Snyder, F Alan Andersen. Final report on the safety assessment of Piper methysticum leaf/root/stem extract and Piper methysticum root extract. International journal of toxicology. 2009 Nov; 28(6 Suppl):175S-88S. doi: 10.1177/1091581809350934. [PMID: 19966149]
  • Paul Whittaker, Jane J Clarke, Richard H C San, Joseph M Betz, Harold E Seifried, Lowri S de Jager, Virginia C Dunkel. Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2008 Jan; 46(1):168-74. doi: 10.1016/j.fct.2007.07.013. [PMID: 17822821]
  • A Matthias, J T Blanchfield, K G Penman, K M Bone, I Toth, R P Lehmann. Permeability studies of Kavalactones using a Caco-2 cell monolayer model. Journal of clinical pharmacy and therapeutics. 2007 Jun; 32(3):233-9. doi: 10.1111/j.1365-2710.2007.00810.x. [PMID: 17489874]
  • Hideaki Matsuda, Noriko Hirata, Yoshiko Kawaguchi, Shunsuke Naruto, Takanobu Takata, Masayoshi Oyama, Munekazu Iinuma, Michinori Kubo. Melanogenesis stimulation in murine B16 melanoma cells by Kava (Piper methysticum) rhizome extract and kavalactones. Biological & pharmaceutical bulletin. 2006 Apr; 29(4):834-7. doi: 10.1248/bpb.29.834. [PMID: 16595931]
  • T D Xuan, A A Elzaawely, M Fukuta, S Tawata. Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum). Journal of agricultural and food chemistry. 2006 Feb; 54(3):720-5. doi: 10.1021/jf0519461. [PMID: 16448174]
  • J Anke, S Fu, I Ramzan. Kavalactones fail to inhibit alcohol dehydrogenase in vitro. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006 Feb; 13(3):192-5. doi: 10.1016/j.phymed.2004.07.005. [PMID: 16428028]
  • Emma Warburton, Tony Bristow. Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation. European journal of mass spectrometry (Chichester, England). 2006; 12(4):223-33. doi: 10.1255/ejms.808. [PMID: 17057279]
  • Johanna Weiss, Alexandra Sauer, Andreas Frank, Matthias Unger. Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug metabolism and disposition: the biological fate of chemicals. 2005 Nov; 33(11):1580-3. doi: 10.1124/dmd.105.005892. [PMID: 16051732]
  • Orapin Chienthavorn, Roger M Smith, Ian D Wilson, Brian Wright, Eva M Lenz. Superheated water chromatography-nuclear magnetic resonance spectroscopy of kava lactones. Phytochemical analysis : PCA. 2005 May; 16(3):217-21. doi: 10.1002/pca.848. [PMID: 15997856]
  • Lihong Hu, Jin-Woo Jhoo, Catharina Y W Ang, Michael Dinovi, Antonia Mattia. Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. Journal of AOAC International. 2005 Jan; 88(1):16-25. doi: . [PMID: 15759721]
  • Yuzhong Ma, Karuna Sachdeva, Jirong Liu, Michael Ford, Dongfang Yang, Ikhlas A Khan, Clinton O Chichester, Bingfang Yan. Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug metabolism and disposition: the biological fate of chemicals. 2004 Nov; 32(11):1317-24. doi: 10.1124/dmd.104.000786. [PMID: 15282211]
  • L S de Jager, G A Perfetti, G W Diachenko. LC-UV and LC-MS analysis of food and drink products containing kava. Food additives and contaminants. 2004 Oct; 21(10):921-34. doi: 10.1080/02652030400010454. [PMID: 15712517]
  • Pratibha V Nerurkar, Klaus Dragull, Chung-Shih Tang. In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones. Toxicological sciences : an official journal of the Society of Toxicology. 2004 May; 79(1):106-11. doi: 10.1093/toxsci/kfh067. [PMID: 14737001]
  • Lihong Zou, Martha R Harkey, Gary L Henderson, Laura E Dike. Kava does not display metabolic toxicity in a homogeneous cellular assay. Planta medica. 2004 Apr; 70(4):289-92. doi: 10.1055/s-2004-818937. [PMID: 15095141]
  • L Zou, G L Henderson, M R Harkey, Y Sakai, A Li. Effects of kava (Kava-kava, 'Awa, Yaqona, Piper methysticum) on c-DNA-expressed cytochrome P450 enzymes and human cryopreserved hepatocytes. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2004; 11(4):285-94. doi: 10.1078/0944711041495263. [PMID: 15185840]
  • T Hashimoto, M Suganuma, H Fujiki, M Yamada, T Kohno, Y Asakawa. Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum). Phytomedicine : international journal of phytotherapy and phytopharmacology. 2003 May; 10(4):309-17. doi: 10.1078/094471103322004802. [PMID: 12809361]
  • L Zou, M R Harkey, G L Henderson. Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2002 Apr; 9(3):263-7. doi: 10.1078/0944-7113-00121. [PMID: 12046870]
  • D Wu, L Yu, M G Nair, D L DeWitt, R S Ramsewak. Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2002 Jan; 9(1):41-7. doi: 10.1078/0944-7113-00068. [PMID: 11924763]
  • A Avdeef, M Strafford, E Block, M P Balogh, W Chambliss, I Khan. Drug absorption in vitro model: filter-immobilized artificial membranes. 2. Studies of the permeability properties of lactones in Piper methysticum Forst. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2001 Dec; 14(4):271-80. doi: 10.1016/s0928-0987(01)00191-9. [PMID: 11684401]
  • L D Dinh, U Simmen, K B Bueter, B Bueter, K Lundstrom, W Schaffner. Interaction of various Piper methysticum cultivars with CNS receptors in vitro. Planta medica. 2001 Jun; 67(4):306-11. doi: 10.1055/s-2001-14334. [PMID: 11458444]
  • G Boonen, M A Beck, H Häberlein. Contribution to the quantitative and enantioselective determination of kavapyrones by high-performance liquid chromatography on ChiraSpher NT material. Journal of chromatography. B, Biomedical sciences and applications. 1997 Nov; 702(1-2):240-4. doi: 10.1016/s0378-4347(97)00389-7. [PMID: 9449578]
  • J Harkness. Why urinalysis?. The Central African journal of medicine. 1975 Aug; 21(8):178-83. doi: NULL. [PMID: 1150]