8-Epixanthatin (BioDeep_00000000472)

 

Secondary id: BioDeep_00001867507

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2H-CYCLOHEPTA(B)FURAN-2-ONE, 3,3A,4,7,8,8A-HEXAHYDRO-7-METHYL-3-METHYLENE-6-((1E)-3-OXO-1-BUTEN-1-YL)-, (3AR,7S,8AS)-

化学式: C15H18O3 (246.1255878)
中文名称: 叶黄制菌素, 苍耳亭
谱图信息: 最多检出来源 Escherichia coli(natural_products) 45.83%

分子结构信息

SMILES: C=C1C(=O)OC2CC(C)C(C=CC(C)=O)=CCC12
InChI: InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3

描述信息

Xanthatin is a sesquiterpene lactone.
Xanthatin is a natural product found in Xanthium spinosum, Dittrichia graveolens, and other organisms with data available.
8-Epixanthatin is found in fats and oils. 8-Epixanthatin is a constituent of Helianthus annuus (sunflower).
Constituent of Helianthus annuus (sunflower). 8-Epixanthatin is found in fats and oils.
D000970 - Antineoplastic Agents

同义名列表

14 个代谢物同义名

2H-CYCLOHEPTA(B)FURAN-2-ONE, 3,3A,4,7,8,8A-HEXAHYDRO-7-METHYL-3-METHYLENE-6-((1E)-3-OXO-1-BUTEN-1-YL)-, (3AR,7S,8AS)-; (3aR,7S,8aS)-7-Methyl-3-methylene-6-((E)-3-oxobut-1-en-1-yl)-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-one; (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(1E)-3-oxobut-1-en-1-yl]-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one; (3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one; 7-methyl-3-methylidene-6-[(1Z)-3-oxobut-1-en-1-yl]-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one; 3,3a,4,7,8,8a-Hexahydro-7-methyl-3-methylene-6-(3-oxo-1-butenyl)-2H-cyclohepta(b)furan-2-one; 7-methyl-3-methylidene-6-[(1Z)-3-oxobut-1-en-1-yl]-3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one; XANTHATIN, (-)-; 8-epi-xanthatin; XANTHATIN [MI]; 8-Epixanthatin; Xanthatin (2); (-)-Xanthatin; Xanthatin



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)

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

  • Yadi Geng, Ping Liu, Yanbo Xie, Yunxiao Liu, Xinge Zhang, Xingcun Hou, Lei Zhang. Xanthatin suppresses pancreatic cancer cell growth via the ROS/RBL1 signaling pathway: In vitro and in vivo insights. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Aug; 119(?):155004. doi: 10.1016/j.phymed.2023.155004. [PMID: 37562091]
  • Chun Yang, Yang Li, Yuan Zhang, Qiang Hu, Ying Liu, Yang-Fan Li, Hong-Cheng Shi, Li-Li Song, Hui Cao, Xiao-Juan Hao, Xiao-Yan Zhi. Natural Sesquiterpene Lactone as Source of Discovery of Novel Fungicidal Candidates: Structural Modification and Antifungal Activity Evaluation of Xanthatin Derived from Xanthium strumarium L. Journal of agricultural and food chemistry. 2023 Jul; ?(?):. doi: 10.1021/acs.jafc.3c02435. [PMID: 37449982]
  • Yadi Geng, Lingli Li, Ping Liu, Zhaolin Chen, Aizong Shen, Lei Zhang. TMT-Based Quantitative Proteomic Analysis Identified Proteins and Signaling Pathways Involved in the Response to Xanthatin Treatment in Human HT-29 Colon Cancer Cells. Anti-cancer agents in medicinal chemistry. 2022; 22(5):887-896. doi: 10.2174/1871520621666210901101510. [PMID: 34488591]
  • Xiao-Yan Zhi, Li-Li Song, Jing Liang, Si-Qi Wei, Yang Li, Yuan Zhang, Xiao-Juan Hao, Hui Cao, Chun Yang. Synthesis and in vitro antifungal activity of new Michael-type amino derivatives of xanthatin, a natural sesquiterpene lactone from Xanthium strumarium L. Bioorganic & medicinal chemistry letters. 2022 01; 55(?):128481. doi: 10.1016/j.bmcl.2021.128481. [PMID: 34852242]
  • Yuan He, Dongyu Lei, Qingqing Yang, Hao Qi, Kurax Almira, Dilnigar Askar, Lu Jin, Le Pan. X anthium Orientale subsp. Italicum (Moretti) Greuter: bioassay-guided isolation and its chemical basis of antitumor cytotoxicity. Natural product research. 2021 Jul; 35(14):2433-2437. doi: 10.1080/14786419.2019.1672686. [PMID: 31631691]
  • Mariano Ezequiel Vera, María Laura Mariani, Cristina Aguilera, Alicia Beatriz Penissi. Effect of a Cytoprotective Dose of Dehydroleucodine, Xanthatin, and 3-Benzyloxymethyl-5H-furan-2-one on Gastric Mucosal Lesions Induced by Mast Cell Activation. International journal of molecular sciences. 2021 Jun; 22(11):. doi: 10.3390/ijms22115983. [PMID: 34205991]
  • Jian Zhang, Sheng Yang, Hongmei Guan, Jueyu Zhou, Yuan Gao. Xanthatin synergizes with cisplatin to suppress homologous recombination through JAK2/STAT4/BARD1 axis in human NSCLC cells. Journal of cellular and molecular medicine. 2021 02; 25(3):1688-1699. doi: 10.1111/jcmm.16271. [PMID: 33439503]
  • Ya-di Geng, Lei Zhang, Guo-Yu Wang, Xiao-Jun Feng, Zhao-Lin Chen, Ling Jiang, Ai-Zong Shen. Xanthatin mediates G2/M cell cycle arrest, autophagy and apoptosis via ROS/XIAP signaling in human colon cancer cells. Natural product research. 2020 Sep; 34(18):2616-2620. doi: 10.1080/14786419.2018.1544976. [PMID: 30587055]
  • Xiao-Yan Zhi, Ling-Yun Jiang, Ting Li, Li-Li Song, Li-Juan Wu, Hui Cao, Chun Yang. Natural product-based semisynthesis and biological evaluation of thiol/amino-Michael adducts of xanthatin derived from Xanthium strumarium as potential pesticidal agents. Bioorganic chemistry. 2020 04; 97(?):103696. doi: 10.1016/j.bioorg.2020.103696. [PMID: 32135360]
  • Xue Zheng, Chao Sun, Rilei Yu, Xin Chu, Jiahao Xu, Chengcheng Liu, Miaoqing Zhao, Xuelian Xu, Ming Xia, Cheng Wang. CD13-specific ligand facilitates Xanthatin nanomedicine targeting dendritic cells for therapy of refractory allergic rhinitis. International journal of pharmaceutics. 2020 Mar; 577(?):119034. doi: 10.1016/j.ijpharm.2020.119034. [PMID: 31991183]
  • Yaqian Zhou, Xingyu Zhu, Shangyang Lin, Chenqi Zhu, Li Wu, Rui Chen, Zhipeng Chen, Weidong Li. A Novel Nanoparticle Preparation to Enhance the Gastric Adhesion and Bioavailability of Xanthatin. International journal of nanomedicine. 2020; 15(?):5073-5082. doi: 10.2147/ijn.s252049. [PMID: 32764937]
  • Man Liu, Cheng-Qian Xiao, Ming-Wei Sun, Min-Jia Tan, Li-Hong Hu, Qiang Yu. Xanthatin inhibits STAT3 and NF-κB signalling by covalently binding to JAK and IKK kinases. Journal of cellular and molecular medicine. 2019 06; 23(6):4301-4312. doi: 10.1111/jcmm.14322. [PMID: 30993883]
  • Janet Piloto-Ferrer, Ángel Sánchez-Lamar, Marbelis Francisco, Maria L González, Nelsón Merino, Guillermo Aparicio, Carlos Pérez, Idania Rodeiro, Miriam Teresa Paz Lopes. Xanthium strumarium´s xanthatins induces mitotic arrest and apoptosis in CT26WT colon carcinoma cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Apr; 57(?):236-244. doi: 10.1016/j.phymed.2018.12.019. [PMID: 30797985]
  • Xin-Yi Fang, Hai Zhang, Lin Zhao, Shuai Tan, Qing-Cuo Ren, Lun Wang, Xiao-Fei Shen. A new xanthatin analogue 1β-hydroxyl-5α-chloro-8-epi-xanthatin induces apoptosis through ROS-mediated ERK/p38 MAPK activation and JAK2/STAT3 inhibition in human hepatocellular carcinoma. Biochimie. 2018 Sep; 152(?):43-52. doi: 10.1016/j.biochi.2018.06.018. [PMID: 29960031]
  • Angel Sánchez-Lamar, Janet Piloto-Ferrer, Mario Fiore, Pasquale Stano, Renata Cozzi, Daniela Tofani, Enrico Cundari, Marbelis Francisco, Aylema Romero, Maria L González, Francesca Degrassi. Xanthium strumarium extract inhibits mammalian cell proliferation through mitotic spindle disruption mediated by xanthatin. Journal of ethnopharmacology. 2016 Dec; 194(?):781-788. doi: 10.1016/j.jep.2016.11.006. [PMID: 27840259]
  • Li Tao, Xiaobo Sheng, Lei Zhang, Weidong Li, Zhonghong Wei, Pinting Zhu, Feng Zhang, Aiyun Wang, James R Woodgett, Yin Lu. Xanthatin anti-tumor cytotoxicity is mediated via glycogen synthase kinase-3β and β-catenin. Biochemical pharmacology. 2016 09; 115(?):18-27. doi: 10.1016/j.bcp.2016.06.009. [PMID: 27321043]
  • Hai Shang, Junhua Liu, Ruiyang Bao, Yu Cao, Kun Zhao, Chengqian Xiao, Bing Zhou, Lihong Hu, Yefeng Tang. Biomimetic synthesis: discovery of xanthanolide dimers. Angewandte Chemie (International ed. in English). 2014 Dec; 53(52):14494-8. doi: 10.1002/anie.201406461. [PMID: 25430055]
  • Cuiping Yan, Huan Li, Yu Wu, Donghao Xie, Zebin Weng, Baochang Cai, Xiao Liu, Weidong Li, Zhipeng Chen. Determination of xanthatin by ultra high performance liquid chromatography coupled with triple quadrupole mass spectrometry: application to pharmacokinetic study of xanthatin in rat plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Feb; 947-948(?):57-61. doi: 10.1016/j.jchromb.2013.12.006. [PMID: 24389355]
  • Shuso Takeda, Momoko Noguchi, Kazumasa Matsuo, Yasuhiro Yamaguchi, Taichi Kudo, Hajime Nishimura, Yoshiko Okamoto, Toshiaki Amamoto, Mitsuru Shindo, Curtis J Omiecinski, Hironori Aramaki. (-)-Xanthatin up-regulation of the GADD45γ tumor suppressor gene in MDA-MB-231 breast cancer cells: role of topoisomerase IIα inhibition and reactive oxygen species. Toxicology. 2013 Mar; 305(?):1-9. doi: 10.1016/j.tox.2012.12.019. [PMID: 23313378]
  • Shuso Takeda, Hajime Nishimura, Kuniyoshi Koyachi, Kenji Matsumoto, Kazutaka Yoshida, Yoshiko Okamoto, Toshiaki Amamoto, Mitsuru Shindo, Hironori Aramaki. (-)-Xanthatin induces the prolonged expression of c-Fos through an N-acetyl-L-cysteine (NAC)-sensitive mechanism in human breast cancer MDA-MB-231 cells. The Journal of toxicological sciences. 2013; 38(4):547-57. doi: 10.2131/jts.38.547. [PMID: 23824011]
  • Fangfang Chen, Fuhua Hao, Changfu Li, Junbo Gou, Dayan Lu, Fujun Gong, Huiru Tang, Yansheng Zhang. Identifying three ecological chemotypes of Xanthium strumarium glandular trichomes using a combined NMR and LC-MS method. PloS one. 2013; 8(10):e76621. doi: 10.1371/journal.pone.0076621. [PMID: 24098541]
  • Endalkachew Nibret, Mahamoud Youns, R Luise Krauth-Siegel, Michael Wink. Biological activities of xanthatin from Xanthium strumarium leaves. Phytotherapy research : PTR. 2011 Dec; 25(12):1883-90. doi: 10.1002/ptr.3651. [PMID: 21953905]
  • Benoit Pinel, Joëlle Dubois, Denis Séraphin, Pascal Richomme. Semisynthesis of alpha-methyl-gamma-lactones and in vitro evaluation of their activity on protein farnesyltransferase. Journal of enzyme inhibition and medicinal chemistry. 2010 Apr; 25(2):172-9. doi: 10.3109/14756360903169592. [PMID: 20222761]
  • Irving Ramírez-Erosa, Yaoge Huang, Robert A Hickie, Ronald G Sutherland, Branka Barl. Xanthatin and xanthinosin from the burs of Xanthium strumarium L. as potential anticancer agents. Canadian journal of physiology and pharmacology. 2007 Nov; 85(11):1160-72. doi: 10.1139/y07-104. [PMID: 18066118]
  • Y Sato, H Oketani, T Yamada, K Singyouchi, T Ohtsubo, M Kihara, H Shibata, T Higuti. A xanthanolide with potent antibacterial activity against methicillin-resistant Staphylococcus aureus. The Journal of pharmacy and pharmacology. 1997 Oct; 49(10):1042-4. doi: 10.1111/j.2042-7158.1997.tb06038.x. [PMID: 9364417]
  • C Roussakis, I Chinou, C Vayas, C Harvala, J F Verbist. Cytotoxic activity of xanthatin and the crude extracts of Xanthium strumarium. Planta medica. 1994 Oct; 60(5):473-4. doi: 10.1055/s-2006-959537. [PMID: 7997481]