germacron (BioDeep_00000860066)

Main id: BioDeep_00000000024

 

PANOMIX_OTCML-2023


代谢物信息卡片


3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)-

化学式: C15H22O (218.1670562)
中文名称: 吉马酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CCC(=C(C)C)C(=O)CC(=CCC1)C
InChI: InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+

描述信息

Germacrone is extracted from Rhizoma Curcuma. Germacrone inhibits influenza virus infection[1].
Germacrone is extracted from Rhizoma Curcuma. Germacrone inhibits influenza virus infection[1].

同义名列表

8 个代谢物同义名

3,7-Cyclodecadien-1-one, 3,7-dimethyl-10-(1-methylethylidene)-, (E,E)-; (3E,7E)-3,7-dimethyl-10-propan-2-ylidene-cyclodeca-3,7-dien-1-one; (3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one; (3E,7E)-10-isopropylidene-3,7-dimethyl-cyclodeca-3,7-dien-1-one; (3E,7E)-10-isopropylidene-3,7-dimethyl-1-cyclodeca-3,7-dienone; Germacrone; germacron; 6902-91-6



数据库引用编号

8 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)

79 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

  • Yunguang Wang, Xinxin He, Mengjiao Xue, Huan Yu, Qiang He, Juan Jin. Integrated 16S rRNA sequencing and metabolomic analysis reveals the potential protective mechanism of Germacrone on diabetic nephropathy in mice. Acta biochimica et biophysica Sinica. 2024 03; 56(3):414-426. doi: 10.3724/abbs.2024021. [PMID: 38429975]
  • Yunguang Wang, Xinxin He, Mengjiao Xue, Wenbo Sun, Qiang He, Juan Jin. Germacrone protects renal tubular cells against ferroptotic death and ROS release by re-activating mitophagy in diabetic nephropathy. Free radical research. 2023 Oct; ?(?):1-17. doi: 10.1080/10715762.2023.2277143. [PMID: 37897414]
  • Guanhua Lou, Yan Huang, Yu Wang, Shiyun Chen, Chang Liu, Ying Li, Jianan Feng. Germacrone, a novel and safe anticancer agent from genus curcuma : a review of its mechanism. Anti-cancer agents in medicinal chemistry. 2023 Apr; ?(?):. doi: 10.2174/1871520623666230420094628. [PMID: 37139672]
  • Tingfei Tan, Qi Huang, Weiwei Chu, Bo Li, Jingjing Wu, Quan Xia, Xi Cao. Delivery of germacrone (GER) using macrophages-targeted polymeric nanoparticles and its application in rheumatoid arthritis. Drug delivery. 2022 Dec; 29(1):692-701. doi: 10.1080/10717544.2022.2044936. [PMID: 35225122]
  • Juan Jin, Yunguang Wang, Danna Zheng, Mingzhu Liang, Qiang He. A Novel Identified Circular RNA, mmu_mmu_circRNA_0000309, Involves in Germacrone-Mediated Improvement of Diabetic Nephropathy Through Regulating Ferroptosis by Targeting miR-188-3p/GPX4 Signaling Axis. Antioxidants & redox signaling. 2022 04; 36(10-12):740-759. doi: 10.1089/ars.2021.0063. [PMID: 34913724]
  • Didjour Albert Kambiré, Jean Brice Boti, Zana Adama Ouattara, Acafou Yapi Thierry, Nelly Barat, Ange Bighelli, Félix Tomi. Chemical composition of root and stem bark essential oils from Ivorian Isolona dewevrei: structural elucidation of a new natural germacrone. Natural product research. 2022 Apr; 36(8):2105-2111. doi: 10.1080/14786419.2020.1851219. [PMID: 33565887]
  • De Ji, Qi Zhao, Yuwen Qin, Huangjin Tong, Qiaohan Wang, Mengting Yu, Chunqin Mao, Tulin Lu, Jinchun Qiu, Chengxi Jiang. Germacrone improves liver fibrosis by regulating the PI3K/AKT/mTOR signalling pathway. Cell biology international. 2021 Sep; 45(9):1866-1875. doi: 10.1002/cbin.11607. [PMID: 33835632]
  • Yang Zhao, Jie Cai, Kaihu Shi, Hang Li, Jin Du, Dinghui Hu, Zuntao Liu, Wei Wang. Germacrone induces lung cancer cell apoptosis and cell cycle arrest via the Akt/MDM2/p53 signaling pathway. Molecular medicine reports. 2021 06; 23(6):. doi: 10.3892/mmr.2021.12091. [PMID: 33880579]
  • Sujing Zhuang, Baogui Liu, Shifeng Guo, Yanzhong Xue, Lin Wu, Shiqi Liu, Chunling Zhang, Xiuyan Ni. Germacrone alleviates neurological deficits following traumatic brain injury by modulating neuroinflammation and oxidative stress. BMC complementary medicine and therapies. 2021 Jan; 21(1):6. doi: 10.1186/s12906-020-03175-0. [PMID: 33402180]
  • De Ji, Qiaohan Wang, Qi Zhao, Huangjin Tong, Mengting Yu, Meng Wang, Tulin Lu, Chengxi Jiang. Co-delivery of miR-29b and germacrone based on cyclic RGD-modified nanoparticles for liver fibrosis therapy. Journal of nanobiotechnology. 2020 Jun; 18(1):86. doi: 10.1186/s12951-020-00645-y. [PMID: 32513194]
  • Tomáš Zárybnický, Petra Matoušková, Lenka Skálová, Iva Boušová. The Hepatotoxicity of Alantolactone and Germacrone: Their Influence on Cholesterol and Lipid Metabolism in Differentiated HepaRG Cells. Nutrients. 2020 Jun; 12(6):. doi: 10.3390/nu12061720. [PMID: 32521813]
  • Ling Li, Qing Xie, Gang Bian, Biyan Zhang, Mengfei Wang, Yanping Wang, Zijun Chen, Yunsen Li. Anti-H1N1 viral activity of three main active ingredients from zedoary oil. Fitoterapia. 2020 Apr; 142(?):104489. doi: 10.1016/j.fitote.2020.104489. [PMID: 32004654]
  • Ren Zhang, Ji Hao, Kaiwen Guo, Wanxin Liu, Fei Yao, Qingming Wu, Chang Liu, Qiang Wang, Xinzhou Yang. Germacrone Inhibits Cell Proliferation and Induces Apoptosis in Human Esophageal Squamous Cell Carcinoma Cells. BioMed research international. 2020; 2020(?):7643248. doi: 10.1155/2020/7643248. [PMID: 32071920]
  • Sirima Soodvilai, Paranee Meetam, Lawan Siangjong, Ratchanaporn Chokchaisiri, Apichart Suksamrarn, Sunhapas Soodvilai. Germacrone Reduces Cisplatin-Induced Toxicity of Renal Proximal Tubular Cells via Inhibition of Organic Cation Transporter. Biological & pharmaceutical bulletin. 2020; 43(11):1693-1698. doi: 10.1248/bpb.b20-00392. [PMID: 33132314]
  • Zongru Wang, Feng Zhuo, Peigang Chu, Xiaoli Yang, Gang Zhao. Germacrone alleviates collagen-induced arthritis via regulating Th1/Th2 balance and NF-κB activation. Biochemical and biophysical research communications. 2019 10; 518(3):560-564. doi: 10.1016/j.bbrc.2019.08.084. [PMID: 31451221]
  • Xuefeng Hou, Beibei Cao, Yuanzhi He, Teng Guo, Zhe Li, Ying Liu, Yongtai Zhang, Nianping Feng. Improved self-assembled micelles based on supercritical fluid technology as a novel oral delivery system for enhancing germacrone oral bioavailability. International journal of pharmaceutics. 2019 Oct; 569(?):118586. doi: 10.1016/j.ijpharm.2019.118586. [PMID: 31377407]
  • Alberto Galisteo Pretel, Helena Pérez Del Pulgar, Estela Guerrero de León, José Luis López-Pérez, A Sonia Olmeda, Azucena Gonzalez-Coloma, Alejandro F Barrero, José Francisco Quílez Del Moral. Germacrone Derivatives as new Insecticidal and Acaricidal Compounds: A Structure-Activity Relationship. Molecules (Basel, Switzerland). 2019 Aug; 24(16):. doi: 10.3390/molecules24162898. [PMID: 31404973]
  • Yixuan Huang, Changsong Xue, Wenbing He, Xingchen Zhao. Inhibition effect of Zedoary turmeric oil on Listeria monocytogenes and Staphylococcus aureus growth and exotoxin proteins production. Journal of medical microbiology. 2019 Apr; 68(4):657-666. doi: 10.1099/jmm.0.000949. [PMID: 30882292]
  • Qi Kong, Yong Ma, Jie Yu, Xiuping Chen. Predicted molecular targets and pathways for germacrone, curdione, and furanodiene in the treatment of breast cancer using a bioinformatics approach. Scientific reports. 2017 Nov; 7(1):15543. doi: 10.1038/s41598-017-15812-9. [PMID: 29138518]
  • Sudipta Jena, Asit Ray, Anwesha Banerjee, Ambika Sahoo, Noohi Nasim, Suprava Sahoo, Basudeba Kar, Jeetendranath Patnaik, Pratap Chandra Panda, Sanghamitra Nayak. Chemical composition and antioxidant activity of essential oil from leaves and rhizomes of Curcuma angustifolia Roxb. Natural product research. 2017 Sep; 31(18):2188-2191. doi: 10.1080/14786419.2017.1278600. [PMID: 28067055]
  • Chang-Xin Zhou, Li-Sha Zhang, Fei-Fei Chen, Hao-Shu Wu, Jian-Xia Mo, Li-She Gan. Terpenoids from Curcuma wenyujin increased glucose consumption on HepG2 cells. Fitoterapia. 2017 Sep; 121(?):141-145. doi: 10.1016/j.fitote.2017.06.011. [PMID: 28625730]
  • Riccardo Petrelli, Farahnaz Ranjbarian, Stefano Dall'Acqua, Fabrizio Papa, Romilde Iannarelli, Stephane L Ngahang Kamte, Sauro Vittori, Giovanni Benelli, Filippo Maggi, Anders Hofer, Loredana Cappellacci. An overlooked horticultural crop, Smyrnium olusatrum, as a potential source of compounds effective against African trypanosomiasis. Parasitology international. 2017 Apr; 66(2):146-151. doi: 10.1016/j.parint.2017.01.001. [PMID: 28087440]
  • Jie Wu, Yu Feng, Chao Han, Wu Huang, Zhibin Shen, Mengdie Yang, Weiqiang Chen, Lianbao Ye. Germacrone derivatives: synthesis, biological activity, molecular docking studies and molecular dynamics simulations. Oncotarget. 2017 Feb; 8(9):15149-15158. doi: 10.18632/oncotarget.14832. [PMID: 28148897]
  • Yuan-Ri Guo, Se-Young Choung. Germacrone inhibits adipogenesis and stimulates lipolysis via the AMP-activated protein kinase signalling pathway in 3T3-L1 preadipocytes. The Journal of pharmacy and pharmacology. 2017 Feb; 69(2):202-212. doi: 10.1111/jphp.12674. [PMID: 27917474]
  • Yuan-Ri Guo, Se-Young Choung. Germacrone Attenuates Hyperlipidemia and Improves Lipid Metabolism in High-Fat Diet-Induced Obese C57BL/6J Mice. Journal of medicinal food. 2017 Jan; 20(1):46-55. doi: 10.1089/jmf.2016.3811. [PMID: 28098516]
  • Jukkarin Srivflai, Nantaka Khorana, Neti Waranuch, Wudtichai Wisuitiprot, Nungruthai Suphrom, Apichart Suksamrarn, Kornkanok Ingkaninan. Germacrene Analogs are Anti-androgenic on Androgen-dependent Cells. Natural product communications. 2016 Sep; 11(9):1225-1228. doi: . [PMID: 30807005]
  • Hongxia Wu, Yongxiang Liu, Shaopo Zu, Xue Sun, Chunguo Liu, Dafei Liu, Xiaozhan Zhang, Jin Tian, Liandong Qu. In vitro antiviral effect of germacrone on feline calicivirus. Archives of virology. 2016 Jun; 161(6):1559-67. doi: 10.1007/s00705-016-2825-8. [PMID: 26997613]
  • Mitsuo Miyazawa, Seiji Yoshinaga, Yusei Kashima, Hiroshi Nakahashi, Nobuyuki Hara, Hiroki Nakagawa, Atsushi Usami. Chemical Composition and Characteristic Odor Compounds in Essential Oil from Alismatis Rhizoma (Tubers of Alisma orientale). Journal of oleo science. 2016; 65(1):91-7. doi: 10.5650/jos.ess15176. [PMID: 26666273]
  • Weidong Pan, Lixin Yang, Weihong Feng, Limei Lin, Chun Li, Weiwei Liu, Guofeng Gan, Junhong Fan, Jigao Zou, Zhimin Wang, Haifeng Pan. Determination of five sesquiterpenoids in Xingnaojing injection by quantitative analysis of multiple components with a single marker. Journal of separation science. 2015 Oct; 38(19):3313-23. doi: 10.1002/jssc.201500494. [PMID: 26200507]
  • Baolian Wang, Shuang Yang, Li Sheng, Yan Li. Simultaneous quantification of curdione, furanodiene and germacrone in rabbit plasma using liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2015 Sep; 29(9):1393-8. doi: 10.1002/bmc.3436. [PMID: 25678109]
  • Yan-xiong Gan, Ni-ni Luo, Yan-ping Jiang, Qiao Liu, Shu Fu, Lei Wang, Wan Liao, Chao-mei Fu. [Simultaneous determination of beta-elemene, curcumol, germacrone and neocurdione in volatile oil of Curcuma phaeocaulis and vinegar products by GC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2015 Apr; 40(7):1311-5. doi: . [PMID: 26281553]
  • J-F An, Y Sun, Q-L Zhang, F-L Zhang, J-L Zhang. The effects of germacrone on lipopolysaccharide-induced acute lung injury in neonatal rats. Cellular and molecular biology (Noisy-le-Grand, France). 2014 Nov; 60(4):8-12. doi: . [PMID: 25399081]
  • Yue-Wei An, Guang Hu, Guo-Ping Yin, Jing-Jing Zhu, Qi-Wei Zhang, Zhi-Min Wang, Juan Peng, Bin Fan. Quantitative analysis and discrimination of steamed and non-steamed rhizomes of Curcuma wenyujin by GC-MS and HPLC. Journal of chromatographic science. 2014 Oct; 52(9):961-70. doi: 10.1093/chromsci/bmt149. [PMID: 24105919]
  • Nungruthai Suphrom, Jukkarin Srivilai, Ganniga Pumthong, Nantaka Khorana, Neti Waranuch, Nanteetip Limpeanchob, Kornkanok Ingkaninan. Stability studies of antiandrogenic compounds in Curcuma aeruginosa Roxb. extract. The Journal of pharmacy and pharmacology. 2014 Sep; 66(9):1282-93. doi: 10.1111/jphp.12216. [PMID: 24905238]
  • Bo Liu, Yue-Qiu Gao, Xiao-Min Wang, Yu-Chun Wang, Li-Qi Fu. Germacrone inhibits the proliferation of glioma cells by promoting apoptosis and inducing cell cycle arrest. Molecular medicine reports. 2014 Aug; 10(2):1046-50. doi: 10.3892/mmr.2014.2290. [PMID: 24889088]
  • Niko S Radulović, Dragan Zlatković, Milan Dekić, Zorica Stojanović-Radić. Further antibacterial Geranium macrorrhizum L. metabolites and synthesis of epoxygermacrones. Chemistry & biodiversity. 2014 Apr; 11(4):542-50. doi: 10.1002/cbdv.201300295. [PMID: 24706624]
  • Sok-Lai Hong, Guan-Serm Lee, Syarifah Nur Syed Abdul Rahman, Omer Abdalla Ahmed Hamdi, Khalijah Awang, Nurfina Aznam Nugroho, Sri Nurestri Abd Malek. Essential oil content of the rhizome of Curcuma purpurascens Bl. (Temu Tis) and its antiproliferative effect on selected human carcinoma cell lines. TheScientificWorldJournal. 2014; 2014(?):397430. doi: 10.1155/2014/397430. [PMID: 25177723]
  • Qingjiao Liao, Zhengxu Qian, Rui Liu, Liwei An, Xulin Chen. Germacrone inhibits early stages of influenza virus infection. Antiviral research. 2013 Dec; 100(3):578-88. doi: 10.1016/j.antiviral.2013.09.021. [PMID: 24095670]
  • Yun-Yi Liu, Qian Zheng, Bin Fang, Wei Wang, Feng-Yun Ma, Sadia Roshan, Amal Banafa, Ming-Jie Chen, Jun-Li Chang, Xiao-Min Deng, Ke-Xiu Li, Guang-Xiao Yang, Guang-Yuan He. Germacrone induces apoptosis in human hepatoma HepG2 cells through inhibition of the JAK2/STAT3 signalling pathway. Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban. 2013 Jun; 33(3):339-345. doi: 10.1007/s11596-013-1121-z. [PMID: 23771657]
  • Yin-Yu Li, Yu Bei, Hui Zhang, Jian-An Li, Wen Zhao, Qiao-Xue Xiao, Min-Jing Zhang, Ya-Dong Huang, Qi Xiang. [Study on effect of Hypericum perforatum on pharmacokinetics of zedoary turmeric oil in compound antiviral preparation]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2013 Apr; 38(7):1083-6. doi: NULL. [PMID: 23847963]
  • Yunyi Liu, Wei Wang, Bin Fang, Fengyun Ma, Qian Zheng, Pengyi Deng, Shasha Zhao, Mingjie Chen, Guangxiao Yang, Guangyuan He. Anti-tumor effect of germacrone on human hepatoma cell lines through inducing G2/M cell cycle arrest and promoting apoptosis. European journal of pharmacology. 2013 Jan; 698(1-3):95-102. doi: 10.1016/j.ejphar.2012.10.013. [PMID: 23117090]
  • Nungruthai Suphrom, Ganniga Pumthong, Nantaka Khorana, Neti Waranuch, Nanteetip Limpeanchob, Kornkanok Ingkaninan. Anti-androgenic effect of sesquiterpenes isolated from the rhizomes of Curcuma aeruginosa Roxb. Fitoterapia. 2012 Jul; 83(5):864-71. doi: 10.1016/j.fitote.2012.03.017. [PMID: 22465508]
  • Niko S Radulović, Milan S Dekić, Zorica Z Stojanović-Radić, Suad K Zoranić. Geranium macrorrhizum L. (Geraniaceae) essential oil: a potent agent against Bacillus subtilis. Chemistry & biodiversity. 2010 Nov; 7(11):2783-800. doi: 10.1002/cbdv.201000100. [PMID: 21072778]
  • Xiao-Jing Cheng, Hua-Gang Liu, Yue-Kui Liao, Mao-Xiang Lai, Jun-Ying Liu, Zheng-Lin Lu. [Comparisons of volatile components in different parts of three species of Rhizoma Curcumae]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Oct; 32(10):1551-3. doi: ". [PMID: 20112719]
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  • Feng-qing Yang, Shao-ping Li, Ying Chen, Qian-qing Liu, Yi-tao Wang, Ting-xia Dong, Hua-qiang Zhan. [The fingerprint of Ezhu by GC-MS]. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Nov; 40(11):1013-8. doi: ". [PMID: 16499086]
  • Jian You, Fu-de Cui, Qing-po Li, Wang Yong-sheng, Xu Han, Ying-wei Yu. A HPLC method for the analysis of germacrone in rabbit plasma and its application to a pharmacokinetic study of germacrone after administration of zedoary turmeric oil. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Sep; 823(2):172-6. doi: 10.1016/j.jchromb.2005.06.032. [PMID: 16029964]
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  • Jian You, Qing-po Li, Ying-wei Yu, Fu-de Cui. [Absorption of zedoary oil in rat intestine using in situ single pass perfusion model]. Yao xue xue bao = Acta pharmaceutica Sinica. 2004 Oct; 39(10):849-53. doi: ". [PMID: 15700830]
  • A Rangelov, P Kossev, P Malakov. Experimental study of essential oils from two varieties of cultivated thyme, sesquiterpene Germacron and diterpene Sclareol for cholagogic and choleretic activity. Folia medica. 1989; 31(3):34-8. doi: . [PMID: 2490810]
  • S J Tian. [The volatile oil of zedoaria IV: TLC densitometric determination of germacrone in the essential oils from Curcuma wenyujin and C. kwangsinensis]. Zhong yao tong bao (Beijing, China : 1981). 1985 Nov; 10(11):29-31. doi: ". [PMID: 2938786]