Curdione (BioDeep_00000000331)

 

Secondary id: BioDeep_00000229823

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


6-Cyclodecene-1,4-dione, 6,10-dimethyl-3-(1-methylethyl)-, (3S-(3R*,6E,10R*))-

化学式: C15H24O2 (236.1776)
中文名称: 莪术二酮, 姜黄二酮, 莪二酮
谱图信息: 最多检出来源 Macaca mulatta(otcml) 76.37%

分子结构信息

SMILES: C/C1=C/CC[C@H](C)C(=O)C[C@@H](C(C)C)C(=O)C1
InChI: InChI=1S/C15H24O2/c1-10(2)13-9-14(16)12(4)7-5-6-11(3)8-15(13)17/h6,10,12-13H,5,7-9H2,1-4H3/b11-6-

描述信息

Curdione is a germacrane sesquiterpenoid.
Germacr-1(10)-ene-5,8-dione is a natural product found in Curcuma aromatica, Curcuma wenyujin, and other organisms with data available.
Curdione is found in turmeric. Curdione is a constituent of Curcuma zedoaria (zedoary)
Constituent of Curcuma zedoaria (zedoary). Curdione is found in turmeric.
Curdione, one of the major sesquiterpene compounds from Curcuma zedoaria, has been shown to exhibit multiple bioactive properties. IC50 value: 60–80 μM Target: In vitro: The study of the influence of curdione on the hemorheological changes in blood stasis model rats and thrombolysis in vitro showed that curdione only possessed thrombolytic effect in dose of 0.235 g·L-1 and 2.35 g·L-1, but has not the notable activity of thrombolysis [1]. The effects of curdione on human platelet aggregation induced by thrombin (0.3 U/ml) were tested in vitro. Curdione preferentially inhibited PAF- and thrombin- induced platelet aggregation in a concentration-dependent manner (IC50: 60–80 μM), whereas much higher concentrations of curdione were required to inhibit platelet aggregation induced by ADP and AA. Curdione also inhibited P-selectin expression in PAF-activated platelets. Moreover, curdione caused an increase in cAMP levels and attenuated intracellular Ca2+ mobilization in PAF-activated platelets. In vivo: Curdione showed significant antithrombotic activity [2].
Curdione, one of the major sesquiterpene compounds from Curcuma zedoaria, has been shown to exhibit multiple bioactive properties. IC50 value: 60–80 μM Target: In vitro: The study of the influence of curdione on the hemorheological changes in blood stasis model rats and thrombolysis in vitro showed that curdione only possessed thrombolytic effect in dose of 0.235 g·L-1 and 2.35 g·L-1, but has not the notable activity of thrombolysis [1]. The effects of curdione on human platelet aggregation induced by thrombin (0.3 U/ml) were tested in vitro. Curdione preferentially inhibited PAF- and thrombin- induced platelet aggregation in a concentration-dependent manner (IC50: 60–80 μM), whereas much higher concentrations of curdione were required to inhibit platelet aggregation induced by ADP and AA. Curdione also inhibited P-selectin expression in PAF-activated platelets. Moreover, curdione caused an increase in cAMP levels and attenuated intracellular Ca2+ mobilization in PAF-activated platelets. In vivo: Curdione showed significant antithrombotic activity [2].

同义名列表

13 个代谢物同义名

6-Cyclodecene-1,4-dione, 6,10-dimethyl-3-(1-methylethyl)-, (3S-(3R*,6E,10R*))-; Cyclodecene-1,4-dione, 6,10-dimethyl-3-(1-methylethyl)-, (3S-(3R*,6E,10R*))-; (3S,6E,10S)-6,10-dimethyl-3-(propan-2-yl)cyclodec-6-ene-1,4-dione; (3S,6E,10S)-6,10-dimethyl-3-propan-2-ylcyclodec-6-ene-1,4-dione; (3S,10S,E)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione; (6Z)-6,10-dimethyl-3-(propan-2-yl)cyclodec-6-ene-1,4-dione; (6Z)-3-isopropyl-6,10-dimethylcyclodec-6-ene-1,4-dione; (+)-Germacr-1(10)-ene-5,8-dione; Germacr-1(10)-ene-5,8-dione; (+)-Curdione; Curdione; Curdione; Neocurdione



数据库引用编号

25 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)

49 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 AKT1, BCL2, CA2, CASP3, CASP9, CYP3A4, KEAP1, PIK3CA, PTGS2, VCL, YTHDF2
Peripheral membrane protein 2 PTGS2, VCL
Endoplasmic reticulum membrane 5 BCL2, CYP3A4, HMOX1, PTGS2, SLC7A11
Nucleus 11 AKT1, BCL2, CASP3, CASP9, GABPA, GPX4, HMOX1, HOXA13, KEAP1, METTL14, YTHDF2
cytosol 11 AKT1, BCL2, CA2, CASP3, CASP9, GPX4, HMOX1, KEAP1, PIK3CA, VCL, YTHDF2
nucleoplasm 8 AKT1, CASP3, GABPA, HMOX1, HOXA13, KEAP1, METTL14, SLC3A2
Cell membrane 6 AKT1, CA2, ITGAM, SLC3A2, SLC7A11, VCL
Cytoplasmic side 2 HMOX1, VCL
lamellipodium 2 AKT1, PIK3CA
Multi-pass membrane protein 1 SLC7A11
Synapse 1 SLC3A2
cell cortex 1 AKT1
cell junction 1 SLC3A2
cell surface 3 ITGAM, SLC3A2, SLC7A11
glutamatergic synapse 2 AKT1, CASP3
lysosomal membrane 1 SLC3A2
neuronal cell body 1 CASP3
postsynapse 1 AKT1
sarcolemma 1 VCL
Cytoplasm, cytosol 1 YTHDF2
plasma membrane 8 AKT1, CA2, F2, ITGAM, PIK3CA, SLC3A2, SLC7A11, VCL
Membrane 7 AKT1, BCL2, CYP3A4, HMOX1, ITGAM, SLC3A2, SLC7A11
apical plasma membrane 1 SLC3A2
basolateral plasma membrane 2 SLC3A2, SLC7A11
brush border 1 VCL
caveola 1 PTGS2
extracellular exosome 6 CA2, F2, GPX4, ITGAM, SLC3A2, VCL
Lysosome membrane 1 SLC3A2
endoplasmic reticulum 4 BCL2, HMOX1, KEAP1, PTGS2
extracellular space 3 F2, HMOX1, ITGAM
perinuclear region of cytoplasm 2 HMOX1, PIK3CA
adherens junction 1 VCL
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, CASP9, GPX4
protein-containing complex 6 AKT1, BCL2, CASP9, GPX4, PTGS2, VCL
intracellular membrane-bounded organelle 1 CYP3A4
Microsome membrane 2 CYP3A4, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 ITGAM, SLC7A11
Secreted 1 F2
extracellular region 2 F2, VCL
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, HMOX1
anchoring junction 1 SLC3A2
centriolar satellite 2 KEAP1, YTHDF2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 ITGAM
Extracellular vesicle 1 VCL
microtubule cytoskeleton 1 AKT1
midbody 1 KEAP1
Cytoplasm, P-body 1 YTHDF2
P-body 1 YTHDF2
apical part of cell 2 CA2, SLC7A11
cell-cell junction 2 AKT1, VCL
Single-pass type II membrane protein 1 SLC3A2
vesicle 1 AKT1
Apical cell membrane 1 SLC3A2
Cell membrane, sarcolemma 1 VCL
Membrane raft 2 ITGAM, VCL
pore complex 1 BCL2
Cell junction, focal adhesion 1 VCL
Cytoplasm, cytoskeleton 1 VCL
focal adhesion 1 VCL
spindle 1 AKT1
Cell junction, adherens junction 1 VCL
zonula adherens 1 VCL
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 F2
fascia adherens 1 VCL
lateral plasma membrane 1 SLC7A11
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 2 GABPA, HOXA13
cell projection 1 VCL
Chromosome 1 HOXA13
cytoskeleton 1 VCL
Cell projection, podosome 1 VCL
podosome 1 VCL
cytoplasmic ribonucleoprotein granule 1 YTHDF2
brush border membrane 1 SLC7A11
actin filament 1 KEAP1
blood microparticle 1 F2
Basolateral cell membrane 2 SLC3A2, SLC7A11
Cell projection, microvillus membrane 1 SLC7A11
microvillus membrane 1 SLC7A11
Cul3-RING ubiquitin ligase complex 1 KEAP1
nuclear envelope 1 GPX4
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
Melanosome 1 SLC3A2
Cytoplasm, Stress granule 1 YTHDF2
cytoplasmic stress granule 1 YTHDF2
myelin sheath 2 BCL2, CA2
intermediate filament cytoskeleton 1 HOXA13
basal plasma membrane 1 SLC3A2
plasma membrane raft 1 ITGAM
ficolin-1-rich granule lumen 1 VCL
secretory granule lumen 1 VCL
Golgi lumen 1 F2
endoplasmic reticulum lumen 2 F2, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 VCL
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
costamere 1 VCL
death-inducing signaling complex 1 CASP3
cell-substrate junction 1 VCL
terminal web 1 VCL
integrin complex 1 ITGAM
cell-cell contact zone 1 VCL
astrocyte projection 1 SLC7A11
inclusion body 1 KEAP1
integrin alphaM-beta2 complex 1 ITGAM
[Isoform Mitochondrial]: Mitochondrion 1 GPX4
amino acid transport complex 1 SLC3A2
apical pole of neuron 1 SLC3A2
BAD-BCL-2 complex 1 BCL2
inner dense plaque of desmosome 1 VCL
outer dense plaque of desmosome 1 VCL
podosome ring 1 VCL
[Isoform Cytoplasmic]: Cytoplasm 1 GPX4
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
caspase complex 1 CASP9
RNA N6-methyladenosine methyltransferase complex 1 METTL14


文献列表

  • Huihui Wang, Baoping Xie, Shuotao Shi, Rong Zhang, Qi Liang, Zhongqiu Liu, Yuanyuan Cheng. Curdione inhibits ferroptosis in isoprenaline-induced myocardial infarction via regulating Keap1/Trx1/GPX4 signaling pathway. Phytotherapy research : PTR. 2023 Jul; ?(?):. doi: 10.1002/ptr.7964. [PMID: 37500597]
  • Kai Yang, Bin Wu, Wu Wei, Cuiyu Li, Lu Li, Zhukai Cong, Qian Xiang. Curdione ameliorates sepsis-induced lung injury by inhibiting platelet-mediated neutrophil extracellular trap formation. International immunopharmacology. 2023 Mar; 118(?):110082. doi: 10.1016/j.intimp.2023.110082. [PMID: 36989889]
  • 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]
  • Bi Wang, Fei Liu, Qi Li, Shu Xu, Xingzeng Zhao, Peilin Xue, Xu Feng. Antifungal activity of zedoary turmeric oil against Phytophthora capsici through damaging cell membrane. Pesticide biochemistry and physiology. 2019 Sep; 159(?):59-67. doi: 10.1016/j.pestbp.2019.05.014. [PMID: 31400785]
  • Zimei Wu, Wenjing Zai, Wei Chen, Yuxuan Han, Xin Jin, Hongrui Liu. Curdione Ameliorated Doxorubicin-Induced Cardiotoxicity Through Suppressing Oxidative Stress and Activating Nrf2/HO-1 Pathway. Journal of cardiovascular pharmacology. 2019 08; 74(2):118-127. doi: 10.1097/fjc.0000000000000692. [PMID: 31356549]
  • Hui Fang, Beibei Gao, Yingli Zhao, Xing Fang, Maohong Bian, Quan Xia. Curdione inhibits thrombin-induced platelet aggregation via regulating the AMP-activated protein kinase-vinculin/talin-integrin αIIbβ3 sign pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Aug; 61(?):152859. doi: 10.1016/j.phymed.2019.152859. [PMID: 31039534]
  • 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]
  • 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]
  • 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]
  • Xiang Meng, Ting Zhang, Ying Li, Qi Pan, Juan Jiang, Yongwei Luo, Liming Chong, Yang Yang, Sichong Xu, Li Zhou, Zuyue Sun. Development and application of an analytical method for curdione quantification in pregnant Sprague-Dawley rats by LC-MS/MS. Biomedical chromatography : BMC. 2015 Oct; 29(10):1499-505. doi: 10.1002/bmc.3449. [PMID: 25736727]
  • 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]
  • Xiang Meng, Ting Zhang, Ying Li, Qi Pan, Juan Jiang, Yongwei Luo, Liming Chong, Yang Yang, Sichong Xu, Li Zhou, Zuyue Sun. The toxicokinetic profile of curdione in pregnant SD rats and its transference in a placental barrier system detected by LC-MS/MS. Regulatory toxicology and pharmacology : RTP. 2015 Mar; 71(2):158-63. doi: 10.1016/j.yrtph.2014.12.005. [PMID: 25527910]
  • Ying Peng, Mei Zhang, Weiwei Li, Bingjie Liu, Haiqing Wu, Fai Jiang, Lulu Zhao, Huafeng Zhu. A validated LC-MS/MS assay for the quantitative determination of curdione in rabbit plasma and its application to a pharmacokinetic study after administration of zedoary turmeric oil and bioavailability of the oil. Biomedical chromatography : BMC. 2014 Oct; 28(10):1360-5. doi: 10.1002/bmc.3175. [PMID: 24782363]
  • Diya Lv, Yan Cao, Xin Dong, Xiaofei Chen, Ziyang Lou, Yifeng Chai. Analysis and pharmacokinetic study of curdione in Rhizoma Curcumae by UPLC/QTOF/MS. Biomedical chromatography : BMC. 2014 Jun; 28(6):782-7. doi: 10.1002/bmc.3118. [PMID: 24861744]
  • Jie Feng, Ming-ming Xu, Xiu-lan Huang, Hua-gang Liu, Mao-xiang Lai, Meng-han Wei. [GC-MS analysis of essential oil from Curcuma aromatica rhizome of different growth periods]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Dec; 36(12):1926-9. doi: ". [PMID: 25090672]
  • Jing-Jing Zhu, Yue-Wei An, Guang Hu, Guo-Ping Yin, Qi-Wei Zhang, Zhi-Min Wang. Simultaneous determination of multiple sesquiterpenes in Curcuma wenyujin herbal medicines and related products with one single reference standard. Molecules (Basel, Switzerland). 2013 Feb; 18(2):2110-21. doi: 10.3390/molecules18022110. [PMID: 23389255]
  • Quan Xia, Xiu Wang, Du-Juan Xu, Xiao-Huan Chen, Fei-Hu Chen. Inhibition of platelet aggregation by curdione from Curcuma wenyujin essential Oil. Thrombosis research. 2012 Sep; 130(3):409-14. doi: 10.1016/j.thromres.2012.04.005. [PMID: 22560337]
  • Jianshe Ma, Jianyong Dong, Guanyang Lin, Lei Yue, Zheng Xiang, Renai Xu, Lufeng Hu, Xianqin Wang. Determination of curdione in rabbit plasma by liquid chromatography mass spectrometry. Biomedical chromatography : BMC. 2012 May; 26(5):655-9. doi: 10.1002/bmc.1711. [PMID: 21932392]
  • 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]
  • Yang Qu, Fengming Xu, Seikou Nakamura, Hisashi Matsuda, Yutana Pongpiriyadacha, Lijun Wu, Masayuki Yoshikawa. Sesquiterpenes from Curcuma comosa. Journal of natural medicines. 2009 Jan; 63(1):102-4. doi: 10.1007/s11418-008-0282-8. [PMID: 18663560]
  • J S Zhang, J Guan, F Q Yang, H G Liu, X J Cheng, S P Li. Qualitative and quantitative analysis of four species of Curcuma rhizomes using twice development thin layer chromatography. Journal of pharmaceutical and biomedical analysis. 2008 Nov; 48(3):1024-8. doi: 10.1016/j.jpba.2008.07.006. [PMID: 18722068]
  • O-Jin Oh, Hye-Young Min, Sang Kook Lee. Inhibition of inducible prostaglandin E2 production and cyclooxygenase-2 expression by curdione from Curcuma zedoaria. Archives of pharmacal research. 2007 Oct; 30(10):1236-9. doi: 10.1007/bf02980264. [PMID: 18038902]
  • Xiao-chi Ma, Jian Zheng, Li-jun Wu, De-an Guo. Structural determination of three new germacrane-type sesquiterpene alcohols from curdione by microbial transformation. Magnetic resonance in chemistry : MRC. 2007 Jan; 45(1):90-2. doi: 10.1002/mrc.1922. [PMID: 17103486]
  • Chunhui Deng, Jie Ji, Ning Li, Yingjia Yu, Gengli Duan, Xiangmin Zhang. Fast determination of curcumol, curdione and germacrone in three species of Curcuma rhizomes by microwave-assisted extraction followed by headspace solid-phase microextraction and gas chromatography-mass spectrometry. Journal of chromatography. A. 2006 Jun; 1117(2):115-20. doi: 10.1016/j.chroma.2006.03.066. [PMID: 16678191]
  • 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]