Deoxyelephantopin (BioDeep_00000000886)

   

PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


[(3S,4R,8R,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl] 2-methylprop-2-enoate

化学式: C19H20O6 (344.126)
中文名称: 异脱氧肾上腺素, 去氧地胆草素, 异去氧苦地胆苦素, 异去氧苦地胆素
谱图信息: 最多检出来源 Escherichia coli(natural_products) 13.82%

分子结构信息

SMILES: C=C(C)C(=O)OC1CC2=CC(CC(C)=CC3OC(=O)C(=C)C31)OC2=O
InChI: InChI=1S/C19H20O6/c1-9(2)17(20)24-15-8-12-7-13(23-19(12)22)5-10(3)6-14-16(15)11(4)18(21)25-14/h6-7,13-16H,1,4-5,8H2,2-3H3

描述信息

Deoxyelephantopin is a sesquiterpenoid.
Deoxyelephantopin is a natural product found in Elephantopus scaber with data available.
Isodeoxyelephantopin is a terpene lactone.
Deoxyelephantopin, a natural bioactive sesquiterpene lactone from Elephantopus scaber, has shown promising anticancer effects against a broad spectrum of cancers. Deoxyelephantopin inhibits NF-κB, MAPK, PI3K/Akt, and β-catenin signaling[1].
Deoxyelephantopin, a natural bioactive sesquiterpene lactone from Elephantopus scaber, has shown promising anticancer effects against a broad spectrum of cancers. Deoxyelephantopin inhibits NF-κB, MAPK, PI3K/Akt, and β-catenin signaling[1].

同义名列表

5 个代谢物同义名

[(3S,4R,8R,9E,12R)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl] 2-methylprop-2-enoate; Isodeoxyelephantopin; Deoxyelephantopin; (10-Methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl) 2-methylprop-2-enoate; Deoxyelephantopin



数据库引用编号

19 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)

2 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 13 AIMP2, ANXA5, BCL2, CASP3, CCNB1, MAPK8, MTOR, PIK3CA, PPARG, PTGS2, STAT3, TXNRD1, VEGFA
Peripheral membrane protein 4 ANXA5, GORASP1, MTOR, PTGS2
Endoplasmic reticulum membrane 4 BCL2, HMOX1, MTOR, PTGS2
Nucleus 12 AIMP2, BCL2, CASP3, CCNB1, HMOX1, MAPK8, MTOR, PARP1, PPARG, STAT3, TXNRD1, VEGFA
autophagosome 1 MAP1LC3A
cytosol 14 AIMP2, ANXA5, BCL2, CASP3, CCNB1, HMOX1, MAP1LC3A, MAPK8, MTOR, PARP1, PIK3CA, PPARG, STAT3, TXNRD1
dendrite 1 MTOR
nuclear body 1 PARP1
phagocytic vesicle 1 MTOR
centrosome 1 CCNB1
nucleoplasm 9 CASP3, CCNB1, HMOX1, MAPK8, MTOR, PARP1, PPARG, STAT3, TXNRD1
RNA polymerase II transcription regulator complex 2 PPARG, STAT3
Lipid-anchor 1 MAP1LC3A
Cytoplasmic side 3 GORASP1, HMOX1, MTOR
lamellipodium 1 PIK3CA
Golgi apparatus membrane 2 GORASP1, MTOR
Synapse 1 MAPK8
cell surface 1 VEGFA
glutamatergic synapse 2 CASP3, MAP1LC3A
Golgi apparatus 2 GORASP1, VEGFA
Golgi membrane 2 GORASP1, MTOR
lysosomal membrane 1 MTOR
neuronal cell body 1 CASP3
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AIMP2, PARP1
Lysosome 1 MTOR
plasma membrane 2 PIK3CA, STAT3
Membrane 8 AIMP2, ANXA5, BCL2, CCNB1, HMOX1, MTOR, PARP1, VEGFA
axon 2 CCK, MAPK8
caveola 1 PTGS2
extracellular exosome 2 ANXA5, TXNRD1
Lysosome membrane 1 MTOR
endoplasmic reticulum 4 BCL2, HMOX1, PTGS2, VEGFA
extracellular space 4 CCK, HMOX1, IL6, VEGFA
perinuclear region of cytoplasm 3 HMOX1, PIK3CA, PPARG
adherens junction 1 VEGFA
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, PARP1, TXNRD1
protein-containing complex 3 BCL2, PARP1, PTGS2
intracellular membrane-bounded organelle 2 MAP1LC3A, PPARG
Microsome membrane 2 MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 3 CCK, IL6, VEGFA
extracellular region 4 ANXA5, CCK, IL6, VEGFA
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 3 BCL2, HMOX1, MTOR
mitochondrial matrix 1 CCNB1
transcription regulator complex 2 PARP1, STAT3
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 ANXA5
Secreted, extracellular space, extracellular matrix 1 VEGFA
nucleolus 1 PARP1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 MAP1LC3A
focal adhesion 1 ANXA5
microtubule 1 MAP1LC3A
cis-Golgi network 1 GORASP1
extracellular matrix 1 VEGFA
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 ANXA5
secretory granule 1 VEGFA
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAP1LC3A
receptor complex 1 PPARG
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 3 PARP1, PPARG, STAT3
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
Chromosome 1 PARP1
[Isoform 5]: Cytoplasm 1 TXNRD1
Nucleus, nucleolus 1 PARP1
spindle pole 1 CCNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
organelle membrane 1 MAP1LC3A
site of double-strand break 1 PARP1
fibrillar center 1 TXNRD1
nuclear envelope 2 MTOR, PARP1
Endomembrane system 2 MAP1LC3A, MTOR
myelin sheath 1 BCL2
[Isoform 1]: Cytoplasm 1 TXNRD1
[Isoform 4]: Cytoplasm 1 TXNRD1
endoplasmic reticulum lumen 2 IL6, PTGS2
platelet alpha granule lumen 1 VEGFA
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
outer kinetochore 1 CCNB1
vesicle membrane 1 ANXA5
protein-DNA complex 1 PARP1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Cytoplasmic vesicle, phagosome 1 MTOR
site of DNA damage 1 PARP1
Autolysosome 1 MAP1LC3A
interleukin-6 receptor complex 1 IL6
cyclin B1-CDK1 complex 1 CCNB1
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

  • Can-Chao Jia, Ling-Jie Li, Zhi-Hao Zeng, Rui-Yin Tang, De-Zheng Jia, Min-Juan Yang, Jin-Yan Qiu, Dong-Mei Li, Can-Hui Xie, Guang-Ying Wu, Yang-Xue Li, Jie-Yi Jiang, Hong Huang, Guan-Lin Xiao, Da-Ke Cai, Xiao-Li Bi. [Prediction and analysis of Q-markers of Elephantopus scaber based on its UPLC fingerprint, content determination of components, and in vitro a nti-tumor activity]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Aug; 48(16):4421-4428. doi: 10.19540/j.cnki.cjcmm.20230526.201. [PMID: 37802868]
  • Haoyan Ji, Kui Zhang, Guangzhao Pan, Changhong Li, Chongyang Li, Xin Hu, Liqun Yang, Hongjuan Cui. Deoxyelephantopin Induces Apoptosis and Enhances Chemosensitivity of Colon Cancer via miR-205/Bcl2 Axis. International journal of molecular sciences. 2022 May; 23(9):. doi: 10.3390/ijms23095051. [PMID: 35563442]
  • Biljana Cvetanova, Meng-Yi Li, Chung-Chih Yang, Pei-Wen Hsiao, Yu-Chih Yang, Jia-Hua Feng, Ya-Ching Shen, Kyoko Nakagawa-Goto, Kuo-Hsiung Lee, Lie-Fen Shyur. Sesquiterpene Lactone Deoxyelephantopin Isolated from Elephantopus scaber and Its Derivative DETD-35 Suppress BRAFV600E Mutant Melanoma Lung Metastasis in Mice. International journal of molecular sciences. 2021 Mar; 22(6):. doi: 10.3390/ijms22063226. [PMID: 33810045]
  • Yixin Han, Ximeng Li, Xiaoyu Zhang, Yuan Gao, Ruijuan Qi, Runlan Cai, Yun Qi. Isodeoxyelephantopin, a sesquiterpene lactone from Elephantopus scaber Linn., inhibits pro-inflammatory mediators' production through both NF-κB and AP-1 pathways in LPS-activated macrophages. International immunopharmacology. 2020 Jul; 84(?):106528. doi: 10.1016/j.intimp.2020.106528. [PMID: 32335480]
  • Wei Gao, Jing Sun, Feng Wang, Yuxian Lu, Chun Wen, Qingya Bian, Hongyan Wu. Deoxyelephantopin suppresses hepatic stellate cells activation associated with inhibition of aerobic glycolysis via hedgehog pathway. Biochemical and biophysical research communications. 2019 09; 516(4):1222-1228. doi: 10.1016/j.bbrc.2019.07.015. [PMID: 31296386]
  • Yi Fan Teah, Muhammad Asyraf Abduraman, Azimah Amanah, Mohd Ilham Adenan, Shaida Fariza Sulaiman, Mei Lan Tan. The effects of deoxyelephantopin on the cardiac delayed rectifier potassium channel current (IKr) and human ether-a-go-go-related gene (hERG) expression. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Sep; 107(Pt A):293-301. doi: 10.1016/j.fct.2017.07.011. [PMID: 28689918]
  • Tahir Mehmood, Amara Maryam, Hamed A Ghramh, Muhammad Khan, Tonghui Ma. Deoxyelephantopin and Isodeoxyelephantopin as Potential Anticancer Agents with Effects on Multiple Signaling Pathways. Molecules (Basel, Switzerland). 2017 Jun; 22(6):. doi: 10.3390/molecules22061013. [PMID: 28635648]
  • Jia-Hua Feng, Kyoko Nakagawa-Goto, Kuo-Hsiung Lee, Lie-Fen Shyur. A Novel Plant Sesquiterpene Lactone Derivative, DETD-35, Suppresses BRAFV600E Mutant Melanoma Growth and Overcomes Acquired Vemurafenib Resistance in Mice. Molecular cancer therapeutics. 2016 06; 15(6):1163-76. doi: 10.1158/1535-7163.mct-15-0973. [PMID: 27048951]
  • G Sánchez-Toranzo, J Zapata-Martínez, C Catalán, M I Bühler. Effect of different types of sesquiterpene lactones on the maturation of Rhinella arenarum oocytes. Zygote (Cambridge, England). 2015 Jun; 23(3):406-11. doi: 10.1017/s0967199413000695. [PMID: 24522008]
  • Zuriati Zahari, Nor Akmalazura Jani, Azimah Amanah, Mohd Naffidi Abdul Latif, Mohamed Isa Abdul Majid, Mohd Ilham Adenan. Bioassay-guided isolation of a sesquiterpene lactone of deoxyelephantopin from Elephantopus scaber Linn. active on Trypanosome brucei rhodesience. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Feb; 21(3):282-5. doi: 10.1016/j.phymed.2013.09.011. [PMID: 24269185]
  • Chi-Chang Huang, Kun-Ju Lin, Ya-Wen Cheng, Chih-An Hsu, Sien-Sing Yang, Lie-Fen Shyur. Hepatoprotective effect and mechanistic insights of deoxyelephantopin, a phyto-sesquiterpene lactone, against fulminant hepatitis. The Journal of nutritional biochemistry. 2013 Mar; 24(3):516-30. doi: 10.1016/j.jnutbio.2012.01.013. [PMID: 22748804]
  • Wai-Leng Lee, Lie-Fen Shyur. Deoxyelephantopin impedes mammary adenocarcinoma cell motility by inhibiting calpain-mediated adhesion dynamics and inducing reactive oxygen species and aggresome formation. Free radical biology & medicine. 2012 Apr; 52(8):1423-36. doi: 10.1016/j.freeradbiomed.2012.01.020. [PMID: 22342517]
  • B S Geetha, Mangalam S Nair, P G Latha, P Remani. Sesquiterpene lactones isolated from Elephantopus scaber L. inhibits human lymphocyte proliferation and the growth of tumour cell lines and induces apoptosis in vitro. Journal of biomedicine & biotechnology. 2012; 2012(?):721285. doi: 10.1155/2012/721285. [PMID: 22500104]
  • Qiao-Li Liang, Zhi-Da Min, Yu-Ping Tang. A new elemanolide sesquiterpene lactone from Elephantopus scaber. Journal of Asian natural products research. 2008 May; 10(5-6):403-7. doi: 10.1080/10286020801966526. [PMID: 18464077]
  • Qiao-li Liang, Zhi-da Min. [Structure modification on sesquiterpene lactones from Elephantopus scaber]. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 Nov; 42(11):1159-61. doi: . [PMID: 18300472]