Euphol (BioDeep_00000000541)

 

Secondary id: BioDeep_00000416115

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(3S,5R,10S,13S,14S)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

化学式: C30H50O (426.3861)
中文名称: 大戟二烯醇, 乙草胺醇
谱图信息: 最多检出来源 Viridiplantae(plant) 24.44%

分子结构信息

SMILES: C1C[C@]2(C)C3CC[C@@]4(C)[C@H]([C@]([H])(C)CC/C=C(\C)/C)CC[C@]4(C)C=3CC[C@@]2([H])C(C)(C)[C@H]1O
InChI: InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/s1

描述信息

Euphol is a triterpenoid.
Euphol is a natural product found in Euphorbia nicaeensis, Euphorbia boetica, and other organisms with data available.
Constituent of Euphorbia subspecies (CCD). Euphol is found in many foods, some of which are cucumber, soy bean, shea tree, and tea.
Euphol is found in cucumber. Euphol is a constituent of Euphorbia species (CCD)
Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain[1].
Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain[1].
Euphol is a tetracyclic triterpene alcohol isolated from the sap of Euphorbia tirucalli with anti-mutagenic, anti-inflammatory and immunomodulatory effects, orally active. Euphol inhibits the monoacylglycerol lipase (MGL) activity via a reversible mechanism (IC50=315 nM). MGL inhibition in the periphery modulates the endocannabinoid system to block the development of inflammatory pain[1].

同义名列表

18 个代谢物同义名

(3S,5R,10S,13S,14S)-17-((R)-1,5-Dimethyl-hex-4-enyl)-4,4,10,13,14-pentamethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,5R,10S,13S,14S,17S)-17-[(1R)-1,5-dimethylhex-4-enyl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol; Lanosta-8,24-dien-3-ol, (3.beta.,13.alpha.,14.beta.,17.alpha.)-; 13alpha,14beta,17betaH-Lanosta-8,24-dien-3beta-ol (8CI); (3beta,13alpha,14beta,17alpha)-Lanosta-8,24-dien-3-ol; Lanosta-8,24-dien-3-ol,(3b,13a,14b,17a)-; (20R)-(+)-triucalla-8,24-diene-3beta-ol; 5alpha-Eupha-8,24-dien-3beta-ol; 8,24-euphadien-3 beta-ol; Eupha-8,24-dienol; (+)-alpha-Euphol; Euphol (6CI); alpha-Euphol; Euphadienol; (+)-Euphol; (s)-euphol; euphol; Euphol



数据库引用编号

18 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)

140 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, BCL2, CASP3, CAT, CCNB1, CD209, FOXO1, IRAK2, PDK1, PIK3CA, PTGS2, TBX20, TRAF6
Peripheral membrane protein 1 PTGS2
Endosome membrane 2 IRAK2, TRAF6
Endoplasmic reticulum membrane 2 BCL2, PTGS2
Nucleus 10 AIMP2, BCL2, CASP3, CCNB1, FOXO1, IRAK2, MPO, PDK1, TBX20, TRAF6
cytosol 10 AIMP2, BCL2, CASP3, CAT, CCNB1, FOXO1, IRAK2, PDK1, PIK3CA, TRAF6
centrosome 1 CCNB1
nucleoplasm 4 CASP3, CCNB1, FOXO1, MPO
Cell membrane 2 ITGB2, TNF
lamellipodium 1 PIK3CA
cell cortex 1 TRAF6
cell surface 3 CD209, ITGB2, TNF
glutamatergic synapse 2 CASP3, TRAF6
neuronal cell body 2 CASP3, TNF
Cytoplasm, cytosol 1 AIMP2
Lysosome 1 MPO
plasma membrane 7 CD209, IRAK2, ITGB2, PDK1, PIK3CA, TNF, TRAF6
Membrane 6 AIMP2, BCL2, CAT, CCNB1, CD209, ITGB2
caveola 1 PTGS2
extracellular exosome 3 CAT, ITGB2, MPO
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 5 CXCL1, IL10, IL6, MPO, TNF
perinuclear region of cytoplasm 2 PIK3CA, TRAF6
intercalated disc 1 PIK3CA
mitochondrion 4 BCL2, CAT, FOXO1, PDK1
protein-containing complex 4 BCL2, CAT, PTGS2, TRAF6
intracellular membrane-bounded organelle 2 CAT, MPO
Microsome membrane 1 PTGS2
postsynaptic density 2 CASP3, PDK1
Single-pass type I membrane protein 1 ITGB2
Secreted 2 IL10, IL6
extracellular region 7 CAT, CD209, CXCL1, IL10, IL6, MPO, TNF
cytoplasmic side of plasma membrane 1 TRAF6
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 PDK1
mitochondrial matrix 3 CAT, CCNB1, PDK1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
CD40 receptor complex 1 TRAF6
external side of plasma membrane 3 CD209, ITGB2, TNF
Extracellular vesicle 1 ITGB2
cytoplasmic vesicle 1 PDK1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 CD209, TNF
Membrane raft 2 ITGB2, TNF
pore complex 1 BCL2
focal adhesion 3 CAT, ITGB2, PDK1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 MPO
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 ITGB2
neuron projection 1 PTGS2
chromatin 2 FOXO1, TBX20
cell projection 1 PDK1
phagocytic cup 1 TNF
spindle pole 1 CCNB1
Cytoplasm, cell cortex 1 TRAF6
[Isoform 2]: Cell membrane 1 CD209
Lipid droplet 1 TRAF6
specific granule membrane 1 ITGB2
tertiary granule membrane 1 ITGB2
myelin sheath 1 BCL2
azurophil granule 1 MPO
plasma membrane raft 1 ITGB2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 2 IL6, PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
pyruvate dehydrogenase complex 1 PDK1
specific granule lumen 1 CXCL1
tertiary granule lumen 1 CXCL1
host cell 1 CD209
azurophil granule lumen 1 MPO
outer kinetochore 1 CCNB1
phagocytic vesicle lumen 1 MPO
extrinsic component of cytoplasmic side of plasma membrane 1 TRAF6
ficolin-1-rich granule membrane 1 ITGB2
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 CD209
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
integrin complex 1 ITGB2
[Isoform 3]: Cell membrane 1 CD209
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
integrin alphaL-beta2 complex 1 ITGB2
integrin alphaM-beta2 complex 1 ITGB2
integrin alphaX-beta2 complex 1 ITGB2
interleukin-6 receptor complex 1 IL6
cyclin B1-CDK1 complex 1 CCNB1
BAD-BCL-2 complex 1 BCL2
[Isoform 4]: Cell membrane 1 CD209
[Isoform 5]: Cell membrane 1 CD209
[Isoform 6]: Secreted 1 CD209
[Isoform 7]: Secreted 1 CD209
[Isoform 8]: Secreted 1 CD209
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Isoform 11]: Secreted 1 CD209
[Isoform 10]: Secreted 1 CD209
[Isoform 9]: Secreted 1 CD209
[Isoform 12]: Secreted 1 CD209


文献列表

  • Hanen Enneb, Khaled Athmouni, Rahma Thabet, Habib Ayadi. Phytochemical Compounds of Euphorbia bivonae Extract and Their Cytotoxicity Effects on the Lethality of Brine Shrimp Artemia salina and Embryonic Kidney (HEK293) Cells. Chemistry & biodiversity. 2023 Apr; ?(?):e202201135. doi: 10.1002/cbdv.202201135. [PMID: 37026603]
  • Isaac Silvère Gade, Corinne Chadéneau, Richard Tagne Simo, Emmanuel Talla, Alex De Theodore Atchade, Paule Seité, Brigitte Vannier, Sophie Laurent, Céline Henoumont, Armel H Nwabo Kamdje, Jean-Marc Muller. Euphol from Tapinanthus sp. Induces Apoptosis and Affects Signaling Proteins in Glioblastoma and Prostate Cancer Cells. Asian Pacific journal of cancer prevention : APJCP. 2022 12; 23(12):4205-4212. doi: 10.31557/apjcp.2022.23.12.4205. [PMID: 36580003]
  • Thais Latansio de Oliveira, Ariádine Reder Custodio de Souza, Pâmela Dias Fontana, Milena Carvalho Carneiro, Flávio Luís Beltrame, Iara Jose de Messias Reason, Lorena Bavia. Bioactive Secondary Plant Metabolites from Euphorbia umbellata (PAX) BRUYNS (Euphorbiaceae). Chemistry & biodiversity. 2022 Dec; 19(12):e202200568. doi: 10.1002/cbdv.202200568. [PMID: 36259393]
  • Weibo Qiao, Wei Feng, Lu Yang, Changfu Li, Xudong Qu, Yansheng Zhang. De Novo Biosynthesis of the Anticancer Compound Euphol in Saccharomyces cerevisiae. ACS synthetic biology. 2021 09; 10(9):2351-2358. doi: 10.1021/acssynbio.1c00257. [PMID: 34445867]
  • Viviane A O Silva, Marcela N Rosa, Vera Miranda-Gonçalves, Angela M Costa, Aline Tansini, Adriane F Evangelista, Olga Martinho, Adriana C Carloni, Chris Jones, João Paulo Lima, Luiz F Pianowski, Rui Manuel Reis. Euphol, a tetracyclic triterpene, from Euphorbia tirucalli induces autophagy and sensitizes temozolomide cytotoxicity on glioblastoma cells. Investigational new drugs. 2019 04; 37(2):223-237. doi: 10.1007/s10637-018-0620-y. [PMID: 29931585]
  • Luiza S Cruz, Thais L de Oliveira, Carla C Kanunfre, Katia S Paludo, Bruno R Minozzo, Ana P Prestes, Mei Wang, Daniel Fernandes, Fábio A Dos Santos, Vamshi K Manda, Shabana I Khan, Zulfiqar Ali, Iara J de Messias-Reason, Bharathi Avula, Ikhlas A Khan, Flávio L Beltrame. Pharmacokinetics and cytotoxic study of euphol from Euphorbia umbellata (Bruyns) Pax latex. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Aug; 47(?):105-112. doi: 10.1016/j.phymed.2018.04.055. [PMID: 30166094]
  • Chun-Lin Chen, Ying-Pin Chen, Ming-Wei Lin, Yaw-Bin Huang, Fang-Rong Chang, Tsai-Hui Duh, Deng-Chyang Wu, Wei-Chiang Wu, Yu-Chen Kao, Pei-Hua Yang. Euphol from Euphorbia tirucalli Negatively Modulates TGF-β Responsiveness via TGF-β Receptor Segregation inside Membrane Rafts. PloS one. 2015; 10(10):e0140249. doi: 10.1371/journal.pone.0140249. [PMID: 26448474]
  • Xu Xie, Yongning Li, Dongna Gao, Yu Zhang, Yanbo Ren. Quantitative determination of euphol in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2014 Sep; 28(9):1229-34. doi: 10.1002/bmc.3151. [PMID: 25237707]
  • Antonio C M Munhoz, Bruno R Minozzo, Luiza S Cruz, Thaís L Oliveira, Willian M Machado, Airton V Pereira, Daniel Fernandes, Francine A Manente, José C R Vellosa, Angelita Nepel, Andersson Barison, Flávio L Beltrame. Chemical and pharmacological investigation of the stem bark of Synadenium grantii. Planta medica. 2014 Apr; 80(6):458-64. doi: 10.1055/s-0034-1368300. [PMID: 24687740]
  • Rafael C Dutra, Rafaela F Claudino, Allisson F Bento, Rodrigo Marcon, Eder C Schmidt, Zenilda L Bouzon, Luiz F Pianowski, João B Calixto. Preventive and therapeutic euphol treatment attenuates experimental colitis in mice. PloS one. 2011; 6(11):e27122. doi: 10.1371/journal.pone.0027122. [PMID: 22073270]
  • Zeng-jun Guo, Jian-feng Zuo, Xiao-qian Bo, Qi-shi Sun. [Study on chemical constituents of Euphorbia hylonoma hand. -Mazz]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Apr; 30(4):412-5. doi: ". [PMID: 17674791]
  • Han-li Ruan, Yue Zhang, Yong-hui Zhang, Hui-fang Pi, Ji-zhou Wu. [Studies on constituents from roots of Euphorbia hylonoma]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 May; 31(9):742-4. doi: ". [PMID: 17048682]
  • T Akihisa, J Ogihara, J Kato, K Yasukawa, M Ukiya, S Yamanouchi, K Oishi. Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase. Lipids. 2001 May; 36(5):507-12. doi: 10.1007/s11745-001-0750-4. [PMID: 11432464]
  • T Akihisa, K Yasukawa, Y Kimura, S Takase, S Yamanouchi, T Tamura. Triterpene alcohols from camellia and sasanqua oils and their anti-inflammatory effects. Chemical & pharmaceutical bulletin. 1997 Dec; 45(12):2016-23. doi: 10.1248/cpb.45.2016. [PMID: 9433772]