Cucurbitacin E (BioDeep_00000305797)

Main id: BioDeep_00000000046

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


acetic acid [(E,5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-3,11-diketo-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-4-keto-1,1-dimethyl-hex-2-enyl] ester

化学式: C32H44O8 (556.3036024)
中文名称: 葫芦素 E
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(C(=O)C4(C)C)O)[C@]3(C)C(=O)C[C@]12C)O)O
InChI: InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1

描述信息

Cucurbitacin e is a member of the class of compounds known as cucurbitacins. Cucurbitacins are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitacin e is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitacin e is a bitter tasting compound found in cucumber, muskmelon, and watermelon, which makes cucurbitacin e a potential biomarker for the consumption of these food products.
Cucurbitacin E is a natural compound which from Cucurbitaceae plants. Cucurbitacin E significantly suppresses the activity of the cyclin B1/CDC2 complex.
Cucurbitacin E is a natural compound which from Cucurbitaceae plants. Cucurbitacin E significantly suppresses the activity of the cyclin B1/CDC2 complex.

同义名列表

24 个代谢物同义名

Cucurbitacin E; acetic acid [(E,5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-3,11-diketo-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-4-keto-1,1-dimethyl-hex-2-enyl] ester; acetic acid [(5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-3,11-diketo-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-4-keto-1,1-dimethyl-hex-2-enyl] ester; acetic acid [(E,5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-1,1-dimethyl-4-oxohex-2-enyl] ester; acetic acid [(5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-1,1-dimethyl-4-oxohex-2-enyl] ester; [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxo-hept-3-en-2-yl] ethanoate; [(6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxo-hept-3-en-2-yl] ethanoate; [(E,5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-1,1-dimethyl-4-oxo-hex-2-enyl] acetate; [(E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate; [(5R)-5-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-1,1-dimethyl-4-oxo-hex-2-enyl] acetate; [(6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate; 19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-; 19-Nor-9.beta.,10.alpha.-lanosta-1,5,23-triene-3,11,22-trione, 2,16.alpha.,20,25-tetrahydroxy-9-methyl-, 25-acetate; .alpha.-Elaterine; .alpha.-Elaterin; ELATERIN, ALPHA; Cucurbitacine E; NCI60_000150; LMST01010107; 18444-66-1; NSC521775; C08797; α-Elaterin; α-Elaterine



数据库引用编号

14 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)

24 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

  • Guizhou Hu, Wenya Liu, Liyan Li. Identification and quantification of cucurbitacin in watermelon frost using molecular networking integrated with ultra-high-performance liquid chromatography-tandem mass spectrometry. Journal of separation science. 2023 Jun; ?(?):e2300019. doi: 10.1002/jssc.202300019. [PMID: 37269211]
  • Jinfang Zhang, Baht Aray, Yan Zhang, Yinglu Bai, Tao Yuan, Shilan Ding, Yanyu Xue, Xiulan Huang, Zhiyong Li. Synergistic effect of cucurbitacin E and myricetin on Anti-Non-Small cell lung cancer: Molecular mechanism and therapeutic potential. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Mar; 111(?):154619. doi: 10.1016/j.phymed.2022.154619. [PMID: 36706697]
  • Aydın Ş Tunçbilek, Serap Yalçın Azarkan, Fahriye Sümer Ercan. The Determination of Molecular and Toxicological Mechanisms of Cucurbitacine E in Model Organism Drosophila melanogaster and Various Cancer Cell Lines: Molecular modelling, docking and dynamic simulation studies. Current computer-aided drug design. 2022 Oct; ?(?):. doi: 10.2174/1573409919666221031112223. [PMID: 36321227]
  • Miwako Toyofuku, Daiki Fujinaga, Kazue Inaba, Tomoki Funahashi, Yuuta Fujikawa, Hideshi Inoue, Hiroshi Kataoka, Ryusuke Niwa, Hajime Ono. The plant-derived triterpenoid, cucurbitacin B, but not cucurbitacin E, inhibits the developmental transition associated with ecdysone biosynthesis in Drosophila melanogaster. Journal of insect physiology. 2021 10; 134(?):104294. doi: 10.1016/j.jinsphys.2021.104294. [PMID: 34389412]
  • Yushuang Liu, Guangying Chen, Xiaoyu Chen, Shi-Xin Chen, Li-She Gan, Tao Yuan. Colocynthenins A-D, Ring-A seco-Cucurbitane Triterpenoids from the Fruits of Citrullus colocynthis. Journal of natural products. 2018 09; 81(9):2115-2119. doi: 10.1021/acs.jnatprod.8b00461. [PMID: 30183289]
  • Lemeng Dong, Jacob Pollier, Jean-Etienne Bassard, Georgios Ntallas, Aldo Almeida, Eleni Lazaridi, Bekzod Khakimov, Philipp Arendt, Louisi Souza de Oliveira, Frédéric Lota, Alain Goossens, Franck Michoux, Søren Bak. Co-expression of squalene epoxidases with triterpene cyclases boosts production of triterpenoids in plants and yeast. Metabolic engineering. 2018 09; 49(?):1-12. doi: 10.1016/j.ymben.2018.07.002. [PMID: 30016654]
  • Zhibin Wang, Wenbo Zhu, Mingjie Gao, Chengcui Wu, Chunjuan Yang, Jing Yang, Gaosong Wu, Bingyou Yang, Haixue Kuang. Simultaneous determination of cucurbitacin B and cucurbitacin E in rat plasma by UHPLC-MS/MS: A pharmacokinetics study after oral administration of cucurbitacin tablets. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Oct; 1065-1066(?):63-69. doi: 10.1016/j.jchromb.2017.09.024. [PMID: 28946127]
  • Moazzameh Ramezani, Fatemeh Rahmani, Ali Dehestani. Comparison between the effects of potassium phosphite and chitosan on changes in the concentration of Cucurbitacin E and on antibacterial property of Cucumis sativus. BMC complementary and alternative medicine. 2017 Jun; 17(1):295. doi: 10.1186/s12906-017-1808-y. [PMID: 28583179]
  • Nicole Bajcsik, Rudolf Pfab, Jörg Pietsch. Simultaneous determination of cucurbitacin B, E, I and E-glucoside in plant material and body fluids by HPLC-MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 May; 1052(?):128-134. doi: 10.1016/j.jchromb.2017.03.030. [PMID: 28376351]
  • Jian Lu, TongGui Ding, Xuan Qin, MingYao Liu, Xin Wang. In vitro and in vivo evaluation of cucurbitacin E on rat hepatic CYP2C11 expression and activity using LC-MS/MS. Science China. Life sciences. 2017 Feb; 60(2):215-224. doi: 10.1007/s11427-015-4911-7. [PMID: 26354504]
  • Yan-Ling Wu, Yu-Jing Zhang, You-Li Yao, Zhi-Man Li, Xin Han, Li-Hua Lian, Yu-Qing Zhao, Ji-Xing Nan. Cucurbitacin E ameliorates hepatic fibrosis in vivo and in vitro through activation of AMPK and blocking mTOR-dependent signaling pathway. Toxicology letters. 2016 Sep; 258(?):147-158. doi: 10.1016/j.toxlet.2016.06.2102. [PMID: 27363783]
  • Bojan Jevtić, Neda Djedović, Suzana Stanisavljević, Jovana Despotović, Djordje Miljković, Gordana Timotijević. Cucurbitacin E Potently Modulates the Activity of Encephalitogenic Cells. Journal of agricultural and food chemistry. 2016 Jun; 64(24):4900-7. doi: 10.1021/acs.jafc.6b00951. [PMID: 27225664]
  • Qingyun Jia, Wenxiang Cheng, Ye Yue, Yipping Hu, Jian Zhang, Xiaohua Pan, Zhanwang Xu, Peng Zhang. Cucurbitacin E inhibits TNF-α-induced inflammatory cytokine production in human synoviocyte MH7A cells via suppression of PI3K/Akt/NF-κB pathways. International immunopharmacology. 2015 Dec; 29(2):884-890. doi: 10.1016/j.intimp.2015.08.026. [PMID: 26453509]
  • Tonggui Ding, Yuanjin Zhang, Ang Chen, Yu Tang, Mingyao Liu, Xin Wang. Effects of cucurbitacin e, a tetracyclic triterpene compound from Cucurbitaceae, on the pharmacokinetics and pharmacodynamics of warfarin in rats. Basic & clinical pharmacology & toxicology. 2015 May; 116(5):385-9. doi: 10.1111/bcpt.12329. [PMID: 25250504]
  • Y-C Hsu, M-J Chen, T-Y Huang. Inducement of mitosis delay by cucurbitacin E, a novel tetracyclic triterpene from climbing stem of Cucumis melo L., through GADD45γ in human brain malignant glioma (GBM) 8401 cells. Cell death & disease. 2014 Feb; 5(?):e1087. doi: 10.1038/cddis.2014.22. [PMID: 24577085]
  • Yanjie Kong, Jianchao Chen, Zhongmei Zhou, Houjun Xia, Ming-Hua Qiu, Ceshi Chen. Cucurbitacin E induces cell cycle G2/M phase arrest and apoptosis in triple negative breast cancer. PloS one. 2014; 9(7):e103760. doi: 10.1371/journal.pone.0103760. [PMID: 25072848]
  • Lamice Habib, Alia Jraij, Nathalie Khreich, Hatem Fessi, Catherine Charcosset, Hélène Greige-Gerges. Morphological and physicochemical characterization of liposomes loading cucurbitacin E, an anti-proliferative natural tetracyclic triterpene. Chemistry and physics of lipids. 2014 Jan; 177(?):64-70. doi: 10.1016/j.chemphyslip.2013.11.006. [PMID: 24291009]
  • Lamice Habib, Nathalie Khreich, Alia Jraij, Suzanne Abbas, Jacques Magdalou, Catherine Charcosset, Hélène Greige-Gerges. Preparation and characterization of liposomes incorporating cucurbitacin E, a natural cytotoxic triterpene. International journal of pharmaceutics. 2013 May; 448(1):313-9. doi: 10.1016/j.ijpharm.2013.03.027. [PMID: 23524087]
  • Pia M Sörensen, Roxana E Iacob, Marco Fritzsche, John R Engen, William M Brieher, Guillaume Charras, Ulrike S Eggert. The natural product cucurbitacin E inhibits depolymerization of actin filaments. ACS chemical biology. 2012 Sep; 7(9):1502-8. doi: 10.1021/cb300254s. [PMID: 22724897]
  • Siddig Ibrahim Abdelwahab, Loiy Elsir Ahmed Hassan, Hasnah Mohd Sirat, Sakina M Ahmed Yagi, Waleed S Koko, Syam Mohan, Manal Mohamed Elhassan Taha, Syahida Ahmad, Cheah Shiau Chuen, Putri Narrima, Mohd Mustafa Rais, A Hamid A Hadi. Anti-inflammatory activities of cucurbitacin E isolated from Citrullus lanatus var. citroides: role of reactive nitrogen species and cyclooxygenase enzyme inhibition. Fitoterapia. 2011 Dec; 82(8):1190-7. doi: 10.1016/j.fitote.2011.08.002. [PMID: 21871542]
  • Yanmin Dong, Binbin Lu, Xiaoli Zhang, Jing Zhang, Li Lai, Dali Li, Yuanyuan Wu, Yajuan Song, Jian Luo, Xiufeng Pang, Zhengfang Yi, Mingyao Liu. Cucurbitacin E, a tetracyclic triterpenes compound from Chinese medicine, inhibits tumor angiogenesis through VEGFR2-mediated Jak2-STAT3 signaling pathway. Carcinogenesis. 2010 Dec; 31(12):2097-104. doi: 10.1093/carcin/bgq167. [PMID: 20732905]
  • Myriam Saade, Jacques Magdalou, Naim Ouaini, Helene Greige-Gerges. Stability of cucurbitacin E in human plasma: chemical hydrolysis and role of plasma esterases. Biopharmaceutics & drug disposition. 2009 Oct; 30(7):389-97. doi: 10.1002/bdd.673. [PMID: 19688720]
  • Rony Abou-Khalil, Alia Jraij, Jacques Magdalou, Naïm Ouaini, Daniel Tome, Hélène Greige-Gerges. Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands. Journal of photochemistry and photobiology. B, Biology. 2009 Jun; 95(3):189-95. doi: 10.1016/j.jphotobiol.2009.03.005. [PMID: 19380237]
  • H Greige-Gerges, R Abou Khalil, R Chahine, C Haddad, W Harb, N Ouaini. Effect of cucurbitacins on bilirubin-albumin binding in human plasma. Life sciences. 2007 Jan; 80(6):579-85. doi: 10.1016/j.lfs.2006.10.005. [PMID: 17097690]
  • Hamta Madari, Robert S Jacobs. An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients. Journal of natural products. 2004 Aug; 67(8):1204-10. doi: 10.1021/np049953r. [PMID: 15332833]
  • Marc Litaudon, Christianne Gaspard, Thierry Sévenet. Morierinin: a new cytotoxic cucurbitacin from the leaves of Morierina montana Vieill. Natural product research. 2003 Aug; 17(4):229-33. doi: 10.1080/1057563021000042329. [PMID: 12822899]
  • Phyllis A W Martin, Michael Blackburn, Robert F W Schroder, Koharto Matsuo, Betty W Li. Stabilization of cucurbitacin E-glycoside, a feeding stimulant for diabroticite beetles, extracted from bitter Hawkesbury watermelon. Journal of insect science (Online). 2002; 2(?):19. doi: ". [PMID: 15455053]
  • R F Schroder, P A Martin, M M Athanas. Effect of a phloxine B-cucurbitacin bait on diabroticite beetles (Coleoptera: Chrysomelidae). Journal of economic entomology. 2001 Aug; 94(4):892-7. doi: 10.1603/0022-0493-94.4.892. [PMID: 11561848]
  • L L Musza, P Speight, S McElhiney, C J Barrow, A M Gillum, R Cooper, L M Killar. Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides. Journal of natural products. 1994 Nov; 57(11):1498-502. doi: 10.1021/np50113a004. [PMID: 7852999]
  • D LAVIE. The functional groupings of alpha-elaterin (cucurbitacin E). The Journal of pharmacy and pharmacology. 1958 Dec; 10(12):782. doi: 10.1111/j.2042-7158.1958.tb10375.x. [PMID: 13611647]
  • J N GILBERT, D W MATHIESON. The functional groupings of cucurbitacin E (alpha-elaterin). The Journal of pharmacy and pharmacology. 1958 Dec; 10(Supp):252-5T; discussion 255. doi: 10.1111/j.2042-7158.1958.tb10408.x. [PMID: 13611679]