elatericin B (BioDeep_00000000838)

 

Secondary id: BioDeep_00000287798

PANOMIX_OTCML-2023


代谢物信息卡片


(8S,9R,10R,13R,14S,16R,17R)-17-[(E,1R)-1,5-dihydroxy-1,5-dimethyl-2-oxo-hex-3-enyl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione

化学式: C30H42O7 (514.2930382)
中文名称: 葫芦素 I, 葫芦素I
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.22%

分子结构信息

SMILES: CC(C)(C1=CC[C@@]2([H])[C@@]3(C[C@@H](O)[C@@H]([C@]3(C4)C)[C@@](C)(O)C(/C=C/C(C)(O)C)=O)C)C(C(O)=C[C@@]1([H])[C@]2(C)C4=O)=O
InChI: InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1

描述信息

Cucurbitacin I is a cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22. It has a role as a plant metabolite and an antineoplastic agent. It is a cucurbitacin and a tertiary alpha-hydroxy ketone.
Cucurbitacin I is a natural product found in Elaeocarpus chinensis, Elaeocarpus hainanensis, and other organisms with data available.
A cucurbitacin that is 9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene substituted by hydroxy groups at positions 2, 16, 20 and 25 and oxo groups at positions 1, 11 and 22.
Cucurbitacin I is a natural selective inhibitor of JAK2/STAT3, with potent anti-cancer activity.

同义名列表

22 个代谢物同义名

(8S,9R,10R,13R,14S,16R,17R)-17-[(E,1R)-1,5-dihydroxy-1,5-dimethyl-2-oxo-hex-3-enyl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione; (8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione; (4R,9beta,16alpha,23E)-2,16,20,25-tetrahydroxy-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-2,5,23-triene-1,11,22-trione; 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.,23E)-; 19-Norlanosta-1,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9.beta.,10.alpha.,16.alpha.)- (VA; 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)- (VAN); 19-Norlanosta-1,5,23-triene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (9beta,10alpha,16alpha)-; 2,16alpha,20,25-Tetrahydroxy-9beta-methyl-10alpha-19-norlanosta-1,5,23(E)-triene-3,11,22-trione; 19-Nor-9-beta,10-alpha-lanosta-1,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-; (9?,10?,16?,23E)-2,16,20,25-Tetrahydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione; 2,16,20,25-Terahydroxycucurbita-1,5,23-triene-3,11,22-trione - Iberis umbellata (candytuft); 19-nor-9.beta.,5,23-triene-3,11,22-trione, 9-methyl-2,16,20,25-tetrahydroxy-; Cucurbitacin I (Elatericin B); 1,2-Dehydroelatericin A; CUCURBITACCINE (I); Cucurbitacine (I); Cucurbitacin I; elatericin B; ST 30:6;O7; NSC521777; JSI-124; NSC-521777



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)

23 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

  • Nuray Üremiş, Muhammed Mehdi Üremiş, Yılmaz Çiğremiş, Emir Tosun, Ahmet Baysar, Yusuf Türköz. Cucurbitacin I exhibits anticancer efficacy through induction of apoptosis and modulation of JAK/STAT3, MAPK/ERK, and AKT/mTOR signaling pathways in HepG2 cell line. Journal of food biochemistry. 2022 10; 46(10):e14333. doi: 10.1111/jfbc.14333. [PMID: 35866877]
  • Xianjing Zhang, Huihui Li, Wenqiong Wang, Tong Chen, Lijiang Xuan. Lipid-Lowering Activities of Cucurbitacins Isolated from Trichosanthes cucumeroides and Their Synthetic Derivatives. Journal of natural products. 2020 12; 83(12):3536-3544. doi: 10.1021/acs.jnatprod.0c00364. [PMID: 33269591]
  • Alexandria Turner, Danielle R Bond, Quan V Vuong, Anita Chalmers, Emma L Beckett, Judith Weidenhofer, Christopher J Scarlett. Elaeocarpus reticulatus fruit extracts reduce viability and induce apoptosis in pancreatic cancer cells in vitro. Molecular biology reports. 2020 Mar; 47(3):2073-2084. doi: 10.1007/s11033-020-05307-8. [PMID: 32065323]
  • 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]
  • T Pan, L Zhong, S Wu, Y Cao, Q Yang, Z Cai, X Cai, W Zhao, N Ma, W Zhang, H Zhang, J Zhou. 17β-Oestradiol enhances the expansion and activation of myeloid-derived suppressor cells via signal transducer and activator of transcription (STAT)-3 signalling in human pregnancy. Clinical and experimental immunology. 2016 07; 185(1):86-97. doi: 10.1111/cei.12790. [PMID: 26969967]
  • Meryem Sari-Hassoun, Marie-Jeanne Clement, Imane Hamdi, Guillaume Bollot, Cyril Bauvais, Vandana Joshi, Flavio Toma, Andrea Burgo, Michel Cailleret, Martha Cecilia Rosales-Hernández, Martha Edith Macias Pérez, Daoudi Chabane-Sari, Patrick A Curmi. Cucurbitacin I elicits the formation of actin/phospho-myosin II co-aggregates by stimulation of the RhoA/ROCK pathway and inhibition of LIM-kinase. Biochemical pharmacology. 2016 Feb; 102(?):45-63. doi: 10.1016/j.bcp.2015.12.013. [PMID: 26707799]
  • Guang Yuan, Shao-Feng Yan, Hao Xue, Ping Zhang, Jin-Tang Sun, Gang Li. Cucurbitacin I induces protective autophagy in glioblastoma in vitro and in vivo. The Journal of biological chemistry. 2014 Apr; 289(15):10607-10619. doi: 10.1074/jbc.m113.528760. [PMID: 24599950]
  • Cho-Rong Seo, Dong Kwon Yang, No-Joon Song, Ui Jeong Yun, A-Ryeong Gwon, Dong-Gyu Jo, Jae Youl Cho, Keejung Yoon, Jee-Yin Ahn, Chu Won Nho, Woo Jin Park, Seung Yul Yang, Kye Won Park. Cucurbitacin B and cucurbitacin I suppress adipocyte differentiation through inhibition of STAT3 signaling. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Feb; 64(?):217-24. doi: 10.1016/j.fct.2013.11.040. [PMID: 24316209]
  • Li Pan, Yeonjoong Yong, Ye Deng, Daniel D Lantvit, Tran Ngoc Ninh, Heebyung Chai, Esperanza J Carcache de Blanco, Djaja D Soejarto, Steven M Swanson, A Douglas Kinghorn. Isolation, structure elucidation, and biological evaluation of 16,23-epoxycucurbitacin constituents from Eleaocarpus chinensis. Journal of natural products. 2012 Mar; 75(3):444-52. doi: 10.1021/np200879p. [PMID: 22239601]
  • David A Knecht, Rebecca A LaFleur, Alem W Kahsai, Christian E Argueta, Anwar B Beshir, Gabriel Fenteany. Cucurbitacin I inhibits cell motility by indirectly interfering with actin dynamics. PloS one. 2010 Nov; 5(11):e14039. doi: 10.1371/journal.pone.0014039. [PMID: 21124831]
  • 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]
  • Ommoleila Molavi, Zengshuan Ma, Samar Hamdy, Afsaneh Lavasanifar, John Samuel. Immunomodulatory and anticancer effects of intra-tumoral co-delivery of synthetic lipid A adjuvant and STAT3 inhibitor, JSI-124. Immunopharmacology and immunotoxicology. 2009 Jun; 31(2):214-21. doi: 10.1080/08923970802380452. [PMID: 18798092]
  • Jian-Chao Chen, Gao-Hong Zhang, Zhong-Quan Zhang, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Kai-Bei Yu. Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity. Journal of natural products. 2008 Jan; 71(1):153-5. doi: 10.1021/np0704396. [PMID: 18088099]
  • 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]
  • Naoko Yoshida, Mariya Koizumi, Isao Adachi, Junichi Kawakami. Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2006 Dec; 44(12):2033-9. doi: 10.1016/j.fct.2006.07.003. [PMID: 16904803]
  • Angela Graness, Valeria Poli, Margarete Goppelt-Struebe. STAT3-independent inhibition of lysophosphatidic acid-mediated upregulation of connective tissue growth factor (CTGF) by cucurbitacin I. Biochemical pharmacology. 2006 Jun; 72(1):32-41. doi: 10.1016/j.bcp.2006.04.001. [PMID: 16707113]
  • Ommoleila Molavi, Anooshirvan Shayeganpour, Vishwa Somayaji, Samar Hamdy, Dion R Brocks, Afsaneh Lavasanifar, Glen S Kwon, John Samuel. Development of a sensitive and specific liquid chromatography/mass spectrometry method for the quantification of cucurbitacin I (JSI-124) in rat plasma. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2006; 9(2):158-64. doi: . [PMID: 16959185]
  • 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]
  • Michelle A Blaskovich, Jiazhi Sun, Alan Cantor, James Turkson, Richard Jove, Saïd M Sebti. Discovery of JSI-124 (cucurbitacin I), a selective Janus kinase/signal transducer and activator of transcription 3 signaling pathway inhibitor with potent antitumor activity against human and murine cancer cells in mice. Cancer research. 2003 Mar; 63(6):1270-9. doi: . [PMID: 12649187]
  • 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]