Tefestrol (BioDeep_00000395612)

Main id: BioDeep_00000179035

 

PANOMIX_OTCML-2023


代谢物信息卡片


Benzoic acid, 4-hydroxy-, 1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester, (3R-(3alpha,3abeta,4beta,8aalpha))-

化学式: C22H30O4 (358.214398)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CCC2(CCC(C2C(C1)OC(=O)C3=CC=C(C=C3)O)(C(C)C)O)C
InChI: InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1

描述信息

Ferutinine is a natural product found in Ferula jaeschkeana, Ferula sinaica, and other organisms with data available.
Ferutinin, a natural terpenoid compound, is an estrogen receptor ERα agonist and estrogen ERβ-receptor agonist/antagonist with IC50s of 33.1 nM and 180.5 nM, respectively. Ferutinin acts as an electrogenic Ca2+-ionophore that increases calcium permeability of lipid bilayer membranes, mitochondria. Ferutinin possesses estrogenic, antitumor, antibacterial and antiinflammatory activities[1][2].

同义名列表

15 个代谢物同义名

Benzoic acid, 4-hydroxy-, 1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester, (3R-(3alpha,3abeta,4beta,8aalpha))-; Benzoic acid, 4-hydroxy-, (3R,3aS,4S,8aR)-1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester; (3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate; [(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate; 3-Hydroxy-6,8a-dimethyl-3-(propan-2-yl)-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-hydroxybenzoate; 4-oxy-6-(4-oxybezoyloxy)dauc-8,9-en; Jaeschkeanadiol p-hydroxy benzoate; Jaeschkeanadiol p-hydroxybenzoate; Ferutinin, >=98\\% (HPLC); From Ferula tingiatana; Ferutinine; Tefestrol; Ferutinin; 4mg7; Ferutinine



数据库引用编号

7 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)

1 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

  • Roberta Macrì, Irene Bava, Federica Scarano, Rocco Mollace, Vincenzo Musolino, Micaela Gliozzi, Marta Greco, Daniela Foti, Luigi Tucci, Jessica Maiuolo, Cristina Carresi, Annamaria Tavernese, Ernesto Palma, Carolina Muscoli, Vincenzo Mollace. In Vitro Evaluation of Ferutinin Rich-Ferula communis L., ssp. glauca, Root Extract on Doxorubicin-Induced Cardiotoxicity: Antioxidant Properties and Cell Cycle Modulation. International journal of molecular sciences. 2023 Aug; 24(16):. doi: 10.3390/ijms241612735. [PMID: 37628916]
  • Abdel Mohsen M Hammam, Amira K Elmotayam, Walied M Elnattat, Gamal A Ali, Abd Elnaser M Madbouly, Rabab M El Khatteb, Mohamed F Abdelhameed, Amal H Ali, Sumera Qasim, Shaimaa R Ahmed. Assessment of Ferula hermonis Boiss fertility effects in immature female rats supported by quantification of ferutinin via HPLC and molecular docking. Journal of ethnopharmacology. 2022 May; 289(?):115062. doi: 10.1016/j.jep.2022.115062. [PMID: 35114339]
  • Zahra Mahmoudi, Abbas Saidi, Mehrdad Iranshahi, Neda Dadgar, Arezou Azizsoltani, Sahar Behzad, Ladan Mahmoudi, Masoud Soleimani, Hamed Parsa Khankandi. In vitro evaluation of ferutinin on proliferation and osteogenesis differentiation in human unrestricted Somatic stem cells. Steroids. 2021 08; 172(?):108862. doi: 10.1016/j.steroids.2021.108862. [PMID: 34010709]
  • Jessica Maiuolo, Irene Bava, Cristina Carresi, Micaela Gliozzi, Vincenzo Musolino, Miriam Scicchitano, Roberta Macri, Francesca Oppedisano, Federica Scarano, Maria Caterina Zito, Francesca Bosco, Stefano Ruga, Saverio Nucera, Sara Ilari, Ernesto Palma, Carolina Muscoli, Vincenzo Mollace. The Effect of Ferula communis Extract in Escherichia coli Lipopolysaccharide-Induced Neuroinflammation in Cultured Neurons and Oligodendrocytes. International journal of molecular sciences. 2021 Jul; 22(15):. doi: 10.3390/ijms22157910. [PMID: 34360675]
  • Shahrzad Naji Reyhani Garmroudi, Ehsan Karimi, Ehsan Oskoueian, Masoud Homayouni-Tabrizi, Mehrdad Iranshahi. Ferutinin: A phytoestrogen from ferula and its anticancer, antioxidant, and toxicity properties. Journal of biochemical and molecular toxicology. 2021 Apr; 35(4):e22713. doi: 10.1002/jbt.22713. [PMID: 33501774]
  • Roberta Macrì, Vincenzo Musolino, Micaela Gliozzi, Cristina Carresi, Jessica Maiuolo, Saverio Nucera, Miriam Scicchitano, Francesca Bosco, Federica Scarano, Stefano Ruga, Maria Caterina Zito, Lorenza Guarnieri, Ezio Bombardelli, Vincenzo Mollace. Ferula L. Plant Extracts and Dose-Dependent Activity of Natural Sesquiterpene Ferutinin: From Antioxidant Potential to Cytotoxic Effects. Molecules (Basel, Switzerland). 2020 Dec; 25(23):. doi: 10.3390/molecules25235768. [PMID: 33297504]
  • Mostafa Alilou, Dya Fita Dibwe, Stefan Schwaiger, Mojtaba Khodami, Jakob Troppmair, Suresh Awale, Hermann Stuppner. Antiausterity Activity of Secondary Metabolites from the Roots of Ferula hezarlalehzarica against the PANC-1 Human Pancreatic Cancer Cell Line. Journal of natural products. 2020 04; 83(4):1099-1106. doi: 10.1021/acs.jnatprod.9b01109. [PMID: 32163286]
  • Maria E Solesio, Luis C Garcia Del Molino, Pia A Elustondo, Catherine Diao, Joshua C Chang, Evgeny V Pavlov. Inorganic polyphosphate is required for sustained free mitochondrial calcium elevation, following calcium uptake. Cell calcium. 2020 03; 86(?):102127. doi: 10.1016/j.ceca.2019.102127. [PMID: 31954928]
  • Rémi Safi, Marwan El-Sabban, Fadia Najjar. Ferula hermonis: A Review of Current Use and Pharmacological Studies of its Sesquiterpene Ester Ferutinin. Current drug targets. 2020; 21(5):499-508. doi: 10.2174/1389450120666191029155053. [PMID: 31663476]
  • Faegheh Farhadi, Saba Soltani, Satar Saberi, Mehrdad Iranshahi. A qHNMR method for simultaneous quantification of terpenoids from Ferula ovina (Boiss.) Boiss roots. Journal of pharmaceutical and biomedical analysis. 2019 Aug; 172(?):120-125. doi: 10.1016/j.jpba.2019.04.039. [PMID: 31035093]
  • Hoda Zare Mirakabad, Mohammad Farsi, Saeed Malekzadeh Shafaroudi, Abdolreza Bagheri, Mehrdad Iranshahi, Nasrin Moshtaghi. Comparison the Effect of Ferutinin and 17β-Estradiol on Bone Mineralization of Developing Zebrafish (Danio rerio) Larvae. International journal of molecular sciences. 2019 Mar; 20(6):. doi: 10.3390/ijms20061507. [PMID: 30917511]
  • Tatsiana Ilyich, Oksana Charishnikova, Szymon Sekowski, Maria Zamaraeva, Vitali Cheshchevik, Iosif Dremza, Nina Cheshchevik, Lyudmila Kiryukhina, Elena Lapshina, Ilya Zavodnik. Ferutinin Induces Membrane Depolarization, Permeability Transition Pore Formation, and Respiration Uncoupling in Isolated Rat Liver Mitochondria by Stimulation of Ca2+-Permeability. The Journal of membrane biology. 2018 08; 251(4):563-572. doi: 10.1007/s00232-018-0032-0. [PMID: 29594529]
  • Zohreh Sattar, Mehrdad Iranshahi. Phytochemistry and Pharmacology of Ferula hermonis Boiss. - A Review. Drug research. 2017 Aug; 67(8):437-446. doi: 10.1055/s-0043-109100. [PMID: 28521374]
  • A Dubis, M V Zamaraeva, L Siergiejczyk, O Charishnikova, V Shlyonsky. Ferutinin as a Ca(2+) complexone: lipid bilayers, conductometry, FT-IR, NMR studies and DFT-B3LYP calculations. Dalton transactions (Cambridge, England : 2003). 2015 Oct; 44(37):16506-15. doi: 10.1039/c4dt03892d. [PMID: 26331156]
  • Maryam Moghaddam Matin, Hossein Nakhaeizadeh, Ahamd Reza Bahrami, Mehrdad Iranshahi, Nahid Arghiani, Fatemeh Behnam Rassouli. Ferutinin, an apoptosis inducing terpenoid from Ferula ovina. Asian Pacific journal of cancer prevention : APJCP. 2014; 15(5):2123-8. doi: 10.7314/apjcp.2014.15.5.2123. [PMID: 24716944]
  • Minghui Gao, Sze Yui Wong, Pui Man Lau, Siu Kai Kong. Ferutinin induces in vitro eryptosis/erythroptosis in human erythrocytes through membrane permeabilization and calcium influx. Chemical research in toxicology. 2013 Aug; 26(8):1218-28. doi: 10.1021/tx400127w. [PMID: 23848973]
  • Abdel-Hadi Al-Ja'fari, Roser Vila, Blanca Freixa, Joan Costa, Salvador Cañigueral. Antifungal compounds from the rhizome and roots of Ferula hermonis. Phytotherapy research : PTR. 2013 Jun; 27(6):911-5. doi: 10.1002/ptr.4806. [PMID: 22927102]
  • Zedan Zeid Ibraheim, Wael M Abdel-Mageed, Huanqin Dai, Hui Guo, Lixin Zhang, Marcel Jaspars. Antimicrobial antioxidant daucane sesquiterpenes from Ferula hermonis Boiss. Phytotherapy research : PTR. 2012 Apr; 26(4):579-86. doi: 10.1002/ptr.3609. [PMID: 21953875]
  • Ehab A Abourashed, Ahmed M Galal, Atef M Shibl. Antimycobacterial activity of ferutinin alone and in combination with antitubercular drugs against a rapidly growing surrogate of Mycobacterium tuberculosis. Natural product research. 2011 Jul; 25(12):1142-9. doi: 10.1080/14786419.2010.481623. [PMID: 21442547]
  • Afaf Geroushi, Abdurazag A Auzi, Abdalla Salem Elhwuegi, Fawzi Elzawam, Akram Elsherif, Lutfun Nahar, Satyajit D Sarker. Antiinflammatory sesquiterpenes from the root oil of Ferula hermonis. Phytotherapy research : PTR. 2011 May; 25(5):774-7. doi: 10.1002/ptr.3324. [PMID: 21520471]
  • Maria Zamaraeva, Oksana Charishnikova, Ashraf Saidkhodjaev, Valery Isidorov, Magdalena Granosik, Marcin Różalski, Cezary Watała. Calcium mobilization by the plant estrogen ferutinin does not induce blood platelet aggregation. Pharmacological reports : PR. 2010 Nov; 62(6):1117-26. doi: 10.1016/s1734-1140(10)70374-1. [PMID: 21273669]
  • Carla Palumbo, Marzia Ferretti, Laura Bertoni, Francesco Cavani, Elisa Resca, Barbara Casolari, Gianluca Carnevale, Manuela Zavatti, Caterina Montanari, Augusta Benelli, Paola Zanoli. Influence of ferutinin on bone metabolism in ovariectomized rats. I: role in preventing osteoporosis. Journal of bone and mineral metabolism. 2009; 27(5):538-45. doi: 10.1007/s00774-009-0070-x. [PMID: 19333679]
  • Mario Dell'Agli, Germana V Galli, Esther Dal Cero, Federica Belluti, Riccardo Matera, Elisa Zironi, Giampiero Pagliuca, Enrica Bosisio. Potent inhibition of human phosphodiesterase-5 by icariin derivatives. Journal of natural products. 2008 Sep; 71(9):1513-7. doi: 10.1021/np800049y. [PMID: 18778098]
  • H Greige-Gerges, Y Diab, J Farah, J Magdalou, C Haddad, N Ouaini. Ferutinin stability in human plasma and interaction with human serum albumin. Biopharmaceutics & drug disposition. 2008 Mar; 29(2):83-9. doi: 10.1002/bdd.589. [PMID: 18050264]
  • P Zanoli, M Rivasi, M Zavatti, F Brusiani, F Vezzalini, M Baraldi. Activity of single components of Ferula hermonis on male rat sexual behavior. International journal of impotence research. 2005 Nov; 17(6):513-8. doi: 10.1038/sj.ijir.3901346. [PMID: 15920458]
  • Amélie Lhuillier, Nicolas Fabre, Edmond Cheble, Fathi Oueida, Séverine Maurel, Alexis Valentin, Isabelle Fourasté, Claude Moulis. Daucane sesquiterpenes from Ferula hermonis. Journal of natural products. 2005 Mar; 68(3):468-71. doi: 10.1021/np049652h. [PMID: 15787464]
  • Giovanni Appendino, Paola Spagliardi, Giancarlo Cravotto, Victoria Pocock, Stuart Milligan. Daucane phytoestrogens: a structure-activity study. Journal of natural products. 2002 Nov; 65(11):1612-5. doi: 10.1021/np0201671. [PMID: 12444685]
  • Kazuhiro Ikeda, Yukitomo Arao, Hiroko Otsuka, Satoshi Nomoto, Hyogo Horiguchi, Shigeaki Kato, Fujio Kayama. Terpenoids found in the umbelliferae family act as agonists/antagonists for ER(alpha) and ERbeta: differential transcription activity between ferutinine-liganded ER(alpha) and ERbeta. Biochemical and biophysical research communications. 2002 Feb; 291(2):354-60. doi: 10.1006/bbrc.2002.6446. [PMID: 11846412]
  • A Y Abramov, M V Zamaraeva, A I Hagelgans, R R Azimov, O V Krasilnikov. Influence of plant terpenoids on the permeability of mitochondria and lipid bilayers. Biochimica et biophysica acta. 2001 May; 1512(1):98-110. doi: 10.1016/s0005-2736(01)00307-8. [PMID: 11334628]
  • A M Galal, E A Abourashed, S A Ross, M A ElSohly, M S Al-Said, F S El-Feraly. Daucane sesquiterpenes from Ferula hermonis. Journal of natural products. 2001 Mar; 64(3):399-400. doi: 10.1021/np000526x. [PMID: 11277769]
  • M V Zamaraeva, A I Hagelgans, A Y Abramov, V I Ternovsky, P G Merzlyak, B A Tashmukhamedov, A I Saidkhodzjaev. Ionophoretic properties of ferutinin. Cell calcium. 1997 Oct; 22(4):235-41. doi: 10.1016/s0143-4160(97)90062-2. [PMID: 9481474]