Ferruginol (BioDeep_00000000957)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-, (4BS-TRANS)-

化学式: C20H30O (286.229653)
中文名称: 弥罗松酚, 铁锈醇
谱图信息: 最多检出来源 Viridiplantae(plant) 20.58%

分子结构信息

SMILES: CC(C)C1=C(C=C2C(=C1)CCC3C2(CCCC3(C)C)C)O
InChI: InChI=1S/C20H30O/c1-13(2)15-11-14-7-8-18-19(3,4)9-6-10-20(18,5)16(14)12-17(15)21/h11-13,18,21H,6-10H2,1-5H3/t18-,20+/m0/s1

描述信息

Ferruginol is an abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12. It has a role as an antineoplastic agent, an antibacterial agent, a protective agent and a plant metabolite. It is an abietane diterpenoid, a member of phenols, a carbotricyclic compound and a meroterpenoid.
Ferruginol is a natural product found in Calocedrus macrolepis, Teucrium polium, and other organisms with data available.
An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.

同义名列表

22 个代谢物同义名

3-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-, (4BS-TRANS)-; 3-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bS,8aS)-; (4BS,8AS)-4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-2-(1-METHYLETHYL)-3-PHENANTHRENOL; (4BS,8AS)-4B,8,8-TRIMETHYL-2-(PROPAN-2-YL)-4B,5,6,7,8,8A,9,10-OCTAHYDROPHENANTHREN-3-OL; (4bs,8as)-4b,8,8-trimethyl-2-propane-2-yl-5,6,7,8a,9,10-hexa hydrophenanthren-3-ol; (4bS,8aS)-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol; Podocarpa-8,11,13-trien-12-ol, 13-isopropyl-; Abieta-9(11),8(14),12-trien-12-ol #; 12-hydroxyabieta-8,11,13-triene; QXNWVJOHUAQHLM-AZUAARDMSA-N; abieta-8,11,13-trien-12-ol; 8,11,13-abietatrien-12-ol; trans-Ferruginol; UNII-N2CMM6X37M; (+)-Ferruginol; MEGxp0_000699; ACon1_000701; N2CMM6X37M; Ferruginol; AC1L9C4T; jm5b01461, Compound 91; Ferruginol



数据库引用编号

21 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

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • carnosate bioynthesis: 11-hydroxyferruginol + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H+ + H2O + an oxidized [NADPH-hemoprotein reductase] + carnosate

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

  • carnosate bioynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + ferruginol ⟶ 11-hydroxyferruginol + H2O + an oxidized [NADPH-hemoprotein reductase]
  • carnosate bioynthesis: H+ + NADPH + O2 + abietatriene ⟶ H2O + NADP+ + ferruginol

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

310 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

  • Mihayl Varbanov, Stéphanie Philippot, Miguel A González-Cardenete. Anticoronavirus Evaluation of Antimicrobial Diterpenoids: Application of New Ferruginol Analogues. Viruses. 2023 06; 15(6):. doi: 10.3390/v15061342. [PMID: 37376641]
  • Zuying Du, Ziqiu Peng, Hui Yang, Haisheng Wu, Jie Sun, Lili Huang. Identification and functional characterization of three cytochrome P450 genes for the abietane diterpenoid biosynthesis in Isodon lophanthoides. Planta. 2023 Mar; 257(5):90. doi: 10.1007/s00425-023-04125-z. [PMID: 36991182]
  • Xu Chen, Tiantian Liu, Qiyan Wang, Hui Wang, Siming Xue, Qianqian Jiang, Junjun Li, Chun Li, Wei Wang, Yong Wang. Synergistic Effects of Ginsenoside Rb3 and Ferruginol in Ischemia-Induced Myocardial Infarction. International journal of molecular sciences. 2022 Dec; 23(24):. doi: 10.3390/ijms232415935. [PMID: 36555577]
  • Roméo Arago Dougué Kentsop, Valeria Iobbi, Giuliana Donadio, Barbara Ruffoni, Nunziatina De Tommasi, Angela Bisio. Abietane Diterpenoids from the Hairy Roots of Salvia corrugata. Molecules (Basel, Switzerland). 2021 Aug; 26(17):. doi: 10.3390/molecules26175144. [PMID: 34500582]
  • Xudong Zhang, Xiaojiang Li, Chunlan Wang, Haijun Li, Lijun Wang, Yu Chen, Jingbin Feng, Sulaiman Ali Alharbi, Yue Deng. Ameliorative effect of ferruginol on isoprenaline hydrochloride-induced myocardial infarction in rats. Environmental toxicology. 2021 Feb; 36(2):249-256. doi: 10.1002/tox.23030. [PMID: 32946155]
  • Zahra Sadeghi, Milena Masullo, Antonietta Cerulli, Filomena Nazzaro, Mahdi Moridi Farimani, Sonia Piacente. Terpenoid Constituents of Perovskia artemisioides Aerial Parts with Inhibitory Effects on Bacterial Biofilm Growth. Journal of natural products. 2021 01; 84(1):26-36. doi: 10.1021/acs.jnatprod.0c00832. [PMID: 33378620]
  • Derya Bakir, Mehmet Akdeniz, Abdulselam Ertas, Mustafa A Yilmaz, Ismail Yener, Mehmet Firat, Ufuk Kolak. A GC-MS method validation for quantitative investigation of some chemical markers in Salvia hypargeia Fisch. & C.A. Mey. of Turkey: Enzyme inhibitory potential of ferruginol. Journal of food biochemistry. 2020 09; 44(9):e13350. doi: 10.1111/jfbc.13350. [PMID: 32686189]
  • Yaping Mao, Ying Ma, Tong Chen, Xiaohui Ma, Yanqin Xu, Junling Bu, Qishuang Li, Baolong Jin, Yanan Wang, Yong Li, Guanghong Cui, Yujun Zhao, Jinfu Tang, Ye Shen, Changjiangsheng Lai, Wen Zeng, Min Chen, Juan Guo, Luqi Huang. Functional Integration of Two CYP450 Genes Involved in Biosynthesis of Tanshinones for Improved Diterpenoid Production by Synthetic Biology. ACS synthetic biology. 2020 07; 9(7):1763-1770. doi: 10.1021/acssynbio.0c00136. [PMID: 32551504]
  • Francielle T G Sousa, Cristina Nunes, Camila Malta Romano, Ester Cerdeira Sabino, Miguel Angel González-Cardenete. Anti-Zika virus activity of several abietane-type ferruginol analogues. Revista do Instituto de Medicina Tropical de Sao Paulo. 2020; 62(?):e97. doi: 10.1590/s1678-9946202062097. [PMID: 33295481]
  • Guoqing Luo, Jingjing Zhou, Guanjie Li, Ningdong Hu, Xu Xia, Haibo Zhou. Ferruginol Diterpenoid Selectively Inhibits Human Thyroid Cancer Growth by Inducing Mitochondrial Dependent Apoptosis, Endogenous Reactive Oxygen Species (ROS) Production, Mitochondrial Membrane Potential Loss and Suppression of Mitogen-Activated Protein Kinase (MAPK) and PI3K/AKT Signaling Pathways. Medical science monitor : international medical journal of experimental and clinical research. 2019 04; 25(?):2935-2942. doi: 10.12659/msm.914348. [PMID: 31005958]
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  • Łukasz Kuźma, Monika Derda, Edward Hadaś, Halina Wysokińska. Abietane diterpenoids from Salvia sclarea transformed roots as growth inhibitors of pathogenic Acanthamoeba spp. Parasitology research. 2015 Jan; 114(1):323-7. doi: 10.1007/s00436-014-4211-3. [PMID: 25382125]
  • Shang-Tse Ho, Yu-Tang Tung, Yueh-Hsiung Kuo, Chi-Chen Lin, Jyh-Horng Wu. Ferruginol inhibits non-small cell lung cancer growth by inducing caspase-associated apoptosis. Integrative cancer therapies. 2015 Jan; 14(1):86-97. doi: 10.1177/1534735414555806. [PMID: 25355727]
  • Miguel A González, Julie Clark, Michele Connelly, Fatima Rivas. Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group. Bioorganic & medicinal chemistry letters. 2014 Nov; 24(22):5234-7. doi: 10.1016/j.bmcl.2014.09.061. [PMID: 25316317]
  • Raymond Muganga, Luc Angenot, Monique Tits, Michel Frédérich. In vitro and in vivo antiplasmodial activity of three Rwandan medicinal plants and identification of their active compounds. Planta medica. 2014 Apr; 80(6):482-9. doi: 10.1055/s-0034-1368322. [PMID: 24710900]
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  • Fang Yao, De-Wu Zhang, Gui-Wu Qu, Gui-Sheng Li, Sheng Jun Dai. New abietane norditerpenoid from Salvia miltiorrhiza with cytotoxic activities. Journal of Asian natural products research. 2012; 14(9):913-7. doi: 10.1080/10286020.2012.699962. [PMID: 22924543]
  • Mark B Yunker, Cara L Lachmuth, Walter J Cretney, Brian R Fowler, Neil Dangerfield, Linda White, Peter S Ross. Biota: sediment partitioning of aluminium smelter related PAHs and pulp mill related diterpenes by intertidal clams at Kitimat, British Columbia. Marine environmental research. 2011 Sep; 72(3):105-26. doi: 10.1016/j.marenvres.2011.06.004. [PMID: 21788067]
  • M Fronza, R Murillo, S Ślusarczyk, M Adams, M Hamburger, B Heinzmann, S Laufer, I Merfort. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica. Bioorganic & medicinal chemistry. 2011 Aug; 19(16):4876-81. doi: 10.1016/j.bmc.2011.06.067. [PMID: 21775156]
  • Cristina Theoduloz, Mariano Walter Pertino, Jaime A Rodríguez, Guillermo Schmeda-Hirschmann. Gastroprotective effect and cytotoxicity of carnosic acid derivatives. Planta medica. 2011 Jun; 77(9):882-7. doi: 10.1055/s-0030-1250648. [PMID: 21246485]
  • Hui-Ling Chen, Kai-Wei Lin, Kim-Hong Gan, Jih-Pyang Wang, Shen-Jeu Won, Chun-Nan Lin. New diterpenoids and cytotoxic and anti-inflammatory diterpenoids from Amentotaxus formosana. Fitoterapia. 2011 Mar; 82(2):219-24. doi: 10.1016/j.fitote.2010.10.002. [PMID: 21055452]
  • Morio Iijima, Tomoharu Yoshida, Toshiyuki Kato, Michio Kawasaki, Takamasa Watanabe, Sutharsan Somasundaram. Visualization of lateral water transport pathways in soybean by a time of flight-secondary ion mass spectrometry cryo-system. Journal of experimental botany. 2011 Mar; 62(6):2179-88. doi: 10.1093/jxb/erq418. [PMID: 21209027]
  • Angelo Aquino, Grazia Graziani, Ornella Franzese, Salvatore P Prete, Enzo Bonmassar, Laura Bonmassar, Stefania D'Atri. Exogenous control of the expression of Group I CD1 molecules competent for presentation of microbial nonpeptide antigens to human T lymphocytes. Clinical & developmental immunology. 2011; 2011(?):790460. doi: 10.1155/2011/790460. [PMID: 21603161]
  • Olayinka Aiyegoro, Adekanmi Adewusi, Sunday Oyedemi, David Akinpelu, Anthony Okoh. Interactions of antibiotics and methanolic crude extracts of Afzelia Africana (Smith.) against drug resistance bacterial isolates. International journal of molecular sciences. 2011; 12(7):4477-503. doi: 10.3390/ijms12074477. [PMID: 21845091]
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  • Yuhui Wei, Junquan He, Hongyan Qin, Xin'an Wu, Xiaojun Yao. Determination of ferruginol in rat plasma via high-performance liquid chromatography and its application in pharmacokinetics study. Biomedical chromatography : BMC. 2009 Oct; 23(10):1116-20. doi: 10.1002/bmc.1232. [PMID: 19444795]
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  • Julio C Herrera, Graciela Troncone, Diana Henríquez, Neudo Urdaneta. Trypanocidal activity of abietane diterpenoids from the roots of Craniolaria annua. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Nov; 63(11-12):821-9. doi: 10.1515/znc-2008-11-1207. [PMID: 19227829]
  • Wen-Hsin Li, Shang-Tzen Chang, Shan-Chwen Chang, Hui-Ting Chang. Isolation of antibacterial diterpenoids from Cryptomeria japonica bark. Natural product research. 2008; 22(12):1085-93. doi: 10.1080/14786410802267510. [PMID: 18780250]
  • Wei-Chun Tu, Sheng-Yang Wang, Shih-Chang Chien, Feng-Min Lin, Li-Ru Chen, Chih-Yang Chiu, Pei-Wen Hsiao. Diterpenes from Cryptomeria japonica inhibit androgen receptor transcriptional activity in prostate cancer cells. Planta medica. 2007 Oct; 73(13):1407-9. doi: 10.1055/s-2007-990233. [PMID: 17924310]
  • Chih-Chun Wen, Yueh-Hsiung Kuo, Jia-Tsrong Jan, Po-Huang Liang, Sheng-Yang Wang, Hong-Gi Liu, Ching-Kuo Lee, Shang-Tzen Chang, Chih-Jung Kuo, Shoei-Sheng Lee, Chia-Chung Hou, Pei-Wen Hsiao, Shih-Chang Chien, Lie-Fen Shyur, Ning-Sun Yang. Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. Journal of medicinal chemistry. 2007 Aug; 50(17):4087-95. doi: 10.1021/jm070295s. [PMID: 17663539]
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