febrifugine (BioDeep_00000000490)

 

Secondary id: BioDeep_00000229911

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-[[(3aS,7aS)-2-hydroxy-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl]quinazolin-4-one

化学式: C16H19N3O3 (301.1426344)
中文名称: 常山乙素, (+)-异常山碱, 异常山碱, 异常山乙素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.01%

分子结构信息

SMILES: C1CC(C(NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O
InChI: InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2

描述信息

Isofebrifugine is a member of quinazolines.
Isofebrifugine is a natural product found in Hydrangea febrifuga and Hydrangea macrophylla with data available.
Febrifugine is a quinazolinone alkaloid found in the roots and leaves of Dichroa febrifuga, with antimalarial activity [1].
Febrifugine is a quinazolinone alkaloid found in the roots and leaves of Dichroa febrifuga, with antimalarial activity [1].

同义名列表

12 个代谢物同义名

beta-Dichroine; febrifugine; alpha-Dichroine; Dichroine-alpha; isofebrifugine; 3-(3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one; 3-[[(3aS,7aS)-2-hydroxy-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl]quinazolin-4-one; 3-[(3aS,7aS)-2-Hydroxyperhydrofuro[3,2-b]pyridin-2-ylmethyl]-3,4-dihydroquinazolin-4-one; 3-[(2-hydroxy-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridin-2-yl)methyl]quinazolin-4-one; 3-[(2-Hydroxyoctahydrofuro[3,2-b]pyridin-2-yl)methyl]quinazolin-4(3H)-one; Isofebrifugine; Febrifugine



数据库引用编号

36 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)

21 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

  • Jingyuan Chen, Shuhao Fan, Jianhua Guo, Jian Yang, Le Pan, Yong Xia. Discovery of anticancer function of Febrifugine: Inhibition of cell proliferation, induction of apoptosis and suppression steroid synthesis in bladder cancer cells. Toxicology and applied pharmacology. 2024 Mar; 484(?):116878. doi: 10.1016/j.taap.2024.116878. [PMID: 38431229]
  • Ping Ping Li, Lei Zhang, Jian Ping Wang. Research Note: Study on the residue depletion of febrifugine and isofebrifugine in broiler chicken. Poultry science. 2021 Oct; 100(10):101390. doi: 10.1016/j.psj.2021.101390. [PMID: 34391965]
  • Liu-Qing Sheng, Jia-Lei Ma. Preparative separation of two isomeric antimalaria alkaloids febrifugine and isofebrifugine from Dichroa febrifuga roots by countercurrent chromatography. Journal of separation science. 2021 May; 44(10):2153-2159. doi: 10.1002/jssc.202001257. [PMID: 33811736]
  • Ji-Yuan Zhang, Xiao-Rui Fan, Xiao-Qian Liu, Xiao-Wei Yu, Li-Xin Yang, Zhi-Ting Guo, Wei-Hong Feng, Zhi-Min Wang, Chun Li. [Quantitative determination of febrifugine by proton nuclear magnetic resonance spectroscopy with internal standard method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2018 Jan; 43(1):134-138. doi: 10.19540/j.cnki.cjcmm.20171027.005. [PMID: 29552823]
  • Ji-Yuan Zhang, Xiao-Qian Liu, Li-Xin Yang, Wei-Hong Feng, Zhi-Min Wang, Chun Li. [Investigation on stability and degradation kinetics of febrifugine]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Aug; 42(16):3178-3184. doi: 10.19540/j.cnki.cjcmm.2017.0126. [PMID: 29171238]
  • Ji-Yuan Zhang, Zi-Han Liu, Xiao-Qian Liu, Wei-Hong Feng, Li-Xin Yang, Zhi-Min Wang, Chun Li. [Simultaneous determination of febrifugine and isofebrifugine in Dichroa febrifuga root by HPLC method]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 May; 42(9):1711-1716. doi: 10.19540/j.cnki.cjcmm.20170224.017. [PMID: 29082694]
  • Jonathan D Herman, Lauren R Pepper, Joseph F Cortese, Guillermina Estiu, Kevin Galinsky, Vanessa Zuzarte-Luis, Emily R Derbyshire, Ulf Ribacke, Amanda K Lukens, Sofia A Santos, Vishal Patel, Clary B Clish, William J Sullivan, Huihao Zhou, Selina E Bopp, Paul Schimmel, Susan Lindquist, Jon Clardy, Maria M Mota, Tracy L Keller, Malcolm Whitman, Olaf Wiest, Dyann F Wirth, Ralph Mazitschek. The cytoplasmic prolyl-tRNA synthetase of the malaria parasite is a dual-stage target of febrifugine and its analogs. Science translational medicine. 2015 May; 7(288):288ra77. doi: 10.1126/scitranslmed.aaa3575. [PMID: 25995223]
  • Huihao Zhou, Litao Sun, Xiang-Lei Yang, Paul Schimmel. ATP-directed capture of bioactive herbal-based medicine on human tRNA synthetase. Nature. 2013 Feb; 494(7435):121-4. doi: 10.1038/nature11774. [PMID: 23263184]
  • Tracy L Keller, Davide Zocco, Mark S Sundrud, Margaret Hendrick, Maja Edenius, Jinah Yum, Yeon-Jin Kim, Hak-Kyo Lee, Joseph F Cortese, Dyann F Wirth, John David Dignam, Anjana Rao, Chang-Yeol Yeo, Ralph Mazitschek, Malcolm Whitman. Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase. Nature chemical biology. 2012 Feb; 8(3):311-7. doi: 10.1038/nchembio.790. [PMID: 22327401]
  • Timothy N C Wells. Natural products as starting points for future anti-malarial therapies: going back to our roots?. Malaria journal. 2011 Mar; 10 Suppl 1(?):S3. doi: 10.1186/1475-2875-10-s1-s3. [PMID: 21411014]
  • Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal. 2011 Mar; 10 Suppl 1(?):S4. doi: 10.1186/1475-2875-10-s1-s4. [PMID: 21411015]
  • Merlin Willcox, Françoise Benoit-Vical, Dennis Fowler, Geneviève Bourdy, Gemma Burford, Sergio Giani, Rocky Graziose, Peter Houghton, Milijaona Randrianarivelojosia, Philippe Rasoanaivo. Do ethnobotanical and laboratory data predict clinical safety and efficacy of anti-malarial plants?. Malaria journal. 2011 Mar; 10 Suppl 1(?):S7. doi: 10.1186/1475-2875-10-s1-s7. [PMID: 21411018]
  • Ying-Hua Yang, Rajesh Rajaiah, David Y-W Lee, Zhongze Ma, Hua Yu, Harry H S Fong, Lixing Lao, Brian M Berman, Kamal D Moudgil. Suppression of ongoing experimental arthritis by a chinese herbal formula (huo-luo-xiao-ling dan) involves changes in antigen-induced immunological and biochemical mediators of inflammation. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):642027. doi: 10.1155/2011/642027. [PMID: 20981317]
  • Andreia P Matos, Ana C Leite, Luciane G Batista-Pereira, Paulo C Vieira, Josäo B Fernandes, Maria Fátima das G F da Silva. Effects of limonoids from Cipadessa fruticosa on fall armyworm. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 May; 64(5-6):441-6. doi: 10.1515/znc-2009-5-623. [PMID: 19678552]
  • Akira Ishih, Toshi Nagata, Fumie Kobayashi, Francis W Muregi, Kaneo Ohori, Toshio Miyase. Possible involvement of IFN-gamma in early mortality of Plasmodium berghei NK65-infected BALB/c mice after febrifugine treatment. The Southeast Asian journal of tropical medicine and public health. 2008 Nov; 39(6):949-58. doi: . [PMID: 19062681]
  • Stanley Scheindlin. Antimalarials: shortages and searches. Molecular interventions. 2005 Oct; 5(5):268-72. doi: 10.1124/mi.5.5.2. [PMID: 16249521]
  • Suping Jiang, Qiang Zeng, Montip Gettayacamin, Anchalee Tungtaeng, Srisombat Wannaying, Apassorn Lim, Pranee Hansukjariya, Christopher O Okunji, Shuren Zhu, Daohe Fang. Antimalarial activities and therapeutic properties of febrifugine analogs. Antimicrobial agents and chemotherapy. 2005 Mar; 49(3):1169-76. doi: 10.1128/aac.49.3.1169-1176.2005. [PMID: 15728920]
  • A Ishih, T Nagata, F Kobayashi, T Miyase, M Terada. Cytokine and antibody production during the course of resolution in Plasmodium yoelii 17XL-infected BALB/c mice treated with febrifugine and isofebrifugine mixture from leaves of Hydrangea macrophylla var. Otaksa. Parasitology research. 2004 Oct; 94(3):176-82. doi: 10.1007/s00436-004-1187-4. [PMID: 15338283]
  • Akira Ishih, Toshio Miyase, Kaneo Ohori, Mamoru Terada. Different responses of three rodent Plasmodia species, Plasmodium yoelii 17XL, P. berghei NK65 and P. chabaudi AS on treatment with febrifugine and isofebrifugine mixture from Hydrangea macrophylla var. Otaksa leaf in ICR mice. Phytotherapy research : PTR. 2003 Jun; 17(6):650-6. doi: 10.1002/ptr.1219. [PMID: 12820234]
  • Akira Ishih, Toshio Miyase, Mamoru Terada. Comparison of antimalarial activity of the alkaloidal fraction of Hydrangea macrophylla var. Otaksa leaves with the hot-water extract in ICR mice infected with Plasmodium yoelii 17 XL. Phytotherapy research : PTR. 2003 Jun; 17(6):633-9. doi: 10.1002/ptr.1215. [PMID: 12820231]
  • Haruhisa Kikuchi, Hidehisa Tasaka, Shingo Hirai, Yoshiaki Takaya, Yoshiharu Iwabuchi, Hidenori Ooi, Susumi Hatakeyama, Hye-Sook Kim, Yusuke Wataya, Yoshiteru Oshima. Potent antimalarial febrifugine analogues against the plasmodium malaria parasite. Journal of medicinal chemistry. 2002 Jun; 45(12):2563-70. doi: 10.1021/jm010448q. [PMID: 12036365]
  • R Patnam, F R Chang, C Y Chen, R Y Kuo, Y H Lee, Y C Wu. Hydrachine A, a novel alkaloid from the roots of Hydrangea chinensis. Journal of natural products. 2001 Jul; 64(7):948-9. doi: 10.1021/np010091t. [PMID: 11473431]
  • K Murata, F Takano, S Fushiya, Y Oshima. Potentiation by febrifugine of host defense in mice against Plasmodium berghei NK65. Biochemical pharmacology. 1999 Nov; 58(10):1593-601. doi: 10.1016/s0006-2952(99)00244-0. [PMID: 10535750]
  • K Murata, F Takano, S Fushiya, Y Oshima. Enhancement of NO production in activated macrophages in vivo by an antimalarial crude drug, Dichroa febrifuga. Journal of natural products. 1998 Jun; 61(6):729-33. doi: 10.1021/np970433o. [PMID: 9644055]
  • J Watkins, A Padfield, J D Alderson. Underlying immunopathology as a cause of adverse responses to two intravenous anaesthetic agents. British medical journal. 1978 May; 1(6121):1180-1. doi: 10.1136/bmj.1.6121.1180. [PMID: 638678]