Karanjin (BioDeep_00000266313)

 

Secondary id: BioDeep_00000017551, BioDeep_00000180248

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-Furo(2,3-h)-1-benzopyran-4-one, 3-methoxy-2-phenyl- (8CI)(9CI)

化学式: C18H12O4 (292.0735552)
中文名称: 水黄皮次素, 干华豆晶 4
谱图信息: 最多检出来源 Viridiplantae(plant) 0.39%

分子结构信息

SMILES: c(C(O4)=C(C(c(c43)ccc(c32)occ2)=O)OC)(c1)cccc1
InChI: InChI=1S/C18H12O4/c1-20-18-15(19)13-7-8-14-12(9-10-21-14)17(13)22-16(18)11-5-3-2-4-6-11/h2-10H,1H3

描述信息

relative retention time with respect to 9-anthracene Carboxylic Acid is 1.329
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.324
Karanjin is an orally active furanoflavonoid which can be isolated from several Leguminosae. Karanjin exhibits evident anti-diabetic, anti-cancer, anti-inflammatory, antioxidant, anticolitis, anti-ulcer, anti-Alzheimer properties and multiple insect repellent/insecticidal, acaricide properties, suggesting the potential of Karanjin to be applied to relevant research[1].
Karanjin is a major active furanoflavonol constituent of Fordia cauliflora. Karanjin induces GLUT4 translocation in skeletal muscle cells by increasing AMPK activity. Karanjin can induce cancer cell death through cell cycle arrest and enhance apoptosis[1][2].
Karanjin is a major active furanoflavonol constituent of Fordia cauliflora. Karanjin induces GLUT4 translocation in skeletal muscle cells by increasing AMPK activity. Karanjin can induce cancer cell death through cell cycle arrest and enhance apoptosis[1][2].

同义名列表

24 个代谢物同义名

4H-Furo(2,3-h)-1-benzopyran-4-one, 3-methoxy-2-phenyl- (8CI)(9CI); 4H-Furo[2,3-h]-1-benzopyran-4-one, 3-methoxy-2-phenyl-; 3-Methoxy-2-phenyl-4H-furo(2,3-h)(1)benzopyran-4-one; 3-methoxy-2-phenyl-pyrano[2,3-e][1]benzoxol-4-one; 3-methoxy-2-phenylpyrano[2,3-e][1]benzoxol-4-one; 3-methoxy-2-phenyl-pyrano[2,3-e]benzofuran-4-one; 3-methoxy-2-phenyl-4-pyrano[2,3-e]benzofuranone; 7-Methoxy-8-phenylfurano[2,3-h]chromen-6-one; FLAVONE (BOHLMAN); EINECS 208-319-9; NCGC00142418-01; NCGC00017182-01; MEGxp0_001687; ZINC00039119; AIDS-046608; AIDS046608; NSC 335755; NSC335755; ST055657; 521-88-0; Karanjin; TNP00046; 3-Methoxy-2-phenyl-4H-Furo [ 2,3-h ] -1-benzopyran-4-one; 3-Methoxy-2-phenyl-4H-furo[2,3-h]-1-benzopyran-4-one



数据库引用编号

35 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)

13 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

  • Gourav Kumar, Dev Mani Pandey, Manik Ghosh, Stefano Dall'Acqua, Rashmi Gupta, Nishi Prakash Tiwari, Usman Mohd Siddique, Leena Vishwakrama, Sunil Kant Guleri, Uma Ranjan Lal, Supriya Dubey. Karanjin, A Promising Bioactive Compound Possessing Anti-cancer Activity against Experimental Model of Non-small Cell Lung Cancer Cells. Anti-cancer agents in medicinal chemistry. 2024; 24(5):317-333. doi: 10.2174/0118715206255557231024095245. [PMID: 37936467]
  • Darpan Raghav, Susobhan Mahanty, Krishnan Rathinasamy. Biochemical and toxicological investigation of karanjin, a bio-pesticide isolated from Pongamia seed oil. Pesticide biochemistry and physiology. 2019 Jun; 157(?):108-121. doi: 10.1016/j.pestbp.2019.03.011. [PMID: 31153458]
  • Rituparna Roy, Debolina Pal, Subhayan Sur, Suvra Mandal, Prosenjit Saha, Chinmay Kumar Panda. Pongapin and Karanjin, furanoflavanoids of Pongamia pinnata, induce G2/M arrest and apoptosis in cervical cancer cells by differential reactive oxygen species modulation, DNA damage, and nuclear factor kappa-light-chain-enhancer of activated B cell signaling. Phytotherapy research : PTR. 2019 Apr; 33(4):1084-1094. doi: 10.1002/ptr.6302. [PMID: 30834631]
  • Rajni Sharma, Ibidapo S Williams, Linda Gatchie, Vinay R Sonawane, Bhabatosh Chaudhuri, Sandip B Bharate. Furanoflavones pongapin and lanceolatin B blocks the cell cycle and induce senescence in CYP1A1-overexpressing breast cancer cells. Bioorganic & medicinal chemistry. 2018 12; 26(23-24):6076-6086. doi: 10.1016/j.bmc.2018.11.013. [PMID: 30448188]
  • Ran Wen, Hai-Ning Lv, Yong Jiang, Peng-Fei Tu. Anti-inflammatory flavone and chalcone derivatives from the roots of Pongamia pinnata (L.) Pierre. Phytochemistry. 2018 May; 149(?):56-63. doi: 10.1016/j.phytochem.2018.02.005. [PMID: 29459216]
  • Jian-Ru Guo, Qian-Qian Chen, Christopher Wai-Kei Lam, Wei Zhang. Effects of karanjin on cell cycle arrest and apoptosis in human A549, HepG2 and HL-60 cancer cells. Biological research. 2015 Jul; 48(?):40. doi: 10.1186/s40659-015-0031-x. [PMID: 26209237]
  • Haribalan Perumalsamy, Myung Jin Jang, Jun-Ran Kim, Murugan Kadarkarai, Young-Joon Ahn. Larvicidal activity and possible mode of action of four flavonoids and two fatty acids identified in Millettia pinnata seed toward three mosquito species. Parasites & vectors. 2015 Apr; 8(?):237. doi: 10.1186/s13071-015-0848-8. [PMID: 25928224]
  • Deliang Yi, Zhihua Wang, Longzhi Yi. Development and validation of an LC-MS method for determination of Karanjin in rat plasma: application to preclinical pharmacokinetics. Journal of chromatographic science. 2015 Apr; 53(4):456-61. doi: 10.1093/chromsci/bmu064. [PMID: 25002684]
  • Wenli Wang, Jian Wang, Ning Li, Xiangrong Zhang, Weihong Zhao, Jiayuan Li, Yingying Si. Chemopreventive flavonoids from Millettia pulchra Kurz var-laxior (Dunn) Z.Wei (Yulangsan) function as Michael reaction acceptors. Bioorganic & medicinal chemistry letters. 2015 Mar; 25(5):1078-81. doi: 10.1016/j.bmcl.2015.01.009. [PMID: 25630222]
  • Jiayuan Li, Zhe Jiang, Xuezheng Li, Yue Hou, Fen Liu, Ning Li, Xia Liu, Lihua Yang. Natural therapeutic agents for neurodegenerative diseases from a traditional herbal medicine Pongamia pinnata (L.) Pierre. Bioorganic & medicinal chemistry letters. 2015 Jan; 25(1):53-8. doi: 10.1016/j.bmcl.2014.11.015. [PMID: 25466192]
  • Madhura Bose, Mousumi Chakraborty, Sourav Bhattacharya, Debarati Mukherjee, Suvra Mandal, Roshnara Mishra. Prevention of arthritis markers in experimental animal and inflammation signalling in macrophage by Karanjin isolated from Pongamia pinnata seed extract. Phytotherapy research : PTR. 2014 Aug; 28(8):1188-95. doi: 10.1002/ptr.5113. [PMID: 24399783]
  • Chung-Hung Chan, Gek-Cheng Ngoh, Rozita Yusoff. A brief review on anti diabetic plants: Global distribution, active ingredients, extraction techniques and acting mechanisms. Pharmacognosy reviews. 2012 Jan; 6(11):22-8. doi: 10.4103/0973-7847.95854. [PMID: 22654401]
  • Natasha Jaiswal, Prem P Yadav, Rakesh Maurya, Arvind K Srivastava, Akhilesh K Tamrakar. Karanjin from Pongamia pinnata induces GLUT4 translocation in skeletal muscle cells in a phosphatidylinositol-3-kinase-independent manner. European journal of pharmacology. 2011 Nov; 670(1):22-8. doi: 10.1016/j.ejphar.2011.08.049. [PMID: 21939653]
  • Sunita Shailajan, Sasikumar Menon, Suhas Pednekar, Ashish Singh. Wound healing efficacy of Jatyadi Taila: in vivo evaluation in rat using excision wound model. Journal of ethnopharmacology. 2011 Oct; 138(1):99-104. doi: 10.1016/j.jep.2011.08.050. [PMID: 21907784]
  • Vismaya, Srikanta M Belagihally, Sindhu Rajashekhar, Vinay B Jayaram, Shylaja M Dharmesh, Sindhu Kanya C Thirumakudalu. Gastroprotective Properties of Karanjin from Karanja (Pongamia pinnata) Seeds; Role as Antioxidant and H, K-ATPase Inhibitor. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):747246. doi: 10.1093/ecam/neq027. [PMID: 21799691]
  • Nina Kolesárová, Miroslav Hutňan, Igor Bodík, Viera Spalková. Utilization of biodiesel by-products for biogas production. Journal of biomedicine & biotechnology. 2011; 2011(?):126798. doi: 10.1155/2011/126798. [PMID: 21403868]
  • Anindita Ghosh, Suvra Mandal, Avijit Banerji, Julie Banerji. A new biflavonyloxymethane from Pongamia pinnata. Natural product communications. 2010 Aug; 5(8):1213-4. doi: ". [PMID: 20839621]
  • R Ranga Rao, Ashok K Tiwari, P Prabhakar Reddy, K Suresh Babu, Amtul Z Ali, K Madhusudana, J Madhusudana Rao. New furanoflavanoids, intestinal alpha-glucosidase inhibitory and free-radical (DPPH) scavenging, activity from antihyperglycemic root extract of Derris indica (Lam.). Bioorganic & medicinal chemistry. 2009 Jul; 17(14):5170-5. doi: 10.1016/j.bmc.2009.05.051. [PMID: 19515570]
  • Akhilesh K Tamrakar, Prem P Yadav, Priti Tiwari, Rakesh Maurya, Arvind K Srivastava. Identification of pongamol and karanjin as lead compounds with antihyperglycemic activity from Pongamia pinnata fruits. Journal of ethnopharmacology. 2008 Aug; 118(3):435-9. doi: 10.1016/j.jep.2008.05.008. [PMID: 18572336]
  • Zhi-Yuan Liang, Xiao-Sheng Yang, Hai-Yan Zhu, Xiao-Jiang Hao. [Two new flavones from Fordia cauliflora of Yunnan]. Yao xue xue bao = Acta pharmaceutica Sinica. 2006 Jun; 41(6):533-6. doi: ". [PMID: 16927828]
  • Sorwaporn Koysomboon, Ian van Altena, Shigeru Kato, Kan Chantrapromma. Antimycobacterial flavonoids from Derris indica. Phytochemistry. 2006 May; 67(10):1034-40. doi: 10.1016/j.phytochem.2006.03.019. [PMID: 16730034]
  • Hao Yin, Si Zhang, Jun Wu. [Study on flavonoids from stem bark of Pongamia pinnata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2004 Jul; 27(7):493-5. doi: ". [PMID: 15551964]
  • R S Zand, D J Jenkins, E P Diamandis. Steroid hormone activity of flavonoids and related compounds. Breast cancer research and treatment. 2000 Jul; 62(1):35-49. doi: 10.1023/a:1006422302173. [PMID: 10989984]