Bergamottin (BioDeep_00000000330)

 

Secondary id: BioDeep_00000018692, BioDeep_00000398566, BioDeep_00000861004

PANOMIX_OTCML-2023


代谢物信息卡片


7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-

化学式: C21H22O4 (338.1518012)
中文名称: 佛手柑素
谱图信息: 最多检出来源 Macaca mulatta(otcml) 4.68%

分子结构信息

SMILES: CC(=CCC/C(=C/COc1c2ccc(=O)oc2cc2c1cco2)/C)C
InChI: InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+

描述信息

Bergomottin is a furanocoumarin. It has a role as a metabolite.
Bergamottin is a natural product found in Hansenia forbesii, Citrus hystrix, and other organisms with data available.
See also: Lime (Citrus) (part of).
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
A natural product found in Citrus hystrix.
Bergamottin is a potent and competitive CYP1A1 inhibitor with a Ki of 10.703 nM.
Bergamottin is a potent and competitive CYP1A1 inhibitor with a Ki of 10.703 nM.

同义名列表

22 个代谢物同义名

7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-; 7H-furo(3,2-g)(1)benzopyran-7-one, 4-(((2E)-3,7-dimethyl-2,6-octadien-1-yl)oxy)-; 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-; 4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g][1]benzopyran-7-one; 4-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one; 4-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-7H-furo(3,2-g)chromen-7-one; 4-([(2E)-3,7-dimethyl-2,6-octadienyl]oxy)-7h-furo[3,2-g]chromen-7-one; (E)-4-(3,7-dimethylocta-2,6-dienyloxy)-7H-furo[3,2-g]chromen-7-one; 4-[(2Z)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one; 4-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one; 5-Geranoxypsoralen;Bergamotine;Bergaptin; Bergamottin, analytical standard; Bergaptol geranyl ether; 5-Geranyloxypsoralen; 8-Geranyloxypsoralen; 5-geranoxypsoralen; BERGAMOTTIN [MI]; Bergamotine; bergamottin; Bergomottin; Bergamotin; Bergaptin



数据库引用编号

15 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)

12 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

  • José Villalaín. Bergamottin: location, aggregation and interaction with the plasma membrane. Journal of biomolecular structure & dynamics. 2023; 41(21):12026-12037. doi: 10.1080/07391102.2022.2164521. [PMID: 36602143]
  • Minmin Zhou, Yang Liu, Junyuan Cao, Siqi Dong, Yuxia Hou, Yan Yu, Qiuyan Zhang, Yueli Zhang, Xiaoying Jia, Bo Zhang, Gengfu Xiao, Gang Li, Wei Wang. Bergamottin, a bioactive component of bergamot, inhibits SARS-CoV-2 infection in golden Syrian hamsters. Antiviral research. 2022 08; 204(?):105365. doi: 10.1016/j.antiviral.2022.105365. [PMID: 35732228]
  • Xinjuan Zhang, Jinyao Guo, Jin Li, Chen Chen, Guijun Su. Pharmacokinetics and pharmacodynamic interaction of bergamottin with atorvastatin in rats. Xenobiotica; the fate of foreign compounds in biological systems. 2022 Jun; ?(?):1-5. doi: 10.1080/00498254.2022.2090301. [PMID: 35699169]
  • Ryosuke Munakata, Alexandre Olry, Tomoya Takemura, Kanade Tatsumi, Takuji Ichino, Cloé Villard, Joji Kageyama, Tetsuya Kurata, Masaru Nakayasu, Florence Jacob, Takao Koeduka, Hirobumi Yamamoto, Eiko Moriyoshi, Tetsuya Matsukawa, Jérémy Grosjean, Célia Krieger, Akifumi Sugiyama, Masaharu Mizutani, Frédéric Bourgaud, Alain Hehn, Kazufumi Yazaki. Parallel evolution of UbiA superfamily proteins into aromatic O-prenyltransferases in plants. Proceedings of the National Academy of Sciences of the United States of America. 2021 04; 118(17):. doi: 10.1073/pnas.2022294118. [PMID: 33883279]
  • Alessandro Maugeri, Giovanni Enrico Lombardo, Laura Musumeci, Caterina Russo, Sebastiano Gangemi, Gioacchino Calapai, Santa Cirmi, Michele Navarra. Bergamottin and 5-Geranyloxy-7-methoxycoumarin Cooperate in the Cytotoxic Effect of Citrus bergamia (Bergamot) Essential Oil in Human Neuroblastoma SH-SY5Y Cell Line. Toxins. 2021 04; 13(4):. doi: 10.3390/toxins13040275. [PMID: 33920139]
  • Jianwei Chen, Yaojia Lu, Xinyi Ye, Mahmoud Emam, Huawei Zhang, Hong Wang. Current advances in Vibrio harveyi quorum sensing as drug discovery targets. European journal of medicinal chemistry. 2020 Dec; 207(?):112741. doi: 10.1016/j.ejmech.2020.112741. [PMID: 32871343]
  • Miriam Rossi, Sandjida Aktar, Marissa Davis, Emily Hefter Feuss, Samara Roman-Holba, Kelly Wen, Christopher Gahn, Francesco Caruso. The Grapefruit Effect: Interaction between Cytochrome P450 and Coumarin Food Components, Bergamottin, Fraxidin and Osthole. X-ray Crystal Structure and DFT Studies. Molecules (Basel, Switzerland). 2020 Jul; 25(14):. doi: 10.3390/molecules25143158. [PMID: 32664320]
  • Jeong-Hyeon Ko, Frank Arfuso, Gautam Sethi, Kwang Seok Ahn. Pharmacological Utilization of Bergamottin, Derived from Grapefruits, in Cancer Prevention and Therapy. International journal of molecular sciences. 2018 Dec; 19(12):. doi: 10.3390/ijms19124048. [PMID: 30558157]
  • Jeong-Hyeon Ko, Dongwoo Nam, Jae-Young Um, Sang Hoon Jung, Kwang Seok Ahn. Bergamottin Inhibits Adipogenesis in 3T3-L1 Cells and Weight Regulation in Diet-Induced Obese Mice. The American journal of Chinese medicine. 2018; 46(3):601-615. doi: 10.1142/s0192415x18500313. [PMID: 29614883]
  • Yilong Liu, Chuanhong Ren, Yunlin Cao, Yue Wang, Wenyi Duan, Linfeng Xie, Chongde Sun, Xian Li. Characterization and Purification of Bergamottin from Citrus grandis (L.) Osbeck cv. Yongjiazaoxiangyou and Its Antiproliferative Activity and Effect on Glucose Consumption in HepG2 cells. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071227. [PMID: 28726768]
  • Emily J Johnson, Christina S Won, Kathleen Köck, Mary F Paine. Prioritizing pharmacokinetic drug interaction precipitants in natural products: application to OATP inhibitors in grapefruit juice. Biopharmaceutics & drug disposition. 2017 Apr; 38(3):251-259. doi: 10.1002/bdd.2061. [PMID: 28032362]
  • Juan Xu, Lili Ma, Dong Jiang, Shiping Zhu, Fuhua Yan, Yunxia Xie, Zongzhou Xie, Wenwu Guo, Xiuxin Deng. Content evaluation of 4 furanocoumarin monomers in various citrus germplasms. Food chemistry. 2015 Nov; 187(?):75-81. doi: 10.1016/j.foodchem.2015.04.007. [PMID: 25977000]
  • Michele Navarra, Nadia Ferlazzo, Santa Cirmi, Elena Trapasso, Placido Bramanti, Giovanni Enrico Lombardo, Paola Lucia Minciullo, Gioacchino Calapai, Sebastiano Gangemi. Effects of bergamot essential oil and its extractive fractions on SH-SY5Y human neuroblastoma cell growth. The Journal of pharmacy and pharmacology. 2015 Aug; 67(8):1042-53. doi: 10.1111/jphp.12403. [PMID: 25808679]
  • Tatsuya Kawasaki, Hideyuki Ito, Hiroshi Omote. Components of foods inhibit a drug exporter, human multidrug and toxin extrusion transporter 1. Biological & pharmaceutical bulletin. 2014; 37(2):292-7. doi: 10.1248/bpb.b13-00815. [PMID: 24492725]
  • Kyung Myung, John A Manthey, Jan A Narciso. Protein sequestration of lipophilic furanocoumarins in grapefruit juice. Journal of agricultural and food chemistry. 2013 Jan; 61(3):667-73. doi: 10.1021/jf304271s. [PMID: 23256844]
  • Marie Bräunlich, Hege Christensen, Siri Johannesen, Rune Slimestad, Helle Wangensteen, Karl E Malterud, Hilde Barsett. In vitro inhibition of cytochrome P450 3A4 by Aronia melanocarpa constituents. Planta medica. 2013 Jan; 79(2):137-41. doi: 10.1055/s-0032-1328055. [PMID: 23250807]
  • Nallely E Sandoval-Montemayor, Abraham García, Elizabeth Elizondo-Treviño, Elvira Garza-González, Laura Alvarez, María del Rayo Camacho-Corona. Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents. Molecules (Basel, Switzerland). 2012 Sep; 17(9):11173-84. doi: 10.3390/molecules170911173. [PMID: 22992784]
  • Ram M Uckoo, Guddadarangavvanahally K Jayaprakasha, V M Balasubramaniam, Bhimanagouda S Patil. Grapefruit (Citrus paradisi Macfad) phytochemicals composition is modulated by household processing techniques. Journal of food science. 2012 Sep; 77(9):C921-6. doi: 10.1111/j.1750-3841.2012.02865.x. [PMID: 22957912]
  • Anastasia Messer, Anna Nieborowski, Christian Strasser, Christiane Lohr, Dieter Schrenk. Major furocoumarins in grapefruit juice I: levels and urinary metabolite(s). Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Dec; 49(12):3224-31. doi: 10.1016/j.fct.2011.09.005. [PMID: 21945416]
  • Thaïs B César, John A Manthey, Kyung Myung. Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4. Journal of natural products. 2009 Sep; 72(9):1702-4. doi: 10.1021/np900266m. [PMID: 19689106]
  • Y Uesawa, H Yamada, K Mohri. Determination of bergamottin in human plasma after grapefruit juice ingestion by an UPLC/MS/MS method. Die Pharmazie. 2008 Feb; 63(2):110-2. doi: NULL. [PMID: 18380396]
  • Yoshihiro Uesawa, Kiminori Mohri. The use of heat treatment to eliminate drug interactions due to grapefruit juice. Biological & pharmaceutical bulletin. 2006 Nov; 29(11):2274-8. doi: 10.1248/bpb.29.2274. [PMID: 17077528]
  • Hiroki Satoh, Fumiaki Yamashita, Masayuki Tsujimoto, Hideyasu Murakami, Noriko Koyabu, Hisakazu Ohtani, Yasufumi Sawada. Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug metabolism and disposition: the biological fate of chemicals. 2005 Apr; 33(4):518-23. doi: 10.1124/dmd.104.002337. [PMID: 15640378]
  • Annette Baumgart, Melanie Schmidt, Hans-Joachim Schmitz, Dieter Schrenk. Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Biochemical pharmacology. 2005 Feb; 69(4):657-67. doi: 10.1016/j.bcp.2004.11.017. [PMID: 15670584]
  • Yoko Honda, Fumihiko Ushigome, Noriko Koyabu, Satoshi Morimoto, Yukihiro Shoyama, Takeshi Uchiumi, Michihiko Kuwano, Hisakazu Ohtani, Yasufumi Sawada. Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux. British journal of pharmacology. 2004 Dec; 143(7):856-64. doi: 10.1038/sj.bjp.0706008. [PMID: 15504753]
  • Theunis C Goosen, Doré Cillié, David G Bailey, Chongwoo Yu, Kan He, Paul F Hollenberg, Patrick M Woster, Lucinda Cohen, J Andrew Williams, Malie Rheeders, H Paul Dijkstra. Bergamottin contribution to the grapefruit juice-felodipine interaction and disposition in humans. Clinical pharmacology and therapeutics. 2004 Dec; 76(6):607-17. doi: 10.1016/j.clpt.2004.08.019. [PMID: 15592332]
  • David J Greenblatt, Lisa L von Moltke, Jerold S Harmatz, Gengsheng Chen, James L Weemhoff, Cheng Jen, Charles J Kelley, Barbara W LeDuc, Miguel A Zinny. Time course of recovery of cytochrome p450 3A function after single doses of grapefruit juice. Clinical pharmacology and therapeutics. 2003 Aug; 74(2):121-9. doi: 10.1016/s0009-9236(03)00118-8. [PMID: 12891222]
  • David G Bailey, George K Dresser, John R Bend. Bergamottin, lime juice, and red wine as inhibitors of cytochrome P450 3A4 activity: comparison with grapefruit juice. Clinical pharmacology and therapeutics. 2003 Jun; 73(6):529-37. doi: 10.1016/s0009-9236(03)00051-1. [PMID: 12811362]
  • Heather E Kleiner, Suryanarayana V Vulimiri, Melissa J Reed, Ann Uberecken, John DiGiovanni. Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation. Chemical research in toxicology. 2002 Feb; 15(2):226-35. doi: 10.1021/tx010151v. [PMID: 11849049]
  • Jasminder Sahi, Eric L Reyner, Jonathan N Bauman, Kristina Gueneva-Boucheva, James E Burleigh, V Hayden Thomas. The effect of bergamottin on diazepam plasma levels and P450 enzymes in beagle dogs. Drug metabolism and disposition: the biological fate of chemicals. 2002 Feb; 30(2):135-40. doi: 10.1124/dmd.30.2.135. [PMID: 11792681]
  • George K Dresser, David G Bailey, Brenda F Leake, Ute I Schwarz, Paul A Dawson, David J Freeman, Richard B Kim. Fruit juices inhibit organic anion transporting polypeptide-mediated drug uptake to decrease the oral availability of fexofenadine. Clinical pharmacology and therapeutics. 2002 Jan; 71(1):11-20. doi: 10.1067/mcp.2002.121152. [PMID: 11823753]
  • K Mohri, Y Uesawa. Effects of furanocoumarin derivatives in grapefruit juice on nifedipine pharmacokinetics in rats. Pharmaceutical research. 2001 Feb; 18(2):177-82. doi: 10.1023/a:1011028401189. [PMID: 11405288]
  • S Malhotra, D G Bailey, M F Paine, P B Watkins. Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins. Clinical pharmacology and therapeutics. 2001 Jan; 69(1):14-23. doi: 10.1067/mcp.2001.113185. [PMID: 11180034]
  • T Ikegawa, F Ushigome, N Koyabu, S Morimoto, Y Shoyama, M Naito, T Tsuruo, H Ohtani, Y Sawada. Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer letters. 2000 Nov; 160(1):21-8. doi: 10.1016/s0304-3835(00)00549-8. [PMID: 11098080]
  • A Ohnishi, H Matsuo, S Yamada, H Takanaga, S Morimoto, Y Shoyama, H Ohtani, Y Sawada. Effect of furanocoumarin derivatives in grapefruit juice on the uptake of vinblastine by Caco-2 cells and on the activity of cytochrome P450 3A4. British journal of pharmacology. 2000 Jul; 130(6):1369-77. doi: 10.1038/sj.bjp.0703433. [PMID: 10903978]
  • V A Eagling, L Profit, D J Back. Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. British journal of clinical pharmacology. 1999 Oct; 48(4):543-52. doi: 10.1046/j.1365-2125.1999.00052.x. [PMID: 10583025]
  • Y Q Xiao, Y F Sun, X H Liu. [Chemical constituents of Notopterygium incisum Ting]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1994 Jul; 19(7):421-2, 447. doi: ". [PMID: 7802950]
  • P Morlière, G Hüppe, D Averbeck, A R Young, R Santus, L Dubertret. In vitro photostability and photosensitizing properties of bergamot oil. Effects of a cinnamate sunscreen. Journal of photochemistry and photobiology. B, Biology. 1990 Nov; 7(2-4):199-208. doi: 10.1016/1011-1344(90)85157-r. [PMID: 2128324]