Bergamottin (BioDeep_00000018692)

Main id: BioDeep_00000000330

 

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


4-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ci

化学式: C21H22O4 (338.1518012)
中文名称: 佛手柑素
谱图信息: 最多检出来源 () 0%

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

Bergamottin is found in citrus. Bergamottin is a constituent of bergamot oil. Also from lemon oil and oils of other Citrus species and carrot (Daucus carota) Bergamottin is a natural furanocoumarin found principally in grapefruit juice. It is also found in the oil of bergamot, from which it was first isolated and from which its name is derived. To a lesser extent, bergamottin is also present in the essential oils of other citrus fruits. Along with the chemically related compound 6 ,7 -dihydroxybergamottin, it is believed to be responsible for the grapefruit juice effect in which the consumption of the juice affects the metabolism of a variety of pharmaceutical drugs
Constituent of bergamot oiland is also from lemon oil and oils of other Citrus subspecies and carrot (Daucus carota)
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

11 个代谢物同义名

4-[(3,7-Dimethyl-2,6-octadienyl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one, 9ci; 4-{[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one; 4-{[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]oxy}furo[3,2-g]chromen-7-one; Bergaptol geranyl ether; 5-Geranyloxypsoralen; 5-geranoxypsoralen; Bergamotine; bergamottin; Bergamotin; Bergaptin; BCP31566



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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WikiPathways(0)

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INOH(0)

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69 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

  • Priyanka Chaudhary, G K Jayaprakasha, Ron Porat, Bhimanagouda S Patil. Degreening and postharvest storage influences 'Star Ruby' grapefruit (Citrus paradisi Macf.) bioactive compounds. Food chemistry. 2012 Dec; 135(3):1667-75. doi: 10.1016/j.foodchem.2012.05.095. [PMID: 22953908]
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  • Pius S Fasinu, Patrick J Bouic, Bernd Rosenkranz. An overview of the evidence and mechanisms of herb-drug interactions. Frontiers in pharmacology. 2012; 3(?):69. doi: 10.3389/fphar.2012.00069. [PMID: 22557968]
  • 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]
  • Helge Joa, Sylvia Vogl, Atanas G Atanasov, Martin Zehl, Thomas Nakel, Nanang Fakhrudin, Elke H Heiss, Paolo Picker, Ernst Urban, Christoph Wawrosch, Johannes Saukel, Gottfried Reznicek, Brigitte Kopp, Verena M Dirsch. Identification of ostruthin from Peucedanum ostruthium rhizomes as an inhibitor of vascular smooth muscle cell proliferation. Journal of natural products. 2011 Jun; 74(6):1513-6. doi: 10.1021/np200072a. [PMID: 21627108]
  • Monica Borgatti, Irene Mancini, Nicoletta Bianchi, Alessandra Guerrini, Ilaria Lampronti, Damiano Rossi, Gianni Sacchetti, Roberto Gambari. Bergamot (Citrus bergamia Risso) fruit extracts and identified components alter expression of interleukin 8 gene in cystic fibrosis bronchial epithelial cell lines. BMC biochemistry. 2011 Apr; 12(?):15. doi: 10.1186/1471-2091-12-15. [PMID: 21496221]
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  • Maryam Modarai, Andy Suter, Andreas Kortenkamp, Michael Heinrich. The interaction potential of herbal medicinal products: a luminescence-based screening platform assessing effects on cytochrome P450 and its use with devil's claw (Harpagophyti radix) preparations. The Journal of pharmacy and pharmacology. 2011 Mar; 63(3):429-38. doi: 10.1111/j.2042-7158.2010.01235.x. [PMID: 21749392]
  • Christiane Lohr, Nicole Raquet, Dieter Schrenk. Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells. Toxicology in vitro : an international journal published in association with BIBRA. 2010 Mar; 24(2):558-66. doi: 10.1016/j.tiv.2009.10.017. [PMID: 19883747]
  • 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]
  • Katja Strauch, Ursula Lutz, Nataly Bittner, Werner K Lutz. Dose-response relationship for the pharmacokinetic interaction of grapefruit juice with dextromethorphan investigated by human urinary metabolite profiles. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Aug; 47(8):1928-35. doi: 10.1016/j.fct.2009.05.004. [PMID: 19445995]
  • Ying-Ku Lin, Ming-Thau Sheu, Chia-Hui Huang, Hsiu-O Ho. Development of a reversed-phase high-performance liquid chromatographic method for analyzing furanocoumarin components in citrus fruit juices and Chinese herbal medicines. Journal of chromatographic science. 2009 Mar; 47(3):211-5. doi: 10.1093/chromsci/47.3.211. [PMID: 19298708]
  • Peng Zhang, Xiu-Wei Yang. [Studies on chemical constituents in roots and rhizomes of Notopterygium incisum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Dec; 33(24):2918-21. doi: . [PMID: 19294850]
  • Claudio Gardana, Federico Nalin, Paolo Simonetti. Evaluation of flavonoids and furanocoumarins from Citrus bergamia (Bergamot) juice and identification of new compounds. Molecules (Basel, Switzerland). 2008 Sep; 13(9):2220-8. doi: 10.3390/molecules13092220. [PMID: 18830151]
  • Tadashi Fujita, Atsushi Kawase, Toshiro Niwa, Norimichi Tomohiro, Megumi Masuda, Hideaki Matsuda, Masahiro Iwaki. Comparative evaluation of 12 immature citrus fruit extracts for the inhibition of cytochrome P450 isoform activities. Biological & pharmaceutical bulletin. 2008 May; 31(5):925-30. doi: 10.1248/bpb.31.925. [PMID: 18451520]
  • 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]
  • Subroto Acharjee, Francine K Welty. Atorvastatin and cardiovascular risk in the elderly--patient considerations. Clinical interventions in aging. 2008; 3(2):299-314. doi: 10.2147/cia.s2442. [PMID: 18686752]
  • Jawad Kiani, Sardar Z Imam. Medicinal importance of grapefruit juice and its interaction with various drugs. Nutrition journal. 2007 Oct; 6(?):33. doi: 10.1186/1475-2891-6-33. [PMID: 17971226]
  • 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]
  • Yoshihiro Uesawa, Kiminori Mohri. UV-irradiated grapefruit juice loses pharmacokinetic interaction with nifedipine in rats. Biological & pharmaceutical bulletin. 2006 Jun; 29(6):1286-9. doi: 10.1248/bpb.29.1286. [PMID: 16755036]
  • 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]
  • Tetsuya Saita, Hiroshi Fujito, Masato Mori. Screening of furanocoumarin derivatives in citrus fruits by enzyme-linked immunosorbent assay. Biological & pharmaceutical bulletin. 2004 Jul; 27(7):974-7. doi: 10.1248/bpb.27.974. [PMID: 15256725]
  • Shufeng Zhou, Lee Yong Lim, Balram Chowbay. Herbal modulation of P-glycoprotein. Drug metabolism reviews. 2004 Feb; 36(1):57-104. doi: 10.1081/dmr-120028427. [PMID: 15072439]
  • Shufeng Zhou, Hwee-Ling Koh, Yihuai Gao, Zhi-yuan Gong, Edmund Jon Deoon Lee. Herbal bioactivation: the good, the bad and the ugly. Life sciences. 2004 Jan; 74(8):935-68. doi: 10.1016/j.lfs.2003.09.035. [PMID: 14672753]
  • 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]
  • 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]
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