Bergaptol (BioDeep_00000000346)

 

Secondary id: BioDeep_00000864309

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy- (8CI)(9CI)

化学式: C11H6O4 (202.0266)
中文名称: 香柑醇, 佛手酚
谱图信息: 最多检出来源 Homo sapiens(blood) 25.95%

分子结构信息

SMILES: c12c(ccc(=O)o1)c(c1c(c2)occ1)O
InChI: InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H

描述信息

Bergaptol is a member of psoralens and a 5-hydroxyfurocoumarin. It is a conjugate acid of a bergaptol(1-).
Bergaptol is a natural product found in Citrus canaliculata, Hansenia forbesii, and other organisms with data available.
Bergaptol is a secondary metabolite of psoralen which has been hydroxylated by liver enzymes during phase I metabolism. Bergaptol is a biomarker for the consumption of citrus fruits.
Present in various citrus subspecies Bergaptol is found in many foods, some of which are common hazelnut, hazelnut, alaska blueberry, and groundcherry.
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
Bergaptol is an inhibitor of debenzylation of the CYP3A4 enzyme with an IC50 of 24.92 uM. Recent studies have shown that it has anti-proliferative and anti-cancer properties.
Bergaptol is an inhibitor of debenzylation of the CYP3A4 enzyme with an IC50 of 24.92 uM. Recent studies have shown that it has anti-proliferative and anti-cancer properties.

同义名列表

32 个代谢物同义名

7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy- (8CI)(9CI); 4-Hydroxy-7H-furo[3,2-g]chromen-7-one (ACD/Name 4.0); {7H-Furo[3,} {2-g][1]benzopyran-7-one,} 4-hydroxy-; 7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy-; 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy-; 4-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one; 4-Hydroxy7H-furo[3,2-g][1]benzopyran-7-one; 4-Hydroxy-7H-furo[3,2-g]chromen-7-one #; 4-Hydroxy-7H-furo(3,2-g)chromen-7-one; 4-Hydroxybergapten; 5-Hydroxypsoralen; 5-hydroxy-2H-furo[3,2-g]chromen-2-one; 4-Hydroxy-7H-furo[3,2-g]chromen-7-one; 5-Hydroxypsoralen;4-Hydroxybergapten; 4-oxidanylfuro[3,2-g]chromen-7-one; 4-hydroxyfuro[3,2-g]chromen-7-one; Bergaptol, analytical standard; 5-Hydroxy-6,7-furanocoumarin; 5-Hydroxyfuranocoumarin; 5-Hydroxyfurocoumarin; 7H-Furo[3, 4-hydroxy-; Psoralin, 5-hydroxy-; 5-HYDROXY-PSORALIN; 5-Hydroxy-Psoralen; 4-Hydroxybergapten; 5-Hydroxypsoralen; 4-Hydroxypsoralen; UNII-KTC8ANI30F; KTC8ANI30F; Bergaptols; Bergaptol; 8B6; Bergaptol



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

106 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • linear furanocoumarin biosynthesis: (+)-marmesin + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ H2O + acetone + an oxidized [NADPH-hemoprotein reductase] + psoralen

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(102)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

60 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。

亚细胞结构定位 关联基因列表
Cytoplasm 14 CA1, CD36, CYP3A4, JAK2, MAPK1, MAPK14, MAPK8, MITF, NR0B1, PRPF19, PTGS2, SRA1, STAT3, TYR
Peripheral membrane protein 3 GORASP1, JAK2, PTGS2
Endoplasmic reticulum membrane 3 CYP3A4, HMOX1, PTGS2
Nucleus 10 HMOX1, JAK2, MAPK1, MAPK14, MAPK8, MITF, NR0B1, PRPF19, SRA1, STAT3
cytosol 10 CA1, HMOX1, IL1B, JAK2, MAPK1, MAPK14, MAPK8, MITF, SRA1, STAT3
phagocytic vesicle 1 CD36
centrosome 1 MAPK1
nucleoplasm 10 HMOX1, JAK2, MAPK1, MAPK14, MAPK8, MITF, NR0B1, PRPF19, SRA1, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 2 CD36, TNF
Cytoplasmic side 2 GORASP1, HMOX1
Multi-pass membrane protein 1 CD36
Golgi apparatus membrane 1 GORASP1
Synapse 2 MAPK1, MAPK8
cell surface 2 CD36, TNF
glutamatergic synapse 2 JAK2, MAPK14
Golgi apparatus 3 CD36, GORASP1, MAPK1
Golgi membrane 1 GORASP1
lysosomal membrane 1 MITF
neuronal cell body 1 TNF
postsynapse 1 JAK2
Cytoplasm, cytosol 1 IL1B
Lysosome 2 IL1B, TYR
plasma membrane 6 CD36, JAK2, MAPK1, SRA1, STAT3, TNF
Membrane 6 CD36, CYP3A4, HMOX1, JAK2, NR0B1, PRPF19
apical plasma membrane 1 CD36
axon 1 MAPK8
caveola 4 CD36, JAK2, MAPK1, PTGS2
extracellular exosome 1 CA1
Lysosome membrane 1 MITF
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 5 CD36, HMOX1, IL1B, IL6, TNF
perinuclear region of cytoplasm 2 HMOX1, TYR
mitochondrion 2 MAPK1, MAPK14
protein-containing complex 2 MITF, PTGS2
intracellular membrane-bounded organelle 3 CYP3A4, NR0B1, TYR
Microsome membrane 2 CYP3A4, PTGS2
Single-pass type I membrane protein 1 TYR
Secreted 2 IL1B, IL6
extracellular region 6 DNAH9, IL1B, IL6, MAPK1, MAPK14, TNF
cytoplasmic side of plasma membrane 1 JAK2
mitochondrial outer membrane 1 HMOX1
transcription regulator complex 1 STAT3
centriolar satellite 1 NR0B1
motile cilium 1 DNAH9
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
external side of plasma membrane 2 CD36, TNF
microtubule cytoskeleton 1 SRA1
Melanosome membrane 1 TYR
Early endosome 1 MAPK1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 CD36
Membrane raft 3 CD36, JAK2, TNF
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton, spindle 2 MAPK1, PRPF19
focal adhesion 2 JAK2, MAPK1
microtubule 1 DNAH9
spindle 2 MAPK1, PRPF19
cis-Golgi network 1 GORASP1
collagen trimer 1 CD36
secretory granule 1 IL1B
axoneme 1 DNAH9
nuclear speck 3 MAPK14, NR0B1, PRPF19
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK1
receptor complex 1 CD36
neuron projection 1 PTGS2
chromatin 3 MITF, NR0B1, STAT3
phagocytic cup 1 TNF
cell periphery 1 CD36
mitotic spindle 1 MAPK1
cytoskeleton 2 JAK2, MAPK1
brush border membrane 1 CD36
spindle pole 1 MAPK14
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
spliceosomal complex 1 PRPF19
site of double-strand break 1 PRPF19
intercellular bridge 1 SRA1
Endomembrane system 1 JAK2
endosome lumen 1 JAK2
Lipid droplet 1 PRPF19
Membrane, caveola 1 MAPK1
Nucleus, nucleoplasm 1 PRPF19
specific granule membrane 1 CD36
Melanosome 1 TYR
euchromatin 1 JAK2
pseudopodium 1 MAPK1
ficolin-1-rich granule lumen 2 MAPK1, MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 3 IL6, MAPK1, PTGS2
endocytic vesicle membrane 1 CD36
Secreted, extracellular exosome 1 IL1B
azurophil granule lumen 1 MAPK1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
extrinsic component of cytoplasmic side of plasma membrane 1 JAK2
U2-type catalytic step 1 spliceosome 1 PRPF19
basal dendrite 1 MAPK8
catalytic step 2 spliceosome 1 PRPF19
Prp19 complex 1 PRPF19
U2-type catalytic step 2 spliceosome 1 PRPF19
extrinsic component of plasma membrane 1 JAK2
granulocyte macrophage colony-stimulating factor receptor complex 1 JAK2
interleukin-12 receptor complex 1 JAK2
interleukin-23 receptor complex 1 JAK2
platelet alpha granule membrane 1 CD36
ribosome 1 NR0B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
outer dynein arm 1 DNAH9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
distal portion of axoneme 1 DNAH9


文献列表

  • Chun-Yan Shen, Tian-Xing Wang, Jian-Guo Jiang, Chun-Ling Huang, Wei Zhu. Bergaptol from blossoms of Citrus aurantium L. var. amara Engl inhibits LPS-induced inflammatory responses and ox-LDL-induced lipid deposition. Food & function. 2020 Jun; 11(6):4915-4926. doi: 10.1039/c9fo00255c. [PMID: 32432251]
  • Takuhiro Uto, Nguyen Huu Tung, Risa Taniyama, Tosihide Miyanowaki, Osamu Morinaga, Yukihiro Shoyama. Anti-inflammatory Activity of Constituents Isolated from Aerial Part of Angelica acutiloba Kitagawa. Phytotherapy research : PTR. 2015 Dec; 29(12):1956-63. doi: 10.1002/ptr.5490. [PMID: 26463105]
  • Stavros E Bariamis, Marilena Marin, Constantinos M Athanassopoulos, Christos Kontogiorgis, Zinovia Tsimali, Dionissios Papaioannou, Giovanni Sindona, Giovanni Romeo, Konstantinos Avgoustakis, Dimitra Hadjipavlou-Litina. Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives. European journal of medicinal chemistry. 2013 Feb; 60(?):155-69. doi: 10.1016/j.ejmech.2012.11.043. [PMID: 23291118]
  • Ryosuke Munakata, Tsuyoshi Inoue, Takao Koeduka, Kanako Sasaki, Yusuke Tsurumaru, Akifumi Sugiyama, Yoshihiro Uto, Hitoshi Hori, Jun-Ichi Azuma, Kazufumi Yazaki. Characterization of coumarin-specific prenyltransferase activities in Citrus limon peel. Bioscience, biotechnology, and biochemistry. 2012; 76(7):1389-93. doi: 10.1271/bbb.120192. [PMID: 22785469]
  • 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]
  • Winnie Lai Ting Kan, Bin Ma, Ge Lin. Sulfur fumigation processing of traditional chinese medicinal herbs: beneficial or detrimental?. Frontiers in pharmacology. 2011; 2(?):84. doi: 10.3389/fphar.2011.00084. [PMID: 22207851]
  • Guo-Qang Liu, Jing Dong, Hong Wang, Yuki Hashi, Shi-Zhong Chen. Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry. European journal of mass spectrometry (Chichester, England). 2010; 16(2):215-20. doi: 10.1255/ejms.1070. [PMID: 20212330]
  • Soon Yew Tang, Irwin K Cheah, Huansong Wang, Barry Halliwell. Notopterygium forbesii Boiss extract and its active constituent phenethyl ferulate attenuate pro-inflammatory responses to lipopolysaccharide in RAW 264.7 macrophages. A "protective" role for oxidative stress?. Chemical research in toxicology. 2009 Aug; 22(8):1473-82. doi: 10.1021/tx900163h. [PMID: 19642688]
  • Aya Ishikawa, Tatsuya Kuma, Hiroyuki Sasaki, Nobuhiro Sasaki, Yoshihiro Ozeki, Nobuyuki Kobayashi, Yoshie Kitamura. Constitutive expression of bergaptol O-methyltransferase in Glehnia littoralis cell cultures. Plant cell reports. 2009 Feb; 28(2):257-65. doi: 10.1007/s00299-008-0631-9. [PMID: 18974989]
  • Toshifumi Hirata, Misato Fujii, Kazuhiro Akita, Noriyuki Yanaka, Kaori Ogawa, Masanori Kuroyanagi, Daiki Hongo. Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic & medicinal chemistry. 2009 Jan; 17(1):25-8. doi: 10.1016/j.bmc.2008.11.039. [PMID: 19054677]
  • Soon Yew Tang, Huansong Wang, Wenxia Zhang, Barry Halliwell. Notopterygium forbesii boiss extract and its active constituents increase reactive species and heme oxygenase-1 in human fetal hepatocytes: mechanisms of action. Chemical research in toxicology. 2008 Dec; 21(12):2414-23. doi: 10.1021/tx800301f. [PMID: 19548360]
  • 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]
  • Ya Zhao, Zhong Yuan. [A new coumarin glycoside from Glehnia littoralis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2007 Oct; 42(10):1070-3. doi: . [PMID: 18229615]
  • Victor Kuete, Robert Metuno, Bathélémy Ngameni, Armelle Mbaveng Tsafack, François Ngandeu, Ghislain Wabo Fotso, Merhatibeb Bezabih, François-Xavier Etoa, Bonaventure Tchaleu Ngadjui, Berhanu M Abegaz, Véronique Penlap Beng. Antimicrobial activity of the methanolic extracts and compounds from Treculia obovoidea (Moraceae). Journal of ethnopharmacology. 2007 Jul; 112(3):531-6. doi: 10.1016/j.jep.2007.04.010. [PMID: 17532157]
  • 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]
  • 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]
  • 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]
  • L K Chen, D E Cadwallader, H W Jun. Nitrofurantoin solubility in aqueous urea and creatinine solutions. Journal of pharmaceutical sciences. 1976 Jun; 65(6):868-72. doi: 10.1002/jps.2600650617. [PMID: 6782]
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