Lupulone (BioDeep_00000008268)

 

Secondary id: BioDeep_00000276420

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione

化学式: C26H38O4 (414.277)
中文名称: 蛇麻酮
谱图信息: 最多检出来源 Viridiplantae(plant) 12.12%

分子结构信息

SMILES: C1(=C(C(=C(C(=O)C1(CC=C(C)C)CC=C(C)C)CC=C(C)C)O)C(=O)CC(C)C)O
InChI: InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28,30H,10,13-15H2,1-8H3

描述信息

Lupulone is found in alcoholic beverages. Lupulone is a constituent of hops

同义名列表

10 个代谢物同义名

5-hydroxy-2,6,6-tris(3-methylbut-2-en-1-yl)-4-(3-methylbutanoyl)cyclohex-4-ene-1,3-dione; beta-Lupulic acid; b-Lupulinic acid; beta-Bitter acid; b-Lupulic acid; b-Bitter acid; Lupulone; lupulon; B -Acid; Lupulone



数据库引用编号

20 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)

26 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 12 AIMP2, ANG, BCL2, CASP3, CASP8, FAS, FDPS, HPS1, MAPK8, MCL1, MSMP, TRPC6
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 3 BCL2, CANX, CYP1B1
Mitochondrion membrane 1 CANX
Nucleus 8 AIMP2, ANG, BCL2, CASP3, CASP8, FASLG, MAPK8, MCL1
cytosol 10 AIMP2, ANG, BCL2, CASP3, CASP8, FAS, FDPS, HPS1, MAPK8, MCL1
mitochondrial membrane 1 CANX
nuclear body 1 FAS
nucleoplasm 5 CASP3, CASP8, FDPS, MAPK8, MCL1
Cell membrane 4 FAS, FASLG, TNF, TRPC6
lamellipodium 1 CASP8
Multi-pass membrane protein 2 SLC9C1, TRPC6
Synapse 1 MAPK8
cell surface 3 FAS, TNF, TNFRSF10B
glutamatergic synapse 1 CASP3
Golgi apparatus 1 FAS
growth cone 1 ANG
lysosomal membrane 1 GAA
neuronal cell body 3 ANG, CASP3, TNF
Cytoplasm, cytosol 1 AIMP2
Lysosome 2 GAA, HPS1
Presynapse 1 CANX
plasma membrane 7 FAS, FASLG, GAA, SLC9C1, TNF, TNFRSF10B, TRPC6
Membrane 12 AIMP2, BCL2, CANX, CYP1B1, FAS, FASLG, FDPS, GAA, MCL1, SLC9C1, TNFRSF10B, TRPC6
axon 1 MAPK8
caveola 1 FASLG
extracellular exosome 5 CANX, FAS, FASLG, GAA, LCN2
Lysosome membrane 1 GAA
endoplasmic reticulum 2 BCL2, CANX
extracellular space 5 ANG, FASLG, LCN2, MSMP, TNF
lysosomal lumen 2 FASLG, GAA
perinuclear region of cytoplasm 1 FASLG
mitochondrion 4 BCL2, CASP8, CYP1B1, MCL1
protein-containing complex 2 BCL2, CASP8
intracellular membrane-bounded organelle 2 CYP1B1, GAA
Microsome membrane 1 CYP1B1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 CANX, FAS
Secreted 5 ANG, FASLG, GAA, LCN2, MSMP
extracellular region 5 ANG, FASLG, GAA, LCN2, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 3 BCL2, CANX, MCL1
mitochondrial outer membrane 3 BCL2, CASP8, MCL1
mitochondrial matrix 1 FDPS
Cytoplasmic vesicle lumen 2 FASLG, LCN2
motile cilium 1 SLC9C1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 2 BCL2, MCL1
nuclear membrane 2 BCL2, CANX
external side of plasma membrane 3 FAS, FASLG, TNF
actin cytoskeleton 1 ANG
slit diaphragm 1 TRPC6
cytoplasmic vesicle 1 HPS1
nucleolus 1 ANG
Melanosome membrane 1 CANX
recycling endosome 1 TNF
Single-pass type II membrane protein 2 FASLG, TNF
Cell projection, lamellipodium 1 CASP8
Membrane raft 2 FAS, TNF
pore complex 1 BCL2
Peroxisome 1 FDPS
basement membrane 1 ANG
phagocytic cup 1 TNF
Chromosome 1 ANG
cytoskeleton 1 CASP8
Nucleus, nucleolus 1 ANG
Cell projection, cilium, flagellum membrane 1 SLC9C1
mitochondria-associated endoplasmic reticulum membrane contact site 1 CANX
myosin complex 1 MCL1
Nucleus, nucleoplasm 1 MCL1
tertiary granule membrane 1 GAA
Melanosome 1 FAS
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
cell body 1 CASP8
myelin sheath 1 BCL2
endoplasmic reticulum quality control compartment 1 CANX
endoplasmic reticulum lumen 1 CANX
specific granule lumen 1 LCN2
endocytic vesicle 1 ANG
azurophil granule membrane 1 GAA
Lysosome lumen 1 FASLG
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 2 CASP8, FAS
death-inducing signaling complex 3 CASP3, CASP8, FAS
ripoptosome 1 CASP8
lumenal side of endoplasmic reticulum membrane 1 CANX
[Isoform 1]: Cell membrane 1 FAS
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
angiogenin-PRI complex 1 ANG
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
[Tumor necrosis factor ligand superfamily member 6, soluble form]: Secreted 1 FASLG
[FasL intracellular domain]: Nucleus 1 FASLG
cation channel complex 1 TRPC6
glycogen granule 1 FAS
Cytoplasmic granule lumen 1 LCN2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
BLOC-3 complex 1 HPS1


文献列表

  • Lena Decuyper, Gurkirat Kaur, Charlotte Versyck, Eline Blondeel, Yves Depetter, Kristof Van Hecke, Matthias D'hooghe. Expedient Synthesis of Lupulones and Their Derivatization to 2,8-7H-Dihydrochromen-7-ones. ChemistryOpen. 2020 04; 9(4):442-444. doi: 10.1002/open.202000008. [PMID: 32269899]
  • Xiaojia Guo, Hongwei Shen, Yuxue Liu, Qian Wang, Xueying Wang, Chang Peng, Wujun Liu, Zongbao K Zhao. Enabling Heterologous Synthesis of Lupulones in the Yeast Saccharomyces cerevisiae. Applied biochemistry and biotechnology. 2019 Jul; 188(3):787-797. doi: 10.1007/s12010-019-02957-8. [PMID: 30684240]
  • Carolin Schulz, Chafia Chiheb, Monika Pischetsrieder. Quantification of co-, n-, and ad-lupulone in hop-based dietary supplements and phytopharmaceuticals and modulation of their contents by the extraction method. Journal of pharmaceutical and biomedical analysis. 2019 May; 168(?):124-132. doi: 10.1016/j.jpba.2019.02.022. [PMID: 30807916]
  • Carolin Schulz, Nikolas Fritz, Thomas Sommer, Karel Krofta, Kristina Friedland, Monika Pischetsrieder. Activation of membrane-located Ca2+ channels by hop beta acids and their tricyclic transformation products. Food chemistry. 2018 Jun; 252(?):215-227. doi: 10.1016/j.foodchem.2018.01.073. [PMID: 29478534]
  • Katerina Bogdanova, Magdalena Röderova, Milan Kolar, Katerina Langova, Martin Dusek, Petr Jost, Klara Kubelkova, Pavel Bostik, Jana Olsovska. Antibiofilm activity of bioactive hop compounds humulone, lupulone and xanthohumol toward susceptible and resistant staphylococci. Research in microbiology. 2018 Apr; 169(3):127-134. doi: 10.1016/j.resmic.2017.12.005. [PMID: 29407045]
  • Pavel Cermak, Jana Olsovska, Alexandr Mikyska, Martin Dusek, Zuzana Kadleckova, Jiri Vanicek, Otakar Nyc, Karel Sigler, Vanda Bostikova, Pavel Bostik. Strong antimicrobial activity of xanthohumol and other derivatives from hops (Humulus lupulus L.) on gut anaerobic bacteria. APMIS : acta pathologica, microbiologica, et immunologica Scandinavica. 2017 Nov; 125(11):1033-1038. doi: 10.1111/apm.12747. [PMID: 28960474]
  • Jaroslav Matoušek, Tomáš Kocábek, Josef Patzak, Jindřich Bříza, Kristýna Siglová, Ajay Kumar Mishra, Ganesh Selvaraj Duraisamy, Anna Týcová, Eiichiro Ono, Karel Krofta. The "putative" role of transcription factors from HlWRKY family in the regulation of the final steps of prenylflavonid and bitter acids biosynthesis in hop (Humulus lupulus L.). Plant molecular biology. 2016 Oct; 92(3):263-77. doi: 10.1007/s11103-016-0510-7. [PMID: 27392499]
  • Mariam Gaid, Paul Haas, Till Beuerle, Stephan Scholl, Ludger Beerhues. Hyperforin production in Hypericum perforatum root cultures. Journal of biotechnology. 2016 Mar; 222(?):47-55. doi: 10.1016/j.jbiotec.2016.02.016. [PMID: 26876610]
  • B E Harlow, L M Lawrence, I A Kagan, M D Flythe. Inhibition of fructan-fermenting equine faecal bacteria and Streptococcus bovis by hops (Humulus lupulus L.) β-acid. Journal of applied microbiology. 2014 Aug; 117(2):329-39. doi: 10.1111/jam.12532. [PMID: 24775300]
  • Petros X E Mouratidis, Kay W Colston, Matthew L Tucknott, Elizabeth Tyrrell, Grisha Pirianov. An investigation into the anticancer effects and mechanism of action of hop β-acid lupulone and its natural and synthetic derivatives in prostate cancer cells. Nutrition and cancer. 2013; 65(7):1086-92. doi: 10.1080/01635581.2013.850963. [PMID: 24168111]
  • Michael Saugspier, Christoph Dorn, Barbara Czech, Manfred Gehrig, Jörg Heilmann, Claus Hellerbrand. Hop bitter acids inhibit tumorigenicity of hepatocellular carcinoma cells in vitro. Oncology reports. 2012 Oct; 28(4):1423-8. doi: 10.3892/or.2012.1925. [PMID: 22825405]
  • Yusuke Tsurumaru, Kanako Sasaki, Tatsuya Miyawaki, Yoshihiro Uto, Takayuki Momma, Naoyuki Umemoto, Masaki Momose, Kazufumi Yazaki. HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops. Biochemical and biophysical research communications. 2012 Jan; 417(1):393-8. doi: 10.1016/j.bbrc.2011.11.125. [PMID: 22166201]
  • Florian Emerstorfer, Walter Hein, Reinhard Resch, Erich M Poetsch, Ulrike Zitz, Wolfgang Kneifel. Application of plant-based antimicrobials for the growth inhibition of clostridia in pressed beet pulp silage. Journal of the science of food and agriculture. 2011 Aug; 91(11):2038-44. doi: 10.1002/jsfa.4416. [PMID: 21495041]
  • Marjan Van Cleemput, Ko Cattoor, Karolien De Bosscher, Guy Haegeman, Denis De Keukeleire, Arne Heyerick. Hop (Humulus lupulus)-derived bitter acids as multipotent bioactive compounds. Journal of natural products. 2009 Jun; 72(6):1220-30. doi: 10.1021/np800740m. [PMID: 19476340]
  • Naoto Yamaguchi, Keiko Satoh-Yamaguchi, Mitsunori Ono. In vitro evaluation of antibacterial, anticollagenase, and antioxidant activities of hop components (Humulus lupulus) addressing acne vulgaris. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2009 Apr; 16(4):369-76. doi: 10.1016/j.phymed.2008.12.021. [PMID: 19201179]
  • O Kornysova, Z Stanius, K Obelevicius, O Ragazinskiene, E Skrzydlewska, A Maruska. Capillary zone electrophoresis method for determination of bitter (alpha- and beta-) acids in hop (Humulus lupulus L.) cone extracts. Advances in medical sciences. 2009; 54(1):41-6. doi: 10.2478/v10039-009-0020-9. [PMID: 19581204]
  • P Natarajan, S Katta, I Andrei, V Babu Rao Ambati, M Leonida, G J Haas. Positive antibacterial co-action between hop (Humulus lupulus) constituents and selected antibiotics. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 Mar; 15(3):194-201. doi: 10.1016/j.phymed.2007.10.008. [PMID: 18162387]
  • Virginie Lamy, Stamatiki Roussi, Mehdi Chaabi, Francine Gossé, Nicolas Schall, Annelise Lobstein, Francis Raul. Chemopreventive effects of lupulone, a hop {beta}-acid, on human colon cancer-derived metastatic SW620 cells and in a rat model of colon carcinogenesis. Carcinogenesis. 2007 Jul; 28(7):1575-81. doi: 10.1093/carcin/bgm080. [PMID: 17434926]
  • Jelle De Keukeleire, Geert Ooms, Arne Heyerick, Isabel Roldan-Ruiz, Erik Van Bockstaele, Denis De Keukeleire. Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.). Journal of agricultural and food chemistry. 2003 Jul; 51(15):4436-41. doi: 10.1021/jf034263z. [PMID: 12848522]
  • M Tagashira, M Watanabe, N Uemitsu. Antioxidative activity of hop bitter acids and their analogues. Bioscience, biotechnology, and biochemistry. 1995 Apr; 59(4):740-2. doi: 10.1271/bbb.59.740. [PMID: 7772843]
  • L E SACKS, E M HUMPHREYS. Antagonistic effect of serum on bacteriostatic action of lupulone. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1951 Feb; 76(2):234-8. doi: 10.3181/00379727-76-18446. [PMID: 14827882]
  • H D MICHENER, N SNELL, E F JANSEN. Antifungal activity of hop resin constituents and a new method for isolation of lupulon. Archives of biochemistry. 1948 Nov; 19(2):199-208. doi: ". [PMID: 18891772]
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