Isoxanthohumol (BioDeep_00000230032)

 

Secondary id: BioDeep_00000269455

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-

化学式: C21H22O5 (354.1467)
中文名称: (2S)-异黄腐酚, 异黄腐醇, 异黄腐酚, 2,3-二氢-7-羟基-2-(4-羟基苯基)-5-甲氧基-8-(3-甲基-2-丁烯基)-4H-1-苯并吡喃-4-酮
谱图信息: 最多检出来源 Viridiplantae(plant) 88.32%

分子结构信息

SMILES: C/C(C)=C\CC1=C2C(C(C[C@@H](C3=CC=C(O)C=C3)O2)=O)=C(OC)C=C1O
InChI: InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3

描述信息

Isoxanthohumol is a member of flavanones.
Isoxanthohumol is a natural product found in Streptomyces, Humulus lupulus, and Sophora flavescens with data available.
Isolated from hop (Humulus lupulus). Isoxanthohumol is a biomarker for the consumption of beer. Isoxanthohumol is found in beer and alcoholic beverages.
(2S)-Isoxanthohumol is a microbial biotransformed metabolite of the hop prenylflavanone Isoxanthohumol[1].
(2S)-Isoxanthohumol is a microbial biotransformed metabolite of the hop prenylflavanone Isoxanthohumol[1].
Isoxanthohumol is a prenylflavonoid from hops and beer. Isoxanthohumol exhibits an antiproliferative activity against several human cancer cell lines. Isoxanthohumol inhibits the development of lung metastatic foci in tumor-challenged animals. Isoxanthohumol shows an antiviral activity towards herpes viruses (HSV1 and HSV2) and bovine viral diarrhea virus (BVDV)[1][2].
Isoxanthohumol is a prenylflavonoid from hops and beer. Isoxanthohumol exhibits an antiproliferative activity against several human cancer cell lines. Isoxanthohumol inhibits the development of lung metastatic foci in tumor-challenged animals. Isoxanthohumol shows an antiviral activity towards herpes viruses (HSV1 and HSV2) and bovine viral diarrhea virus (BVDV)[1][2].

同义名列表

20 个代谢物同义名

4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-; 2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-4h-1-benzopyran-4-one; 7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methyl-2-butenyl)-2,3-dihydro-4H-chromen-4-one #; 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one; 7-hydroxy-2-(4-hydroxy-phenyl)-5-methoxy-8-(3-methyl-but-2-enyl)-chroman-4-one; 7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one; 7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chroman-4-one; Isoxanthohumol, primary pharmaceutical reference standard; 4,7-dihydroxy-5-methoxy-8-c-prenylflavanone; 4,7-dihydroxy-5-methoxy-8-prenylflavanone; Isoxanthohumol, analytical standard; Isoxanthohumol, >=99\\% (HPLC); Isoxanthohumol, HPLC Grade; Isoxanthohumol(Sophora); (+/-)-Isoxanthohumol; (2S)-Isoxanthohumol; UNII-B3BXQ4EZD6; Isoxanthohumol; SMP2_000215; isoxanthohumol (MSe)



数据库引用编号

25 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)

25 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


文献列表

  • Yoshiyuki Watanabe, Shiho Fujisaka, Yoshitomo Morinaga, Shiro Watanabe, Allah Nawaz, Hideki Hatta, Tomonobu Kado, Ayumi Nishimura, Muhammad Bilal, Muhammad Rahil Aslam, Keiko Honda, Yoshimi Nakagawa, Samir Softic, Kenichi Hirabayashi, Takashi Nakagawa, Yoshinori Nagai, Kazuyuki Tobe. Isoxanthohumol improves obesity and glucose metabolism via inhibiting intestinal lipid absorption with a bloom of Akkermansia muciniphila in mice. Molecular metabolism. 2023 Sep; ?(?):101797. doi: 10.1016/j.molmet.2023.101797. [PMID: 37709134]
  • Li Lin, Yuanyuan Chen, Qiang Li, Guang Xu, Kaixin Ding, Lutong Ren, Wei Shi, Yan Wang, Zhiyong Li, Wenzhang Dai, Ziying Wei, Yan Yang, Zhaofang Bai, Xiaohe Xiao. Isoxanthohumol, a component of Sophora flavescens, promotes the activation of the NLRP3 inflammasome and induces idiosyncratic hepatotoxicity. Journal of ethnopharmacology. 2022 Mar; 285(?):114796. doi: 10.1016/j.jep.2021.114796. [PMID: 34740771]
  • Magdalena Westermann, Amma G Adomako-Bonsu, Solveig Thiele, Serhat Sezai Çiçek, Hans-Jörg Martin, Edmund Maser. Inhibition of human carbonyl reducing enzymes by plant anthrone and anthraquinone derivatives. Chemico-biological interactions. 2022 Feb; 354(?):109823. doi: 10.1016/j.cbi.2022.109823. [PMID: 35065925]
  • Yin-Fang Yan, Tian-Lin Wu, Sha-Sha Du, Zheng-Rong Wu, Yong-Mei Hu, Zhi-Jun Zhang, Wen-Bin Zhao, Cheng-Jie Yang, Ying-Qian Liu. The Antifungal Mechanism of Isoxanthohumol from Humulus lupulus Linn. International journal of molecular sciences. 2021 Oct; 22(19):. doi: 10.3390/ijms221910853. [PMID: 34639194]
  • Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
  • Lidia Daimiel, Víctor Micó, Laura Díez-Ricote, Paloma Ruiz-Valderrey, Geoffrey Istas, Ana Rodríguez-Mateos, José María Ordovás. Alcoholic and Non-Alcoholic Beer Modulate Plasma and Macrophage microRNAs Differently in a Pilot Intervention in Humans with Cardiovascular Risk. Nutrients. 2020 Dec; 13(1):. doi: 10.3390/nu13010069. [PMID: 33379359]
  • M Yamashita, S Fukizawa, Y Nonaka. Hop-derived prenylflavonoid isoxanthohumol suppresses insulin resistance by changing the intestinal microbiota and suppressing chronic inflammation in high fat diet-fed mice. European review for medical and pharmacological sciences. 2020 02; 24(3):1537-1547. doi: 10.26355/eurrev_202002_20212. [PMID: 32096203]
  • Tamara Krajnović, Dijana Drača, Goran N Kaluđerović, Duško Dunđerović, Ivana Mirkov, Ludger A Wessjohann, Danijela Maksimović-Ivanić, Sanja Mijatović. The hop-derived prenylflavonoid isoxanthohumol inhibits the formation of lung metastasis in B16-F10 murine melanoma model. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2019 Jul; 129(?):257-268. doi: 10.1016/j.fct.2019.04.046. [PMID: 31034931]
  • Martin Ambrož, Kateřina Lněničková, Petra Matoušková, Lenka Skálová, Iva Boušová. Antiproliferative Effects of Hop-derived Prenylflavonoids and Their Influence on the Efficacy of Oxaliplatine, 5-fluorouracil and Irinotecan in Human ColorectalC Cells. Nutrients. 2019 Apr; 11(4):. doi: 10.3390/nu11040879. [PMID: 31010128]
  • Jun Inoue, Shingo Miyata, Makoto Shimizu, Ryuichiro Sato. Isoxanthohumol stimulates ubiquitin-proteasome-dependent degradation of precursor forms of sterol regulatory element-binding proteins. Bioscience, biotechnology, and biochemistry. 2018 Sep; 82(9):1591-1598. doi: 10.1080/09168451.2018.1478715. [PMID: 29804513]
  • Paola Quifer-Rada, Gemma Chiva-Blanch, Olga Jáuregui, Ramon Estruch, Rosa M Lamuela-Raventós. A discovery-driven approach to elucidate urinary metabolome changes after a regular and moderate consumption of beer and nonalcoholic beer in subjects at high cardiovascular risk. Molecular nutrition & food research. 2017 10; 61(10):. doi: 10.1002/mnfr.201600980. [PMID: 28608394]
  • V F Kulikovskii, E T Zhilyakova, O O Novikov, D I Pisarev, N V Prokushchenko, L L Ivanova. Study of Sedative Tea Phytocomplex within the Framework of Studies Aimed at Creation of a Rectal Dosage Form with Antihistaminic Effect. Bulletin of experimental biology and medicine. 2017 Oct; 163(6):753-756. doi: 10.1007/s10517-017-3896-6. [PMID: 29063320]
  • Tamara Krajnović, Goran N Kaluđerović, Ludger A Wessjohann, Sanja Mijatović, Danijela Maksimović-Ivanić. Versatile antitumor potential of isoxanthohumol: Enhancement of paclitaxel activity in vivo. Pharmacological research. 2016 Mar; 105(?):62-73. doi: 10.1016/j.phrs.2016.01.011. [PMID: 26784390]
  • Christian Büchter, Susannah Havermann, Karoline Koch, Wim Wätjen. Isoxanthohumol, a constituent of hop (Humulus lupulus L.), increases stress resistance in Caenorhabditis elegans dependent on the transcription factor DAF-16. European journal of nutrition. 2016 Feb; 55(1):257-65. doi: 10.1007/s00394-015-0843-z. [PMID: 25644181]
  • Stephanie E Martinez, Neal M Davies. Enantiospecific pharmacokinetics of isoxanthohumol and its metabolite 8-prenylnaringenin in the rat. Molecular nutrition & food research. 2015 Sep; 59(9):1674-89. doi: 10.1002/mnfr.201500118. [PMID: 26079861]
  • Monika Stompor, Katarzyna Dancewicz, Beata Gabryś, Mirosław Anioł. Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and Their Derivatives. Journal of agricultural and food chemistry. 2015 Aug; 63(30):6749-56. doi: 10.1021/acs.jafc.5b02025. [PMID: 26176501]
  • Anna Katarzyna Żołnierczyk, Wanda Krystyna Mączka, Małgorzata Grabarczyk, Katarzyna Wińska, Edyta Woźniak, Mirosław Anioł. Isoxanthohumol--Biologically active hop flavonoid. Fitoterapia. 2015 Jun; 103(?):71-82. doi: 10.1016/j.fitote.2015.03.007. [PMID: 25771121]
  • René F Ramos Alvarenga, J Brent Friesen, Dejan Nikolić, Charlotte Simmler, José G Napolitano, Richard van Breemen, David C Lankin, James B McAlpine, Guido F Pauli, Shao-Nong Chen. K-targeted metabolomic analysis extends chemical subtraction to DESIGNER extracts: selective depletion of extracts of hops (Humulus lupulus). Journal of natural products. 2014 Dec; 77(12):2595-604. doi: 10.1021/np500376g. [PMID: 25437744]
  • Kee W Tan, Janine Cooney, Dwayne Jensen, Yan Li, James W Paxton, Nigel P Birch, Arjan Scheepens. Hop-derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2). Molecular nutrition & food research. 2014 Nov; 58(11):2099-110. doi: 10.1002/mnfr.201400288. [PMID: 25044854]
  • Paola Quifer-Rada, Miriam Martínez-Huélamo, Gemma Chiva-Blanch, Olga Jáuregui, Ramon Estruch, Rosa M Lamuela-Raventós. Urinary isoxanthohumol is a specific and accurate biomarker of beer consumption. The Journal of nutrition. 2014 Apr; 144(4):484-8. doi: 10.3945/jn.113.185199. [PMID: 24477299]
  • LeeCole Legette, Chanida Karnpracha, Ralph L Reed, Jaewoo Choi, Gerd Bobe, J Mark Christensen, Rosita Rodriguez-Proteau, Jonathan Q Purnell, Jan F Stevens. Human pharmacokinetics of xanthohumol, an antihyperglycemic flavonoid from hops. Molecular nutrition & food research. 2014 Feb; 58(2):248-55. doi: 10.1002/mnfr.201300333. [PMID: 24038952]
  • Ayane Kiyofuji, Kazuki Yui, Koki Takahashi, Kyoichi Osada. Effects of xanthohumol-rich hop extract on the differentiation of preadipocytes. Journal of oleo science. 2014; 63(6):593-7. doi: 10.5650/jos.ess14009. [PMID: 24829131]
  • Olga Wesołowska, Justyna Gąsiorowska, Joanna Petrus, Bogusława Czarnik-Matusewicz, Krystyna Michalak. Interaction of prenylated chalcones and flavanones from common hop with phosphatidylcholine model membranes. Biochimica et biophysica acta. 2014 Jan; 1838(1 Pt B):173-84. doi: 10.1016/j.bbamem.2013.09.009. [PMID: 24060562]
  • Philip Allsopp, Sam Possemiers, David Campbell, Chris Gill, Ian Rowland. A comparison of the anticancer properties of isoxanthohumol and 8-prenylnaringenin using in vitro models of colon cancer. BioFactors (Oxford, England). 2013 Jul; 39(4):441-7. doi: 10.1002/biof.1084. [PMID: 23361834]
  • Paola Quifer-Rada, Miriam Martínez-Huélamo, Olga Jáuregui, Gemma Chiva-Blanch, Ramón Estruch, Rosa M Lamuela-Raventós. Analytical condition setting a crucial step in the quantification of unstable polyphenols in acidic conditions: analyzing prenylflavanoids in biological samples by liquid chromatography-electrospray ionization triple quadruple mass spectrometry. Analytical chemistry. 2013 Jun; 85(11):5547-54. doi: 10.1021/ac4007733. [PMID: 23642016]
  • Gaia Izzo, Olle Söder, Konstantin Svechnikov. The prenylflavonoid phytoestrogens 8-prenylnaringenin and isoxanthohumol diferentially suppress steroidogenesis in rat Leydig cells in ontogenesis. Journal of applied toxicology : JAT. 2011 Aug; 31(6):589-94. doi: 10.1002/jat.1602. [PMID: 21061451]
  • Dennis Stracke, Tobias Schulz, Peter Prehm. Inhibitors of hyaluronan export from hops prevent osteoarthritic reactions. Molecular nutrition & food research. 2011 Mar; 55(3):485-94. doi: 10.1002/mnfr.201000210. [PMID: 20848398]
  • Laura Hanske, Gunnar Loh, Silke Sczesny, Michael Blaut, Annett Braune. Recovery and metabolism of xanthohumol in germ-free and human microbiota-associated rats. Molecular nutrition & food research. 2010 Oct; 54(10):1405-13. doi: 10.1002/mnfr.200900517. [PMID: 20397197]
  • Cassia R Overk, Jian Guo, Lucas R Chadwick, Daniel D Lantvit, Alberto Minassi, Giovanni Appendino, Shao-Nong Chen, David C Lankin, Norman R Farnsworth, Guido F Pauli, Richard B van Breemen, Judy L Bolton. In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin. Chemico-biological interactions. 2008 Oct; 176(1):30-9. doi: 10.1016/j.cbi.2008.06.005. [PMID: 18619951]
  • Wei Li, Hong Liang, Ting Yin, Bin Wang, Yu-Ying Zhao. [Main flavonoids from Sophora flavescenes]. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 Aug; 43(8):833-7. doi: . [PMID: 18956776]
  • Eun Mi Hwang, Young Bae Ryu, Hoi Young Kim, Dong-Gyu Kim, Seong-Geun Hong, Jin Hwan Lee, Marcus J Curtis-Long, Seong Hun Jeong, Jae-Yong Park, Ki Hun Park. BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens. Bioorganic & medicinal chemistry. 2008 Jul; 16(14):6669-74. doi: 10.1016/j.bmc.2008.05.080. [PMID: 18565755]
  • Sam Possemiers, Sylvie Rabot, Juan Carlos Espín, Aurélia Bruneau, Catherine Philippe, Antonio González-Sarrías, Arne Heyerick, Francisco A Tomás-Barberán, Denis De Keukeleire, Willy Verstraete. Eubacterium limosum activates isoxanthohumol from hops (Humulus lupulus L.) into the potent phytoestrogen 8-prenylnaringenin in vitro and in rat intestine. The Journal of nutrition. 2008 Jul; 138(7):1310-6. doi: 10.1093/jn/138.7.1310. [PMID: 18567753]
  • L Delmulle, T Vanden Berghe, D De Keukeleire, P Vandenabeele. Treatment of PC-3 and DU145 prostate cancer cells by prenylflavonoids from hop (Humulus lupulus L.) induces a caspase-independent form of cell death. Phytotherapy research : PTR. 2008 Feb; 22(2):197-203. doi: 10.1002/ptr.2286. [PMID: 17726738]
  • Jeong-Yeh Yang, Mary Anne Della-Fera, Srujana Rayalam, Clifton A Baile. Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Apoptosis : an international journal on programmed cell death. 2007 Nov; 12(11):1953-63. doi: 10.1007/s10495-007-0130-4. [PMID: 17874298]
  • Selin Bolca, Sam Possemiers, Veerle Maervoet, Inge Huybrechts, Arne Heyerick, Stefaan Vervarcke, Herman Depypere, Denis De Keukeleire, Marc Bracke, Stefaan De Henauw, Willy Verstraete, Tom Van de Wiele. Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women. The British journal of nutrition. 2007 Nov; 98(5):950-9. doi: 10.1017/s0007114507749243. [PMID: 17521469]
  • Lei Zhang, Liang Xu, Shan-Shan Xiao, Qiong-Feng Liao, Qing Li, Jian Liang, Xiao-Hui Chen, Kai-Shun Bi. Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2007 Sep; 44(5):1019-28. doi: 10.1016/j.jpba.2007.04.019. [PMID: 17658714]
  • Hee Jin Jung, Sam Sik Kang, Sook Kyung Hyun, Jae Sue Choi. In vitro free radical and ONOO- scavengers from Sophora flavescens. Archives of pharmacal research. 2005 May; 28(5):534-40. doi: 10.1007/bf02977754. [PMID: 15974438]
  • Victor E Buckwold, Richard J H Wilson, Aysegul Nalca, Brigitte B Beer, Thomas G Voss, Jim A Turpin, Robert W Buckheit, Jiayi Wei, Michelle Wenzel-Mathers, Eve M Walton, Robert J Smith, Melanie Pallansch, Priscilla Ward, Jay Wells, Lara Chuvala, Sandra Sloane, Robin Paulman, Julie Russell, Tracy Hartman, Roger Ptak. Antiviral activity of hop constituents against a series of DNA and RNA viruses. Antiviral research. 2004 Jan; 61(1):57-62. doi: 10.1016/s0166-3542(03)00155-4. [PMID: 14670594]