8-Prenylnaringenin (BioDeep_00000000399)

 

Secondary id: BioDeep_00000175273, BioDeep_00000268423

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2S)-

化学式: C20H20O5 (340.13106700000003)
中文名称: 8-异戊烯基柚皮素
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.05%

分子结构信息

SMILES: C/C(C)=C\Cc2c(O)cc(O)c3C(=O)C[C@@H](c1ccc(O)cc1)Oc23
InChI: InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3

描述信息

Sophoraflavanone B is a trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8. It has a role as a platelet aggregation inhibitor and a plant metabolite. It is a trihydroxyflavanone, a member of 4-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin. It is a conjugate acid of a sophoraflavanone B(1-).
8-Prenylnaringenin is a natural product found in Macaranga conifera, Macaranga denticulata, and other organisms with data available.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
A trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8.
INTERNAL_ID 2299; CONFIDENCE Reference Standard (Level 1)
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2299

同义名列表

27 个代谢物同义名

4H-1-BENZOPYRAN-4-ONE, 2,3-DIHYDRO-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2S)-; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one; (-)-(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one; 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-1-benzopyran-4-one; (S)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)CHROMAN-4-ONE; (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)chroman-4-one; 8-Prenylnaringenin, analytical standard; 8-Prenylnaringenin (Sophoraflavanone B); (-)-(2S)-8-dimethylallylnaringenin; (S)-8-dimethylallylnaringenin; LPEPZZAVFJPLNZ-SFHVURJKSA-N; 8-dimethylallylnaringenin; 8-prenylnaringenin (8-PN); (-)-8-Prenylnaringenin; (s)-8-prenylnaringenin; 8-prenyl-naringenin; 8-?Prenylnaringenin; Sophoraflavanone B; 8-Prenylnaringenin; UNII-5L872SZR8X; Flavaprenin; 5L872SZR8X; HOPEIN; YS04; 8-prenylnaringenin (MSe)



数据库引用编号

47 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

77 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

  • Atefeh Nasri, Raimo Pohjanvirta. Comparison of in vitro Toxicities of 8-Prenylnaringenin, Tartrazine and 17β-Estradiol, Representatives of Natural and Synthetic Estrogens, in Rat and Human Hepatoma Cell Lines. Endocrine research. 2024 Feb; 49(2):106-116. doi: 10.1080/07435800.2024.2337758. [PMID: 38597376]
  • Marcel Karabín, Tereza Haimannová, Kristýna Fialová, Lukáš Jelínek, Pavel Dostálek. Preparation of Hop Estrogen-Active Material for Production of Food Supplements. Molecules (Basel, Switzerland). 2021 Oct; 26(19):. doi: 10.3390/molecules26196065. [PMID: 34641609]
  • Marta Trius-Soler, María Marhuenda-Muñoz, Emily P Laveriano-Santos, Miriam Martínez-Huélamo, Gemma Sasot, Carolina E Storniolo, Ramon Estruch, Rosa M Lamuela-Raventós, Anna Tresserra-Rimbau. Moderate Consumption of Beer (with and without Ethanol) and Menopausal Symptoms: Results from a Parallel Clinical Trial in Postmenopausal Women. Nutrients. 2021 Jun; 13(7):. doi: 10.3390/nu13072278. [PMID: 34209273]
  • Alison K Hamm, Daniel K Manter, Jay S Kirkwood, Lisa M Wolfe, Kimberly Cox-York, Tiffany L Weir. The Effect of Hops (Humulus lupulus L.) Extract Supplementation on Weight Gain, Adiposity and Intestinal Function in Ovariectomized Mice. Nutrients. 2019 Dec; 11(12):. doi: 10.3390/nu11123004. [PMID: 31817899]
  • Jin-Bo Fang, Dejan Nikolić, David C Lankin, Charlotte Simmler, Shao-Nong Chen, Rene F Ramos Alvarenga, Yang Liu, Guido F Pauli, Richard B van Breemen. Formation of (2R)- and (2S)-8-Prenylnaringenin Glucuronides by Human UDP-Glucuronosyltransferases. Journal of agricultural and food chemistry. 2019 Oct; 67(42):11650-11656. doi: 10.1021/acs.jafc.9b04657. [PMID: 31554401]
  • Yanjun Zhang, Dexiong Zhou, Wei Liu, Chenguo Li, Lili Hao, Gaorong Zhang, Shengping Deng, Ruiyun Yang, Jiangke Qin, Jun Li, Wei Deng. Cytotoxic Activity and Related Mechanisms of Prenylflavonoids Isolated from Mallotus conspurcatus Croizat. Chemistry & biodiversity. 2019 May; 16(5):e1800465. doi: 10.1002/cbdv.201800465. [PMID: 30779297]
  • 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]
  • Judy L Bolton, Tareisha L Dunlap, Atieh Hajirahimkhan, Obinna Mbachu, Shao-Nong Chen, Luke Chadwick, Dejan Nikolic, Richard B van Breemen, Guido F Pauli, Birgit M Dietz. The Multiple Biological Targets of Hops and Bioactive Compounds. Chemical research in toxicology. 2019 02; 32(2):222-233. doi: 10.1021/acs.chemrestox.8b00345. [PMID: 30608650]
  • Atieh Hajirahimkhan, Obinna Mbachu, Charlotte Simmler, Sarah G Ellis, Huali Dong, Dejan Nikolic, David C Lankin, Richard B van Breemen, Shao-Nong Chen, Guido F Pauli, Birgit M Dietz, Judy L Bolton. Estrogen Receptor (ER) Subtype Selectivity Identifies 8-Prenylapigenin as an ERβ Agonist from Glycyrrhiza inflata and Highlights the Importance of Chemical and Biological Authentication. Journal of natural products. 2018 04; 81(4):966-975. doi: 10.1021/acs.jnatprod.7b01070. [PMID: 29641206]
  • Laura A Calvo-Castro, Markus Burkard, Nadine Sus, Gabriel Scheubeck, Christian Leischner, Ulrich M Lauer, Anja Bosy-Westphal, Verena Hund, Christian Busch, Sascha Venturelli, Jan Frank. The Oral Bioavailability of 8-Prenylnaringenin from Hops (Humulus Lupulus L.) in Healthy Women and Men is Significantly Higher than that of its Positional Isomer 6-Prenylnaringenin in a Randomized Crossover Trial. Molecular nutrition & food research. 2018 04; 62(7):e1700838. doi: 10.1002/mnfr.201700838. [PMID: 29363261]
  • Ilkay Erdogan Orhan, Dariusz Jedrejek, F Sezer Senol, Ramin Ekhteiari Salmas, Serdar Durdagi, Iwona Kowalska, Lukasz Pecio, Wieslaw Oleszek. Molecular modeling and in vitro approaches towards cholinesterase inhibitory effect of some natural xanthohumol, naringenin, and acyl phloroglucinol derivatives. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Mar; 42(?):25-33. doi: 10.1016/j.phymed.2018.03.009. [PMID: 29655693]
  • Raquel Costa, Ilda Rodrigues, Luísa Guardão, Sílvia Rocha-Rodrigues, Carolina Silva, José Magalhães, Manuel Ferreira-de-Almeida, Rita Negrão, Raquel Soares. Xanthohumol and 8-prenylnaringenin ameliorate diabetic-related metabolic dysfunctions in mice. The Journal of nutritional biochemistry. 2017 07; 45(?):39-47. doi: 10.1016/j.jnutbio.2017.03.006. [PMID: 28431322]
  • Raquel Costa, Ilda Rodrigues, Luísa Guardão, Joana Quelhas Lima, Emília Sousa, Raquel Soares, Rita Negrão. Modulation of VEGF signaling in a mouse model of diabetes by xanthohumol and 8-prenylnaringenin: Unveiling the angiogenic paradox and metabolism interplay. Molecular nutrition & food research. 2017 04; 61(4):. doi: 10.1002/mnfr.201600488. [PMID: 27921359]
  • Hyun Woo Lee, Hyung Won Ryu, Myung-Gyun Kang, Daeui Park, Sei-Ryang Oh, Hoon Kim. Potent selective monoamine oxidase B inhibition by maackiain, a pterocarpan from the roots of Sophora flavescens. Bioorganic & medicinal chemistry letters. 2016 10; 26(19):4714-4719. doi: 10.1016/j.bmcl.2016.08.044. [PMID: 27575476]
  • Fatemeh Abdi, Farideh Kazemi, Fahimeh Ramezani Tehrani, Nasibeh Roozbeh. Protocol for systematic review and meta-analysis: hop (Humulus lupulus L.) for menopausal vasomotor symptoms. BMJ open. 2016 Apr; 6(4):e010734. doi: 10.1136/bmjopen-2015-010734. [PMID: 27105715]
  • Martino Forino, Simona Pace, Giuseppina Chianese, Laura Santagostini, Markus Werner, Christina Weinigel, Silke Rummler, Gelsomina Fico, Oliver Werz, Orazio Taglialatela-Scafati. Humudifucol and Bioactive Prenylated Polyphenols from Hops (Humulus lupulus cv. "Cascade"). Journal of natural products. 2016 Mar; 79(3):590-7. doi: 10.1021/acs.jnatprod.5b01052. [PMID: 26918635]
  • Milou G M van de Schans, Tina Ritschel, Toine F H Bovee, Mark G Sanders, Pieter de Waard, Harry Gruppen, Jean-Paul Vincken. Involvement of a Hydrophobic Pocket and Helix 11 in Determining the Modes of Action of Prenylated Flavonoids and Isoflavonoids in the Human Estrogen Receptor. Chembiochem : a European journal of chemical biology. 2015 Dec; 16(18):2668-77. doi: 10.1002/cbic.201500343. [PMID: 26449282]
  • Richard B van Breemen. Development of Safe and Effective Botanical Dietary Supplements. Journal of medicinal chemistry. 2015 Nov; 58(21):8360-72. doi: 10.1021/acs.jmedchem.5b00417. [PMID: 26125082]
  • 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]
  • Yang Hee Jo, Seon Beom Kim, Qing Liu, Jin Woo Lee, Bang Yeon Hwang, Mi Kyeong Lee. Benzylated and prenylated flavonoids from the root barks of Cudrania tricuspidata with pancreatic lipase inhibitory activity. Bioorganic & medicinal chemistry letters. 2015 Sep; 25(17):3455-7. doi: 10.1016/j.bmcl.2015.07.017. [PMID: 26227773]
  • Jaeyoung Kwon, Sunita Basnet, Jin Woo Lee, Eun-Kyoung Seo, Nanzad Tsevegsuren, Bang Yeon Hwang, Dongho Lee. Chemical constituents isolated from the Mongolian medicinal plant Sophora alopecuroides L. and their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Bioorganic & medicinal chemistry letters. 2015 Aug; 25(16):3314-8. doi: 10.1016/j.bmcl.2015.05.062. [PMID: 26073007]
  • Christian Busch, Seema Noor, Christian Leischner, Markus Burkard, Ulrich M Lauer, Sascha Venturelli. Anti-proliferative activity of hop-derived prenylflavonoids against human cancer cell lines. Wiener medizinische Wochenschrift (1946). 2015 Jun; 165(11-12):258-61. doi: 10.1007/s10354-015-0355-8. [PMID: 25925225]
  • Corinna Urmann, Eleni Oberbauer, Sébastien Couillard-Després, Ludwig Aigner, Herbert Riepl. Neurodifferentiating potential of 8-prenylnaringenin and related compounds in neural precursor cells and correlation with estrogen-like activity. Planta medica. 2015 Mar; 81(4):305-11. doi: 10.1055/s-0034-1396243. [PMID: 25714726]
  • Annekathrin Martina Keiler, Peggy Dörfelt, Namita Chatterjee, Janina Helle, Manuela I Bader, Günter Vollmer, Georg Kretzschmar, Franziska Kuhlee, Detlef Thieme, Oliver Zierau. Assessment of the effects of naringenin-type flavanones in uterus and vagina. The Journal of steroid biochemistry and molecular biology. 2015 Jan; 145(?):49-57. doi: 10.1016/j.jsbmb.2014.10.001. [PMID: 25305411]
  • 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]
  • Kamila A Solak, Regiane R Santos, Martin van den Berg, Bas J Blaauboer, Bernard A J Roelen, Majorie B M van Duursen. Naringenin (NAR) and 8-prenylnaringenin (8-PN) reduce the developmental competence of porcine oocytes in vitro. Reproductive toxicology (Elmsford, N.Y.). 2014 Nov; 49(?):1-11. doi: 10.1016/j.reprotox.2014.05.013. [PMID: 24905140]
  • Stephanie E Martinez, Ted M Lakowski, Neal M Davies. Enantiospecific analysis of 8-prenylnaringenin in biological fluids by liquid-chromatography-electrospray ionization mass spectrometry: application to preclinical pharmacokinetic investigations. Chirality. 2014 Aug; 26(8):419-26. doi: 10.1002/chir.22343. [PMID: 24931510]
  • Janina Helle, Kristin Kräker, Manuela I Bader, Annekathrin M Keiler, Oliver Zierau, Günter Vollmer, JoEllen Welsh, Georg Kretzschmar. Assessment of the proliferative capacity of the flavanones 8-prenylnaringenin, 6-(1.1-dimethylallyl)naringenin and naringenin in MCF-7 cells and the rat mammary gland. Molecular and cellular endocrinology. 2014 Jul; 392(1-2):125-35. doi: 10.1016/j.mce.2014.05.014. [PMID: 24859648]
  • 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]
  • Mariane Cristovão Bagatin, Camila Santos Suniga Tozatti, Layara Akemi Abiko, Diego Alberto dos Santos Yamazaki, Priscila Rebeca Alves Silva, Leonardo Martins Perego, Elisabeth Aparecida Audi, Flavio Augusto Vicente Seixas, Ernani Abicht Basso, Gisele de Freitas Gauze. Molecular docking and panicolytic effect of 8-prenylnaringenin in the elevated T-maze. Chemical & pharmaceutical bulletin. 2014; 62(12):1231-7. doi: 10.1248/cpb.c14-00569. [PMID: 25450631]
  • 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]
  • Birgit M Dietz, Ghenet K Hagos, Jillian N Eskra, Gihani T Wijewickrama, Jeffrey R Anderson, Dejan Nikolic, Jian Guo, Brian Wright, Shao-Nong Chen, Guido F Pauli, Richard B van Breemen, Judy L Bolton. Differential regulation of detoxification enzymes in hepatic and mammary tissue by hops (Humulus lupulus) in vitro and in vivo. Molecular nutrition & food research. 2013 Jun; 57(6):1055-66. doi: 10.1002/mnfr.201200534. [PMID: 23512484]
  • Annekathrin M Keiler, Oliver Zierau, Georg Kretzschmar. Hop extracts and hop substances in treatment of menopausal complaints. Planta medica. 2013 May; 79(7):576-9. doi: 10.1055/s-0032-1328330. [PMID: 23512496]
  • Justyna Gąsiorowska, Andrzej Teisseyre, Anna Uryga, Krystyna Michalak. The influence of 8-prenylnaringenin on the activity of voltage-gated Kv1.3 potassium channels in human Jurkat T cells. Cellular & molecular biology letters. 2012 Dec; 17(4):559-70. doi: 10.2478/s11658-012-0029-0. [PMID: 22933043]
  • Clara Di Vito, Alessandra Bertoni, Michela Nalin, Sara Sampietro, Manuela Zanfa, Fabiola Sinigaglia. The phytoestrogen 8-prenylnaringenin inhibits agonist-dependent activation of human platelets. Biochimica et biophysica acta. 2012 Nov; 1820(11):1724-33. doi: 10.1016/j.bbagen.2012.06.018. [PMID: 22766195]
  • Jaroslav Matoušek, Tomáš Kocábek, Josef Patzak, Zoltán Füssy, Jitka Procházková, Arne Heyerick. Combinatorial analysis of lupulin gland transcription factors from R2R3Myb, bHLH and WDR families indicates a complex regulation of chs_H1 genes essential for prenylflavonoid biosynthesis in hop (Humulus Lupulus L.). BMC plant biology. 2012 Feb; 12(?):27. doi: 10.1186/1471-2229-12-27. [PMID: 22340661]
  • Y Wang, Y Chen, J Wang, J Chen, B B Aggarwal, X Pang, M Liu. Xanthohumol, a prenylated chalcone derived from hops, suppresses cancer cell invasion through inhibiting the expression of CXCR4 chemokine receptor. Current molecular medicine. 2012 Feb; 12(2):153-62. doi: 10.2174/156652412798889072. [PMID: 22172099]
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  • Ciska Wyns, Lara Derycke, Bram Soenen, Selin Bolca, Dieter Deforce, Marc Bracke, Arne Heyerick. Production of monoclonal antibodies against hop-derived (Humulus lupulus L.) prenylflavonoids and the development of immunoassays. Talanta. 2011 Jul; 85(1):197-205. doi: 10.1016/j.talanta.2011.03.047. [PMID: 21645689]
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