8-Prenylnaringenin (BioDeep_00000175273)

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

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 () 0%

分子结构信息

SMILES: CC(=CCC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC=C(C=C3)O)C
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

(s)-4,5,7-trihydroxy-8-prenylflavanone is a member of the class of compounds known as 8-prenylated flavanones. 8-prenylated flavanones are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, (s)-4,5,7-trihydroxy-8-prenylflavanone is considered to be a flavonoid lipid molecule (s)-4,5,7-trihydroxy-8-prenylflavanone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-4,5,7-trihydroxy-8-prenylflavanone can be found in beer, which makes (s)-4,5,7-trihydroxy-8-prenylflavanone a potential biomarker for the consumption of this food product.

同义名列表

4 个代谢物同义名

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one; (S)-4,5,7-Trihydroxy-8-prenylflavanone; Sophoraflavanone B; 8-Prenylnaringenin

数据库引用编号

7 个数据库交叉引用编号

ChEBI: CHEBI:188606
PubChem: 509245
HMDB: HMDB0247465
ChEMBL: CHEMBL460647
foodb: FDB012291
CAS: 68682-02-0
CAS: 53846-50-7

分类词条

8-prenylated flavanones

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)

20 个相关的物种来源信息

357850 - Angelica keiskei: 10.1021/NP058080D
194251 - Artocarpus altilis: 10.1021/NP0600346
124943 - Azadirachta indica: 10.1021/JF034666Z
1835378 - Brosimum acutifolium: 10.1016/S0031-9422(99)00608-1
429560 - Cullen corylifolium: 10.1016/J.PHYMED.2013.09.015
3845 - Erythrina variegata: 10.1016/0031-9422(90)85056-L
49827 - Glycyrrhiza glabra: 10.1248/CPB.51.1147
74614 - Glycyrrhiza inflata: 10.1248/CPB.51.1147
9606 - Homo sapiens: -
3484 - Humulus: 10.1016/J.JEP.2008.01.011
701533 - Lespedeza cyrtobotrya: 10.1021/NP800535G
396452 - Macaranga bicolor: 10.1016/S0031-9422(02)00378-3
194324 - Maclura cochinchinensis: 10.1021/NP000406P
210328 - Maclura tricuspidata: 10.1016/J.BMCL.2015.07.017
1448043 - Marshallia grandiflora: 10.1016/0031-9422(79)80156-9
931589 - Propolis: 10.1021/NP9002433
200492 - Sophora alopecuroides:
49840 - Sophora flavescens:
1323965 - Sophora moorcroftiana:
256637 - Sophora tomentosa:

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

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]
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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]
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]
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Zuzana Kyselova. Toxicological aspects of the use of phenolic compounds in disease prevention. Interdisciplinary toxicology. 2011 Dec; 4(4):173-83. doi: 10.2478/v10102-011-0027-5. [PMID: 22319251]
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]
Rudy Simons, Jean-Paul Vincken, Loes A M Mol, Susan A M The, Toine F H Bovee, Teus J C Luijendijk, Marian A Verbruggen, Harry Gruppen. Agonistic and antagonistic estrogens in licorice root (Glycyrrhiza glabra). Analytical and bioanalytical chemistry. 2011 Jul; 401(1):305-13. doi: 10.1007/s00216-011-5061-9. [PMID: 21573846]
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Rita Negrão, Raquel Costa, Delfim Duarte, Tiago Taveira Gomes, Mário Mendanha, Liane Moura, Luísa Vasques, Isabel Azevedo, Raquel Soares. Angiogenesis and inflammation signaling are targets of beer polyphenols on vascular cells. Journal of cellular biochemistry. 2010 Dec; 111(5):1270-9. doi: 10.1002/jcb.22850. [PMID: 20803553]
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Elena Biagi, Lotta Nylund, Marco Candela, Rita Ostan, Laura Bucci, Elisa Pini, Janne Nikkïla, Daniela Monti, Reetta Satokari, Claudio Franceschi, Patrizia Brigidi, Willem De Vos. Through ageing, and beyond: gut microbiota and inflammatory status in seniors and centenarians. PloS one. 2010 May; 5(5):e10667. doi: 10.1371/journal.pone.0010667. [PMID: 20498852]
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Ciska Wyns, Selin Bolca, Denis De Keukeleire, Arne Heyerick. Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Apr; 878(13-14):949-56. doi: 10.1016/j.jchromb.2010.02.022. [PMID: 20299290]
Ana M Fortes, Filipa Santos, Maria S Pais. Organogenic nodule formation in hop: a tool to study morphogenesis in plants with biotechnological and medicinal applications. Journal of biomedicine & biotechnology. 2010; 2010(?):. doi: 10.1155/2010/583691. [PMID: 20811599]
Georg Kretzschmar, Oliver Zierau, Jannette Wober, Sandra Tischer, Peter Metz, Günter Vollmer. Prenylation has a compound specific effect on the estrogenicity of naringenin and genistein. The Journal of steroid biochemistry and molecular biology. 2010 Jan; 118(1-2):1-6. doi: 10.1016/j.jsbmb.2009.08.005. [PMID: 19733663]
Elisa Brunelli, Giulia Pinton, Paolo Bellini, Alberto Minassi, Giovanni Appendino, Laura Moro. Flavonoid-induced autophagy in hormone sensitive breast cancer cells. Fitoterapia. 2009 Sep; 80(6):327-32. doi: 10.1016/j.fitote.2009.04.002. [PMID: 19371773]
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Elisa Brunelli, Giulia Pinton, Federica Chianale, Andrea Graziani, Giovanni Appendino, Laura Moro. 8-Prenylnaringenin inhibits epidermal growth factor-induced MCF-7 breast cancer cell proliferation by targeting phosphatidylinositol-3-OH kinase activity. The Journal of steroid biochemistry and molecular biology. 2009 Feb; 113(3-5):163-70. doi: 10.1016/j.jsbmb.2008.11.013. [PMID: 19103290]
Joan Vermeiren, Tom Van de Wiele, Willy Verstraete, Pascal Boeckx, Nico Boon. Nitric oxide production by the human intestinal microbiota by dissimilatory nitrate reduction to ammonium. Journal of biomedicine & biotechnology. 2009; 2009(?):284718. doi: 10.1155/2009/284718. [PMID: 19888436]
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]
Mario Dell'Agli, Germana V Galli, Esther Dal Cero, Federica Belluti, Riccardo Matera, Elisa Zironi, Giampiero Pagliuca, Enrica Bosisio. Potent inhibition of human phosphodiesterase-5 by icariin derivatives. Journal of natural products. 2008 Sep; 71(9):1513-7. doi: 10.1021/np800049y. [PMID: 18778098]
Martina Böttner, Julie Christoffel, Wolfgang Wuttke. Effects of long-term treatment with 8-prenylnaringenin and oral estradiol on the GH-IGF-1 axis and lipid metabolism in rats. The Journal of endocrinology. 2008 Aug; 198(2):395-401. doi: 10.1677/joe-08-0127. [PMID: 18499805]
Stephan Sehmisch, Frauke Hammer, Julie Christoffel, Dana Seidlova-Wuttke, Mohammad Tezval, Wolfgang Wuttke, Klaus Michael Stuermer, Ewa Klara Stuermer. Comparison of the phytohormones genistein, resveratrol and 8-prenylnaringenin as agents for preventing osteoporosis. Planta medica. 2008 Jun; 74(8):794-801. doi: 10.1055/s-2008-1074550. [PMID: 18537073]
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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]
Sam Possemiers, Selin Bolca, Ellen Eeckhaut, Herman Depypere, Willy Verstraete. Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community. FEMS microbiology ecology. 2007 Aug; 61(2):372-83. doi: 10.1111/j.1574-6941.2007.00330.x. [PMID: 17506823]
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Casey S Philbin, Steven J Schwartz. Resolution of diastereomeric flavonoid (1S)-(-)-camphanic acid esters via reversed-phase HPLC. Phytochemistry. 2007 Apr; 68(8):1206-11. doi: 10.1016/j.phytochem.2007.01.022. [PMID: 17363016]
M Rad, M Hümpel, O Schaefer, R C Schoemaker, W-D Schleuning, A F Cohen, J Burggraaf. Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women. British journal of clinical pharmacology. 2006 Sep; 62(3):288-96. doi: 10.1111/j.1365-2125.2006.02656.x. [PMID: 16934044]
Arne Heyerick, Stefaan Vervarcke, Herman Depypere, Marc Bracke, Denis De Keukeleire. A first prospective, randomized, double-blind, placebo-controlled study on the use of a standardized hop extract to alleviate menopausal discomforts. Maturitas. 2006 May; 54(2):164-75. doi: 10.1016/j.maturitas.2005.10.005. [PMID: 16321485]
Ah-Reum Han, You-Jin Kang, Tri Windono, Sang Kook Lee, Eun-Kyoung Seo. Prenylated flavonoids from the heartwood of Artocarpus communis with inhibitory activity on lipopolysaccharide-induced nitric oxide production. Journal of natural products. 2006 Apr; 69(4):719-21. doi: 10.1021/np0600346. [PMID: 16643064]
J Christoffel, G Rimoldi, W Wuttke. Effects of 8-prenylnaringenin on the hypothalamo-pituitary-uterine axis in rats after 3-month treatment. The Journal of endocrinology. 2006 Mar; 188(3):397-405. doi: 10.1677/joe.1.06384. [PMID: 16522720]
Michael Hümpel, Päivi Isaksson, Olaf Schaefer, Ulrike Kaufmann, Paolo Ciana, Adriana Maggi, Wolf-Dieter Schleuning. Tissue specificity of 8-prenylnaringenin: protection from ovariectomy induced bone loss with minimal trophic effects on the uterus. The Journal of steroid biochemistry and molecular biology. 2005 Nov; 97(3):299-305. doi: 10.1016/j.jsbmb.2005.05.009. [PMID: 16153822]
Katharina E Effenberger, Steven A Johnsen, David G Monroe, Thomas C Spelsberg, Johannes J Westendorf. Regulation of osteoblastic phenotype and gene expression by hop-derived phytoestrogens. The Journal of steroid biochemistry and molecular biology. 2005 Sep; 96(5):387-99. doi: 10.1016/j.jsbmb.2005.04.038. [PMID: 16019205]
Sam Possemiers, Arne Heyerick, Veerle Robbens, Denis De Keukeleire, Willy Verstraete. Activation of proestrogens from hops (Humulus lupulus L.) by intestinal microbiota; conversion of isoxanthohumol into 8-prenylnaringenin. Journal of agricultural and food chemistry. 2005 Aug; 53(16):6281-8. doi: 10.1021/jf0509714. [PMID: 16076107]
Birgit M Dietz, Young-Hwa Kang, Guowen Liu, Aimee L Eggler, Ping Yao, Lucas R Chadwick, Guido F Pauli, Norman R Farnsworth, Andrew D Mesecar, Richard B van Breemen, Judy L Bolton. Xanthohumol isolated from Humulus lupulus Inhibits menadione-induced DNA damage through induction of quinone reductase. Chemical research in toxicology. 2005 Aug; 18(8):1296-305. doi: 10.1021/tx050058x. [PMID: 16097803]
Olaf Schaefer, Rolf Bohlmann, Wolf-Dieter Schleuning, Kai Schulze-Forster, Michael Hümpel. Development of a radioimmunoassay for the quantitative determination of 8-prenylnaringenin in biological matrices. Journal of agricultural and food chemistry. 2005 Apr; 53(8):2881-9. doi: 10.1021/jf047897u. [PMID: 15826034]
Dejan Nikolic, Yongmei Li, Lucas R Chadwick, Guido F Pauli, Richard B van Breemen. Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes. Journal of mass spectrometry : JMS. 2005 Mar; 40(3):289-99. doi: 10.1002/jms.753. [PMID: 15712367]
Oliver Zierau, Juliane Hamann, Sandra Tischer, Pia Schwab, Peter Metz, Günter Vollmer, Herwig O Gutzeit, Stefan Scholz. Naringenin-type flavonoids show different estrogenic effects in mammalian and teleost test systems. Biochemical and biophysical research communications. 2005 Jan; 326(4):909-16. doi: 10.1016/j.bbrc.2004.11.124. [PMID: 15607756]
Oliver Zierau, Stefanie Hauswald, Pia Schwab, Peter Metz, Günter Vollmer. Two major metabolites of 8-prenylnaringenin are estrogenic in vitro. The Journal of steroid biochemistry and molecular biology. 2004 Sep; 92(1-2):107-10. doi: 10.1016/j.jsbmb.2004.06.001. [PMID: 15544936]
Oliver Zierau, Renate-B Geis, Sandra Tischer, Pia Schwab, Peter Metz, Günter Vollmer. Uterine effects of the phytoestrogen 6-(1,1-dimethylallyl)naringenin in rats. Planta medica. 2004 Jul; 70(7):590-3. doi: 10.1055/s-2004-827178. [PMID: 15254850]
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Michael S Pepper, Susan J Hazel, Michael Hümpel, Wolf-Dieter Schleuning. 8-prenylnaringenin, a novel phytoestrogen, inhibits angiogenesis in vitro and in vivo. Journal of cellular physiology. 2004 Apr; 199(1):98-107. doi: 10.1002/jcp.10460. [PMID: 14978739]
Dejan Nikolic, Yongmei Li, Lucas R Chadwick, Simonida Grubjesic, Pia Schwab, Peter Metz, Richard B van Breemen. Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals. 2004 Feb; 32(2):272-9. doi: 10.1124/dmd.32.2.272. [PMID: 14744951]
Kazuhiko Nakahara, Molay Kumar Roy, Hiroshi Ono, Ikuko Maeda, Mayumi Ohnishi-Kameyama, Mitsuru Yoshida, Gassinee Trakoontivakorn. Prenylated flavanones isolated from flowers of Azadirachta indica (the neem tree) as antimutagenic constituents against heterocyclic amines. Journal of agricultural and food chemistry. 2003 Oct; 51(22):6456-60. doi: 10.1021/jf034666z. [PMID: 14558762]
Oliver Zierau, Colm Morrissey, R William G Watson, Pia Schwab, Susanne Kolba, Peter Metz, Günter Vollmer. Antiandrogenic activity of the phytoestrogens naringenin, 6-(1,1-dimethylallyl)naringenin and 8-prenylnaringenin. Planta medica. 2003 Sep; 69(9):856-8. doi: 10.1055/s-2003-43222. [PMID: 14598215]
Toshio Fukai, Makiko Yonekawa, Ai-Jun Hou, Taro Nomura, Han-Dong Sun, Jun Uno. Antifungal agents from the roots of Cudrania cochinchinensis against Candida, Cryptococcus, and Aspergillus species. Journal of natural products. 2003 Aug; 66(8):1118-20. doi: 10.1021/np030024u. [PMID: 12932139]
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