4-hydroxy-8-methyl-3,5,7,8-tetrakis(3-methylbutyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione (BioDeep_00001006084)
代谢物信息卡片
4-hydroxy-8-methyl-3,5,7,8-tetrakis(3-methylbutyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
化学式: C34H58O4 (530.4335)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC(C)CCC1CC2(C(=C(C(=O)C(C2=O)(C1(C)CCC(C)C)C(=O)C(C)C)CCC(C)C)O)CCC(C)C
InChI: InChI=1S/C34H58O4/c1-21(2)12-14-26-20-33(19-17-24(7)8)29(36)27(15-13-22(3)4)30(37)34(31(33)38,28(35)25(9)10)32(26,11)18-16-23(5)6/h21-26,36H,12-20H2,1-11H3
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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 |
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文献列表
- Aneliya Knauthe, Sonnhild Mittag, Laura Bloch, Kai Frederik Albring, Martin Schmidt, Oliver Werz, Otmar Huber. Hyperforin and Myrtucommulone Derivatives Act as Natural Modulators of Wnt/β-Catenin Signaling in HCT116 Colon Cancer Cells.
International journal of molecular sciences.
2022 Mar; 23(6):. doi:
10.3390/ijms23062984. [PMID: 35328403] - Anja Traeger, Susanna Voelker, Blerina Shkodra-Pula, Christian Kretzer, Stephanie Schubert, Michael Gottschaldt, Ulrich S Schubert, Oliver Werz. Improved Bioactivity of the Natural Product 5-Lipoxygenase Inhibitor Hyperforin by Encapsulation into Polymeric Nanoparticles.
Molecular pharmaceutics.
2020 03; 17(3):810-816. doi:
10.1021/acs.molpharmaceut.9b01051. [PMID: 31967843] - Catherine Zahner, Esther Kruttschnitt, Julia Uricher, Michael Lissy, Martin Hirsch, Simon Nicolussi, Stephan Krähenbühl, Jürgen Drewe. No Clinically Relevant Interactions of St. John's Wort Extract Ze 117 Low in Hyperforin With Cytochrome P450 Enzymes and P-glycoprotein.
Clinical pharmacology and therapeutics.
2019 08; 106(2):432-440. doi:
10.1002/cpt.1392. [PMID: 30739325] - Jeffry Adiwidjaja, Alan V Boddy, Andrew J McLachlan. Physiologically Based Pharmacokinetic Modelling of Hyperforin to Predict Drug Interactions with St John's Wort.
Clinical pharmacokinetics.
2019 07; 58(7):911-926. doi:
10.1007/s40262-019-00736-6. [PMID: 30675694] - Nelli Keksel, Hendrik Bussmann, Matthias Unger, Jürgen Drewe, Georg Boonen, Hanns Häberlein, Sebastian Franken. St John's wort extract influences membrane fluidity and composition of phosphatidylcholine and phosphatidylethanolamine in rat C6 glioblastoma cells.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2019 Feb; 54(?):66-76. doi:
10.1016/j.phymed.2018.06.013. [PMID: 30668384] - Simona Negreş, Corina Scutari, Floriana Elvira Ionică, Veaceslav Gonciar, Bruno Ştefan Velescu, Oana Cristina Şeremet, Anca Zanfirescu, Cristina Elena Zbârcea, Emil Ştefănescu, Emilia Ciobotaru, Cornel ChiriŢă. Influence of hyperforin on the morphology of internal organs and biochemical parameters, in experimental model in mice.
Romanian journal of morphology and embryology = Revue roumaine de morphologie et embryologie.
2016; 57(2 Suppl):663-673. doi:
. [PMID: 27833957] - Claudia Fracasso, Renzo Bagnati, Alice Passoni, Giovanna Guiso, Lavinia Cantoni, Antonella Riva, Paolo Morazzoni, Marco Gobbi. Brain Uptake of Tetrahydrohyperforin and Potential Metabolites after Repeated Dosing in Mice.
Journal of natural products.
2015 Aug; 78(8):2029-35. doi:
10.1021/acs.jnatprod.5b00302. [PMID: 26287496] - Miriam S N Hohmann, Renato D R Cardoso, Victor Fattori, Nilton S Arakawa, José C Tomaz, Norberto P Lopes, Rubia Casagrande, Waldiceu A Verri. Hypericum perforatum Reduces Paracetamol-Induced Hepatotoxicity and Lethality in Mice by Modulating Inflammation and Oxidative Stress.
Phytotherapy research : PTR.
2015 Jul; 29(7):1097-101. doi:
10.1002/ptr.5350. [PMID: 25851311] - Viviana A Cavieres, Alexis González, Vanessa C Muñoz, Claudia P Yefi, Hianara A Bustamante, Rafael R Barraza, Cheril Tapia-Rojas, Carola Otth, María José Barrera, Carlos González, Gonzalo A Mardones, Nibaldo C Inestrosa, Patricia V Burgos. Tetrahydrohyperforin Inhibits the Proteolytic Processing of Amyloid Precursor Protein and Enhances Its Degradation by Atg5-Dependent Autophagy.
PloS one.
2015; 10(8):e0136313. doi:
10.1371/journal.pone.0136313. [PMID: 26308941] - Thomas S Sell, Thabet Belkacemi, Veit Flockerzi, Andreas Beck. Protonophore properties of hyperforin are essential for its pharmacological activity.
Scientific reports.
2014 Dec; 4(?):7500. doi:
10.1038/srep07500. [PMID: 25511254] - A Bouron, E Lorrain. [Cellular and molecular effects of the antidepressant hyperforin on brain cells: Review of the literature].
L'Encephale.
2014 Apr; 40(2):108-13. doi:
10.1016/j.encep.2013.03.004. [PMID: 23816060] - Daniel Jakobs, Anne Hage-Hülsmann, Lars Prenner, Christiane Kolb, Dieter Weiser, Hanns Häberlein. Downregulation of β1 -adrenergic receptors in rat C6 glioblastoma cells by hyperforin and hyperoside from St John's wort.
The Journal of pharmacy and pharmacology.
2013 Jun; 65(6):907-15. doi:
10.1111/jphp.12050. [PMID: 23647684] - Robert J Wolf, Ralf A Hilger, Jörg D Hoheisel, Jens Werner, Frank Holtrup. In vivo activity and pharmacokinetics of nemorosone on pancreatic cancer xenografts.
PloS one.
2013; 8(9):e74555. doi:
10.1371/journal.pone.0074555. [PMID: 24040280] - Aurora Valeri, Raffaele Capasso, Massimo Valoti, Federica Pessina. Effects of St John's wort and its active constituents, hypericin and hyperforin, on isolated rat urinary bladder.
The Journal of pharmacy and pharmacology.
2012 Dec; 64(12):1770-6. doi:
10.1111/j.2042-7158.2012.01556.x. [PMID: 23146040] - B A Carillo, E B Oliveira-Sales, M Andersen, S Tufik, D Hipolide, A A Santos, P J Tucci, C T Bergamaschi, R R Campos. Changes in GABAergic inputs in the paraventricular nucleus maintain sympathetic vasomotor tone in chronic heart failure.
Autonomic neuroscience : basic & clinical.
2012 Nov; 171(1-2):41-8. doi:
10.1016/j.autneu.2012.10.005. [PMID: 23146621] - Julien Gibon, Peng Tu, Alexandre Bouron. Store-depletion and hyperforin activate distinct types of Ca(2+)-conducting channels in cortical neurons.
Cell calcium.
2010 Jun; 47(6):538-43. doi:
10.1016/j.ceca.2010.05.003. [PMID: 20621761] - Peng Tu, Julien Gibon, Alexandre Bouron. The TRPC6 channel activator hyperforin induces the release of zinc and calcium from mitochondria.
Journal of neurochemistry.
2010 Jan; 112(1):204-13. doi:
10.1111/j.1471-4159.2009.06446.x. [PMID: 19845832] - Jerome Sarris, David J Kavanagh. Kava and St. John's Wort: current evidence for use in mood and anxiety disorders.
Journal of alternative and complementary medicine (New York, N.Y.).
2009 Aug; 15(8):827-36. doi:
10.1089/acm.2009.0066. [PMID: 19614563] - Anna Lundahl, Mikael Hedeland, Ulf Bondesson, Lars Knutson, Hans Lennernäs. The effect of St. John's wort on the pharmacokinetics, metabolism and biliary excretion of finasteride and its metabolites in healthy men.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2009 Mar; 36(4-5):433-43. doi:
10.1016/j.ejps.2008.11.009. [PMID: 19073252] - Xue-Ding Wang, Jia-Li Li, Qi-Biao Su, Su Guan, Jie Chen, Jun Du, Yu-Wen He, Jun Zeng, Jin-Xin Zhang, Xiao Chen, Min Huang, Shu-Feng Zhou. Impact of the haplotypes of the human pregnane X receptor gene on the basal and St John's wort-induced activity of cytochrome P450 3A4 enzyme.
British journal of clinical pharmacology.
2009 Feb; 67(2):255-61. doi:
10.1111/j.1365-2125.2008.03344.x. [PMID: 19173680] - Silke C Mueller, Jolanta Majcher-Peszynska, Ralf G Mundkowski, Bernhard Uehleke, Sebastian Klammt, Hartwig Sievers, Romanus Lehnfeld, Bruno Frank, Kerstin Thurow, Guenther Kundt, Bernd Drewelow. No clinically relevant CYP3A induction after St. John's wort with low hyperforin content in healthy volunteers.
European journal of clinical pharmacology.
2009 Jan; 65(1):81-7. doi:
10.1007/s00228-008-0554-y. [PMID: 18762932] - Ze-Ping Hu, Xiao-Xia Yang, Xiao Chen, Jie Cao, Eli Chan, Wei Duan, Min Huang, Xue-Qing Yu, Jing-Yuan Wen, Shu-Feng Zhou. A mechanistic study on altered pharmacokinetics of irinotecan by St. John's wort.
Current drug metabolism.
2007 Feb; 8(2):157-71. doi:
10.2174/138920007779815995. [PMID: 17305494] - Rajanikanth Madabushi, Bruno Frank, Bernd Drewelow, Hartmut Derendorf, Veronika Butterweck. Hyperforin in St. John's wort drug interactions.
European journal of clinical pharmacology.
2006 Mar; 62(3):225-33. doi:
10.1007/s00228-006-0096-0. [PMID: 16477470] - Claudia M Klier, Brigitte Schmid-Siegel, Miriam R Schäfer, Gerhard Lenz, Alois Saria, Amy Lee, Gerald Zernig. St. John's wort (Hypericum perforatum) and breastfeeding: plasma and breast milk concentrations of hyperforin for 5 mothers and 2 infants.
The Journal of clinical psychiatry.
2006 Feb; 67(2):305-9. doi:
10.4088/jcp.v67n0219. [PMID: 16566628] - Mario Wurglics, Manfred Schubert-Zsilavecz. Hypericum perforatum: a 'modern' herbal antidepressant: pharmacokinetics of active ingredients.
Clinical pharmacokinetics.
2006; 45(5):449-68. doi:
10.2165/00003088-200645050-00002. [PMID: 16640452] - Silke C Mueller, Jolanta Majcher-Peszynska, Bernhard Uehleke, Sebastian Klammt, Ralf G Mundkowski, Wolfram Miekisch, Hartwig Sievers, Steffen Bauer, Bruno Frank, Guenther Kundt, Bernd Drewelow. The extent of induction of CYP3A by St. John's wort varies among products and is linked to hyperforin dose.
European journal of clinical pharmacology.
2006 Jan; 62(1):29-36. doi:
10.1007/s00228-005-0061-3. [PMID: 16341856] - Eleni M Gioti, Dimitris C Skalkos, Yiannis C Fiamegos, Constantine D Stalikas. Single-drop liquid-phase microextraction for the determination of hypericin, pseudohypericin and hyperforin in biological fluids by high performance liquid chromatography.
Journal of chromatography. A.
2005 Nov; 1093(1-2):1-10. doi:
10.1016/j.chroma.2005.07.038. [PMID: 16233865] - Benedetto Vitiello, Richard I Shader, Corette B Parker, Louise Ritz, William Harlan, David J Greenblatt, Kishore M Gadde, K Ranga R Krishnan, Jonathan R T Davidson. Hyperforin plasma level as a marker of treatment adherence in the National Institutes of Health Hypericum Depression Trial.
Journal of clinical psychopharmacology.
2005 Jun; 25(3):243-9. doi:
10.1097/01.jcp.0000162801.72002.85. [PMID: 15876903] - Run Tian, Noriko Koyabu, Satoshi Morimoto, Yukihiro Shoyama, Hisakazu Ohtani, Yasufumi Sawada. Functional induction and de-induction of P-glycoprotein by St. John's wort and its ingredients in a human colon adenocarcinoma cell line.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Apr; 33(4):547-54. doi:
10.1124/dmd.104.002485. [PMID: 15640377] - Luigi Cervo, Tiziana Mennini, Marco Rozio, Charlotte Blanche Ekalle-Soppo, Alessandro Canetta, Silvia Burbassi, Giovanna Guiso, Lorenza Pirona, Antonella Riva, Paolo Morazzoni, Silvio Caccia, Marco Gobbi. Potential antidepressant properties of IDN 5491 (hyperforin-trimethoxybenzoate), a semisynthetic ester of hyperforin.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology.
2005 Mar; 15(2):211-8. doi:
10.1016/j.euroneuro.2004.07.004. [PMID: 15695067] - M Rozio, C Fracasso, A Riva, P Morazzoni, S Caccia. High-performance liquid chromatography measurement of hyperforin and its reduced derivatives in rodent plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2005 Feb; 816(1-2):21-7. doi:
10.1016/j.jchromb.2004.10.015. [PMID: 15664329] - Hans-Ulrich Schulz, Michael Schürer, Dagmar Bässler, Dieter Weiser. Investigation of pharmacokinetic data of hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin revealed from single and multiple oral dose studies with a hypericum extract containing tablet in healthy male volunteers.
Arzneimittel-Forschung.
2005; 55(10):561-8. doi:
10.1055/s-0031-1296905. [PMID: 16294501] - Hans-Ulrich Schulz, Michael Schürer, Dagmar Bässler, Dieter Weiser. Investigation of the bioavailability of hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin following single and multiple oral dosing of a hypericum extract containing tablet.
Arzneimittel-Forschung.
2005; 55(1):15-22. doi:
10.1055/s-0031-1296820. [PMID: 15727160] - Klaus-Dieter Riedel, Karin Rieger, Meret Martin-Facklam, Gerd Mikus, Walter E Haefeli, Jürgen Burhenne. Simultaneous determination of hypericin and hyperforin in human plasma with liquid chromatography-tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2004 Dec; 813(1-2):27-33. doi:
10.1016/j.jchromb.2004.09.061. [PMID: 15556512] - Luisella Verotta, Erminio Lovaglio, Olov Sterner, Giovanni Appendino, Ezio Bombardelli. Modulation of chemoselectivity by protein additives. Remarkable effects in the oxidation of hyperforin.
The Journal of organic chemistry.
2004 Nov; 69(23):7869-74. doi:
10.1021/jo048857s. [PMID: 15527263] - C C Weber, S Kressmann, G Fricker, W E Müller. Modulation of P-glycoprotein function by St John's wort extract and its major constituents.
Pharmacopsychiatry.
2004 Nov; 37(6):292-8. doi:
10.1055/s-2004-832686. [PMID: 15551196] - Meret Martin-Facklam, Karin Rieger, Klaus-Dieter Riedel, Jürgen Burhenne, Ingeborg Walter-Sack, Walter E Haefeli. Undeclared exposure to St. John's Wort in hospitalized patients.
British journal of clinical pharmacology.
2004 Oct; 58(4):437-41. doi:
10.1111/j.1365-2125.2004.02169.x. [PMID: 15373938] - Ingrid Mai, Steffen Bauer, Elke S Perloff, Andreas Johne, Bernhard Uehleke, Bruno Frank, Klemens Budde, Ivar Roots. Hyperforin content determines the magnitude of the St John's wort-cyclosporine drug interaction.
Clinical pharmacology and therapeutics.
2004 Oct; 76(4):330-40. doi:
10.1016/j.clpt.2004.07.004. [PMID: 15470332] - Marco Gobbi, Manuela Moia, Marcella Funicello, Antonella Riva, Paolo Morazzoni, Tiziana Mennini. In vitro effects of the dicyclohexylammonium salt of hyperforin on interleukin-6 release in different experimental models.
Planta medica.
2004 Jul; 70(7):680-2. doi:
10.1055/s-2004-827194. [PMID: 15303261] - Bernard J Komoroski, Shimin Zhang, Hongbo Cai, J Matthew Hutzler, Reginald Frye, Timothy S Tracy, Stephen C Strom, Thomas Lehmann, Catharina Y W Ang, Yan Yan Cui, Raman Venkataramanan. Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures.
Drug metabolism and disposition: the biological fate of chemicals.
2004 May; 32(5):512-8. doi:
10.1124/dmd.32.5.512. [PMID: 15100173] - A T Hübner. Treatment with Hypericum perforatum L. does not trigger decreased resistance in Staphylococcus aureus against antibiotics and hyperforin.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2003 Mar; 10(2-3):206-8. doi:
10.1078/094471103321659951. [PMID: 12725578] - Luigi Cervo, Marco Rozio, C B Ekalle-Soppo, Giovanna Guiso, Paolo Morazzoni, Silvio Caccia. Role of hyperforin in the antidepressant-like activity of Hypericum perforatum extracts.
Psychopharmacology.
2002 Dec; 164(4):423-8. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Nov; 780(1):129-35. doi:
10.1016/s1570-0232(02)00439-7. [PMID: 12383488] - R Pirker, C W Huck, G K Bonn. Simultaneous determination of hypericin and hyperforin in human plasma and serum using liquid-liquid extraction, high-performance liquid chromatography and liquid chromatography-tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Sep; 777(1-2):147-53. doi:
10.1016/s1570-0232(02)00080-6. [PMID: 12270208] - Marie-Luise Buchholzer, Claudia Dvorak, Shyam S Chatterjee, Jochen Klein. Dual modulation of striatal acetylcholine release by hyperforin, a constituent of St. John's wort.
The Journal of pharmacology and experimental therapeutics.
2002 May; 301(2):714-9. doi:
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Journal of chromatography. B, Biomedical sciences and applications.
2001 Dec; 765(1):29-35. doi:
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Pharmacopsychiatry.
2001 Jul; 34 Suppl 1(?):S45-8. doi:
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Pharmacopsychiatry.
2001 Jul; 34 Suppl 1(?):S127-33. doi:
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Pharmacopsychiatry.
2001 Jul; 34 Suppl 1(?):S29-37. doi:
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2000 Dec; 7(6):455-62. doi:
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Journal of chromatography. B, Biomedical sciences and applications.
1999 Dec; 735(2):285-8. doi:
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Biological psychiatry.
1999 Aug; 46(4):581-4. doi:
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Pharmacopsychiatry.
1998 Jun; 31 Suppl 1(?):36-43. doi:
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Pharmacopsychiatry.
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