Hyperforin (BioDeep_00000000640)

 

Secondary id: BioDeep_00000288205

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-, (1R,5S,6R,7S)-

化学式: C35H52O4 (536.3865392)
中文名称: 贯叶金丝桃素 二环己基铵盐, 贯叶金丝桃素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.45%

分子结构信息

SMILES: CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(CC=C(C)C)C(=O)C(=C([C@@]1(C(=O)C(C)C)C2=O)O)CC=C(C)C)C
InChI: InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3

描述信息

Hyperforin is a cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. Johns Wort, Hypericum perforatum. It has a role as a GABA reuptake inhibitor, a plant metabolite, an anti-inflammatory agent, an antidepressant, an antibacterial agent, an antineoplastic agent and an apoptosis inducer. It is a cyclic terpene ketone, a sesquarterpenoid and a carbobicyclic compound.
Hyperforin is a phytochemical generated by the plants of the Hypericum family. One of the most important members of this family, due to its medical properties, is Hypericum perforatum, also known as St Johns wort.
Hyperforin is a natural product found in Hypericum linarioides, Hypericum rumeliacum, and other organisms with data available.
Hyperforin is found in alcoholic beverages. Hyperforin is a constituent of Hypericum perforatum (St Johns Wort) Hyperforin is a phytochemical produced by some of the members of the plant genus Hypericum, notably Hypericum perforatum (St Johns wort). The structure of hyperforin was elucidated by a research group from the Shemyakin Institute of Bio-organic Chemistry (USSR Academy of Sciences in Moscow) and published in 1975. Hyperforin is a prenylated phloroglucinol derivative. Total synthesis of hyperforin has not yet been accomplished, despite attempts by several research groups
Constituent of Hypericum perforatum (St Johns Wort)

同义名列表

24 个代谢物同义名

Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-, (1R,5S,6R,7S)-; BICYCLO(3.3.1)NON-3-ENE-2,9-DIONE, 4-HYDROXY-6-METHYL-1,3,7-TRIS(3-METHYL-2-BUTEN-1-YL)-5-(2-METHYL-1-OXOPROPYL)-6-(4-METHYL-3-PENTEN-1-YL)-, (1R,5S,6R,7S)-; Bicyclo(3.3.1)(1,4)benzodiazepin-5-one, 4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl)-, (1R,5S,6R,7S)-; Bicyclo[3.3.1]non-3-ene-2,9-dione,4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-,(1R,5S,6R,7S)-; (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione; (1R,5S,6R,7S)-4-hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione; 5-hydroxy-6R-methyl-1R,3,7S-tris(3-methyl-2-butenyl)-5S-(2-methyl-1-oxopropyl)-6R-(4-methyl-3-pentenyl)-bicyclo[3.3.1]non-3-ene-2,9-dione; 4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione; 4-Hydroxy-6-methyl-1,3,7-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-pentenyl) bicyclo(3.3.1)non-3-ene-2,9-dione; HYPERFORIN (CONSTITUENT OF ST. JOHNS WORT) [DSC]; KGSZHKRKHXOAMG-HQKKAZOISA-N; IWBJJCOKGLUQIZ-HQKKAZOISA-N; Hyperforin, >=85\\% (HPLC); tetrahydrohyperforin; HYPERFORIN [WHO-DD]; octahydrohyperforin; HYPERFORIN [HSDB]; Spectrum5_002025; HYPERFORIN [MI]; (+)-Hyperforin; PDSP2_001346; hyperforine; hiperforina; Hyperforin



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

29 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

  • Myriam El Biali, Michael Wölfl-Duchek, Matthias Jackwerth, Severin Mairinger, Maria Weber, Karsten Bamminger, Stefan Poschner, Ivo Rausch, Natalie Schindler, Irene Hernández Lozano, Walter Jäger, Lukas Nics, Nicolas Tournier, Marcus Hacker, Markus Zeitlinger, Martin Bauer, Oliver Langer. St. John's wort extract with a high hyperforin content does not induce P-glycoprotein activity at the human blood-brain barrier. Clinical and translational science. 2024 May; 17(5):e13804. doi: 10.1111/cts.13804. [PMID: 38700454]
  • Vanessa Fabienne Abegg, Miljenko Valentin Panajatovic, Riccardo Vincenzo Mancuso, Julien Arthur Allard, Urs Duthaler, Alex Odermatt, Stephan Krähenbühl, Jamal Bouitbir. Mechanisms of hepatocellular toxicity associated with the components of St. John's Wort extract hypericin and hyperforin in HepG2 and HepaRG cells. Toxicology letters. 2024 Jan; 393(?):1-13. doi: 10.1016/j.toxlet.2024.01.008. [PMID: 38219807]
  • Alexandre Bouron. Cellular neurobiology of hyperforin. Phytotherapy research : PTR. 2023 Nov; ?(?):. doi: 10.1002/ptr.8063. [PMID: 37963759]
  • Anima M Schäfer, Marta A Rysz, Julia Schädeli, Michelle Hübscher, Haleh Khosravi, Michelle Fehr, Isabell Seibert, Olivier Potterat, Martin Smieško, Henriette E Meyer Zu Schwabedissen. St. John's wort formulations induce rat CYP3A23-3A1 independent of their hyperforin content. Molecular pharmacology. 2023 Oct; ?(?):. doi: 10.1124/molpharm.123.000725. [PMID: 37863663]
  • Moritz Winker, Antoine Chauveau, Martin Smieško, Olivier Potterat, Alexander Areesanan, Amy Zimmermann-Klemd, Carsten Gründemann. Immunological evaluation of herbal extracts commonly used for treatment of mental diseases during pregnancy. Scientific reports. 2023 Jun; 13(1):9630. doi: 10.1038/s41598-023-35952-5. [PMID: 37316493]
  • Antoine Chauveau, Andrea Treyer, Annelies Geirnaert, Lea Bircher, Angela Babst, Vanessa Fabienne Abegg, Ana Paula Simões-Wüst, Christophe Lacroix, Olivier Potterat, Matthias Hamburger. Intestinal permeability and gut microbiota interactions of pharmacologically active compounds in valerian and St. John's wort. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Apr; 162(?):114652. doi: 10.1016/j.biopha.2023.114652. [PMID: 37027987]
  • Aleksandra Brankiewicz, Sara Trzos, Magdalena Mrożek, Małgorzata Opydo, Elżbieta Szostak, Michał Dziurka, Monika Tuleja, Agnieszka Łoboda, Ewa Pocheć. Cytotoxic and Antioxidant Activity of Hypericum perforatum L. Extracts against Human Melanoma Cells from Different Stages of Cancer Progression, Cultured under Normoxia and Hypoxia. Molecules (Basel, Switzerland). 2023 Feb; 28(3):. doi: 10.3390/molecules28031509. [PMID: 36771178]
  • Xin-Xin Li, Yu Yan, Jia Zhang, Kang Ding, Cong-Yuan Xia, Xue-Ge Pan, Yan-Jing Shi, Jie-Kun Xu, Jun He, Wei-Ku Zhang. Hyperforin: A natural lead compound with multiple pharmacological activities. Phytochemistry. 2023 Feb; 206(?):113526. doi: 10.1016/j.phytochem.2022.113526. [PMID: 36442576]
  • Zheng Zhang, Chuan Yao, Min Li, Li-Chuang Wang, Wei Huang, Qing-Jie Chen. Prophylactic effects of hyperforin on anhedonia-like phenotype in chronic restrain stress model: A role of gut microbiota. Letters in applied microbiology. 2022 Nov; 75(5):1103-1110. doi: 10.1111/lam.13710. [PMID: 35348232]
  • Song Wu, Ana Luisa Malaco Morotti, Shanshan Wang, Ya Wang, Xiaoyan Xu, Jianghua Chen, Guodong Wang, Evangelos C Tatsis. Convergent gene clusters underpin hyperforin biosynthesis in St John's wort. The New phytologist. 2022 07; 235(2):646-661. doi: 10.1111/nph.18138. [PMID: 35377483]
  • Esra Saçıcı, Erdem Yesilada. Development of new and validated HPTLC methods for the qualitative and quantitative analysis of hyperforin, hypericin and hyperoside contents in Hypericum species. Phytochemical analysis : PCA. 2022 Apr; 33(3):355-364. doi: 10.1002/pca.3093. [PMID: 34734668]
  • 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]
  • Suzhen Chen, Xiaoxiao Liu, Chao Peng, Chang Tan, Honglin Sun, He Liu, Yao Zhang, Ping Wu, Can Cui, Chuchu Liu, Di Yang, Zhiqiang Li, Junxi Lu, Jian Guan, Xisong Ke, Renxiao Wang, Xiaohai Bo, Xiaojun Xu, Junfeng Han, Junli Liu. The phytochemical hyperforin triggers thermogenesis in adipose tissue via a Dlat-AMPK signaling axis to curb obesity. Cell metabolism. 2021 03; 33(3):565-580.e7. doi: 10.1016/j.cmet.2021.02.007. [PMID: 33657393]
  • Noriko Shinjyo, Hideyuki Nakayama, Li Li, Kanji Ishimaru, Kenji Hikosaka, Noriyuki Suzuki, Hiroki Yoshida, Kazumi Norose. Hypericum perforatum extract and hyperforin inhibit the growth of neurotropic parasite Toxoplasma gondii and infection-induced inflammatory responses of glial cells in vitro. Journal of ethnopharmacology. 2021 Mar; 267(?):113525. doi: 10.1016/j.jep.2020.113525. [PMID: 33129946]
  • Katerina Makarova, Joanna J Sajkowska-Kozielewicz, Katarzyna Zawada, Ewa Olchowik-Grabarek, Michał Aleksander Ciach, Krzysztof Gogolewski, Natalia Dobros, Paulina Ciechowicz, Hélène Freichels, Anna Gambin. Harvest time affects antioxidant capacity, total polyphenol and flavonoid content of Polish St John's wort's (Hypericum perforatum L.) flowers. Scientific reports. 2021 02; 11(1):3989. doi: 10.1038/s41598-021-83409-4. [PMID: 33597594]
  • Michela Novelli, Pellegrino Masiello, Pascale Beffy, Marta Menegazzi. Protective Role of St. John's Wort and Its Components Hyperforin and Hypericin against Diabetes through Inhibition of Inflammatory Signaling: Evidence from In Vitro and In Vivo Studies. International journal of molecular sciences. 2020 Oct; 21(21):. doi: 10.3390/ijms21218108. [PMID: 33143088]
  • Paride Rizzo, Lothar Altschmied, Beena M Ravindran, Twan Rutten, John C D'Auria. The Biochemical and Genetic Basis for the Biosynthesis of Bioactive Compounds in Hypericum Perforatum L., One of the Largest Medicinal Crops in Europe. Genes. 2020 10; 11(10):. doi: 10.3390/genes11101210. [PMID: 33081197]
  • Chia-Hung Kuo, Yi-Chin Chou, Kuo-Chun Liao, Chwen-Jen Shieh, Tzu-Shing Deng. Optimization of Light Intensity, Temperature, and Nutrients to Enhance the Bioactive Content of Hyperforin and Rutin in St. John's Wort. Molecules (Basel, Switzerland). 2020 Sep; 25(18):. doi: 10.3390/molecules25184256. [PMID: 32948004]
  • 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]
  • Ilkay Erdogan Orhan, F Sezer Senol Deniz, Steinar Traedal-Henden, José P Cerón-Carrasco, Helena den Haan, Jorge Peña-García, Horacio Pérez-Sánchez, Esra Emerce, Krystyna Skalicka-Wozniak. Profiling Auspicious Butyrylcholinesterase Inhibitory Activity of Two Herbal Molecules: Hyperforin and Hyuganin C. Chemistry & biodiversity. 2019 May; 16(5):e1900017. doi: 10.1002/cbdv.201900017. [PMID: 30891904]
  • 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]
  • Haoran Wang, Bing Shao, Hongyan Yu, Feibo Xu, Peiyan Wang, Kaiyuan Yu, Yanfei Han, Miao Song, Yanfei Li, Zheng Cao. Neuroprotective role of hyperforin on aluminum maltolate-induced oxidative damage and apoptosis in PC12 cells and SH-SY5Y cells. Chemico-biological interactions. 2019 Feb; 299(?):15-26. doi: 10.1016/j.cbi.2018.11.016. [PMID: 30481499]
  • Sigrun Chrubasik-Hausmann, Julia Vlachojannis, Andrew J McLachlan. Understanding drug interactions with St John's wort (Hypericum perforatum L.): impact of hyperforin content. The Journal of pharmacy and pharmacology. 2019 Jan; 71(1):129-138. doi: 10.1111/jphp.12858. [PMID: 29411879]
  • Michela Novelli, Pascale Beffy, Alex Gregorelli, Svetlana Porozov, Fabrizio Mascia, Chiara Vantaggiato, Pellegrino Masiello, Marta Menegazzi. Persistence of STAT-1 inhibition and induction of cytokine resistance in pancreatic β cells treated with St John's wort and its component hyperforin. The Journal of pharmacy and pharmacology. 2019 Jan; 71(1):93-103. doi: 10.1111/jphp.12823. [PMID: 28990659]
  • Haroon Khan, Kannan R R Rengasamy, Aini Pervaiz, Seyed Mohammad Nabavi, Atanas G Atanasov, Mohammad A Kamal. Plant-derived mPGES-1 inhibitors or suppressors: A new emerging trend in the search for small molecules to combat inflammation. European journal of medicinal chemistry. 2018 Jun; 153(?):2-28. doi: 10.1016/j.ejmech.2017.12.059. [PMID: 29329790]
  • Sławomir Dresler, Jozef Kováčik, Maciej Strzemski, Ireneusz Sowa, Magdalena Wójciak-Kosior. Methodological aspects of biologically active compounds quantification in the genus Hypericum. Journal of pharmaceutical and biomedical analysis. 2018 Jun; 155(?):82-90. doi: 10.1016/j.jpba.2018.03.048. [PMID: 29621655]
  • Paul Haas, Mariam Gaid, Ajmal Zarinwall, Ludger Beerhues, Stephan Scholl. Downstream processing of hyperforin from Hypericum perforatum root cultures. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2018 May; 126(?):104-107. doi: 10.1016/j.ejpb.2017.06.026. [PMID: 28669795]
  • Mariam Gaid, Eline Biedermann, Jendrik Füller, Paul Haas, Sönke Behrends, Rainer Krull, Stephan Scholl, Ute Wittstock, Christel Müller-Goymann, Ludger Beerhues. Biotechnological production of hyperforin for pharmaceutical formulation. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2018 May; 126(?):10-26. doi: 10.1016/j.ejpb.2017.03.024. [PMID: 28377273]
  • Li Ma, Xia Pan, Fang Zhou, Kang Liu, Long Wang. Hyperforin protects against acute cerebral ischemic injury through inhibition of interleukin-17A-mediated microglial activation. Brain research. 2018 Jan; 1678(?):254-261. doi: 10.1016/j.brainres.2017.08.023. [PMID: 28870826]
  • Tomás Herraiz, Hugo Guillén. Monoamine Oxidase-A Inhibition and Associated Antioxidant Activity in Plant Extracts with Potential Antidepressant Actions. BioMed research international. 2018; 2018(?):4810394. doi: 10.1155/2018/4810394. [PMID: 29568754]
  • Samaneh Soleymani, Roodabeh Bahramsoltani, Roja Rahimi, Mohammad Abdollahi. Clinical risks of St John's Wort (Hypericum perforatum) co-administration. Expert opinion on drug metabolism & toxicology. 2017 Oct; 13(10):1047-1062. doi: 10.1080/17425255.2017.1378342. [PMID: 28885074]
  • Silvia Lazzara, Marcello Militello, Alessandra Carrubba, Edoardo Napoli, Sergio Saia. Arbuscular mycorrhizal fungi altered the hypericin, pseudohypericin, and hyperforin content in flowers of Hypericum perforatum grown under contrasting P availability in a highly organic substrate. Mycorrhiza. 2017 May; 27(4):345-354. doi: 10.1007/s00572-016-0756-6. [PMID: 27999964]
  • Qin Xiang Ng, Nandini Venkatanarayanan, Collin Yih Xian Ho. Clinical use of Hypericum perforatum (St John's wort) in depression: A meta-analysis. Journal of affective disorders. 2017 Mar; 210(?):211-221. doi: 10.1016/j.jad.2016.12.048. [PMID: 28064110]
  • Michela Novelli, Marta Menegazzi, Pascale Beffy, Svetlana Porozov, Alex Gregorelli, Daniela Giacopelli, Vincenzo De Tata, Pellegrino Masiello. St. John's wort extract and hyperforin inhibit multiple phosphorylation steps of cytokine signaling and prevent inflammatory and apoptotic gene induction in pancreatic β cells. The international journal of biochemistry & cell biology. 2016 12; 81(Pt A):92-104. doi: 10.1016/j.biocel.2016.10.017. [PMID: 27780755]
  • Jiancheng Zhang, Chengye Yao, Jiayi Chen, Yujing Zhang, Shiying Yuan, Yun Lin. Hyperforin promotes post-stroke functional recovery through interleukin (IL)-17A-mediated angiogenesis. Brain research. 2016 09; 1646(?):504-513. doi: 10.1016/j.brainres.2016.06.025. [PMID: 27328426]
  • Yan-Na Geng, Yi-Jun Wu, Wen-Xin Zhang. [Effect of hyperforin on learning and memory abilities and Aβ₁₋₄₂, βAPP and BACE1 protein expressions in hippocampus of Alzheimer's disease model mice]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2016 Aug; 41(15):2877-2882. doi: 10.4268/cjcmm20161522. [PMID: 28914032]
  • Wan Gao, Wei-Zhen Hou, Jun Zhao, Fang Xu, Li Li, Fang Xu, Hua Sun, Jian-Guo Xing, Ying Peng, Xiao-Liang Wang, Teng-Fei Ji, Zheng-Yi Gu. Polycyclic Polyprenylated Acylphloroglucinol Congeners from Hypericum scabrum. Journal of natural products. 2016 06; 79(6):1538-47. doi: 10.1021/acs.jnatprod.5b01063. [PMID: 27280968]
  • Serge A T Fobofou, Katrin Franke, Andrea Porzel, Wolfgang Brandt, Ludger A Wessjohann. Tricyclic Acylphloroglucinols from Hypericum lanceolatum and Regioselective Synthesis of Selancins A and B. Journal of natural products. 2016 Apr; 79(4):743-53. doi: 10.1021/acs.jnatprod.5b00673. [PMID: 26950610]
  • 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]
  • 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]
  • Sara M Silva, Ana Martinho, Ivo Moreno, Samuel Silvestre, Luiza Breitenfeld Granadeiro, Gilberto Alves, Ana Paula Duarte, Fernanda Domingues, Eugenia Gallardo. Effects of Hypericum perforatum extract and its main bioactive compounds on the cytotoxicity and expression of CYP1A2 and CYP2D6 in hepatic cells. Life sciences. 2016 Jan; 144(?):30-6. doi: 10.1016/j.lfs.2015.11.004. [PMID: 26612349]
  • Sylvain Chauvet, Alexandre Barras, Rabah Boukherroub, Alexandre Bouron. Lipid nanocapsules containing the non-ionic surfactant Solutol HS15 inhibit the transport of calcium through hyperforin-activated channels in neuronal cells. Neuropharmacology. 2015 Dec; 99(?):726-34. doi: 10.1016/j.neuropharm.2015.08.043. [PMID: 26341818]
  • 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]
  • Xing-Wei Yang, Ming-Ming Li, Xia Liu, Daneel Ferreira, Yuanqing Ding, Jing-Jing Zhang, Yang Liao, Hong-Bo Qin, Gang Xu. Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from Hypericum henryi. Journal of natural products. 2015 Apr; 78(4):885-95. doi: 10.1021/acs.jnatprod.5b00057. [PMID: 25871261]
  • Kristina Friedland, Christian Harteneck. Hyperforin: To Be or Not to Be an Activator of TRPC(6). Reviews of physiology, biochemistry and pharmacology. 2015; 169(?):1-24. doi: 10.1007/112_2015_25. [PMID: 26384487]
  • 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]
  • Katie M Vance, David M Ribnicky, Gerlinda E Hermann, Richard C Rogers. St. John's Wort enhances the synaptic activity of the nucleus of the solitary tract. Nutrition (Burbank, Los Angeles County, Calif.). 2014 Jul; 30(7-8 Suppl):S37-42. doi: 10.1016/j.nut.2014.02.008. [PMID: 24985104]
  • Emilio Russo, Francesca Scicchitano, Benjamin J Whalley, Carmela Mazzitello, Miriam Ciriaco, Stefania Esposito, Marinella Patanè, Roy Upton, Michela Pugliese, Serafina Chimirri, Maria Mammì, Caterina Palleria, Giovambattista De Sarro. Hypericum perforatum: pharmacokinetic, mechanism of action, tolerability, and clinical drug-drug interactions. Phytotherapy research : PTR. 2014 May; 28(5):643-55. doi: 10.1002/ptr.5050. [PMID: 23897801]
  • 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]
  • M Nazıroğlu, B Çiğ, C Özgül. Modulation of oxidative stress and Ca(2+) mobilization through TRPM2 channels in rat dorsal root ganglion neuron by Hypericum perforatum. Neuroscience. 2014 Mar; 263(?):27-35. doi: 10.1016/j.neuroscience.2014.01.006. [PMID: 24434769]
  • S F Haag, K Tscherch, S Arndt, A Kleemann, I Gersonde, J Lademann, S Rohn, M C Meinke. Enhancement of skin radical scavenging activity and stratum corneum lipids after the application of a hyperforin-rich cream. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2014 Feb; 86(2):227-33. doi: 10.1016/j.ejpb.2013.06.016. [PMID: 23811220]
  • Michela Novelli, Pascale Beffy, Marta Menegazzi, Vincenzo De Tata, Luisa Martino, Anna Sgarbossa, Svetlana Porozov, Anna Pippa, Matilde Masini, Piero Marchetti, Pellegrino Masiello. St. John's wort extract and hyperforin protect rat and human pancreatic islets against cytokine toxicity. Acta diabetologica. 2014 Feb; 51(1):113-21. doi: 10.1007/s00592-013-0518-2. [PMID: 24121871]
  • Nicoletta Galeotti, Anna Maidecchi, Luisa Mattoli, Michela Burico, Carla Ghelardini. St. John's Wort seed and feverfew flower extracts relieve painful diabetic neuropathy in a rat model of diabetes. Fitoterapia. 2014 Jan; 92(?):23-33. doi: 10.1016/j.fitote.2013.10.003. [PMID: 24125916]
  • Kimberly D P Hammer, Diane F Birt. Evidence for contributions of interactions of constituents to the anti-inflammatory activity of Hypericum perforatum. Critical reviews in food science and nutrition. 2014; 54(6):781-9. doi: 10.1080/10408398.2011.607519. [PMID: 24345048]
  • Anja Brenn, Markus Grube, Gabriele Jedlitschky, Andrea Fischer, Barbara Strohmeier, Martin Eiden, Markus Keller, Martin H Groschup, Silke Vogelgesang. St. John's Wort reduces beta-amyloid accumulation in a double transgenic Alzheimer's disease mouse model-role of P-glycoprotein. Brain pathology (Zurich, Switzerland). 2014 Jan; 24(1):18-24. doi: 10.1111/bpa.12069. [PMID: 23701205]
  • Jacqueline Hofrichter, Markus Krohn, Toni Schumacher, Cathleen Lange, Björn Feistel, Bernd Walbroel, Hans-Jochen Heinze, Sara Crockett, Timothy F Sharbel, Jens Pahnke. Reduced Alzheimer's disease pathology by St. John's Wort treatment is independent of hyperforin and facilitated by ABCC1 and microglia activation in mice. Current Alzheimer research. 2013 Dec; 10(10):1057-69. doi: 10.2174/15672050113106660171. [PMID: 24156265]
  • K Nakamura, K Aizawa, J Yamauchi, A Tanoue. Hyperforin inhibits cell proliferation and differentiation in mouse embryonic stem cells. Cell proliferation. 2013 Oct; 46(5):529-37. doi: 10.1111/cpr.12060. [PMID: 24033566]
  • Brigida Immacolata Pia Schiavone, Antonio Rosato, Muraglia Marilena, Simon Gibbons, Ezio Bombardelli, Luisella Verotta, Carlo Franchini, Filomena Corbo. Biological evaluation of hyperforin and its hydrogenated analogue on bacterial growth and biofilm production. Journal of natural products. 2013 Sep; 76(9):1819-23. doi: 10.1021/np400394c. [PMID: 23981190]
  • 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]
  • Julien Gibon, Jean-Christophe Deloulme, Tiphaine Chevallier, Elodie Ladevèze, Djoher Nora Abrous, Alexandre Bouron. The antidepressant hyperforin increases the phosphorylation of CREB and the expression of TrkB in a tissue-specific manner. The international journal of neuropsychopharmacology. 2013 Feb; 16(1):189-98. doi: 10.1017/s146114571100188x. [PMID: 22226089]
  • C Billard, F Merhi, B Bauvois. Mechanistic insights into the antileukemic activity of hyperforin. Current cancer drug targets. 2013 Jan; 13(1):1-10. doi: . [PMID: 22924417]
  • 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]
  • Kristina Leuner, Wei Li, Michelle D Amaral, Stephanie Rudolph, Gaston Calfa, Anita M Schuwald, Christian Harteneck, Takafumi Inoue, Lucas Pozzo-Miller. Hyperforin modulates dendritic spine morphology in hippocampal pyramidal neurons by activating Ca(2+) -permeable TRPC6 channels. Hippocampus. 2013 Jan; 23(1):40-52. doi: 10.1002/hipo.22052. [PMID: 22815087]
  • 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]
  • Trent Mortensen, Shujie Shen, Fenann Shen, Marie K Walsh, Ronald C Sims, Charles D Miller. Investigating the effectiveness of St John's wort herb as an antimicrobial agent against mycobacteria. Phytotherapy research : PTR. 2012 Sep; 26(9):1327-33. doi: 10.1002/ptr.3716. [PMID: 22294548]
  • Martina C Meinke, Sabine Schanzer, Stefan F Haag, Federica Casetti, Marcel L Müller, Ute Wölfle, Anke Kleemann, Juergen Lademann, Christoph M Schempp. In vivo photoprotective and anti-inflammatory effect of hyperforin is associated with high antioxidant activity in vitro and ex vivo. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2012 Jun; 81(2):346-50. doi: 10.1016/j.ejpb.2012.03.002. [PMID: 22430217]
  • Mohamed A Farag, Ludger A Wessjohann. Metabolome classification of commercial Hypericum perforatum (St. John's Wort) preparations via UPLC-qTOF-MS and chemometrics. Planta medica. 2012 Mar; 78(5):488-96. doi: 10.1055/s-0031-1298170. [PMID: 22271082]
  • Necdet Camas, Jolita Radusiene, Zydrunas Stanius, Omer Caliskan, Cuneyt Cirak. Secondary metabolites of Hypericum leptophyllum Hochst., an endemic Turkish species. TheScientificWorldJournal. 2012; 2012(?):501027. doi: 10.1100/2012/501027. [PMID: 22649295]
  • Julien Gibon, Pierre Richaud, Alexandre Bouron. Hyperforin changes the zinc-storage capacities of brain cells. Neuropharmacology. 2011 Dec; 61(8):1321-6. doi: 10.1016/j.neuropharm.2011.08.002. [PMID: 21854792]
  • Murhaf Zaher, Massoud Mirshahi, Yusuf Nuraliev, Mijgana Sharifova, Isabelle Bombarda, Jean-Pierre Marie, Christian Billard. The BH3-only protein Noxa is stimulated during apoptosis of chronic lymphocytic leukemia cells triggered by M2YN, a new plant-derived extract. International journal of oncology. 2011 Oct; 39(4):965-72. doi: 10.3892/ijo.2011.1121. [PMID: 21750864]
  • Satomi Onoue, Yoshiki Seto, Masanori Ochi, Ryo Inoue, Hideyuki Ito, Tsutomu Hatano, Shizuo Yamada. In vitro photochemical and phototoxicological characterization of major constituents in St. John's Wort (Hypericum perforatum) extracts. Phytochemistry. 2011 Oct; 72(14-15):1814-20. doi: 10.1016/j.phytochem.2011.06.011. [PMID: 21782201]
  • Melissa L Brechner, Louis D Albright, Leslie A Weston. Effects of UV-B on secondary metabolites of St. John's Wort (Hypericum perforatum L.) grown in controlled environments. Photochemistry and photobiology. 2011 May; 87(3):680-4. doi: 10.1111/j.1751-1097.2011.00904.x. [PMID: 21275996]
  • Jin-Yun Liu, Zhong Liu, Dong-Mei Wang, Man-Mei Li, Shao-Xiang Wang, Rui Wang, Jian-Ping Chen, Yi-Fei Wang, De-Po Yang. Induction of apoptosis in K562 cells by dicyclohexylammonium salt of hyperforin through a mitochondrial-related pathway. Chemico-biological interactions. 2011 Apr; 190(2-3):91-101. doi: 10.1016/j.cbi.2011.02.026. [PMID: 21376709]
  • Xueli Cao, Qiaoe Wang, Yan Li, Ge Bai, Hong Ren, Chunming Xu, Yoichiro Ito. Isolation and purification of series bioactive components from Hypericum perforatum L. by counter-current chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Mar; 879(7-8):480-8. doi: 10.1016/j.jchromb.2011.01.007. [PMID: 21306961]
  • F H Ebner, S Mariotto, E Darra, H Suzuki, E Cavalieri. Use of STAT1 inhibitors in the treatment of brain I/R injury and neurodegenerative diseases. Central nervous system agents in medicinal chemistry. 2011 Mar; 11(1):2-7. doi: 10.2174/187152411794961077. [PMID: 20812906]
  • Arif-ullah Khan, Anwarul-Hassan Gilani, Najeeb-ur-Rehman. Pharmacological studies on Hypericum perforatum fractions and constituents. Pharmaceutical biology. 2011 Jan; 49(1):46-56. doi: 10.3109/13880209.2010.494307. [PMID: 20738215]
  • Birgit Kraus, Horst Wolff, Erich F Elstner, Jörg Heilmann. Hyperforin is a modulator of inducible nitric oxide synthase and phagocytosis in microglia and macrophages. Naunyn-Schmiedeberg's archives of pharmacology. 2010 Jun; 381(6):541-53. doi: 10.1007/s00210-010-0512-y. [PMID: 20369228]
  • Cüneyt Cirak, Jolita Radusiene, Valdimaras Janulis, Liudas Ivanauskas. Secondary metabolites of Hypericum confertum and their possible chemotaxonomic significance. Natural product communications. 2010 Jun; 5(6):897-8. doi: ". [PMID: 20614818]
  • 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]
  • Adolf Nahrstedt, Veronika Butterweck. Lessons learned from herbal medicinal products: the example of St. John's Wort (perpendicular). Journal of natural products. 2010 May; 73(5):1015-21. doi: 10.1021/np1000329. [PMID: 20408551]
  • Marika Hoffmann, Jakob J Lopez, Carlo Pergola, Christian Feisst, Sven Pawelczik, Per-Johan Jakobsson, Bernd L Sorg, Clemens Glaubitz, Dieter Steinhilber, Oliver Werz. Hyperforin induces Ca(2+)-independent arachidonic acid release in human platelets by facilitating cytosolic phospholipase A(2) activation through select phospholipid interactions. Biochimica et biophysica acta. 2010 Apr; 1801(4):462-72. doi: 10.1016/j.bbalip.2009.12.007. [PMID: 20044029]
  • Marta Moya, M José Gómez-Lechón, José V Castell, Ramiro Jover. Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile. Chemico-biological interactions. 2010 Mar; 184(3):376-87. doi: 10.1016/j.cbi.2010.01.008. [PMID: 20079722]
  • Raffaella Filippini, Anna Piovan, Anna Borsarini, Rosy Caniato. Study of dynamic accumulation of secondary metabolites in three subspecies of Hypericum perforatum. Fitoterapia. 2010 Mar; 81(2):115-9. doi: 10.1016/j.fitote.2009.08.002. [PMID: 19686808]
  • 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]
  • Sean Kim, Joseph E Dinchuk, Monique N Anthony, Tami Orcutt, Mary E Zoeckler, Mary B Sauer, Kathleen W Mosure, Ragini Vuppugalla, James E Grace, Jean Simmermacher, Heidi A Dulac, Jennifer Pizzano, Michael Sinz. Evaluation of cynomolgus monkey pregnane X receptor, primary hepatocyte, and in vivo pharmacokinetic changes in predicting human CYP3A4 induction. Drug metabolism and disposition: the biological fate of chemicals. 2010 Jan; 38(1):16-24. doi: 10.1124/dmd.109.029637. [PMID: 19833845]
  • Silvio Caccia, Marco Gobbi. St. John's wort components and the brain: uptake, concentrations reached and the mechanisms underlying pharmacological effects. Current drug metabolism. 2009 Nov; 10(9):1055-65. doi: 10.2174/138920009790711878. [PMID: 20214594]
  • 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]
  • Mariane G Tadros, Mohamed R Mohamed, Amal M Youssef, Gilane M Sabry, Nagwa A Sabry, Amani E Khalifa. Proapoptotic and prepulse inhibition (PPI) disrupting effects of Hypericum perforatum in rats. Journal of ethnopharmacology. 2009 Apr; 122(3):561-6. doi: 10.1016/j.jep.2009.01.009. [PMID: 19171186]
  • 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]
  • Peng Tu, Christiane Kunert-Keil, Silke Lucke, Heinrich Brinkmeier, Alexandre Bouron. Diacylglycerol analogues activate second messenger-operated calcium channels exhibiting TRPC-like properties in cortical neurons. Journal of neurochemistry. 2009 Jan; 108(1):126-38. doi: 10.1111/j.1471-4159.2008.05752.x. [PMID: 19094061]
  • 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]
  • Cüneyt Cirak, Liudas Ivanauskas, Valdimaras Janulis, Jolita Radusiene. Chemical constituents of Hypericum adenotrichum Spach, an endemic Turkish species. Natural product research. 2009; 23(13):1189-95. doi: 10.1080/14786410802393209. [PMID: 19731137]
  • Andrea Sardella, Giovanni Lodi, Federica Demarosi, Marco Tarozzi, Lorenza Canegallo, Antonio Carrassi. Hypericum perforatum extract in burning mouth syndrome: a randomized placebo-controlled study. Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology. 2008 Aug; 37(7):395-401. doi: 10.1111/j.1600-0714.2008.00663.x. [PMID: 18331283]