cannabigerol (BioDeep_00000002558)

   

PANOMIX_OTCML-2023


代谢物信息卡片


1,3-Benzenediol, 2-(3,7-dimethyl-2,6-octadienyl)-5-pentyl-, (E)-

化学式: C21H32O2 (316.24021719999996)
中文名称: 大麻萜酚, 大麻萜酚
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 11.11%

分子结构信息

SMILES: CCCCCC1=CC(=C(C(=C1)O)CC=C(C)CCC=C(C)C)O
InChI: InChI=1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+

描述信息

A member of the class of resorcinols that is resorcinol which is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group at position 2 and by a pentyl group at position 5. It is a natural product found in Cannabis sativa and Helichrysum species.

同义名列表

2 个代谢物同义名

cannabigerol; 1,3-Benzenediol, 2-(3,7-dimethyl-2,6-octadienyl)-5-pentyl-, (E)-



数据库引用编号

11 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)

8 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

  • Wojciech Łuczaj, Izabela Dobrzyńska, Elżbieta Skrzydlewska. Differences in the phospholipid profile of melanocytes and melanoma cells irradiated with UVA and treated with cannabigerol and cannabidiol. Scientific reports. 2023 Sep; 13(1):16121. doi: 10.1038/s41598-023-43363-9. [PMID: 37752196]
  • Dylan T Marsh, Ayato Sugiyama, Yuta Imai, Ryuji Kato, Scott D Smid. The structurally diverse phytocannabinoids cannabichromene, cannabigerol and cannabinol significantly inhibit amyloid β-evoked neurotoxicity and changes in cell morphology in PC12 cells. Basic & clinical pharmacology & toxicology. 2023 Sep; ?(?):. doi: 10.1111/bcpt.13943. [PMID: 37697481]
  • Adam Wroński, Izabela Dobrzyńska, Szymon Sękowski, Wojciech Łuczaj, Ewa Olchowik-Grabarek, Elżbieta Skrzydlewska. Cannabidiol and Cannabigerol Modify the Composition and Physicochemical Properties of Keratinocyte Membranes Exposed to UVA. International journal of molecular sciences. 2023 Aug; 24(15):. doi: 10.3390/ijms241512424. [PMID: 37569799]
  • Man Shao, Xiao-Qin Yu, Li-Juan Huang, Huan Yao, Shu-Cai Li. [Determination of eight cannabinoids in foods with enhanced matrix removal-lipid adsorbent by ultra performance liquid chromatography-tandem mass spectrometry]. Se pu = Chinese journal of chromatography. 2023 May; 41(5):426-433. doi: 10.3724/sp.j.1123.2022.08010. [PMID: 37087608]
  • Yuting Wen, Zefeng Wang, Rui Zhang, Yuying Zhu, Guoqiang Lin, Ruixiang Li, Jiange Zhang. The antinociceptive activity and mechanism of action of cannabigerol. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Feb; 158(?):114163. doi: 10.1016/j.biopha.2022.114163. [PMID: 36916438]
  • Nouf Aljobaily, Kelsey Krutsinger, Michael J Viereckl, Raznin Joly, Bridger Menlove, Brexton Cone, Ailaina Suppes, Yuyan Han. Low-Dose Administration of Cannabigerol Attenuates Inflammation and Fibrosis Associated with Methionine/Choline Deficient Diet-Induced NASH Model via Modulation of Cannabinoid Receptor. Nutrients. 2022 Dec; 15(1):. doi: 10.3390/nu15010178. [PMID: 36615835]
  • Diana E Sepulveda, Daniel P Morris, Wesley M Raup-Konsavage, Dongxiao Sun, Kent E Vrana, Nicholas M Graziane. Cannabigerol (CBG) attenuates mechanical hypersensitivity elicited by chemotherapy-induced peripheral neuropathy. European journal of pain (London, England). 2022 10; 26(9):1950-1966. doi: 10.1002/ejp.2016. [PMID: 35899583]
  • Anna Jastrząb, Iwona Jarocka-Karpowicz, Elżbieta Skrzydlewska. The Origin and Biomedical Relevance of Cannabigerol. International journal of molecular sciences. 2022 Jul; 23(14):. doi: 10.3390/ijms23147929. [PMID: 35887277]
  • Cilla Zhou, Neda Assareh, Jonathon C Arnold. The Cannabis Constituent Cannabigerol Does Not Disrupt Fear Memory Processes or Stress-Induced Anxiety in Mice. Cannabis and cannabinoid research. 2022 06; 7(3):294-303. doi: 10.1089/can.2021.0027. [PMID: 34182770]
  • Kara Amstutz, Wayne S Schwark, Alexander Zakharov, Beatriz Gomez, Alex Lyubimov, Karolynn Ellis, Kurt P Venator, Joseph J Wakshlag. Single dose and chronic oral administration of cannabigerol and cannabigerolic acid-rich hemp extract in fed and fasted dogs: Physiological effect and pharmacokinetic evaluation. Journal of veterinary pharmacology and therapeutics. 2022 May; 45(3):245-254. doi: 10.1111/jvp.13048. [PMID: 35246858]
  • Eduardo Perez, Jose R Fernandez, Corey Fitzgerald, Karl Rouzard, Masanori Tamura, Christopher Savile. In Vitro and Clinical Evaluation of Cannabigerol (CBG) Produced via Yeast Biosynthesis: A Cannabinoid with a Broad Range of Anti-Inflammatory and Skin Health-Boosting Properties. Molecules (Basel, Switzerland). 2022 Jan; 27(2):. doi: 10.3390/molecules27020491. [PMID: 35056807]
  • Francesco Tolomeo, Fabiana Russo, Maria Angela Vandelli, Giuseppe Biagini, Anna Laura Capriotti, Aldo Laganà, Luigi Carbone, Giuseppe Gigli, Giuseppe Cannazza, Cinzia Citti. HPLC-UV-HRMS analysis of cannabigerovarin and cannabigerobutol, the two impurities of cannabigerol extracted from hemp. Journal of pharmaceutical and biomedical analysis. 2021 Sep; 203(?):114215. doi: 10.1016/j.jpba.2021.114215. [PMID: 34153935]
  • Carmen Lorena Robaina Cabrera, Sandra Keir-Rudman, Nick Horniman, Nick Clarkson, Clive Page. The anti-inflammatory effects of cannabidiol and cannabigerol alone, and in combination. Pulmonary pharmacology & therapeutics. 2021 08; 69(?):102047. doi: 10.1016/j.pupt.2021.102047. [PMID: 34082108]
  • Seth Crawford, Brendan M Rojas, Eric Crawford, Matthew Otten, Thecla A Schoenenberger, Andrea R Garfinkel, Hsuan Chen. Characteristics of the Diploid, Triploid, and Tetraploid Versions of a Cannabigerol-Dominant F1 Hybrid Industrial Hemp Cultivar, Cannabis sativa 'Stem Cell CBG'. Genes. 2021 06; 12(6):. doi: 10.3390/genes12060923. [PMID: 34204324]
  • Rahul Nachnani, Wesley M Raup-Konsavage, Kent E Vrana. The Pharmacological Case for Cannabigerol. The Journal of pharmacology and experimental therapeutics. 2021 02; 376(2):204-212. doi: 10.1124/jpet.120.000340. [PMID: 33168643]
  • Peter B Sampson. Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the 'Big Two'. Journal of natural products. 2021 01; 84(1):142-160. doi: 10.1021/acs.jnatprod.0c00965. [PMID: 33356248]
  • Eleftherios G Andriotis, Konstantina Chachlioutaki, Paraskevi Kyriaki Monou, Nikolaos Bouropoulos, Dimitrios Tzetzis, Panagiotis Barmpalexis, Ming-Wei Chang, Zeeshan Ahmad, Dimitrios G Fatouros. Development of Water-Soluble Electrospun Fibers for the Oral Delivery of Cannabinoids. AAPS PharmSciTech. 2021 Jan; 22(1):23. doi: 10.1208/s12249-020-01895-7. [PMID: 33400042]
  • Kostas Ioannidis, Evangelos Dadiotis, Vangelis Mitsis, Eleni Melliou, Prokopios Magiatis. Biotechnological Approaches on Two High CBD and CBG Cannabis sativa L. (Cannabaceae) Varieties: In Vitro Regeneration and Phytochemical Consistency Evaluation of Micropropagated Plants Using Quantitative 1H-NMR. Molecules (Basel, Switzerland). 2020 Dec; 25(24):. doi: 10.3390/molecules25245928. [PMID: 33333745]
  • Ayat Zagzoog, Kawthar A Mohamed, Hye Ji J Kim, Eunhyun D Kim, Connor S Frank, Tallan Black, Pramodkumar D Jadhav, Larry A Holbrook, Robert B Laprairie. In vitro and in vivo pharmacological activity of minor cannabinoids isolated from Cannabis sativa. Scientific reports. 2020 11; 10(1):20405. doi: 10.1038/s41598-020-77175-y. [PMID: 33230154]
  • Recardia Schoeman, Natasha Beukes, Carminita Frost. Cannabinoid Combination Induces Cytoplasmic Vacuolation in MCF-7 Breast Cancer Cells. Molecules (Basel, Switzerland). 2020 Oct; 25(20):. doi: 10.3390/molecules25204682. [PMID: 33066359]
  • Marilyn A Huestis, Cristina Sempio, Matthew N Newmeyer, Maria Andersson, Allan J Barnes, Osama A Abulseoud, Benjamin C Blount, Jennifer Schroeder, Michael L Smith. Free and Glucuronide Urine Cannabinoids after Controlled Smoked, Vaporized and Oral Cannabis Administration in Frequent and Occasional Cannabis Users. Journal of analytical toxicology. 2020 Oct; 44(7):651-660. doi: 10.1093/jat/bkaa046. [PMID: 32369162]
  • Yannick Nuapia, Hlanganani Tutu, Luke Chimuka, Ewa Cukrowska. Selective Extraction of Cannabinoid Compounds from Cannabis Seed Using Pressurized Hot Water Extraction. Molecules (Basel, Switzerland). 2020 Mar; 25(6):. doi: 10.3390/molecules25061335. [PMID: 32183432]
  • Daniel I Brierley, Joe R Harman, Natasha Giallourou, Emma Leishman, Anna Emily Roashan, Ben A D Mellows, Heather B Bradshaw, Jonathan R Swann, Ketan Patel, Benjamin J Whalley, Claire M Williams. Chemotherapy-induced cachexia dysregulates hypothalamic and systemic lipoamines and is attenuated by cannabigerol. Journal of cachexia, sarcopenia and muscle. 2019 08; 10(4):844-859. doi: 10.1002/jcsm.12426. [PMID: 31035309]
  • Lucia Marchetti, Virginia Brighenti, Maria Cecilia Rossi, Johanna Sperlea, Federica Pellati, Davide Bertelli. Use of 13C-qNMR Spectroscopy for the Analysis of Non-Psychoactive Cannabinoids in Fibre-Type Cannabis sativa L. (Hemp). Molecules (Basel, Switzerland). 2019 Mar; 24(6):. doi: 10.3390/molecules24061138. [PMID: 30909372]
  • Christopher W Cunningham. Plant-Based Modulators of Endocannabinoid Signaling. Journal of natural products. 2019 03; 82(3):636-646. doi: 10.1021/acs.jnatprod.8b00874. [PMID: 30816712]
  • Enrico D'Aniello, Tariq Fellous, Fabio Arturo Iannotti, Alessandra Gentile, Marco Allarà, Francesca Balestrieri, Roy Gray, Pietro Amodeo, Rosa Maria Vitale, Vincenzo Di Marzo. Identification and characterization of phytocannabinoids as novel dual PPARα/γ agonists by a computational and in vitro experimental approach. Biochimica et biophysica acta. General subjects. 2019 03; 1863(3):586-597. doi: 10.1016/j.bbagen.2019.01.002. [PMID: 30611848]
  • Karl B Scheidweiler, Allan J Barnes. Quantification of Eight Cannabinoids Including Cannabidiol in Human Urine Via Liquid Chromatography Tandem Mass Spectrometry. Methods in molecular biology (Clifton, N.J.). 2019; 1872(?):11-22. doi: 10.1007/978-1-4939-8823-5_2. [PMID: 30350275]
  • Antonella Smeriglio, Salvatore V Giofrè, Enza M Galati, Maria T Monforte, Nicola Cicero, Valeria D'Angelo, Gianpaolo Grassi, Clara Circosta. Inhibition of aldose reductase activity by Cannabis sativa chemotypes extracts with high content of cannabidiol or cannabigerol. Fitoterapia. 2018 Jun; 127(?):101-108. doi: 10.1016/j.fitote.2018.02.002. [PMID: 29427593]
  • Yan-Hong Wang, Bharathi Avula, Mahmoud A ElSohly, Mohamed M Radwan, Mei Wang, Amira S Wanas, Zlatko Mehmedic, Ikhlas A Khan. Quantitative Determination of Δ9-THC, CBG, CBD, Their Acid Precursors and Five Other Neutral Cannabinoids by UHPLC-UV-MS. Planta medica. 2018 Mar; 84(4):260-266. doi: 10.1055/s-0043-124873. [PMID: 29262425]
  • Xavier Nadal, Carmen Del Río, Salvatore Casano, Belén Palomares, Carlos Ferreiro-Vera, Carmen Navarrete, Carolina Sánchez-Carnerero, Irene Cantarero, Maria Luz Bellido, Stefan Meyer, Gaetano Morello, Giovanni Appendino, Eduardo Muñoz. Tetrahydrocannabinolic acid is a potent PPARγ agonist with neuroprotective activity. British journal of pharmacology. 2017 Dec; 174(23):4263-4276. doi: 10.1111/bph.14019. [PMID: 28853159]
  • Bhupendra Patel, Daniel Wene, Zhihua Tina Fan. Qualitative and quantitative measurement of cannabinoids in cannabis using modified HPLC/DAD method. Journal of pharmaceutical and biomedical analysis. 2017 Nov; 146(?):15-23. doi: 10.1016/j.jpba.2017.07.021. [PMID: 28841427]
  • Daniel I Brierley, James Samuels, Marnie Duncan, Benjamin J Whalley, Claire M Williams. A cannabigerol-rich Cannabis sativa extract, devoid of [INCREMENT]9-tetrahydrocannabinol, elicits hyperphagia in rats. Behavioural pharmacology. 2017 06; 28(4):280-284. doi: 10.1097/fbp.0000000000000285. [PMID: 28125508]
  • Wieland Peschel, Matteo Politi. ¹H NMR and HPLC/DAD for Cannabis sativa L. chemotype distinction, extract profiling and specification. Talanta. 2015 Aug; 140(?):150-165. doi: 10.1016/j.talanta.2015.02.040. [PMID: 26048837]
  • Ester Pagano, Vittorino Montanaro, Antonio Di Girolamo, Antonio Pistone, Vincenzo Altieri, Jordan K Zjawiony, Angelo A Izzo, Raffaele Capasso. Effect of Non-psychotropic Plant-derived Cannabinoids on Bladder Contractility: Focus on Cannabigerol. Natural product communications. 2015 Jun; 10(6):1009-12. doi: . [PMID: 26197538]
  • Sara Valdeolivas, Carmen Navarrete, Irene Cantarero, María L Bellido, Eduardo Muñoz, Onintza Sagredo. Neuroprotective properties of cannabigerol in Huntington's disease: studies in R6/2 mice and 3-nitropropionate-lesioned mice. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2015 Jan; 12(1):185-99. doi: 10.1007/s13311-014-0304-z. [PMID: 25252936]
  • Andrew J Hill, Nicholas A Jones, Imogen Smith, Charlotte L Hill, Claire M Williams, Gary J Stephens, Benjamin J Whalley. Voltage-gated sodium (NaV) channel blockade by plant cannabinoids does not confer anticonvulsant effects per se. Neuroscience letters. 2014 Apr; 566(?):269-74. doi: 10.1016/j.neulet.2014.03.013. [PMID: 24642454]
  • Mariangela Pucci, Cinzia Rapino, Andrea Di Francesco, Enrico Dainese, Claudio D'Addario, Mauro Maccarrone. Epigenetic control of skin differentiation genes by phytocannabinoids. British journal of pharmacology. 2013 Oct; 170(3):581-91. doi: 10.1111/bph.12309. [PMID: 23869687]
  • Katherine Ann Scott, Sini Shah, Angus George Dalgleish, Wai Man Liu. Enhancing the activity of cannabidiol and other cannabinoids in vitro through modifications to drug combinations and treatment schedules. Anticancer research. 2013 Oct; 33(10):4373-80. doi: ". [PMID: 24123005]
  • Francesca Borrelli, Ines Fasolino, Barbara Romano, Raffaele Capasso, Francesco Maiello, Diana Coppola, Pierangelo Orlando, Giovanni Battista, Ester Pagano, Vincenzo Di Marzo, Angelo A Izzo. Beneficial effect of the non-psychotropic plant cannabinoid cannabigerol on experimental inflammatory bowel disease. Biochemical pharmacology. 2013 May; 85(9):1306-16. doi: 10.1016/j.bcp.2013.01.017. [PMID: 23415610]
  • Serena Deiana, Akihito Watanabe, Yuki Yamasaki, Naoki Amada, Marlene Arthur, Shona Fleming, Hilary Woodcock, Patricia Dorward, Barbara Pigliacampo, Steve Close, Bettina Platt, Gernot Riedel. Plasma and brain pharmacokinetic profile of cannabidiol (CBD), cannabidivarine (CBDV), Δ⁹-tetrahydrocannabivarin (THCV) and cannabigerol (CBG) in rats and mice following oral and intraperitoneal administration and CBD action on obsessive-compulsive behaviour. Psychopharmacology. 2012 Feb; 219(3):859-73. doi: 10.1007/s00213-011-2415-0. [PMID: 21796370]
  • L De Petrocellis, P Orlando, A Schiano Moriello, G Aviello, C Stott, A A Izzo, V Di Marzo. Cannabinoid actions at TRPV channels: effects on TRPV3 and TRPV4 and their potential relevance to gastrointestinal inflammation. Acta physiologica (Oxford, England). 2012 Feb; 204(2):255-66. doi: 10.1111/j.1748-1716.2011.02338.x. [PMID: 21726418]
  • Sharon Anavi-Goffer, Gemma Baillie, Andrew J Irving, Jürg Gertsch, Iain R Greig, Roger G Pertwee, Ruth A Ross. Modulation of L-α-lysophosphatidylinositol/GPR55 mitogen-activated protein kinase (MAPK) signaling by cannabinoids. The Journal of biological chemistry. 2012 Jan; 287(1):91-104. doi: 10.1074/jbc.m111.296020. [PMID: 22027819]
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