Pinene is unique inthat it has two main isomers, alpha and beta, that are both common in the cannabis plant. These isomers have the same molecular composition but different arrangements and are usually notated as α-pinene and β-pinene. As its name suggests, this terpene has a piney aroma and is abundant in most conifers. Pinene can be found in a large variety of plants, including rosemary, parsley, dill and—not surprisingly—pine trees! Various animal studies have demonstrated that pinene may exhibit gastroprotective[1], anxiolytic[2], and anticonvulsant[3] properties, as well as the potential to improve sleep quality[4]. In addition, some animal and in vitro studies have implicated this terpene as a potential treatment for various neurodegenerative diseases[5], including Alzheimer’s[6] and Parkinson’s Disease[7], due to its neuroprotective properties[8]. In vitro research, including studies on essential oils rich in pinene, has shown that pinene may display antioxidant[9], anti-inflammatory[10], and antimicrobial[11] effects. Finally, as with several other terpenes, pinene has been linked to anti-tumor[12] and anti-cancer[13] activity.
[1] Pinheiro Mde A, Magalhães RM, Torres DM, Cavalcante RC, Mota FS, Oliveira Coelho EM, Moreira HP, Lima GC, Araújo PC, Cardoso JH, de Souza AN, Diniz LR. Gastroprotective effect of alpha-pinene and its correlation with antiulcerogenic activity of essential oils obtained from Hyptis species. Pharmacogn Mag. 2015 Jan-Mar;11(41):123-30. doi: 10.4103/0973-1296.149725. PMID: 25709221; PMCID: PMC4329611.
[2] Kasuya H, Okada N, Kubohara M, Satou T, Masuo Y, Koike K. Expression of BDNF and TH mRNA in the brain following inhaled administration of α-pinene. Phytother Res. 2015 Jan;29(1):43-7. doi: 10.1002/ptr.5224. Epub 2014 Sep 17. PMID: 25230317.
[3] Felipe CFB, Albuquerque AMS, de Pontes JLX, de Melo JÍV, Rodrigues TCML, de Sousa AMP, Monteiro ÁB, Ribeiro AEDS, Lopes JP, de Menezes IRA, de Almeida RN. Comparative study of alpha- and beta-pinene effect on PTZ-induced convulsions in mice. Fundam Clin Pharmacol. 2019 Apr;33(2):181-190. doi: 10.1111/fcp.12416. Epub 2018 Oct 25. PMID: 30230028.
[4] Yang H, Woo J, Pae AN, Um MY, Cho NC, Park KD, Yoon M, Kim J, Lee CJ, Cho S. α-Pinene, a Major Constituent of Pine Tree Oils, Enhances Non-Rapid Eye Movement Sleep in Mice through GABAA-benzodiazepine Receptors. Mol Pharmacol. 2016 Nov;90(5):530-539. doi: 10.1124/mol.116.105080. Epub 2016 Aug 29. PMID: 27573669.
[5] Porres-Martínez M, González-Burgos E, Carretero ME, Gómez-Serranillos MP. In vitro neuroprotective potential of the monoterpenes α-pinene and 1,8-cineole against H2O2-induced oxidative stress in PC12 cells. Z Naturforsch C J Biosci. 2016;71(7-8):191-9. doi: 10.1515/znc-2014-4135. PMID: 27352445.
[6] Lee GY, Lee C, Park GH, Jang JH. Amelioration of Scopolamine-Induced Learning and Memory Impairment byα-Pinene in C57BL/6 Mice. Evid Based Complement Alternat Med. 2017;2017:4926815. doi: 10.1155/2017/4926815. Epub 2017 Nov 1. PMID: 29234406; PMCID: PMC5687139.
[7] Srivastava R, Choudhury PK, Dev SK, Rathore V. Neuroprotective effect of α-pinene self-emulsifying nanoformulation against 6-OHDA induced neurotoxicity on human SH-SY5Y cells and its in vivo validation for anti-Parkinson’s effect. J Biochem Mol Toxicol. 2021 Nov;35(11):e22902. doi: 10.1002/jbt.22902. Epub 2021 Aug 31. PMID: 34464010.
[8] Khoshnazar M, Parvardeh S, Bigdeli MR. Alpha-pinene exerts neuroprotective effects via anti-inflammatory and anti-apoptotic mechanisms in a rat model of focal cerebral ischemia-reperfusion. J Stroke Cerebrovasc Dis. 2020 Aug;29(8):104977. doi: 10.1016/j.jstrokecerebrovasdis.2020.104977. Epub 2020 Jun 13. PMID: 32689608.
[9] Porres-Martínez M, González-Burgos E, Carretero ME, Gómez-Serranillos MP. In vitro neuroprotective potential of the monoterpenes α-pinene and 1,8-cineole against H2O2-induced oxidative stress in PC12 cells. Z Naturforsch C J Biosci. 2016;71(7-8):191-9. doi: 10.1515/znc-2014-4135. PMID: 27352445.
[10] Rufino AT, Ribeiro M, Judas F, Salgueiro L, Lopes MC, Cavaleiro C, Mendes AF. Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity. J Nat Prod. 2014 Feb 28;77(2):264-9. doi: 10.1021/np400828x. Epub 2014 Jan 23. PMID: 24455984.
[11] Rodrigues KA, Amorim LV, Dias CN, Moraes DF, Carneiro SM, Carvalho FA. Syzygium cumini (L.) Skeels essential oil and its major constituent α-pinene exhibit anti-Leishmania activity through immunomodulation in vitro. J Ethnopharmacol. 2015 Feb 3;160:32-40. doi: 10.1016/j.jep.2014.11.024. Epub 2014 Nov 25. PMID: 25460590.
[12] Chen W, Liu Y, Li M, Mao J, Zhang L, Huang R, Jin X, Ye L. Anti-tumor effect of α-pinene on human hepatoma cell lines through inducing G2/M cell cycle arrest. J Pharmacol Sci. 2015 Mar;127(3):332-8. doi: 10.1016/j.jphs.2015.01.008. Epub 2015 Feb 7. PMID: 25837931.
[13] Jo H, Cha B, Kim H, Brito S, Kwak BM, Kim ST, Bin BH, Lee MG. α-Pinene Enhances the Anticancer Activity of Natural Killer Cells via ERK/AKT Pathway. Int J Mol Sci. 2021 Jan 11;22(2):656. doi: 10.3390/ijms22020656. PMID: 33440866; PMCID: PMC7826552.
