Published October 31, 2021
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α-Pinene: A never-ending story
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Allenspach, Martina, Steuer, Christian (2021): α-Pinene: A never-ending story. Phytochemistry (112857) 190: 1-7, DOI: 10.1016/j.phytochem.2021.112857, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112857
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References
- Aguas, I., et al., 2020. Turpentine valorization by its oxyfunctionalization to nopol through heterogeneous catalysis. Heliyon 6 e03887. https://10.1016/j.heliyon.20 20.e03887.
- Allenspach, M., et al., 2020. Verification of chromatographic profile of primary essential oil of Pinus sylvestris L. Combined with chemometric analysis. Molecules 25. http s://10.3390/molecules25132973.
- Avato, P., et al., 2017. Nematicidal activity of essential oils from aromatic plants of Morocco. J. Pest Sci. 90, 711-722. https://doi.org/10.1007/s10340-016-0805-0.
- Avila ´Murilloa, M.C., et al., 2014. Chemical composition and insecticidal properties of essential oils of Piper septuplinervium and P. subtomentosum (Piperaceae). Nat. Prod. Commun 9, 1527-1530. https://doi.org/10.1177/1934578X1400901031.
- Ballabio, D., et al., 2018. Multivariate comparison of classification performance measures. Chemometr. Intell. Lab. Syst. 174, 33-44. https://10.1016/j.ch emolab.2017.12.004.
- Baron, E.P., et al., 2018. Patterns of medicinal cannabis use, strain analysis, and substitution effect among patients with migraine, headache, arthritis, and chronic pain in a medicinal cannabis cohort. J. Headache Pain 19. https://10.1186/s10 194-018-0862-2.
- Baser, K.H.C., Buchbauer, G., 2016. Handbook of Essential Oils Science, Technology, and Applications. CRC Press. https://doi.org/10.1201/b19393.
- Bohm, H.J., et al., 2004. Scaffold hopping. Drug Discov. Today Technol. 1, 217-224. https://10.1016/j.ddtec.2004.10.009.
- Boren, K.E.Y., Woolley, D.G., Smith, C.L., Carlson R E, B.L., 2015. Detecting essential oil adulteration. J. Environ. Anal. Chem. https://10.4172jreac.1000132.
- Borselli, D., et al., 2016. Polyamino-isoprenic derivatives block intrinsic resistance of P. aeruginosa to doxycycline and chloramphenicol in vitro. PLoS One 11. https:// 10.1371/journal.pone.0154490.
- Bouzenna, H., et al., 2017. Potential protective effects of alpha-pinene against cytotoxicity caused by aspirin in the IEC-6 cells. Biomed. Pharmacother. 93, 961-968. https://10.1016/j.biopha.2017.06.031.
- Brunel, J.M., et al., 2013. Polyamino geranic derivatives as new chemosensitizers to combat antibiotic resistant Gram-negative bacteria. Bioorg. Med. Chem. 21, 1174-1179. https://10.1016/j.bmc.2012.12.030.
- Cao, J.-q., et al., 2019. Pinene-rich essential oils from Haplophyllum dauricum (L.) G. Don display anti-insect activity on two stored-product insects. Int. Biodeterior. Biodegrad. 140, 1-8. https://doi.org/10.1016/j.ibiod.2019.03.007.
- Cerceau, C.I., et al., 2020. H-1-NMR and GC for detection of adulteration in commercial essential oils of Cymbopogon ssp. Phytochem. Anal. 31, 88-97. https://10.1002 /pca.2869.
- Chen, W.Q., et al., 2015. Anti-tumor effect of alpha-pinene on human hepatoma cell lines through inducing G2/M cell cycle arrest. J. Pharmacol. Sci. 127, 332-338. https ://10.1016/j.jphs.2015.01.008.
- Chen, W.Q., et al., 2014. Inhibitory effects of alpha-pinene on hepatoma carcinoma cell proliferation. Asian Pac. J. Cancer Prev. APJCP 15, 3293-3297. https://10.7314/a pjcp.2014.15.7.3293.
- Chouhan, S., et al., 2017. Antimicrobial activity of some essential oils-present status and future perspectives. Medicines (Basel) 4. https://10.3390/medicines4030058.
- Da Silva, A.C., et al., 2012. Biological activities of alpha-pinene and beta-pinene enantiomers. Molecules 17, 6305-6316, 10.3390/molecules17066305.
- de Sousa Eduardo, L., et al., 2018. Antibacterial activity and time-kill kinetics of positive enantiomer of alpha-pinene against strains of Staphylococcus aureus and Escherichia coli. Curr. Top. Med. Chem. 18, 917-924. https://10.2174/15680266186661807120 93914.
- Do, T.K.T., et al., 2015. Authenticity of essential oils. Trac. Trends Anal. Chem. 66, 146-157. https://doi.org/10.1016/j.trac.2014.10.007.
- Dong, H., et al., 2020. Synthesis and herbicidal application of turpentine derivative pmenthene type secondary amines as sustainable agrochemicals. New J. Chem. 44, 8280-8288. https://10.1039/D0NJ00583E.
- Dosoky, N.S., et al., 2019. Volatiles of Black Pepper Fruits (Piper Nigrum L.), vol. 24. Molecules. https://10.3390/molecules24234244.
- Douafer, H., et al., 2019. Antibiotic adjuvants: make antibiotics great again! J. Med. Chem. 62, 8665-8681. https://10.1021/acs.jmedchem.8b01781.
- Fahed, L., et al., 2017. Essential oils composition and antimicrobial activity of six conifers harvested in Lebanon. Chem. Biodivers. 14. https://10.1002/cbdv. 201600235.
- Feyaerts, A.F., et al., 2020. Striking essential oil: tapping into a largely unexplored source for drug discovery. Sci Rep-Uk 10. https://10.1038/s41598-020-59332-5.
- Finlay, D.B.S., Nimick, K.J., Jones, M., Glass M, C., 2020. Terpenoids from Cannabis do not mediate an entourage effect by acting at cannabinoid receptors. Front. Pharmacol. https://10.3389/fphar.2020.00359.
- Goudarzi, S., Rafieirad, M., 2017. Evaluating the effect of alpha-pinene on motor activity, avoidance memory and lipid peroxidation in animal model of Parkinson disease in adult male rats. Res. J. Pharmacogn. 4, 53-63.
- Hanus, L., et al., 1999. HU-308: a specific agonist for CB2, a peripheral cannabinoid receptor. Proc. Natl. Acad. Sci. U. S. A 96, 14228-14233. https://10.1073/pnas.96 .25.14228.
- Harvey, A.L., et al., 2015. The re-emergence of natural products for drug discovery in the genomics era. Nat. Rev. Drug Discov. 14, 111-129. https://10.1038/nrd4510.
- Herrmann, F., Wink, M., 2011. Synergistic interactions of saponins and monoterpenes in HeLa cells, Cos7 cells and in erythrocytes. Phytomedicine 18, 1191-1196. https://10 .1016/j.phymed.2011.08.070.
- Ho, D.X., et al., 2011. Emission rates of volatile organic compounds released from newly produced household furniture products using a large-scale chamber testing method. Sci. World J. 11, 1597-1622. https://10.1100/2011/650624.
- Hou, J., et al., 2019. Alpha-pinene induces apoptotic cell death via caspase activation in human ovarian cancer cells. Med. Sci. Mon. 25, 6631-6638. https://10.12659/MSM .916419.
- Isman, M.B., et al., 2008. Insecticidal activities of commercial rosemary oils (rosmarinus officinalis.) against larvae of pseudaletia unipuncta. And trichoplusia ni. In relation to their chemical compositions. Pharm. Biol. 46, 82-87. https://10.1080/13880200 701734661.
- Kachur, K., Suntres, Z., 2019. The antibacterial properties of phenolic isomers, carvacrol and thymol. Crit. Rev. Food Sci. Nutr. https://10.1080/10408398.2019.1675585.
- Karthikeyan, R., et al., 2018. Alpha pinene modulates UVA-induced oxidative stress, DNA damage and apoptosis in human skin epidermal keratinocytes. Life Sci. 212, 150-158. https://10.1016/j.lfs.2018.10.004.
- Khoshnazar, M., et al., 2020. 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. 29, 104977. https://10.1016/j.jstr okecerebrovasdis.2020.104977.
- Kim, D.S., et al., 2015. Alpha-pinene exhibits anti-inflammatory activity through the suppression of MAPKs and the NF-kappa B pathway in mouse peritoneal macrophages. Am. J. Chin. Med. 43, 731-742. https://10.1142/S0192415x1550045 7.
- Kovac, J., et al., 2015. Antibiotic resistance modulation and modes of action of (-)-alpha-pinene in Campylobacter jejuni. PLoS One 10, e0122871. https://10.1371/journal. pone.0122871.
- Langsi, J.D., et al., 2020. Evaluation of the insecticidal activities of alpha-pinene and 3- carene on sitophilus zeamais motschulsky (Coleoptera: Curculionidae). Insects 11. https://10.3390/insects11080540.
- Lee, G.Y., et al., 2017. Amelioration of scopolamine-induced learning and memory impairment by alpha-pinene in C57BL/6 mice. Evid. Based Complement. Alternat. Med. 2017, 4926815. https://10.1155/2017/4926815.
- Lewis, M.A., et al., 2018. Pharmacological foundations of cannabis chemovars. Planta Med. 84, 225-233. https://10.1055/s-0043-122240.
- Lin, G., et al., 2019. High value-added application of sustainable natural forest product α- pinene: synthesis of myrtenal oxime esters as potential KARI inhibitors. ACS Sustain. Chem. Eng. 7, 7862-7868. https://10.1021/acssuschemeng.9b00254.
- Liu, S.-W., et al., 2008. Reactions of α- pinene using acidic ionic liquids as catalysts. J. Mol. Catal. Chem. 279, 177-181. https://doi.org/10.1016/j.molcata.2007.06.026.
- Loziene, K., et al., 2018. Influence of plant origin natural alpha-pinene with different enantiomeric composition on bacteria, yeasts and fungi. Fitoterapia 127, 20-24. https://10.1016/j.fitote.2018.04.013.
- Matsuo, A.L., et al., 2011. alpha-Pinene isolated from Schinus terebinthifolius Raddi (Anacardiaceae) induces apoptosis and confers antimetastatic protection in a melanoma model. Biochem. Biophys. Res. Commun. 411, 449-454. https://10.1016 /j.bbrc.2011.06.176.
- Mayr, F., et al., 2020. Finding new molecular targets of familiar natural products using in silico target prediction. Int. J. Mol. Sci. 21. https://10.3390/ijms21197102.
- McHale, D., 2002. Adulteration of citrus oils. Med. Aromat. Plants Ind. Profiles 26, 496-517.
- Mercier, B., et al., 2009. The essential oil of turpentine and its major volatile fraction (alpha- and beta-pinenes): a review. Int. J. Occup. Med. Environ. Health 22, 331-342. https://10.2478/v10001-009-0032-5.
- Miyazawa, M., Yamafuji, C., 2005. Inhibition of acetylcholinesterase activity by bicyclic monoterpenoids. J. Agric. Food Chem. 53, 1765-1768. https://10.1021/jf040019b.
- Nazzaro, F., et al., 2013. Effect of Essential Oils on Pathogenic Bacteria, vol. 6. Pharmaceuticals, (Basel, Switzerland), pp. 1451-1474. https://10.3390/ph6121451.
- Ng, T.B., et al., 2016. Chapter 2-methods for the characterization, authentication, and adulteration of essential oils. In: Preedy, V.R. (Ed.), Essential Oils in Food Preservation, Flavor and Safety. Academic Press, San Diego, pp. 11-17. https://doi. org/10.1016/B978-0-12-416641-7.00002-X.
- Nikitina, L.E., et al., 2009. Synthesis and antifungal activity of compounds of the pinane series. Pharmaceut. Chem. J. 43, 251-254. https://10.1007/s11094-009-0282-3.
- Nobrega, J.R., et al., 2020. Antifungal action of alpha-pinene against Candida spp. isolated from patients with otomycosis and effects of its association with boric acid. Nat. Prod. Res. 1-4. https://10.1080/14786419.2020.1837803.
- Pinheiro, M.D., et al., 2015. Gastroprotective effect of alpha-pinene and its correlation with antiulcerogenic activity of essential oils obtained from Hyptis species. Phcog. Mag. 11, 123-130. https://10.4103/0973-1296.149725.
- Pollini, G.P., et al., 2010. Hagemann' s ester: a timeless building block for natural product synthesis. Tetrahedron 66, 2775-2802. https://doi.org/10.1016/j.tet.2010.01.078.
- Porres-Martinez, M., et al., 2016. In vitro neuroprotective potential of the monoterpenes α- pinene and 1,8-cineole against H2O2-induced oxidative stress in PC12 cells. Z. Naturforsch. C Biosci. 71, 191-199. https://10.1515/znc-2014-4135.
- Prakoso, T., et al., 2018. Synthesis of terpineol from α- pinene using low-price acid catalyst. Catal. Lett. 148, 725-731. https://10.1007/s10562-017-2267-2.
- Rodrigues, K.A., et al., 2015. Syzygium cumini (L.) skeels essential oil and its major constituent alpha-pinene exhibit anti-Leishmania activity through immunomodulation in vitro. J. Ethnopharmacol. 160, 32-40. https://10.1016/j.jep .2014.11.024.
- Rufino, A.T., et al., 2014. Anti-inflammatory and chondroprotective activity of (+)- α- pinene: structural and enantiomeric selectivity. J. Nat. Prod. 77, 264-269. https:// 10.1021/np400828x.
- Russo, E.B., 2011. Taming THC: potential cannabis synergy and phytocannabinoidterpenoid entourage effects. Br. J. Pharmacol. 163, 1344-1364. https://10.1111/j.1 476-5381.2011.01238.x.
- Russo, E.B., Marcu, J., 2017. Cannabis pharmacology: the usual suspects and a few promising leads. Cannabinoid Pharmacol. 80, 67-134. https://10.1016/bs.apha.20 17.03.004.
- Salakhutdinov, N.F., et al., 2017. Monoterpenes as a renewable source of biologically active compounds. Pure Appl. Chem. 89, 1105-1117. https://10.1515/pac-2017-0 109.
- Santiago, M.S., Arnold, S., McGregor, J.C., Connor M, I.S., 2019. Absence of entourage: terpenoids commonly found in Cannabis sativa do not modulate the functional activity of Δ9-THC at human CB1 and CB2 receptors. Cannabis Cannabinoid Res. 4. https://10.1089/can.2019.0016.
- Sarria, S., et al., 2014. Microbial synthesis of pinene. ACS Synth. Biol. 3, 466-475. https://10.1021/sb4001382.
- Szakonyi, Z., Fulop, F., 2011. Monoterpene-based chiral beta-amino acid derivatives prepared from natural sources: syntheses and applications. Amino Acids 41, 597-608. https://10.1007/s00726-011-0891-5.
- Tolstikova, T.G., et al., 2008. Derivatives of pinane amino acids as new anticonvulsants. Dokl. Chem. 422, 248-250. https://10.1134/S0012500808100029.
- Trombetta, D., et al., 2005. Mechanisms of antibacterial action of three monoterpenes. Antimicrob. Agents Chemother. 49, 2474-2478. https://10.1128/AAC.49.6.2474- 2478.2005.
- Upshur, M.A., et al., 2019. Synthesis and surface spectroscopy of alpha-pinene isotopologues and their corresponding secondary organic material. Chem. Sci. 10, 8390-8398. https://10.1039/c9sc02399b.
- Utegenova, G.A., et al., 2018. Chemical composition and antibacterial activity of essential oils from Ferula L. species against methicillin-resistant Staphylococcus aureus. Molecules 23. https://10.3390/molecules23071679.
- van Zyl, R.L., et al., 2006. The biological activities of 20 nature identical essential oil constituents. J. Essent. Oil Res. 18, 129-133. https://10.1080/10412905.2006.1206 7134.
- Vespermann, K.A.C., et al., 2017. Biotransformation of alpha- and beta-pinene into flavor compounds. Appl. Microbiol. Biotechnol. 101, 1805-1817. https://10.1007/s00 253-016-8066-7.
- Wang, X., et al., 2019. Effects of alpha-pinene on the pinewood nematode (Bursaphelenchus xylophilus) and its symbiotic bacteria. PloS One 14 e0221099. https://10.1371/journal.pone.0221099.
- Worth, T., 2019. Cannabis' s chemical synergies. Nature 572, S12-S13. https://10.1038 /d41586-019-02528-1.
- Wr´oblewska, A., et al., 2018. Alpha-pinene isomerization over Ti-SBA-15 catalysts obtained by the direct method: the influence of titanium content, temperature, catalyst amount and reaction time. Microporous Mesoporous Mater. 258, 72-82. https://doi.org/10.1016/j.micromeso.2017.09.007.
- Xu, S., et al., 2020. Turpentine derived secondary amines for sustainable crop protection: synthesis, activity evaluation and QSAR study. J. Agric. Food Chem. 68, 11829-11838. https://10.1021/acs.jafc.0c01909.
- Yang, C., et al., 2015. Antibacterial activity and mode of action of the Artemisia capillaris essential oil and its constituents against respiratory tract infection-causing pathogens. Mol. Med. Rep. 11, 2852-2860. https://10.3892/mmr.2014.3103.
- Yang, N.Y., et al., 2011a. Two new alpha-pinene derivatives from Angelica sinensis and their anticoagulative activities. Fitoterapia 82, 692-695. https://10.1016/j.fitote.20 11.02.007.
- Yang, Z., et al., 2011b. Comparative anti-infectious bronchitis virus (IBV) activity of (-)-pinene: effect on nucleocapsid (N) protein. Molecules 16, 1044-1054. http s://10.3390/molecules16021044.
- Ye, L., et al., 2020. Anti-tumor activities and mechanism study of α- pinene derivative in vivo and in vitro. Cancer Chemother. Pharmacol. 85, 367-377. https://10.1007 /s00280-019-03997-x.
- Zamyad, M., et al., 2019. The anticonvulsant effects of Ducrosia anethifolia (Boiss) essential oil are produced by its main component alpha-pinene in rats. Arq. Neuropsiquiatr. 77, 106-114. https://10.1590/0004-282X20180147.
- Zarybnicky, T., et al., 2018. Hepatotoxicity of monoterpenes and sesquiterpenes. Arch. Toxicol. 92, 1-13. https://10.1007/s00204-017-2062-2.
- Zhang, Z., et al., 2015. Synergistic antitumor effect of alpha-pinene and beta-pinene with paclitaxel against non-small-cell lung carcinoma (NSCLC). Drug Res. 65, 214-218. https://10.1055/s-0034-1377025.
- Zhu, S.J., et al., 2017. An efficient synthesis method targeted to a novel aziridine derivative of p-menthane from turpentine and its herbicidal activity. Nat. Prod. Res. 31, 1536-1543. https://10.1080/14786419.2017.1280494.