Horticulture

Pinene: Part of the Forest’s Medicinal Molecular Potion

Alpha-Pinene (α-pinene) is said to be the most widely encountered monoterpene in nature [1], and as its name indicates, pinene is an integral constituent of the fragrance of the forest. It’s also the main component of turpentine. The alpha and beta isomers of pinene are also found in frankincense, juniper, common herbs like parsley and rosemary, spices like nutmeg, and citrus fruit like lemons and limes.

Breathing deeply in a crisp pine forest can be invigorating and refreshing, and it’s really not surprising given that α-pinene is an expectorant and bronchodilator [2], just like tetrahydrocannabinol (THC). [3] This highlights an explanation for why cannabis has been described for many years as having useful applications for asthmatics.

In addition to its effectiveness in aiding respiration, α-pinene has anti-inflammatory properties. [4] Researchers have found that the α-pinene isomer inhibits inflammation in a specific cell type found in our cartilage, called chondrocytes, thus providing a natural agent for treating osteoarthritis. [4]

α-Pinene has demonstrated anti-cancer activity against human liver cancer cell lines by obstructing tumor cell growth. [5, 6] Also, the essential oil extracted from frankincense, containing about 62% α-pinene, showed a strong effectiveness against breast cancer cells. [7] Another interesting study found that when a group of twelve people who worked at large companies in Tokyo went “forest-bathing”, their natural killer (NK) cell activity increased. [8] NK cells are integral to our immune systems, and provide quick responses to cells infected with viruses and parasites. α-Pinene was one chemical constituent measured in the forest atmosphere that was not detected in urban Tokyo. The authors found that α-pinene, in addition to other terpenes like D-limonene, significantly increased NK activity, as well as the expression of other cytolytic (cell-destroying) molecules like perforin, a protein produced by NK cells that creates lesions in cellular membranes.

Cannabis is often linked to short-term memory loss, however, chemovars high in α-pinene may not submit to that stereotype, as the terpene has been recognized as a memory aid. [9-11] Thus, α-pinene presents an exciting plant-derived molecule offering neuroprotective potential for enhanced management of memory disorders like dementia. [9] Reversible inhibition of the enzyme called acetylcholinesterase provides a useful mechanism for treating neurodegenerative disorders like dementia. The neurotransmitter acetylcholine plays a crucial role in our central nervous systems, especially in regards to our cognitive abilities.

α-Pinene inhibits acetylcholinesterase [10], an enzyme that stops the signals between nerve and muscle cells. Acetylcholine carries electrical signals from nerve cells to muscle cells inside synapses. Once it executes its mission, however, it must be removed or destroyed to prevent confusion with other spent or active neurotransmitters. This is where acetylcholinesterase is a necessary biochemical agent, as it breaks down acetylcholine into acetic acid and choline. When this enzyme is inhibited, though, muscular paralysis can ensue. Doctors are now intentionally obstructing this enzyme in attempts to reverse the common symptoms of Alzheimer’s disease. By inhibiting acetylcholinesterase, intra-synaptic acetylcholine increases in concentration, as does the amount of time it’s an intact, functional neurotransmitter. [11] Substances, like α-pinene, that permit acetylcholine to function longer exemplify the main strategy of commercial drugs used in treating Alzheimer’s disease, since the disease is associated with a decrease in acetylcholine concentration and the neurons that use it.

Cannabis varieties reported to contain higher pinene levels include the legendary Jack Herer, Blue Dream, the Kush Group, and AK-47.

References

[1] Noma Y, Asakawa Y (2010). Biotransformation of monoterpenoids by microorganisms, insects, and mammals. In: Baser KHC, Buchbauer G (eds). Handbook of Essential Oils: Science, Technology, and Applications. CRC Press: Boca Raton, FL, pp. 585–736. [journal impact factor = N/A; cited by 75] [2] Falk, A. et al. “Uptake, distribution and elimination of alpha-pinene in man after exposure by inhalation”, Scand J Work Environ Health, 1990, Volume 16: Pages 372–378. [journal impact factor = 3.775; cited by 118] [3] Williams, S. et al. “Bronchodilator effect of delta1-tetrahydrocannabinol administered by aerosol of asthmatic patients”, Thorax, 1976, Volume 31: Pages 720–723. [journal impact factor = 9.655; cited by 109] [4] Rufino, A. et al. “Anti-inflammatory and Chondroprotective Activity of (+)-α-Pinene: Structural and Enantiomeric Selectivity”, J. Nat. Prod., 2014, Volume 77(2): Pages 264–269. [journal impact factor = 3.281; cited by 66] [5] Chen, W. et al. “Inhibitory effects of α-pinene on hepatoma carcinoma cell proliferation”, Asian Pacific Journal of Cancer Prevention, 2014, Volume 15(7): Pages 3293-3297. [journal impact factor = 1.500; cited by 23] [6] Chen, W. et al. “Anti-tumor effect of α-pinene on human hepatoma cell lines through inducing G2/M cell cycle arrest”, Journal of Pharmacological Sciences, 2015, Volume 127: Pages 332-338. [journal impact factor = 2.575; cited by 55] [7] Hakkim, F. et al. “Frankincense derived heavy terpene cocktail boosting breast cancer cell (MDA-MB-231) death in vitro”, Asian Pac J Trop Biomed, 2015, Volume 5(10): Pages 824–828. [journal impact factor = 1.634; cited by 6] [8] Li, Q. et al. “Forest-bathing enhances human natural killer activity and expression of anti-cancer proteins”, International Journal of Immunopathology and Pharmacology, 2007, Volume 20(2): Pages 3-8. [journal impact factor = 2.117; cited by 180] [9] Lee, G. et al. “Amelioration of Scopolamine-Induced Learning and Memory Impairment by 𝛼-Pinene in C57BL/6 Mice”, Evidence-Based Complementary and Alternative Medicine, 2017, Volume 2017, Article ID 4926815, 9 pages. [journal impact factor = 2.064; cited by 11] [10] Orhan, I. et al. “Inhibitory effect of Turkish Rosmarinus officinalis L. on acetylcholinesterase and butyrylcholinesterase enzymes,” Food Chemistry, Volume 108(2): Pages 663-668. [journal impact factor = 4.946; cited by 123] [11] Čolović, M. et al. “Acetylcholinesterase Inhibitors: Pharmacology and Toxicology”, Curr Neuropharmacol, 2013, Volume 11(3): Pages 315–335. [journal impact factor = 4.068; cited by 766]

About the author

Jason S. Lupoi, Ph.D.

Jason S. Lupoi, Ph.D.

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