Terpenes: Therapeutic Constituents in Medicinal Mushrooms, Part 2

by Anna Sitkoff

Terpenes are fat- and alcohol-soluble compounds that come in many variations - monoterpenes, sesquiterpenes, diterpenes and triterpenes. The prefix indicates the number of carbons in the molecule: 10, 15, 20, and 30, respectively. As the terpene becomes bigger, it also becomes heavier and less volatile. The mushroom smell many are familiar with is in part due to low-molecular weight molecules that make their way into the nose - the monoterpenes and sesquiterpenes. These lower-weight chemicals act as attractants and deterrents to insects and other invertebrates, acting as both pheromones and defense chemicals. The most well-known terpenes in fungi are both found in lion’s mane. Erinicines, a group of diterpenoids, have nootropic properties and are found in lion’s mane mycelium, while the terpene hericenones, which are also nootropic, are found in lion’s mane fruiting body.

Erinacine E Hericenone A
Erinacine E, a terpenoid Hericenone A, a terpenoid

 

As the mushroom matures from primordia to fruiting body, an enzyme stimulates the synthesis of triterpenes. Because of this, there are significantly more triterpenes in the mushroom compared to the mycelium and primordia. Triterpenes in mushrooms are lanostane triterpenes, and can be referred to as “lanostanoids”. The most well-known triterpenes found in mushrooms are ganoderic acids, found in various species of reishi. These terpenes are major compounds of interest in cancer research because they have cytotoxic activity in many cancer cell lines; they also demonstrate specific antiviral activity, and are helpful in the treatment of hypersensitivity reactions.

Anti-neoplastic

There are a significant number of in vitro and in vivo animal studies demonstrating direct anti-neoplastic activity of triterpenes. These molecules are cytotoxic to many cancer cell lines, as well as instigators of an antineoplastic immune response (1,2,3,4,5,6).

Anti-viral

Mushroom-derived triterpenes and sesquiterpenes have specific antiviral activity through the inhibition of the enzyme neuraminidase, which viruses use to leave one cell to enter another (7,8). In addition to anti-neuraminidase activity, triterpenes stimulate an immune response that preferences cytotoxic CD8 T cells, a major component of adaptive antiviral immunity (9).

Cryptoporic acid A, a terpene with anti-neuraminidase activity
  Cryptoporic acid A, a terpene with anti-neuraminidase activity

Anti-allergic

Triterpenes may be very beneficial in the treatment of hypersensitivity reactions including allergy, dermatitis and rhinitis. Ganoderic acids from reishi inhibit histamine release from mast cells, which can moderate the severity of allergic reactions (10). Ganoderic acids have also been shown to induce the release of the cytokines IL-10 and IFN-𝛾, suppressing TH2 responses in favor of TH1, and moving the immune system away from allergic responses (11).

Click to explore our professional reishi monograph

 Ganoderic acid A, a triterpene
Ganoderic acid A, a triterpene

Neuroprotective

Erinacines and hericenones, diterpenes found in lion’s mane mycelium and fruiting body, respectively, both have neuroprotective activity (12). Both molecules have demonstrated neurogenesis via nerve growth factor synthase activation, and erinacines improve plaque formation in mouse models of Alzheimer’s disease while increasing hippocampal neurogenesis (12).

Click to explore our professional lion's mane monograph

Absorption

Only 10% of terpenes found in fungi are bioavailable with oral consumption, potentially due to first-pass metabolism in the liver and metabolism by intestinal bacteria (13). Raw mushrooms offer particularly poor bioavailability, as terpenes remain trapped inside fungal cells, while mushroom extracts offer improved absorption. Taking terpene-rich extracts with food impairs absorption; for best results, take terpene-rich mushrooms as extracts on an empty stomach (14).

To learn more, check out our blog post on factors impacting the absorption of mushroom constituents.

DIY Extraction of Terpenes

Terpenes are alcohol- and fat-soluble and range from low- to high-molecular weight

  1. Infuse chopped mushrooms into oil and use as a base for lotion, salad dressings or flavorful drizzle

  2. Soak dried and chopped mushrooms in alcohol as part of a double extraction process.

References

  1. Ríos JL. Effects of triterpenes on the immune system. J Ethnopharmacol. 2010;128(1):1-14. doi:10.1016/j.jep.2009.12.045.
  2. Grienke U, Kaserer T, Pfluger F, et al. Accessing biological actions of Ganoderma secondary metabolites by in silico profiling. Phytochemistry. 2015;114:114-124. doi:10.1016/j.phytochem.2014.10.010.
  3. Bhattarai G, Lee Y-H, Lee N-H, et al. Fomitoside-K from Fomitopsis nigra Induces Apoptosis of Human Oral Squamous Cell Carcinomas (YD-10B) via Mitochondrial Signaling Pathway. Biol Pharm Bull. 2012;35(10):1711-1719. doi:10.1248/bpb.12-00297.
  4. Ren G, Liu XY, Zhu HK, Yang SZ, Fu CX. Evaluation of cytotoxic activities of some medicinal polypore fungi from China. Fitoterapia. 2006;77(5):408-410. doi:10.1016/j.fitote.2006.05.004.
  5. Jin X, Ruiz Beguerie J, Sze DM-Y, Chan GCF. Ganoderma lucidum (Reishi mushroom) for cancer treatment. Cochrane database Syst Rev. 2016;4:CD007731. doi:10.1002/14651858.CD007731.pub3.
  6. Zhu Q, Bang TH, Ohnuki K, Sawai T, Sawai K, Shimizu K. Inhibition of neuraminidase by Ganoderma triterpenoids and implications for neuraminidase inhibitor design. Sci Rep. 2015;5(AUGUST):13194. doi:10.1038/srep13194.
  7. Teplyakova T V., Psurtseva N V., Kosogova TA, Mazurkova NA, Khanin VA, Vlasenko VA. Antiviral Activity of Polyporoid Mushrooms (Higher Basidiomycetes) from Altai Mountains (Russia). Int J Med Mushrooms. 2012;14(1):37-45. doi:10.1615/IntJMedMushr.v14.i1.40.
  8. Gao L, Sun Y, Si J, et al. Cryptoporus volvatus extract inhibits influenza virus replication in vitro and in vivo. PLoS One. 2014;9(12). doi:10.1371/journal.pone.0113604.
  9. Van Thu Nguyen, Nguyen The Tung, To Dao Cuong, Tran Manh Hung, Jeong Ah Kim, Mi Hee Woo, Jae Sue Choi, Jeong-Hyung Lee, Byung Sun Min, Cytotoxic and anti-angiogenic effects of lanostane triterpenoids from Ganoderma lucidum, Phytochemistry Letters, Volume 12, 2015, Pages 69-74, ISSN 1874-3900, https://doi.org/10.1016/j.phytol.2015.02.012.
  10. Bhardwaj N, Katyal P, Sharma AK. Suppression of inflammatory and allergic responses by pharmacologically potent fungus Ganoderma lucidum. Recent Pat Inflamm Allergy Drug Discov. 2014;8(2):104-17. doi: 10.2174/1872213x08666140619110657. PMID: 24948193.
  11. Liu C, Cao M, Yang N, Reid-Adam J, Tversky J, Zhan J, Li XM. Time-dependent dual beneficial modulation of interferon-γ, interleukin 5, and Treg cytokines in asthma patient peripheral blood mononuclear cells by ganoderic acid B. Phytother Res. 2022 Mar;36(3):1231-1240. doi: 10.1002/ptr.7266. Epub 2022 Feb 3. PMID: 35112740.
  12. Friedman M. Chemistry, Nutrition, and Health-Promoting Properties of Hericium erinaceus (Lion's Mane) Mushroom Fruiting Bodies and Mycelia and Their Bioactive Compounds. J Agric Food Chem. 2015;63(32):7108-7123. doi:10.1021/acs.jafc.5b02914
  13. Teekachunhatean, S., Sadja, S., Ampasavate, C., Chiranthanut, N., Rojanasthien, N., & Sangdee, C. (2012). Pharmacokinetics of Ganoderic Acids A and F after Oral Administration of Ling Zhi Preparation in Healthy Male Volunteers. Evidence-Based Complementary and Alternative Medicine, 2012, 780892. https://doi.org/10.1155/2012/780892
  14. Verhoeven J, Keller D, Verbruggen S, Abboud KY, Venema K. A blend of 3 mushrooms dose-dependently increases butyrate production by the gut microbiota. Benef Microbes. 2021;12(6):601-612. doi:10.3920/BM2021.0015
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