Limonene

D-Limonene is a molecule that is found in high levels in lemons (where it derives its name) but also most citrus foods. It holds promise as an anti-cancer agent, and for some reason is marketed as a fat burner despite minimal evidence of fat burning effects. Can be consumed via pulpy lemon juice.

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D-Limonene is a compound known as 'lemon extract' and is found in high levels in lemon juices.

It itself, as well as its related product known as 'perillic acid', are known to be anti-carcinogenic (cancer fighting) and liver healthy. Consumption of D-Limonene in either supplemental form or as freshly squeezed and pulp-containing lemonade has been shown to reduce the formation of some tumor growths and alleviate fat buildup in the liver induced by diet.

Although commercial juices tend to have low levels of D-Limonene, freshly squeezed 'Mediterranean Style' juice with the pulp has high levels of it.

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Also Known As

Lemon Extract, D-Limonene


Things to Note

  • Limonene is non-stimulatory
  • Limonene is one of the volatiles in citrus fruit responsible for its aroma
  • Limonene levels are high in citrus peels, and pulp containing juices have higher amounts of limonene than do pulp-free variants

30-40 liquid oz. of Mediterranean Style (pulp in) lemonade confers approximately 500mg D-Limonene, which can be seen as an active dose.

Otherwise, many benefits are seen with 1g of D-Limonene daily.


Table of Contents:


Edit1. Sources and Structure

1.1. Sources

Limonene has its name derived from 'Lemon', the food source that is most abundant in limonene and among the first sources discovered. It is found in:

  • Lemons (as well as limes)[1]
  • Essential oils from Orange where it acts as an aroma[2]
  • Oils from mandarin and grapefruit[1]
  • Teas derived from Phlomis (Lamiaceae)[3]
  • Cardamom[4]
  • Japanese Catnip[5]

1.2. Structure

Limonene is known as a monoterpene molecule (having one isoterpene in its structure) as well as a cyclic terpene (having a six-carboned ring structure).[6] Alongside Limonene, a well-researched compound is its metabolite 'Perillyl Aldcohol'.


Edit2. Limonene pharmacology

Limonene is colourless hydrocarbon compound that smells of oranges. Despite the scent, it is at highest levels in the rinds of lemons, where it acquires its name from.[1]

Limonene is rapidly and almost wholly absorbed in the GI tract after ingestion, and then gets divided to various body tissues after first pass metabolism in the liver[7] where it may be subject to metabolism into carveol metabolites or perillyl metabolites by CYP2C enzymes[8] of which inter-species differences exist.[9]

After a 1.6g dose, between 52-83% of the dose is excreted in 48 hours[10] and no build up of the compound is seen 21 days after cessation.[11] The half-life of D-limonene in humans is estimated to be between 12 and 24 hours.[11]

The primary metabolites of limonene in humans are perillic acid, dihydroperillic acid, and limonene-1,2-diol.[12] These metabolites are glucuronidated by the liver and excreted via the urine.


Edit3. Limonene from food sources

Serum limonene and metabolite levels are able to be elevated via food consumption. A 30-40 oz. serving of 'Mediterranean Style' lemonade (made with the whole lemons) contains 447-596mg limonene. [13] The termination half-life of perillic acid is shorter than that of D-limonene (in the range of 0.82-1.84 hours) and spiked serum levels of perillic acid 2.08 to 13.98 μM.

Standard Citrus juices in western nations (made without the rind) contain up to 100mg per litre of juice, whereas juices made with the rind included contain up to 1027mg per litre.[14][13]


Edit4. Limonene and liver health

In those with Non-alcoholic Fatty Liver disease (onset by diet), supplementation with D-limonene has been shown (in rats) to reverse the hepatic fatty acid buildup as well as downstream effects caused by the hepatic impairment.[15]

References

  1. Sun J. D-Limonene: safety and clinical applications. Altern Med Rev. (2007)
  2. Perez-Cacho PR, Rouseff RL. Fresh squeezed orange juice odor: a review. Crit Rev Food Sci Nutr. (2008)
  3. Limem-Ben Amor I, et al. Phytochemistry and biological activities of Phlomis species. J Ethnopharmacol. (2009)
  4. Acharya A, et al. Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis. Recent Pat Food Nutr Agric. (2010)
  5. Satomi Y, et al. Production of the monoterpene limonene and modulation of apoptosis-related proteins in embryonic-mouse NIH 3T3 fibroblast cells by introduction of the limonene synthase gene isolated from Japanese catnip (Schizonepeta tenuifolia). Biotechnol Appl Biochem. (2009)
  6. Hyatt DC, et al. Structure of limonene synthase, a simple model for terpenoid cyclase catalysis. Proc Natl Acad Sci U S A. (2007)
  7. Crowell PL, et al. Human metabolism of the experimental cancer therapeutic agent d-limonene. Cancer Chemother Pharmacol. (1994)
  8. Miyazawa M, Shindo M, Shimada T. Metabolism of (+)- and (-)-limonenes to respective carveols and perillyl alcohols by CYP2C9 and CYP2C19 in human liver microsomes. Drug Metab Dispos. (2002)
  9. Shimada T, Shindo M, Miyazawa M. Species differences in the metabolism of (+)- and (-)-limonenes and their metabolites, carveols and carvones, by cytochrome P450 enzymes in liver microsomes of mice, rats, guinea pigs, rabbits, dogs, monkeys, and humans. Drug Metab Pharmacokinet. (2002)
  10. Kodama R, et al. Studies on the metabolism of d-limonene (p-mentha-1,8-diene). IV. Isolation and characterization of new metabolites and species differences in metabolism. Xenobiotica. (1976)
  11. Vigushin DM, et al. Phase I and pharmacokinetic study of D-limonene in patients with advanced cancer. Cancer Research Campaign Phase I/II Clinical Trials Committee. Cancer Chemother Pharmacol. (1998)
  12. Crowell PL, et al. Identification of metabolites of the antitumor agent d-limonene capable of inhibiting protein isoprenylation and cell growth. Cancer Chemother Pharmacol. (1992)
  13. Pharmacokinetics of Perillic Acid in Humans after a Single Dose Administration of a Citrus Preparation Rich in d-Limonene Content
  14. Assessing Dietary D-Limonene Intake for Epidemiological Studies
  15. Dietary d-limonene alleviates insulin resistance and oxidative stress-induced liver injury in high-fat diet and L-NAME-treated rats

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