D-limonene is a monoterpene found in bergamot, black pepper, cardamom, citrus fruits, caraway, eucalyptus, pine, peppermint and spearmint. L-Limonene can be found in certain pine species, and has a more terpentine-like aroma.
Monoterpenes are odorless, highly volatile, prone to oxidation, and insoluble in water.
Links to Plants Containing Limonene
The listings of research below represent a compilation of scientific articles found on the topic, with a very brief overview description of each article/study. This compilation of research articles does not necessarily imply that there are adequate results to demonstrate safe and/or effective human use of any herb listed.
ANTIMICROBIAL / ANTIFUNGAL / ANTIBACTERIAL
- Eucalyptus radiata was tested against Streptococci and Lactobacillus acidophilus. The major constituents have seasonal variance, impacting antibacterial strength, and include: 1,8-cineole, α-terpineol and limonene. From: Mahumane, G. D., van Vuuren, S. F., Kamatou, G., Sandasi, M., & Viljoen, A. M. (2016). Chemical composition and antimicrobial activity of Eucalyptus radiata leaf essential oil, sampled over a year. Journal of Essential Oil Research, 1-14.
- Citrus aurantium (bergamot), C. limon (lemon), Lavandula angustifolia (lavender), Matricaria chamomilla (chamomile), Mentha piperita (peppermint), M. spicata (spearmint), Ocimum basilicum (basil), Origanum vulgare(oregano), Thymus vulgaris (thyme), and Salvia officinalis (sage) along with their constituents were tested against human pathogenic bacteria. The highest and broadest activity was shown by O. vulgare oil and carvacrol had the highest antibacterial activity among the tested constituents. Other significant constituents included: camphor, 1,8-cineole, linalool, linalyl acetate, limonene, menthol, a-pinene, b-pinene, and thymol. From: Soković, M., Glamočlija, J., Marin, P. D., Brkić, D., & van Griensven, L. J. (2010). Antibacterial effects of the essential oils of commonly consumed medicinal herbs using an in vitro model. Molecules, 15(11), 7532-7546.
- Antifungal, anti-aflatoxigenic and antioxidant activity of Citrus maxima and Citrus sinensis essential oils were analyzed. From: Singh, P., Shukla, R., Prakash, B., Kumar, A., Singh, S., Mishra, P. K., & Dubey, N. K. (2010). Chemical profile, antifungal, antia flatoxigenic and antioxidant activity of Citrus maxima Burm. and Citrus sinensis (L.) Osbeck essential oils and their cyclic monoterpene, DL-limonene. Food and Chemical Toxicology, 48(6), 1734-1740.
- Carvone and limonene isolated from spearmint and dill were active against a wide spectrum of human pathogenic fungi and bacteria tested. From: Aggarwal, K. K., Khanuja, S. P. S., Ahmad, A., Santha Kumar, T. R., Gupta, V. K., & Kumar, S. (2002). Antimicrobial activity profiles of the two enantiomers of limonene and carvone isolated from the oils of Mentha spicata and Anethum sowa. Flavour and Fragrance Journal, 17(1), 59-63.
- Limonene and thymol were strongest against Fusarium verticillioides in vitro. From: Dambolena, J. S., López, A. G., Cánepa, M. C., Theumer, M. G., Zygadlo, J. A., & Rubinstein, H. R. (2008). Inhibitory effect of cyclic terpenes (limonene, menthol, menthone and thymol) on Fusarium verticillioides MRC 826 growth and fumonisin B1 biosynthesis. Toxicon, 51(1), 37-44.
- The antimicrobial activity of of thymol, carvacrol, limonene, cinnamaldehyde, and eugenol were assessed. From: Di Pasqua, R., Hoskins, N., Betts, G., & Mauriello, G. (2006). Changes in membrane fatty acids composition of microbial cells induced by addiction of thymol, carvacrol, limonene, cinnamaldehyde, and eugenol in the growing media. Journal of Agricultural and Food Chemistry, 54(7), 2745-2749.
- Petitgrain essential oil and its d-limonene constituent showed antibacterial activity against a variety of tested organisms. From: Okla, M. K., Alamri, S. A., Salem, M. Z., Ali, H. M., Behiry, S. I., Nasser, R. A., … & Soufan, W. (2019). Yield, Phytochemical Constituents, and Antibacterial Activity of Essential Oils from the Leaves/Twigs, Branches, Branch Wood, and Branch Bark of Sour Orange (Citrus aurantium L.). Processes, 7(6), 363.
- Citrus bergamia and a combined action of its monoterpenes limonene and linalyl acetate aided in cancer cell death induced by cytotoxicity. From: Russo, R., Ciociaro, A., Berliocchi, L., Cassiano, M. G. V., Rombolà, L., Ragusa, S., … & Corasaniti, M. T. (2013). Implication of limonene and linalyl acetate in cytotoxicity induced by bergamot essential oil in human neuroblastoma cells. Fitoterapia, 89, 48-57.
- Limonene and cineole constituents found in cardamom demonstrate promising effects against carcinogenesis and deserve further study. From: Acharya, A., Das, I., Singh, S., & Saha, T. (2010). Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis. Recent patents on food, nutrition & agriculture, 2(2), 166-177.
- Both mandarin essential oil and limonene anti-tumor growth inhibition against lung and liver cancer. From: Manassero, C. A., Girotti, J. R., Mijailovsky, S., García de Bravo, M., & Polo, M. (2013). In vitro comparative analysis of antiproliferative activity of essential oil from mandarin peel and its principal component limonene. Natural product research, 27(16), 1475-1478.
- Citrus oils of sweet orange, grapefruit, and lemon induced apoptosis of human leukemia cancer tumor cells and limonene, decanal, octanal and citral showed strong apoptotic activity. From: Hata, T., Sakaguchi, I., Mori, M., Ikeda, N., Kato, Y., Minamino, M., & Watabe, K. (2002). Induction of apoptosis by Citrus paradisi essential oil in human leukemic (HL-60) cells. In vivo (Athens, Greece), 17(6), 553-559
- In the first study, diallyl disulfide, allyl mercaptan, and allyl methyl disulfide inhibited nitrosamine induced neoplasia tumor formation of the forestomach in mice. In the next study, diallyl disulfide, allyl mercaptan, d-limonene, and d-carvone were strong inhibitors of forestomach tumor formation related to nitrosamine carcinogenesis. From: Wattenberg, L. W., Sparnins, V. L., & Barany, G. (1989). Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Cancer research, 49(10), 2689-2692.
- Citrus aurantium and d-limonene promote gastric mucosal healing without any apparent toxic effect in rats. From: Moraes, T. M., Rozza, A. L., Kushima, H., Pellizzon, C. H., Rocha, L. R. M., & Hiruma-Lima, C. A. (2013). Healing actions of essential oils from Citrus aurantium and d-limonene in the gastric mucosa: the roles of VEGF, PCNA, and COX-2 in cell proliferation. Journal of medicinal food, 16(12), 1162-1167.
- Lemon and its constituents of limonene showed gastroprotective activity, causing mucus formation in vivo. From: Rozza, A. L., de Mello Moraes, T., Kushima, H., Tanimoto, A., Marques, M. O. M., Bauab, T. M., … & Pellizzon, C. H. (2011). Gastroprotective mechanisms of Citrus lemon (Rutaceae) essential oil and its majority compounds limonene and β-pinene: Involvement of heat-shock protein-70, vasoactive intestinal peptide, glutathione, sulfhydryl compounds, nitric oxide and prostaglandin E2. Chemico-biological interactions, 189(1-2), 82-89.
INSECTICIDAL / LARVICIDAL
- Essential oils can be efficient, and safer repellents for humans and the environment. In this mega analysis on insect repelling essential oils, Cymbopogon (lemongrass) spp., Ocimum (basil) spp. and Eucalyptus (eucalyptus) spp. are the most cited. Key constituents cited include α-pinene, limonene, citronellol, citronellal, camphor and thymol. From: Nerio, L. S., Olivero-Verbel, J., & Stashenko, E. (2010). Repellent activity of essential oils: a review. Bioresource technology, 101(1), 372-378.
- Eucalyptus, geranium, lavender, and mint showed varying degrees of repellency against the bloodsucking bug Rhodnius prolixus Stahl. The knockdown time of nymphs in minutes by constituents was 117.2 (eucalyptol), 408.7 (linalool), 474.0 (menthone), and 484.2 (limonene). While the repellent effect was lesser than that of deet, eucalyptol was 3.5 times less toxic. From: Sfara, V., Zerba, E. N., & Alzogaray, R. A. (2009). Fumigant insecticidal activity and repellent effect of five essential oils and seven monoterpenes on first-instar nymphs of Rhodnius prolixus. Journal of medical entomology, 46(3), 511-515.
- The study demonstrated Mentha spicata had larvicidal activity against Culex quinquefasciatus, Aedes aegypti, and Anopheles stephensi, with carvone, cis-carveol, and limonene constituents most effective against A. stephensi. From: Govindarajan, M., Sivakumar, R., Rajeswari, M., & Yogalakshmi, K. (2012). Chemical composition and larvicidal activity of essential oil from Mentha spicata (Linn.) against three mosquito species. Parasitology research, 110(5), 2023-2032.
- Citrus sinensis and Melaleuca quinquenervia showed varying anthelmintic activity against gastrointestinal nematodes with 1,8-cineole and limonene being active constituents. Amounts needed to by anti-parasitic may not have been safe for the host; more research is necessary. From: Gaínza, Y. A., Domingues, L. F., Perez, O. P., Rabelo, M. D., López, E. R., & de Souza Chagas, A. C. (2015). Anthelmintic activity in vitro of Citrus sinensis and Melaleuca quinquenervia essential oil from Cuba on Haemonchus contortus. Industrial Crops and Products, 76, 647-652.
SEDATIVE / ANXIOLYTIC
- Citral, limonene, and myrcene showed sedative and motor relaxant effects. From: do Vale, T. G., Furtado, E. C., Santos, J. G., & Viana, G. S. B. (2002). Central effects of citral, myrcene and limonene, constituents of essential oil chemotypes from Lippia alba (Mill.) NE Brown. Phytomedicine, 9(8), 709-714. Link: http://dx.doi.org/10.1078/094471102321621304
- Limonene aromatherapy had an anxiolytic effect on mice. From: Lima, N. G., De Sousa, D. P., Pimenta, F. C. F., Alves, M. F., De Souza, F. S., Macedo, R. O., … & de Almeida, R. N. (2013). Anxiolytic-like activity and GC–MS analysis of (R)-(+)-limonene fragrance, a natural compound found in foods and plants. Pharmacology Biochemistry and Behavior, 103(3), 450-454.
- Limonene had an antioxidant and anxiolytic effect on mice. From: de Almeida, A. A. C., de Carvalho, R. B. F., Silva, O. A., de Sousa, D. P., & de Freitas, R. M. (2014). Potential antioxidant and anxiolytic effects of (+)-limonene epoxide in mice after marble-burying test. Pharmacology Biochemistry and Behavior, 118, 69-78.
- Ingesting lemon essential oil containing components such as limonene and citral reduces both physical and psychological stress. From: Fukumoto, S., Morishita, A., Furutachi, K., Terashima, T., Nakayama, T., & Yokogoshi, H. (2008). Effect of flavour components in lemon essential oil on physical or psychological stress. Stress and Health, 24(1), 3-12.
- Limonene reduced stress related to GABA receptors. From: Zhou, W., Yoshioka, M., & Yokogoshi, H. (2009). Sub-chronic effects of s-limonene on brain neurotransmitter levels and behavior of rats. Journal of nutritional science and vitaminology, 55(4), 367-373.
TRANSDERMAL DRUG ABSORPTION
- Cardamom enhanced transdermal drug delivery by altering the barrier property of stratum corneum; the three components in cardamom oil of α-pinene, β-pinene, and α-terpineol, had a synergistic effect with 1,8-cineole and d-limonene to enhance the permeation of the drug indomethacin. From: Huang, Y. B., Fang, J. Y., Hung, C. H., WU, P. C., & TSAI, Y. H. (1999). Cyclic monoterpene extract from cardamom oil as a skin permeation enhancer for indomethacin: in vitro and in vivo studies. Biological and Pharmaceutical Bulletin, 22(6), 642-646.
- D-limonene and to a lesser degree, L-limonene, both showed enhanced skin absorption. From: Zhang, C. F., Yang, Z. L., & Luo, J. B. (2006). Effects of D-limonene and L-limonene on transdermal absorption of ligustrazine hydrochloride. Yao xue xue bao= Acta pharmaceutica Sinica, 41(8), 772-777.
- Two lemon essential oil components, limonene and perillyl, reduced the symptoms of dementia. From: Zhou, W., Fukumoto, S., & Yokogoshi, H. (2013). Components of lemon essential oil attenuate dementia induced by scopolamine. Nutritional neuroscience.
- A combination of pinene, limonene, and cineole improved mucociliary clearance. From: Dorow, P., Weiss, T. H., Felix, R., & Schmutzler, H. (1987). [Effect of a secretolytic and a combination of pinene, limonene and cineole on mucociliary clearance in patients with chronic obstructive pulmonary disease]. Arzneimittel-Forschung, 37(12), 1378-1381.
- Lemon oil had an expectorant action in rabbits, limonene and pinene were active components. From: Sheppard, E. P., & Boyd, E. M. (1970). Lemon oil as an expectorant inhalant. Pharmacological Research Communications, 2(1), 1-16.
- In this placebo-controlled, double-blind, randomized trial 246 patients with chronic bronchitis, long use (one month) of myrtol (contains alpha pinene, cineole, and d-limonene) over one month was tolerable and effective. From: Meister, R., Wittig, T., Beuscher, N., & de Mey, C. (1999). Efficacy and tolerability of Myrtol standardized in long-term treatment of chronic bronchitis. Arzneimittelforschung, 49(04), 351-358.
- In this 2 week treatment of 676 patients with chronic bronchitis, myrtol (contains alpha pinene, cineole, and d-limonene) was safe and effective. From: Matthys, H., de Mey, C., Carls, C., Ryś, A., Geib, A., & Wittig, T. (2000). Efficacy and tolerability of myrtol standardized in acute bronchitis. Arzneimittelforschung, 50(08), 700-711.
- Essential oils from C. limon, C. aurantifolia and C. limonia had a significant anti-inflammatory effect in vivo, likely related to the limonene constituent. However, C. aurantifolia, caused myelotoxicity in mice, likely related to the citral constituent. From: Amorim, J. L., Simas, D. L. R., Pinheiro, M. M. G., Moreno, D. S. A., Alviano, C. S., da Silva, A. J. R., & Fernandes, P. D. (2016). Anti-inflammatory properties and chemical characterization of the essential oils of four citrus species. PloS one, 11(4), e0153643.
- Olfactory stimulation of the aromas of grapefruit and lemon increased lipolysis and caused a suppression in body weight gain in rats. From: Niijima, A., & Nagai, K. (2003). Effect of olfactory stimulation with flavor of grapefruit oil and lemon oil on the activity of sympathetic branch in the white adipose tissue of the epididymis. Experimental Biology and Medicine, 228(10), 1190-1192.
- Helichrysum italicum essential oil and its constituents of alpha pinene and limonene demonstrated in vitro anticollagenase and antielastaste activities. From: Fraternale, D., Flamini, G., & Ascrizzi, R. (2019). In Vitro Anticollagenase and Antielastase Activities of Essential Oil of Helichrysum italicum subsp. italicum (Roth) G. Don. Journal of medicinal food.
- Carvone and limonene showed involuntary muscle spasmolytic activity in vitro. From: de Sousa, D. P., Mesquita, R. F., de Araújo Ribeiro, L. A., & de Lima, J. T. (2015). Spasmolytic activity of carvone and limonene enantiomers. Natural product communications, 10(11), 1934578X1501001120.
- Essential oil constituents with an analgesic activity are reviewed. Included are p-cymene, carvacrol, linalool, eugenol, menthol, alpha-bisabolol, cinnamaldehyde, citronellal, citronellol, citronellyl acetate, alpha-phelandrene, alpha-terpeneol, vanillin, borneol, myrtenol, pulegone, citral, thymol, limonene, nerol, anethole, nerolidol, carvone, farnesol, and beta-caryphyllene. From: Lima, T., da Nóbrega, F., de Brito, A., & de Sousa, D. (2017). Analgesic-like activity of essential oil constituents: an update. International journal of molecular sciences, 18(12), 2392.
Compiled by: Kathy Sadowski