D-Limonene modulates T lymphocyte activity and viability

Cellular Immunology

Volumn 279, Issue 1, 2012, Pages 30-41

  Lappas, Courtney M ^a   Lappas, Nicholas T ^b  

^a LEBANON VALLEY COLLEGE   (United States)

^b GEORGE WASHINGTON UNIVERSITY   (United States)

Author keywords

D Limonene; Immuntoxicology; T lymphocytes

Indexed keywords

CD40 LIGAND; CD69 ANTIGEN; GAMMA INTERFERON; INTERLEUKIN 13; INTERLEUKIN 2; INTERLEUKIN 2 RECEPTOR ALPHA; INTERLEUKIN 4; LIMONENE; LIMONENE 1,2 DIOL; PERILLIC ACID; TERPENOID DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CD3+ T LYMPHOCYTE; CD4+ T LYMPHOCYTE; CD8+ T LYMPHOCYTE; CELL DEATH; CELL ISOLATION; CELL TYPE; CELL VIABILITY; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG EFFECT; DRUG INHIBITION; ENZYME LINKED IMMUNOSORBENT ASSAY; FEMALE; FLOW CYTOMETRY; IMMUNOMODULATION; LYMPHOCYTE PROLIFERATION; METABOLITE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; RECEPTOR UPREGULATION; SPLEEN CELL; T LYMPHOCYTE ACTIVATION;

ANIMALS; ANTICARCINOGENIC AGENTS; ANTIGENS, CD; ANTIGENS, CD3; ANTIGENS, DIFFERENTIATION, T-LYMPHOCYTE; CD4-POSITIVE T-LYMPHOCYTES; CD40 LIGAND; CD8-POSITIVE T-LYMPHOCYTES; CELL PROLIFERATION; CELL SURVIVAL; CELLS, CULTURED; CYCLOHEXENES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME-LINKED IMMUNOSORBENT ASSAY; FEMALE; FLOW CYTOMETRY; INTERFERON-GAMMA; INTERLEUKIN-13; INTERLEUKIN-2; INTERLEUKIN-2 RECEPTOR ALPHA SUBUNIT; INTERLEUKIN-4; LECTINS, C-TYPE; MICE; MICE, INBRED C57BL; MONOTERPENES; TERPENES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84871643991     PISSN: 00088749     EISSN: 10902163     Source Type: Journal    
DOI: 10.1016/j.cellimm.2012.09.002     Document Type: Article

References (31)

1. Limonene monograph. Cri. Rev. Food Sci. Nutr. 1999, 39:260-265.
2. Igimi H., Hisatsugu T., Nishimura M. The use of d-limonene preparation as a dissolving agent of gallstones. Am. J. Dig. Dis. 1976, 21:926-939.
3. J. Wilkins Jr., Method for treating gastrointestinal disorder, 2002, (US Patent 642045).
4. Elegbede J.A., Elson C.E., Qureshi A., Tanner M.A., Gould M.N. Inhibition of DMBA-induced mammary cancer by the monoterpene d-limonene. Carcinogenesis 1984, 5:661-664.
5. Maltzman T.H., Hurt L.M., Elson C.E., Tanner M.A., Gould M.N. The prevention of nitrosomethylurea-induced mammary tumors by d-limonene and orange oil. Carcinogenesis 1989, 10:781-783.
6. Wattenberg L.W., Sparnins V.L., Barany G. Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Cancer Res. 1989, 49:2689-2692.
7. Wattenberg L.W., Coccia J.B. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone carcinogenesis in mice by d-limonene and citrus fruit oils. Carcinogenesis 1991, 12:115-117.
8. Crowell P.L., Siar A.A., Burke Y.D. Antitumorigenic effects of limonene and perillyl alcohol against pancreatic and breast cancer. Adv. Exp. Med. Biol. 1996, 401:131-136.
9. Vigushin D.M., Poon G.K., Boddy A., English J., Halbert G.W., Pagonis C., Jarman M., Coombes R.C. 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, 42:111-117.
10. Bailey H.H., Levy D., Harris L.S., Schink J.C., Foss F., Beatty P., Wadler S. A phase II trial of daily perillyl alcohol in patients with advanced ovarian cancer: Eastern Cooperative Oncology Group Study E2E96. Gynecol. Oncol. 2002, 85:464-468.
11. Meadows S.M., Mulkerin D., Berlin J., Bailey H., Kolesar J., Warren D., Thomas J.P. Phase II trial of perillyl alcohol in patients with metastatic colorectal cancer. Int. J. Gastrointest. Cancer 2002, 32:125-128.
12. Hamada M., Uezu K., Matsushita J., Yamamoto S., Kishino Y. Distribution and immune responses resulting from oral administration of d-limonene in rats. J. Nutr. Sci. Vitaminol. (Tokyo) 2002, 48:155-160.
13. Raphael T.J., Kuttan G. Immunomodulatory activity of naturally occurring monoterpenes carvone, limonene, and perillic acid. Immunopharmacol. Immunotoxicol. 2003, 25:285-294.
14. Evans D.L., Miller D.M., Jacobsen K.L., Bush P.B. Modulation of immune responses in mice by d-limonene. J. Toxicol. Environ. Health 1987, 20:51-66.
15. Del Toro-Arreola S., Flores-Torales E., Torres-Lozano C., Del Toro-Arreola A., Tostado-Pelayo K., Guadalupe Ramirez-Duenas M., Daneri-Navarro A. Effect of d-limonene on immune response in BALB/c mice with lymphoma. Int. Immunopharmacol. 2005, 5:829-838.
16. Schulz S., Reinhold D., Schmidt H., Ansorge S., Hollt V. Perillic acid inhibits Ras/MAP kinase-driven IL-2 production in human T lymphocytes. Biochem. Biophys. Res. Commun. 1997, 241:720-725.
17. Yoon W.J., Lee N.H., Hyun C.G. Limonene suppresses lipopolysaccharide-induced production of nitric oxide, prostaglandin E2, and pro-inflammatory cytokines in RAW 264.7 macrophages. J. Oleo. Sci. 2010, 59:415-421.
18. Crowell P.L., Elson C.E., Bailey H.H., Elegbede A., Haag J.D., Gould M.N. Human metabolism of the experimental cancer therapeutic agent d-limonene. Cancer Chemother. Pharmacol. 1994, 35:31-37.
19. Poon G.K., Vigushin D., Griggs L.J., Rowlands M.G., Coombes R.C., Jarman M. Identification and characterization of limonene metabolites in patients with advanced cancer by liquid chromatography/mass spectrometry. Drug Metab. Dispos. 1996, 24:565-571.
20. National Toxicology Program, Toxicology and Carcinogenesis Studies of d-Limonene in F344/N Rats and B6C3F1 Mice, NIH Publication Number 90-2802, US Government Printing Office, 2007.
21. Turner S.D., Tinwell H., Piegorsch W., Schmezer P., Ashby J. The male rat carcinogens limonene and sodium saccharin are not mutagenic to male Big Blue rats. Mutagenesis 2001, 16:329-332.
22. Park H.M., Lee J.H., Yaoyao J., Jun H.J., Lee S.J. Limonene, a natural cyclic terpene, is an agonistic ligand for adenosine A(2A) receptors. Biochem. Biophys. Res. Commun. 2011, 404:345-348.
23. The Unites States Code of Federal Regulations, Title 21, Part 182.60, 2011.
24. World Health Organization, International Agency for Research on Cancer, d-Limonene. IARC Monogr. Eval. Carcinog. Risk Chem. Hum. 1999, 73:307-327.
25. Whysner J., Williams G.M. d-Limonene mechanistic data and risk assessment: absolute species-specific cytotoxicity, enhanced cell proliferation, and tumor promotion. Pharmacol. Ther. 1996, 71:127-136.
26. Igimi H., Watanabe D., Yamamoto F., Asakawa S., Toraishi K., Shimura H. A useful cholesterol solvent for medical dissolution of gallstones. Gastroenterol. Jpn. 1992, 27:536-545.
27. Mills J.J., Chari R.S., Boyer I.J., Gould M.N., Jirtle R.L. Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol. Cancer Res. 1995, 55:979-983.
28. d-Limonene Monograph 1994, Flavor and Extract Manufacturers' Association, Flavor and Extract Manufacturers' Association.
29. Crowell P.L., Lin S., Vedejs E., Gould M.N. Identification of metabolites of the antitumor agent d-limonene capable of inhibiting protein isoprenylation and cell growth. Cancer Chemother. Pharmacol. 1992, 31:205-212.
30. Igimi H., Nishimura M., Kodama R., Ide H. Studies on the metabolism of d-limonene (p-mentha-1,8-diene). I. The absorption, distribution and excretion of d-limonene in rats. Xenobiotica 1974, 4:77-84.
31. Kodama R., Yano T., Furukawa K., Noda K., Ide H. 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, 6:377-389.