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Review

Pharmacological applications of farnesol (C15H26O): a patent review

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Pages 227-234 | Received 30 Jan 2019, Accepted 16 Jan 2020, Published online: 23 Jan 2020

References

  • Khan R, Sultana S. Farnesol attenuates 1,2-dimethylhydrazine induced oxidative stress, inflammation and apoptotic responses in the colon of Wistar rats. Chem Biol Interact. 2011;192(3):193–200.
  • Trimble H. Practical and analytical chemistry. Philadelphia: P. Blakiston, Son & Co.,; 1885.
  • Lapczynski A, Bathia SP, Letizia CS, et al. Fragrance material review on farnesol. Food Chem Toxicol. 2008;46(11):149–156.
  • Qamar W, Sultana S. Farnesol ameliorates massive inflammation, oxidative stress and lung injury induced by intratracheal instillation of cigarette smoke extract in rats: an initial step in lung chemoprevention. Chem Biol Interact. 2008;176(2–3):79–87.
  • Yazlovitskaya EM, Melnykovych G. Selective farnesol toxicity and translocation of protein kinase C in neoplastic HeLa-S3K and non-neoplastic CF-3 cells. Cancer Lett. 1995;88:179–183.
  • Shahnouri M, Abouhosseini Tabari M, Araghi A. Neuropharmacological properties of farnesol in Murine model. Iran J Vet Res. 2016;17(4):259–264.
  • Silva JC, Alcantara LFM, Soares JM, et al. Docking, characterization and investigation of β-cyclodextrin complexed with farnesol, an acyclic sesquiterpene alcohol, produces orofacial antinociceptive profile in experimental protocols. Process Biochem. 2017;62:193–204.
  • Santhanasabapathy R, Sudhandiran G. Farnesol attenuates lipopolysaccharide-induced neurodegeneration in Swiss albino mice by regulating intrinsic apoptotic cascade. Brain Res. 2015;1620:42–56.
  • Luft UC, Bychkov R, Gollasch M, et al. Farnesol blocks the L-type Ca2+ channel by targeting the alpha 1C subunit. Arterioscl Throm Vas. 1999;19:959–966.
  • Roullet JB, Luft UC, Xue H, et al. Farnesol inhibits L-type Ca2+ channels in vascular smooth muscle cells. J Biol Chem. 1997;272:32240–32246.
  • Souza DS, Envolvimento dos canais para cálcio tipo-L na resposta cardiodepressora do farnesol em coração de rato, Dissertação (Mestrado em Ciências Fisiológicas). Universidade Federal de Sergipe, São Cristovão-SE, (2016).
  • Buchbauer G, Ilic A. Biological activities of selected mono- and sesquiterpenes: possible uses in medicine. In: Ramawat K, Mérillon JM, editors. Natural Products. 2nd ed. Berlin, Heidelberg: Springer; 2002. p. 13–43. Der Marderosian, A.; Beutler, J.A. The Review of Natural Products, Facts and Comparisons; Seattle, WA, USA.
  • Shin J, Jo A, Lee Y, inventor; Johns Hopkins University, et al.. Methods for preventing or treating parkinson’s disease by the farnesylation of paris, US WO2017161155; 2015.
  • Doi K, Nakayama H, inventor; Senju Pharmaceutical Co. Ltd., et al. Composiciones oftalmicas que contienen terpenoides para lentes de contacto, ES 2247711; 2006.
  • Myers CE, Trepel J, inventor; The United States of America as represented by Department of Health and Human Services, et al.. Monoterpenes, sesquiterpenes and diterpenes as cancer therapy, US 5602184, 1997.
  • Delmondes GA, Bezerra DS, da Cunha Lins G, et al. Toxicological and pharmacologic effects of farnesol (C15H26O): A descriptive systematic review. Food Chem Toxicol. 2019;129:169–200.
  • Zhihong N, Juanchan H, inventor; Boke Pharmaceutical Co. Ltd., et al. Composition capable dispelling tragomaschalia, CN 101336984; 2009.
  • Koenig DW, inventor; Kimberly-Clark Worldwide, Inc. Artigo de cuidado pessoal e método para inibir fixação de levedura à pele, BR PI 0310045-6 A2; 2003.
  • Gerard T, inventor; Transbiotech. Composition biocide et/ou biostatique et ses applications, FR 2697133; 1994.
  • DSCM C-B, Riello GB, Vasconcelos DC, et al. Farnesol increases the susceptibility of Burkholderia pseudomallei biofilm to antimicrobials used to treat melioidosis. J Appl Microbiol. 2016;120(3):600–606.
  • Fernandes RA, Monteiro DR, Arias LS, et al. Biofilm formation by Candida albicans and Streptococcus mutans in the presence of farnesol: a quantitative evaluation. Biofouling. 2016;32(3):329–338.
  • Kovács R, Bozó A, Gesztelyi R, et al. Effect of caspofungin and micafungin in combination with farnesol against Candida parapsilosis biofilms. Int J Antimicrob Agents. 2016;47(4):304–310.
  • Katragkou A, McCarthy M, Alexander EL, et al. In vitro interactions between farnesol and fluconazole, amphotericin b or micafungin against Candida albicans biofilms. J Antimicrob Chemother. 2015;70(2):470–478.
  • Brilhante RSN, de Lima RA. Histoplasma capsulatum in planktonic and biofilm forms: in vitro susceptibility to amphotericin B, itraconazole and farnesol. J Med Microbiol. 2015;64(4):394–399.
  • Horev B, Klein MI, Hwang G, et al. pH-activated nanoparticles for controlled topical delivery of farnesol to disrupt oral biofilm virulence. ACS Nano. 2015;9(3):2390–2404.
  • Mogen AB, Chen F, Ahn SJ, et al. Pluronics-formulated farnesol promotes efficient killing and demonstrates novel interactions with Streptococcus mutans biofilms. PLoS One. 2015;10(7):1–18.
  • Abdel-Rhman SH, El-Mahdy AM. Effect of tyrosol and farnesol on virulence and antibiotic resistance of clinical isolates of Pseudomonas aeruginosa. Biomed Res Int. 2015;2015:456–463.
  • Bhattacharyya S, Agrawal A, Knabe C, et al. Sol-gel silica controlled release thin films for the inhibition of methicillin-resistant Staphylococcus aureus. Biomaterials. 2014;35(1):509–517.
  • Wang X, Wang Y, Zhou Y, et al. Farnesol induces apoptosis-like cell death in the pathogenic fungus Aspergillus flavus. Mycologia. 2014;106(5):881–888.
  • Brilhante RSN, de Lima RA, Caetano EP, et al. Effect of farnesol on growth, ergosterol biosynthesis, and cell permeability in Coccidioides posadasii. Antimicrob Agents Chemother. 2013;57(5):2167–2170.
  • Cordeiro RA, Nogueira GC, Brilhante RS, et al. Farnesol inhibits in vitro growth of the Cryptococcus neoformans species complex with no significant changes in virulence-related exoenzymes. Vet Microbiol. 2012;159(3–4):375–380.
  • Cerca N, Gomes F, Pereira S, et al. Confocal laser scanning microscopy analysis of S. epidermidis biofilms exposed to farnesol, vancomycin and rifampicin. BMC Res Notes. 2012;5(1):244–251.
  • Gomes F, Leite B, Azeredo J, et al. Farnesol as antibiotics adjuvant in Staphylococcus epidermidis control in vitro. Am J Med Sci. 2011;341(3):191–195.
  • Gonçalves O, Pereira R, Gonçalves F, et al. Evaluation of the mutagenicity of sesquiterpenic compounds and their influence on the susceptibility towards antibiotics of two clinically relevant bacterial strains. Mutat Res Genet Toxicol Environ Mutagen. 2011;723(1):18–25.
  • Kaneko M, Togashi N, Hamashima H, et al. Effect of farnesol on mevalonate pathway of Staphylococcus aureus. J Antibiot (Tokyo). 2011;64(8):547–549.
  • Gomes F, Texeira P, Cerca N, et al. Effect of farnesol on structure and composition of Staphylococcus epidermidis biofilm matrix. Curr Microbiol. 2011;63(4):354–359.
  • Liu P, Luo L, Guo J, et al. Farnesol induces apoptosis and oxidative stress in the fungal pathogen Penicillium expansum. Mycologia. 2010;102(2):311–318.
  • Décanis N, Savignac K, Rouabhia M, et al. Farnesol promotes epithelial cell defense against Candida albicans through Toll-like receptor 2 expression, interleukin-6 and human β-defensin 2 production. Cytokine. 2009;45(2):132–140.
  • Gomes FI, Teixeira P, Azeredo J, et al. Effect of farnesol on planktonic and biofilm cells of Staphylococcus epidermidis. Curr Microbiol. 2009;59(2):118–122.
  • Derengowski LS, De-Souza-Silva C, et al. Antimicrobial effect of farnesol, a Candida albicans quorum sensing molecule, on Paracoccidioides brasiliensis growth and morphogenesis. Ann Clin Microbiol Antimicrob. 2009;8(1):13.
  • Unnanuntana A, Bonsignore L, Braz SV, et al. The Effects of Farnesol on Staphylococcus aureus Biofilms and Osteoblasts. J Bone Jt Surg. 2009;91(11):2683–2692.
  • Hisajima T, Maruyama N, Tanabe Y, et al. Protective effects of farnesol against oral candidiasis in mice. Microbiol Immunol. 2008;52(7):237–333.
  • Holley RA, Patel D. Improvement of shelflife and safety of perishable foods by plant essential oils and smoke antimicrobials. Food Microbiol. 2005;22:273–292.
  • Oladimeji FA, Orafidiya LO. Physical properties and antimicrobial activities of leaf essential oils of Lippia multiflora Moldenke. Int J Aromather. 2004;14:162–168.
  • Rougereau A, Rougereau-Person O, inventor; Conley Rose, P.C. Novel medicines based on sesquiterpene mixtures, US 20040072915; 2004.
  • Myers CE, Trepel J, inventor. The United States of America as represented by Department of Health and Human Services, et al.. Use of monoterpenes, sesquiterpernes and diterpernes for the treatment of cancer, US WO1994020080, 1994.
  • Lee JH, Kim C, Kim SH, et al. Farnesol inhibits tumor growth and enhances the anticancer effects of bortezomib in multiple myeloma xenograft mouse model through the modulation of STAT3 signaling pathway. Cancer Lett. 2015;360(2):280–293.
  • Joo JH, Ueda E, Bortner CD, et al. Farnesol activates the intrinsic pathway of apoptosis and the ATF4-ATF3-CHOP cascade of ER stress in human T lymphoblastic leukemia Molt4 cells. Biochem Pharmacol. 2015;97(3):256–268.
  • Park JS, Kwon JK, Kim HR, et al. Farnesol induces apoptosis of DU145 prostate cancer cells through the PI3K/Akt and MAPK pathways. Int J Mol Med. 2014;33(5):1169–1176.
  • Journe F, Laurent G,Chaboteaux C, et al. Farnesol, a mevalonate pathway intermediate, stimulates MCF-7 breast cancer cell growth through farnesoid-X-receptor-mediated estrogen receptor activation. Breast Cancer Res Treat. 2008;107(1):49–61.
  • Au-Yeung KK, Liu PL,Chan C, et al. Herbal isoprenols induce apoptosis in human colon cancer cells through transcriptional activation of PPARgamma. Cancer Invest. 2008;26(7):708–717.
  • Wiseman DA, Werner SR, Crowell PL, et al. Cell cycle arrest by the isoprenoids perillyl alcohol, geraniol, and Farnesol is mediated by p21 Cip1 and p27 Kip1 in human pancreatic adenocarcinoma cells. J Pharmacol Exp Ther. 2007;320(3):1163–1170.
  • Voziyan PA, Haug JS, Melnykovych G, et al. Mechanism of farnesol cytotoxicity: futher evidence for the role of PKC-dependent signal transduction in Farnesol-induced apoptotic cell death. Biochem Biophys Res Commun. 1995;22(2):479–486.
  • Haug JS, Goldner CM, Yazlovitskaya EM, et al. Directed cell killing (apoptosis) in human lymphoblastoid cells incubated in the presence of farnesol: effect of phosphatidylcholine. Biochim Biophys Acta. 1994;1223:133–140.
  • Adany I, Yazlovitskaya EM, Haug JS, et al. Differences in sensitivity to farnesol toxicity between neoplastically-and non-neoplastically-derived cells in culture. Cancer Lett. 1994;79(2):175–179.
  • Voziyan PA, Goldner CM, Melnykovych G, et al. Farnesol inhibits phosphatidylcholine biosynthesis in cultured cells by decreasing cholinephosphotransferase activity. Biochem J. 1993;295(3):757–762.
  • Melnykovych G, Haug JS. Growth inhibition of leukemia cell i_/ne cem-c1 by farnesol: effects of phosphatidylcholine and diacylglycerol. Biochem Biophys Res Commun. 1992;186(1):543–548.
  • Jo DG, Park JS, inventor; Research Business Foundation Sungkyunkwan University, et al. Composition containing compound down-regulating bace1 protein expression for preventing or treating degenerative brain disease. patent KR 1020150008802; 2015.
  • Raz N, Eyal AM, inventor; Buzzelet Development and Technologies Ltd. Terpene-enriched cannabinoid composition and method of treatment. US WO2019034936; 2018.
  • Zamponi GW, inventor; NeuroMed Technologies, Inc. Farnesol-related calcium channel blockers. US 6267945; 2001.
  • Roullet JBO, Crabbe-Junior JC, inventor; Oregon Health & Science University, et al. Compositions and methods for treatment of neurological symptoms associated with alcohol-withdrawal and for convulsive seizure. US 20080286209; 2008.
  • Lab Meram, inventor. Pharmaceutical composition and mental illness treatment pack. GB 1279686; 1972.
  • Sung MJ, Sung KS, inventor; Korea Food Research Institute, et al. Pharmaceutical composition including trans-farnesol as active ingredient for controlling angiogenesis, KR 1020140083522; 2014.
  • Lagace TA, Ridgway ND. Induction of apoptosis by lipophilic activators of CTP: phosphocholinecytidylyltransferase α (CCTα). Biochem J. 2005;392(3):449–456.
  • Khan R, Sultana S. Farnesol attenuates 1,2-dimethylhydrazine induced oxidative stress, inflammation and apoptotic responses in the colon of Wistar rats. Chem Biol Interact. 2011;192:193–200.
  • Chaudhary SC, Alam MS. Chemopreventive effect of farnesol on DMBA/TPA-induced skin tumorigenesis: involvement of inflammation, Ras-ERK pathway and apoptosis. Life Sci. 2009;85(5–6):196–205.
  • Marcuzzi A, Pontillo A, Leo LD, et al. Natural isoprenoids are able to reduce inflammation in a mouse model of mevalonate kinase deficiency. Pediatr Res. 2008;64(2):177–182.
  • Robinson LR, inventor. Composição de cuidado com a pele. BR PI 0009893-0 A2; 2000.
  • Bissett DL, inventor. Método para regularizar a condição do tecido ceratinoso em mamíferos. BR PI 0009892-2 A2; 2000.
  • Edwards RM, Clements JM, inventor, Heptagen Limited, et al. Combinations for the treatment of immunoproliferative skin disorders such as psoriasis. GB WO2005102296; 2005.
  • Jahangir T, Khan TH, Prasad L, et al. Alleviation of free radical mediated oxidative and genotoxic effects of cadmium by farnesol in Swiss albino mice. Redox Rep. 2005;10:303–310.
  • Jahangir T, Khan TH. Farnesol prevents Fe-NTA-mediated renal oxidative stress and early tumour promotion markers in rats. Hum Exp Toxicol. 2006;25:235–242.
  • Jahangir T, Sultana S. Benzo(a)pyrene-induced genotoxicity: attenuation by farnesol in a mouse model. J Enzyme Inhib Med Chem. 2008;23:888–894.
  • Khan R, Sultana S. Farnesol attenuates 1,2-dimethylhydrazine induced oxidative stress, inflammation and apoptotic responses in the colon of Wistar rats. Chem-Biol Interact. 2011;192:193–200.
  • Lateef A, Rehman MU, Tahir M, et al. Farnesol protects against intratracheally instilled cigarette smoke extract-induced histological alterations and oxidative stress in prostate of wistar rats. Toxicol Int. 2013;20:35–42.
  • Qamar W, Khan AQ, Khan R, et al. Benzo(a)pyrene-induced pulmonary inflammation, edema, surfactant dysfunction, and injuries in rats: alleviation by farnesol. Exp Lung Res. 2012;38:19–27.
  • Qamar W, Sultana S. Farnesol ameliorates massive inflammation, oxidative stress and lung injury induced by intratracheal instillation of cigarette smoke extract in rats: an initial step in lung chemoprevention. Chem-Biol Interact. 2008;176:79–87.
  • Buchli L. Radicais livres e antioxidantes. C&T. 2002;14(2):54–57.

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