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A Particular Focus on P-Cymene

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A Particular Focus on P-Cymene materials Review Update on Monoterpenes as Antimicrobial Agents: A Particular Focus on p-Cymene Anna Marchese 1, Carla Renata Arciola 2,3, Ramona Barbieri 1, Ana Sanches Silva 4,5, Seyed Fazel Nabavi 6, Arold Jorel Tsetegho Sokeng 7, Morteza Izadi 8, Nematollah Jonaidi Jafari 8, Ipek Suntar 9, Maria Daglia 7,* ID and Seyed Mohammad Nabavi 6,* 1 Sezione di Microbiologia DISC-IRCCS San Martino-IST University of Genoa, 16132 Genoa, Italy; [email protected] (A.M.); [email protected] (R.B.) 2 Research Unit on Implant Infections, Rizzoli Orthopaedic Institute, via di Barbiano 1/10, 40136 Bologna, Italy; [email protected] 3 Department of Experimental, Diagnostic and Specialty Medicine (DIMES), University of Bologna, Via San Giacomo 14, 40126 Bologna, Italy 4 National Institute for Agricultural and Veterinary Research (INIAV), I.P., Vairão, 4480 Vila do Conde, Portugal; [email protected] 5 Center for Study in Animal Science (CECA), ICETA, University of Oporto, 4051-401 Oporto, Portugal 6 Applied Biotechnology Research Center, Baqiyatallah University of Medical Sciences, Tehran 19395-5487, Iran; [email protected] 7 Department of Drug Sciences, Medicinal Chemistry and Pharmaceutical Technology Section, University of Pavia, 27100 Pavia, Italy; [email protected] 8 Health Research Center, Baqiyatallah University of Medical Sciences, Tehran 19395-5487, Iran; [email protected] (M.I.); [email protected] (N.J.J.) 9 Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Etiler, Ankara 06330, Turkey; [email protected] * Correspondence: [email protected] (M.D.); [email protected] (S.M.N.); Tel./Fax: +98-21-88617712 (M.D.); +39-0382-987388 (S.M.N.) Received: 25 July 2017; Accepted: 11 August 2017; Published: 15 August 2017 Abstract: p-Cymene [1-methyl-4-(1-methylethyl)-benzene] is a monoterpene found in over 100 plant species used for medicine and food purposes. It shows a range of biological activity including antioxidant, anti-inflammatory, antinociceptive, anxiolytic, anticancer and antimicrobial effects. This last property has been widely investigated due to the urgent need for new substances with antimicrobial properties, to be used to treat communicable diseases whose diffusion in developed countries has been facilitated by globalization and the evolution of antimicrobial resistance. This review summarizes available scientific data, as reported by the most recent studies describing the antimicrobial activity of p-cymene either alone, or as the main component of plant extracts, as well as addressing the mechanisms of action of cymenes as antimicrobial agents. While p-cymene is one of the major constituents of extracts and essential oils used in traditional medicines as antimicrobial agents, but considering the limited data on its in vivo efficacy and safety, further studies are required to reach a definitive recommendation on the use and beneficial effects of p-cymene in human healthcare and in biomedical applications as a promising candidate to functionalize biomaterials and nanomaterials. Keywords: antibacterial; antimicrobial; cymenes; monoterpenes 1. Introduction Plant extracts and their secondary metabolites are rich sources of antimicrobial substances, including coumarins and psoralens, acetylenes, flavonoid and non-flavonoid polyphenols, and terpenes [1–5]. Monoterpenes (i.e., eucalyptol, borneol, camphor, bornylacetate, carvacrol, Materials 2017, 10, 947; doi:10.3390/ma10080947 www.mdpi.com/journal/materials Materials 2017, 10, 947 2 of 15 1. Introduction Plant extracts and their secondary metabolites are rich sources of antimicrobial substances, Materialsincluding2017 coumarins, 10, 947 and psoralens, acetylenes, flavonoid and non-flavonoid polyphenols,2 ofand 15 terpenes [1–5]. Monoterpenes (i.e., eucalyptol, borneol, camphor, bornylacetate, carvacrol, (−)- (menthol,−)-menthol, γ-terpinene,γ-terpinene, (+)-α-pinene, (+)-α-pinene, (−)-β-pinene, (−)-β-pinene, and p-cymene) and p-cymene) are the most are important the most constituents important constituentsof essential oils of essentialproduced oils through produced liquid through extraction liquid and extraction steam distillation and steam of edible distillation and medicinal of edible andplants medicinal [1]. p-Cymene plants [1-methyl-4-(1-methylethyl)-benz [1]. p-Cymene [1-methyl-4-(1-methylethyl)-benzene]ene] is an alkyl-substituted is aromatic an alkyl-substituted hydrocarbon aromaticfound in hydrocarbonnature, whose found benzene in nature, ring features whose benzene the substitution ring features of a the methyl substitution and an of isopropyl a methyl group, and an isopropyland which group, is considered and which to isbe considered the most toimport be theant most monoterpene important monoterpenecompound occurring compound in occurringaromatic inplants, aromatic such plants,as thyme such and as thymeoregano. and p-Cymene oregano. is p-Cymene found in ismore found than in more100 plant than species, 100 plant including species, includingmany belonging many belonging to Thymus, to Thymus, Origanum, Origanum, OcimunOcimun (Lamiaceae),(Lamiaceae), EucalyptusEucalyptus (Mirtaceae),(Mirtaceae), Protium (Burseraceae), and Artemisia (Asteraceae) genus [[6].6]. This This comp compoundound shows a variety of biological activities which include antioxidant, antinociceptive,antinociceptive, anti-inflammatory,anti-inflammatory, anxiolytic, anticancer and antimicrobial activities.activities. In In fact, fact, recent recentin vivoin vivoinvestigations investigations performed performed on experimental on experimental animal animal model systemsmodel systems (adult male(adult Swiss male mice), Swiss showed mice), showed that p-cymene that p-cymene increases increases the activity the of activity antioxidant of antioxidant enzymes, reducingenzymes, oxidativereducing stressoxidative [7,8]. stress In addition, [7,8]. In it addition, shows anti-inflammatory it shows anti-inflammatory activity, being activity, able to being modulate able cytokineto modulate production cytokine (tumor production necrosis (tumor factor- necrosisα-TNF- αfactor-, interleukin-1α-TNF-αβ, interleukin-1-IL-1β, interleukin-6-IL-6)β-IL-1β, interleukin-in vitro (murine6-IL-6) in macrophage-like vitro (murine macrophage-like cell line RW 264.7) cell and linein RW vivo 264.7)(Female and C57BL/6) in vivo (Female by inhibiting C57BL/6) nuclear by factor-inhibitingκB (NF-nuclearκB) andfactor- mitogen-activatedκB (NF-κB) and protein mitogen-activated kinase (MAPK) protein signaling kinase pathways (MAPK) involved signaling in synthesispathways ofinvolved pro-inflammatory in synthesis cytokinesof pro-inflammatory [9]. The anti-inflammatory cytokines [9]. The activityanti-inflammatory of p-cymene activity at least of partlyp-cymene justifies at least its antinociceptive partly justifies activity,its antinociceptive as recorded activity, in several asin recorded vivo studies in several performed in vivo on murinestudies modelperformed systems on murine [8,10,11 model]. Moreover, system recents [8,10,11]. investigations Moreover, report recent the investigations antitumor activity report of p-cymenethe antitumor and metalactivity p-cymene of p-cymene complexes and suchmetal as p-cymene rutenium (II)-comple andxes osmium such (II)-p-cymeneas rutenium (II)- complexes, and osmium which inhibit(II)-p- tumorcymene proliferation complexes, throughwhich inhibit an antiangiogenic tumor proliferation mechanism, through cancer an antiangiogenic cell cytotoxicity, mechanism, and anti-adhesion cancer activitycell cytotoxicity, [12–14]. p-Cymene and anti-adhesion is the main activity antimicrobial [12–14]. compound p-Cymene in is thyme,the main and antimicrobial a large body ofcompound evidence suggestsin thyme, that and this a monoterpenelarge body of possesses evidence antibacterial, suggests that antiviral this monoterpene and antifungal possesses activities. antibacterial, This review reportsantiviral the and available antifungal data activities. on the mechanismsThis review reports of action the of available cymenes data and on summarizes the mechanisms major of studies action describingof cymenes their and antimicrobialsummarizes major activity, studies both alonedescribing or as their main antimicrobial components ofactivity, plant extracts, both alone from or the as pastmain five components years. of plant extracts, from the past five years. 2. Chemistry p-Cymene (also known as 4-isopropyltoluene,4-isopropyltoluene, 1-isopropyl-4methylbenzene or or 1-methyl-4- isopropylbenzene) isis a naturally occurring compound compound,, although it has two two further further geometric geometric isomers, isomers, m-cymene (with meta-substituted alkyl groups) and o-cymene (with ortho-substituted alkyl groups) groups) which dodo notnot occuroccur naturallynaturally [5[5,15,15].]. p-Cymenep-Cymene isis relatedrelated toto thethe monoterpenes.monoterpenes. MonoterpenesMonoterpenes themselves belong to the “terpenes”, a larger class of organic compounds, which are the most representative componentscomponents ofof essentialessential oils [[8,16].8,16]. Figure 11 showsshows thethe chemicalchemical structurestructure ofof p-cymene, indicating the benzene ring with methyl and isopropylisopropyl substitutions. Some of the physical properties of this molecule are compiled inin TableTable1 1.. Figure 1. Chemical structure of p-cymene [[17].17]. Materials 2017, 10, 947 3 of 15 Table 1. Some physical properties of p-cymene [17]. Physical Property Value Molecular Weight 134.22 Boiling Point
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