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The Dual Antioxidant/Prooxidant Effect of Eugenol and Its Action in Cancer Development and Treatment

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The Dual Antioxidant/Prooxidant Effect of Eugenol and Its Action in Cancer Development and Treatment nutrients Review The Dual Antioxidant/Prooxidant Effect of Eugenol and Its Action in Cancer Development and Treatment Daniel Pereira Bezerra 1 ID , Gardenia Carmen Gadelha Militão 2, Mayara Castro de Morais 3 and Damião Pergentino de Sousa 3,* ID 1 Instituto Gonçalo Moniz, Fundação Oswaldo Cruz (IGM-FIOCRUZ/BA), Salvador 40296-710, Bahia, Brazil; [email protected] 2 Departamento de Fisiologia, Universidade Federal de Pernambuco, Recife 50670-901, Pernambuco, Brazil; [email protected] 3 Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, João Pessoa 58051-970, Paraíba, Brazil; [email protected] * Correspondence: [email protected]; Tel.: +55-83-3209-8417 Received: 8 November 2017; Accepted: 12 December 2017; Published: 17 December 2017 Abstract: The formation of reactive oxygen species (ROS) during metabolism is a normal process usually compensated for by the antioxidant defense system of an organism. However, ROS can cause oxidative damage and have been proposed to be the main cause of age-related clinical complications and diseases such as cancer. In recent decades, the relationship between diet and cancer has been more studied, especially with foods containing antioxidant compounds. Eugenol is a natural compound widely found in many aromatic plant species, spices and foods and is used in cosmetics and pharmaceutical products. Eugenol has a dual effect on oxidative stress, which can action as an antioxidant or prooxidant agent. In addition, it has anti-carcinogenic, cytotoxic and antitumor properties. Considering the importance of eugenol in the area of food and human health, in this review, we discuss the role of eugenol on redox status and its potential use in the treatment and prevention of cancer. Keywords: reactive oxygen species; metabolism; antitumor activity; antioxidant activity; phenylpropanoid; natural products; essential oils; clove; Syzygium aromaticum 1. Introduction Reactive oxygen species (ROS) are a heterogeneous group of molecules that are, along with endogenous antioxidants, ubiquitously present in all organisms. They are implicated in various diseases including malignant transformations [1]. The term “oxidative stress” refers to an imbalance in which pro-oxidants overwhelm the capacity of antioxidant defense systems [2]; it has been shown to contribute to the development of some types of cancer [3]. The report of anticancer potential of aromatic compounds found in foods and plants have increased in the recent decades [4–8] and there are advanced studies of mechanisms of action and clinical approaches in progress. This chemical class of natural products show interesting potential as health promoting agents and, consequently, with application to improving the quality of life. These include the polyphenols that are important components of human diet. Interestingly, some of these compounds may act as either antioxidants or pro-oxidants to exert protective effects against cancer [9–11]. Eugenol (4-allyl-2-methoxyphenol) (Figure1) is an aromatic phenylpropanoid phenol contained in clove (Syzygium aromaticum, Myrtaceae), which is well-known for its culinary uses. Eugenol also occurs in soybeans, mung beans [12], coffee [13], bananas [14] and in herbs such as nutmeg (Myristica fragrans, Myristicaceae), cinnamon (Cinnamomum verum, Lauraceae) and basil (Ocimum basilicum, Lamiaceae); however, Syzygium aromaticum can be considered the principal natural Nutrients 2017, 9, 1367; doi:10.3390/nu9121367 www.mdpi.com/journal/nutrients Nutrients 2017, 9, 1367 2 of 15 NutrientsNutrients 2017 2017, 9,, 91367, 1367 2 of2 of 14 14 naturalnatural source source of of this this compound compound (45% (45% or or 90% 90% of of the the total total oil) oil) [15]. [15]. Clove Clove has has been been used used for for a along long source of this compound (45% or 90% of the total oil) [15]. Clove has been used for a long time by timetime by by civilizations civilizations because because of of its its flavor flavor and and its its properties properties make make it itimportant important for for culinary culinary and and civilizations because of its flavor and its properties make it important for culinary and medicinal medicinalmedicinal uses. uses. Eugenol Eugenol has has been been included included as as a aspicy spicy flavoring flavoring in in whisky, whisky, ice ice cream, cream, baked baked goods goods uses. Eugenol has been included as a spicy flavoring in whisky, ice cream, baked goods and candy andand candy candy in in restricted restricted concentrations concentrations [16–18]. [16–18]. Eugenol Eugenol has has dual dual effect effect on on the the oxidative oxidative stress, stress, in restrictedwhichwhich can can concentrations action action as as an an [antioxidant 16antioxidant–18]. Eugenol or or prooxidant prooxidant has dual effectagent. agent. onIn In theaddition, addition, oxidative it ithas stress,has anti anti which‐carcinogenic,‐carcinogenic, can action as ancytotoxiccytotoxic antioxidant and and antitumor antitumor or prooxidant properties. properties. agent. Considering Considering In addition, the the it importance has importance anti-carcinogenic, of of eugenol eugenol in cytotoxicin the the area area andof of food food antitumor and and properties.humanhuman health, Consideringhealth, in in this this review, the review, importance we we discuss discuss of eugenolthe the role role of in of eugenol the eugenol area on of on foodredox redox and status status human and and its health, its potential potential in this use use review, in in wethe discussthe treatment treatment the role and and of prevention prevention eugenol on of of redoxcancer. cancer. status Searches Searches and were itswere potential performed performed use in in the the the scientific scientific treatment literature literature and prevention database database of cancer.PubMedPubMed Searches comprising comprising were performedall all papers papers in inin English theEnglish scientific published published literature until until September databaseSeptember PubMed2017 2017 using using comprising the the following following all paperskey key in Englishwords:words: eugenol eugenol published with with until oxidant; oxidant; September antioxidant; antioxidant; 2017 cancer; cancer; using cytotoxic; thecytotoxic; following or or antitumor. antitumor. key words: No No exclusion exclusion eugenol criteria criteria with oxidant;were were antioxidant;performed.performed. cancer; cytotoxic; or antitumor. No exclusion criteria were performed. OCHOCH33 OHOH FigureFigureFigure 1.1. 1. Chemical Chemical structure structure structure of of of eugenol. eugenol. eugenol. 2. Anti-Carcinogenic/Chemopreventive2.2. Anti Anti‐Carcinogenic/Chemopreventive‐Carcinogenic/Chemopreventive EffectEffect Effect of of Eugenol Eugenol and and and Its ItsIts Relation RelationRelation to to to the the the Inhibition Inhibition Inhibition of of of OxidativeOxidativeOxidative Stress Stress Stress TheTheThe ability ability ability to to inhibitto inhibit inhibit oxidative oxidative oxidative stressstress stress has has been been described described described as asas a aprotective protective effect effect effect against against against cancer cancer cancer formationformationformation (carcinogenesis (carcinogenesis (carcinogenesis or or or tumorigenesis); tumorigenesis); tumorigenesis); on on on the the the other other other hand, hand,hand, once once a a acancer cancer cancer has has has already already already formed, formed, formed, thethe antioxidant antioxidant effect effect can can contribute contribute to to the the cancer’s cancer’s development, development, while while the the pro pro‐oxidant‐oxidant effect effect can can the antioxidant effect can contribute to the cancer’s development, while the pro-oxidant effect can induceinduce cancer cancer cell cell death death by by several several signaling signaling pathways pathways [19]. [19]. Interestingly, Interestingly, eugenol eugenol has has been been induce cancer cell death by several signaling pathways [19]. Interestingly, eugenol has been described describeddescribed as as an an agent agent with with a adouble double effect, effect, antioxidant antioxidant and and pro pro‐oxidant,‐oxidant, presenting presenting beneficial beneficial as an agent with a double effect, antioxidant and pro-oxidant, presenting beneficial effects in the effectseffects in in the the prevention prevention of of cancer cancer formation formation and and in in cancer cancer treatment treatment (Figure (Figure 2). 2). Despite Despite some some preventioncontradictorycontradictory of cancer studies, studies, formation there there are and are many inmany cancer articles articles treatment evaluating evaluating (Figure these these2). Despite biochemical biochemical some and contradictory and pharmacologic pharmacologic studies, thereaspects.aspects. are many articles evaluating these biochemical and pharmacologic aspects. FigureFigure 2. 2. The The dual dual effect effect of of eugenol eugenol in in the the oxidative oxidative stress stress and and its its action action in in cancer cancer development development Figure 2. The dual effect of eugenol in the oxidative stress and its action in cancer development andand treatment. treatment. and treatment. Nutrients 2017, 9, 1367 3 of 15 The anti-carcinogenic effect of eugenol had been investigated in several models [20–28]. The anti-carcinogenic effect of eugenol against skin carcinogenesis was investigated by Kaur et al. [20]. Skin cancer was initiated
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