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Cinnamic Acid Derivatives and Their Biological Efficacy

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Cinnamic Acid Derivatives and Their Biological Efficacy International Journal of Molecular Sciences Review Cinnamic Acid Derivatives and Their Biological Efficacy Review NgonidzasheCinnamic Ruwizhi Acid and Blessing Derivatives Atim Aderibigbe and * their Biological DepartmentEfficacy of Chemistry, University of Fort Hare, Alice Campus, Alice 5700, Eastern Cape, South Africa; [email protected] * NgonidzasheCorrespondence: Ruwizhi [email protected] and Blessing Atim Aderibigbe * Received:Department 25 March of Chemistry, 2020; Accepted: University 6 May of2020; Fort Published:Hare, Alice 9 Campus, August 2020 5700 Alice, Eastern Cape, South Africa; [email protected] Abstract:* Correspondence:The role played [email protected] by cinnamic acid derivatives in treating cancer, bacterial infections, diabetesReceived: and 25 neurological March 2020; disorders, Accepted: among 06 May many, 2020; hasPublished: been reported. date Cinnamic acid is obtained from cinnamon bark. Its structure is composed of a benzene ring, an alkene double bond and an acrylic acidAbstract: functional The group role played making by it possiblecinnamic to acid modify derivatives the aforementioned in treating cancer, functionalities bacterial with infections, a variety ofdiabetes compounds and resultingneurological in bioactivedisorders, agents among with many enhanced, has been e ffireported.cacy. The Cinnamic nature of acid the is substituents obtained incorporatedfrom cinnamon into cinnamicbark. Its structure acid has beenis composed found to of play a benzene a huge ring, role inan either alkene enhancing double bond or decreasing and an theacrylic biological acid efunctionalfficacy of thegroup synthesized making it cinnamicpossible to acid modify derivatives. the aforementi Some ofoned the derivativesfunctionalities have with been reporteda variety to beof morecompounds effective resulting when compared in bioactive to the agents standard with drugsenhanced used efficacy. to treat chronicThe nature or infectious of the diseasessubstituentsin vitro incorporated, thus making into themcinnamic very acid promising has been therapeutic found to play agents. a huge Compoundrole in either20 enhancingdisplayed potentor decreasing anti-TB activity, the biological compound efficacy27 exhibited of the synt significanthesized antibacterialcinnamic acid activity derivatives. on S. aureusSome ofstrain the of bacteriaderivatives and compounds have been reported with potent to be antimalarial more effect activityive when are compared35a, 35g ,to35i the, 36i standard, and 36b drugs. Furthermore, used to treat chronic or infectious diseases in vitro, thus making them very promising therapeutic agents. compounds 43d, 44o, 55g–55p, 59e, 59g displayed potent anticancer activity and compounds 86f–h Compound 20 displayed potent anti-TB activity, compound 27 exhibited significant antibacterial were active against both hAChE and hBuChE. This review will expound on the recent advances on activity on S. aureus strain of bacteria and compounds with potent antimalarial activity are 35a, 35g, cinnamic acid derivatives and their biological efficacy. 35i, 36i, and 36b. Furthermore, compounds 43d, 44o, 55g–55p, 59e, 59g displayed potent anticancer activity and compounds 86f–h were active against both hAChE and hBuChE. This review will Keywords: cinnamic acid; antimicrobial; anticancer; antimalarial; Alzheimer’s disease expound on the recent advances on cinnamic acid derivatives and their biological efficacy. Keywords: cinnamic acid; antimicrobial; anticancer; antimalarial; Alzheimer’s disease 1. Introduction1. Introduction CinnamicCinnamic acid, acid, a a natural natural aromatic aromatic carboxylic carboxylic acidacid [[11] (Figure (Figure 11),), is is a a key key chemical chemical found found in in plants plants suchsuch as Cinnamomumas Cinnamomum cassia cassia(Chinese (Chinese cinnamon) cinnamon) and andPanax Panax ginseng ginseng, fruits,, fruits, whole whole grains, grains, vegetables vegetables and honeyand [honey1]. The [1]. presence The presence of an acrylicof an acrylic acid group acid gr substitutedoup substituted on the on phenyl the phenyl ring ring gives gives cinnamic cinnamic either a ciseither ora a transcis or configurationa trans configuration with the with latter the beinglatter thebeing most the commonmost common of the of two the two [2,3]. [2,3]. Studies Studies have reportedhave reported that cinnamic that acidcinnamic exhibit acid antioxidant, exhibit antioxidant, antimicrobial antimicrobial [4], anticancer [4], [5 ],anticancer neuroprotective, [5], anti-inflammatoryneuroprotective, andanti-inflammatory antidiabetic properties. and antidiabetic [6]. Cinnamic properties. acid [6]. terminates Cinnamic radical acid terminates chain reactions radical by donatingchain reactions electrons by that donating react withelectrons radicals that formingreact with stable radicals products forming [7 ].stable It is products also used [7]. as It a is fragrant also ingredientused as a infragrant toiletries, ingredient flavorings in toiletries, cosmetics flavorings and detergents cosmetics [ 2and]. Cinnamic detergents acid [2]. Cinnamic can be prepared acid can by enzymaticbe prepared deamination by enzymatic of phenylalanine deamination of [8 phenylalanine]. [8]. O OH 1 FigureFigure 1. 1.Chemical Chemical structure of cinnamic cinnamic acid acid (1 (1).). Besides the cinnamic acid derivatives that occur naturally in plants [2], the presence of a benzene Besides the cinnamic acid derivatives that occur naturally in plants [2], the presence of a benzene ringring and and the the acrylic acrylic acid acid group group makes makes itit possiblepossible to modify it it resulting resulting in in synthetic synthetic cinnamic cinnamic acid acid derivatives [9]. Apart from them being intermediates in producing other compounds like stilbenes Int. J. Mol. Sci. 2020, 21, 5712; doi:10.3390/ijms21165712 www.mdpi.com/journal/ijms Int. J. Mol. Sci. 2020, 21, x; doi: FOR PEER REVIEW www.mdpi.com/journal/ijms Int. J. Mol. Sci. 2020, 21, 5712 2 of 34 Int. J. Mol. Sci. 2020, 21, x FOR PEER REVIEW 2 of 37 derivativesand styrenes, [9]. Apartcinnamic from acid them derivatives being intermediates exhibit antibacterial, in producing antifungal, other compoundsanti-inflammatory like stilbenes [10], andneuroprotective styrenes, cinnamic [11], anticancer acid derivatives [12] and antidiabetic exhibit antibacterial, activities [13]. antifungal, Cinnamic anti-inflammatory acid derivatives that [10 ], neuroprotectivehave been reported [11], anticancer by researchers [12] and antidiabeticinclude ferulic activities acid, [13curcumin]. Cinnamic [11], acid caffeic derivatives acid, p- that havehydroxycinnamic been reported byacid researchers [14] coumaric include and ferulicchlorogeni acid,c acids curcumin [15], [etc.11], These caffeic cinnamic acid, p-hydroxycinnamic acid analogues acidare [ 14differentiated] coumaric and by chlorogenicthe presence acids of hydroxyl [15], etc. grou Theseps cinnamicon the phenyl acid analogues ring that areare dieitherfferentiated free or by themethoxylated presence of hydroxyl[15]. groups on the phenyl ring that are either free or methoxylated [15]. TheThe biological biological activities activities of of di differentfferent cinnamiccinnamic acid derivatives derivatives have have been been attributed attributed to tothe the nature nature andand position position of of the the substituent substituent groups. groups. DrugDrug resist resistanceance and and the the absence absence of of curative curative therapies therapies with with lowlow adverse adverse side side eff effectect profiles profiles to to control control cancer, cancer, microbial microbial growth, growth, neurological neurological disorders disorders etc. etc. has has led toled research to research on the on development the development of therapeutic of therapeutic compounds compounds based based on on cinnamic cinnamic acid acid [16 [16].]. Due Due to to the the biological efficacy of derivatives of cinnamic acid, this review will report different recently biological efficacy of derivatives of cinnamic acid, this review will report different recently synthesized synthesized derivatives of cinnamic acid and their biological activity in vitro and in vivo. derivatives of cinnamic acid and their biological activity in vitro and in vivo. 2.2. Cinnamic Cinnamic Acid Acid Derivatives Derivatives with with AntimicrobialAntimicrobial Activity The World Health Organization (WHO) recognizes infectious diseases caused by bacteria, The World Health Organization (WHO) recognizes infectious diseases caused by bacteria, viruses and fungi as a global health threat, especially in developing and poor countries. About 3.5 viruses and fungi as a global health threat, especially in developing and poor countries. About million people die from infectious diseases annually [17]. In 2018, the WHO reported 37.9 million 3.5 million people die from infectious diseases annually [17]. In 2018, the WHO reported 37.9 million people to be living with Human Immunodeficiency Virus (HIV) worldwide with 770,000 dying from peopleAIDS-related to be living illnesses with [18]. Human The Immunodeficiency2019 Global tuberculosis Virus (TB) (HIV) reported worldwide an estimated with 770,000 10.0 million dying TB from AIDS-relatedinfections and illnesses 1.2 million [18]. deaths The 2019 in 2018. Global Of the tuberculosis TB cases, 8.6% (TB) were reported people an living estimated with HIV 10.0 [19]. million The TB infectionsappearance and of 1.2 drug-resistant million deaths microbial in 2018. strains
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