Investigation of Commiphora Myrrha (Nees) Engl
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pharmaceuticals Article Investigation of Commiphora myrrha (Nees) Engl. Oil and Its Main Components for Antiviral Activity Valentina Noemi Madia 1,† , Marta De Angelis 2,† , Daniela De Vita 3,*, Antonella Messore 1, Alessandro De Leo 1 , Davide Ialongo 1 , Valeria Tudino 1, Francesco Saccoliti 4, Giovanna De Chiara 5 , Stefania Garzoli 6 , Luigi Scipione 1 , Anna Teresa Palamara 2 , Roberto Di Santo 1 , Lucia Nencioni 2,† and Roberta Costi 1,† 1 Istituto Pasteur-Fondazione Cenci Bolognetti, Dipartimento di Chimica e Tecnologie del Farmaco, “Sapienza” Università di Roma, p.le Aldo Moro 5, I-00185 Rome, Italy; [email protected] (V.N.M.); [email protected] (A.M.); [email protected] (A.D.L.); [email protected] (D.I.); [email protected] (V.T.); [email protected] (L.S.); [email protected] (R.D.S.); [email protected] (R.C.) 2 Laboratory Affiliated to Pasteur Italia-Fondazione Cenci Bolognetti, Department of Public Health and Infectious Diseases, “Sapienza” University of Rome, p.le Aldo Moro 5, I-00185 Rome, Italy; [email protected] (M.D.A.); [email protected] (A.T.P.); [email protected] (L.N.) 3 Department of Environmental Biology, “Sapienza” University of Rome, p.le Aldo Moro 5, I-00185 Rome, Italy 4 D3 PharmaChemistry, Italian Institute of Technology, Via Morego 30, I-16163 Genova, Italy; [email protected] 5 Institute of Translational Pharmacology, National Research Council (CNR), Via del Fosso del Cavaliere 100, I-00133 Rome, Italy; [email protected] 6 Citation: Madia, V.N.; De Angelis, Department of Drug Chemistry and Technologies, Sapienza University of Rome, p.le Aldo Moro 5, M.; De Vita, D.; Messore, A.; De Leo, I-00185 Rome, Italy; [email protected] * Correspondence: [email protected]; Tel.: +39-06-4991-2788 A.; Ialongo, D.; Tudino, V.; Saccoliti, † These authors contributed equally. F.; De Chiara, G.; Garzoli, S.; et al. Investigation of Commiphora myrrha Abstract: The resinous exudate produced by Commiphora myrrha (Nees) Engl. is commonly known (Nees) Engl. Oil and Its Main as true myrrh and has been used since antiquity for several medicinal applications. Hundreds of Components for Antiviral Activity. Pharmaceuticals 2021, 14, 243. metabolites have been identified in the volatile component of myrrh so far, mainly sesquiterpenes. https://doi.org/10.3390/ph14030243 Although several efforts have been devoted to identifying these sesquiterpenes, the phytochemical analyses have been performed by gas-chromatography/mass spectrometry (GC–MS) where the high Academic Editor: temperature employed can promote degradation of the components. In this work, we report the Monica Notarbartolo extraction of C. myrrha by supercritical CO2, an extraction method known for the mild extraction conditions that allow avoiding undesired chemical reactions during the process. In addition, the Received: 5 February 2021 analyses of myrrh oil and of its metabolites were performed by HPLC and GC–MS. Moreover, we Accepted: 3 March 2021 evaluated the antiviral activity against influenza A virus of the myrrh extracts, that was possible Published: 9 March 2021 to appreciate after the addition of vitamin E acetate (α-tocopheryl acetate) to the extract. Further, the single main bioactive components of the oil of C. myrrha commercially available were tested. Publisher’s Note: MDPI stays neutral Interestingly, we found that both furanodienone and curzerene affect viral replication by acting on with regard to jurisdictional claims in different steps of the virus life cycle. published maps and institutional affil- iations. Keywords: Commiphora myrrha; sesquiterpenes; myrrh oil; vitamin E acetate; supercritical CO2 fluid extraction; HPLC; antiviral activity; influenza A H1N1 virus Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. 1. Introduction This article is an open access article distributed under the terms and Commiphora genus (Burseraceae) includes more than 150 species especially occurring conditions of the Creative Commons in northeastern Africa, southern Arabia and India [1]. The species Commiphora myrrha Attribution (CC BY) license (https:// (Nees) Engl. produces a resinous exudate known as true myrrh that has been used for creativecommons.org/licenses/by/ centuries as an embalming ointment, wound-healing remedy and for other medicinal ap- 4.0/). plications [2]. Myrrh consists of alcohol-soluble resins and volatile oil together with a gum Pharmaceuticals 2021, 14, 243. https://doi.org/10.3390/ph14030243 https://www.mdpi.com/journal/pharmaceuticals Pharmaceuticals 2021, 14, x FOR PEER REVIEW 2 of 11 Pharmaceuticals 2021, 14, 243 2 of 11 centuries as an embalming ointment, wound-healing remedy and for other medicinal applications [2]. Myrrh consists of alcohol-soluble resins and volatile oil together with a gum soluble in water containing polysaccharides, proteins and long chain aliphatic derivatives. Thesoluble lipophilic in water part containing of myrrh is polysaccharides, composed of steroids, proteins sterols and long and chainterpenes aliphatic [3]. derivatives. To date, hundredsThe lipophilicof metabolites part have of myrrh been isidentified composed in the of steroids,volatile component sterols and of terpenes myrrh, [3]. To date, where sesquiterpeneshundreds are of the metabolites major components have been. identifiedNotably, furanosesquiterpenes in the volatile component suchof as myrrh, where furanoelemanes,sesquiterpenes furanoeudesmanes, are the major and components.furanogermacranes Notably, are furanosesquiterpenes the characteristic such as fura- constituents ofnoelemanes, myrrh oil [4]. furanoeudesmanes, As important co andmponents furanogermacranes of volatile oil, are sesquiterpenoids the characteristic constituents possess diverseof biological myrrh oil [activities,4]. As important including components antibacterial, of volatile antifungal, oil, sesquiterpenoids and antiparasitic possess diverse properties. It biologicalis also worthy activities, of note including that recent antibacterial, papers reported antifungal, the in and vitro antiparasitic and in vivo properties. It is analgesic andalso anticancer worthy ofactivities note that [5–8] recent of papersfour main reported components the in vitro of andthe involatile vivo analgesic oil, and anti- namely furanodienonecancer activities (1), furanoeudesma-1,3-diene [5–8] of four main components (2), curzerene of the ( volatile3), and β oil,-elemene namely (4 furanodienone) β (Figure 1). (1), furanoeudesma-1,3-diene (2), curzerene (3), and -elemene (4) (Figure1). Figure 1. StructuresFigure 1. of Structures the main sesquiterpenes of the main sesquiterpen in myrrh oil:es furanodienonein myrrh oil: furanodienone (1), furanoeudesma-1,3-diene (1), furanoeudesma- (2), curzerene (3) and β-elemene1,3-diene (4). (2), curzerene (3) and β-elemene (4). Some works [9,10]Some have works also [9 ,been10] have devoted also beento the devoted identification to the identificationor characterization or characterization of of these aforementionedthese aforementioned sesquiterpenes sesquiterpenes but most of the but phytochemical most of the phytochemical analyses have analyses been have been performed byperformed gas chromatography by gas chromatography where the high where temperature the high employed temperature can employed promote can promote degradation ofdegradation the components, of the thus components, influencing thus the influencing qualitative–quantitative the qualitative–quantitative composition composition of the mixture.of For the instance, mixture. Forthe rearrangem instance, theent rearrangement of furanodiene of to furanodiene curzerene during to curzerene the during the essential oil extractionessential process oil extraction and/or process during and/or conventional during gas conventional chromatographic gas chromatographic analysis, analysis, ◦ in which temperaturesin which temperaturesover 200 °C are over employed, 200 C are is reported employed, [11]. is reported [11]. Here we describeHere the we extraction describe the of extractionC. myrrha ofbyC. supercritical myrrha by supercriticalCO2, an extraction CO2, an extraction method that ismethod well known that is for well its knownmany advantages for its many in advantagesobtaining volatile in obtaining extracts volatile or aroma extracts or aroma substances and,substances more generally, and, more to extract generally, lipophilic to extract compounds lipophilic from compounds a wide variety from a wideof variety of matrices. Indeed,matrices. in addition Indeed, to inbeing addition non-toxic to being and non-toxic non-flammable, and non-flammable, the mild extraction the mild extraction conditions allowconditions avoiding allow undesired avoiding chemical undesired reactions chemical during reactions the process. during This the process.leads to This leads to shorter extractionshorter times extraction without times withoutdecomp decomposingosing compounds compounds vulnerable vulnerable to to high temperatures temperatures differentlydifferently from hydro- or steam- steam-distilleddistilled oils oils [12]. [12]. In In the the present present work, work, the the analysis of analysis of myrrhmyrrh oil oil and and the the quantification quantification of of its its metabolites metabolites were were performed performed by HPLC,HPLC, so as to avoid so as to avoidhigh high temperatures temperatures also also during during the analyticalthe analytical process.