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Pimenta Dioica and Pimenta Racemosa

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Pimenta Dioica and Pimenta Racemosa Food & Function View Article Online COMMUNICATION View Journal | View Issue Pimenta dioica and Pimenta racemosa: GC-based metabolomics for the assessment of seasonal and Cite this: Food Funct., 2021, 12, 5247 organ variation in their volatile components, Received 7th February 2021, in silico and in vitro cytotoxic activity estimation† Accepted 25th April 2021 DOI: 10.1039/d1fo00408e Fadia S. Youssef, a Rola M. Labib,a Haidy A. Gad,a SafaaY. Eid,b a,c d rsc.li/food-function Mohamed L. Ashour and Hanaa H. Eid * Volatile constituents isolated from the stems (S) and leaves (L) of compounds detected in the oils by determining their inhibitory Pimenta dioica (PD) and Pimenta racemosa (PR) during the four effect on human DNA topoisomerase II (TOP-2), human cyclin- seasons were analyzed using GLC/FID (Gas liquid chromatography dependent kinase 2 (CDK-2) and matrix metalloproteinase 13 – flame ionization detector) and GLC/MS (Gas liquid chromato- (MMP-13). o-Cymene followed by eugenol showed the highest graphy – mass spectrometry). Eighty-nine compounds were ident- fitting with all of the examined proteins approaching doxorubicin. ified in all samples, in which oxygenated monoterpene represented It can be concluded that GC coupled with chemometrics provide a by eugenol was the major constituent in PDS-S3 (autumn) (88.71%) strong tool for the discrimination of samples, while Pimenta could and PDS-S2 (summer) (88.41%). Discrimination between P. dioica afford a natural drug that could alleviate cancer. and P. racemosa leaves and stems in different seasons was achieved by applying chemometrics analysis comprising Principal Component Analysis (PCA) and Hierarchal Cluster Analysis (HCA). Introduction For P. dioica, they were partially segregated where leaves collected from spring and autumn were superimposed, and similarly for Nowadays, spices play an important role worldwide as natural P. dioica stems collected in summer and autumn. For P. racemosa coloring, flavoring agents, as well as antimicrobials, antioxi- leaves, the PCA score plot showed that all seasons were comple- dants in the food and beverage industries, in addition to its Published on 26 April 2021. Downloaded 7/9/2021 2:15:43 PM. tely segregated from each other, with the winter and autumn utilization in cosmetics and perfumery. Moreover, spices samples being in very close distance to each other. P. racemosa showed an immense potential in the nutraceutical industry stems collected in autumn and spring exhibited significant vari- owing to their beneficial health and physiological effects. ation, as they were completely detached from each other. Spices are commonly obtained from different plant parts, such Moreover, summer and winter fell in a near distance to each other. as seeds, fruits, leaves, flowers and subterranean organs, An in vitro cell viability assay was done to evaluate the variation in which are rich in essential oils.1 the cytotoxicity of the isolated essential oils against breast The essential oils of many herbs and spices are used nowa- (MCF-7), hepatic (HepG-2), and cervical (HeLa-2) cancer cell lines days in aromatherapy, as they showed many reported biologi- using the MTT assay. The maximum cytotoxic effect was observed cal activities, especially the significant potential as anti- by PDL against HeLa, HepG-2 and MCF-7 cells with IC50 values microbial, antifungal, antiviral, analgesic, anticarcinogenic, − equal to 122.1, 139.6, and 178.7 µg mL 1, respectively. An in silico antiparasitic, anti-inflammatory and antioxidant agents.2 study was done to assess the cytotoxic effect of the major Genus Pimenta Lindley (family Myrtaceae), comprises 18 species of aromatic trees, native to Tropical America and to the Caribbean, that are widely distributed in Central America. The most commonly known species are Pimenta dioica and aDepartment of Pharmacognosy, Faculty of Pharmacy, Ain-Shams University, 11566 Cairo, Egypt Pimenta racemosa, where the former is called allspice or bDepartment of Biochemistry, Faculty of Medicine, Umm Al-Qura University, Makkah, Jamaica pepper, while the latter is named by Bay or Bay-rum- 1,3 Saudi Arabia tree. cDepartment of Pharmaceutical Sciences, Pharmacy Program, Batterjee Medical Traditionally, the berries of Pimenta were used in the treat- College, 21442 Jeddah, Saudi Arabia ment of digestive disorders, such as nausea, cramp, flatulence, dDepartment of Pharmacognosy, Faculty of Pharmacy, Cairo University, 11562 Cairo, and colic, as well as for the management of diarrhea, dyspep- Egypt. E-mail: [email protected]; Tel: (+2) 01223907981 4 †Electronic supplementary information (ESI) available. See DOI: 10.1039/ sia, and rheumatism. Moreover, the essential oils are utilized 4–6 d1fo00408e in food industry, perfumery and cosmetics. In addition, the This journal is © The Royal Society of Chemistry 2021 Food Funct.,2021,12,5247–5259 | 5247 View Article Online Communication Food & Function essential oils of Pimenta leaves and fruits can improve the GLC/FID and GLC/MS analyses neurological signs as tension due to stress, nervous collapse, The GLC/FID and GLC/MS analyses were carried out on a 5 tightness, neuralgia and anxiety. Varian 3400 (Varian GmbH, Darmstadt, Germany) and The bioactivities and the chemical composition of the Hewlett-Packard gas chromatograph (GC 5890 II, Hewlett- ff essential oils of the Pimenta species obtained from di erent Packard GmbH, Bad Homburg, Germany), respectively 5,6 locations have been recently reviewed. Concerning the bio- equipped with OV-5 fused bonded column (30 m × 0.25 mm × logical activities, many were reported regarding the essential 0.25 μm) (Ohio Valley, Ohio, USA). The GLC conditions were ff oils and the di erent extracts of various Pimenta species, conducted as previously reported by El-Readi et al.13 For GLC/ including antioxidant, anti-inflammatory, antibacterial, anti- FID, helium was used as a carrier gas with a flow rate of 2 mL fungal, antiviral, anticancer, hypoglycemic, antitermite, anti- −1 – min ; the initial temperature used was 45 °C, followed by ff 1,5 7 − nociceptive and antivenum e ects as well. 2 min isothermal, 300 °C, 4 °C min 1 300 °C, then 20 min iso- However, relatively limited information could be found in thermal. The detector and injector temperatures were 300 and 8,9 the literature concerning the essential oils of leaves, 250 °C, respectively. The split ratio was 1 : 20. The chromato- 8,10 8 flowers and fruits of P. racemosa and P. dioica, which are grams were recorded and integrated using the Peak Simple cultivated in Egypt. Moreover, the lack of published data con- 2000 chromatography data system (SRI Instruments, cerning the essential oils of the stem of P. racemosa and California, USA). All data were calculated from three indepen- P. dioica encouraged us to carry out this work. Hence, the dent chromatographic runs, and the averages of the area target of this study was to evaluate the influence of the harvest under the peak were used to calculate the abundance of each time on the essential oils of the stems and leaves of component relative to the total area under the peaks. For GLC/ P. racemosa and P. dioica, as regards to the composition and MS, the capillary column was directly coupled to a quadrupole their discrimination using multivariate analyses. Additionally, mass spectrometer (SSQ 7000, Thermo-Finnigan, Bremen, in vitro cytotoxic activity estimation for the oils, followed by Germany). The injector temperature was 250 °C. The helium − in silico molecular modelling studies were performed for the carrier gas flow rate was 2 mL min 1. The following conditions major compounds identified in the oils on human DNA topoi- were employed for all mass spectra: filament emission current, somerase II (TOP-2), human cyclin-dependent kinase 2 100 mA; electron energy, 70 eV; ion source, 175 °C; diluted (CDK-2) and matrix metalloproteinase 13 (MMP-13), as well as samples (0.5% v/v) were injected with split mode (split ratio, aiming to outline their probable mode of action as cytotoxic 1 : 15). The Wiley Registry of Mass Spectral Data 8th edition, agents. Additionally, the present work aimed to establish the NIST Mass Spectral Library14,15 was used to identify the com- best economic conditions for the oil production for further position of the tested essential oils, and confirmed by litera- application in pharmaceutical industries. ture data.11 All reagents and controls used for GLC analysis were obtained from Sigma (Sigma Aldrich GmbH, Sternheim, Germany). Published on 26 April 2021. Downloaded 7/9/2021 2:15:43 PM. Materials and methods Chemometric analysis and data analysis Plant material Both Principal component analysis (PCA) and Hierarchal Leaves (L) and stems (S) of Pimenta dioica (L.) Merr. (PD) Cluster Analysis (HCA) were applied as chemometric methods and Pimenta racemosa Mills J.W. Moore (PR) (Family for multivariate analysis of GC analyses for the metabolic pro- Myrtaceae) were collected (2017) from Alzohreya botanical filing of data from different Pimenta species. Unscrambler® X garden (Cairo, Egypt) in spring S1 (April), summer S2 (July), 10.4 from Computer Aided Modeling, AS, Norway (CAMO) was autumn S3 (October) and winter S4 (January). The plants were used to apply PCA and HCA analyses. These multivariate dis- kindly authenticated morphologically by Dr Therese Labib; crimination techniques are considered a simplistic approach consultant of plant taxonomy at the Ministry of Agriculture, for the classification and grouping of different species based Egypt. Voucher specimens of
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