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Leaf Paper

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m.mourad
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Jour of Crematorepy 8106-1049 (2017) 235-242 ‘Contents lists availible at ScienceDirect Journal of Chromatography B ELSEVIER! journal homepage: [Link]/locateljchromb UPLC-PDA-ESI-qTOF-MS profiling and potent anti-HSV-II activity of Eucalyptus sideroxylon leaves ‘Mona M. Okba, Rania A. El Gedaily, Rehab M. Ashour* Depwoent of Parmacgon. cl ofPharmay, Ca Unerty, Ks Bt-Aty, Ce, 1562, Feet ARTICLE INFO ABSTRACT — aby oe of he mon import ad hy explodes in fanly Myra, An UPLC/RDAES ip tn {TOFS method was adopted Yo ety Buss onan Cann x Woss lens pyocnstoent {on pom nal emaogety jteiy of dragon Inver plotgcintich ntact PORE on VERO els wat dated The on antiviral effect of PGRE against hepatitis A (HAY), herpes simplex type 1 (HSV-D, herpes simplex type 2 (HSV-ID, Seep i se Scnucl (Gub0 and leovraer warn to cvauned ing TT anny ((43-ineyNaesl 291.28 ler Alipbenyl tetrazolium bromide). UPLC-MS analysis allowed the Idntfeation of 70 metabolites including: 25 terpenes 1 plrogane, ty aie avons Slip cl eae alle ede, fh To miceaneou Twenty four metaboler rife nthe leave den and our In the gen ‘cabs ae rege hr fr he et in. PORE ws fond tobe hocyaan the cocerton hat ‘ede hcl ay by 5 (Cu) war 408 mg/l Minune encetaten (NTO) of PORE Ver cli was 312 mg/m Thebes antl activi wa ore alt HSVI Techn woe through decreasing the vr pletion an 19.36, 6 89% non) and tachment on Veo cl Chg Son Spy 08 35a str than vial tt ng 208.2 Hn, Sa bit). troy pots coe mpfr cn ates operon, ao egg he paar om foul ae 1. inrodvetion SV and HSV ae the cause of mos genital herpes [1]. ConacleB Eucabppus is a diverse genus of Myrtaceae flowering trees and shrubs. It comprises more than 700 species that are widely distributed ‘and native to Australia. Eucalyprus leaves accumulate a very large number of secondary metabolites, Phloroglucinolterpene adducts, phloroglucinol dimers, flavonoids, tannins, triterpenes, and glucose ‘esters of oleuropeic acid are among the most famous Eucalyptus meta- Dolites. In addon, leaves of Bucalypuus species were reported to pos- sess several biological activities (1-4). Bucalpaussderoxylon Cann, ex ‘Woolls known as re-iron bark, iron wood, and mugga [5,6]. The leaves fare used in the production of cineole based eucalyptus oll (7). Many ‘Bucalprus species essential oils and metabolites are well known anti- viral agents [2-13]. One ofthe major challenges isthe in vivo practical ‘use of essential olls. Thus we focused the antiviral potency evaluation (nthe total extract of E. sideraxyion leaves not its essential oil. ‘The outbreaks of several viruses worldwide in last decades drove the ‘author's interest towards the evaluation of .sideroxylon antiviral ac- tivity. Herpes simplex virus (HSV) type I and II were among the selected viruses to be screened; they cause common infections worldwide [14]. virus was also selected, i is linked to insulin dependent diabetes mel- Titus a disease with a high distribution all over the world [16]. Ade novus has a well-documented role in obesity [17], which in turn i a direct cause of several illness. In addition, hepatitis A virus (HAV), {infects liver cells and impair liver function{18]. In spite of the presence of several reports (19-21) concerning the leaves of . sideraxyion nothing is known about its antiviral potential. Also, the leaves sec ondary metabolites are not yet well explored. Thus, we focused this study on analysis of its leaves secondary metabolites to present a complete image for its constituents using. UPLC/PDAVESI-qTOF-MS method. 2. Bxperimental 2.1, Plant materi Bucalypus sideroxyion Cunn. ex Woolls leaves were collected, in ‘April 2013, from E-Kobba palace, Cairo. Identity of the plant was thenticated by the Royal Botanic Gardens Herbarium, Kew, Richmond, ~ Coesponding author a Department of Pharmacognosy Fast of Pharmacy Care Unvesiy, Ka BA Stet, 1562 Egypt ‘Ba edie hah ashourepharms ued. OR. Aso). aep/edorg/101016/ ero. 207 10.055 [Received 21 Aap 2017; Rectved in reve form 22 Oar 2017 cepted 31 Ota 2017 19700202/ © 2017 Beever BV. Al sighs eseved Surrey, United Kingdom. A voucher specimen (No. [Link]) was Aeposited in the museum of Pharmacognosy Department, Faculty of Pharmacy, Cairo University 2.2. High resolution UPLC-MS analysis Dried leaves were ground, extracted with methanol and analyzed using reversed phase ultra performance liquid chromatography, cou- pled to photodiode-array and electrospray ionization mass spectrometer (HPLC-PDA-ESI/MS/MS) [22]. A gradient mobile phase (acetonitrile ‘with aqueous formic acid) was used to allow comprehensive elution of different analytes within 800 s. Metabolites assignments were done by ‘comparing regions of different classes using retention time, in addition to, comparison with MS data (accurate mass, formula and fragmenta- tion pattern) in negative ion mode of the detected compounds with those previously reported in literature [23-26] ‘The applied method was optimized for different classes of Eucalypus secondary metabolites separation and identification. The PDA data ‘were useful for the identification of flavonoids, phloroglucinols, and ‘oleuropeic acid glycosides; whereas further structural characterization ‘was provided by the MS analysis. Secondary metabolites previously characterized in several Eucalyptus species; oleuropeic acid glucoside (OAG), eylic polyketones, phloroghucinols glycosides, avonoids, and tannins are relatively polar compounds with carboxyl or phenolic ‘groups, and so they could be readily ionized as expected inthe negative Jon mode, Moreover, negative-ion MS spectra dsplayed better sensi- tivity and more observable peaks (pks) in previous reports on different Bucalyptus species (25,27-31]. Hence, the negative ionization mode ‘was used forthe Identifieation of B. sideroxylon leaf metabolites. The predominant negative ions of some metabolites were subjected to subsequent fragmentation in the MS/MS mode to obtain more data ‘about the molecular mases 2.3. Preparation of phloroglucinolrich extract (PGRE) “The air-dried powdered leaves of E sideroxylon (20 g) was extracted bby Soxhlet apparatus using methylene chloride:methanol (8:2) at 40°C yielding phloroglucinolsrich extract (PGRE) [32-34] 24, Cytotonelty assay ‘Cytotoxicity evaluation is based on the reduction of MTT (3-145

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