UPLC–PDA–ESI–qTOF-MS profiling and potent anti-HSV-II activity of Eucalyptus sideroxylon leaves

Okba, Mona M.; Gedaily, Rania A. El; Ashour, Rehab M.

doi:10.1016/j.jchromb.2017.10.065

Cited by 32 publications

(40 citation statements)

References 49 publications

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“…It is the most abundant and thus the diagnostic fragment ion for sideroxylonals, followed by a less abundant peak of m/z 181, suggested to be the diformyl phloroglucinol moiety by Chenavas et al (2015). For macrocarpals, the diagnostic fragment ion detected in the compounds 1-4 is m/z 207, in agreement with previous reports (Eyles et al, 2003; Okba et al, 2017), and we here suggest it to be the isopentyl diformyl phloroglucinol moiety + C 2 H 2 . The fragmentation pattern and the high-resolution mass spectra shown here have great value for future studies allowing the confident identification of FPCs, which have probably been overlooked in many other plant species due to the challenges of detecting them.…”

Section: Discussionsupporting

confidence: 93%

“…For example, 49 FPCs peaks were identified in a single E. globulus leaf extract, undoubtedly representing some new uncharacterized compounds. Previously, Okba et al (2017) putatively identified 13 FPCs in a bulk leaf extract of E. sideroxylon using HPLC-MS/MS. Using the current method, we report 34 FPCs identified in leaves of the same species.…”

Section: Discussionmentioning

confidence: 99%

“…The fragmentation pattern generated by high resolution tandem mass spectrometry is extremely valuable, because it can guide the identification or differentiation of structurally related compounds (Neilson et al, 2011; Heskes et al, 2012). Recently, HPLC-MS/MS allowed the putative identification of 13 FPCs among 70 phytoconstituents in an E. sideroxylon leaf extract (Okba et al, 2017), however the method was not developed specifically for FPCs, and may underestimate the diversity of this class of specialized metabolites. Here we present a fast, simple, and reliable method for FPCs extraction, detection, and quantification from complex biological samples using ultra-high-performance liquid chromatography coupled to ultra-violet diode array detection and electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-DAD-ESI-Q-TOF-MS/MS) system, which enabled the detection of 49 FPCs in one single leaf extract.…”

Section: Introductionmentioning

confidence: 99%

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Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

et al. 2019

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The Eucalyptus genus is a hyper-diverse group of long-lived trees from the Myrtaceae family, consisting of more than 700 species. Eucalyptus are widely distributed across their native Australian landscape and are the most widely planted hardwood forest trees in the world. The ecological and economic success of Eucalyptus trees is due, in part, to their ability to produce a plethora of specialized metabolites, which moderate abiotic and biotic interactions. Formylated phloroglucinol compounds (FPCs) are an important class of specialized metabolites in the Myrtaceae family, particularly abundant in Eucalyptus . FPCs are mono- to tetra-formylated phloroglucinol based derivatives, often with an attached terpene moiety. These compounds provide chemical defense against herbivory and display various bioactivities of pharmaceutical relevance. Despite their ecological and economic importance, and continued improvements into analytical techniques, FPCs have proved challenging to study. Here we present a simple and reliable method for FPCs extraction, identification and quantification by UHPLC-DAD-ESI-Q-TOF-MS/MS. The method was applied to leaf, flower bud, and flower samples of nine different eucalypt species, using a small amount of plant material. Authentic analytical standards were used to provide high resolution mass spectra and fragmentation patterns. A robust method provides opportunities for future investigations into the identification and quantification of FPCs in complex biological samples with high confidence. Furthermore, we present for the first time the tissue-based localization of FPCs in stem, leaf, and flower bud of Eucalyptus species measured by mass spectrometry imaging, providing important information for biosynthetic pathway discovery studies and for understanding the role of those compounds in planta .

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Section: Discussionsupporting

confidence: 93%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

et al. 2019

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“…Within the antiviral activities detected, there were compounds that also inhibited hepatitis A, coxsackie and adenoviruses, besides HSV-1 and HSV-2. Interestingly, the highest antiviral activity was observed against HSV-2, with the antiviral effect acting pre-treatment (virucidal), thus inhibiting virus entry and subsequent infection processes, while the antiviral effect against HSV-1 was only observed when the extract was incubated with the virus previous to the cell infection (Okba et al, 2017). In addition, twelve compounds isolated from the leaves and twigs of E. globulus were found to have antiviral activity against HSV-1 and HSV-2.…”

Section: Plant-derived Compounds With Antiviral Activity Against Hsvsmentioning

confidence: 99%

Current Antivirals and Novel Botanical Molecules Interfering With Herpes Simplex Virus Infection

et al. 2020

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Herpes simplex viruses type 1 (HSV-1) and type 2 (HSV-2) are highly prevalent within the human population and are characterized by lifelong infections and sporadic recurrences due to latent neuron infection. Upon reactivations, HSVs may manifest either, symptomatically or asymptomatically and be shed onto others through mucosae body fluids. Although, HSVs can produce severe disease in humans, such as lifethreatening encephalitis and blindness, the most common symptoms are skin and mucosal lesions in the oro-facial and the genital areas. Nucleoside analogs with antiviral activity can prevent severe HSV infection, yet they are not very effective for treating skin manifestations produced by these viruses, as they only reduce in a few days at most the duration of lesions. Additionally, HSV variants that are resistant to these antivirals may arise, especially in immunosuppressed individuals. Thus, new antivirals that can reduce the severity and duration of these cutaneous manifestations would certainly be welcome. Here, we review currently available anti-herpetic therapies, novel molecules being assessed in clinical trials and new botanical compounds reported in the last 20 years with antiviral activities against HSVs that might represent future treatments against these viruses.

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“…Eucalyptus extracts have shown various biological effects, such as antibacterial, antifungal, antioxidant, or anti-hyperglycemic activities [ 4 , 9 ]. Extracts of the leaves of E. sideroxylon and E. camaldulensis have exerted antiviral activity against herpes simplex virus (HSV) [ 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Anti-Infectivity against Herpes Simplex Virus and Selected Microbes and Anti-Inflammatory Activities of Compounds Isolated from Eucalyptus globulus Labill.

Brezáni

Leláková

Hassan

et al. 2018

Viruses

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Herpes simplex virus (HSV) causes numerous mild-to-serious human diseases, including mucocutaneous herpes infections and life-threatening herpes encephalitis. Moreover, herpes viral lesions can be complicated by inflammation and secondary bacterial infections. The development of resistance to antiviral drugs along with the undesirable side effects of these drugs are relevant argue for the development of new anti-HSV drugs with diverse mechanisms of action. Eucalyptus extracts have been used for decades to combat various infectious diseases. We isolated and studied 12 pure compounds and one mixture of two constitutional isomers from the leaves and twigs of E. globulus. The structures were identified by spectroscopic methods (NMR, HR-MS, IR) and all of them were tested for antiherpetic activity against the replication of antigen types HSV-1 and HSV-2. Tereticornate A (12) (IC50: 0.96 μg/mL; selectivity index CC50/IC50: 218.8) showed the strongest activity in the anti-HSV-1 assay, even greater than acyclovir (IC50: 1.92 μg/mL; selectivity index CC50/IC50: 109.4), a standard antiviral drug. Cypellocarpin C (5) (EC50: 0.73 μg/mL; selectivity index CC50/EC50: 287.7) showed the most potent anti-HSV-2 activity, also more intensive than acyclovir (EC50: 1.75 μg/mL; selectivity index CC50/EC50: 120.0). The antimicrobial activity of the isolated compounds was also evaluated against the bacteria Staphylococcus aureus, Bacillus cereus, Escherichia coli, and Pseudomonas aeruginosa and the yeast Candida albicans. The anti-inflammatory potential was examined using LPS-stimulated THP-1-XBlue™-MD2-CD14 and THP-1 macrophages and focusing on the influences of the NF-κB/AP-1 activity and the secretion of pro-inflammatory cytokines IL-1β and TNF-α.

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UPLC–PDA–ESI–qTOF-MS profiling and potent anti-HSV-II activity of Eucalyptus sideroxylon leaves

Cited by 32 publications

References 49 publications

Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

Quantification and Localization of Formylated Phloroglucinol Compounds (FPCs) in Eucalyptus Species

Current Antivirals and Novel Botanical Molecules Interfering With Herpes Simplex Virus Infection

Anti-Infectivity against Herpes Simplex Virus and Selected Microbes and Anti-Inflammatory Activities of Compounds Isolated from Eucalyptus globulus Labill.

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