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2021
Abdel-Dayem, S. I. A., M. N. A. Khalil, E. H. Abdelrahman, H. M. El-Gohary, and A. S. Kamel, "Sesquiterpene lactones; Damsin and neoambrosin suppress cytokine-mediated inflammation in complete Freund's adjuvant rat model via shutting Akt/ERK1/2/STAT3 signaling.", Journal of ethnopharmacology, vol. 266, pp. 113407, 2021. Abstract

ETHNOPHARMACOLOGIAL RELEVANCE: Although Damsissa (Ambrosia maritima) is traditionally used as anti-inflammatory and diuretic, the biological activity and mechanism of action of its major constituents are to be elucidated.

AIM: to decipher the anti-arthritic potential of damsin (DMS) and neoambrosin (NMS) and to unfold their molecular signaling in complete Freund's adjuvant (CFA)-induced arthritis model.

MATERIALS AND METHODS: the right hind paw was inoculated with CFA (0.1 ml) at day 0 and 7 while treatments were started from the 14 day and continued for 2 weeks. Rats were randomly assigned into 4 groups; normal group (NRML), CFA-induced arthritis group, CFA-induced arthritis treated with DMS and NMS (10 mg/kg/day) as 3 and 4 group; respectively.

RESULTS: Throughout experimental period, treatments ameliorated the increase of paw volume, knee joint diameter and nociception tests as reflected in open field arena. Also, DSM and NMS suppressed phosphorylation of Akt, STAT-3, ERK1/2 which was further mirrored by inactivation of GSK3β and downregulation of MCP-1 together with CCN1 and NF-kβ in hind paw tissue. Concomitantly, inflammation markers; TNF-α, IL-6, -12 were lowered as confirmed microscopically during examination of hind paw tissue.

CONCLUSION: DSM and NMS-induced suppression of NF-kβ subdues clinical features of RA most probably through repression of Akt/ERK1/2/STAT3 pathway. Therefore, DMS and NMS can serve as safe and effective treatment for rheumatoid arthritis, one of the most disabling chronic, inflammatory and painful autoimmune disease.

2020
Sayed, A. M. E., E. Abdelsattar, and M. N. Khalil, "New calogenin pregnane glycoside derivative from Huernia saudi- arabica and its Lipase and α-Glucosidase Inhibitory Activities.", Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, vol. 127, pp. 110143, 2020. Abstract

As ongoing investigation of Huernia saudi-arabica D.V.Field (Asclepiadaceae), a new steroidal pregnane glycoside (Huernioside A) was isolated from dichloromethane fraction (DCM); it was identified as 3β, 11, 14β, 20(R)-tetrahydroxy-pregna-5,9(11)-diene-3-O-β-D-thevetopyranosyl-(1-4)-β-D-cymaropyranoside(HCP) through analysis of 1D, 2D NMR besides ESI-MS data. The alcoholic extract of the aerial part (ALE), DCM and HCP showed inhibitory potential against pancreatic lipase compared to orilstat. Among the tested samples, the ALE and HCP exhibited a promising pancreatic lipase inhibitory commotion through IC values of 0.61 ± 0.15, 1.23 ± 0.07 mg/ml (equivalent to 88.8 μM), respectively. HCP was prevailed to have a mixed mode of inhibition as exposed by enzyme kinetic studies. Hydrophobic interactions were the major forces involved in ligand enzyme interactions. In contrast, moderate α-glucosidase inhibitory activities were evidenced for ALE and HCP (% inhibition: 24.8 ± 1.8 and 26.6 ± 2.5, respectively) compared to acarbose. This investigation is the first to report on the possible in vitro anti-obesity and anti-diabetic impact of H. saudi-arabica.

Khalil, M. N. A., H. H. Farghal, and M. A. Farag, "Outgoing and potential trends of composition, health benefits, juice production and waste management of the multi-faceted Grapefruit : A comprehensive review for maximizing its value.", Critical reviews in food science and nutrition, pp. 1-22, 2020. Abstract

Grapefruit (GF) Macfad (F. Rutaceae) is one of the major citrus fruits that encompass a myriad of bioactive chemicals and most unique among citrus fruits. Nevertheless, no study has yet to assess comprehensively its multitudinous constituents, health benefits, and valuable waste products. Hereto, the present review provides an updated comprehensive review on the different aspects of GF, its juice production, waste valorization, enhancement of its byproducts quality, and compared to other citrus fruits. Grapefruit uniqueness among other citrus fruits stands from its unique taste, flavor, and underlying complex chemical composition. Despite limonene abundance in peel oil and grapefruit juice (GFJ) aroma, nootkatone and sulfur compounds are the key determinants of its flavor, whereas flavanones contribute to its bitter taste and in conjunction with limonoids. Different postharvest treatments and juice processing are reviewed and in context to its influence on final product quality and or biological effects. Flavanones, furanocoumarins, and limonoids appear as the most prominent in GF drug interactions affecting its metabolism and or excretion. Valorization of GF peel is overviewed for its utilization as biosrobent, its oil in aromatherapy, limonene as antimicrobial or in cosmetics, fruit pectin for bioethanol production, or as biosorbent, and peel phenolics biotransformation. The present review capitalizes on all of the aforementioned aspects in GF and further explore novel aspects of its juice quality presenting the full potential of this valued multi-faceted citrus fruit.

SI, A. - D., K. MNA, A. EH, E. - G. HM, and Y. A, "Ultrasound-assisted extraction of damsin and neoambrosin from Ambrosia maritima: optimization using response surface methodology", Egyptian Journal of Chemistry, 2020.
2019
Srour, A. M., D. H. Dawood, M. N. A. Khalil, and Z. M. Nofal, "Synthesis and 2D-QSAR study of dispiropyrrolodinyl-oxindole based alkaloids as cholinesterase inhibitors.", Bioorganic chemistry, vol. 83, pp. 226-234, 2019 Mar. Abstract

In this work, we describe the regioselective synthesis of some new dispiro[indene-2,3'-pyrrolidine-2',3″-indoline]-1,2″(3H)-dione 4-29 attributable to the previously described methods. All the new chemical entities were assessed in-vitro as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes; while no significant inhibitory activity for the tested compounds were assigned on AChE, compounds 4, 27, 29, 28 and 15 were the most active against BChE enzyme with IC = 13.7 µM, 21.8 µM, 22.1 µM, 22.9 µM and 24.9 µM respectively compared to Donepezil (IC = 0.72 µM). Compound 4 was found to have a mixed type mode of inhibition, the bioactivity of the new chemical entities (N = 26, n = 5, R = 0.893, R cvOO = 0.831, R cvMO = 0.838, F = 33.32, s = 0.003) was elucidated via a statistically significant QSAR model utilizing CODESSA-Pro software that validated the observed results.

Khalil, M. N. A., M. A. Choucry, A. S. El Senousy, A. Hassan, S. A. El-Marasy, S. A. El Awdan, and F. A. Omar, "Ambrosin, a potent NF-κβ inhibitor, ameliorates lipopolysaccharide induced memory impairment, comparison to curcumin.", PloS one, vol. 14, issue 7, pp. e0219378, 2019. Abstract

Despite its poor bioavailability, curcumin is a promising natural polyphenol targeting NF-κβ. NF-κβ is a target for new therapeutics because it plays a pivotal role in the pathophysiology of Alzheimer disease (AD). In contrast, ambrsoin, a sesquiterpene lactone which is a potent NF-κβ inhibitor, is scarcely studied in AD models. The current work aims to assess the efficacy of ambrosin as a possible remedy for AD. In silico studies showed that bioavailability and BBB permeability could be favorable for ambrosin over curcumin. Memory impairment was induced in mice by single intraperitoneal injection of LPS (0.4 mg/kg). Treated groups received curcumin (100 mg/kg) or ambrosin at doses (5 or 10 mg/kg) for 7 days. Mice in treated groups showed a significant improvement in memory functions during Morris water maze and object recognition tests. Curcumin and ambrosin (10 mg/kg) inhibited the upsurge of NF-κβp65 transcript and protein levels. Consequently, downstream pro-inflammatory and nitrosative mediators were inhibited, namely, TNF-α, IL-1β, COX-2 and iNOS. BACE1 was inhibited, thereby reducing amyloid plaques (Aβ) deposition and eventually reducing inflammation and apoptosis of neurons as revealed by immunohistopathological examination. In conclusion, ambrosin can be repurposed as AD remedy after further pharmacokinetic/pharamacodynamic assessments. It could serve as an additional lead drug for AD therapeutics.

2018
Choucry, M. A., M. N. A. Khalil, and S. A. E. Awdan, ": Protective action of Crateva nurvala Buch. Ham extracts against renal ischaemia reperfusion injury in rats via antioxidant and anti-inflammatory activities", Journal of Ethnopharmacology, vol. 214, pp. 45-57, 2018.
2017
Farag, M. A., M. I. Fekry, A. - H. L.A., M. N. A. Khalil, H. R. El-Sedi, A. Meyer, A. Prozel, H. Westphal, and L. Wessjohan, "Cytotoxic effects of Sarcophyton sp. Soft corals-Is there a correlation to their NMR fingerprints", Marine Drugs, vol. 51, pp. 211-224, 2017.
Khalil, M. N. A., M. I. Fekry, and M. A. Farag, "Metabolome based volatiles profiling in 13 date palm fruit varieties from Egypt via SPME GC–MS and chemometrics", Food Chemistry, vol. 217, pp. 171-181, 2017.
2016
ElSayed, A., Ezza, Shahira M, M. N. Khalil, and S. El-Hawary, "Chemical composition and evaluation of possible alpha glucosidase inhibitory activity of eight Aloe species", Journal of Medicinal Plants Research, vol. 10, pp. 167-178, 2016.
2015
Khalil, M. N. A., W. Brandt, T. Beuerle, D. Reckwell, J. Groeneveld, R. Hänsch, M. M. Gaid, B. Liu, and L. Beerhues, "O-Methyltransferases involved in biphenyl and dibenzofuran biosynthesis", The Plant Journal, 2015. Abstract
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2014
Coyne, S., A. Litomska, C. Chizzali, M. N. A. Khalil, K. Richter, L. Beerhues, and C. Hertweck, "Control of Plant Defense Mechanisms and Fire Blight Pathogenesis through the Regulation of 6-Thioguanine Biosynthesis in Erwinia amylovora", ChemBioChem, vol. 15, no. 3: Wiley Online Library, pp. 373–376, 2014. Abstract
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2013
Coyne, S., C. Chizzali, M. N. A. Khalil, A. Litomska, K. Richter, L. Beerhues, and C. Hertweck, "Biosynthesis of the Antimetabolite 6-Thioguanine in Erwinia amylovora Plays a Key Role in Fire Blight Pathogenesis", Angewandte Chemie, vol. 125, no. 40: Wiley Online Library, pp. 10758–10762, 2013. Abstract
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Khalil, M. N. A., T. Beuerle, A. Müller, L. Ernst, V. B. R. Bhavanam, B. Liu, and L. Beerhues, "Biosynthesis of the biphenyl phytoalexin aucuparin in Sorbus aucuparia cell cultures treated with Venturia inaequalis", Phytochemistry, vol. 96: Pergamon, pp. 101–109, 2013. Abstract
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Coyne, S., C. Chizzali, M. N. A. Khalil, A. Litomska, K. Richter, L. Beerhues, and C. Hertweck, "Cover Picture: Biosynthesis of the Antimetabolite 6-Thioguanine in Erwinia amylovora Plays a Key Role in Fire Blight Pathogenesis (Angew. Chem. Int. Ed. 40/2013)", Angewandte Chemie International Edition, vol. 52, no. 40: Wiley Online Library, pp. 10391–10391, 2013. Abstract
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Coyne, S., C. Chizzali, M. N. A. Khalil, A. Litomska, K. Richter, L. Beerhues, and C. Hertweck, "Titelbild: Biosynthesis of the Antimetabolite 6-Thioguanine in Erwinia amylovora Plays a Key Role in Fire Blight Pathogenesis (Angew. Chem. 40/2013)", Angewandte Chemie, vol. 125, no. 40: Wiley Online Library, pp. 10583–10583, 2013. Abstract
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2012
Chizzali, C., M. N. A. Khalil, T. Beuerle, W. Schuehly, K. Richter, H. Flachowsky, A. Peil, M. - V. Hanke, B. Liu, and L. Beerhues, "Formation of biphenyl and dibenzofuran phytoalexins in the transition zones of fire blight-infected stems of Malus domestica cv.‘Holsteiner Cox’and Pyrus communis cv.‘Conference’", Phytochemistry, vol. 77: Pergamon, pp. 179–185, 2012. Abstract
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