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2024
Ghezzi, D., L. Salvi, P. E. Costantini, A. Firrincieli, M. Iorio, E. Lopo, M. Sosio, A. H. Elbanna, Z. G. Khalil, R. J. Capon, et al., Ancient and remote quartzite caves as a novel source of culturable microbes with biotechnological potential, , vol. 286, pp. 127793, 2024. AbstractWebsite

Quartzite caves located on table-top mountains (tepuis) in the Guyana Shield, are ancient, remote, and pristine subterranean environments where microbes have evolved peculiar metabolic strategies to thrive in silica-rich, slightly acidic and oligotrophic conditions. In this study, we explored the culturable fraction of the microbiota inhabiting the (ortho)quartzite cave systems in Venezuelan tepui (remote table-top mountains) and we investigated their metabolic and enzymatic activities in relation with silica solubilization and extracellular hydrolytic activities as well as the capacity to produce antimicrobial compounds. Eighty microbial strains were isolated with a range of different enzymatic capabilities. More than half of the isolated strains performed at least three enzymatic activities and four bacterial strains displayed antimicrobial activities. The antimicrobial producers Paraburkholderia bryophila CMB_CA002 and Sphingomonas sp. MEM_CA187, were further analyzed by conducting chemotaxonomy, phylogenomics, and phenomics. While the isolate MEM_CA187 represents a novel species of the genus Sphingomonas, for which the name Sphingomonas imawarii sp. nov. is proposed, P. bryophila CMB_CA002 is affiliated with a few strains of the same species that are antimicrobial producers. Chemical analyses demonstrated that CMB_CA002 produces ditropolonyl sulfide that has a broad range of activity and a possibly novel siderophore. Although the antimicrobial compounds produced by MEM_CA187 could not be identified through HPLC-MS analysis due to the absence of reference compounds, it represents the first soil-associated Sphingomonas strain with the capacity to produce antimicrobials. This work provides first insights into the metabolic potential present in quartzite cave systems pointing out that these environments are a novel and still understudied source of microbial strains with biotechnological potential.

Elbanna, A. H., S. Abdelghany, S. Alseekh, A. R. Fernie, and M. A. Farag, Seasonal and taxa impact on edible sea cucumber metabolome as analyzed via a multiplex approach of mass spectroscopy-based metabolomics, , vol. 57, pp. 103456, 2024. AbstractWebsite

Sea cucumbers, belonging to class Holothuroidea, are marine invertebrates with substantial bioactive compounds and nutritive value. This study presents a multiplex metabolomics approach to dissect between winter and summer samples of two Red Sea cucumbers: Holothuria atra and Actinopyga crassa. LC-MS and GC-MS followed by multivariate data analyses were employed for metabolites profiling and seasonal biomarkers assignment for each species. A total of 314 metabolites were annotated in both species belonging to amino acids, sugars, sugar alcohols, acids, triacylglycerides (TAGs), phospholipids, lyso-phospholipids, sphingolipids, phosphatidylcholines, diacylglycerols, different glycolipids, and others, adding to the nutritive value of sea cucumber. GC-MS analysis revealed for amino acids i.e., alanine as the main polar primary metabolite class in sea cucumbers. LC-MS analysis targeting non-polar metabolites revealed TAGs as the main class followed by phospholipids and lyso-phospholipids. Multivariate orthogonal partial least square discriminant analysis (OPLS-DA) revealed that A. crassa is enriched in alanine and lactic acid than H. atra versus higher levels of pyroglutamic acid and ethanolamine and TAGs in the later. Summer A. crassa was distinguished from its winter specimen by its higher TAGs, glycine and glycerol levels versus enrichment of winter samples in lyso-phospholipids, isoleucine, and proline. Such metabolomic study revealed for A. crassa and H. atra richness in nutrient metabolites, alongside collection season effect on their amino acids and lipids profiles.

2022
Dewa, A. A., Z. G. Khalil, A. H. Elbanna, and R. J. Capon, "Chrysosporazines Revisited: Regioisomeric Phenylpropanoid Piperazine P-Glycoprotein Inhibitors from Australian Marine Fish-Derived Fungi", Molecules, vol. 27, issue 10, pp. 3172, 2022. Abstract

A library of fungi previously recovered from the gastrointestinal tract (GIT) of several fresh, commercially sourced Australian mullet fish was re-profiled for production of a rare class of phenylpropanoid piperazine alkaloids (chrysosporazines) using an integrated platform of; (i) miniaturized 24-well plate cultivation profiling (MATRIX), (ii) UPLC-DAD and UPLC-QTOF-MS/MS (GNPS) chemical profiling, and; (iii) precursor directed biosynthesis to manipulate in situ biosynthetic performance and outputs; to detect two new fungal producers of chrysosporazines. Chemical analysis of an optimized PDA solid phase cultivation of Aspergillus sp. CMB-F661 yielded the new regioisomeric chrysosporazine T (1) and U (2), while precursor directed cultivation amplified production and yielded the very minor new natural products azachrysosporazine T1 (3) and U1 (4), and the new unnatural analogues neochrysosporazine R (5) and S (6). Likewise, chemical analysis of an optimized M1 solid phase cultivation of Spiromastix sp. CMB-F455 lead to the GNPS detection of multiple chrysosporazines and brasiliamides, and the isolation and structure elucidation of chrysosporazine D (7) and brasiliamide A (8). Access to new chrysosporazine regioisomers facilitated structure activity relationship investigations to better define the chrysosporazine P-glycoprotein (P-gp) inhibitory pharmacophore, which is exceptionally potent at reversing doxorubrin resistance in P-gp over expressing colon carcinoma cells (SW600 Ad300).

Dewa, A. A., Z. G. Khalil, A. H. Elbanna, and R. J. Capon, "Chrysosporazines Revisited: Regioisomeric Phenylpropanoid Piperazine P-Glycoprotein Inhibitors from Australian Marine Fish-Derived Fungi", Molecules, vol. 27, issue 10, 2022. Abstract

A library of fungi previously recovered from the gastrointestinal tract (GIT) of several fresh, commercially sourced Australian mullet fish was re-profiled for production of a rare class of phenylpropanoid piperazine alkaloids (chrysosporazines) using an integrated platform of; (i) miniaturized 24-well plate cultivation profiling (MATRIX), (ii) UPLC-DAD and UPLC-QTOF-MS/MS (GNPS) chemical profiling, and; (iii) precursor directed biosynthesis to manipulate in situ biosynthetic performance and outputs; to detect two new fungal producers of chrysosporazines. Chemical analysis of an optimized PDA solid phase cultivation of Aspergillus sp. CMB-F661 yielded the new regioisomeric chrysosporazine T (1) and U (2), while precursor directed cultivation amplified production and yielded the very minor new natural products azachrysosporazine T1 (3) and U1 (4), and the new unnatural analogues neochrysosporazine R (5) and S (6). Likewise, chemical analysis of an optimized M1 solid phase cultivation of Spiromastix sp. CMB-F455 lead to the GNPS detection of multiple chrysosporazines and brasiliamides, and the isolation and structure elucidation of chrysosporazine D (7) and brasiliamide A (8). Access to new chrysosporazine regioisomers facilitated structure activity relationship investigations to better define the chrysosporazine P-glycoprotein (P-gp) inhibitory pharmacophore, which is exceptionally potent at reversing doxorubrin resistance in P-gp over expressing colon carcinoma cells (SW600 Ad300).

Dewa, A. A., A. H. Elbanna, Z. G. Khalil, and R. J. Capon, "Neochrysosporazines: Precursor-Directed Biosynthesis Defines a Marine-Derived Fungal Natural Product P-Glycoprotein Inhibitory Pharmacophore", Journal of Medicinal ChemistryJournal of Medicinal Chemistry, vol. 65, issue 3: American Chemical Society, pp. 2610 - 2622, 2022. AbstractWebsite
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Dewa, A. A., A. H. Elbanna, Z. G. Khalil, and R. J. Capon, "Neochrysosporazines: Precursor-Directed Biosynthesis Defines a Marine-Derived Fungal Natural Product P‑Glycoprotein Inhibitory Pharmacophore", Journal of Medicinal Chemistry, vol. 65, issue 3, pp. 2610-2622, 2022. Abstract

Upregulation of ATP binding cassette (ABC) transporter efflux pumps (i.e. P-glycoprotein, P-gp) can impart multidrug resistance, rendering many chemotherapeutics ineffective and seriously limiting treatment regimes. While ABC transporters remain an attractive target for therapeutic intervention, the development of clinically useful small-molecule inhibitors has proved challenging. In this report, we describe the structure–activity relationship (SAR) analysis of a newly discovered P-gp inhibitory pharmacophore, phenylpropanoid piperazine chrysosporazines, produced by co-isolated marine-derived fungi. In the absence of any total syntheses, we apply an innovative precursor-directed biosynthesis strategy that successfully repurposed fungal biosynthetic output, allowing us to isolate, characterize, and identify the structurally diverse neochrysosporazines A–Q. SAR analysis utilizing all known (and new) neochrysosporazines, chrysosporazines, and azachrysosporazines, plus semi-synthetic analogues, established the key structure requirements for the P-gp inhibitory pharmacophore, and, in addition, identified non-essential sites that allow for the design of affinity and other conjugated probes.

2021
Salim, A. A., Z. G. Khalil, A. H. Elbanna, T. Wu, and R. J. Capon, "Methods in Microbial Biodiscovery", Marine Drugs, vol. 19, issue 9, pp. 503, 2021. Abstract

This review presents an account of the microbial biodiscovery methodology developed and applied in our laboratory at The University of Queensland, Institute for Molecular Bioscience, with examples drawn from our experiences studying natural products produced by Australian marine-derived (and terrestrial) fungi and bacteria.

Elbanna, A. H., Z. G. Khalil, P. V. Bernhardt, and R. J. Capon, "Neobulgarones Revisited: Anti and Syn Bianthrones from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD22.", Journal of natural products, vol. 84, issue 3, pp. 762–770, 2021. Abstract

We report on the chemical analysis of a mud dauber wasp nest-associated fungus, Penicillium sp. CMB-MD22, leading to the discovery and structure elucidation of three known (1-3) and two new (4 and 5) anthrones, and a family of new and known bianthrones, neobulgarones 6-23. Detection and structure elucidation of 1-23 was supported by detailed spectroscopic analysis, as well as chemical (thermal) transformations, and global natural products social (GNPS) molecular networking. An empirical approach using HPLC retention times was effective at differentiating anti from syn bianthrone isomers, while a facile thermal equilibration was shown to favor anti over syn isomers. The neobulgarones 6-23 are natural products, and a crude extract rich in 6-23 exhibits selective antifungal activity against a co-isolated mud dauber wasp nest-associated fungus, suggestive of a possible ecological role as an antifungal chemical defense.

Khushi, S., A. A. Salim, A. H. Elbanna, L. Nahar, and R. J. Capon, "New from Old: Thorectandrin Alkaloids in a Southern Australian Marine Sponge, Thorectandra choanoides (CMB-01889)", Marine Drugs, vol. 19, issue 2, pp. 97, 2021. Abstract

Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical fractionation followed by detailed spectroscopic analysis led to the discovery of a new tryptophan-derived alkaloid, thorectandrin A (1), with the GNPS cluster revealing a halo of related alkaloids 1a–1n. In considering biosynthetic origins, we propose that Thorectandrachoanoides (CMB-01889) produces four well-known alkaloids, 6-bromo-1′,8-dihydroaplysinopsin (2), 6-bromoaplysinopsin (3), aplysinopsin (4), and 1′,8-dihydroaplysinopsin (10), all of which are susceptible to processing by a putative indoleamine 2,3-dioxygenase-like (IDO) enzyme to 1a–1n. Where the 1′,8-dihydroalkaloids 2 and 10 are fully transformed to stable ring-opened thorectandrins 1 and 1a–1b, and 1h–1j, respectively, the conjugated precursors 3 and 4 are transformed to highly reactive Michael acceptors that during extraction and handling undergo complete transformation to artifacts 1c–1g, and 1k–1n, respectively. Knowledge of the susceptibility of aplysinopsins as substrates for IDOs, and the relative reactivity of Michael acceptor transformation products, informs our understanding of the pharmaceutical potential of this vintage marine pharmacophore. For example, the cancer tissue specificity of IDOs could be exploited for an immunotherapeutic response, with aplysinopsins transforming in situ to Michael acceptor thorectandrins, which covalently bind and inhibit the enzyme.

Elbanna, A. H., Z. G. Khalil, and R. J. Capon, "Oxandrastins: Antibacterial Meroterpenes from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD14", Molecules, vol. 26, issue 23, pp. 7144, 2021. Abstract

The ethyl acetate extract of an ISP-2 agar cultivation of the wasp nest-associated fungus Penicillium sp. CMB-MD14 exhibited promising antibacterial activity against vancomycin-resistant enterococci (VRE), with a bioassay guided chemical investigation yielding the new meroterpene, oxandrastin A (1), the first andrastin-like metabolite with an extra oxygenation at C-2. A culture media optimisation strategy informed a scaled-up rice cultivation that yielded 1, together with three new oxandrastins B–D (2–4), two known andrastins C (5) and F (6), and a new meroterpene of the austalide family, isoaustalide F (7). Structures of 1–7 were assigned based on detailed spectroscopic analysis and chemical interconversion. A GNPS molecular networking analysis of the rice cultivation extract detected the known austalides B (8), H (9), and H acid (10), tentatively identified based on molecular formulae and co-clustering with 7. That the anti-VRE properties of the CMB-MD14 extract were exclusively attributed to 1 (IC50 6.0 µM, MIC99 13.9 µM), highlights the importance of the 2-OAc and 3-OAc moieties to the oxandrastin anti-VRE pharmacophore.

Elbanna, A. H., A. A. Dewa, Z. G. Khalil, and R. J. Capon, "Precursor-Directed Biosynthesis Mediated Amplification of Minor Aza Phenylpropanoid Piperazines in an Australian Marine Fish-Gut-Derived Fungus, Chrysosporium sp. CMB-F214", Marine Drugs, vol. 19, issue 9, pp. 478, 2021. Abstract

Chemical analysis of an M1 agar plate cultivation of a marine fish-gut-derived fungus, Chrysosporium sp. CMB-F214, revealed the known chrysosporazines A–D (11–14) in addition to a suite of very minor aza analogues 1–6. A microbioreactor (MATRIX) cultivation profiling analysis failed to deliver cultivation conditions that significantly improved the yields of 1–6; however, it did reveal that M2 agar cultivation produced the new natural product 15. A precursor-directed biosynthesis strategy adopting supplementation of a CMB-F214 M1 solid agar culture with sodium nicotinate enhanced production of otherwise inaccessible azachrysposorazines A1 (1), A2 (2), B1 (3), C1 (4), C2 (5) and D1 (6), in addition to four new chrysosporazines; chrysosporazines N–P (7–9) and spirochrysosporazine A (10). Structures inclusive of absolute configurations were assigned to 1–15 based on detailed spectroscopic and chemical analyses, and biosynthetic considerations. Non-cytotoxic to human carcinoma cells, azachrysosporazies 1–5 were capable of reversing doxorubicin resistance in P-glycoprotein (P-gp)-overexpressing human colon carcinoma cells (SW620 Ad300), with optimum activity exhibited by the C-2′ substituted analogues 3–5.

2020
Mohamed, O. G., A. A. Salim, Z. G. Khalil, A. H. Elbanna, P. V. Bernhardt, and R. J. Capon, "Chrysosporazines F-M: P-Glycoprotein Inhibitory Phenylpropanoid Piperazines from an Australian Marine Fish Derived Fungus, Chrysosporium sp. CMB-F294.", Journal of natural products, vol. 83, issue 2, pp. 497 - 504, 2020-02-28. Abstract

Chemical analysis of the fungus Chrysosporium sp. CMB-F294 isolated from the gastrointestinal tract of a market-purchased specimen of Mugil mullet yielded eight new alkaloids, belonging to a rare class of phenylpropanoid piperazines. Chrysosporazines F-M (1-8) occur as an equilibrium mixture of acetamide rotamers and feature unprecedented carbocyclic and heterocyclic scaffolds. Structures inclusive of absolute configuration were assigned by detailed spectroscopic analysis, supported by biosynthetic considerations. Structure-activity relationship studies determined that selected chrysosporazines were promising noncytotoxic inhibitors of the multidrug resistance efflux pump P-glycoprotein (P-gp), capable of reversing doxorubicin resistance in P-gp-overexpressing human colon carcinoma cells (SW620 Ad300). Chrysosporazine F (1) was particularly noteworthy, with a 2.5 μM cotreatment inducing a doxorubicin gain in sensitivity (GS 14) > 2-fold that of the positive control verapamil (GS 6.1).

Khushi, S., A. A. Salim, A. H. Elbanna, L. Nahar, P. V. Bernhardt, and R. J. Capon, "Dysidealactams and Dysidealactones: Sesquiterpene Glycinyl-Lactams, Imides, and Lactones from a Dysidea sp. Marine Sponge Collected in Southern Australia", Journal of Natural Products, vol. 83, issue 5, pp. 1577-1584, 2020. Abstract

A GNPS molecular networking approach mapped a library of 960 southern Australian marine sponges and prioritized Dysidea sp. (CMB-01171) for chemical investigation. Although the published natural products literature on Australian Dysidea sponges extends back over half a century and suffers from the perception of being near exhausted, fractionation of Dysidea sp. (CMB-01171) led to the discovery of a family of 10 new biosynthetically and chemically related sesquiterpenes. Detailed spectroscopic analysis guided structure elucidation identified dysidealactams A-F (1-6), dysidealactones A and B (7 and 8), and two solvolysis artifacts, 9 and 10. The dysidealactams A-D (1-4) incorporate a rare glycinyl-lactam functionality, while dysidealactam E (5) is particularly noteworthy in incorporating an unprecedented glycinyl-imide moiety. In addition to expanding knowledge of Dysidea natural products, this study demonstrates the value of applying GNPS molecular networking to map chemical diversity and prioritize the selection of marine sponge extracts for more detailed chemical analysis.

Liu, X., P. Carr, M. G Gardiner, M. G. Banwell, A. H. Elbanna, Z. G. Khalil, and R. J. Capon, "Levoglucosenone and Its Pseudoenantiomer iso -Levoglucosenone as Scaffolds for Drug Discovery and Development", ACS Omega, vol. 5, issue 23, pp. 13926-13939, 2020. Abstract

The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported.

2019
Elbanna, A. H., Z. G. Khalil, P. V. Bernhardt, and R. J. Capon, "Chrysosporazines A-E: P-Glycoprotein Inhibitory Piperazines from an Australian Marine Fish Gastrointestinal Tract-Derived Fungus, Chrysosporium sp. CMB-F214.", Organic Letters, vol. 21, issue 19, pp. 8097 - 8100, 2019-10-04. Abstract

Chemical analysis of Chrysosporium sp. CMB-F214, yielded five new piperazines, chrysosporazines A-E (1-5), with structures assigned by spectroscopic and X-ray analyses and biosynthetic considerations. The chrysosporazines 2-5 exist as an equilibrium of major and minor N-acyl rotamers, while 1-3 incorporate an unprecedented hexahydro-6H-pyrazino[1,2-b]isoquinolin-6-one scaffold. The noncytotoxic chrysosporazines reverse doxorubicin drug resistance in P-glycoprotein overexpressing colon carcinoma cells (SW620 Ad300), with 2 delivering a comparable gain in sensitivity to the positive control, verapamil.

ElBanna, A. H., Z. G. Khalil, P. V. Bernhardt, and R. J. Capon, "Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi", Marine drugs, vol. 17, issue 8, pp. 475, 2019.
2017
Elbanna, A. H., M. M. Nooh, E. A. Mahrous, A. E. Khaleel, and T. S. El Alfy, "Extract of Bauhinia vahlii Shows Antihyperglycemic Activity, Reverses Oxidative Stress, and Protects against Liver Damage in Streptozotocin-induced Diabetic Rats", Pharmacognosy Magazine, vol. 13, issue Suppl 3, pp. S607-S612, 2017. Abstract

Several studies have affirmed the effectiveness of some Bauhinia plants as antihyperglycemic agents. We investigated the possible effect of Bauhinia vahlii leaves extract in reducing hyperglycemia and reversing signs of organ damage associated with diabetes in streptozotocin (STZ) rat model. Both polar fraction of the B. vahlii leaves (defatted ethanolic extract [DEE]) and nonpolar fraction (n-hexane extract) were evaluated in vitro for α-glucosidase inhibition and 2,2-diphenyl-1-picrylhydrazyl radical scavenging potential. DEE was selected for further in vivo studies and was administered at two doses, i.e., 150 or 300 mg/kg to STZ-diabetic rats for 4 weeks. Only DEE exhibited in vitro antioxidant and antihyperglycemic activities and its oral administration at both dose levels resulted in significant reduction in fasting blood glucose and glycated hemoglobin. Furthermore, signs of oxidative stress as indicated by hepatic reduced glutathione, nitric oxide, and malondialdehyde levels were completely reversed. In addition, histopathological examination and measurement of serum aspartate transaminase and alanine transaminase levels showed that DEE protected the liver from signs of liver pathogenesis when compared to diabetic untreated animals and those treated with metformin. Phytochemical analysis of DEE showed high flavonoids content with quercitrin as the major constituent along with other quercetin glycosides. This study strongly highlights the possible beneficial effect of B. vahlii leaves extract in relieving hyperglycemia and liver damage in STZ-diabetic rats and recommends further investigation of the value of quercetin derivatives in controlling diabetes and ameliorating liver damage associated with it. The polar fraction of the Bauhinia vahlii leaves (defatted ethanolic extract [DEE]) exhibited both in vitro antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl scavenging assay and strong α-glucosidase inhibition while the nonpolar fraction (n-hexane extract) failed to show any activity in both assays. DEE was further investigated in streptozotocin-induced diabetic rat model where oral administration of DEE at 2 doses (150 and 300 mg/kg) for 4 weeks resulted in significant reduction in fasting blood glucose and glycated hemoglobin and reversal of oxidative stress signs as indicated by measurement of hepatic reduced glutathione, nitric oxide, and malondialdehyde levels. In addition, histopathological examination and measurement of serum aspartate transaminase and alanine transaminase levels showed that DEE protected the liver from signs of pathogenesis observed in diabetic untreated rats. Phytochemical analysis of DEE showed high flavonoid content with quercitrin as the major constituent (62.9 ± 0.18 mg/mg). The polar fraction of the Bauhinia vahlii leaves (defatted ethanolic extract [DEE]) exhibited both in vitro antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl scavenging assay and strong α-glucosidase inhibition while the nonpolar fraction (n-hexane extract) failed to show any activity in both assays. DEE was further investigated in streptozotocin-induced diabetic rat model where oral administration of DEE at 2 doses (150 and 300 mg/kg) for 4 weeks resulted in significant reduction in fasting blood glucose and glycated hemoglobin and reversal of oxidative stress signs as indicated by measurement of hepatic reduced glutathione, nitric oxide, and malondialdehyde levels. In addition, histopathological examination and measurement of serum aspartate transaminase and alanine transaminase levels showed that DEE protected the liver from signs of pathogenesis observed in diabetic untreated rats. Phytochemical analysis of DEE showed high flavonoid content with quercitrin as the major constituent (62.9 ± 0.18 mg/mg). Abbreviations used: ALT: Alanine transaminase, AST: Aspartate transaminase, DEE: Defatted ethanol extract, DPPH: 2,2-diphenyl-1-picrylhydrazyl, FBG: Fasting blood glucose, GAE: Gallic acid equivalent, GSH: Reduced glutathione, Hb1Ac: Glycated hemoglobin, HE: Hexane extract MDA: Malondialdehyde, QE: Quercetin equivalent, STZ: Streptozotocin, TAC: Total antioxidant capacity.

2016
Elbanna, A. H., E. A. Mahrous, A. E. Khaleel, and T. S. El-Alfy, "Chemical investigation of Bauhinia vahlii Wight & Arnott. leaves grown in Egypt", International Journal of Pharmacy and Pharmaceutical sciences, vol. 8, issue 6, pp. 269-272, 2016.
2015
Farag, M. A., A. E. M. Sayed, A. el Banna, and S. Ruehmann, "Metabolomics reveals distinct methylation reaction in MeJA elicited Nigella sativa callus via UPLC–MS and chemometrics", Plant Cell, Tissue and Organ Culture (PCTOC), vol. 122, issue 2, pp. 453-463, 2015. Abstract

Cell suspension cultures are now recognized as important model for studying natural products biosynthesis and functional genomics. Nevertheless, very few studies of metabolic comparisons between cell cultures (callus) and original plants have been reported, even though the biological identity of cultured cells with the normally grown plant is of great importance. In this study, an MS-based metabolomic approach was used to compare the natural products profile of intact Nigella sativa seeds versus callus . N. sativa has been used for centuries in traditional medicine for several purposes. Its phytochemical components comprise, among others, alkaloids, saponins, flavonoids and fatty acids. Ultra performance liquid chromatography coupled to ultraviolet photodiode array detection and high resolution q-TOF mass spectrometry (UPLC–PDA–MS) was utilized to analyze the secondary product metabolome of N. sativa callus, with a total of 74 metabolites including five flavonoids, 13 hydroxycinnamates, an alkaloid, saponin and 14 fatty acids. Callus maintained the capacity to produce N. sativa phenolic subclasses, with hydroxycinnamates amounting for the major secondary metabolites in callus. Alkaloids, major constituents in Nigella genus, were detected in callus though with qualitative and quantitative differences from seed tissue. Methyl jasmonate (MeJA) elicitation effect was assessed on callus with the aim of increasing secondary metabolites production. Metabolite profiles were subjected to principal component analysis and orthogonal projection to latent structures-discriminant analysis to evaluate MeJA effect. Results revealed that MeJA led to O-methylation reaction induction yielding O-feruloylquinic acid from O-caffeoylquinic acid, in addition to a methylated disaccharide. The work extends our knowledge regarding hydroxycinnamates biosynthesis, regulation and on metabolic engineering future efforts to increase its production as potential phytoalexin in N. sativa.

Elbanna, A. H., E. A. Mahrous, A. E. Khaleel, and T. S. El-Alfy, In-vitro anti-hyperglycemic and anti-oxidant activities of Bauhinia vahlii Wight & Arnott. growing in Egypt, , 2015.
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