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Publications - Bioorganic Chemistry

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Publications

Akramov, D. K.; Mamadalieva, N. Z.; Porzel, A.; Hussain, H.; Dube, M.; Akhmedov, A.; Altyar, A. E.; Ashour, M. L.; Wessjohann, L. A.; Sugar containing compounds and biological activities of Lagochilus setulosus Molecules 26, 1755, (2021) DOI: 10.3390/molecules26061755

Phytochemical investigation of the methanolic extract obtained from the aerial parts of Lagochilus setulosus (Lamiaceae) afforded the new compound 1-methoxy-3-O-β-glucopyranosyl-α-l-oliose (1) together with five known glycosides, namely sitosterol-3-O-β-glucoside (2), stigmasterol-3-O-β-glucoside (3), pinitol (4), 6β-hydroxyl-7-epi-loganin (5), and chlorotuberoside (6). The structures of these compounds were elucidated by extensive spectroscopic analyses, especially HR-MS, 1D and 2D NMR spectroscopy. The in vitro cytotoxic activity of the methanolic extract and the isolated compounds was assessed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and crystal violet (CV) staining assays. In addition, the antifungal activities of the components were evaluated against Botrytis cinerea, Septoria tritici, and Phytophthora infestans. The anthelmintic potential was determined against Caenorhabditis elegans nematodes. Neither the extract nor the isolated compounds showed promising activity in all the bioassays.
Publications

Adem, A. A.; Belete, A.; Soboleva, A.; Frolov, A.; Tessema, E. N.; Gebre-Mariam, T.; Neubert, R. H.; Structural characterization of plant glucosylceramides and thecorresponding ceramides by UHPLC-LTQ-Orbitrap mass spectrometry J. Pharm. Biomed. Anal. 192, 113677, (2021) DOI: 10.1016/j.jpba.2020.113677

Ceramides (CERs) play a major role in skin barrier function and direct replacement of depleted skin CERs,due to skin disorder or aging, has beneficial effects in improving skin barrier function and skin hydration.Though, plants are reliable source of CERs, absence of economical and effective method of hydrolysis toconvert the dominant plant sphingolipid, glucosylceramides (GlcCERs), into CERs remains a challenge.This study aims at exploring alternative GlcCERs sources and chemical method of hydrolysis into CERsfor dermal application. GlcCERs isolated from lupin bean (Lupinus albus), mung bean (Vigna radiate) andnaked barley (Hordium vulgare) were identified using ultra high performance liquid chromatographyhyphenated with atmospheric pressure chemical ionization - high resolution tandem mass spectrometer(UHPLC/APCI-HRMS/MS) and quantified with validated automated multiple development-high perfor-mance thin layer chromatography (AMD-HPTLC) method. Plant GlcCERs were hydrolyzed into CERs withmild acid hydrolysis (0.1 N HCl) after treating them with oxidizing agent, NaIO4,and reducing agent,NaBH4. GlcCERs with 4,8-sphingadienine, 8-sphingenine and 4-hydroxy-8-sphingenine sphingoid baseslinked with C14 to C26 -hydroxylated fatty acids (FAs) were identified. Single GlcCER (m/z 714.5520)was dominant in lupin and mung beans while five major GlcCERs species (m/z 714.5520, m/z 742.5829,m/z 770.6144, m/z 842.6719 and m/z 844.56875) were obtained from naked barley. The GlcCERs con-tents of the three plants were comparable. However, lupin bean contains predominantly (> 98 %) a singleGlcCER (m/z 714.5520). Considering the affordability, GlcCER content and yield, lupin bean would bethe preferred alternative commercial source of GlcCERs. CER species bearing 4,8-sphingadienine and 8-sphingenine sphingoid bases attached to C14 to 24 FAs were found after mild acid hydrolysis. CER specieswith m/z 552.4992 was the main component in the beans while CER with m/z 608.5613 was dominantin the naked barley. However, CERs with 4-hydroxy-8-sphingenine sphingoid base were not detected inUHPLC-HRMS/MS study suggesting that the method works for mainly GlcCERs carrying dihydroxy sph-ingoid bases. The method is economical and effective which potentiates the commercialization of plantCERs for dermal application.
Publications

Püllmann, P.; Knorrscheidt, A.; Münch, J.; Palme, P. R.; Hoehenwarter, W.; Marillonnet, S.; Alcalde, M.; Westermann, B.; Weissenborn, M. J.; A modular two yeast species secretion system for the production and preparative application of unspecific peroxygenases Commun. Biol. 4, 562, (2021) DOI: 10.1038/s42003-021-02076-3

AbstractFungal unspecific peroxygenases (UPOs) represent an enzyme class catalysing versatile oxyfunctionalisation reactions on a broad substrate scope. They are occurring as secreted, glycosylated proteins bearing a haem-thiolate active site and rely on hydrogen peroxide as the oxygen source. However, their heterologous production in a fast-growing organism suitable for high throughput screening has only succeeded once—enabled by an intensive directed evolution campaign. We developed and applied a modular Golden Gate-based secretion system, allowing the first production of four active UPOs in yeast, their one-step purification and application in an enantioselective conversion on a preparative scale. The Golden Gate setup was designed to be universally applicable and consists of the three module types: i) signal peptides for secretion, ii) UPO genes, and iii) protein tags for purification and split-GFP detection. The modular episomal system is suitable for use in Saccharomyces cerevisiae and was transferred to episomal and chromosomally integrated expression cassettes in Pichia pastoris. Shake flask productions in Pichia pastoris yielded up to 24 mg/L secreted UPO enzyme, which was employed for the preparative scale conversion of a phenethylamine derivative reaching 98.6 % ee. Our results demonstrate a rapid, modular yeast secretion workflow of UPOs yielding preparative scale enantioselective biotransformations.
Publications

Jänicke, P.; Lennicke, C.; Meister, A.; Seliger, B.; Wessjohann, L. A.; Kaluđerović, G. N.; Fluorescent spherical mesoporous silica nanoparticles loaded with emodin: Synthesis, cellular uptake and anticancer activity Mater. Sci. Eng. C-Mater. Biol. Appl. 119, 111619, (2021) DOI: 10.1016/j.msec.2020.111619

The natural product emodin (EO) exhibits anti-inflammatory, antiangiogenesis and antineoplastic properties in vitro and in vivo. Due to its biological properties as well as its fluorescence, EO can be useful in pharmacology and pharmacokinetics. To enhance its selectivity to cancer cells, EO was loaded into non-fluorescent and novel fluorescent spherical mesoporous nanoparticles bearing N-methyl isatoic anhydride (SNM~M) or lissamine rhodamine B sulfonyl moieties (SNM~L). The propylamine functionalized mesoporous silica nanomaterial (SNM) were characterized by powder X-ray diffraction (XRD), nitrogen gas sorption, scanning electron microscopy (SEM), transmission electron microscopy (TEM), fluorescence spectroscopy, thermogravimetric analysis (TGA) and UV spectroscopy. The cytotoxicity of EO-loaded nanoparticles was tested against the human colon carcinoma cell line HT-29. Non-loaded SNM did not affect cell proliferation, whereas those loaded with EO were at least as efficient as EO alone. It could be shown by fluorescence microscopy that the uptake of silica nanomaterial by the tumor cells occurred within 2 h and the release of EO occurred within 48 h of treatment. Flow cytometry and Western blot analysis showed that SNM containing EO induced apoptosis in HT-29 cells.
Publications

Hussain, W.; Badshah, L.; Ali, A.; Hussain, H.; Hussain, F.; Studies on varying nutrient status of five plants species in pre-reproductive, reproductive and post-reproductive stages, Koh-e-Sufaid range, Kurram valley, Pakistan Pakistan Journal of Botany 53, 1771-1777, (2021) DOI: 10.30848/pjb2021-5(2)

This study was designed to investigate the mineral composition at three phenological stages of some selected fodder forage. Therefore, five taxa viz., Indigofera gerardiana, Tagetes minutia, Rubus fruticosus, Medicago sativa, and Quercus baloot were tested for different minerals such as Mg, K, Na, Ca, Zn, Co, Fe, Cr, Mn and Cu. The highest concentration of macronutrients i.e. Ca (96700 µg/g), Mn (99800 µg/g) were found at post-reproductive phase in Indigofera gerardiana and K (90200 µg/g) was recorded during pre-reproductive phase in Tagetes minutia while the Rubus fruticosus exhibited (17800µg/g) and (59900µg/g) Co and Cu respectively. Similarly, the highest level of Chromium (Cr) recorded (76600µg/g) at reproductive phase in Tagetes minuta, Nickle concentration was recorded maximum i.e. 46400 µg/g at pre-reproductive phase in Rubus fruticosus. Furthermore, Zn contents were (88800 µg/g) at pre-reproductive both in Medicago sativa and Tagetes minuta and subsequently Fe (59300 µg/g) at pre-reproductive phase in Indigofera gerardiana. This study helped in correlating the mineral status of these plant species to their palatability status. The mineral profile of the plants analyzed indicates that mineral levels were as per the required standards and their concentrations were not drastically different from other parts of Pakistan.
Publications

Hussain, H.; Ali, I.; Wang, D.; Hakkim, F. L.; Westermann, B.; Ahmed, I.; Ashour, A. M.; Khan, A.; Hussain, A.; Green, I. R.; Shah, S. T. A.; Glycyrrhetinic acid: a promising scaffold for the discovery of anticancer agents Expert Opinion on Drug Discovery 16, 1497-1516, (2021) DOI: 10.1080/17460441.2021.1956901

Introduction: Oleanane-type pentacyclic triterpenes named glycyrrhetinic acids (GAs) featuring a C-30 carboxylic acid group, are extracted from the licorice (Glycyrrhiza uralensis). Numerous biological properties of GA have been reported and have attracted researchers from all over the world in recent years due to the peculiar GA scaffold-based semisynthetic cytotoxic effects.Areas covered: This review represents the applications of semisynthetic derivatives of GA for the development of future cancer treatments. Included in the review are important structural features of the semisynthetic GAs crucial for cytotoxic effects.Expert opinion: Numerous semisynthetic GA derivatives illustrated excellent cytotoxic effects toward various cancer cells. Notably the C-3(OH) at ring A along with C30-CO2H at ring E as vital structural features, make GA very appealing as a lead scaffold for medicinal chemistry, since these two groups permit the creation of further chemical diversity geared toward improved cytotoxic effects. Furthermore, numerous GA derivatives have been synthesized and indicate that compounds featuring cyanoenone moieties in ring A, or compounds having the amino group or nitrogen comprising heterocycles and hybrids thereof, illustrate more potent cytotoxicity. Furthermore, GA has a great capability to be conjugated with other anticancer molecules to synergistically enhance their combined cytotoxicity.
Publications

Hussain, H.; Mamadalieva, N. Z.; Ali, I.; Elizbit, .; Green, I. R.; Wang, D.; Zou, L.; Simal-Gandara, J.; Cao, H.; Xiao, J.; Fungal glycosides: Structure and biological function Trends in Food Science & Technology 110, 611-651, (2021) DOI: 10.1016/j.tifs.2021.02.029

Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target.Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units.Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.
Publications

Hussain, H.; Nazir, M.; Saleem, M.; Al-Harrasi, A.; Elizbit, .; Green, I. R.; Fruitful decade of fungal metabolites as anti-diabetic agents from 2010 to 2019: emphasis on α-glucosidase inhibitors Phytochem. Rev. 20, 145-179, (2021) DOI: 10.1007/s11101-020-09733-1

AbstractIn recent years the prevalence of diabetes has increased globally and by 2040 the number of diabetic people has been estimated to increase to 642 million. Various classes of drugs are available to treat Type ll diabetes. However, these drugs are associated with certain side effects. α-Glucosidase is an intriquing target enzyme to treat Type II diabetes, and α-glucosidase inhibitors are considered as first-line drugs for Type ll patients. Fungi, in general, produce natural products with some amazing chemical diversity and many fungal metabolites have illustrated a wide range of biological and pharmacological effects. In this review the focus is on describing the α-glucosidase effects and their potential as anti-diabetic agents of various metabolites isolated from fungi.
Publications

Hussain, H.; Ali, I.; Wang, D.; Hakkim, F. L.; Westermann, B.; Rashan, L.; Ahmed, I.; Green, I. R.; Boswellic acids: privileged structures to develop lead compounds for anticancer drug discovery Expert Opinion on Drug Discovery 16, 851-867, (2021) DOI: 10.1080/17460441.2021.1892640

Introduction: Cancer has been identified to be the second major cause of death internationally as exemplified by ca. 9.6 million deaths in 2018 along with ca. 18 million new patients in 2018 that have been recorded. Natural boswellic acids (BAs) and their source, frankincense, have been reported to possess in vitro and in vivo anticancer effects toward various cancer cells.Areas covered: This comprehensive review focuses on the importance of boswellic acids (BAs) for the establishment of future treatments of cancer. Moreover, potent semisynthetic derivatives of BAs have been described along with their mode of action. In addition, important structural features of the semisynthetic BAs required for cytotoxic effects are also discussed.Expert opinion: Numerous semisynthetic BAs illustrate excellent cytotoxic effects. Of note, compounds bearing cyanoenone moieties in ring A, endoperoxides and hybrids display increased and more potent cytotoxic effects compared with other semisynthetic BAs. Moreover, BAs have the potential to conjugate or couple with other anticancer compounds to synergistically increase their combined anticancer effects. In addition, to get derived BAs to become lead anticancer compounds, future research should focus on the preparation of ring A cyanoenones, endoperoxides, and C-24 amide analogs.
Publications

Hou, Y.; Ali, I.; Li, Z.; Sulaiman, A.; Aziz, S.; Chen, L.; Hussain, H.; Cui, L.; Wang, D.; Zheng, X.; Separation of constituents from Bergenia stracheyi (Hook. F. & Thoms.) Engl. by high‐speed countercurrent chromatography with elution mode and its antidiabetic and antioxidant in vitro evaluation J Sep Sci 44, 767-776, (2021) DOI: 10.1002/jssc.202000999

Diabetes, a metabolic disorder, is caused by a high blood sugar level. Diabetes isan increasing health issue and search for potent antidiabetic agents is desirable.Owing to its ethnomedicinal value, the Himalayan perennial herb Bergenia stracheyi(Hook. f. & Thoms.) Engl. (Saxifragaceae Juss) is used to treat diabetes.Herein, an efficient high-speed countercurrent chromatography with elutionmode is reported for separation of active compounds from B. stracheyi. In currentinvestigation, six main compounds including β-arbutin (1), bergenin (2), 6-O-galloylarbutin (3), gallic acid (4), 11-O-galloylbergenin (5), and (-)-epicatechin3-O-gallate (6) with above 95% purity were efficiently separated in a singlerun using biphasic tert-butyl methyl ether/n-butanol/methanol/water (1:3:1:5,v/v/v/v) solvent system. The structures of these compounds were characterizedusing spectral techniques and compared with the literature. Antidiabetic andantioxidant activities evaluation of the study samples showed that β-arbutin (1)and 6-O-galloylarbutin (3) have a significant protective effect, especially at highdose against hydrogen peroxide induced oxidative injury. Our results might helpfurther in-depth phytochemical and biological evaluation studies in search ofpotent antidiabetic compounds from B. stracheyi.
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