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Publikationen - Natur- und Wirkstoffchemie

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Publikation

Binimelis-Salazar, J.; CASANOVA-KATNY, A.; Arnold, N.; Lima, C. A.; Norambuena, H. V.; González-Rocha, G.; Palfner, G.; Diversity and host relationships of the mycoparasite Sepedonium (Hypocreales, Ascomycota) in temperate central Chile Microorganisms 9, 2261, (2021) DOI: 10.3390/microorganisms9112261

We present the first major survey of regional diversity, distribution and host-association of Sepedonium. Whereas the rather scarce worldwide records of this mycoparasitic fungus suggested no specific distribution pattern of most species before, we provide new evidence of endemic and specific host-parasite guilds of Sepedonium in Southern South America, including the description of a new species. The corresponding inventory was performed in temperate central Chile. The regional landscape, a mosaic of exotic timber plantations and remnants of native Nothofagus forests, facilitates a unique combination of endemic and adventitious Boletales hosts. During a two-year survey, 35 Sepedonium strains were isolated and cultured from infected basidiomata of allochthonous Chalciporus piperatus, Paxillus involutus, Rhizopogon spp. and Suillus spp., as well as from the native Boletus loyita, B. loyo, B. putidus and Gastroboletus valdivianus. Taxonomic diagnosis included morphology of conidia and conidiophores, sequences of ITS, RPB2 and EF1 molecular markers and characteristics of in vitro cultures. Phylogenetic reconstructions were performed using Bayesian methods. Four Sepedonium species could be identified and characterized, viz.: S. ampullosporum, S. chrysospermum, S. laevigatum and the newly described species S. loyorum. The most frequent species on introduced Boletales was S. ampullosporum, followed by S. chrysospermum and S. laevigatum. S. loyorum sp. nov. was found exclusively on native boletacean hosts, separated from its closest relative S. chalcipori by micromorphological and molecular attributes. Species descriptions and identification keys are provided. Ecological and biogeographical aspects of endemic and allochthonous symbiotic units consisting of mycoparasite, ectomycorrhizal fungal host and respective mycorrhizal tree are discussed.
Publikation

Bini Araba, A.; Ur Rehman, N.; Al-Araimi, A.; Al-Hashmi, S.; Al-Shidhani, S.; Csuk, R.; Hussain, H.; Al-Harrasi, A.; Zadjali, F.; New derivatives of 11-keto-β-boswellic acid (KBA) induce apoptosis in breast and prostate cancers cells Nat. Prod. Res. 35, 707-716, (2021) DOI: 10.1080/14786419.2019.1593165

A series of new 11-keto-β-boswellic acid were partially-synthesized by modifying the hydroxyl and carboxylic acid functional groups of ring A. The structures of the new analogs were confirmed by detailed spectral data analysis. Compounds 4, 5 and 9 exhibited potent anti-cancer results against two human tumor cancer cell lines having IC50 value of MCF-7 (breast) and LNCaP (prostate): 123.6, 9.6 and 88.94 μM and 9.6, 44.12 and 12.03 μM, respectively. Additionally, a maximum nuclear fragmentation was observed for 4 (78.44%) in AKBA treated cells after 24 hr followed by 5 and 9 with (74.25 and 66.9% respectively). This study suggests that the presence of hydrazone functionality (4 and 9) has effectively improved the potency of AKBA. Interestingly, compound 5 with a lost carboxylic acid group of ring A showed comparable potent activity. Highly selective AKBA requires further modification to improve its bioavailability and solubility inside the cancer cells.
Publikation

Bibi, S. D.; Baig, S. A.; Zeb, I.; Ali, M.; Shams, D. F.; Nawab, J.; Yosifova Aneva, I.; Hussain, H.; Xu, X.; Implication and evaluations of indoor soot particles from domestic fuel energy sources using characterization techniques in northern Pakistan Microsc. Res. Tech. 84, 3161-3170, (2021) DOI: 10.1002/jemt.23873

Soot particles emitted from the burning of solid fuel sources in the households carry important environmental and public health implications. In this study, the indoor soot particles released from firewood, cow dung, and bagasse burning at households of selected rural areas of Khyber Pakhtunkhwa province of Pakistan were investigated by characterization analyses to study its morphological and elemental compositions. Results demonstrated diverse compositions of soot particles from each fuel source. The surface areas of soot particles emitted by the firewood, cow dung, and bagasse were about 0.3, 0.4, and 8.64 m2 g−1, respectively. For the soot particles emitted by the firewood burning, the major functional groups for aromatic compounds were C═C at the 1,431–1,599 at 1,000–2,000 cm−1. The absorbance rate of alkanes was about 1,599–1,431 at 1,000–2,000 cm−1. However, silicon band vibration was more prominent in bagasse soot particles as compared to other samples. The emission of soot particles with high surface area in the atmosphere could provide an elevated adsorption sites for atmospheric pollution and trap more energy resulting in increased atmospheric temperature. Findings from the present study suggest that current households\' fuel combustion practices significantly contribute to increase the particulate matter in the atmosphere and possible enhance climate change phenomenon and related disasters in northern Pakistan.
Publikation

Bascuñana, P.; Brackhan, M.; Pahnke, J.; Machine learning-supported analyses improve quantitative histological assessments of amyloid-β deposits and activated Microglia J. Alzheimers Dis. 79, 597-605, (2021) DOI: 10.3233/JAD-201120

Background: Detailed pathology analysis and morphological quantification is tedious and prone to errors. Automatic image analysis can help to increase objectivity and reduce time. Here, we present the evaluation of the DeePathology STUDIO™ for automatic analysis of histological whole-slide images using machine learning/artificial intelligence. Objective: To evaluate and validate the use of DeePathology STUDIO for the analysis of histological slides at high resolution. Methods: We compared the DeePathology STUDIO and our current standard method using macros in AxioVision for the analysis of amyloid-β (Aβ) plaques and microglia in APP-transgenic mice at different ages. We analyzed density variables and total time invested with each approach. In addition, we correlated Aβ concentration in brain tissue measured by ELISA with the results of Aβ staining analysis. Results: DeePathology STUDIO showed a significant decrease of the time for establishing new analyses and the total analysis time by up to 90%. On the other hand, both approaches showed similar quantitative results in plaque and activated microglia density in the different experimental groups. DeePathology STUDIO showed higher sensitivity and accuracy for small-sized plaques. In addition, DeePathology STUDIO allowed the classification of plaques in diffuse- and dense-packed, which was not possible with our traditional analysis. Conclusion: DeePathology STUDIO substantially reduced the effort needed for a new analysis showing comparable quantitative results to the traditional approach. In addition, it allowed including different objects (categories) or cell types in a single analysis, which is not possible with conventional methods.
Publikation

Baig, M. W.; Fatima, H.; Akhtar, N.; Hussain, H.; Okla, M. K.; Al-Hashimi, A.; Al-Qahtani, W. H.; AbdElgawad, H.; Haq, I.-u.; Anti-inflammatory potential of daturaolone from Datura innoxia Mill.: In silico, in vitro and in vivo studies Pharmaceuticals 14, 1248, (2021) DOI: 10.3390/ph14121248

Exploration of leads with therapeutic potential in inflammatory disorders is worth pursuing. In line with this, the isolated natural compound daturaolone from Datura innoxia Mill. was evaluated for its anti-inflammatory potential using in silico, in vitro and in vivo models. Daturaolone follows Lipinski’s drug-likeliness rule with a score of 0.33. Absorption, distribution, metabolism, excretion and toxicity prediction show strong plasma protein binding; gastrointestinal absorption (Caco-2 cells permeability = 34.6 nm/s); no blood–brain barrier penetration; CYP1A2, CYP2C19 and CYP3A4 metabolism; a major metabolic reaction, being aliphatic hydroxylation; no hERG inhibition; and non-carcinogenicity. Predicted molecular targets were mainly inflammatory mediators. Molecular docking depicted H-bonding interaction with nuclear factor kappa beta subunit (NF-κB), cyclooxygenase-2, 5-lipoxygenase, phospholipase A2, serotonin transporter, dopamine receptor D1 and 5-hydroxy tryptamine. Its cytotoxicity (IC50) value in normal lymphocytes was >20 µg/mL as compared to cancer cells (Huh7.5; 17.32 ± 1.43 µg/mL). Daturaolone significantly inhibited NF-κB and nitric oxide production with IC50 values of 1.2 ± 0.8 and 4.51 ± 0.92 µg/mL, respectively. It significantly reduced inflammatory paw edema (81.73 ± 3.16%), heat-induced pain (89.47 ± 9.01% antinociception) and stress-induced depression (68 ± 9.22 s immobility time in tail suspension test). This work suggests a possible anti-inflammatory role of daturaolone; however, detailed mechanistic studies are still necessary to corroborate and extrapolate the findings.
Publikation

Aslam, M.; Fozia, F.; Gul, A.; Ahmad, I.; Ullah, R.; Bari, A.; Mothana, R. A.; Hussain, H.; Phyto-extract-mediated synthesis of silver nanoparticles using aqueous extract of Sanvitalia procumbens, and characterization, optimization and photocatalytic degradation of Azo Dyes Orange G and Direct Blue-15 Molecules 26, 6144, (2021) DOI: 10.3390/molecules26206144

Green synthesis of silver nanoparticles (AgNPs) employing an aqueous plant extract has emerged as a viable eco-friendly method. The aim of the study was to synthesize AgNPs by using plant extract of Sanvitalia procumbens (creeping zinnia) in which the phytochemicals present in plant extract act as a stabilizing and reducing agent. For the stability of the synthesized AgNPs, different parameters like AgNO3 concentration, volume ratios of AgNO3, temperature, pH, and contact time were studied. Further, AgNPs were characterized by UV–visible spectroscopy, FT-IR (Fourier Transform Infrared Spectroscopy), XRD (X-ray Diffraction), SEM (Scanning Electron Microscopy), and EDX (Energy Dispersive X-ray Spectrometer) analysis. FT-IR analysis showed that the plant extract contained essential functional groups like O–H stretching of carboxylic acid, N–H stretching of secondary amides, and C–N stretching of aromatic amines, and C–O indicates the vibration of alcohol, ester, and carboxylic acid that facilitated in the green synthesis of AgNPs. The crystalline nature of synthesized AgNPs was confirmed by XRD, while the elemental composition of AgNPs was detected by energy dispersive X-ray analysis (EDX). SEM studies showed the mean particle diameter of silver nanoparticles. The synthesized AgNPs were used for photocatalytic degradation of Orange G and Direct blue-15 (OG and DB-15), which were analyzed by UV-visible spectroscopy. Maximum degradation percentage of OG and DB-15 azo dyes was observed, without any significant silver leaching, thereby signifying notable photocatalytic properties of AgNPs.
Publikation

Ali, I.; Mu, Y.; Atif, M.; Hussain, H.; Li, J.; Li, D.; Shabbir, M.; Bankeu, J. J. K.; Cui, L.; Sajjad, S.; Wang, D.; Wang, X.; Separation and anti-inflammatory evaluation of phytochemical constituents from Pleurospermum candollei (Apiaceae) by high-speed countercurrent chromatography with continuous sample load J Sep Sci 44, 2663-2673, (2021) DOI: 10.1002/jssc.202100155

Pleurospermum (Apiaceae) species possess a wide range of biological properties viz. analgesic, anti-inflammatory, antimalarial, and so on. Pleurospermum candollei (DC.) Benth. Ex C. B. Clark. is reported to cure diarrhea, gastric, respiratory, stomach, abdominal, joint, and back pain problems. In addition, it is also used for both male and female infertility. The present study deals with an efficient technique using high-speed countercurrent chromatography for separation of chemical components from the methanol extract of P. candollei. Notably, nine main compounds namely luteolin 7-O-glucoside (1), oxypeucedanin hydrate (2), pabulenol (3), bergapten (4), heptadecanoic acid (5), (E)-isoelemicin (6), trans-asarone (7), α-linolenic acid (8), and isoimperatorin (9) were very efficiently separated and isolated in pure form. Multiple injections were applied followed by two off-line recycling high-speed countercurrent chromatography. The inhibitory effect of nitric oxide production of all compounds was tested in the presence of 200 ng/mL lipopolysaccharide in RAW264.7 mice macrophage cells. The results demonstrated that compounds 7 and 8 effectively inhibited nitric oxide production, with IC50 values of 28.44 and 53.18 μM, respectively. This study thus validates the traditional claim of using P. candollei. Taken together, these findings will be useful in future research to find a potential candidate with anti-inflammatory properties.
Publikation

Ali, I.; Ali, M.; Shareef, H.; Naeem, S.; Khadim, A.; Ali, M.; Amber, F.; Hussain, H.; Ismail, M.; Shah, S. T. A.; Noor, A.; Wang, D.; Phytochemical analysis and biological activities of “Cherchoomoro” (Nepeta adenophyta Hedge) J. Ethnopharmacol. 279, 114402, (2021) DOI: 10.1016/j.jep.2021.114402

Ethnopharmacological relevance: Nepeta adenophyta Hedge (Lamiaceae) is an endemic therapeutic herb from Astore, Gilgit (Pakistan). This plant species has been reported among the local communities, especially for treating abdominal pain, kidney pain, menstrual pain, headache, and controlling bleeding disorders. Therefore, the scientific basis is provided for the relief of pain as it is used in various pain management among the natives, especially as ethnogynecological herbal remedy. Aim of the study: The present study investigates the analgesic and anti-inflammatory effects of the ethanolic extract of N. adenophyta in animal models. Furthermore, the extract was also studied to determine their valuable phytoconstituents. Material and methods: The biological effects were determined via tail-flick, hot plate, and acetic-acid-induced abdominal writhing methods. At the same time, anti-inflammatory activity was assesed via oxidative burst and antioxidant DPPH assay. Gas chromatography-mass spectrometry (GC-MS), and liquid chromatography-mass spectrometry (LC-MS) techniques were employed to understand the phytochemicals present in the crude ethanolic extract of Nepeta adenophyta. Results: In the current study, Nepeta adenophyta extract exhibited potent analgesic and anti-inflammatory effects on different pain models and indicated that the analgesic effect of N. adenophyta extract is mediated both in central and peripheral ways. Dose-dependent and significant (P < 0.05) increases were shown in pain threshold, at 45 min post-treatment, with 20 and 40 mg/kg of the extract in the tail-flick model. The effects of the extract were similar to aspirin but lower to those by morphine (2.5 mg/kg) in the same tests. The extract (20–40 mg/kg) showed dose-dependent inhibition of writhing with a significant (P < 0.001) increase protection against thermal stimuli in hot plate test as compared to control and similar to aspirin and morphine. Further, the anti-inflammatory activity of the crude in oxidative burst and DPPH assays showed significant inhibitory activity. The chemical profile analysis showed major phytochemicals, including long chain derivatives of alkane and alcohol, phenolics, naphthalene, naphthopyran, androsten phenanthrenone, nepetalactones, flavonoids etc. Conclusions: Nepeta adenophyta Hedge is suggested as a natural alternative for mild pain relief. Our findings endorse the folklore use of N. adenophyta in different pain managements which can be attributed to the presence of polyphenolic compounds, naphthalene derivatives, flavanoids and nepetalactones etc.
Publikation

Ali, M.; Hussain, H.; Hussain, A.; Rauf, A.; Hussain, W.; Ullah, M.; Abbas, S.; Al-Awthan, Y. S.; Bahattab, O.; Khan, M.; Olatunde, A.; Almarhoon, Z. M.; Mabkhot, Y. N.; Alshehri, M. M.; Daştan, S. D.; Ramadan, M. F.; Sharifi-Rad, J.; Hepatoprotective screening of Seriphidium kurramense (Qazilb.) Y.R. Ling BioMed Research International 2021, 9026731, (2021) DOI: 10.1155/2021/9026731

Investigation on medicinal plants’ therapeutic potential has gained substantial importance in the discovery of novel effective and safe therapeutic agents. The present study is aimed at investigating the hepatoprotective potential of Seriphidium kurramense methanolic extract (SKM) against carbon tetrachloride- (CCl4-) induced hepatotoxicity in rats. S. kurramense is one of the most imperative plants for its various pharmacological activities. Therefore, this study was aimed at evaluating the hepatoprotective potential against CCl4-induced liver toxicity. The serum samples were analyzed for alanine aminotransferase (ALT) and aspartate aminotransferase (AST) together with the oxidative stress mediator levels as nitric oxide (NO), malondialdehyde (MDA), glutathione (GSH), reduced glutathione (GSH), and superoxide dismutase (SOD) as well as peroxidation and H2O2 activity. CCl4 administration resulted in an elevated free radical generation, altered liver marker (AST and ALT) enzymes, reduced antioxidant enzyme, and increased DNA damage. Methanolic extract of S. kurramense decreased CCl4-induced hepatotoxicity by increasing the antioxidant status and reducing H2O2 and nitrate content generation as well as reducing DNA damage. Additionally, SKM reversed the morphological alterations induced by CCl4 in the SKM-treated groups. These results demonstrated that SKM displayed hepatoprotective activity against CCl4-induced hepatic damage in experimental rats.
Publikation

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.
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