Relevant bibliographies by topics / Biologically active metabolite

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Academic literature on the topic 'Biologically active metabolite'

Author: Grafiati
Published: 4 June 2021
Last updated: 13 February 2022

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Journal articles on the topic "Biologically active metabolite"

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Savchuk, Ya I., K. S. Tsyhanenko, O. V. Andrienko, and I. M. Kurchenko. "The New Biologically Active Metabolites from Aspergillus niveus 2411." Mikrobiolohichnyi Zhurnal 83, no. 4 (August 17, 2021): 74–85. http://dx.doi.org/10.15407/microbiolj83.04.074.

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Pharmacological science possesses a significant number of compounds with antibiotic activity. By now the chemical structures have been identified and their properties have been described for the great number; many of them found practical use. But the main stimulus for the further new antibiotic compounds search is the acquired resistance of pathogenic organisms. Our previous investigations were devoted to antibiotic activity of Aspergillus niveus that is known as a producer of ferment preparations with wide activity spectrum. Aim. This investigation became the follow-up of our previous studies and its main task was to isolate, purify and obtain biologically active metabolite(s) from A. niveus 2411 strain in crystalline form, and to study its (their) physicochemical properties and biological activity. Methods. Biologically active metabolites were obtained by extraction, two-step column chromatography and recrystallization methods. The obtained substances were characterized by physical-chemical and microbiological methods. Results. Two substances in crystalline form with different spectrum of antibiotic activity against indicator test-cultures were obtained. The substance AN4 showed antibacterial, antifungal, and phytotoxic activities, while AN7 showed only antibacterial activity. Neither of obtained compounds showed dermatocidal or toxigenic activity in rabbit skin test. Obtained spectral characteristics of substances suggest that AN4 and AN7 substances are similar and belong to compounds with cyclic structures, have double linkage, methyl, aromatic, and carboxyl groups. Conclusions. Obtained data showed that antibiotic activity of A. niveus 2411 depend on the complex of biologically active metabolites with different biological and physicochemical properties. Two compounds AN4 and AN7 were isolated and purified from the fungal cultural filtrate of A. niveus 2411. The data of IR and UV spectra of these compounds and their profiles of biological activity don’t have significant differences with those of citrinin – a metabolite of A. niveus with antibiotic properties. However, based on the results obtained and comparisons with the data of other authors on metabolites of A. niveus, we suggest that the substances we isolated may be derivatives of citrinin.
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Choudhry, Satish C., Peter S. Belica, David L. Coffen, Antonino Focella, Hubert Maehr, Percy S. Manchand, Lucia Serico, and Roxana T. Yang. "Synthesis of a biologically active vitamin D2 metabolite." Journal of Organic Chemistry 58, no. 6 (March 1993): 1496–500. http://dx.doi.org/10.1021/jo00058a034.

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Krajčová, A., V. Schulzová, J. Lojza, L. Křížová, and J. Hajšlová. "Phytoestrogens in bovine plasma and milk – LC-MS/MS analysis." Czech Journal of Food Sciences 28, No. 4 (September 6, 2010): 264–74. http://dx.doi.org/10.17221/138/2010-cjfs.

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Phytoestrogens belong to a group of polyphenolic plant metabolites which induce biological responses, based on their structural similarity to 17β-estradiol. In order to investigate the relationship between the levels of these biologically active compounds and beneficial health effects, it is neccesary to quantify accurately their levels in foods and biological fluids. In this study, HPLC-MS/MS method for the determination of isoflavones genistein, daidzein, and estrogenic metabolite-equol in bovine plasma and milk was optimised and validated. The method allowed low limits of detection: 5, 2.5 and 0.5 ng/ml for genistein, daidzein and equol, respectively, thus enabling to determine the effect of phytoestrogen-rich diet on the concentration of isoflavones and the metabolite in biological fluids of cows. The feeding experiment, carried out with four dairy cows, showed that a soy-based diet significantly increased both plasma and milk contents of biologically potent equol, therefore, the latter commodity could be an alternative source of this estrogenic metabolite, namely for the consumers who are not capable to convert it from the isoflavone precursors consumed in the diet.
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Sułkowska-Ziaja, Katarzyna, Bożena Muszyńska, and Anna Firlej. "Biologically active compounds from selected aphyllophorales mycelial cultures." Folia Biologica et Oecologica 10 (November 30, 2014): 73–79. http://dx.doi.org/10.2478/fobio-2014-0004.

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For a long time fungi belonging to Basidiomycota phylum have been in the center of attention because of the presence in their fruiting bodies of compounds with known therapeutic activity. Mycelial cultures of two aphyllophorales species occurring in Poland, Hydnum repandum L., and Sparassis crispa (Wulf.) Fr., were analyzed in our study. The main aim of the study was qualitative and quantitative analysis of extracts obtained from the mycelial cultures for the presence of known biologically active compounds, including phenolic acids, non-hallucinogenic indole compounds and sterols. For analyses a reversed-phase chromatography (RP-HPLC) method was used. The presence of eight phenolic acids including gallic, gentisic, p-hydroxybenzoic, caffeic, p-coumaric protocatechuic, syringic, vanillic and cinnamic acids was confirmed in the extracts obtained from the biomass. The quantitatively predominant metabolites in biomass from in vitro cultures of H. repandum and S. crispa were protocatechuic acid (6.23 μg/g DW) and p-hydroxybenzoic acid (4.52 μg/g DW). Derivatives of indole such as indole, serotonin, tryptamine and tryptophan were measured quantitatively. Their total content was estimated as 1.28 μg/g DW and 3.07 μg/g DW in H. repandum and S. crispa extracts, respectively. The major metabolite found was tryptophan. In addition, ergosterol, one of the sterols present in the biomass of in vitro cultures of S. crispa was analyzed (700.87 μg/g DW). The obtained results confirm the hypothesis that mycelial cultures of domestic species of aphyllophorales are able to accumulate biologically active metabolites.
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Cheng, Tian, Clara Chepkirui, Cony Decock, Josphat C. Matasyoh, and Marc Stadler. "Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa." Beilstein Journal of Organic Chemistry 15 (November 19, 2019): 2782–89. http://dx.doi.org/10.3762/bjoc.15.270.

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During the course of screening for new metabolites from basidiomycetes, we isolated and characterized five previously undescribed secondary metabolites, skeletocutins M–Q (1–5), along with the known metabolite tyromycin A (6) from the fruiting bodies of the polypore Skeletocutis sp. The new compounds did not exhibit any antimicrobial, cytotoxic, or nematicidal activities. However, compound 3 moderately inhibited the biofilm formation of Staphylococcus aureus (S. aureus), while compounds 3 and 4 performed moderately in the ʟ-leucine-7-amido-4-methylcoumarin (ʟ-Leu-AMC) inhibition assay. These compounds represent the first secondary metabolites reported to occur in the fruiting bodies by Skeletocutis. Interestingly, tyromycin A (6) was found to be the only common metabolite in fruiting bodies and mycelial cultures of the fungus, and none of the recently reported skeletocutins from the culture of the same strain were detected in the basidiomes.
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Nofiani, Risa. "Urgensi dan Mekanisme Biosintesis Metabolit Sekunder Mikroba Laut." Jurnal Natur Indonesia 10, no. 2 (November 20, 2012): 120. http://dx.doi.org/10.31258/jnat.10.2.120-125.

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Marine microorganism is one of biologically active potential resources of secondary metabolites. Its potency areso promising that the knowledge of how its secondary metabolite occured need to be studied and collected. Thoseknowledges will enable further study is improving secondary metabolite production in the laboratory. In nature,secondary metabolites synthesis occur when there are effect of both biotic and abiotic factors such as sea waterand microbe symbiosis with other living materials. When this is explained in metabolic pathways, secondarymetabolite synthesis affected by available nutrient and regulated by autoinducer molecules through quorum sensingmechanism
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Okeke, Boniface, Mourad Kaouadji, Françoise Seigle-Murandi, and Régine Steiman. "Setosol, a Biologically Active Heptaketide-like Metabolite from thePleiochaeta setosaPhytopathogen." Bioscience, Biotechnology, and Biochemistry 58, no. 4 (January 1994): 734–36. http://dx.doi.org/10.1271/bbb.58.734.

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Nishizawa, Rena, Toshihiko Nishiyama, Katsuya Hisaichi, Naoki Matsunaga, Chiaki Minamoto, Hiromu Habashita, Yoshikazu Takaoka, et al. "Spirodiketopiperazine-based CCR5 antagonists: Lead optimization from biologically active metabolite." Bioorganic & Medicinal Chemistry Letters 17, no. 3 (February 2007): 727–31. http://dx.doi.org/10.1016/j.bmcl.2006.10.084.

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Higgs, Richard E., James A. Zahn, Jeffrey D. Gygi, and Matthew D. Hilton. "Rapid Method To Estimate the Presence of Secondary Metabolites in Microbial Extracts." Applied and Environmental Microbiology 67, no. 1 (January 1, 2001): 371–76. http://dx.doi.org/10.1128/aem.67.1.371-376.2001.

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ABSTRACT Screening microbial secondary metabolites is an established method to identify novel biologically active molecules. Preparation of biological screening samples from microbial fermentation extracts requires growth conditions that promote synthesis of secondary metabolites and extraction procedures that capture the secondary metabolites produced. High-performance liquid chromatography (HPLC) analysis of fermentation extracts can be used to estimate the number of secondary metabolites produced by microorganisms under various growth conditions but is slow. In this study we report on a rapid (approximately 1 min per assay) surrogate measure of secondary metabolite production based on a metabolite productivity index computed from the electrospray mass spectra of samples injected directly into a spectrometer. This surrogate measure of productivity was shown to correlate with an HPLC measure of productivity with a coefficient of 0.78 for a test set of extracts from 43 actinomycetes. This rapid measure of secondary metabolite productivity may be used to identify improved cultivation and extraction conditions by analyzing and ranking large sets of extracts. The same methods may also be used to survey large collections of extracts to identify subsets of highly productive organisms for biological screening or additional study.
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Ghoneim, Mohammed M., Guoyi Ma, Atef A. El-Hela, Abd-Elsalam I. Mohammad, Saeid Kottob, Sayed El-Ghaly, Stephen J. Cutler, and Samir A. Ross. "Biologically Active Secondary Metabolites from Asphodelus Microcarpus." Natural Product Communications 8, no. 8 (August 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800822.

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Bioassay guided fractionation of the ethanolic extract of Asphodelus microcarpus Salzm.et Vivi (Asphodelaceae) resulted in the isolation of one new metabolite, 1,6-dimethoxy-3-methyl-2-naphthoic acid (1) as well as nine known compounds: asphodelin (2), chrysophanol (3), 8-methoxychrysophanol (4), emodin (5), 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (6), 10-(chrysophanol-7’-yl)-10-hydroxychrysophanol-9-anthrone (7), aloesaponol-III-8-methyl ether (8), ramosin (9) and aestivin (10). The compounds were identified by 1D and 2D NMR and HRESIMS. Compounds 3, 6 and 10 were isolated for the first time from this species. Compounds 3 and 4 showed moderate to weak antileishmanial activity with IC50 values of 14.3 and 35.1 μg/mL, respectively. Compound 4 exhibited moderate antifungal activity against Cryptococcus neoformans with an IC50 value of 15.0 μg/mL, while compounds 5, 7 and 10 showed good to potent activity against methicillin resistant Staphylococcus aureus (MRSA) with IC50 values of 6.6, 9.4 μg/mL and 1.4 μg/mL respectively. Compounds 5, 8 and 9 displayed good activity against S. aureus with IC50 values of 3.2, 7.3 and 8.5 μg/mL, respectively. Compounds 7 and 9 exhibited a potent cytotoxic activity against leukemia LH60 and K562 cell lines. Compound 10 showed potent antimalarial activities against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum with IC50 values in the range of 0.8-0.7 μg/mL without showing any cytotoxicity to mammalian cells.
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Dissertations / Theses on the topic "Biologically active metabolite"

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Stacey, N. A. "An approach to avermectin and milbemycin synthesis." Thesis, University of Oxford, 1987. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.379897.

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Dewi, Ariyanti Suhita. "Biologically active secondary metabolites from tropical marine invertebrates." Thesis, University of British Columbia, 2009. http://hdl.handle.net/2429/15299.

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In our effort to discover promising anticancer agents, we have screened a series of compounds for their activities as indoleamine-2,3-dioxygenase (IDO) inhibitor and SHcontaining inositol 5-phosphatase (SHIP1) activator. In comparison to aaptamine (2.1) and demethylaaptamine (2.2), isoaaptamine (2.4) from Aaptos cf. suberitoides appears to be the most promising IDO inhibitor with an IC₅₀ of 0.00215 mg/mL, owing to the presence of hydroxyl group at C9 position and the methylation at N1 position. A study on the sponge extract of RJA 55275 for its SHIP activator yielded theonellapeptolide Id (3.4), the first peptide that enhanced the SHIP with 25% activity at concentration 124 μM, thus makes it the most potent SHIP activator known to date. The third project studied the crystals of a novel eunicellin-based diterpenoid (4.39) with a modest SHIP activity from an unidentified Micronesian soft coral RJA 47686. The X-ray analysis illustrated that the crystals are monoclinic, space group P21/b, with a = 9.3711(14) A; α = 90⁰; b = 13.5349(17) A; β = 99.142(7)⁰; c = 10.9891(17) A; γ = 90⁰; V = 1376.1 (3) ų; Z value = 2; Dcalc 1.189. 10-³ g/cm³; F₀₀₀ 536.00; Cu (MoKα) 0.84 cm-¹. Based on the NMR and x–ray data 4.39 was shown to possess (1R*, 2R*, 3R*, 6R*, 7S*, 10R*, 14R*, 18R*)-configuration with an ether linkage connecting C2 and C6.
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Chapman, Robert Laurence. "Biologically active secondary metabolites of the fungus, Aspergillus flavipes /." The Ohio State University, 1993. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487843314694226.

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Vinayavekhin, Nawaporn. "Metabolomics Strategies for Discovery of Biologically Active or Novel Metabolites." Thesis, Harvard University, 2012. http://dissertations.umi.com/gsas.harvard:10150.

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Along with genes and proteins, metabolites play important roles in sustaining life. There remains much to be learned about the in vivo roles of metabolites. Metabolomics is a comparative tool to study global metabolite levels in samples under various conditions. This dissertation describes the development and application of metabolomics strategies for discovery of biologically active or novel metabolites with priori knowledge about genes, proteins, or phenotypes. The power of metabolomics for discovery of novel metabolites from genes is demonstrated through the work with the pyochelin (pch) gene cluster. Comparison of the extracellular metabolomes of pch gene cluster mutants to the wild-type Pseudomonas aeruginosa (strain PA14) identified 198 ions regulated by the pch genes. In addition to known metabolites, a pair of novel metabolites were characterized as 2-alkyl-4,5-dihydrothiazole-4-carboxylates (ATCs). Subsequent assays revealed that ATCs bind iron and that their production is regulated by iron levels and dependent on pchE gene in the pch gene cluster. Metabolomics can also facilitate discovery of active metabolites from proteins, as shown in the work with orphan nuclear receptor Nur77. We applied a metabolomics platform for detected protein-metabolite interactions to identify lipids that bind to Nur77. Using this approach, we discovered that the Nur77 ligand-binding domain (Nur77LBD) enriched unsaturated fatty acids (UFAs) in tissue lipid mixtures. Subsequent biophysical and biochemical assays indicate that UFAs bind to Nur77LBD to cause changes in the conformation and oligomerization of the receptor. Last, analogous to classic fractionation experiments, metabolomics can also be applied to discover active metabolites from phenotypes. Using combination of genetics, biochemistry, and metabolomics, we identified three phenazine compounds produced by Pseudomonas aeruginosa that are toxic to the nematode Caenorhabditis elegans. 1-hydroxyphenazine, phenazine-1-carboxylic acid (PCA), and pyocyanin are capable of killing nematodes in a matter of hours. 1-hydroxyphenazine is toxic over a wide pH range, whereas the toxicities of PCA and pyocyanin are strictly pH-dependent at non-overlapping pH ranges. The diversity within a class of metabolites can be used to modulate bacterial toxicity in different environmental niches.
Chemistry and Chemical Biology
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Kottakota, Suresh Kumar. "The synthesis of novel biologically active marine sponge secondary metabolites." Thesis, University of Sunderland, 2014. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.592881.

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Bromotyrosine-derived secondary metabolites from marine sponges of the order Verongida provide unique diversity in chemical structure and a wide range of biological activities. With a decline in the number of novel antibiotic scaffolds which are emerging and the on-going search for more effective antibacterial and anticancer drugs, these brominated metabolites are attractive candidates for further total synthesis and biological evaluation. An Efficient total synthesis of bromotyrosine alkaloids purpurealdin E (92), aplyzanzine A (122), suberedamine A (123) and B (124), iso-Anomoian A (121a) and aplysamine-2 (104) were achieved through the carbodiimide coupling of appropriate tyrosine/tyramine units in excellent yields. Their structures have been confirmed through direct comparison with spectroscopic data of isolated natural products. The key step was the one-pot Bocdeprotection, dimethylation and hydrolysis of desired intermediate, which was achieved in 88% yield. A new synthetic route was developed for the preparation of diverse analogues for biological assessment. This route utilized cheap and commercially available starting materials, and allowed access to various analogues inaccessible via currently reported methods. By utilising this route, the total syntheses of 5- bromoverongamine (207), 20-N-methylpu rpuramine E (208) , psammaplin A (150), psammaplin C (156), spermatinamine (50) and tokaradine A (209) were successfully carried out and are reported herein. These new syntheses of spermatinamine and psammaplin A are more efficient than previously reported sequences. In addition, we explored a method for the selective removal of benzyl protecting groups in the presence of both oxime and disulphide moieties. Aplyzanzine A (122) was found to be the most active product against a Grampositive bacterial and fungal screen demonstrating MIC values 2-4 times lower than the other compounds. All compounds, except purpurealdin E and psammaplin C, exhibit modest inhibition against M. bovis BCG and M. tuberculosis H37Rv. 20-N-methylpurpuramine-E (208) was most active with an MIC (5 μg/mL) towards M. bovis BCG. iso-Anomoian A (1 21a) and suberedamine B (124) showed antitumor activity in the NCI-DTP60 cell line screen at single micromolar concentrations, with iso-anomoian A (121 a) inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.
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Alenazi, Mohrah. "Extraction and Purification of Biologically Active Metabolites from Rhodococcus sp. MTM3W5.2." Digital Commons @ East Tennessee State University, 2018. https://dc.etsu.edu/etd/3507.

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Rhodococcushas been recognized as a potential antibiotic producer. Recently, a strain of Rhodococcussp. MTM3W5.2 was isolated from a soil sample collected in Morristown, Tennessee and was found to produce an inhibitory compound which is active against other related species. The purpose of this research is to extract, purify and analyze the active metabolite. The compound was extracted from RM broth cultures and purified by preliminary fractionation of crude extract through a Sephadex LH-20 column. Further purification was completed using semi-preparative reversed phase column chromatography. Final purification was obtained using multiple rounds of an analytical C18 HPLC column. Based on the results achieved in the UV-Vis spectroscopy and high-resolution mass spectroscopy, the two desired compounds at a retention time of at 57 and 72 min could be polyketides with the molecular formulas C52H78O13 and C19H32O1N1/C13H34O1N1, respectively.
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Dajana, Kovač. "Biotehnološki potencijal filamentoznih sojeva cijanobakterija sa područja Vojvodine." Phd thesis, Univerzitet u Novom Sadu, Prirodno-matematički fakultet u Novom Sadu, 2017. https://www.cris.uns.ac.rs/record.jsf?recordId=104930&source=NDLTD&language=en.

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S obzirom  da su cijanobakterije (modrozelene alge) identifikovane kao jedna odnajperspektivnijih grupa organizama za izolaciju novih i biološki aktivnih prirodnihprodukata, cilj ove teze bio  je utvrđivanje biotehnološkog potencijala  autohtonihfilamentoznih sojeva  cijanobakterija izolovanih sa područja Vojvodine koji pripadajuazotofiksirajućim rodovima  Nostoc  i  Anabaena  i neazotofiksirajućem rodu    Spirulina. Biotehnološki potencijal testiranih sojeva je određen  u smislu produkcije biomase, fikobiliproteinskih pigmenata, masnih kiselina, fenolnih jedinjenja, antioksidanata, antibakterijskih i antikancerogenih agenasa. Dobijeni rezultati su pokazali  da su produkcija biomase i sadržaj fikobiliproteinskih pigmenata kod svih testiranih sojeva zavisili od primenjenih uslova kultivacije, pri  čemu je  kod sojeva roda  Spirulina produkcija biomase bila jače stimulisana primenom kontinualnog osvetljenja, a kod azotofiksirajućih sojeva rodova  Nostoc  i  Anabaena  organskim izvorima ugljenika (glicerolom i glukozom). Kao soj sa najvećim potencijalom za  proizvodnju biomase izdvaja se soj  Spirulina  S1, a za produkciju fikobiliproteina sojevi  Spirulina  S1,  Nostoc 2S1,  Anabaena  Č2 i  Spirulina  S2.  Određivanjem sadržaja masnih kiselina GC-FID metodom utvrđeno je da su  kod svih sojeva  najzastupljenije bile palmitinska, palmitoleinska, oleinska i linolna kiselina, pri čemu su  sojevi roda Spirulina produkovali i  γ-linolensku kiselinu, dok su svi  sojevi rodova  Nostoc  i  Anabaena  produkovali  -linoleinsku kiselinu.  Najzastupljenije fenolne komponente testiranih etanolnih ekstrakata određene HPLC-MS/MS metodom  bile su hinska kiselina i katehin, pri čemu je najveći sadržaj fenolnih jedinjenja registrovan kod soja  Nostoc  2S7B. Hemijskom karakterizacijom ekstrakata kod testiranih sojeva takođe je utvrđen značaj azotnih uslova kultivacije  u cilju povećanja produkcije  fenolnih jedinjenja,  kao i  -linoleinske kiseline. Poređenjem rezultata antioksidantne aktivnosti u korišćenim testovima  DPPH  i FRAP, kao sojevi sa najvećim  antioksidantnim potencijalom izdvajaju se  Spirulina  S1 i Spirulina  S2. Antibakterijska aktivnost metanolnih ekstrakata  registrovana je kod sojeva Nostoc 2S7B, Nostoc 2S1, Anabaena Č2, Anabaena Č5, Spirulina S1 i  Spirulina S2, koji su ispoljili efekat na Gram-pozitivne i Gram-negativne bakterije, pri čemu su  sojevi Anabaena  Č2, Nostoc  2S7B  i  Nostoc  2S1  delovali na najviše bakterijskih sojeva.  Kod svih testiranih sojeva je primenom MTT testa uočena antikancerogena tj. citotoksična aktivnost dimetil sulfoksidnih (DMSO) ekstrakata prema HepG2 ćelijskoj liniji, među kojima su najveću aktivnost  ispoljili sojevi  Nostoc  LC1B i  Nostoc  2S7B.  Primenom bioeseja  Artemia salina, Daphnia magna  i   Danio rerio  konstatovan je mali broj sojeva koji su ispoljili toksičnost na test organizme, dok na ćelijsku liniju  RTL-W1  testirani sojevi nisu ispoljili citotoksičnost  in vitro, što sa aspekta potencijalne biotehnološke primene sojeva ima veliki značaj. Kao najtoksičniji izdvojili su se sojevi  Nostoc  LC1B  i Nostoc S8 koji su ispoljili  toksičnost u sva tri bioeseja. Ispitivanjem toksičnosti in vitro u enzimskim esejima konstatovano je da je manji broj sojeva inhibirao aktivnost enzimaprotein fosfataze 1 (PP1) u odnosu na aktivnost enzima  acetilholinesteraze  (AChE). Primenom Analitičkog hijerarhijskog procesa u grupnom kontekstu, najveću težinu su dobili kriterijumi antikancerogena ativnost, produkcija biomase i sadržaj fikocijanina, navedenim redom. Konačno, u višekriterijumskom kontekstu najbolje rangiran soj jeSpirulina S1, na drugom mestu je soj Spirulina S2, dok je na trećem soj  Nostoc  LC1B.
Cyanobacteria (blue-green algae) have been identified as one  of the most promising groups of organisms for the isolation of new and biologically active natural products, therefore, the aim of this thesis was to determine the biotechnological potential of autochthonous filamentous cyanobacterial strains isolated from  Vojvodina region,  which belong to the N 2-fixing genera  Nostoc  and  Anabaena  and non-N2-fixing genus  Spirulina. Biotechnological potential of tested strains was determined using the production of biomass, phycobiliprotein pigments, fatty acids, phenolic co mpounds, antioxidants, antibacterial and anticancer agents. The obtained results showed that the production of biomass and phycobiliprotein pigments, in all tested strains, depended on the cultivationconditions, whereas biomass production was strongly stimulated by continuous light in Spirulina  strains, and by organic carbon sources (glycerol and glucose) in N2-fixingstrains. The highest potential for biomass production was shown in  Spirulina  S1 strain.On the other hand, the highest potential  for the production of phycobiliproteins wasshown in strains  Spirulina  S1,  Nostoc  2S1,  Anabaena C2 and  Spirulina  S2. By determination of the content of fatty acids using GC-FID method it was found that in allthe tested strains the most common fatty acids were palmit ic, palmitoleic, oleic andlinoleic acid, whereby the strains of the genus  Spirulina produced γ-linolenic acid as well,while all strains of the Nostoc  and Anabaena  genera produced y-linolenic acid. The most frequent phenolic compounds of tested strains determined by using the HPLC-MS/MSmethod were quinic acid and catechin, with the highest content of phenolic compounds registered in Nostoc  strain 2S7B. By chemical characterization of the extracts in the tested strains it was also stated a significance of  the nitrogen cultivation conditions in order toincrease the production of phenolic compounds, as well as  y-linolenic acid. Comparing the results of the antioxidant activity in the DPPH and FRAP tests, it  was shown that strains  Spirulina  S1 and  Spirulina  S2 had the highest antioxidant potential. The antibacterial activity of the intracellular methanolic extracts was registered in strains Nostoc  2S7B,  Nostoc  2S1,  Anabaena  C2,  Anabaena  C5,  Spirulina  S1 and  Spirulina  S2, that  inhibited the growth of  Gram-positive and Gram  -negative bacteria. Using MTT test, anti-cancer ie. cytotoxic activity of  dimethyl sulfoxide  (DMSO) extracts to the HepG2 cell line was detected in all tested strains, however, the highest activity was exhibited in strains Nostoc  LC1B and Nostoc 2S7B . In bioassays Artemia salina,  Daphnia magna  and Danio rerio  a small number of strains exhibited toxicity to the test organisms, while in case of cell line RTL-W1 tested strains did not show  in vitro  cytotoxicity, which is of great importance from the aspect of the potential biotechnological application of thestrains.  Nostoc  LC1B and  Nostoc  S8 strains induced toxicity in all three bioassays, and therefore considered as the most toxic strains. By testing  in vitro  toxicity in enzyme assays, it was found that few strains inhibited the activity of  protein phosphatase (PP1) enzyme in relation to  acetylcholinesterase  enzyme  (AChE) activity. Using the Analytical hierarchical process in the group context, the highest weight was given to the criteria of anticancer  activity, biomass production, and the phycocyanin content, respectively. Finally, in the multi-criteria context, the best-ranked strain is  Spirulina  S1,  Spirulina  strain S2 is on the second place, while Nostoc strain LC1B is the third one.
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Alenazi, Mohrah, Jaimin kapadia, Patrick South, Abbas Shilabin, and Bert Lampson. "Extraction and purification of biologically active metabolites from the Rhodococcus sp. MTM3W5.2." Digital Commons @ East Tennessee State University, 2018. https://dc.etsu.edu/asrf/2018/schedule/71.

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Due to an increasing prevalence of bacterial resistance to antibiotic drugs and the overuse of commercial antibiotics, the need to discover novel antibacterial compounds is becoming more urgent. There is one promising avenue of novel drug discovery which has begun to be explored; the analysis of secondary metabolites. Rhodococcus is a genus of gram-positive bacterium known for their ability to catabolize a wide range of compounds, and more notably for its ability to produce bioactive secondary metabolites. Rhodococcus belongs to the class actinobacteria. A species of Rhodococcus, MTM3W5.2, has been discovered in Morristown, Tennessee and was found to produce a metabolite with inhibitory activity against closely related species. The aim of this study is to elucidate the structure of the inhibitory metabolite by first isolating and purifying it, and then characterizing it using spectroscopic techniques. The compound was isolated from MTM3W5.2 RM broth cultures using n-butanol extraction, which yielded an active crude extract. The crude extract was then subjected to fractionation using a Sephedex LH-20 column with a 100% methanol solvent. The inhibitory activity of the fractions was tested through disk diffusion assay using Rhodococcus erythropolis as an indicator of inhibitory activity. Further preparation was completed using preparative reverse-phase high-performance liquid chromatography. Advanced purification was conducted using multiple rounds of analytical reverse-phase HPLC and activity was tested at each subsequent step using disk diffusion assay. Throughout the study, the HPLC fractions were characterized and the stability was monitored using UV-Visible spectroscopy. Two pure samples at 58.63 and 72.72 minutes from HPLC (High-performance liquid chromatography) collections were selected for further structural identification and are currently being studied using spectroscopic techniques, most notably 2D NMR spectroscopy (two-dimensional nuclear magnetic resonance).
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Hooper, Gregory John. "Biologically active natural products from South African marine invertebrates." Thesis, Rhodes University, 1997. http://hdl.handle.net/10962/d1003239.

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This thesis describes the chemical and biological investigation of the extracts of six different marine invertebrate organisms collected along the South African coastline. The work on these extracts has resulted in the isolation and structural elucidation of twenty-one previously undescribed secondary metabolites; The history of marine natural product chemistry in South Africa has not previously been reviewed and so a comprehensive review covering the literature from the 1940's up until the end of 1995 is presented here. The marine ascidian Pseudodistoma species collected in the Tsitsikamma Marine Reserve was shown to contain four new unsaturated amino alcohols [47], [48], [49] and [50] which were isolated as their acetyl derivatives. These compounds exhibited strong antimicrobial activity. Four new pyrroloiminoquinone alkaloids, the tsitsikammamines A [90] to D [93],were isolated from a new genus of Latrunculid sponge collected in the Tsitsikamma Marine Reserve. These highly pigmented compounds also possessed strong antimicrobial activity. An investigation of two phenotypic colour variants of the soft coral Capnella thyrsoidea resulted in the isolation of the known steroid 5α-pregna-1, 20-dien-3-one [97] and an additional six new metabolites, 16β-hydroxy-5α-pregna-1 ,20-dien-3-one 16-acetate [98], 3α,16β-dihydroxy-5α-pregna-1, 20-diene 3,16-diacetate [99] and four xenicane diterpenes, the tsitsixenicins A [100] to D [103]. This is the first reported isolation of xenicane diterpenes from the soft coral family Nephtheiidae. Tsitsixenicin A and B showed good anti-inflammatory activity by inhibiting superoxide production in both rabbit and human cell neutrophils. A further four new metabolites were isolated from two soft corals which could only be identified to the genus level and were designated Alcyonium species A and species B. Alcyonium species A was collected in the Tsitsikamma Marine Reserve and yielded two new polyhydroxysterols, cholest-5-ene-3β, 7β, 19-triol 19-acetate [121] and cholest-5,24-diene-3β, 7β, 19-triol 19-acetate [122]. The soft coral Alcyonium species B was collected off Aliwal Shoal and was found to contain two known xenicane diterpenes, 9-deacetoxy-14, 15-deepoxyxeniculin [110] and zahavin A [16], and two new xenicane diterpenes, 7 -epoxyzahavin A [123] and xeniolide C [124]. Compounds [110], [16] and [123] exhibited strong anti-inflammatory activity and compounds [110] and [16] showed good antithrombotic activity. The endemic soft coral A/cyanium fauri collected at Riet Point near Port Alfred yielded the new sesquiterpene hydroquinone rietone [141] in high yierd, fogether with the minor compounds 8'-acetoxyrietone [142] and 8'-desoxyrietone [143]. Rietone exhibited moderate activity in the NCl's in-vitro anti-HIV bioassays.
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Sunkel, Vanessa Ann. "The investigation of novel marine microorganisms for the production of biologically active metabolites." Thesis, Rhodes University, 2009. http://hdl.handle.net/10962/d1004579.

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New drugs, particularly antibiotics, are urgently required to combat the increasing problem of antibiotic resistant human pathogens. Due to the scarcity of products available today, the pharmaceutical industry is now under pressure to reassess compounds derived from plants, soil and marine organisms. Pharmaceutical companies are showing renewed interest in marine biotechnology as the oceans represent a rich source of both biological and chemical diversity of novel molecular structures with anti-cancer, anti-inflammatory and antibiotic properties. Formerly unexplored locations, such as deep ocean sediments, show great potential as a source of genetically novel microorganisms producing structurally unique secondary metabolites. In this research, a metabolite producing marine Pseudoalteromonas strain, known as AP5, was initially used to develop methods for the detection, optimisation of production and extraction of bioactive metabolites from other potentially novel marine isolates. Two hundred and seventy six (276) marine isolates from water and sediment samples from the Antarctic Ocean and Marion Island were isolated. Ten visually different isolates were screened for bioactivity against Gram-positive and -negative bacteria, fungi and yeast. Three out of the 10 isolates, WL61 , WL 114 and WL 136, appeared to be novel Streptomyces spp. showing activity against different test organisms. Many of these marine microorganisms are difficult to culture in the laboratory, particularly when they are cultivated continuously in shake flasks as they can stop producing bioactive compounds. The cultivation of marine isolates in bioreactors may be a more beneficial process for the optimisation of metabolite production compared to conventional liquid fermentation techniques whereby the solid-liquid-air interface of membrane bioreactors can imitate the natural environment of microbes. The membrane bioreactor system is a stable growth environment with low shear that supports steady-state biofilm growth consisting of a high cell density due to a high mass transfer of nutrients and oxygen to the cells. This approach was employed and isolates WL61, WL114 and WL136 were immobilised onto ceramic membranes using Quorus single fibre bioreactors (SFR). The SFRs were used to establish the most suitable growth medium for continuous secondary metabolite production. The best growth conditions were applied to the Quorus multifibre bioreactor (MFR) for scale up of biologically active metabolites, highlighting the potential of bioreactor technology for use in bioprospecting for isolating and screening novel and known organisms for new and interesting natural products. Furthermore, the Quorus MFR was shown to be suitable for the production of high yields of antimicrobial metabolites and is an efficient new fermentation production system. Purification by HPLC fractionation was used to characterise four major compounds from isolate WL 114 extracts. NMR structure elucidation identified one of the two primary compounds as Bisphenol A. The complete chemical structure for the second potent bioactive compound could not be determined due to the low concentration and volume of material.
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Books on the topic "Biologically active metabolite"

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Hiroyasu, Aizawa, ed. Metabolic maps: Pesticides, environmentally relevant molecules, and biologically active molecules. San Diego, Calif: Academic Press, 2001.

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Sarma, Aluru S. Secondary metabolites from marine sponges. Berlin: Ullstein Mosby, 1993.

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Felix, Bronner, and Peterlik Meinrad, eds. Cellular calcium and phosphate transport in health and disease: Proceedings of the Third International Workshop on Calcium and Phosphate Transport Across Biomembranes, held in Vienna, Austria, March 1-4, 1987. New York: Liss, 1988.

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NATO Advanced Research Workshop on Molecular and Cellular Mechanisms of H [plus] transport (1993 York, England). Molecular and cellular mechanisms of H [plus] transport. Berlin: Springer-Verlag, 1994.

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International, Symposium on Molecular Basis of Biomembrane Transport (1988 Bari Italy). Molecular basis of biomembrane transport: Proceedings of the International Symposium on Molecular Basis of Biomembrane Transport, Bari, Italy, 30 May-2 June 1988. Amsterdam: Elsevier, 1988.

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International, Symposium on Biological Reactive Intermediates (3rd 1985 University of Maryland College Park). Biological reactive intermediates III: Mechanisms of action in animal models and human disease. New York: Plenum Press, 1986.

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International Symposium on Structure, Function, and Biogenesis of Energy Transfer Systems (1989 Bari, Italy). Structure, function, and biogenesis of energy transfer systems: Proceedings of the International Symposium on Structure, Function, and Biogenesis of Energy Transfer Systems, Bari, Italy, 9-11 July 1989. Edited by Quagliariello E. Amsterdam: Elsevier Science, 1990.

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J, Garrahan Patricio, ed. The Ca2+ pump of plasma membranes. Boca Raton, Fla: CRC Press, 1986.

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Giulio, Milazzo, and Blank Martin 1933-, eds. Bioelecrochemistry III: Charge separation across biomembranes. New York: Plenum Press, 1990.

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International Symposium on 25 Years of Research on the Brush Border Membrane and Sodium-Coupled Transport (1985 Aussois, France). Ion gradient-coupled transport: Proceedings of the International Symposium on 25 Years of Research on the Brush Border Membrane and Sodium-Coupled Transport held in Aussois (France), 18-20 September 1985. Edited by Alvarado Francisco, Os Carel H. van, Institut national de la santé et de la recherche médicale (France)., and Centre national de la recherche scientifique (France). Amsterdam: Elsevier Science Publishers, 1986.

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Book chapters on the topic "Biologically active metabolite"

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Wong, Patrick Y. K. "Transformation of Prostacyclin (PGI2) to a Biologically Active Metabolite: 5(6)-Oxido-PGI1 by Cytochrome P450-Dependent Epdxygenase." In Advances in Experimental Medicine and Biology, 245–50. Boston, MA: Springer US, 1990. http://dx.doi.org/10.1007/978-1-4615-3806-6_24.

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Vater, J. "Lipopeptides, an Interesting Class of Microbial Secondary Metabolites." In Biologically Active Molecules, 27–38. Berlin, Heidelberg: Springer Berlin Heidelberg, 1989. http://dx.doi.org/10.1007/978-3-642-74582-9_3.

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Bills, Gerald F., and James B. Gloer. "Biologically Active Secondary Metabolites from the Fungi." In The Fungal Kingdom, 1087–119. Washington, DC, USA: ASM Press, 2017. http://dx.doi.org/10.1128/9781555819583.ch54.

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Kupfer, David. "Prostanoid Metabolism and Biologically Active Product Formation." In Molecular Aspects of Monooxygenases and Bioactivation of Toxic Compounds, 293–304. Boston, MA: Springer US, 1991. http://dx.doi.org/10.1007/978-1-4684-7284-4_17.

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Shanmugam, A., and S. Vairamani. "Biologically Active Metabolites from Sponges and Their Activities." In Marine Sponges: Chemicobiological and Biomedical Applications, 115–42. New Delhi: Springer India, 2016. http://dx.doi.org/10.1007/978-81-322-2794-6_9.

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Saxena, Sanjai. "Biologically Active Secondary Metabolites from Endophytic Alternaria Species." In Endophytes, 1–20. Singapore: Springer Singapore, 2021. http://dx.doi.org/10.1007/978-981-15-9371-0_1.

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Nagle, Dale G., and Inderjit. "The chemistry and chemical ecology of biologically active cyanobacterial metabolites." In Chemical Ecology of Plants: Allelopathy in Aquatic and Terrestrial Ecosystems, 33–56. Basel: Birkhäuser Basel, 2002. http://dx.doi.org/10.1007/978-3-0348-8109-8_3.

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Ratnaweera, Pamoda B., and E. Dilip de Silva. "Endophytic Fungi: A Remarkable Source of Biologically Active Secondary Metabolites." In Endophytes: Crop Productivity and Protection, 191–212. Cham: Springer International Publishing, 2017. http://dx.doi.org/10.1007/978-3-319-66544-3_9.

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Ferreira, Sergio H., Lewis J. Greene, Maria Cristina O. Salgado, and E. M. Krieger. "The Fate of Circulating Biologically Active Peptides in the Lungs." In Ciba Foundation Symposium 78 - Metabolic Activities of the Lung, 129–45. Chichester, UK: John Wiley & Sons, Ltd., 2008. http://dx.doi.org/10.1002/9780470720615.ch7.

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Skrzypczak, L., M. Wesołowska, B. Thiem, and J. Budzianowski. "Solidago L. Species (Goldenrod): In Vitro Regeneration and Biologically Active Secondary Metabolites." In Medicinal and Aromatic Plants XI, 384–403. Berlin, Heidelberg: Springer Berlin Heidelberg, 1999. http://dx.doi.org/10.1007/978-3-662-08614-8_23.

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Conference papers on the topic "Biologically active metabolite"

1

Mointire, V. L., A. J. Frangos, G. B. Rhee, G. S. Eskin, and R. E. Hall. "RHEOLOGY AND CELL ACTIVATION." In XIth International Congress on Thrombosis and Haemostasis. Schattauer GmbH, 1987. http://dx.doi.org/10.1055/s-0038-1643988.

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The subject of this work is to examine the hypothesis that some sublytic levels of mechanical perturbation of cells can stimulate cell metabolism. As a marker metabolite, we have chosen arachidonic acid. Principal metabolites for platelets include the cyclooxygenase product thromboxane A2(TXA2) and the lipoxygenase product 12-hydroperoxy-eicosatetraenoic acid (12-HPETE). Polymorphonuclear leukocytes (PMNLs) initally produce principally 5-HPETE, somtimes leading to the formation leukotrienes, though many other metabolites of arachidonic acid have been isolated from activated neutrophils. Human umbilical vein endothelial cells utilize arachidonic acid to produce mainly prostaglandin I2(PGI2). All of these metabolites are biologically active and modulate cell function - sometimes in quite contrasting ways. We will show that levels of sublytic mechanical stress exposure can stimulate arachidonic acid metabolism in all three of the cell types mentioned above. The biological implications of this stress/metabolism coupling may be quite far reaching.Human platelets, leukocytes and endothelial cells all appear to be sensitive to mechanical stress induced activation of arachidonic acid metabolism. Sheared PRP exhibited greatly increased synthesis of 12-HETE and surprisingly little thromboxane B2 production. This indicates that shear stress stimulation of platelets may produce quite different arachidonic acid metabolism than that seen with many direct chemical stimuli, such as thrombin or collagen.Our data demonstrate that a substance derived from shear induced platelet activation may activate the C-5 lipoxygenase of human PMNL under stress, leading to the production of LTB4. We hypothesize that this substance maybe 12-HPETE. LTB4 is known to be a very potent chemotactic factor and to induce PMNL aggregation and degranulation. Our studies provide further evidence that lipoxygenase products of one cell type can modulate production of lipoxygenase products in a second cell type, and that shear stress can initiate cell activation. This kind of coupling could have far reaching implications in terms of our understanding of cell/cell interaction in flowing systems, such as acute inflammation, artificial organ implantation and tumor metastasis.The data on PGI2 production by endothelial cells demonstrate that physiological levels of shear stress can dramatically increase arachidonic acid metabolism. Step increases in shear stress lead to a burst in production of PGI2 which decayed to a steady state value in several minutes. This longer term stimulation of prostacyclin production rate increased linearly with shear stress over the range of 0-24 dynes/cm2. In addition, pulsatile flow of physiological frequency and amplitude caused approximately 2.4 times the PGI2 production rate as steady flow with the same mean stress. Although only PGI2 was measured, it is likely that other arachidonic acid metabolites of endothelial cells are also affected by shear stress.The ability of cells to respond to external stimuli involves the transduction of a signal across the plasma membrane. One such external stimulus appears to be fluid shear stress. Steady shear flow induces cell rotation in suspended cells, leading to a periodic membrane loading, with the peak stress proportional to the bulk shear stress. On anchorage-dependent cells, such as endothelial cells, steady shear stress may act by amplifying the natural thermal or Brownian fluttering or rippling of the membrane. There are several possible mechanisms by which shear stress induced membrane perturbation could mimic a hormone/receptor interaction, leading to increased intracellular metabolism. Shear stress may induce increased phospholipase C activity, caused by translocation of the enzyme, increased substrate (arachidonic acid) pool availability to phospholipase C (particularly from that stored in phosphoinositols) due to shear-induced membrane movements or changes in membrane fluidity, direct activation of calcium - activated phospholipase A2 by increased membrane calcium ion permeability, or most probably by a combination of these mechanisms.
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Olszanecki, Rafał, Maciej Suski, Aneta Stachowicz, Józef Madej, Beata Bujak-Giżycka, Štefan Zorad, Richard Imrich, Tomasz Brzozowski, and Ryszard Korbut. "Ex vivo assessment of angiotensin metabolism in tissues." In XIIth Conference Biologically Active Peptides. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2011. http://dx.doi.org/10.1135/css201113103.

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Suski, Maciej, Rafał Olszanecki, Józef Madej, Anna Gebska, Beata Bujak-Giżycka, and Ryszard Korbut. "Angiotensin metabolism in rat stomach wall: prevalence of angiotensin-(1-7) formation." In XIth Conference Biologically Active Peptides. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2009. http://dx.doi.org/10.1135/css200911118.

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Tykva, Richard, Petr Šimek, Blanka Bennettová, Josef Holík, Jan Hlaváček, and Libor Havlíček. "Conditions for following the metabolism of oostatic peptides in Neobellieria bullata by mass spectrometry and radiolabelling." In VIIth Conference Biologically Active Peptides. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2001. http://dx.doi.org/10.1135/css200104093.

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Bujak-Giżycka, Beata, Maciej Suski, Rafał Olszanecki, Beata Bystrowska, Aneta Stachowicz, Józef Madej, and Ryszard Korbut. "Angiotensinogen metabolism in aorta of hypertensive rats – pathways of Ang-(1-14) and Ang-(1-12) degradation." In XIIth Conference Biologically Active Peptides. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2011. http://dx.doi.org/10.1135/css201113008.

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Tykva, Richard, Blanka Bennettová, Jan Hlaváček, and Václav Němec. "The fate of an oostatic peptide or its analogs including metabolites in insects Diptera and Orthoptera and its transformation to the next generation." In VIth Conference Biologically Active Peptides. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 1999. http://dx.doi.org/10.1135/css199903057.

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Tykva, Richard, Jiřina Slaninová, Blanka Bennettová, Jan Hlaváček, Bohuslav Černý, Věra Vlasáková, and Václav Němec. "Metabolic cleavage of N- and C-terminal amino acids of an insect oostatic peptide H-Tyr-Asp-Pro-Ala-Pro-OH." In IXth Conference Biologically Active Peptides. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2005. http://dx.doi.org/10.1135/css200508100.

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KALIMULLIN, Marat I., Sai-Suu S. SADI, Alexander N. AVSTRIEVSKIKH, and Valery M. POZNYAKOVSKY. "Biologically Active Phytocomplex for Correction of Carbohydrate Metabolism Disorders Phytocomplex in the Correction of Carbohydrate Metabolism." In XVIII International Scientific and Practical Conference "Modern Trends in Agricultural Production in the World Economy". Sibac, 2020. http://dx.doi.org/10.32743/kuz.agri.2020.12-18.

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Markova, Yu A., L. A. Belovezhets, M. S. Tretyakova, A. M. Cheremnykh, and A. A. Levchuk. "The nature of the carbon source as a modulator of the response of bacteria to biologically active compounds (for example, colchicine and protatranes)." In 2nd International Scientific Conference "Plants and Microbes: the Future of Biotechnology". PLAMIC2020 Organizing committee, 2020. http://dx.doi.org/10.28983/plamic2020.163.

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Abstract:
When assessing the impact of biological active compounds (colchicine and protatranes) on Rhodococcus erythropolis against the background of various carbon sources, an unusual effect of low concentrations of colchicine was revealed, that expressed in sharp stimulation of bacterial metabolism.
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Ványolós, A., B. Kovács, Z. Béni, M. Dékány, B. Krámos, E. Liktor-Busa, P. Zomborszki Zoltán, I. Zupkó, and J. Hohmann. "Hungarian mushrooms as untapped source of natural products: from screening studies to biologically active metabolites." In GA 2017 – Book of Abstracts. Georg Thieme Verlag KG, 2017. http://dx.doi.org/10.1055/s-0037-1608106.

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Reports on the topic "Biologically active metabolite"

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Stifeev, A. I., V. I. Lazarev, and O. V. Nikitina. NEW APPROACHES TO THE DEVELOPMENT OF A BIOLOGICALLY ACTIVE SUPPLEMENT BASED ON BIFIDOBACTERIUM BIFIDUM METABOLITES. FGBOU VO Kursk State Agricultural Academy, Journal Bulletin of the Kursk State Agricultural Academy., 2020. http://dx.doi.org/10.18411/issn1997-0749.2020-05-18.

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