Published January 31, 2021
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1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity
Authors/Creators
- 1. * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix˜oes, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal
- 2. * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix˜oes, Av. General Norton de Matos s/n, 4450-208, Matosinhos, Portugal & Laborat´orio de Química Orgˆanica, Departamento de Ciˆencias Químicas, Faculdade de Farm´acia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal
- 3. Department of Drug Sciences, Universita`di P´avia, C. So strada Nuova 65, 27100, Pavia, Italy
- 4. Department of Plant Pathology, Faculty of Agriculture, Kasetsart University, Bangkok, 10240, Thailand
- 5. * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal & * & Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Terminal de Cruzeiros do Porto de Leix˜oes, Av. General Norton de Matos s/n, 4450-208,
- 6. * & ICBAS-Instituto de Ciˆencias Biom´edicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal & Instituto de Biologia Molecular e Celular (i3S-IBMC), Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313, Porto, Portugal
- 7. Department of Chemistry, University of Leicester, University Road, Leicester, LE 7 RH, UK
- 8. Departamento de Química & QOPNA, Universidade de Aveiro, 3810-193, Aveiro, Portugal
Description
Kumla, Decha, Sousa, Emilia, Marengo, Alessia, Dethoup, Tida, Pereira, A. J., Gales, Luís, Freitas-Silva, Joana, Costa, Paulo M., Mistry, Sharad, Silva, Artur M.S., Kijjoa, Anake (2021): 1,3-Dioxepine and spiropyran derivatives of viomellein and other dimeric naphthopyranones from cultures of Aspergillus elegans KUFA0015 and their antibacterial activity. Phytochemistry (112575) 181: 1-15, DOI: 10.1016/j.phytochem.2020.112575, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112575
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- urn:lsid:plazi.org:pub:A40BC65E1705D2420A2AC973FFBAFFBD
References
- Alvarado, J.G., Abad-Reyes, J.D., Montealegre, R., Amaro-Luis, J.M., 2013. Napthopyranones from rhizomes of Paepalanthus diffisus. Adv. en Quimica 8, 131-138.
- Austin, A., Petersson, G.A., Frisch, M.J., Dobek, F.J., Scalmani, G., Throssell, K., 2012. A density functional with spherical atom dispersion terms. J. Chem. Theor. Comput. 8, 4989-5007. https://doi.org/10.1021/ct300778e.
- Ayabe, S., Akashi, T., 2006. Cytochrome P450s in flavonoid metabolism. Phytochemistry Rev. 5, 271-282. https://doi.org/10.1007/s11101-006-9007-3.
- Bessa, L.J., Barbosa-Vasconcelos, A., Mendes, A ˆ., Vaz-Pires, P., da Costa, P.M., 2014. High prevalence of multidrug-resistant Escherichia coli and Enterococcus spp. in river water, upstream and downstrea of a wastewater treatment plant. J. Water Health 12, 426-435. https://doi.org/10.2166/wh.2014.160.
- Brakhage, A.A., 2013. Regulation of fungal secondary metabolism. Nat. Ver. Microbiol. 11, 21-32. https://doi.org/10.1038/nrmicro2916.
- Bode, S.E., Drochner, D., Muller, M., 2007. Synthesis, biosynthesis, and absolute configuration of vioxanthin. Angew. Chem. Int. Ed. 46, 5916-5920. https://doi.org/ 10.1002/anie.200701014.
- Bredenkamp, M.W., Dillen, J.L., Rooyen, P.H., Steyn, P.S., 1989. Crystal structures and conformational analysis of ochratoxin A and B: probing the chemical structure causing toxicity. J. Chem. Soc., Perkin Trans. 2, 1835-1839. https://doi.org/ 10.1039/P29890001835.
- Buttachon, S., Ramos, A.A., In´acio, A., Dethoup, T., Gales, L., Lee, M., Costa, P.M., Silva, A.M.S., Sekeroglu, N., Rocha, E., Pinto, M.M.M., Pereira, J.A., Kijjoa, A., 2018. Bis -indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus Aspergillus candidus KUFA0062. Mar. Drugs 16, 119. https://doi.org/10.3390/md16040119.
- Chen, W., Lee, M.K., Jefcoate, C., Kim, S.C., Chen, F., Yu, J.H., 2014. Fungal cytochrome p450 monooxygenases: their distribution, structure, functions, family expansion, and evolutionary origin. Genome Biol. Evol. 6, 1620-1634. https://doi.org/ 10.1093/gbe/evu132.
- CLSI, 1999. Method for determining bactericidal activity of antimicrobial agents; Approved Guideline, CLSI Document M26-A. Clinical and Laboratory Standards Institute, Wayne, Pennsylvania, USA.
- CLSI, 2012. Performance standards for antimicrobial susceptibility testing. In: CLSI Document M02-A11, eleventh ed. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
- CLSI, 2017. Performance standards for antimicrobial susceptibility testing. In: CLSI Supplement M100, 27 th ed. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
- CLSI, 2018. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. In: CLSI Standard M07, eleventh ed. Clinical and Laboratory Standards Institute, Wayne, PA, USA.
- Dais, P., Stefanaki, I., Fragaki, G., Mikros, E., 2005. Conformational analysis of ochratoxin A by NMR spectroscopy and computational molecular modeling. J. Phys. Chem. B 109, 16926-16936. https://doi.org/10.1021/jp058035e.
- Durley, R.C., MacMillan, J., Simpson, T.J., 1975. Fungal products- Part XIII. Xanthomegnin, viomellin, rubrosulphin and viopurpurin, pigments from Aspergillus sulphureus and Aspergillus melleeus. J. Chem. Soc., Perkin I, 163-169.
- Geissman, T.A., Crout, D.H.G., 1969. Miscellaneous oxidative process. In: Organic Chemistry of Plant Metabolism. Freeman, Cooper& Company, San Francisco, California, U.S.A, pp. 409-410.
- Hofel ¨, G., R¨oser, K., 1978. Structure of xanthomegnin and related pigments: reinvestigation by 13 C nuclear magnetic resonance spectroscopy. J. Chem. Soc., Chem. Commun. 611-612.
- Inglis, D.O., Binkley, J., Skrzypek, M.S., Arnaud, M.B., Cerqueira, G.C., Shah, P., Wymore, F., Wortman, J.R., Sherlock, G., 2013. Comprehensive annotation of secondary metabolite biosynthetic genes and gene clusters of Aspergillus nidulans,A. fumigatus, A. Niger and A. oryzae. BMC Microbiol. 13, 91. https://doi.org/10.1186/ 1471-2180-13-91.
- Kumla, D., Aung, T.S., Buttachon, S., Dethoup, T., Gales, L., Pereira, J.A., In´acio, A., Costa, P.M., Lee, M., Sekeroglu, N., Silva, A.M.S., Pinto, M.M.M., Kijjoa, A., 2017. A new dihydrochromone dimer and other secondary metabolites from cultures of the marine sponge-associated fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213. Mar. Drugs 15, 375. https://doi.org/10.3390/md15120375.
- Kumla, D., Dethhoup, T., Gales, L., Pereira, J.A., Freitas-Silva, J., Costa, P.M., Silva, A.M. S., Pinto, M.M.M., Kijjoa, A., 2019. Erubesensoic acid, a new polyketide and a xanthonopyrone SPF-3059-26 from the culture of the marine sponge-associated fungus Penicillium erubescens KUFA 0220 and antibacterial activity evaluation of some of its constituents. Molecules 24, 208. https://doi.org/10.3390/ molecules24010208.
- Mulyani, H., Dewi, R.T., 2019. Antibacterial compound from Aspergillus elegans SweF9 an endophytic fungus from macroalgae Euchema sp. Indones. J. Pharm. 30, 217-224.
- Murray, M.G., Thompson, W.F., 1980. Rapid isolation of high molecular weight plant DNA. Nucleic Acids Res. 8, 4321-4325. https://doi.org/10.1093/nar/8.19.4321.
- Ono, E., Nakai, M., Fukui, Y., Tomimori, N., Fukuchi-Mizutani, M., Saito, M., Satake, H., Tanaka, T., Katsuta, M., Umezawa, T., Tanaka, Y., 2006. Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+ )-sesamin. Proc. Natl. Acad. Sci. U. S. A 103, 10116-10121. www.pnas.org/c gi/doi/10.1073pnas.0603865103.
- Prompanya, C., Dethoup, T., Bessa, L.J., Pinto, M.M.M., Gales, L., Costa, P.M., Silva, A.M. S., Kijjoa, A., 2014. New isocoumarin derivatives and meroterpenoids from the marine sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013. Mar. Drugs 12, 5160-5173. https://doi.org/10.3390/md12105160.
- Prompanya, C., Fernandes, C., Cravo, S., Pinto, M.M.M., Dethoup, T., Silva, A.M.S., Kijjoa, A., 2015. A new cyclic hexapeptide and a new isocoumarin derivative from the marine sponge-associated fungus Aspergillus similanensis KUFA 0013. Mar. Drugs 13, 1432-1450. https://doi.org/10.3390/md13031432.
- Samson, R.A., Visagie, C.M., Houbraken, J., Hong, S.-B., Hubka, V., Klaassen, C.H.W., Perrone, G., Seifert, K.A., Susca, A., Tanney, J.B., Varga, V., Kocsub´e, S., Szigeti, G., Yaguchi, T., Frisvad, J.C., 2014. Phylogeny, identification and nomenclature of the genus Aspergillus. Stud. Mycol. 78, 141-173. https://doi.org/10.1016/j. simyco.2014.07.004.
- Sanger, F., Nicklen, S., Coulson, A.R., 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. U.S.A. 72, 5463-5467. https://doi.org/10.1073/ pnas.74.12.5463.
- Simtoes, R.R., Aires-de-Sousa, M., Conceictao, T., Antunes, F., da Costa, P.M., de Lencastre, H., 2011. High prevalence of EMRSA-15 in Portuguese public buses: A worrisome finding. PloS One 6, 1-5. https://doi.org/10.1371/journal. pone.0017630.
- Simpson, T.J., 1977. 13 C Nuclear magnetic resonance spectra and biosynthetic studies of xanthomegnin and related pigments from Aspergillus sulphureus and melleus. J. Chem. Soc. Perkin I, 592-595.
- Sheldrick, G.M., 2008. A short history of SHELX. Acta Crystallogr. A 64, 112-122. https://doi.org/10.1107/S0108767307043930.
- Stepanovic ´, S., Vukovic ´, D., Hola, V., Di Bonaventura, G., Djukic ´, S., Cirkovi ´´c, I., Ruzicka, F., 2007. Quantification of biofilm in microtiter plates: overview of testing conditions and practical recommendations for assessment of biofilm production by staphylococci. Apmis 115, 891-899. https://doi.org/10.1111/j.1600 0463.2007. apm_630.x.
- Steyn, P.S., Holzapfel, C.W., 1967. The synthesis of ochratoxins A and B: metabolites of Aspergillus ochraceus Wilh. Tetrahedron 23, 4449-4461. https://doi.org/10.1016/ S0040-4020(01)88843-8.
- Wang, Y., Wang, L., Wu, F., Liu, F., Wang, Q., Zhang, X., Selvaraj, J.N., Zhao, Y., Xing, F., Yin, W.-B., Liu, Y., 2018. A consensus ochratoxin A biosynthetic pathway: insights from the genome sequence of Aspergillus ochraceus and a comparative genomic analysis. Appl. Environ. Microbiol. 64, e001009-e001018. https://doi.org/10.1128/ AEM.01009-18.
- Xu, L., Meng, W., Cao, C., Wang, J., Shan, W., Wang, Q., 2015. Antibacterial and antifungal compounds from marine fungi. Mar. Drugs 13, 3479-3513. https://doi. org/10.3390/md13063479.
- Xu, X., He, F., Zhang, X., Bao, J., Qi, S., 2013. New mycotoxins from marine-derived fungus Aspergillus sp. SCSGAF0093. Food Chem. Toxicol. 53, 46-51. https://doi.org/ 10.1016/j.fct.2012.11.037.
- Zhang, C.L., Zheng, B.Q., Lao, J.P., Mao, L.J., Chen, S.Y., Kubicek, C.P., Lin, F.C., 2008. Clavatol and patulin formation as the antagonistic principle of Aspergillus clavatonanicus, an endophytic fungus of Taxus mairei. Appl. Microbiol. Biotechnol. 78, 833-840. https://doi.org/10.1007/s00253-008-1371-z.
- Zheng, C.-J., Shao, C.-L., Wu, L.-Y., Chen, M., Wang, K.-L., Zhao, D.-L., Sun, X.-P., Chen, G.-Y., Wang, C.-Y., 2013. Bioactive phenylalanine derivatives and cytochalasins from the soft coral-derived fungus, Aspergillus elegans. Mar. Drugs 11, 2054-2068. https://doi.org/10.3390/md11062054.