{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T00:38:50Z","timestamp":1759970330286,"version":"build-2065373602"},"reference-count":46,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2025,1,22]],"date-time":"2025-01-22T00:00:00Z","timestamp":1737504000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"2014\u20132020 ERDF Operational Programme","award":["FEDER-UCA18-105749"],"award-info":[{"award-number":["FEDER-UCA18-105749"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Thiochroman derivatives are highly versatile molecules widely used for the synthesis of novel heterocycles and bioactive compounds. In our study, we conducted the biotransformation of thiochroman-4-ol (1) and 6-chlorothiochroman-4-ol (1a) using the marine-derived fungal strains Emericellopsis maritima BC17 and Purpureocillium lilacinum BC17-2. Biotransformations yielded ten known thiochroman derivatives along with the compound 1-(5-chloro-2-(methylthio)phenyl)propane-1,3-diol (6a), which was described for the first time. Moreover, we successfully characterized the stereoisomers of sulfoxides 3 and 3a. Their structures and absolute configurations were established though comprehensive analyses of NMR, HR ESI-MS, and ECD spectra, as well as by using Mosher\u2019s method. Antimicrobial activity of the isolated metabolites was evaluated against bacterial and fungal human pathogens, specifically Staphylococcus aureus ATCC 29213, Escherichia coli ATCC25922, and Candida albicans HPM-1922816.<\/jats:p>","DOI":"10.3390\/ijms26030908","type":"journal-article","created":{"date-parts":[[2025,1,22]],"date-time":"2025-01-22T07:55:32Z","timestamp":1737532532000},"page":"908","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Biotransformation of Thiochroman Derivatives Using Marine-Derived Fungi: Isolation, Characterization, and Antimicrobial Activity"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8394-0257","authenticated-orcid":false,"given":"Jorge R.","family":"Viru\u00e9s-Segovia","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"},{"name":"Instituto de Investigaci\u00f3n en Biomol\u00e9culas (INBIO), Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1965-3645","authenticated-orcid":false,"given":"Cristina","family":"Pinedo-Rivilla","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"},{"name":"Instituto de Investigaci\u00f3n en Biomol\u00e9culas (INBIO), Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Salvador","family":"Mu\u00f1oz-Mira","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matilde","family":"Ansino","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5754-5923","authenticated-orcid":false,"given":"Victoria E.","family":"Gonz\u00e1lez-Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Laboratorio de Microbiolog\u00eda, Departamento de Biomedicina, Biotecnolog\u00eda y Salud P\u00fablica, Facultad de Ciencias del Mar y Ambientales, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3123-4606","authenticated-orcid":false,"given":"Abdellah","family":"Ezzanad","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0101-6701","authenticated-orcid":false,"given":"F\u00e1tima","family":"Gal\u00e1n-S\u00e1nchez","sequence":"additional","affiliation":[{"name":"Servicio de Microbiolog\u00eda, Hospital Universitario Puerta del Mar, 11009 C\u00e1diz, Spain"},{"name":"Instituto de investigaci\u00f3n e Innovaci\u00f3n Biom\u00e9dica de C\u00e1diz (INIBICA), 11009 C\u00e1diz, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5307-4164","authenticated-orcid":false,"given":"Rosa","family":"Dur\u00e1n-Patr\u00f3n","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"},{"name":"Instituto de Investigaci\u00f3n en Biomol\u00e9culas (INBIO), Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5329-9582","authenticated-orcid":false,"given":"Josefina","family":"Aleu","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica, Facultad de Ciencias, Universidad de C\u00e1diz, 11510 Puerto Real, Spain"},{"name":"Instituto de Investigaci\u00f3n en Biomol\u00e9culas (INBIO), Universidad de C\u00e1diz, 11510 Puerto Real, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,1,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"196","DOI":"10.1016\/j.biortech.2011.11.131","article-title":"Industrial biotransformations in the synthesis of building blocks leading to enantiopure drugs","volume":"115","author":"Hoyos","year":"2012","journal-title":"Bioresour. Technol."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Viru\u00e9s-Segovia, J.R., Mu\u00f1oz-Mira, S., Dur\u00e1n-Patr\u00f3n, R., and Aleu, J. (2023). Marine-derived fungi as biocatalysts. Front. Microbiol., 14.","DOI":"10.3389\/fmicb.2023.1125639"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1007\/s10661-016-5475-0","article-title":"Marine fungi isolated from Chilean fjord sediments can degrade oxytetracycline","volume":"188","author":"Novoa","year":"2016","journal-title":"Environ. Monit. Assess."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Batista-Garc\u00eda, R.A., Sutton, T., Jackson, S.A., Tovar-Herrera, O.E., Balc\u00e1zar-L\u00f3pez, E., S\u00e1nchez-Carbente, M.D.R., S\u00e1nchez-Reyes, A., Dobson, A.D.W., and Folch-Mallol, J.L. (2017). Characterization of lignocellulolytic activities from fungi isolated from the deep-sea sponge Stelletta normani. PLoS ONE, 12.","DOI":"10.1371\/journal.pone.0173750"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1007\/978-981-10-4801-2_54","article-title":"Biological degradation of Aflatoxin B1 by Emericellopsis sp. 1912 and Sarocladium sp. 10A","volume":"444","author":"Wang","year":"2018","journal-title":"Lect. Notes Electr. Eng."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"846","DOI":"10.1080\/15226514.2020.1860901","article-title":"Identification of degrader bacteria and fungi enriched in rhizosphere soil from a toluene phytoremediation site using DNA stable isotope probing","volume":"23","author":"BenIsrael","year":"2021","journal-title":"Int. J. Phytoremediat."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1004","DOI":"10.4014\/jmb.1211.11016","article-title":"Study of the production of alkaline keratinases in submerged cultures as an alternative for solid waste treatment generated in leather technology","volume":"23","author":"Cavello","year":"2013","journal-title":"J. Microbiol. Biotechnol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1007\/s10532-012-9584-3","article-title":"Fungal biodegradation of phthalate plasticizer in situ","volume":"24","author":"Pradeep","year":"2013","journal-title":"Biodegradation"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1080\/17415990802382882","article-title":"Thiochroman-4-ones: Synthesis and reactions","volume":"29","author":"Bondock","year":"2008","journal-title":"J. Sulfur. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Chouch\u00e8ne, N., Toumi, A., Boudriga, S., Edziri, H., Sobeh, M., Abdelfattah, M.A.O., Askri, M., Knorr, M., Strohmann, C., and Brieger, L. (2022). Antimicrobial activity and DFT studies of a novel set of spiropyrrolidines tethered with thiochroman-4-one\/chroman-4-one scaffolds. Molecules, 27.","DOI":"10.3390\/molecules27030582"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"904","DOI":"10.1248\/cpb.c17-00274","article-title":"Design, synthesis, antifungal activity and molecular docking of thiochroman-4-one derivatives","volume":"65","author":"Zhong","year":"2017","journal-title":"Chem. Pharm. Bull."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2124","DOI":"10.1002\/jhet.4338","article-title":"Design, synthesis, and bioactivity evaluation of novel thiochromanone derivatives containing an oxime or oxime ether moiety","volume":"58","author":"Yu","year":"2021","journal-title":"J. Heterocycl. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Xiao, L., Yu, L., Li, P., Chi, J., Tang, Z., Li, J., Tan, S., and Wang, X. (2021). Design, synthesis, and bioactivity evaluation of new thiochromanone derivatives containing a carboxamide moiety. Molecules, 26.","DOI":"10.3390\/molecules26154391"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5354088","DOI":"10.1155\/2022\/5354088","article-title":"Synthesis and bioactivity evaluation of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties","volume":"2022","author":"Yu","year":"2022","journal-title":"J. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1036","DOI":"10.1021\/acs.jnatprod.7b00298","article-title":"Metabolism of antifungal thiochroman-4-ones by Trichoderma viride and Botrytis cinerea","volume":"81","author":"Collado","year":"2018","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1016\/j.jsps.2017.04.040","article-title":"New chroman-4-one\/thiochroman-4-one derivatives as potential anticancer agents","volume":"25","author":"Demirayak","year":"2017","journal-title":"Saudi Pharm. J."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"11","DOI":"10.2174\/1874104500701010011","article-title":"Heteroarotinoids with anti-cancer activity against ovarian cancer cells","volume":"1","author":"Le","year":"2007","journal-title":"Open Med. Chem. J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1985","DOI":"10.1002\/chin.200347130","article-title":"Synthesis of novel tricyclic heterocyclic compounds as potential anticancer agents using chromanone and thiochromanone as synthons","volume":"34","author":"Hammam","year":"2003","journal-title":"ChemInform"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"630","DOI":"10.1007\/s00044-020-02503-w","article-title":"Synthesis and anticancer activities of thiosemicarbazones derivatives of thiochromanones and related scaffolds","volume":"29","author":"Song","year":"2020","journal-title":"Med. Chem. Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1016\/j.apsb.2012.10.005","article-title":"Synthesis and antiviral activities of a novel class of thioflavone and flavonoid analogues","volume":"2","author":"Zhang","year":"2012","journal-title":"Acta Pharm. Sin. B"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Ortiz, C., Echeverri, F., Robledo, S., Lanari, D., Curini, M., Qui\u00f1ones, W., and Vargas, E. (2020). Synthesis and evaluation of antileishmanial and cytotoxic activity of benzothiopyrane derivatives. Molecules, 25.","DOI":"10.3390\/molecules25040800"},{"key":"ref_22","first-page":"11","article-title":"Hydrazone derivatives enhance antileishmanial activity of thiochroman-4-ones","volume":"23","author":"Vargas","year":"2018","journal-title":"Molecules"},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Vargas, E., Echeverri, F., V\u00e9lez, I.D., Robledo, S.M., and Qui\u00f1ones, W. (2017). Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents. Molecules, 22.","DOI":"10.3390\/molecules22122041"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1763","DOI":"10.1016\/j.ejmech.2008.03.028","article-title":"Synthesis and antibacterial activity of some new 2,3-dimethoxy-3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl)chromanones. Eur","volume":"44","author":"Prakash","year":"2009","journal-title":"J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1016\/S0957-4166(00)82112-6","article-title":"Preparation of homochiral chroman-4-ols and thiochroman-4-ols by microbial biotransformation","volume":"2","author":"Holland","year":"1991","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Viru\u00e9s-Segovia, J.R., Mill\u00e1n, C., Pinedo, C., Gonz\u00e1lez-Rodr\u00edguez, V.E., Papaspyrou, S., Zorrilla, D., Mackenzie, T.A., Ramos, M.C., de la Cruz, M., and Aleu, J. (2023). New eremophilane-type sesquiterpenes from the marine sediment-derived fungus Emericellopsis maritima BC17 and their cytotoxic and antimicrobial activities. Mar. Drugs, 21.","DOI":"10.3390\/md21120634"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1111\/j.1574-6968.2011.02322.x","article-title":"Purpureocillium, a new genus for the medically important Paecilomyces lilacinus","volume":"321","author":"Houbraken","year":"2011","journal-title":"FEMS Microbiol. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3176","DOI":"10.1016\/j.jorganchem.2005.03.048","article-title":"Ruthenium-catalyzed reduction of racemic tricarbonyl(H6-aryl ketone)chromium complexes using transfer hydrogenation: A simple alternative to the resolution of planar chiral organometallics","volume":"690","author":"Ursini","year":"2005","journal-title":"J. Organomet. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2659","DOI":"10.1016\/j.tetasy.2009.11.009","article-title":"Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman, and thiochroman-containing ketones","volume":"20","author":"Stepanenko","year":"2009","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2915","DOI":"10.1016\/S0957-4166(01)00508-0","article-title":"A practical guide for the assignment of the absolute configuration of alcohols, amines and carboxylic acids by NMR","volume":"12","author":"Seco","year":"2001","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6819","DOI":"10.1016\/0040-4020(95)00315-Y","article-title":"Neighbouring group effects in a pummerer-type rearrangement: A facile entry into 3,1-benzoxathiins","volume":"51","author":"Kersey","year":"1995","journal-title":"Tetrahedron"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"141","DOI":"10.3987\/COM-09-S(S)34","article-title":"Asymmetric hydrogenation of aromatic heterocyclic ketones catalyzed by the MsDPEN\u2013Cp* Ir (III) complex","volume":"80","author":"Ohkuma","year":"2010","journal-title":"Heterocycles"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2647","DOI":"10.1039\/C7OB00021A","article-title":"Metal- and additive-free oxygen-atom transfer reaction: An efficient and chemoselective oxidation of sulfides to sulfoxides with cyclic diacyl peroxides","volume":"15","author":"Gan","year":"2017","journal-title":"Org. Biomol. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2540","DOI":"10.1002\/adsc.201500288","article-title":"ansa-Ruthenium(II) complexes of R2NSO2DPEN-(CH2)n(\u03b76-aryl) conjugate ligands for asymmetric transfer hydrogenation of aryl ketones","volume":"357","author":"Stephan","year":"2015","journal-title":"Adv. Synth. Catal."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"191","DOI":"10.3987\/COM-08-S(N)37","article-title":"Asymmetric oxidation of cyclic sulfides catalyzed by an aluminum(salalen) complex as the catalyst","volume":"76","author":"Katsuki","year":"2008","journal-title":"Heterocycles"},{"key":"ref_36","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Revision A.01, Gaussian Inc."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density\u2014Functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/0009-2614(96)00440-X","article-title":"Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory","volume":"256","author":"Bauernschmitt","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"4439","DOI":"10.1063\/1.475855","article-title":"Molecular excitation energies to high-lying bound states from time-dependent\u2009density-functional\u2009response\u2009theory: Characterization\u2009and correction\u2009of\u2009the\u2009time-dependent\u2009local\u2009density\u2009approximation ionization threshold","volume":"108","author":"Casida","year":"1998","journal-title":"J. Chem. Phys."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3032","DOI":"10.1063\/1.474659","article-title":"A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics","volume":"107","author":"Mennucci","year":"1997","journal-title":"J. Chem. Phys."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"10506","DOI":"10.1021\/jp971959k","article-title":"Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: Theoretical bases, computational implementation, and numerical applications","volume":"101","author":"Mennucci","year":"1997","journal-title":"J. Phys. Chem. B"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","article-title":"Quantum mechanical continuum solvation models","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_44","unstructured":"Clinical and Laboratory Standards Institute (2020). Performance Standards for Antimicrobial Susceptibility Testing, CLSI Supplement M100. [30th ed.]."},{"key":"ref_45","unstructured":"(2024, February 15). EUropean Committee on Antimicrobial Susceptibility Testing (EUCAST). Methods for the Determination of Broth Dilution Minimum Inhibitory Concentrations of Antifungal Agents for Yeasts. Version 7.4. Available online: https:\/\/www.eucast.org\/astoffungi\/methodsinantifungalsusceptibilitytesting\/susceptibility_testing_of_yeasts."},{"key":"ref_46","unstructured":"(2019). International Organization for Standardization (ISO). Susceptibility Testing of Infectious Agents and Evaluation of Performance of Antimicrobial Susceptibility Test Devices\u2014Part 1: Broth Micro-Dilution Reference Method for Testing the In Vitro Activity of Antimicrobial Agents Against Rapidly Growing Aerobic Bacteria, 2nd ed. (Standard No. ISO 20776-1)."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/3\/908\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,8]],"date-time":"2025-10-08T10:33:40Z","timestamp":1759919620000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/3\/908"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,22]]},"references-count":46,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2025,2]]}},"alternative-id":["ijms26030908"],"URL":"https:\/\/doi.org\/10.3390\/ijms26030908","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2025,1,22]]}}}