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In this study, three known indole derivatives (1\u20133) were isolated from cold-seep-derived Halomonas meridiana OUCLQ22-B7. Subsequently, two-new indole dimers, meribisindole A (4) and meribisindole B (5), with nine known metabolites (6\u201314) were obtained via indole precursor feeding strategy. The structure of these compounds was elucidated via a combination of spectroscopic methods and circular dichroism (CD) measurement. Antimicrobial assays revealed that compounds 4, 7 and 8 exhibited potent inhibitory activity against Fusarium oxysporum CICC 41029 with minimal inhibitory concentrations (MICs) of 0.39\u221212.5 \u03bcg\/mL, and compound 11 showed significant growth inhibition against Staphylococcus aureus CCARM 3090 with MIC value at 0.098 \u03bcg\/mL.<\/jats:p>","DOI":"10.3390\/md24010016","type":"journal-article","created":{"date-parts":[[2025,12,28]],"date-time":"2025-12-28T23:54:36Z","timestamp":1766966076000},"page":"16","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Discovery of Antimicrobial Oligoindoles from a Cold-Seep-Derived Halomonas Strain"],"prefix":"10.3390","volume":"24","author":[{"given":"Yunchen","family":"Yan","sequence":"first","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhiting","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9662-3664","authenticated-orcid":false,"given":"Hongcheng","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junpeng","family":"Sun","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1598-3217","authenticated-orcid":false,"given":"Wenli","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China"},{"name":"State Key Laboratory for Crop Stress Resistance and High-Efficiency Production, Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Xianyang 712100, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fei","family":"Xiao","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,12,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Cong, M.J., Pang, X.Y., Zhao, K., Song, Y., Liu, Y.H., and Wang, J.F. (2022). Deep-Sea Natural Products from Extreme Environments: Cold Seeps and Hydrothermal Vents. Mar. Drugs, 20.","DOI":"10.3390\/md20060404"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Zhou, Y.L., Mara, P., Cui, G.J., Edgcomb, V.P., and Wang, Y. (2022). Microbiomes in the Challenger Deep slope and bottom-axis sediments. Nat. Commun., 13.","DOI":"10.1038\/s41467-022-29144-4"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Wu, S.M., Liu, G., Zhou, S.N., Sha, Z.X., and Sun, C.M. (2019). Characterization of Antifungal Lipopeptide Biosurfactants Produced by Marine Bacterium Bacillus sp. CS30. Mar. Drugs, 17.","DOI":"10.3390\/md17040199"},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Yan, L.H., Du, F.Y., Li, X.M., Yang, S.Q., Wang, B.G., and Li, X. (2023). Antibacterial Indole Diketopiperazine Alkaloids from the Deep-Sea Cold Seep-Derived Fungus Aspergillus chevalieri. Mar. Drugs, 21.","DOI":"10.3390\/md21030195"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1021\/acs.jnatprod.4c00132","article-title":"Phenylhydrazone Alkaloids from the Deep-Sea Cold Seep Derived Fungus Talaromyces amestolkiae HDN21-0307","volume":"87","author":"Wu","year":"2024","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Zhang, J., Yan, X., Park, H., Scrutton, N.S., Chen, T., and Chen, G.Q. (2024). Nonsterile microbial production of chemicals based on Halomonas spp. Curr. Opin. Biotechnol., 85.","DOI":"10.1016\/j.copbio.2023.103064"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1016\/j.ymben.2025.03.001","article-title":"The halo of future bio-industry based on engineering Halomonas","volume":"90","author":"Yan","year":"2025","journal-title":"Metab. Eng."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Oliva, G., Di Stasio, L., Vigliotta, G., Guarino, F., Cicatelli, A., and Castiglione, S. (2023). Exploring the Potential of Four Novel Halotolerant Bacterial Strains as Plant-Growth-Promoting Rhizobacteria (PGPR) under Saline Conditions. Appl. Sci., 13.","DOI":"10.3390\/app13074320"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1038\/ja.2006.12","article-title":"New aminophenoxazinones from a marine Halomonas sp.: Fermentation, structure elucidation, and biological activity","volume":"59","author":"Bitzer","year":"2006","journal-title":"J. Antibiot."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Li, Y.H., Liu, L., Zhang, G.X., He, N., Guo, W.Q., Hong, B., and Xie, Y.Y. (2020). Potashchelins, a Suite of Lipid Siderophores Bearing Both L-threo and L-erythro Beta-Hydroxyaspartic Acids, Acquired From the Potash-Salt-Ore-Derived Extremophile Halomonas sp. MG34. Front. Chem., 8.","DOI":"10.3389\/fchem.2020.00197"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Zhang, X.Y., Wu, K.Y., Han, Z., Chen, Z.H., Liu, Z.Y., Sun, Z.W., Shao, L.Y., Zhao, Z.L., and Zhou, L. (2022). Microbial diversity and biogeochemical cycling potential in deep-sea sediments associated with seamount, trench, and cold seep ecosystems. Front. Microbiol., 13.","DOI":"10.3389\/fmicb.2022.1029564"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Ma, Q., Zhang, X.W., and Qu, Y.Y. (2018). Biodegradation and Biotransformation of Indole: Advances and Perspectives. Front. Microbiol., 9.","DOI":"10.3389\/fmicb.2018.02625"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1469","DOI":"10.1039\/D0NP00063A","article-title":"Enzymatic dimerization in the biosynthetic pathway of microbial natural products","volume":"38","author":"Liu","year":"2021","journal-title":"Nat. Prod. Rep."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Zhang, Z.L., Xu, H.N., Gong, C.M., Li, Y.Z., Song, X.M., Li, Y.M., Zhang, D.D., and Wang, R. (2025). Microorganism-Derived Bisindole Alkaloids With Anticancer Potential and Their Mechanisms: A Comprehensive Review. Chem. Biodivers., 22.","DOI":"10.1002\/cbdv.202402398"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"432","DOI":"10.1093\/nutrit\/nuw010","article-title":"Chemopreventive properties of 3,3\u2032-diindolylmethane in breast cancer: Evidence from experimental and human studies","volume":"74","author":"Thomson","year":"2016","journal-title":"Nutr. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1517\/13543776.2015.1019865","article-title":"Indirubin derivatives: A patent review (2010-present)","volume":"25","author":"Vougogiannopoulou","year":"2015","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1002\/ijch.201100130","article-title":"Indigo and Tyrian Purple\u2014From Ancient Natural Dyes to Modern Organic Semiconductors","volume":"52","author":"Glowacki","year":"2012","journal-title":"Isr. J. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"791","DOI":"10.1002\/hlca.200900360","article-title":"Two New Indole Alkaloids from the Marine-Derived Bacterium Aeromonas sp CB101","volume":"93","author":"Cai","year":"2010","journal-title":"Helv. Chim. Acta"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3172","DOI":"10.1016\/j.tetlet.2017.07.005","article-title":"Cytotoxic indole alkaloids from Pseudovibrio denitrificans BBCC725","volume":"58","author":"Rodrigues","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"7319","DOI":"10.1039\/D5GC01951F","article-title":"Enzymatic synthesis of health-beneficial oligoindoles using peroxidase","volume":"27","author":"Liu","year":"2025","journal-title":"Green Chem."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Liu, K.X., Chen, W., Xiao, Y.G., Zheng, Y., Xie, X.Y., Li, W.L., Wang, H.M., Wang, H., Lin, Y.N., and Ye, J.W. (2025). Metabolic engineering of Halomonas for effective production of tryptophan-derived compounds. Chem. Eng. J., 512.","DOI":"10.1016\/j.cej.2025.162616"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"716","DOI":"10.1099\/ijs.0.038075-0","article-title":"Introducing EzTaxon-e: A prokaryotic 16S rRNA gene sequence database with phylotypes that represent uncultured species","volume":"62","author":"Kim","year":"2012","journal-title":"Int. J. Syst. Evol. Microbiol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7693","DOI":"10.1021\/acsomega.1c00020","article-title":"A Cyclic Dipeptide from Marine Fungus Penicillium chrysogenum DXY-1 Exhibits Anti-quorum Sensing Activity","volume":"6","author":"Yu","year":"2021","journal-title":"ACS Omega"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1007\/s10600-024-04369-5","article-title":"Secondary Metabolites from the Mangroves-Derived Streptomyces sp. Scsio 41396 and Their Anti-Enzyme Activity","volume":"60","author":"Yuan","year":"2024","journal-title":"Chem. Nat. Compd."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"789","DOI":"10.1080\/14786419.2023.2201882","article-title":"Chemical constituents from the heterotrophic marine microalgae Aurantiochytrium sp. SC145 and their antimicrobial activities","volume":"38","author":"Thuy","year":"2024","journal-title":"Nat. Prod. Res."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Yuan, M.X., Qiu, Y., Ran, Y.Q., Feng, G.K., Deng, R., Zhu, X.F., Lan, W.J., and Li, H.J. (2019). Exploration of Indole Alkaloids from Marine Fungus Pseudallescheria boydii F44-1 Using an Amino Acid-Directed Strategy. Mar. Drugs, 17.","DOI":"10.3390\/md17020077"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Chen, Y.X., Xu, M.Y., Li, H.J., Zeng, K.J., Ma, W.Z., Tian, G.B., Xu, J., Yang, D.P., and Lan, W.J. (2017). Diverse Secondary Metabolites from the Marine-Derived Fungus Dichotomomyces cejpii F31-1. Mar. Drugs, 15.","DOI":"10.3390\/md15110339"},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Wu, D.L., Li, H.J., Smith, D.R., Jaratsittisin, J., Xia-Ke-Er, X., Ma, W.Z., Guo, Y.W., Dong, J., Shen, J., and Yang, D.P. (2018). Polyketides and Alkaloids from the Marine-Derived Fungus Dichotomomyces cejpii F31-1 and the Antiviral Activity of Scequinadoline A against Dengue Virus. Mar. Drugs, 16.","DOI":"10.3390\/md16070229"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4564","DOI":"10.1002\/ejoc.201300133","article-title":"One-Pot Synthesis of Camalexins and 3,3\u2032-Biindoles by the Masuda Borylation-Suzuki Arylation (MBSA) Sequence","volume":"2013","author":"Tasch","year":"2013","journal-title":"Eur. J. Org. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"412","DOI":"10.1016\/j.ultsonch.2010.07.016","article-title":"Efficient and green synthesis of bis(indolyl)methanes catalyzed by ABS in aqueous media under ultrasound irradiation","volume":"18","author":"Li","year":"2011","journal-title":"Ultrason. Sonochem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1587","DOI":"10.1021\/np50113a022","article-title":"Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus","volume":"57","author":"Bell","year":"1994","journal-title":"J. Nat. Prod."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"22346","DOI":"10.1039\/c3ra44693j","article-title":"Bismuth triflate-catalyzed condensation of indoles with acetone","volume":"3","author":"Shelke","year":"2013","journal-title":"RSC Adv."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"752","DOI":"10.1039\/C0OB00472C","article-title":"Tris(indolyl)methene molecule as an anion receptor and colorimetric chemosensor: Tunable selectivity and sensitivity for anions","volume":"9","author":"Wang","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"494","DOI":"10.2174\/1570178614666170511164853","article-title":"1,4-Diazabicyclo 2.2.2 octanium Diacetate under Grinding: Efficient and Eco-Friendly Process for the Synthesis of Symmetric, Unsymmetric and New Bis di(indolyl)indolin-2-one","volume":"14","author":"Fekri","year":"2017","journal-title":"Lett. Org. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2156","DOI":"10.3390\/md12042156","article-title":"Two New Cytotoxic Indole Alkaloids from a Deep-Sea Sediment Derived Metagenomic Clone","volume":"12","author":"Yan","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Lee, J., Kim, J., Song, J.E., Song, W.S., Kim, E.J., Kim, Y.G., Jeong, H.J., Kim, H.R., Choi, K.Y., and Kim, B.G. (2021). Production of Tyrian purple indigoid dye from tryptophan in Escherichia coli. Nat. Chem. Biol., 17.","DOI":"10.1038\/s41589-020-00684-4"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"8528","DOI":"10.1021\/acscatal.4c02178","article-title":"Molecular Insights into the One-Carbon Loss Oxidation of Indole-3-acetic Acid","volume":"14","author":"Cheng","year":"2024","journal-title":"ACS Catal."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3022","DOI":"10.1093\/molbev\/msab120","article-title":"MEGA11 Molecular Evolutionary Genetics Analysis Version 11","volume":"38","author":"Tamura","year":"2021","journal-title":"Mol. Biol. Evol."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/24\/1\/16\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,12,28]],"date-time":"2025-12-28T23:56:14Z","timestamp":1766966174000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/24\/1\/16"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,12,26]]},"references-count":38,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2026,1]]}},"alternative-id":["md24010016"],"URL":"https:\/\/doi.org\/10.3390\/md24010016","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,12,26]]}}}