Testacosides A–D, glycoglycerolipids produced by Microbacterium testaceum isolated from Tedania brasiliensis
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Published:2024-01-12
Issue:1
Volume:108
Page:
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ISSN:0175-7598
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Container-title:Applied Microbiology and Biotechnology
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language:en
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Short-container-title:Appl Microbiol Biotechnol
Author:
Quintana-Bulla Jairo I.ORCID, Tonon Luciane A. C.ORCID, Michaliski Lamonielli F.ORCID, Hajdu EduardoORCID, Ferreira Antonio G.ORCID, Berlinck Roberto G. S.ORCID
Abstract
Abstract
Marine bacteria living in association with marine sponges have proven to be a reliable source of biologically active secondary metabolites. However, no studies have yet reported natural products from Microbacterium testaceum spp. We herein report the isolation of a M. testaceum strain from the sponge Tedania brasiliensis. Molecular networking analysis of bioactive pre-fractionated extracts from culture media of M. testaceum enabled the discovery of testacosides A–D. Analysis of spectroscopic data and chemical derivatizations allowed the identification of testacosides A–D as glycoglycerolipids bearing a 1-[α-glucopyranosyl-(1 → 3)-(α-mannopyranosyl)]-glycerol moiety connected to 12-methyltetradecanoic acid for testacoside A (1), 14-methylpentadecanoic acid for testacoside B (2), and 14-methylhexadecanoic acid for testacosides C (3) and D (4). The absolute configuration of the monosaccharide residues was determined by 1H-NMR analysis of the respective diastereomeric thiazolidine derivatives. This is the first report of natural products isolated from cultures of M. testaceum.
Key points
• The first report of metabolites produced by Microbacterium testaceum.
• 1-[α-Glucopyranosyl-(1 → 3)-(α-mannopyranosyl)]-glycerol lipids isolated and identified.
• Microbacterium testaceum strain isolated from the sponge Tedania brasiliensis.
Graphical abstract
Funder
Fundação de Amparo à Pesquisa do Estado de São Paulo
Publisher
Springer Science and Business Media LLC
Subject
Applied Microbiology and Biotechnology,General Medicine,Biotechnology
Reference69 articles.
1. Abdelmohsen UR, Bayer K, Hentschel U (2014) Diversity, abundance and natural products of marine sponge-associated actinomycetes. Nat Prod Rep 31:381–399. https://doi.org/10.1039/c3np70111e 2. Agarwal V, Blanton JM, Podell S, Taton A, Schorn MA, Busch J, Lin Z, Schmidt EW, Jensen PR, Paul VJ, Biggs JS, Golden JW, Allen EE, Moore BS (2017) Metagenomic discovery of polybrominated diphenyl ether biosynthesis by marine sponges. Nat Chem Biol 13:537–543. https://doi.org/10.1038/nchembio.2330 3. Almeida JF, Marques M, Oliveira V, Egas C, Mil-Homens D, Viana R, Cleary DFR, Huang YM, Fialho AM, Teixeira MC, Gomes NCM, Costa R, Keller-Costa T (2023) Marine sponge and octocoral-associated bacteria show versatile secondary metabolite biosynthesis potential and antimicrobial activities against human pathogens. Mar Drugs 21:34. https://doi.org/10.3390/md21010034 4. Aron AT, Gentry EC, McPhail KL, Nothias LF, Nothias-Esposito M, Bouslimani A, Petras D, Gauglitz JM, Sikora N, Vargas F, van der Hooft JJJ, Ernst M, Bin KK, Aceves CM, Caraballo-Rodríguez AM, Koester I, Weldon KC, Bertrand S, Roullier C, Sun K, Tehan RM, Boya PCA, Christian MH, Gutiérrez M, Ulloa AM, Tejeda-Mora JA, Mojica-Flores R, Lakey-Beitia J, Vásquez-Chaves V, Zhang Y, Calderón AI, Tayler N, Keyzers RA, Tugizimana F, Ndlovu N, Aksenov AA, Jarmusch AK, Schmid R, Truman AW, Bandeira N, Wang M, Dorrestein PC (2020) Reproducible molecular networking of untargeted mass spectrometry data using GNPS. Nat Protoc 15:1954–1991. https://doi.org/10.1038/s41596-020-0317-5 5. Balskus EP (2014) Sponge symbionts play defense. Nat Chem Biol 10:611–612. https://doi.org/10.1038/nchembio.1588
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