Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica Ulrike Groenhagen, Ana Ligia Leandrini De Oliveira, Elisha Fielding, Bradley S. Moore, Stefan Schulz Chembiochem, 2016 Terrestrial bacteria, especially actinomycetes, are known to be prolific producers of volatile compounds. We show here that bacteria from ocean sediments can also release complex bouquets of volatiles. The actinomycete Salinispora tropica produces cyclohexenyl compounds not previously known in nature, such as methyl cyclohex‐2‐ene‐1‐carboxylate (9), methyl 2‐(cyclohex‐2‐en‐1‐yl)acetate (10), methyl (E/Z)‐2‐(cyclohex‐2‐en‐1‐ylidene)acetate (11/12), and related alcohols 8 and 13. These compounds were identified by GC/MS and confirmed by synthesis. In addition, rare spiroacetals, aromatic compounds, short‐chain acids and esters, alcohols, and various cyclic compounds were produced by the bacteria. The biosynthesis of the cyclohexenyl compounds is closely coupled to that of cyclohexenylalanine (4), a building block of salinosporamide A, a proteasome inhibitor produced by S. tropica. Analysis of S. tropica strains that harbor knockouts of the salinosporamide biosynthetic genes salX and salD, coupled with feeding experiments, revealed that 3‐(cyclohex‐2‐en‐1‐yl)‐2‐oxopropanoic acid (60) and 3‐(cyclohex‐2‐en‐1‐ylidene)‐2‐oxopropanoic acid (isomers 61 and 62) are important intermediates in the biosynthesis of salinosporamide A, 4, and 8–13.
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As abelhas" sem-ferrão" dos biomas brasileiros: O Brasil possui a maior biodiversidade de abelhas" sem-ferrão" do planeta, essenciais para o funcionamento dos ecossistemas e … DS Nogueira, A Vollet-Neto, MP Cassinelli, JA Santos-Silva, ... Ciência e Cultura 75 (4), 01-07 , 2023 2023 Citations: 7
Antifungal compounds from Streptomyces associated with attine ants also inhibit Leishmania donovani HE Ortega, LLG Ferreira, WGP Melo, ALL Oliveira, RF Ramos Alvarenga, ... PLOS Neglected Tropical Diseases 13 (8), e0007643 , 2019 2019 Citations: 70
Structural and biosynthetic studies on eremophilenols related to the phytoalexin capsidiol, produced by Botrytis cinerea I Suárez, G da Silva Lima, R Conti, C Pinedo, J Moraga, J Barúa, ... Phytochemistry 154, 10-18 , 2018 2018 Citations: 13
Differential genotoxicity and cytotoxicity of phomoxanthone A isolated from the fungus Phomopsis longicolla in HL60 cells and peripheral blood lymphocytes GB Pavão, VP Venâncio, ALL de Oliveira, LC Hernandes, MR Almeida, ... Toxicology in Vitro 37, 211-217 , 2016 2016 Citations: 22
Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica U Groenhagen, AL Leandrini De Oliveira, E Fielding, BS Moore, S Schulz ChemBioChem 17 (20), 1978-1985 , 2016 2016 Citations: 23
13 Microbial Natural Products R de Felício, AL de Oliveira, M Scopel, HM Debonsi Molecular Diversity of Environmental Prokaryotes, 295 , 2016 2016 Citations: 2
Antibacterial, antifungal and cytotoxic activities exhibited by endophytic fungi from the Brazilian marine red alga Bostrychia tenella (Ceramiales) R de Felício, GB Pavão, ALL de Oliveira, C Erbert, R Conti, MT Pupo, ... Revista Brasileira de Farmacognosia 25 (6), 641-650 , 2015 2015 Citations: 86
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Collision-Induced Dissociation Analysis of Brevianamide A and C in Electrospray Ionization Mass Spectrometry ALL Oliveira, R Vessecchi, NP Lopes, HM Debonsi Journal of the Brazilian Chemical Society 26 (4), 822-827 , 2015 2015 Citations: 1
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MOST CITED SCHOLAR PUBLICATIONS
Antibacterial, antifungal and cytotoxic activities exhibited by endophytic fungi from the Brazilian marine red alga Bostrychia tenella (Ceramiales) R de Felício, GB Pavão, ALL de Oliveira, C Erbert, R Conti, MT Pupo, ... Revista Brasileira de Farmacognosia 25 (6), 641-650 , 2015 2015 Citations: 86
Antifungal compounds from Streptomyces associated with attine ants also inhibit Leishmania donovani HE Ortega, LLG Ferreira, WGP Melo, ALL Oliveira, RF Ramos Alvarenga, ... PLOS Neglected Tropical Diseases 13 (8), e0007643 , 2019 2019 Citations: 70
Marine natural products: chemical and biological potential of seaweeds and their endophytic fungi ALL Oliveira, R Felício, HM Debonsi Revista Brasileira de Farmacognosia 22 (4), 906-920 , 2012 2012 Citations: 52
Biohydroxylation of (−)-ambrox®,(−)-sclareol, and (+)-sclareolide by whole cells of Brazilian marine-derived fungi MP Martins, J Ouazzani, G Arcile, AH Jeller, JPF de Lima, MHR Seleghim, ... Marine Biotechnology 17 (2), 211-218 , 2015 2015 Citations: 42
Chemical constituents from red algae Bostrychia radicans (Rhodomelaceae): new amides and phenolic compounds ALL Oliveira, DB Silva, NP Lopes, HM Debonsi, NS Yokoya Química Nova 35 (11), 2186-2188 , 2012 2012 Citations: 26
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Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica U Groenhagen, AL Leandrini De Oliveira, E Fielding, BS Moore, S Schulz ChemBioChem 17 (20), 1978-1985 , 2016 2016 Citations: 23
Differential genotoxicity and cytotoxicity of phomoxanthone A isolated from the fungus Phomopsis longicolla in HL60 cells and peripheral blood lymphocytes GB Pavão, VP Venâncio, ALL de Oliveira, LC Hernandes, MR Almeida, ... Toxicology in Vitro 37, 211-217 , 2016 2016 Citations: 22
Bioprospecção a partir dos oceanos: conectando a descoberta de novos fármacos aos produtos naturais marinhos R Felício, ALL Oliveira, HM Debonsi Ciência e Cultura 64 (3), 39-42 , 2012 2012 Citations: 17
Bioreduction of Acetophenone Derivatives by Red Marine Algae Bostrychia radicans and B. tenella , and Marine Bacteria Associated AM Mouad, MP Martins, HM Debonsi, ALL de Oliveira, R de Felicio, ... Helvetica Chimica Acta 94 (8), 1506-1514 , 2011 2011 Citations: 16
Structural and biosynthetic studies on eremophilenols related to the phytoalexin capsidiol, produced by Botrytis cinerea I Suárez, G da Silva Lima, R Conti, C Pinedo, J Moraga, J Barúa, ... Phytochemistry 154, 10-18 , 2018 2018 Citations: 13
Bioreduction of fluoroacetophenone derivatives by endophytic fungi isolated from the marine red alga Bostrychia radicans AM Mouad, ALL de Oliveira, HM Debonsi, ALM Porto Biocatalysis 1 (1) , 2015 2015 Citations: 9
As abelhas" sem-ferrão" dos biomas brasileiros: O Brasil possui a maior biodiversidade de abelhas" sem-ferrão" do planeta, essenciais para o funcionamento dos ecossistemas e … DS Nogueira, A Vollet-Neto, MP Cassinelli, JA Santos-Silva, ... Ciência e Cultura 75 (4), 01-07 , 2023 2023 Citations: 7
Bioconversion of acetophenones by marine fungi isolated from marine algae Bostrychia radicans and Sargassum sp. AM Mouad, MP Martins, S Romminger, MHR Seleghim, ALL de Oliveira, ... Biotechnology 7 , 2012 2012 Citations: 7
Avaliação química e biológica de espécimens de Bostrychia radicans (Rhodomelaceae) ALL Oliveira Universidade de São Paulo , 2009 2009 Citations: 7
Chemical composition of guarana flowers and nectar and their ecological significance ALL de Oliveira, MP Muniz, FMA da Silva, AH do Nascimento, ... Biochemical Systematics and Ecology 112, 104769 , 2024 2024 Citations: 6
13 Microbial Natural Products R de Felício, AL de Oliveira, M Scopel, HM Debonsi Molecular Diversity of Environmental Prokaryotes, 295 , 2016 2016 Citations: 2
Collision-Induced Dissociation Analysis of Brevianamide A and C in Electrospray Ionization Mass Spectrometry ALL Oliveira, R Vessecchi, NP Lopes, HM Debonsi Journal of the Brazilian Chemical Society 26 (4), 822-827 , 2015 2015 Citations: 1
Algas e micro-organismos marinhos como fonte de substâ ncias bioativas: quÃmica e biologia de Bostrychia radicans e fungos endofÃticos associados ALL Oliveira Universidade de Sã o Paulo , 2013 2013 Citations: 1
Antitumor and antifungal activities from red algae Bostrychia radicans and B. tenella (Rhodophyta) ALL De Oliveira, R de Felício, LV Costa-Lotufo, MO de Moraes, ... Planta Medica 74 (09), PA153 , 2008 2008 Citations: 1