Novel Aeruginosin-865 from Nostoc sp. as a Potent Anti-inflammatory Agent

Aeruginosin‐865 (Aer‐865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin‐type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic ana...

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Published inChembiochem : a European journal of chemical biology Vol. 14; no. 17; pp. 2329 - 2337
Main Authors Kapuścik, Aleksandra, Hrouzek, Pavel, Kuzma, Marek, Bártová, Simona, Novák, Petr, Jokela, Jouni, Pflüger, Maren, Eger, Andreas, Hundsberger, Harald, Kopecký, Jiří
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 25.11.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Active Transport, Cell Nucleus - drug effects
anti-inflammatory
Anti-inflammatory agents
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - isolation & purification
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Biochemistry & Molecular Biology
Cell Line
Chemistry, Medicinal
cyanobacteria
Dose-Response Relationship, Drug
Down-Regulation - drug effects
drug discovery
Glycopeptides - chemistry
Glycopeptides - isolation & purification
Glycopeptides - pharmacology
Humans
Intercellular Adhesion Molecule-1 - biosynthesis
Interleukin-8 - biosynthesis
Life Sciences & Biomedicine
Lipopeptides - chemistry
Lipopeptides - isolation & purification
Lipopeptides - pharmacology
Liquid chromatography
Mass spectrometry
Molecular Structure
NF-kappa B - metabolism
NMR spectroscopy
Nostoc - chemistry
Nostoc - growth & development
peptides
Pharmacology & Pharmacy
Protein Transport - drug effects
Science & Technology
Structure-Activity Relationship
Translocation
MAP KINASE
C-PHYCOCYANIN
peptides
ALPHA
NODULARIA-SPUMIGENA
ADHESION
INHIBITION
drug discovery
PATHWAY
cyanobacteria
ENDOTHELIAL-CELLS
anti-inflammatory
NMR spectroscopy
NF-KAPPA-B
TRANSCRIPTIONAL REGULATION
Online AccessGet full text
ISSN1439-4227
1439-7633
1439-7633
DOI10.1002/cbic.201300246

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Abstract Aeruginosin‐865 (Aer‐865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin‐type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one‐ and two‐dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D‐Hpla, D‐Leu, 5‐OH‐Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL‐8 and ICAM‐1 in hTNF‐α‐stimulated HLMVECs. Aer‐865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL−1 ((4.0±1.7) μM) and (50.0±13.4) μg mL−1 ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti‐inflammatory effect of Aer‐865 was directly associated with inhibition of NF‐κB translocation to the nucleus. Moreover, Aer‐865 did not show any cytotoxic effect. Calm down: Anti‐inflammatory activity of the new aeruginosin Aer‐865 is reported. In TNF‐α‐stimulated endothelial cells, Aer‐865 downregulates IL‐8 and ICAM‐1 and is associated with inhibition of NF‐κB translocation to the nucleus. In this respect Aer‐865 can be considered an interesting immunomodulatory agent.
AbstractList Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF-α-stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL(-1) ((4.0±1.7) μM) and (50.0±13.4) μg mL(-1) ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-κB translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect.Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF-α-stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL(-1) ((4.0±1.7) μM) and (50.0±13.4) μg mL(-1) ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-κB translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect.
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukesová 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF-[alpha]-stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5±1.5) µgmL-1 ((4.0±1.7) µM) and (50.0±13.4) µgmL-1 ((57.8±15.5) µM), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-[kappa]B translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect. [PUBLICATION ABSTRACT]
Aeruginosin‐865 (Aer‐865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin‐type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc . Mass spectrometry, chemical and spectroscopic analysis as well as one‐ and two‐dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D ‐Hpla, D ‐Leu, 5‐OH‐Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL‐8 and ICAM‐1 in hTNF‐α‐stimulated HLMVECs. Aer‐865 showed significant reduction of both: with EC 50 values of (3.5±1.5) μg mL −1 ((4.0±1.7) μ M ) and (50.0±13.4) μg mL −1 ((57.8±15.5) μ M ), respectively. Confocal laser scanning microscopy revealed that the anti‐inflammatory effect of Aer‐865 was directly associated with inhibition of NF‐κB translocation to the nucleus. Moreover, Aer‐865 did not show any cytotoxic effect.
Aeruginosin‐865 (Aer‐865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin‐type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one‐ and two‐dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D‐Hpla, D‐Leu, 5‐OH‐Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL‐8 and ICAM‐1 in hTNF‐α‐stimulated HLMVECs. Aer‐865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL−1 ((4.0±1.7) μM) and (50.0±13.4) μg mL−1 ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti‐inflammatory effect of Aer‐865 was directly associated with inhibition of NF‐κB translocation to the nucleus. Moreover, Aer‐865 did not show any cytotoxic effect. Calm down: Anti‐inflammatory activity of the new aeruginosin Aer‐865 is reported. In TNF‐α‐stimulated endothelial cells, Aer‐865 downregulates IL‐8 and ICAM‐1 and is associated with inhibition of NF‐κB translocation to the nucleus. In this respect Aer‐865 can be considered an interesting immunomodulatory agent.
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF-α-stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5±1.5) μg mL(-1) ((4.0±1.7) μM) and (50.0±13.4) μg mL(-1) ((57.8±15.5) μM), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-κB translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect.
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukeova 30/93, is the first aeruginosin-type peptide containing both a fatty acid and a carbohydrate moiety, and is the first aeruginosin to be found in the genus Nostoc. Mass spectrometry, chemical and spectroscopic analysis as well as one- and two-dimensional NMR and chiral HPLC analysis of Marfey derivatives were applied to determine the peptidic sequence: D-Hpla, D-Leu, 5-OH-Choi, Agma, with hexanoic and mannopyranosyl uronic acid moieties linked to Choi. We used an AlphaLISA assay to measure the levels of proinflammatory mediators IL-8 and ICAM-1 in hTNF--stimulated HLMVECs. Aer-865 showed significant reduction of both: with EC50 values of (3.5 +/- 1.5) gmL(-1) ((4.0 +/- 1.7) M) and (50.0 +/- 13.4) gmL(-1) ((57.8 +/- 15.5) M), respectively. Confocal laser scanning microscopy revealed that the anti-inflammatory effect of Aer-865 was directly associated with inhibition of NF-B translocation to the nucleus. Moreover, Aer-865 did not show any cytotoxic effect.
Author Bártová, Simona
Kuzma, Marek
Novák, Petr
Kapuścik, Aleksandra
Hundsberger, Harald
Kopecký, Jiří
Pflüger, Maren
Eger, Andreas
Hrouzek, Pavel
Jokela, Jouni
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  organization: Department of Phototrophic Microorganisms-ALGATECH, Institute of Microbiology, Academy of Science of the Czech Republic, Opatovický mlýn, 379 81 Třeboň (Czech Republic)
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/24123716$$D View this record in MEDLINE/PubMed
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ISSN 1439-4227
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Issue 17
Keywords MAP KINASE
C-PHYCOCYANIN
peptides
ALPHA
NODULARIA-SPUMIGENA
ADHESION
INHIBITION
drug discovery
PATHWAY
cyanobacteria
ENDOTHELIAL-CELLS
anti-inflammatory
NMR spectroscopy
NF-KAPPA-B
TRANSCRIPTIONAL REGULATION
Language English
License Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Notes Center for Algal Biotechnology Třeboň-ALGATECH - No. CZ. 1.05/21.00/03.0110
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Ministry of Education of the Czech Republic - No. LH11129
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PublicationDate November 25, 2013
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  year: 2013
  text: November 25, 2013
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PublicationDecade 2010
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PublicationTitle Chembiochem : a European journal of chemical biology
PublicationTitleAbbrev CHEMBIOCHEM
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PublicationYear 2013
Publisher WILEY-VCH Verlag
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Hanessian, S (WOS:000247496200046) 2007; 17
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Hanessian, S (WOS:000269670700052) 2009; 11
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Dittmann, E (WOS:A1997YH49500015) 1997; 26
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Snippet Aeruginosin‐865 (Aer‐865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin‐type peptide containing both a fatty...
Aeruginosin‐865 (Aer‐865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin‐type peptide containing both a fatty...
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukeova 30/93, is the first aeruginosin-type peptide containing both a fatty...
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukešová 30/93, is the first aeruginosin-type peptide containing both a fatty...
Aeruginosin-865 (Aer-865), isolated from terrestrial cyanobacterium Nostoc sp. Lukesová 30/93, is the first aeruginosin-type peptide containing both a fatty...
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SubjectTerms Active Transport, Cell Nucleus - drug effects
anti-inflammatory
Anti-inflammatory agents
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - isolation & purification
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Biochemistry & Molecular Biology
Cell Line
Chemistry, Medicinal
cyanobacteria
Dose-Response Relationship, Drug
Down-Regulation - drug effects
drug discovery
Glycopeptides - chemistry
Glycopeptides - isolation & purification
Glycopeptides - pharmacology
Humans
Intercellular Adhesion Molecule-1 - biosynthesis
Interleukin-8 - biosynthesis
Life Sciences & Biomedicine
Lipopeptides - chemistry
Lipopeptides - isolation & purification
Lipopeptides - pharmacology
Liquid chromatography
Mass spectrometry
Molecular Structure
NF-kappa B - metabolism
NMR spectroscopy
Nostoc - chemistry
Nostoc - growth & development
peptides
Pharmacology & Pharmacy
Protein Transport - drug effects
Science & Technology
Structure-Activity Relationship
Translocation
Title Novel Aeruginosin-865 from Nostoc sp. as a Potent Anti-inflammatory Agent
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https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcbic.201300246
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https://www.ncbi.nlm.nih.gov/pubmed/24123716
https://www.proquest.com/docview/1459126188
https://www.proquest.com/docview/1459564972
Volume 14
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