rdf:type |
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lifeskim:mentions |
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pubmed:issue |
9
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pubmed:dateCreated |
2002-9-27
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pubmed:abstractText |
Preparative-scale incubations with Nocardia sp. NRRL 5646 were conducted to produce new derivatives of the abietane diterpene chemoprotectant and antioxidant carnosic acid (1). Reductive biotransformation of the C-20 carboxylic acid functional group followed by biological methylation at the C-11 phenol afforded 4. Oxidative cyclization of 1 to carnosol 5 followed by dihydroxylation at the isopropyl moiety afforded 6. Metabolites 4 and 6 are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of 4-6 using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging assay showed activities similar to that of mixed tocopherols and carnosic acid.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/2,2-diphenyl-1-picrylhydrazyl,
http://linkedlifedata.com/resource/pubmed/chemical/Antioxidants,
http://linkedlifedata.com/resource/pubmed/chemical/Biphenyl Compounds,
http://linkedlifedata.com/resource/pubmed/chemical/Diterpenes,
http://linkedlifedata.com/resource/pubmed/chemical/Diterpenes, Abietane,
http://linkedlifedata.com/resource/pubmed/chemical/Free Radical Scavengers,
http://linkedlifedata.com/resource/pubmed/chemical/Picrates,
http://linkedlifedata.com/resource/pubmed/chemical/Plant Extracts,
http://linkedlifedata.com/resource/pubmed/chemical/salvin
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pubmed:status |
MEDLINE
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pubmed:month |
Sep
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pubmed:issn |
0163-3864
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:volume |
65
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1266-9
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pubmed:dateRevised |
2009-11-19
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pubmed:meshHeading |
pubmed-meshheading:12350144-Antioxidants,
pubmed-meshheading:12350144-Biphenyl Compounds,
pubmed-meshheading:12350144-Cyclization,
pubmed-meshheading:12350144-Diterpenes,
pubmed-meshheading:12350144-Diterpenes, Abietane,
pubmed-meshheading:12350144-Free Radical Scavengers,
pubmed-meshheading:12350144-Mass Spectrometry,
pubmed-meshheading:12350144-Methylation,
pubmed-meshheading:12350144-Molecular Structure,
pubmed-meshheading:12350144-Nocardia,
pubmed-meshheading:12350144-Nuclear Magnetic Resonance, Biomolecular,
pubmed-meshheading:12350144-Oxidation-Reduction,
pubmed-meshheading:12350144-Picrates,
pubmed-meshheading:12350144-Plant Extracts,
pubmed-meshheading:12350144-Rosmarinus,
pubmed-meshheading:12350144-Structure-Activity Relationship
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pubmed:year |
2002
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pubmed:articleTitle |
Oxidation, reduction, and methylation of carnosic acid by Nocardia.
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pubmed:affiliation |
Center for Biocatalysis and Bioprocessing, Division of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City 52242, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.
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