Honaucins A-C, Potent Inhibitors of Inflammation and Bacterial Quorum Sensing: Synthetic Derivatives and Structure-Activity Relationships

Title
Honaucins A-C, Potent Inhibitors of Inflammation and Bacterial Quorum Sensing: Synthetic Derivatives and Structure-Activity Relationships
Author(s)
최혁재Samantha J. Mascuch[Samantha J. Mascuch]Francisco A. Villa[Francisco A. Villa]Tara Byrum[Tara Byrum]Margaret E. Teasdale[Margaret E. Teasdale]Jennifer E. Smith[Jennifer E. Smith]Linda B. Preskitt[Linda B. Preskitt]David C. Rowley[David C. Rowley]Lena Gerwick[Lena Gerwick]William H. Gerwick[William H. Gerwick]
Keywords
NF-KAPPA-B; VIBRIO-HARVEYI; SECONDARY METABOLITES; NATURAL-PRODUCTS; GENE-EXPRESSION; CHEMISTRY; COMMUNICATION; TRANSCRIPTION; MODULATION; RECEPTORS
Issue Date
201205
Publisher
CELL PRESS
Citation
CHEMISTRY & BIOLOGY, v.19, no.5, pp.589 - 598
Abstract
Honaucins A-C were isolated from the cyanobacterium Leptolyngbya crossbyana which was found overgrowing corals on the Hawaiian coast. Honaucin A consists of (S)-3-hydroxy-gamma-butyrolactone and 4-chlorocrotonic acid, which are connected via an ester linkage. Honaucin A and its two natural analogs exhibit potent inhibition of both bioluminescence, a quorum-sensing-dependent phenotype, in Vibrio harveyi BB120 and lipopolysaccharide-stimulated nitric oxide production in the murine macrophage cell line RAW264.7. The decrease in nitric oxide production was accompanied by a decrease in the transcripts of several proinflammatory cytokines, most dramatically interleukin-1 beta. Synthesis of honaucin A, as well as a number of analogs, and subsequent evaluation in anti-inflammation and quorum-sensing inhibition bioassays revealed the essential structural features for activity in this chemical class and provided analogs with greater potency in both assays.
URI
http://hdl.handle.net/YU.REPOSITORY/28402http://dx.doi.org/10.1016/j.chembiol.2012.03.014
ISSN
1074-5521
Appears in Collections:
약학대학 > 약학부 > Articles
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