Concise syntheses and anti-inflammatory effects of isocorniculatolide B and corniculatolide B and C
DC Field | Value | Language |
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dc.contributor.author | Kim, Taewoo | - |
dc.contributor.author | Kwon, Hyuk | - |
dc.contributor.author | Lee, Da-Young | - |
dc.contributor.author | Kim, Dong-Jun | - |
dc.contributor.author | Jeon, Yoonsu | - |
dc.contributor.author | Shin, Hyeyoung | - |
dc.contributor.author | Kim, Hyun Su | - |
dc.contributor.author | Hur, Joonseong | - |
dc.contributor.author | Lim, Changjin | - |
dc.contributor.author | Kim, Eun-Hee | - |
dc.contributor.author | Shin, Dongyun | - |
dc.contributor.author | Kim, Seok-Ho | - |
dc.date.accessioned | 2021-11-09T11:40:25Z | - |
dc.date.available | 2021-11-09T11:40:25Z | - |
dc.date.created | 2021-10-18 | - |
dc.date.issued | 2021-11 | - |
dc.identifier.issn | 0045-2068 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/82629 | - |
dc.description.abstract | The first total syntheses of isocorniculatolide B, corniculatolide B, and corniculatolide C, consisting of isomeric corniculatolide skeletons, have been accomplished in a divergent manner. The key features of the synthesis involve the construction of diaryl ether linkages by nucleophilic aromatic substitution, installation of a C14-substituted alkyl side chain via a sequence of Baeyer-Villiger reaction and Claisen rearrangement, and efficient construction of corniculatolide and isocorniculatolide frameworks, including 17-membered (exterior) macrolactone skeletons from a versatile diaryl ether intermediate by Mitsunobu macrolactonization. Moreover, we prepared the structural congeners of isomeric corniculatolides via diverted total synthesis approach including desmethyl analogues and related dimeric macrolides. The anti-inflammatory activities of the synthesized natural products, analogues and synthetic intermediates were also investigated. In particular, corniculatolide B significantly inhibited the protein expression of COX-2 and the mRNA expressions of TNF-α, IL-1β and IL-6 by inhibiting of NF-κB signaling in intestinal epithelial cells induced by lipopolysaccharide treatment. It also significantly inhibited the promoter activity and the phosphorylation of subunits p50 and p65 of NF-κB to the same extent as Bay 11-7082, a potent IκB kinase inhibitor. These results suggest that corniculatolide B might have therapeutic potential in inflammatory bowel disease via NF-κB signaling pathway. © 2021 Elsevier Inc. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | Academic Press Inc. | - |
dc.relation.isPartOf | Bioorganic Chemistry | - |
dc.title | Concise syntheses and anti-inflammatory effects of isocorniculatolide B and corniculatolide B and C | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.description.journalClass | 1 | - |
dc.identifier.wosid | 000711455000012 | - |
dc.identifier.doi | 10.1016/j.bioorg.2021.105398 | - |
dc.identifier.bibliographicCitation | Bioorganic Chemistry, v.116 | - |
dc.description.isOpenAccess | N | - |
dc.identifier.scopusid | 2-s2.0-85116604408 | - |
dc.citation.title | Bioorganic Chemistry | - |
dc.citation.volume | 116 | - |
dc.contributor.affiliatedAuthor | Hur, Joonseong | - |
dc.contributor.affiliatedAuthor | Shin, Dongyun | - |
dc.type.docType | Article | - |
dc.subject.keywordAuthor | Anti-inflammatory activity | - |
dc.subject.keywordAuthor | Corniculatolide B | - |
dc.subject.keywordAuthor | IBD | - |
dc.subject.keywordAuthor | Isomeric corniculatolides | - |
dc.subject.keywordAuthor | NF-κB | - |
dc.subject.keywordAuthor | Total synthesis | - |
dc.subject.keywordPlus | NF-KAPPA-B | - |
dc.subject.keywordPlus | MANGROVE | - |
dc.subject.keywordPlus | LIMONOIDS | - |
dc.subject.keywordPlus | CANCER | - |
dc.relation.journalResearchArea | Biochemistry & Molecular Biology | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Biochemistry & Molecular Biology | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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