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Semisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene

Yilmaz, Anil; Crowley, Rachel Saylor; Sherwood, Alexander M.; Prisinzano, Thomas E.


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/47617</identifier>
  <creators>
    <creator>
      <creatorName>Yilmaz, Anil</creatorName>
      <givenName>Anil</givenName>
      <familyName>Yilmaz</familyName>
      <affiliation>Istanbul Tech Univ, Fac Arts &amp; Sci, Dept Chem, TR-34469 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Crowley, Rachel Saylor</creatorName>
      <givenName>Rachel Saylor</givenName>
      <familyName>Crowley</familyName>
      <affiliation>Univ Kansas, Sch Pharm, Dept Med Chem, Lawrence, KS 66045 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Sherwood, Alexander M.</creatorName>
      <givenName>Alexander M.</givenName>
      <familyName>Sherwood</familyName>
      <affiliation>Univ Kansas, Sch Pharm, Dept Med Chem, Lawrence, KS 66045 USA</affiliation>
    </creator>
    <creator>
      <creatorName>Prisinzano, Thomas E.</creatorName>
      <givenName>Thomas E.</givenName>
      <familyName>Prisinzano</familyName>
      <affiliation>Univ Kansas, Sch Pharm, Dept Med Chem, Lawrence, KS 66045 USA</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Semisynthesis And Kappa-Opioid Receptor Activity Of Derivatives Of Columbin, A Furanolactone Diterpene</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2017</publicationYear>
  <dates>
    <date dateType="Issued">2017-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/47617</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1021/acs.jnatprod.7b00327</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">Columbin (1) is a furanolactone diterpene isolated from the roots of Jateorhiza and Tinospora species. These species generally grow in Asia and Africa and have been used in folk medicine for their apparent analgesic and antipyretic activities. Columbin (1) is of particular interest due to its structural similarity to the known kappa-opioid receptor (KOR) agonist salvinorin A. Given that the KOR is of interest in the study of many serious diseases, such as anxiety, depression, and drug addiction, obtaining natural or semisynthetic molecules with KOR activity recently has gained much interest. For this reason, in the present study, derivatives of 1 were designed and synthesized using known structure-activity relationships of salvinorin A at KORs. The structures of the columbin analogues prepared were elucidated by NMR spectroscopy and mass spectroscopy, and their KOR activity was investigated in vitro by inhibition of forskolin-induced CAMP accumulation. Slight improvements in KOR activity were observed in columbin derivatives over their parent compound. However, despite the structural similarities to salvinorin A, neither columbin (1) nor its derivatives were potent KOR ligands. This work represents not only the first evaluation of columbin (1) at the KOR but also one of the first works to explore synthetic strategies that are tolerated on the columbin core.</description>
  </descriptions>
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