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

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dc.contributor.authorYilmaz, ANIL
dc.contributor.authorCrowley, Rachel Saylor
dc.contributor.authorSherwood, Alexander M.
dc.contributor.authorPrisinzano, Thomas E.
dc.contributor.institutionauthorYILMAZ, ANIL
dc.date.accessioned2019-10-05T22:13:26Z
dc.date.available2019-10-05T22:13:26Z
dc.date.issued2017-07-01
dc.description.abstractColumbin (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.
dc.identifier
dc.identifier.citationYilmaz A., Crowley R. S. , Sherwood A. M. , Prisinzano T. E. , -Semisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene-, JOURNAL OF NATURAL PRODUCTS, cilt.80, ss.2094-2100, 2017
dc.identifier.urihttps://hdl.handle.net/20.500.12645/9148
dc.language.isoen
dc.titleSemisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene
dc.typeArticle
dspace.entity.typePublication
local.article.journalnameTürkiye Klinikleri
local.avesis.ide3a55a5d-f736-4ab1-a721-1590c3508db6
local.avesis.response9024
local.publication.goal03 - Sağlık ve Kaliteli Yaşam
relation.isAuthorOfPublication9c5ef152-9387-4153-86b3-556fc729d785
relation.isAuthorOfPublication.latestForDiscovery9c5ef152-9387-4153-86b3-556fc729d785
relation.isGoalOfPublication9c198c48-b603-4e2f-8366-04edcfc1224c
relation.isGoalOfPublication.latestForDiscovery9c198c48-b603-4e2f-8366-04edcfc1224c
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