Phytochemical investigation of Salvia divinorum
Advisor: Zjawiony, Jordan K.School: The University of Mississippi
School Location: United States -- Mississippi
Keyword(s): Phytochemical, Salvinorin A, Kappa-opioid receptor
Source: DAI-B 66/09, p. 4826, Mar 2006
Source type: Dissertation
Subjects: Pharmacology
Publication Number: AAT 3190573
ISBN: 0542328372
Document URL: [url]http://ezproxy.library.wisc.edu/login?url=http://proquest.umi.com/pqdweb?did=1003853941&sid=1&Fmt=2&clientId=12286&RQT=309&VName=PQD[/url]
ProQuest document ID: 1003853941
Abstract (Summary)
The results of previous investigations found that salvinorin A is a unique hallucinogenic diterpenoid acting as a highly selective and potent κ-opioid receptor (KOR) agonist. A phytochemical investigation was conducted on Salvia divinorum in an effort to understand more fully the production and structure-activity relationship (SAR) of the major secondary metabolite, salvinorin A. The biosynthesis and nutrient effect on production of this psychoactive diterpenoid were probed using isotopic labeling techniques and hydroponics, respectively. The SAR study focused on C-2 derivatives comprised of alkyl, aromatic, and carbonate esters, as well as bioisosteric analogs of salvinorin A. The results of this investigation yielded an efficient method for hydrolyzing salvinorin A, established a crucial growth parameter for metabolite production, and produced several salvinorin A derivatives that had significant KOR affinity.
It was concluded that salvinorin A is not produced via the mevalonic acid pathway, and phosphorus availability can have a significant impact on yields of the parent compound. A C-2 acetate, as found in salvinorin A, was found to be the optimum functional group for KOR affinity but not essential for receptor recognition. The sulfur bioisoster, thioacetate-2-salvinorinyl, most closely resembled the KOR affinity of salvinorin A.
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