Lukasz M. Kutrzeba

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A search for biosynthetic precursors of salvinorin A (1) led to the isolation of a new neoclerodane diterpenoid hemiacetal mixture, salvinorins J (2), from the chloroform extract of Salvia divinorum. A leaf surface extraction method was used on S. divinorum, affording a chlorophyll-free extract containing predominantly neoclerodane diterpenoids, including(More)
The complete assignments of the (1)H and (13)C NMR spectra of the hallucinogenic neoclerodane diterpenoid salvinorin A were determined in three different NMR solvents using HSQC, HMBC and COSY. Solvent systems are described that allow the resolution of all (1)H signals. Virtual coupling was observed for the protons at C-2, C-3 and C-4 in the 600 MHz (1)H(More)
Extraction of fresh Salvia divinorum leaves afforded salvinorins E and D as potential biosynthesis precursors of salvinorin A, a major metabolite and a potent hallucinogen. Attempts at HPLC purification of salvinorin E (2) with acetonitrile as a solvent revealed an equilibrium with its regioisomer, salvinorin D (3), in a 3:5 ratio. The presence of both(More)
The hallucinogenic plant Salvia divinorum has been used for medical treatments of gastrointestinal disorders. Here, we evaluated the effect of a standardized extract from the leaves of Salvia divinorum (SDE) and of its active ingredient salvinorin A on motility in vivo, both in physiological states and during croton oil-induced intestinal inflammation. SDE(More)
Salvinorin A, a neoclerodane diterpenoid, isolated from the Mexican hallucinogenic plant Salvia divinorum, is a potent kappa-opioid receptor agonist. Its biosynthetic route was studied by NMR and HR-ESI-MS analysis of the products of the incorporation of [1-(13)C]-glucose, [Me-(13)C]-methionine, and [1-(13)C;3,4-(2)H2]-1-deoxy-D-xylulose into its structure.(More)
The asymmetric unit of the title compound, C(22)H(26)O(8), contains two crystallographically independent mol-ecules with closely comparable conformations (r.m.s. overlay = 0.54 Å for 30 non-H atoms). All six-membered rings display chair conformations, with a slight distortion for the lactone ring. The mol-ecules are connected by O-H⋯O hydrogen bonds into(More)
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