Structural Characterization of Genuine (-)-Pipermethystine,(-)-Epoxypipermethystine,(+)-Dihydromethysticin and Yangonin from the Kava Plant ( Piper methysticum )
Free accessResearch articleFirst published online August, 2008
Structural Characterization of Genuine (-)-Pipermethystine,(-)-Epoxypipermethystine,(+)-Dihydromethysticin and Yangonin from the Kava Plant ( Piper methysticum )
Two alkaloids, (-)-pipermethystine and (-)-epoxypipermethystine, and two lactones, (+)-dihydromethysticin and yangonin, were isolated from the kava plant (Piper methysticum) and crystallographically authenticated.
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Additional details on the isolation and crystallographic data are deposited as Supporting Information.
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The C6a–C7a/C6′–C7′, C7a–C8a/C7′–C8′ and C8a–C9a/C8′–C9′ pairs of bond distances were restrained to 1.50±0.01 Å and the C6a·C··8a/C6′···C8′ and C7a···C9a/C7′···C9′ interactions to 2.45±0.01 Å. The O1a–C6a and O1a–C6′ bond distances were restrained to within 0.01 Å of each other, as were the C4a–C6a/C4a–C6′, C6a–C7a/C6′–C7′, O4a–C11a/O4a–C11′ and O5a–C12a/O5a–C12′ pairs. Additionally, the temperature factors of the primed atoms were set to those of the unprimed (b) atoms; the vibrations of the C6a, C7a and C8a atoms were restrained to be nearly isotropic. The C8a, C9a, C10a, C11a, C12a, C13a and C14a atoms were restrained to lie in an almost flat plane, as were the primed C8′, C9′, C10′, C11′, C12′, C13′ and C14′ atoms. The phenyl/phenylene rings were refined as rigid hexagons on 1.39 Å sides; hydrogen atoms were included in the refinement in the riding model approximation.
