Structural characterization of genuine (-)-pipermethystine, (-)-epoxypipermethystine, (+)-dihydromethysticin and yangonin from the kava plant (Piper methysticum)

Natural Product Communications

Volumn 3, Issue 8, 2008, Pages 1333-1336

  Naumov, Panče ^a,b   Dragull, Klaus ^c   Yoshioka, Masahiro ^c,d   Tang, Chung Shih ^c   Ng, Seik Weng ^e  

^a NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^b SS CYRIL AND METHODIUS UNIVERSITY   (Macedonia)

^c UNIVERSITY OF HAWAII AT MANOA   (United States)

^d UNIVERSITY OF TSUKUBA   (Japan)

^e UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Dihydromethysticin; Epoxypipermethystine; Kava alkaloids; Kava plant; Kavalactones; Pipermethystine; Yangonin

Indexed keywords

ALKALOID DERIVATIVE; DIHYDROMETHYSTICIN; EPOXYPIPERMETHYSTINE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; YANGONIN;

ARTICLE; CRYSTALLOGRAPHY; DRUG ISOLATION; NONHUMAN; PIPER METHYSTICUM; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

PIPER METHYSTICUM;

EID: 77954019767     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0800300819     Document Type: Article

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29. 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⋯C8a/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.