Oxidation products of hyperforin from Hypericum perforatum.
The isolation of two oxidation products of hyperforin from the aerial parts of Hypericum perforatum and their structure determination by means of 2D NMR methods is reported. The products had the same 1-(2-methyl-1-oxopropyl)-2,12-dioxo-3,10 beta-bis(3-methyl-2-butenyl)-11 beta-methyl-11 alpha-(4-methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0(4,8)]-3-dodec ene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C35H52O5), contained a 1-methyl-l-hydroxyethyl group in the 6 beta-position, whereas the other compound (a hemiacetal, C32H46O5), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6 alpha- and 6 beta-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.
Trifunović
S
S
Faculty of Chemistry, University of Belgrade, Yugoslavia.
Vajs
V
V
Macura
S
S
Juranić
N
N
Djarmati
Z
Z
Jankov
R
R
Milosavljević
S
S
D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds; D020448:Ericales / Q000737:chemistry* / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D010696:Phloroglucinol / Q000031:analogs & derivatives; D010936:Plant Extracts / Q000302:isolation & purification* / Q000378:metabolism* / Q000494:pharmacology; D013729:Terpenes / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D001643:Bridged Bicyclo Compounds; D010936:Plant Extracts; D013729:Terpenes; D010696:Phloroglucinol; C001654:hyperforin