TY - JOUR
T1 - Oxidation products of hyperforin from Hypericum perforatum
AU - Trifunović, Snežana
AU - Vajs, Vlatka
AU - Macura, Slobodan
AU - Juranić, Nenad
AU - Djarmati, Zoltan
AU - Jankov, Ratko
AU - Milosavljević, Slobodan
N1 - Funding Information:
The authors thank the Ministry for Science and Technology, Republic of Serbia, for financial support. We are grateful to Mrs Dušanka Runjajić-Antić (Institute for Medicinal Plant Research, Dr Josif Pančitć, Belgrade) for the collection and identification of plant material. We are indebted to Dr Gordana Gojgić, Institute for Chemistry, Technology and Metallurgy, Belgrade for performing of bioassays.
PY - 1998/11/5
Y1 - 1998/11/5
N2 - 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-3,10β-bis(3-methyl-2-butenyl)-11β-methyl-11α-(4- methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0 4,8 ]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C 35 H 52 O 5 ), contained a 1-methyl-1-hydroxyethyl group in the 6β- position, whereas the other compound (a hemiacetal, C 32 H 46 O 5 ), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6α- and 6β-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.
AB - 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-3,10β-bis(3-methyl-2-butenyl)-11β-methyl-11α-(4- methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0 4,8 ]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C 35 H 52 O 5 ), contained a 1-methyl-1-hydroxyethyl group in the 6β- position, whereas the other compound (a hemiacetal, C 32 H 46 O 5 ), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6α- and 6β-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.
KW - Hypericaceae
KW - Hypericum perforatum
KW - Oxidized hyperforins
KW - Supercritical CO fractionation
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U2 - 10.1016/S0031-9422(97)00903-5
DO - 10.1016/S0031-9422(97)00903-5
M3 - Article
C2 - 9842729
AN - SCOPUS:0032487784
SN - 0031-9422
VL - 49
SP - 1305
EP - 1310
JO - Phytochemistry
JF - Phytochemistry
IS - 5
ER -