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.
TY - JOUR
AU - Trifunović, Snežana
AU - Vajs, Vlatka
AU - Macura, Slobodan
AU - Juranić, Nenad
AU - Djarmati, Z
AU - Jankov, Ratko
AU - Milosavljević, Slobodan
PY - 1998
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/2807
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.
PB - Elsevier Ltd
T2 - Phytochemistry
T1 - Oxidation products of hyperforin from Hypericum perforatum
VL - 49
IS - 5
SP - 1305
EP - 1310
DO - 10.1016/S0031-9422(97)00903-5
ER -
@article{
author = "Trifunović, Snežana and Vajs, Vlatka and Macura, Slobodan and Juranić, Nenad and Djarmati, Z and Jankov, Ratko and Milosavljević, Slobodan",
year = "1998",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2807",
abstract = "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.",
publisher = "Elsevier Ltd",
journal = "Phytochemistry",
title = "Oxidation products of hyperforin from Hypericum perforatum",
volume = "49",
number = "5",
pages = "1305-1310",
doi = "10.1016/S0031-9422(97)00903-5"
}
Trifunović, S., Vajs, V., Macura, S., Juranić, N., Djarmati, Z., Jankov, R.,& Milosavljević, S. (1998). Oxidation products of hyperforin from Hypericum perforatum.
Phytochemistry
Elsevier Ltd., 49(5), 1305-1310.
https://doi.org/10.1016/S0031-9422(97)00903-5
Trifunović S, Vajs V, Macura S, Juranić N, Djarmati Z, Jankov R, Milosavljević S. Oxidation products of hyperforin from Hypericum perforatum. Phytochemistry. 1998;49(5):1305-1310
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