Oxidation products of hyperforin from Hypericum perforatum
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1998
Authors
Trifunović, Snežana S.Vajs, Vlatka
Macura, S.
Juranić, N.
Djarmati, Z
Jankov, Ratko M.
Milosavljevic, S
Article (Published version)
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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-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C35H52O5), contained a 1-methyl-1-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. (C) 1998 Elsevier Science Ltd. All rights reserved.
Keywords:
Hypericum perforatum / Hypericaceae / supercritical CO2 fractionation / oxidized hyperforinsSource:
Phytochemistry, 1998, 49, 5, 1305-1310Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.1016/S0031-9422(97)00903-5
ISSN: 0031-9422
PubMed: 9842729
WoS: 000077125100024
Scopus: 2-s2.0-0032487784
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Trifunović, Snežana S. AU - Vajs, Vlatka AU - Macura, S. AU - Juranić, N. AU - Djarmati, Z AU - Jankov, Ratko M. AU - Milosavljevic, S PY - 1998 UR - https://cherry.chem.bg.ac.rs/handle/123456789/400 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-3,10 beta-bis(3-methyl-2-butenyl)-11 beta-methyl-11 alpha-(4-methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0(4.8)]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C35H52O5), contained a 1-methyl-1-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. (C) 1998 Elsevier Science Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford 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 S. and Vajs, Vlatka and Macura, S. and Juranić, N. and Djarmati, Z and Jankov, Ratko M. and Milosavljevic, S", year = "1998", 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-3,10 beta-bis(3-methyl-2-butenyl)-11 beta-methyl-11 alpha-(4-methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0(4.8)]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C35H52O5), contained a 1-methyl-1-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. (C) 1998 Elsevier Science Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", 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. S., Vajs, V., Macura, S., Juranić, N., Djarmati, Z., Jankov, R. M.,& Milosavljevic, S.. (1998). Oxidation products of hyperforin from Hypericum perforatum. in Phytochemistry Pergamon-Elsevier Science Ltd, Oxford., 49(5), 1305-1310. https://doi.org/10.1016/S0031-9422(97)00903-5
Trifunović SS, Vajs V, Macura S, Juranić N, Djarmati Z, Jankov RM, Milosavljevic S. Oxidation products of hyperforin from Hypericum perforatum. in Phytochemistry. 1998;49(5):1305-1310. doi:10.1016/S0031-9422(97)00903-5 .
Trifunović, Snežana S., Vajs, Vlatka, Macura, S., Juranić, N., Djarmati, Z, Jankov, Ratko M., Milosavljevic, S, "Oxidation products of hyperforin from Hypericum perforatum" in Phytochemistry, 49, no. 5 (1998):1305-1310, https://doi.org/10.1016/S0031-9422(97)00903-5 . .