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Oxidation products of hyperforin from Hypericum perforatum

Authorized Users Only
1998
Authors
Trifunović, Snežana
Vajs, Vlatka
Macura, Slobodan
Juranić, Nenad
Djarmati, Z
Jankov, Ratko
Milosavljević, Slobodan
Article (Published version)
,
Elsevier
Metadata
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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.
Keywords:
Hypericum perforatum / Hypericaceae / supercritical CO2 / fractionation / oxidized hyperforins
Source:
Phytochemistry, 1998, 49, 5, 1305-1310
Publisher:
  • Elsevier
Funding / projects:
  • Ministry for Science and Technology, Republic of Serbia

DOI: 10.1016/S0031-9422(97)00903-5

ISSN: 0031-9422

WoS: 000077125100024

Scopus: 2-s2.0-0032487784
[ Google Scholar ]
62
62
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2807
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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  - https://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
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",
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",
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. in Phytochemistry
Elsevier., 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. in Phytochemistry. 1998;49(5):1305-1310.
doi:10.1016/S0031-9422(97)00903-5 .
Trifunović, Snežana, Vajs, Vlatka, Macura, Slobodan, Juranić, Nenad, Djarmati, Z, Jankov, Ratko, Milosavljević, Slobodan, "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 . .

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