Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 1217-1220 |
| Seitenumfang | 4 |
| Fachzeitschrift | Natural product communications |
| Jahrgang | 6 |
| Ausgabenummer | 9 |
| Publikationsstatus | Veröffentlicht - 1 Sept. 2011 |
Abstract
HRGC-MS, using split/splitless injection (230°C), showed that a dioxygenase from Pleurotus sapidus regio-selectively transformed (+)-car-3-ene to car-3-en-5-one as the major volatile product to minor amounts of the corresponding alcohol, and to some other volatiles. Thus, the reaction was assumed to be radical mediated and similar to the lipoxygenase catalyzed peroxidation of polyunsaturated fatty acids, but the expected car-3-ene-hydroperoxides were not detected. TLC of the reaction products, followed by hydroperoxide specific staining, visually indicated the presence of hydroperoxides. TLC spots were eluted and re-analyzed using cool on-column injection, but only tailing peaks showing a mixed mass spectrum of car-3-en-5-ol/one were obtained. An unequivocal identification of car-3-en-5-hydroperoxides was achieved only after using APCI+-LC-MS. Upon structural confirmation, the car-3-en-5-hydroperoxide was accumulated by preparative HPLC, re-injected cool on-column, and the continuing degradation of the hydroperoxide to monoterpene ketone and alcohol during chromatography was verified. It was concluded that terpene hydroperoxides may occur in essential oils more frequently than anticipated, but are not recognized due to the principal blindness of capillary gas chromatography techniques and UV/vis LC-detectors.
ASJC Scopus Sachgebiete
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Pharmakologie
- Agrar- und Biowissenschaften (insg.)
- Pflanzenkunde
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Wirkstoffforschung
- Medizin (insg.)
- Ergänzende und alternative Medizin
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in: Natural product communications, Jahrgang 6, Nr. 9, 01.09.2011, S. 1217-1220.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Analysis of Car-3-en-5-hydroperoxide
AU - Lehnert, Nicole
AU - Krings, Ulrich
AU - Berger, Ralf G.
PY - 2011/9/1
Y1 - 2011/9/1
N2 - HRGC-MS, using split/splitless injection (230°C), showed that a dioxygenase from Pleurotus sapidus regio-selectively transformed (+)-car-3-ene to car-3-en-5-one as the major volatile product to minor amounts of the corresponding alcohol, and to some other volatiles. Thus, the reaction was assumed to be radical mediated and similar to the lipoxygenase catalyzed peroxidation of polyunsaturated fatty acids, but the expected car-3-ene-hydroperoxides were not detected. TLC of the reaction products, followed by hydroperoxide specific staining, visually indicated the presence of hydroperoxides. TLC spots were eluted and re-analyzed using cool on-column injection, but only tailing peaks showing a mixed mass spectrum of car-3-en-5-ol/one were obtained. An unequivocal identification of car-3-en-5-hydroperoxides was achieved only after using APCI+-LC-MS. Upon structural confirmation, the car-3-en-5-hydroperoxide was accumulated by preparative HPLC, re-injected cool on-column, and the continuing degradation of the hydroperoxide to monoterpene ketone and alcohol during chromatography was verified. It was concluded that terpene hydroperoxides may occur in essential oils more frequently than anticipated, but are not recognized due to the principal blindness of capillary gas chromatography techniques and UV/vis LC-detectors.
AB - HRGC-MS, using split/splitless injection (230°C), showed that a dioxygenase from Pleurotus sapidus regio-selectively transformed (+)-car-3-ene to car-3-en-5-one as the major volatile product to minor amounts of the corresponding alcohol, and to some other volatiles. Thus, the reaction was assumed to be radical mediated and similar to the lipoxygenase catalyzed peroxidation of polyunsaturated fatty acids, but the expected car-3-ene-hydroperoxides were not detected. TLC of the reaction products, followed by hydroperoxide specific staining, visually indicated the presence of hydroperoxides. TLC spots were eluted and re-analyzed using cool on-column injection, but only tailing peaks showing a mixed mass spectrum of car-3-en-5-ol/one were obtained. An unequivocal identification of car-3-en-5-hydroperoxides was achieved only after using APCI+-LC-MS. Upon structural confirmation, the car-3-en-5-hydroperoxide was accumulated by preparative HPLC, re-injected cool on-column, and the continuing degradation of the hydroperoxide to monoterpene ketone and alcohol during chromatography was verified. It was concluded that terpene hydroperoxides may occur in essential oils more frequently than anticipated, but are not recognized due to the principal blindness of capillary gas chromatography techniques and UV/vis LC-detectors.
KW - Bioconversion
KW - car-3-en-5-hydroperoxide
KW - car-3-en-5-one
KW - Pleurotus sapidus
UR - http://www.scopus.com/inward/record.url?scp=80155184116&partnerID=8YFLogxK
U2 - 10.1177/1934578x1100600901
DO - 10.1177/1934578x1100600901
M3 - Article
C2 - 21941881
AN - SCOPUS:80155184116
VL - 6
SP - 1217
EP - 1220
JO - Natural product communications
JF - Natural product communications
SN - 1934-578X
IS - 9
ER -