Details
| Original language | English |
|---|---|
| Pages (from-to) | 2855-2860 |
| Number of pages | 6 |
| Journal | Bioresource technology |
| Volume | 100 |
| Issue number | 11 |
| Publication status | Published - 14 Feb 2009 |
Abstract
Enzymatic synthesis of furanoterpenoids from β-myrcene and related monoterpenes was observed using a solubilised enzyme fraction of mycelium lyophilisates of several Pleurotus species. The initial enzymatic step, the incorporation of molecular oxygen into the conjugated 1,3-diene moiety, was similar to a 2 + 4 cycloaddition of 1,3-dienes with dienophilic 1O2, and was followed by a non-catalysed degradation sequence leading to the furans. The cyclic peroxides 3,6-dihydro-4-(2-(3,3-dimethyloxiran-2-yl)ethyl)-1,2-dioxine and 5-(3,6-dihydro-1,2-dioxin-4-yl)-2-methylpentan-2-ol were identified as key intermediates. Biotransformation of β-myrcene in 18O-labelled HEPES-buffer did not yield a detectable label in perillene, so a water addition to 3,10-epoxy-β-myrcenes as an alternative was ruled out. The pathway suggested presents a substantiated biogenetic scheme for the formation of monoterpenoid furans and opens biotechnological access to valuable natural flavour compounds, such as perillene and rosefurane. Only one metabolite, identified as the new natural compound 6-methyl-2-methylene-hept-5-enal, carried the 18O-label. The enzymatic formation of this compound through a 1,2-endoperoxide (3-(5-methyl-1-methylene-hex-4-enyl)-[1,2]-dioxetane) is suggested. The label may simply result from a chemical oxygen exchange between the carbonyl group and the 18O-labelled water.
Keywords
- β-Myrcene, Endoperoxide, Perillene, Pleurotus sapidus, Rose furane
ASJC Scopus subject areas
- Chemical Engineering(all)
- Bioengineering
- Environmental Science(all)
- Environmental Engineering
- Energy(all)
- Renewable Energy, Sustainability and the Environment
- Environmental Science(all)
- Waste Management and Disposal
Sustainable Development Goals
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In: Bioresource technology, Vol. 100, No. 11, 14.02.2009, p. 2855-2860.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Pleurotus species convert monoterpenes to furanoterpenoids through 1,4-endoperoxides
AU - Krügener, Sven
AU - Schaper, Carmen
AU - Krings, Ulrich
AU - Berger, Ralf G.
N1 - Funding information: This work was financed by the Deutsche Forschungsgemeinschaft (DFG KR 2958/1-1). We thank H. Ziegler for providing reference chemicals, F. Robic for her valuable assistance and D. Albert, Department of Organic Chemistry, Leibniz University of Hannover, for his support in NMR analysis.
PY - 2009/2/14
Y1 - 2009/2/14
N2 - Enzymatic synthesis of furanoterpenoids from β-myrcene and related monoterpenes was observed using a solubilised enzyme fraction of mycelium lyophilisates of several Pleurotus species. The initial enzymatic step, the incorporation of molecular oxygen into the conjugated 1,3-diene moiety, was similar to a 2 + 4 cycloaddition of 1,3-dienes with dienophilic 1O2, and was followed by a non-catalysed degradation sequence leading to the furans. The cyclic peroxides 3,6-dihydro-4-(2-(3,3-dimethyloxiran-2-yl)ethyl)-1,2-dioxine and 5-(3,6-dihydro-1,2-dioxin-4-yl)-2-methylpentan-2-ol were identified as key intermediates. Biotransformation of β-myrcene in 18O-labelled HEPES-buffer did not yield a detectable label in perillene, so a water addition to 3,10-epoxy-β-myrcenes as an alternative was ruled out. The pathway suggested presents a substantiated biogenetic scheme for the formation of monoterpenoid furans and opens biotechnological access to valuable natural flavour compounds, such as perillene and rosefurane. Only one metabolite, identified as the new natural compound 6-methyl-2-methylene-hept-5-enal, carried the 18O-label. The enzymatic formation of this compound through a 1,2-endoperoxide (3-(5-methyl-1-methylene-hex-4-enyl)-[1,2]-dioxetane) is suggested. The label may simply result from a chemical oxygen exchange between the carbonyl group and the 18O-labelled water.
AB - Enzymatic synthesis of furanoterpenoids from β-myrcene and related monoterpenes was observed using a solubilised enzyme fraction of mycelium lyophilisates of several Pleurotus species. The initial enzymatic step, the incorporation of molecular oxygen into the conjugated 1,3-diene moiety, was similar to a 2 + 4 cycloaddition of 1,3-dienes with dienophilic 1O2, and was followed by a non-catalysed degradation sequence leading to the furans. The cyclic peroxides 3,6-dihydro-4-(2-(3,3-dimethyloxiran-2-yl)ethyl)-1,2-dioxine and 5-(3,6-dihydro-1,2-dioxin-4-yl)-2-methylpentan-2-ol were identified as key intermediates. Biotransformation of β-myrcene in 18O-labelled HEPES-buffer did not yield a detectable label in perillene, so a water addition to 3,10-epoxy-β-myrcenes as an alternative was ruled out. The pathway suggested presents a substantiated biogenetic scheme for the formation of monoterpenoid furans and opens biotechnological access to valuable natural flavour compounds, such as perillene and rosefurane. Only one metabolite, identified as the new natural compound 6-methyl-2-methylene-hept-5-enal, carried the 18O-label. The enzymatic formation of this compound through a 1,2-endoperoxide (3-(5-methyl-1-methylene-hex-4-enyl)-[1,2]-dioxetane) is suggested. The label may simply result from a chemical oxygen exchange between the carbonyl group and the 18O-labelled water.
KW - β-Myrcene
KW - Endoperoxide
KW - Perillene
KW - Pleurotus sapidus
KW - Rose furane
UR - http://www.scopus.com/inward/record.url?scp=61549090583&partnerID=8YFLogxK
U2 - 10.1016/j.biortech.2009.01.001
DO - 10.1016/j.biortech.2009.01.001
M3 - Article
C2 - 19223179
AN - SCOPUS:61549090583
VL - 100
SP - 2855
EP - 2860
JO - Bioresource technology
JF - Bioresource technology
SN - 0960-8524
IS - 11
ER -