Details
| Originalsprache | Englisch |
|---|---|
| Aufsatznummer | 58 |
| Seitenumfang | 10 |
| Fachzeitschrift | Mycological progress |
| Jahrgang | 21 |
| Ausgabenummer | 6 |
| Frühes Online-Datum | 27 Mai 2022 |
| Publikationsstatus | Veröffentlicht - Juni 2022 |
Abstract
Volatile spiroketals are well-documented semiochemicals secreted by beetles and wasps for the intra- and interspecies communication. Its use in insect traps and as natural herbicide makes them of commercial interest. Besides insects, fungi are well-known producers, but the fungal biogenesis of spiroketals has remained speculative. Product formation along fatty acid degradation based on non-labeled feeding experiments was assumed. Thus, the observed occurrence of conophthorin and (E)- and (Z)-chalcograns in submerged cultures of the basidiomycete Trametes hirsuta prompted a precursor study aiming at a more detailed insight into their formation. Supplementation of (9Z,12 Z)-octadecadienoic (linoleic) acid resulted in elevated product yields and the identification of a fourth spiroketal, 2,8-dimethyl-1,7-dioxaspiro[5.5]-undecane. However, no intermediates of fatty acid degradation suitable as spiroketal precursors were identified. In addition, the hyphae lacked lipoxygenase activity, which was formerly supposed to be mandatory for spiroketal formation. Supplementation of 1-/2-13C acetate showed incorporation of the label into chalcogran. Therefore, a formation along the polyketide pathway analogous to insects was concluded. Graphical abstract: [Figure not available: see fulltext.]
ASJC Scopus Sachgebiete
- Agrar- und Biowissenschaften (insg.)
- Ökologie, Evolution, Verhaltenswissenschaften und Systematik
- Agrar- und Biowissenschaften (insg.)
- Agrar- und Biowissenschaften (sonstige)
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in: Mycological progress, Jahrgang 21, Nr. 6, 58, 06.2022.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Biogenesis of spiroketals by submerged cultured basidiomycete Trametes hirsuta
AU - Grosse, Miriam
AU - Heuser, Verena
AU - Ersoy, Franziska
AU - Berger, Ralf G.
AU - Krings, Ulrich
N1 - Funding Information: Thanks go to Noreen E. Mahoney and Wai S. Gee (WRRC, ARS, Albany/CA, USA) for support with mass spectrometric data for the preliminary identification of the Conophthorin. Special thanks to Pia Bergmann for the graphical abstract.
PY - 2022/6
Y1 - 2022/6
N2 - Volatile spiroketals are well-documented semiochemicals secreted by beetles and wasps for the intra- and interspecies communication. Its use in insect traps and as natural herbicide makes them of commercial interest. Besides insects, fungi are well-known producers, but the fungal biogenesis of spiroketals has remained speculative. Product formation along fatty acid degradation based on non-labeled feeding experiments was assumed. Thus, the observed occurrence of conophthorin and (E)- and (Z)-chalcograns in submerged cultures of the basidiomycete Trametes hirsuta prompted a precursor study aiming at a more detailed insight into their formation. Supplementation of (9Z,12 Z)-octadecadienoic (linoleic) acid resulted in elevated product yields and the identification of a fourth spiroketal, 2,8-dimethyl-1,7-dioxaspiro[5.5]-undecane. However, no intermediates of fatty acid degradation suitable as spiroketal precursors were identified. In addition, the hyphae lacked lipoxygenase activity, which was formerly supposed to be mandatory for spiroketal formation. Supplementation of 1-/2-13C acetate showed incorporation of the label into chalcogran. Therefore, a formation along the polyketide pathway analogous to insects was concluded. Graphical abstract: [Figure not available: see fulltext.]
AB - Volatile spiroketals are well-documented semiochemicals secreted by beetles and wasps for the intra- and interspecies communication. Its use in insect traps and as natural herbicide makes them of commercial interest. Besides insects, fungi are well-known producers, but the fungal biogenesis of spiroketals has remained speculative. Product formation along fatty acid degradation based on non-labeled feeding experiments was assumed. Thus, the observed occurrence of conophthorin and (E)- and (Z)-chalcograns in submerged cultures of the basidiomycete Trametes hirsuta prompted a precursor study aiming at a more detailed insight into their formation. Supplementation of (9Z,12 Z)-octadecadienoic (linoleic) acid resulted in elevated product yields and the identification of a fourth spiroketal, 2,8-dimethyl-1,7-dioxaspiro[5.5]-undecane. However, no intermediates of fatty acid degradation suitable as spiroketal precursors were identified. In addition, the hyphae lacked lipoxygenase activity, which was formerly supposed to be mandatory for spiroketal formation. Supplementation of 1-/2-13C acetate showed incorporation of the label into chalcogran. Therefore, a formation along the polyketide pathway analogous to insects was concluded. Graphical abstract: [Figure not available: see fulltext.]
KW - Chalcogran
KW - Conophthorin
KW - Polyketide
KW - Spiroketals
KW - Trametes hirsuta
UR - http://www.scopus.com/inward/record.url?scp=85130681446&partnerID=8YFLogxK
U2 - 10.1007/s11557-022-01798-w
DO - 10.1007/s11557-022-01798-w
M3 - Article
AN - SCOPUS:85130681446
VL - 21
JO - Mycological progress
JF - Mycological progress
SN - 1617-416X
IS - 6
M1 - 58
ER -