Abstract
AbstractVolatile 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
Funder
Gottfried Wilhelm Leibniz Universität Hannover
Publisher
Springer Science and Business Media LLC
Subject
Agricultural and Biological Sciences (miscellaneous),Ecology, Evolution, Behavior and Systematics
Cited by
1 articles.
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