Formation of Decatrienones with a Pineapple-like Aroma from 1-¹³C-Acetate by Cell Cultures of the Birch Polypore, Fomitopsis betulina

Abstract

During submerged cultivation, the edible basidiomycete Fomitopsis betulina (previously Piptoporus betulinus) developed a fruity odor, strongly reminding of pineapple. Olfactometric analysis showed that this impression was mainly caused by the two (5E/Z,7E,9)-decatrien-2-ones. At the time of maximum concentration on the 5th day, the (5E/5Z)-ratio was 94:6. Three hypotheses were experimentally examined to shed light onto the genesis of the uncommon volatiles: first, an indirect effect of agro-industrial side-streams, such as cabbage cuttings, supporting good growth; second, an unsaturated odd-numbered fatty acid precursor; and third, a polyketide-like pathway. In the presence of 1-13C- or 2-13C-acetate up to five acetates were incorporated into the molecular ions of the C10-body. Addition of 1-13C-pyruvate or 1-13C-lactate did not confirm an odd-numbered starter of the polyketide chain. None of the methylketones was found in pineapple or any other food before.

Improved Foods Using Enzymes from Basidiomycetes

“…Likewise unusual were dodec-11-enoic acid and di-and tri-unsaturated C16 isomer fatty acids in the lipids of Flammulina velutipes [112]. An excellent proof of the enormous synthetic potential of basidiomycetes was the identification of the (5E/Z,7E,9)-decatrien-2-ones in submerged, cultured Fomitopsis betulina (Figure 5b) [110,111]. The (5Z)-isomer possessed a strong pineapple flavour and belongs to the most potent flavour compounds known.…”

“…The combined action of a DyP and a laccase from Funalia trogii resulted in a complete conversion of (+)-valencene within 24 h (Figure 5a). An excellent proof of the enormous synthetic potential of basidiomycetes was the identification of the (5E/Z,7E,9)-decatrien-2-ones in submerged, cultured Fomitopsis betulina (Figure 5b) [110,111]. The (5Z)-isomer possessed a strong pineapple flavour and belongs to the most potent flavour compounds known.…”

Agro-Industrial Residues Used as Substrates for the Production of Bioaroma Compounds with Basidiomycetes: A Comprehensive Review

“…Thus, the fungal strain was able to biotransform food by-products into pleasant mixtures of complex flavors [12]. Grosse et al [116] used cabbage cuttings as a substrate in a fermentation medium submerged with the edible basidiomycete Fomitopsis betulina. They reported that the fermented product presented a fruity odor, strongly reminiscent of pineapple.…”

“…They reported that the fermented product presented a fruity odor, strongly reminiscent of pineapple. The olfactory analysis showed that this impression was mainly caused by the two (5E/Z,7E,9)-decatrien-2-one compounds [116,121].…”

Biogenesis of spiroketals by submerged cultured basidiomycete Trametes hirsuta

“…Main cultures were extracted by sequential stir bar sorptive extraction (SBSE) using Twisters (10 mm × 0.5 mm, Gerstel, Mülheim, Germany) coated with polydimethylsiloxane (PDMS) as described elsewhere (Grosse et al 2020;Sampedro et al 2009). In brief, 5 mL of the respective broth were extracted for 1 h at room temperature.…”