Biogeneration and Biodegradation of Raspberry Ketone in the Fungus <i>Beauveria bassiana</i>

Fuganti, Claudio; Mendozza, Monica; Joulain, Daniel; Minut, Jose; Pedrocchi-Fantoni, Giuseppe; Piergianni, Valentino; Servi, Stefano De; Zucchi, Gioia

doi:10.1021/jf9508054

Cited by 20 publications

(9 citation statements)

References 7 publications

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“…Although product degradation may occur as a function of time ( Figure 4 ), by timing the product recovery correctly the yields of produced 3 remain rather high. Earlier it had been suggested that raspberry ketone is degraded into tyrosol in fungi ( Fuganti et al, 1996 ), but tyrosol was not detected in our cell culture samples.…”

Section: Discussioncontrasting

confidence: 63%

Bioconversion to Raspberry Ketone is Achieved by Several Non-related Plant Cell Cultures

et al. 2015

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Bioconversion, i.e., the use of biological systems to perform chemical changes in synthetic or natural compounds in mild conditions, is an attractive tool for the production of novel active or high-value compounds. Plant cells exhibit a vast biochemical potential, being able to transform a range of substances, including pharmaceutical ingredients and industrial by-products, via enzymatic processes. The use of plant cell cultures offers possibilities for contained and optimized production processes which can be applied in industrial scale. Raspberry ketone [4-(4-hydroxyphenyl)butan-2-one] is among the most interesting natural flavor compounds, due to its high demand and significant market value. The biosynthesis of this industrially relevant flavor compound is relatively well characterized, involving the condensation of 4-coumaryl-CoA and malonyl-CoA by Type III polyketide synthase to form a diketide, and the subsequent reduction catalyzed by an NADPH-dependent reductase. Raspberry ketone has been successfully produced by bioconversion using different hosts and precursors to establish more efficient and economical processes. In this work, we studied the effect of overexpressed RiZS1 in tobacco on precursor bioconversion to raspberry ketone. In addition, various wild type plant cell cultures were studied for their capacity to carry out the bioconversion to raspberry ketone using either 4-hydroxybenzalacetone or betuligenol as a substrate. Apparently plant cells possess rather widely distributed reductase activity capable of performing the bioconversion to raspberry ketone using cheap and readily available precursors.

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Section: Discussioncontrasting

confidence: 63%

Bioconversion to Raspberry Ketone is Achieved by Several Non-related Plant Cell Cultures

et al. 2015

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“…The choice of the microbial system suitable for the oxidation of 2 to 1 depended upon the enantiomeric composition of the substrate. Indeed, the enantioselectivity in the oxidation changed from S to R on going from Beauveria bassiana to Candida boidinii (Fuganti et al, 1996;Dumont et al, 1995). To this end, carbinol 2, extracted from T. baccata, was shown, on the basis of optical measurements, HPLC analysis on a chiral column, and comparison with an authentic sample (Fuganti et al, 1996), to contain ca.…”

Section: Resultsmentioning

confidence: 99%

Stable Isotope Characterization of Raspberry Ketone Extracted from Taxus baccata and Obtained by Oxidation of the Accompanying Alcohol (Betuligenol)

Fronza

Fuganti²,

Pedrocchi-Fantoni³

et al. 1999

J. Agric. Food Chem.

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The natural abundance (2)H NMR characterization of raspberry ketone 1 extracted from himalayan Taxus baccata and of the accompanying (R) carbinol 2 is performed and compared with that of samples of 1 obtained from 2 by oxidation with Candida boidinii and CrO(3), respectively. The determination of the delta((13)C) and/or delta((18)O) values of the above extractive products and of benzoic acid (6) and 4-butylphenol (10), obtained from natural of synthetic 1, and of 4-phenylbutan-2-ol (8), prepared from extractive 2, allows a description of the labeling pattern of this set of products. A graph of (D/H)(3)/(D/H)(2) vs (D/H)(5)/(D/H)(4) (Figure 3) of the presently examined samples and of those previously characterized in the laboratory, including three commercial samples sold as natural, defines three areas, containing (a) the material of botanical origin and that produced from extractive 2 by biooxidation, (b) those produced by bioreduction of the unsaturated ketone 3, and (c) the synthetic samples.

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“…In addition, the compounds orcinol, tryptophol, indole-3-acetic acid, himanimide C, and 2-phenylethanol have been found in culture filtrates of the wild-type strain (Supplemental Figure 5 online). Interestingly, tyrosol, which has been described as a PK in the fungus Beauveria bassiana (Fuganti et al, 1996), was present in culture filtrates of both wild-type and Dppt1 strains, suggesting that tyrosol is synthesized via the shikimate pathway.…”

Section: Complementation Of Yeast Mutant Dlys5 and 4'-phosphopantethementioning

confidence: 99%

Sfp-Type 4′-Phosphopantetheinyl Transferase Is Indispensable for Fungal Pathogenicity

et al. 2009

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In filamentous fungi, Sfp-type 4'-phosphopantetheinyl transferases (PPTases) activate enzymes involved in primary (a-aminoadipate reductase [AAR]) and secondary (polyketide synthases and nonribosomal peptide synthetases) metabolism. We cloned the PPTase gene PPT1 of the maize anthracnose fungus Colletotrichum graminicola and generated PPTasedeficient mutants (Dppt1). Dppt1 strains were auxotrophic for Lys, unable to synthesize siderophores, hypersensitive to reactive oxygen species, and unable to synthesize polyketides (PKs). A differential analysis of secondary metabolites produced by wild-type and Dppt1 strains led to the identification of six novel PKs. Infection-related morphogenesis was affected in Dppt1 strains. Rarely formed appressoria of Dppt1 strains were nonmelanized and ruptured on intact plant. The hyphae of Dppt1 strains colonized wounded maize (Zea mays) leaves but failed to generate necrotic anthracnose disease symptoms and were defective in asexual sporulation. To analyze the pleiotropic pathogenicity phenotype, we generated AAR-deficient mutants (Daar1) and employed a melanin-deficient mutant (M1.502). Results indicated that PPT1 activates enzymes required at defined stages of infection. Melanization is required for cell wall rigidity and appressorium function, and Lys supplied by the AAR1 pathway is essential for necrotrophic development. As PPTase-deficient mutants of Magnaporthe oryzea were also nonpathogenic, we conclude that PPTases represent a novel fungal pathogenicity factor.

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Biogeneration and Biodegradation of Raspberry Ketone in the Fungus Beauveria bassiana

Cited by 20 publications

References 7 publications

Bioconversion to Raspberry Ketone is Achieved by Several Non-related Plant Cell Cultures

Bioconversion to Raspberry Ketone is Achieved by Several Non-related Plant Cell Cultures

Stable Isotope Characterization of Raspberry Ketone Extracted from Taxus baccata and Obtained by Oxidation of the Accompanying Alcohol (Betuligenol)

Sfp-Type 4′-Phosphopantetheinyl Transferase Is Indispensable for Fungal Pathogenicity

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