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Anthony R. Borneman - One of the best experts on this subject based on the ideXlab platform.
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heterologous production of Raspberry Ketone in the wine yeast saccharomyces cerevisiae via pathway engineering and synthetic enzyme fusion
Microbial Cell Factories, 2016Co-Authors: Natoiya D.r. Lloyd, Anthony R. Borneman, Isak S. PretoriusAbstract:Raspberry Ketone is the primary aroma compound found in raspberries and naturally derived Raspberry Ketone is a valuable flavoring agent. The economic incentives for the production of Raspberry Ketone, combined with the very poor yields from plant tissue, therefore make this compound an excellent target for heterologous production in synthetically engineered microbial strains. A de novo pathway for the production of Raspberry Ketone was assembled using four heterologous genes, encoding phenylalanine/tyrosine ammonia lyase, cinnamate-4-hydroxlase, coumarate-CoA ligase and benzalacetone synthase, in an industrial strain of Saccharomyces cerevisiae. Synthetic protein fusions were also explored as a means of increasing yields of the final product. The highest Raspberry Ketone concentration achieved in minimal media exceeded 7.5 mg/L when strains were fed with 3 mM p-coumaric acid; or 2.8 mg/L for complete de novo synthesis, both of which utilized a coumarate-CoA ligase, benzalacetone synthase synthetic fusion protein that increased yields over fivefold compared to the native enzymes. In addition, this strain was shown to be able to produce significant amounts of Raspberry Ketone in wine, with a Raspberry Ketone titer of 3.5 mg/L achieved after aerobic fermentation of Chardonnay juice or 0.68 mg/L under anaerobic winemaking conditions. We have shown that it is possible to produce sensorially-relevant quantities of Raspberry Ketone in an industrial heterologous host. This paves the way for further pathway optimization to provide an economical alternative to Raspberry Ketone derived from plant sources.
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MOESM1 of Heterologous production of Raspberry Ketone in the wine yeast Saccharomyces cerevisiae via pathway engineering and synthetic enzyme fusion
2016Co-Authors: Danna Lee, Natoiya Lloyd, Isak Pretorius, Anthony R. BornemanAbstract:Additional file 1: Fig. S1. Fermentation kenetics of during Raspberry Ketone production. AWRI2975, AWRI2975 containing an empty vector integrated at HO (control) and AtC4H RtPAL Pc4Cl2-r-RpBAS (RK) were all used to ferment synthetic Chardonnay juice under either anaerobic (A) or aerobic conditions (B). Absorbance (OD600) and residual sugar were both recorded at 24Â h intervals for 5Â days
Phillip W. Taylor - One of the best experts on this subject based on the ideXlab platform.
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Sexual inhibition of female Queensland fruit flies mated by males treated with Raspberry Ketone supplements as immature adults
Journal of Applied Entomology, 2018Co-Authors: Humayra Akter, Phillip W. TaylorAbstract:Raspberry Ketone (RK) dietary supplements accelerate the emergence of sexual behaviour in developing Queensland fruit fly (Q‐fly) males and show promise as a pre‐release supplement for use in sterile insect technique (SIT) programs. However, the value of RK supplements in SIT programs would be greatly reduced if RK‐treated males are ineffective at inducing sexual inhibition in mated females. To test the effectiveness of matings by RK‐treated males, we here investigate the remating propensity of females mated by RK‐treated (1.25% or 5% RK in food) and RK‐untreated (control) males. Tested males received RK supplements mixed in sugar and yeast hydrolysate for 2 days after emerging and then received only sugar. To test for male age‐dependent effects, virgin females were mated to treated and untreated males that were 6, 8, 10, 20 or 30 days old. To test for persistence of sexual inhibition, mated females were tested for remating propensity at 1, 7 or 15 days after their first mating. RK‐treated males did not differ from control males in copula duration, and females mated by RK‐treated males did not differ from those mated by control males in remating propensity, second copula latency or second copula duration. RK‐treated Q‐fly males not only mate at younger ages but also their matings are as effective as those of untreated controls at inducing sexual inhibition in mates.
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Suppression of cuelure attraction in male Queensland fruit flies provided Raspberry Ketone supplements as immature adults.
PLOS ONE, 2017Co-Authors: Humayra Akter, Polychronis Rempoulakis, Renata Morelli, Saleh Mohammad Adnan, Phillip W. TaylorAbstract:Tephritid fruit flies are amongst the most damaging insect pests of horticulture globally. Some of the key fruit fly species are managed using the sterile insect technique (SIT), whereby millions of sterile males are released to suppress reproduction of pest populations. Male annihilation technique (MAT), whereby sex specific lures are used to attract and kill males, is often used to reduce wild male numbers before SIT programs commence, providing released sterile males an increased numerical advantage. Overall program efficacy might be improved if MAT could be deployed simultaneously with SIT, continuously depleting fertile males from pest populations and replacing them with sterile males. However, such 'male replacement' requires a means of suppressing attraction of released sterile males to lures used in MAT. Previous studies have found that exposure of some fruit flies to lure compounds as mature adults can suppress subsequent response to those lures, raising the possibility of pre-release treatments. However, this approach requires holding flies until after maturation for treatment and then release. The present study takes a novel approach of exposing immature adult male Queensland fruit flies (Bactrocera tryoni, or 'Qfly') to Raspberry Ketone (RK) mixed in food, forcing these flies to ingest RK at ages far younger than they would naturally. After feeding on RK-supplemented food for two days after emergence, male Qflies exhibited a reduction in attraction to cuelure traps that lasted more than 20 days. This approach to RK exposure is compatible with current practises, in which Qflies are released as immature adults, and also yields advantages of accelerated reproductive development and increased mating propensity at young ages.
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Raspberry Ketone supplement promotes early sexual maturation in male Queensland fruit fly, Bactrocera tryoni (Diptera: Tephritidae)
Pest Management Science, 2017Co-Authors: Humayra Akter, Renata Morelli, Vivian Mendez, Jeanneth Pérez, Phillip W. TaylorAbstract:BACKGROUND Raspberry Ketone (RK) is highly attractive to sexually mature, but not immature, males of many Bactrocera species, including Queensland fruit fly ('Qfly', Bactrocera tryoni), and acts as a metabolic enhancer in a wide diversity of animals. We considered the possibility that, as a metabolic enhancer, RK in adult diet might accelerate sexual maturation of male Qflies. RESULTS Recently emerged adult Qfly males (0-24 h old) were exposed to RK-treated food for 48 h and were then provided only sugar and water. Four doses of RK (1.25, 2.5, 3.75 and 5%) along with control (0%) were tested with two types of food: sugar alone and sugar mixed with yeast hydrolysate (3:1). For flies tested when 4-10 days old all RK doses increased mating probability of flies fed sugar mixed with yeast hydrolysate but did not show any effect on mating probability of flies fed only sugar. No effects of RK were found for flies tested when 10-30 days old for either diet group. There was no evidence that RK affected longevity at any of the doses tested. CONCLUSION Feeding of RK together with yeast hydrolysate to immature Qfly increases mating propensity at young ages and accordingly shows significant potential as a pre-release supplement that might increase the proportion of released flies that attain sexual maturation in Sterile Insect Technique programmes. © 2017 Society of Chemical Industry.
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Raspberry Ketone Analogs: Vapour Pressure Measurements and Attractiveness to Queensland Fruit Fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae).
PLOS ONE, 2016Co-Authors: Soo J. Park, Matthew S. Siderhurst, Ian M. Jamie, Renata Morelli, Benjamin L. Hanssen, Joanne F. Jamie, Phillip W. TaylorAbstract:The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry Ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.
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Raspberry Ketone Trifluoroacetate, a New Attractant for the Queensland Fruit Fly, Bactrocera Tryoni (Froggatt)
Journal of Chemical Ecology, 2016Co-Authors: Matthew S. Siderhurst, Eric B. Jang, Soo J. Park, Caitlyn N. Buller, Ian M. Jamie, Nicholas C. Manoukis, Phillip W. TaylorAbstract:Queensland fruit fly, Bactrocera tryoni (Q-fly), is a major pest of horticultural crops in eastern Australia. Lures that attract male Q-fly are important for detection of incursions and outbreaks, monitoring of populations, and control by mass trapping and male annihilation. Cuelure, an analog of naturally occurring Raspberry Ketone, is the standard Q-fly lure, but it has limited efficacy compared with lures that are available for some other fruit flies such as methyl eugenol for B. dorsalis . Melolure is a more recently developed Raspberry Ketone analog that has shown better attraction than cuelure in some field studies but not in others. A novel fluorinated analog of Raspberry Ketone, Raspberry Ketone trifluoroacetate (RKTA), has been developed as a potential improvement on cuelure and melolure. RKTA placed on laboratory cages containing 2-week-old Q-flies elicited strong behavioral responses from males. Quantification of Q-fly responses in these cages, using digital images to estimate numbers of flies aggregated near different lures, showed RKTA attracted and arrested significantly more flies than did cuelure or melolure. RKTA shows good potential as a new lure for improved surveillance and control of Q-fly.
Daniel Joulain - One of the best experts on this subject based on the ideXlab platform.
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Natural Abundance 2H Nuclear Magnetic Resonance Study of the Origin of Raspberry Ketone
Journal of Agricultural and Food Chemistry, 1998Co-Authors: Giovanni Fronza, Claudio Fuganti, Claude Guillou, Fabiano Reniero, Daniel JoulainAbstract:The site-specific natural abundance deuterium distribution of Raspberry Ketone 3 obtained through a variety of methods has been determined through 2H NMR spectroscopy. This technique provided a means of distinguishing between “natural” Raspberry Ketones biogenerated from 4-hydroxybenzalacetone (2), obtained from 4-hydroxybenzaldehyde of extractive botanical origin and acetone produced by sugar fermentation by reduction using baker's yeast and other microorganisms, and other Raspberry Ketone samples obtained in different “non-natural” ways. Of natural origin is also a commercial sample obtained in an unspecified manner. A mechanistic interpretation has been proposed to explain the difference of site-specific deuterium content between the examined samples. Keywords: Natural abundance 2H NMR; Raspberry Ketone; natural; adulteration
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stereochemistry of the baeyer villiger type conversion of 4 4 hydroxyphenyl butan 2 one Raspberry Ketone into tyrosol mediated by beauveria bassiana
Journal of Organic Chemistry, 1996Co-Authors: Giovanni Fronza, Claudio Fuganti, Gioia Zucchi, Valentina Perozzo, And Stefano Servi, Giuseppe Pedrocchifantoni, Daniel JoulainAbstract:Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-2H2]-4-(4-hydroxyphenyl)butan-2-ol (15) and (2R,3R)-[1,3-2H4]-4-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (1R)-[1-2H]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6−C-4 framework of the intermediate Raspberry Ketone 1 to give the C-6−C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, prepared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.
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Biogeneration and Biodegradation of Raspberry Ketone in the Fungus Beauveria bassiana
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Claudio Fuganti, Monica Mendozza, Daniel Joulain, Jose Minut, Giuseppe Pedrocchi-fantoni, Valentino Piergianni, Stefano Servi, Gioia ZucchiAbstract:In growing cultures of the fungus Beauveria bassiana (ATCC 7159) the incubation of 4-(4‘-hydroxyphenyl)but-3-en-2-one (p-hydroxybenzylidenacetone, 3), of 4-(4‘-hydroxyphenyl)butan-2-one (Raspberry Ketone, 1), and of the S and R,S forms of 4-(4‘-hydroxyphenyl)butan-2-ol (2) yields 2-(4‘-hydroxyphenyl)ethanol (tyrosol, 4) as a final product. The experiments support the view that the actual substrate for the Baeyer−Villiger-type degradation is Raspberry Ketone (1) and that there is a kinetic preference in the microbial enzymatic system for the oxidation to 1 of the S form of the 4-(4‘-hydroxyphenyl)butan-2-ol (2). Keywords: Raspberry Ketone; tyrosol; degradation; Beauveria bassiana; Baeyer−Villiger oxidation; stereochemistry
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On the Mode of Microbial Biogeneration of Raspberry Ketone and Related Compounds
Flavour and Fragrance Journal, 1996Co-Authors: Claudio Fuganti, Monica Mendozza, Gioia Zucchi, Daniel JoulainAbstract:The mode of reduction through fermenting baker's yeast and Hansenula anomala CBS 110 of 4-phenylbut-3-en-2-ones 7-9 has been studied. The ratio between saturated Ketones 1-3, saturated carbinols 4-6 and starting materials 7-9 depends upon the microorganism used and the incubation period. When using as substrate Ketone 7, obtained from natural precursors and baker's yeast as reducing agent, up to 80.5% of natural Raspberry Ketone 1 is obtained.
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Stereochemistry of the Baeyer−Villiger-Type Conversion of 4-(4-Hydroxyphenyl)butan-2-one (Raspberry Ketone) into Tyrosol Mediated by Beauveria bassiana
The Journal of Organic Chemistry, 1996Co-Authors: Giovanni Fronza, Claudio Fuganti, Giuseppe Pedrocchi-fantoni, Gioia Zucchi, Valentina Perozzo, And Stefano Servi, Daniel JoulainAbstract:Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-2H2]-4-(4-hydroxyphenyl)butan-2-ol (15) and (2R,3R)-[1,3-2H4]-4-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (1R)-[1-2H]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6−C-4 framework of the intermediate Raspberry Ketone 1 to give the C-6−C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, prepared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.
Matthew S. Siderhurst - One of the best experts on this subject based on the ideXlab platform.
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Raspberry Ketone Trifluoroacetate Trapping of Zeugodacus cucurbitae (Diptera: Tephritidae) in Hawaii
Journal of Economic Entomology, 2019Co-Authors: Katherine A Lehman, Lori A. Carvalho, Nicholas C. Manoukis, Stefano G. De Faveri, Diego C. Barahona, Jean E Auth, Matthew S. SiderhurstAbstract:Melon fly, Zeugodacus cucurbitae (Coquillett), is a serious pest of tropical horticulture, causing damage to cucurbits, other fruiting vegetables, and certain tree fruits. The deployment of male lures comprises an important component of several detection and control strategies for this pest, with the main male attractant currently in use being cuelure (CL). A novel fluorinated analog of CL, Raspberry Ketone trifluoroacetate (RKTA), has been developed for the control of Bactrocera tryoni, a related pest; here, we test this compound for attraction to Z. cucurbitae. In outdoor screen cage testing, observations showed both more flies on filter papers, and a higher percentage of flies feeding, on papers treated with RKTA than on those with CL or melolure (ML). Field trapping with both yellow sticky traps and bucket traps found that RKTA captured more flies during the first 6 h of trapping than CL, while trap captures in the subsequent 18 h did not differ between the two lures. When comparing combined 24 h trap captures, yellow sticky traps containing RKTA captured more flies than those with CL, while bucket trap captures did not vary by lure. Analysis of lures weathered on filter paper found that nearly all applied RKTA hydrolyzed to RK within 6 h. Fine-scale melon fly behaviors digitally recorded in the field showed median resting distances from the lure of responding flies were shorter for RKTA than for CL. This study demonstrates the inherent attractiveness of RKTA while also highlighting the instability of this compound due to hydrolysis.
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Electroantennogram responses of six Bactrocera and Zeugodacus species to Raspberry Ketone analogues
Environmental Chemistry, 2017Co-Authors: Matthew S. Siderhurst, Soo J. Park, Ian M. Jamie, Stefano G. De FaveriAbstract:Environmental context Queensland fruit fly is a major pest of fruits and vegetables in eastern Australia, sometimes causing complete loss of unprotected crops. Odours that attract fruit flies can help control these pests and this study investigated how six fruit fly species smell these chemicals. The strength of fly responses to tested odours gives insight into the way flies smell and provides information for making better attractants, potentially reducing insecticide use. Abstract The Queensland fruit fly (Bactrocera tryoni, Q-fly) is a major horticultural pest in eastern Australia. The deployment of male lures comprises an important component of several detection and control strategies for this pest. A novel fluorinated analogue of Raspberry Ketone (RK), Raspberry Ketone trifluoroacetate (RKTA), has been developed with the aim of further improving Q-fly control. RKTA elicited strong electroantennogram (EAG) responses from Q-flies whereas cuelure (CL) and melolure (ML) responses were not significantly greater than a negative control. Further experimentation showed that RKTA also elicited EAG response from five other fruit fly species, included flies known to be strongly attracted to CL (B. neohumeralis, B. kraussi and B. frauenfeldi), weakly attracted to CL (B. jarvisi), or non-responsive to CL (Zeugodacus cucumis), whereas seven other compounds, RK, CL, ML, Raspberry Ketone difluoroacetate, Raspberry Ketone monofluoroacetate, anisyl acetone and trimethylsilyl Raspberry Ketone, elicited only weak responses comparable with a negative control. However, fly EAG responses to RKTA are likely due at least in part to trifluoroethanoic acid, which is a hydrolysis product of RKTA and elicited strong EAG responses from all six species when tested alone. Furthermore, whereas ethanoic acid, methanoic acid and trifluoroethanoic acid all elicited strong EAG responses in Q-flies, the only corresponding RK ester to elicit an EAG response was RKTA, suggesting that RKTA hydrolyses quickly, whereas CL and ML do not. This is in contrast to the idea that CL readily hydrolyses on contact with atmospheric moisture, an assertion that has been made in the literature repeatedly.
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Raspberry Ketone Analogs: Vapour Pressure Measurements and Attractiveness to Queensland Fruit Fly, Bactrocera tryoni (Froggatt) (Diptera: Tephritidae).
PLOS ONE, 2016Co-Authors: Soo J. Park, Matthew S. Siderhurst, Ian M. Jamie, Renata Morelli, Benjamin L. Hanssen, Joanne F. Jamie, Phillip W. TaylorAbstract:The Queensland fruit fly, Bactrocera tryoni (Froggatt) (Q-fly), is a major horticultural pest in Eastern Australia. Effective monitoring, male annihilation technique (MAT) and mass trapping (MT) are all important for control and require strong lures to attract flies to traps or toxicants. Lure strength is thought to be related in part to volatility, but little vapour pressure data are available for most Q-fly lures. Raspberry Ketone (4-(4-hydroxyphenyl)-2-butanone) and analogs that had esters (acetyl, difluoroacetyl, trifluoroacetyl, formyl, propionyl) and ethers (methyl ether, trimethylsilyl ether) in replacement of the phenolic group, and in one case also had modification of the 2-butanone side chain, were measured for their vapour pressures by differential scanning calorimetry (DSC), and their attractiveness to Q-fly was assessed in small cage environmentally controlled laboratory bioassays. Maximum response of one category of compounds, containing both 2-butanone side chain and ester group was found to be higher than that of the other group of compounds, of which either of 2-butanone or ester functionality was modified. However, linear relationship between vapour pressure and maximum response was not significant. The results of this study indicate that, while volatility may be a factor in lure effectiveness, molecular structure is the dominating factor for the series of molecules investigated.
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Raspberry Ketone Trifluoroacetate, a New Attractant for the Queensland Fruit Fly, Bactrocera Tryoni (Froggatt)
Journal of Chemical Ecology, 2016Co-Authors: Matthew S. Siderhurst, Eric B. Jang, Soo J. Park, Caitlyn N. Buller, Ian M. Jamie, Nicholas C. Manoukis, Phillip W. TaylorAbstract:Queensland fruit fly, Bactrocera tryoni (Q-fly), is a major pest of horticultural crops in eastern Australia. Lures that attract male Q-fly are important for detection of incursions and outbreaks, monitoring of populations, and control by mass trapping and male annihilation. Cuelure, an analog of naturally occurring Raspberry Ketone, is the standard Q-fly lure, but it has limited efficacy compared with lures that are available for some other fruit flies such as methyl eugenol for B. dorsalis . Melolure is a more recently developed Raspberry Ketone analog that has shown better attraction than cuelure in some field studies but not in others. A novel fluorinated analog of Raspberry Ketone, Raspberry Ketone trifluoroacetate (RKTA), has been developed as a potential improvement on cuelure and melolure. RKTA placed on laboratory cages containing 2-week-old Q-flies elicited strong behavioral responses from males. Quantification of Q-fly responses in these cages, using digital images to estimate numbers of flies aggregated near different lures, showed RKTA attracted and arrested significantly more flies than did cuelure or melolure. RKTA shows good potential as a new lure for improved surveillance and control of Q-fly.
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Vapour Pressure (P) and Enthalpy of Vaporisation (ΔHvap) of Raspberry Ketone and Eight Analogs at 298.15 K.
2016Co-Authors: Soo J. Park, Matthew S. Siderhurst, Ian M. Jamie, Renata Morelli, Benjamin L. Hanssen, Joanne F. Jamie, Phillip W. TaylorAbstract:Vapour Pressure (P) and Enthalpy of Vaporisation (ΔHvap) of Raspberry Ketone and Eight Analogs at 298.15 K.
Kazufumi Yazaki - One of the best experts on this subject based on the ideXlab platform.
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characterization of Raspberry Ketone zingerone synthase catalyzing the alpha beta hydrogenation of phenylbutenones in Raspberry fruits
Biochemical and Biophysical Research Communications, 2011Co-Authors: Takao Koeduka, Junichi Mano, Bunta Watanabe, Jun Hiratake, Shiro Suzuki, Kazufumi YazakiAbstract:Abstract Phenylbutanone Raspberry Ketone, accumulating in the mature fruits of Raspberry (Rubus idaeus), imparts the characteristic aroma to the fruits. Here we describe the isolation and characterization of Raspberry Ketone/zingerone synthase 1 (RZS1), which catalyzed the NADPH-dependent reduction of 4-hydroxybenzalacetone and 3-methoxy-4-hydroxybenzalacetone to Raspberry Ketone and zingerone (the latter not found in Raspberry), respectively. Its apparent Km values for 4-hydroxybenzalacetone and NADPH were 88 μM and 202 μM, respectively. RZS1 preferred 4-hydroxybenzalacetone to 3-methoxy-4-hydroxybenzalacetone as a substrate by a factor of 1.7, and showed a 6-fold preference for 4-hydroxybenzalacetone over p-coumaraldehyde, and no activity for coniferaldehyde. Expression analysis of the RZS1 gene throughout the plant revealed that its transcript level was highest in mature fruits. We conclude that RZS1 is responsible for hydrogenation of the α,β-unsaturated double bond of phenylbutenones, the final step of the Raspberry Ketone biosynthesis, in the Raspberry fruits.
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Characterization of Raspberry Ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in Raspberry fruits
Biochemical and Biophysical Research Communications, 2011Co-Authors: Takao Koeduka, Junichi Mano, Bunta Watanabe, Jun Hiratake, Shiro Suzuki, Kazufumi YazakiAbstract:Abstract Phenylbutanone Raspberry Ketone, accumulating in the mature fruits of Raspberry (Rubus idaeus), imparts the characteristic aroma to the fruits. Here we describe the isolation and characterization of Raspberry Ketone/zingerone synthase 1 (RZS1), which catalyzed the NADPH-dependent reduction of 4-hydroxybenzalacetone and 3-methoxy-4-hydroxybenzalacetone to Raspberry Ketone and zingerone (the latter not found in Raspberry), respectively. Its apparent Km values for 4-hydroxybenzalacetone and NADPH were 88 μM and 202 μM, respectively. RZS1 preferred 4-hydroxybenzalacetone to 3-methoxy-4-hydroxybenzalacetone as a substrate by a factor of 1.7, and showed a 6-fold preference for 4-hydroxybenzalacetone over p-coumaraldehyde, and no activity for coniferaldehyde. Expression analysis of the RZS1 gene throughout the plant revealed that its transcript level was highest in mature fruits. We conclude that RZS1 is responsible for hydrogenation of the α,β-unsaturated double bond of phenylbutenones, the final step of the Raspberry Ketone biosynthesis, in the Raspberry fruits.
