A Labeling Study To Elucidate the Biosynthesis of 4-(4-Hydroxyphenyl)-Butan-2-one (Raspberry Ketone) by
            <i>Nidula niveo-tomentosa</i>

Zorn, Holger; Fischer-Zorn, M.; Berger, Ralf G.

doi:10.1128/aem.69.1.367-372.2003

Cited by 17 publications

(8 citation statements)

References 20 publications

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“…Having the synthetic standard simplifies the validation of this sulfated metabolite in human samples. Raspberry ketone can also be produced through the phenylalanine degradation pathway [ 40 ]. We have also synthesized several compounds that are sulfated analogues of products from bacterial degradation of anthocyanins (vanillin, sinapic acid, or syringic acid) [ 41 , 42 ].…”

Section: Resultsmentioning

confidence: 99%

Rapid Preparation of a Large Sulfated Metabolite Library for Structure Validation in Human Samples

et al. 2020

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Metabolomics analysis of biological samples is widely applied in medical and natural sciences. Assigning the correct chemical structure in the metabolite identification process is required to draw the correct biological conclusions and still remains a major challenge in this research field. Several metabolite tandem mass spectrometry (MS/MS) fragmentation spectra libraries have been developed that are either based on computational methods or authentic libraries. These libraries are limited due to the high number of structurally diverse metabolites, low commercial availability of these compounds, and the increasing number of newly discovered metabolites. Phase II modification of xenobiotics is a compound class that is underrepresented in these databases despite their importance in diet, drug, or microbiome metabolism. The O-sulfated metabolites have been described as a signature for the co-metabolism of bacteria and their human host. Herein, we have developed a straightforward chemical synthesis method for rapid preparation of sulfated metabolite standards to obtain mass spectrometric fragmentation pattern and retention time information. We report the preparation of 38 O-sulfated alcohols and phenols for the determination of their MS/MS fragmentation pattern and chromatographic properties. Many of these metabolites are regioisomers that cannot be distinguished solely by their fragmentation pattern. We demonstrate that the versatility of this method is comparable to standard chemical synthesis. This comprehensive metabolite library can be applied for co-injection experiments to validate metabolites in different human sample types to explore microbiota-host co-metabolism, xenobiotic, and diet metabolism.

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Section: Resultsmentioning

confidence: 99%

Rapid Preparation of a Large Sulfated Metabolite Library for Structure Validation in Human Samples

et al. 2020

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“…Variation of the composition of the nutrient medium supported by a factorial experimental design yielded a 50-fold increase in metabolite concentrations. This allowed for a Biotechnological flavour generation 99 follow-up labelling study using phenylpropanoid precursor substrates, and it turned out that l-phenylalanine was degraded to a benzylic intermediate and then side chain elongated in two subsequent steps (Zorn et al, 2003b). Exposure to UV light stimulated the growth of the basidiomycete and the synthesis of raspberry alcohol and ketone.…”

Section: Generation Of Vanillin Benzaldehyde and Benzoic Compoundsmentioning

confidence: 99%

Biotechnological Flavour Generation

Berger

Krings

Zorn

2010

Food Flavour Technology

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“…4-(4-hydroxyphenyl)butan-2-one, commonly referred to as raspberry ketone, is the major fragrance compound from raspberry berries ( Rubeus rubrum ). Raspberry ketone is harvested by chemical extraction at a ratio of 1-4 mg per kilo of fruit 16 . This presents a highly-inefficient purification process, which is reflected by a high market price for naturally extracted raspberry ketone that fluctuates at approximately $10,000-20,000 kg −1 , with global production estimated at between 100-200 tons per annum 16,17 .…”

Section: Introductionmentioning

confidence: 99%

“…Raspberry ketone is harvested by chemical extraction at a ratio of 1-4 mg per kilo of fruit 16 . This presents a highly-inefficient purification process, which is reflected by a high market price for naturally extracted raspberry ketone that fluctuates at approximately $10,000-20,000 kg −1 , with global production estimated at between 100-200 tons per annum 16,17 . As an alternative green solution for its production, raspberry ketone can be synthesised in microbial cells.…”

Section: Introductionmentioning

confidence: 99%

A cell-free synthetic biochemistry platform for raspberry ketone production

Tosi

Bell

Hleba

et al. 2017

Preprint

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22Cell-free synthetic biochemistry provides a green solution to replace traditional 23 petroleum or agricultural based methods for production of fine chemicals. 4-(4-24 hydroxyphenyl)-butan-2-one, also known as raspberry ketone, is the major fragrance 25 component of raspberry fruit and is utilised as a natural additive in the food and 26 sports industry. Current industrial processing standards involve chemical extraction 27with a yield of 1-4 mg per kilo of fruit. As such its market price can fluctuate up to 28 $20,000 per kg. Metabolic engineering approaches to synthesise this molecule by 29 microbial fermentation have only resulted in low yields of up to 5 mg L -1 . In contrast, 30 cell-free synthetic biochemistry offers an intriguing compromise to the engineering 31 constraints provided by the living cell. Using purified enzymes or a two-step semi-32 synthetic route, an optimised pathway was formed for raspberry ketone synthesis 33 leading up to 100% yield conversion. The semi-synthetic route is potentially scalable 34 and cost-efficient for industrial synthesis of raspberry ketone.

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A Labeling Study To Elucidate the Biosynthesis of 4-(4-Hydroxyphenyl)-Butan-2-one (Raspberry Ketone) by Nidula niveo-tomentosa

Cited by 17 publications

References 20 publications

Rapid Preparation of a Large Sulfated Metabolite Library for Structure Validation in Human Samples

Rapid Preparation of a Large Sulfated Metabolite Library for Structure Validation in Human Samples

Biotechnological Flavour Generation

A cell-free synthetic biochemistry platform for raspberry ketone production

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