Vanillin–Bioconversion and Bioengineering of the Most Popular Plant Flavor and Its De Novo Biosynthesis in the Vanilla Orchid

Gallage, Nethaji J.; Møller, Birger Lindberg

doi:10.1016/j.molp.2014.11.008

Cited by 276 publications

(198 citation statements)

References 114 publications

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“…Vanillin ( 3 ), a phenolic aldehyde that can be synthesized or isolated from processed Vanilla planifolia and Vanilla tahitensis seed pods and used as a flavouring/fragrance agent or in a popular TLC stain, 24,25 was included into 1 ·CHCl 3 . Crystals of 1 ·CHCl 3 were soaked in a 0.5 M solution of 3 in MTBE at ambient temperature for 3 days, where the crystals immediately developed a light yellow colour.…”

Section: Resultsmentioning

confidence: 99%

The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

et al. 2017

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A strategy that leverages solvent effects to noncovalently trap solid and unstable liquid organic compounds within a crystalline sponge ({[(ZnI2)3(tris(4-pyridyl)-1,3,5-triazine)2]·x(CHCl3)}n) in a simple, mild, and efficient fashion for target molecule structure determination via X-ray diffraction is disclosed. Host-guest structures were obtained using third-generation synchrotron radiation, and new beamline hardware allowed rapid data collection in ~5–24 minutes. This is 40–90% faster than previously reported crystalline sponge synchrotron datasets collected by us, and approximately a 150–720–fold decrease in time versus using a typical in-house diffractometer, effectively enabling the potential for high-throughput analysis. The new target molecule inclusion method using methyl tert-butyl ether (MTBE) solvent was demonstrated by trapping (E)-stilbene, vanillin, 4-(trifluoromethyl)phenyl azide, and (+)-artemisinin (an antimalarial drug). The potential of guests to maximize intermolecular interactions with the crystalline sponge framework at the expense of attenuating intramolecular interactions (e.g., π-conjugation) was observed for (E)-stilbene. Trapping of vanillin and (+)-artemisinin elicited single-crystal-to-single-crystal transformations where space group symmetry reduced from C2/c to P1̄ and C2, respectively, and the absolute configuration of (+)-artemisinin was determined through anomalous dispersion.

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Section: Resultsmentioning

confidence: 99%

The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

et al. 2017

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“…Indeed, in 2013, vanilla beans were negotiated at €53 per kg, whereas in 2017 the price for 1 kg reached €500 . Over the last 20 years, an alternative to vanillin derived from the bean was obtained from many processes intended to produce natural vanillin by fermentation, biotransformation, or bioconversion, also called biosynthesis, using natural sources other than vanilla pods . Vanillin considered as a natural product is obtained through processes using three main molecules currently used as precursors: ferulic acid extracted from Oryza sativa L. (ex‐ferulic acid from rice) and ferulic acid extracted from Zea mays L. (ex‐ferulic acid from maize), eugenol obtained from Syzygium aromaticum (L.) Merrill & Perry (ex‐eugenol from clove oil), and curcumin extracted from Curcuma L. (ex‐curcumin from curcuma).…”

Section: Introductionmentioning

confidence: 99%

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Guyader

Thomas

Jamin

et al. 2019

Flavour & Fragrance J

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Synthetic vanillin is the flavouring most used in agro‐food industries, but more and more frequently consumers are now turning to natural origin. Vanilla planifolia (Andrews) is the most commercialized species of pods in the world and is mainly produced in Madagascar. However, periodically the production of V. planifolia suffers from poor climatic conditions, with the resulting degradation of both the quality and the quantity of the pods. Consequently, the price of vanilla pods rose to record in 2017 and the risk of fraud has increased in response. Analytical methods based on isotopic compositions have already proven their ability to ensure the authenticity of natural vanillin. In 2006, 2H SNIF‐NMR (site‐specific natural isotopic fractionation by nuclear magnetic resonance) was approved as official method by the Association of Official Analytical Chemists (AOAC 2006.05). However, this method is time consuming and the extraction of 1 g is cumbersome for the finished products. The information brought by combined 2H and 13C SNIF‐NMR profiles was compared using chemometric tools to determine the best routine tool to improve both the global analysis time and the potential of detection. As a result of this work the ability of the SNIF‐NMR method to verify the authenticity of vanillin has been improved, in particular by providing the first means to discern the geographical origin of vanilla pods. Furthermore, 13C NMR using pulse sequences such as INEPT (insensitive nuclei enhanced by polarization transfer) offers the possibility to improve the sensitivity of the analysis, with a reduced quantity of product (less than 50 mg) and a shorter analysis time, which will facilitate the study of the finished matrices as well as clearly discriminating the origins of the vanilla flavourings.

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“…and Møller [52]. De novo biosynthesis of vanillin from glucose in S. cerevisiae has also been reported [53].…”

Section: Flavoursmentioning

confidence: 90%

Advances in Metabolic Engineering of Saccharomyces cerevisiae for the Production of Industrially and Clinically Important Chemicals

Turanlı-Yıldız¹,

Hacısalihoğlu²,

Çakar³

2017

Old Yeasts - New Questions

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Sustainable production of chemicals is of increasing importance, due to depletion of petroleum and environmental concerns. In addition to its importance in basic research as a simple, eukaryotic model organism, Saccharomyces cerevisiae has long been exploited in industry because of its physiological properties. And today, the development in genetic engineering toolbox and genome-scale metabolic models of S. cerevisiae has extended its application range to new products and bioprocesses. In addition, evolutionary engineering strategies have been useful in improving cellular properties of S. cerevisiae, such as tolerance to product toxicity and inhibitors. In this chapter, recent metabolic and evolutionary engineering studies that involve S. cerevisiae for the production of bulk chemicals and ine chemicals including lavours and pharmaceuticals are reviewed. It was shown that metabolic engineering particularly allowed the improvement of pharmaceuticals production, which will enable economic and large-scale production of many valuable pharmaceuticals. It is clear that S. cerevisiae will continue to be an important host for future metabolic engineering and metabolic pathway engineering applications to produce a variety of industrially and clinically important chemicals.

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Vanillin–Bioconversion and Bioengineering of the Most Popular Plant Flavor and Its De Novo Biosynthesis in the Vanilla Orchid

Cited by 276 publications

References 114 publications

The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Advances in Metabolic Engineering of Saccharomyces cerevisiae for the Production of Industrially and Clinically Important Chemicals

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Vanillin–Bioconversion and Bioengineering of the Most Popular Plant Flavor and Its De Novo Biosynthesis in the Vanilla Orchid

Cited by 276 publications

References 114 publications

The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

Combination of 13C and 2H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors

Advances in Metabolic Engineering of Saccharomyces cerevisiae for the Production of Industrially and Clinically Important Chemicals

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Combination of ¹³C and ²H SNIF‐NMR isotopic fingerprints of vanillin to control its precursors