Biotransformation of Isoeugenol to Vanillin by a Novel Strain of Bacillus fusiformis

Zhao, Lingyun; Sun, Zhihao; Zheng, Pu; Zhu, Longyuan

doi:10.1007/s10529-005-1466-x

Cited by 90 publications

(40 citation statements)

References 10 publications

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“…Strains isolated from soil identified as B. subtilis, B. fusiformis, and B. pumilus are capable of transforming isoeugenol to vanillin (30)(31)(32). Additionally, another B. subtilis isolate showed the ability to produce tetramethylpyrazine (a commonly occurring alkylpyrazine that is responsible for the odor of oriental foods, such as Chinese liquors) via the precursor 3-hydroxy-2-butanone (33).…”

Section: Discussionmentioning

confidence: 99%

Involvement of Colonizing Bacillus Isolates in Glucovanillin Hydrolysis during the Curing of Vanilla planifolia Andrews

Yong-gan

et al. 2015

Appl Environ Microbiol

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Vanilla beans were analyzed using biochemical methods, which revealed that glucovanillin disperses from the inner part to the outer part of the vanilla bean during the curing process and is simultaneously hydrolyzed by ␤-D-glucosidase. Enzymatic hydrolysis was found to occur on the surface of the vanilla beans. Transcripts of the ␤-D-glucosidase gene (bgl) of colonizing microorganisms were detected. The results directly indicate that colonizing microorganisms are involved in glucovanillin hydrolysis. Phylogenetic analysis based on 16S rRNA gene sequences showed that the colonizing microorganisms mainly belonged to the Bacillus genus. bgl was detected in all the isolates and presented clustering similar to that of the isolate taxonomy. Furthermore, inoculation of green fluorescent protein-tagged isolates showed that the Bacillus isolates can colonize vanilla beans. Glucovanillin was metabolized as the sole source of carbon in a culture of the isolates within 24 h. These isolates presented unique glucovanillin degradation capabilities. Vanillin was the major volatile compound in the culture. Other compounds, such as ␣-cubebene, ␤-pinene, and guaiacol, were detected in some isolate cultures. Colonizing Bacillus isolates were found to hydrolyze glucovanillin in culture, indirectly demonstrating the involvement of colonizing Bacillus isolates in glucovanillin hydrolysis during the vanilla curing process. Based on these results, we conclude that colonizing Bacillus isolates produce ␤-D-glucosidase, which mediates glucovanillin hydrolysis and influences flavor formation. V anilla flavoring obtained from cured Vanilla planifolia beans is widely used in food, beverages, and cosmetics, such that the total worldwide consumption is markedly increasing (1, 2). The characteristics of the vanilla flavor are formed only during a careful curing process that yields the main aromatic constituent, vanillin, and over 200 other volatile compounds with delicate sweet fragrances (3).The conventional curing process starts with a blanching step in which the mature green vanilla bean is immersed in hot water for 3 to 5 min. The vanilla beans are then subjected to a process that involves periodic sweating and drying. During the remaining part of the day, the vanilla beans are allowed to acclimate on wooden racks in a well-ventilated room and are then stored in small bundles in plastic vacuum bags at room temperature (4, 5).In fresh vanilla beans, vanillin is exclusively present in a conjugated form, principally as glucovanillin. At this stage, the beans display no trace of vanilla flavor (6, 7). One of the most important aspects of curing is when glucovanillin comes into contact with ␤-D-glucosidase, thus releasing free vanillin (8). Thermal treatment, plant enzyme reactions, and microbial activity are all important in vanillin flavor generation (9). Röling et al. (10) reported that differences in microbial abundance, communities, and strain characteristics result in variations in vanilla flavor. These results show that colonizing microorg...

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Section: Discussionmentioning

confidence: 99%

Involvement of Colonizing Bacillus Isolates in Glucovanillin Hydrolysis during the Curing of Vanilla planifolia Andrews

Yong-gan

et al. 2015

Appl Environ Microbiol

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“…In related research that deals with the biotransformation of plant origin phenylpropanoid compounds, many investigators have focused on isoeugenol and eugenol, both of which can be metabolized into vanillin. For this purpose, diverse bacterial strains, including strains of Bacillus fusiformis (36), B. pumilus strain S-1 (32), B. subtilis HS8 (35), B. subtilis B2 (23), Brevibacillus agri 13 (30), Pseudomonas chlororaphis CDAE5 (6), P. nitroreducens Jin1 (29), P. putida IE27 (33), Psychrobacter sp. strain CSW4 (1), and Nocardia iowensis DSM 45197 (20), have been isolated.…”

Section: Tablementioning

confidence: 99%

Isolation of a Gene Responsible for the Oxidation of trans -Anethole to para -Anisaldehyde by Pseudomonas putida JYR-1 and Its Expression in Escherichia coli

Han

Ryu

Kanaly

et al. 2012

Appl Environ Microbiol

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A plasmid, pTA163, in Escherichia coli contained an approximately 34-kb gene fragment from Pseudomonas putida JYR-1 that included the genes responsible for the metabolism of trans-anethole to protocatechuic acid. Three Tn5-disrupted open reading frame 10 (ORF 10) mutants of plasmid pTA163 lost their abilities to catalyze trans-anethole. Heterologously expressed ORF 10 (1,047 nucleotides [nt]) under a T7 promoter in E. coli catalyzed oxidative cleavage of a propenyl group of trans-anethole to an aldehyde group, resulting in the production of para-anisaldehyde, and this gene was designated tao (trans-anethole oxygenase). The deduced amino acid sequence of TAO had the highest identity (34%) to a hypothetical protein of Agrobacterium vitis S4 and likely contained a flavin-binding site. Preferred incorporation of an oxygen molecule from water into p-anisaldehyde using 18 Olabeling experiments indicated stereo preference of TAO for hydrolysis of the epoxide group. Interestingly, unlike the narrow substrate range of isoeugenol monooxygenase from Pseudomonas putida IE27 and Pseudomonas nitroreducens Jin1, TAO from P. putida JYR-1 catalyzed isoeugenol, O-methyl isoeugenol, and isosafrole, all of which contain the 2-propenyl functional group on the aromatic ring structure. Addition of NAD(P)H to the ultrafiltered cell extracts of E. coli (pTA163) increased the activity of TAO. Due to the relaxed substrate range of TAO, it may be utilized for the production of various fragrance compounds from plant phenylpropanoids in the future. Bacterial metabolism as a means of producing value-added compounds from natural resources has been given much attention as an alternative method to replace conventional chemical syntheses (21,27). If natural resources can be continuously supplied as the starting materials, biotransformation employing bacterial systems may become practical from the points of view of sustainability and applicability. One of the major groups of natural compounds targeted for the production of value-added compounds includes the group of chemicals that occur in plant phenylpropanoid pathways, which are involved in the production of lignin, flavonoids, anthocyanins, etc. (5, 16-19). For example, isoeugenol, eugenol, and ferulic acid produced by the phenylpropanoid pathway have often been attempted as the starting materials to produce vanillin, one of the most extensively used aromatic flavor compounds (25-27, 32).trans-Anethole (p-methoxy propenylbenzene), the major component present in the essential oils of anise, fennel, and star anise, is also a type of phenylpropanoid compound formed by terpene synthesis in plants (10). trans-Anethole is used commercially as a flavor substance in baked goods, candy, ice cream, chewing gum, and alcoholic beverages (21). However, there have been few research reports regarding its metabolism (8,12,21,22,31). Indeed, to date, the only two bacterial strains isolated that are known to use trans-anethole as a sole carbon source are Arthrobacter sp. strain TA13 and Pseudomonas putida JYR-1 ...

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“…[5][6][7] Numerous attempts to produce vanillin from abundantly available phenylpropanoid precursor compounds such as isoeugenol (2-methoxy-4-(1-propenyl) phenol) have been made, 3,[8][9][10][11][12][13][14][15][16][17][18][19][20] but thus far only two cloned genes have been identified as isoeugenol monooxygenases responsible for the conversion of isoeugenol to vanillin (Fig. 1A).…”

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confidence: 99%

Transcriptional Control of the Isoeugenol Monooxygenase ofPseudomonas nitroreducensJin1 inEscherichia coli

Ryu¹,

Seo²,

Ahn³

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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Biotransformation of Isoeugenol to Vanillin by a Novel Strain of Bacillus fusiformis

Abstract: A novel strain of Bacillus fusiformis, producing high amounts of vanillin from isoeugenol, was isolated from soil. Using 60% (v/v) isoeugenol as substrate and solvent and at pH 4.0, 37°C and 180 rpm, vanillin was produced at 32.5 g l )1 over 72 h. The unused isoeugenol was reusable.

Cited by 90 publications

References 10 publications

Involvement of Colonizing Bacillus Isolates in Glucovanillin Hydrolysis during the Curing of Vanilla planifolia Andrews

Involvement of Colonizing Bacillus Isolates in Glucovanillin Hydrolysis during the Curing of Vanilla planifolia Andrews

Isolation of a Gene Responsible for the Oxidation of trans -Anethole to para -Anisaldehyde by Pseudomonas putida JYR-1 and Its Expression in Escherichia coli

Transcriptional Control of the Isoeugenol Monooxygenase ofPseudomonas nitroreducensJin1 inEscherichia coli

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