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At least 19 recordsLinked to original sources
PubMed2002

Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia.

Tissue cultures of the vanilla orchid, Vanilla planifolia, produce the flavor compound vanillin (4-hydroxy-3-methoxybenzaldehyde) and vanillin precursors such as 4-hydroxybenzaldehyde. A constitutively expressed enzyme activity catalyzing chain shortening of a hydroxycinnamic acid, believed to be the first reaction specific for formation of vanilla flavor compounds, was identified in these cultures. The enzyme converts 4-coumaric acid non-oxidatively to 4-hydroxybenzaldehyde in the presence of a thiol reagent but with no co-factor requirement. Several forms of this 4-hydroxybenzaldehyde synthase (4HBS) were resolved and partially purified by a combination of hydrophobic interaction, ion exchange and gel filtration chromatography. These forms appear to be interconvertible. The unusual properties of the 4HBS, and its appearance in different protein fractions, raise questions as to its physiological role in vanillin biosynthesis in vivo.

Carbon-Carbon Lyases↗
PubMed2001

Microorganisms with a taste for vanilla: microbial ecology of traditional Indonesian vanilla curing.

The microbial ecology of traditional postharvesting processing of vanilla beans (curing) was examined using a polyphasic approach consisting of conventional cultivation, substrate utilization-based and molecular identification of isolates, and cultivation-independent community profiling by 16S ribosomal DNA based PCR-denaturing gradient gel electrophoresis. At two different locations, a batch of curing beans was monitored. In both batches a major shift in microbial communities occurred after short-term scalding of the beans in hot water. Fungi and yeast disappeared, although regrowth of fungi occurred in one batch during a period in which process conditions were temporarily not optimal. Conventional plating showed that microbial communities consisting of thermophilic and thermotolerant bacilli (mainly closely related to Bacillus subtilis, B. licheniformis, and B. smithii) developed under the high temperatures (up to 65 degrees C) that were maintained for over a week after scalding. Only small changes in the communities of culturable bacteria occurred after this period. Molecular analysis revealed that a proportion of the microbial communities could not be cultured on conventional agar medium, especially during the high-temperature period. Large differences between both batches were observed in the numbers of microorganisms, in species composition, and in the enzymatic abilities of isolated bacteria. These large differences indicate that the effects of microbial activities on the development of vanilla flavor could be different for each batch of cured vanilla beans.

Bacillus↗
PubMed2003

Localization of beta-D-glucosidase activity and glucovanillin in vanilla bean (Vanilla planifolia Andrews).

The morphology, anatomy and histology of mature green vanilla beans were examined by light and transmission electron microscopy. Beans have a triangular cross-section with a central cavity containing seeds. Each angle is lined with tubular cells, or papillae, while the cavity sides consist of placental laminae. The epicarp and endocarp are formed by one or two layers of very small cells, while the mesocarp contains large, highly vacuolarized cells, the cytoplasm being restricted to a thin layer along the cell walls. The radial distributions of glucovanillin and beta-glucosidase activity, measured on p-nitrophenyl-beta-glucopyranoside and glucovanillin, are superimposable and show how beta-glucosidase activity increases from the epicarp towards the placental zone, whereas glucovanillin is exclusively located in the placentae and papillae. Subcellular localization of beta-glucosidase activity was achieved by incubating sections of vanilla beans in a buffer containing 5-bromo-4-chloro-3-indolyl-beta-d-glucopyranoside as a substrate. Activity was observed in the cytoplasm (and/or the periplasm) of mesocarp and endocarp cells, with a more diffuse pattern observed in the papillae. A possible mechanism for the hydrolysis of glucovanillin and release of the aromatic aglycon vanillin involves the decompartmentation of cytoplasmic (and/or periplasmic) beta-glucosidase and vacuolar glucovanillin.

Benzaldehydes↗
PubMed2003

Purification and characterization of vanilla bean (Vanilla planifolia Andrews) beta-D-glucosidase.

Vanilla bean beta-D-glucosidase was purified to apparent homogeneity by successive anion exchange, hydrophobic interaction, and size-exclusion chromatography. The enzyme is a tetramer (201 kDa) made up of four identical subunits (50 kDa). The optimum pH was 6.5, and the optimum temperature was 40 degrees C at pH 7.0. K(m) values for p-nitrophenyl-beta-D-glucopyranoside and glucovanillin were 1.1 and 20.0 mM, respectively; V(max) values were 4.5 and 5.0 microkat.mg(-1). The beta-D-glucosidase was competitively inhibited by glucono-delta-lactone and 1-deoxynojirimycin, with respective K(i) values of 670 and 152 microM, and not inhibited by 2 M glucose. The beta-D-glucosidase was not inhibited by N-ethylmaleimide and DTNB and fully inhibited by 1.5-2 M 2-mercaptoethanol and 1,4-dithiothreitol. The enzyme showed decreasing activity on p-nitrophenyl-beta-D-fucopyranoside, p-nitrophenyl-beta-D-glucopyranoside, p-nitrophenyl-beta-D-galactopyranoside, and p-nitrophenyl-beta-D-xylopyranoside. The enzyme was also active on prunasin, esculin, and salicin and inactive on cellobiose, gentiobiose, amygdalin, phloridzin, indoxyl-beta-D-glucopyranoside, and quercetin-3-beta-D-glucopyranoside.

Chemical Phenomena↗
PubMed1988

Determination of coumarin as an adulterant in vanilla flavoring products by high-performance liquid chromatography.

A high-performance liquid chromatographic procedure was developed for the isolation and quantitation of coumarin from vanilla-based liquid flavorings of Mexican origin. Forty products representing fourteen different Mexican brands were assayed for coumarin, vanillin, and ethyl vanillin by the proposed method. The procedure has been adapted to the analysis of other products including domestic vanilla extracts and imitation vanilla flavorings for vanillin, ethyl vanillin, 4-hydroxybenzaldehyde and piperonal. Chromatographic retention data for thirty-seven compounds associated with vanillin and vanilla products employing two mobile phase systems are presented.

Benzaldehydes↗
PubMed1997

Effect of milk fat content on flavor perception of vanilla ice cream.

The effects of milk fat concentration on flavor perception of vanilla ice cream (with 0.5 to 10% fat) were studied by sensory analyses. The percentage of free vanillin in the ice cream was determined by HPLC. The HPLC data showed that the amount of free vanillin decreased when fat content increased. Perceptions of vanilla flavor and sweetness were evaluated by a trained panel using time-intensity methodology. No significant difference was found in sweetness perception. Among 11 time-intensity parameters for vanilla flavor perception, the panel found a significant difference only in the time required to reach maximum vanilla intensity. However, free-choice profiling and a consumer preference panel showed, respectively, that, as fat content was increased, sensory quality improved, and overall preference increased.

Animals↗
PubMed2000

Long-chain aliphatic beta-diketones from epicuticular wax of Vanilla bean species. Synthesis of nervonoylacetone.

Analysis of the neutral lipids from Vanilla fragrans and Vanilla tahitensis (Orchidaceae) without saponification resulted in the isolation and identification of a new product family in this plant: beta-dicarbonyl compounds. The compound structures are composed of a long aliphatic chain with 2,4-dicarbonyl carbons and a cis double bond at the n-9 position. They represent approximately 28% of the neutral lipids, that is, 1.5%, in immature beans, and approximately 10% of the neutral lipids, that is, 0.9%, in mature beans. Using retention indices, gas chromatography-mass spectrometry, derivatization reactions, and chemical degradation, five beta-dicarbonyl compounds have been identified including 16-pentacosene-2,4-dione, 18-heptacosene-2,4-dione, 20-nonacosene-2, 4-dione, 22-hentriacontene-2,4-dione, and 24-tritriacontene-2, 4-dione. Among them (Z)-18-heptacosene-2,4-dione, or nervonoylacetone, has been synthesized in two steps starting from nervonic acid. The major constituent, nervonoylacetone, represented 74.5% of the beta-dicarbonyl fraction. The range of these compounds has been studied in relation with bean maturity for V. fragrans and V. tahitensis species. This compound family has not been found in the leaves or stems of any of the three vanilla species studied and is markedly absent in the beans of V. madagascariensis.

Gas Chromatography-Mass Spectrometry↗
PubMed2000

Analysis of the volatile components in vanilla extracts and flavorings by solid-phase microextraction and gas chromatography.

The development and application of a solid-phase microextraction (SPME) method in the analysis of vanilla extracts and vanilla flavorings was studied. The SPME method was developed to be used in conjunction with gas chromatography mass spectrometry (GC-MS). The optimized SPME sampling parameters for the determination of the volatile components included a poly(acrylate) fiber, a 40-min sampling time at room temperature, and a 2-min desorption time. The reproducibility of the method was good, with a percent relative standard deviation between 2.5 and 6.4% for the target compounds. The data suggest that the origin of natural extracts can be readily determined from the GC profile and that differences exist between nature-identical and synthetic flavorings and the natural extracts. The method also has potential for identifying the type of vanilla extract/flavoring used to flavor food.

Flavoring Agents↗
PubMed2001

Properties of diphenolase from Vanilla planifolia (Andr.) shoot primordia cultured in vitro.

Properties of diphenolase (PPO, EC1.10.3.1) from vanilla (Vanilla planifolia Andr.) shoot primordia culture were investigated. Two pH optima of the enzyme extraction at pH 6 and 8 were found. Nevertheless, the enzymes shared the same optimum pH of activity-between pH 3 and 4. Sodium dodecyl sulfate slightly improved diphenolase extraction but caused a 3-fold increase in its specific activity. The extracts of pH 6 and 8.0 revealed three isozyme bands after polyacrylamide gel electrophoresis-two of them were similar in both extracts and two distinct. The enzyme showed high thermal stability-no loss was observed after 120 min at 50 degrees C. Diethyldithiocarbamic acid, ethylenediaminetetracetic acid disodium salt, ethylene glycol bis(beta-aminoethyl ether) N,N,N',N'-tetraacetic acid, L-ascorbic acid, dithiothreitol, glutathione (reduced), and beta-mercaptoethanol were found to be potent inhibitors of the diphenolase studied. The enzyme showed also monophenolase activity. Km and Vmax were calculated with monophenols [p-coumaric acid, 3-(p-hydroxyphenyl)propionic acid, 4-hydroxybenzyl alcohol, 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid] and with diphenols (caffeic acid, hydrocaffeic acid, chlorogenic acid, 4-methylcatechol, protocatechuic aldehyde and acid, and 3,4-dihydroxyphenylalanine). The highest Vmax was found with 4-hydroxybenzyl alcohol and the greatest affinity to protocatechuic acid, respectively-the most abundant monophenol and one of the least abundant o-diphenols in the studied Vanilla tissue.

Catechol Oxidase↗
PubMed1992

Alternate cardiovascular baseline assessment techniques: vanilla or resting baseline.

The accurate evaluation of cardiovascular reactions to psychological challenge requires stable baselines against which change can be evaluated. When more than one challenge is employed, the recovery of this baseline becomes important in order to avoid carryover effects. Resting periods, even those of 20 min or more, do not guarantee baseline stability. We compared a 20-min resting condition and a new form of baseline condition in 48 college men using video tasks as the psychological challenges. The new form was a minimally demanding color detection task, termed the "vanilla" baseline condition. A 10-min version and a 20-min version of this condition were tested. Comparisons to 10-min resting baselines were made using our prior work and values from the literature. Vanilla baseline conditions were shown to be equal to or better than resting baseline conditions using criteria of between- and within-baseline stability, amplitude and significance of responsivity, and generalizability between sessions on separate days. Ten-minute resting baselines also showed acceptable stability, questioning the value of lengthy baselines. The good performance of the 10-min vanilla baseline in initial and replication samples supported its utility for estimating baselines for many purposes.

Adolescent↗
PubMed1993

Nucleotide sequence, serology and symptomatology suggest that vanilla necrosis potyvirus is a strain of watermelon mosaic virus II.

Vanilla necrosis potyvirus (VNV) is the cause of significant losses to the South Pacific islands vanilla crop. The gene for the coat protein of VNV has been cloned and sequenced. Comparison of this gene with other potyviral coat protein sequences revealed 97% nucleotide sequence homology (98% amino acid homology) to a US isolate of watermelon mosaic virus II (WMV-II), 93% nucleotide sequence homology (96% amino acid homology) to an Australian isolate of WMV-II and 81% nucleotide sequence homology (88% amino acid homology) to soybean mosaic virus-N (SMV-N). Serological analysis, by Western blot and ELISA, confirmed the close relationship between VNV and WMV-II. Furthermore, a limited host range determination found VNV and WMV-II able to infect the same series of test plants. However, symptoms differed significantly on three test species demonstrating that VNV and WMV-II are not identical in biological properties. We suggest that VNV be renamed WMV-II (Tonga).

Amino Acid Sequence↗
PubMed1984

Unusually severe food poisoning from vanilla slices.

Thirty six people suffered from severe vomiting and diarrhoea 15 min to 3 h after eating vanilla slices from the same bakery. Five patients were admitted to hospital, and one developed unusual skin lesions after admission. Staphylococcus aureus was isolated in large numbers from vanilla slices of the same batch as those giving rise to symptoms, and from five faecal specimens obtained from affected persons. Bacillus cereus and Bacillus subtilis were also isolated from the slices. Unbaked custard provides an ideal environment for bacterial multiplication, especially when (as on this occasion) the ambient temperature is persistently high.

Adult↗
PubMed2001

Bioactive aromatic compounds from leaves and stems of Vanilla fragrans.

Alcoholic extracts of leaves and stems of Vanilla fragrans were fractionated with ethyl acetate and aqueous butanol. All three fractions of ethyl acetate, butanol, and water were screened for toxic bioactivity against mosquito larvae. The results of these experiments showed that the fractions from the ethyl acetate and butanol phases were both active in the bioassay. Bioactivity of the ethyl acetate fraction was found to be much greater than that from the butanol fraction in mosquito larvae toxicity. The water phase appeared to contain no substances that impaired mosquito larval growth. Repeated column chromatography of the ethyl acetate fraction on silica gel led to the isolation of 4-ethoxymethylphenol (1), 4-butoxymethylphenol (2), vanillin (3), 4-hydroxy-2-methoxycinnamaldehyde (4), and 3,4-dihydroxyphenylacetic acid (5). Compounds 4 and 5 were isolated from Vanilla species for the first time and 2 has not been reported to have been found in a natural form. 4-Ethoxymethylphenol (1) was the predominant compound, but 4-butoxymethylphenol (2) showed the strongest toxicity to mosquito larvae. The structures of the compounds were determined on the basis of their mass spectra and (1)H or (13)C NMR data.

Animals↗
PubMed2001

Novel chemistry of abdominal defensive glands of nymphalid butterfly Agraulis vanillae.

Abdominal defensive glands of both sexes of the Gulf fritillary butterfly, Agraulis vanillae (Linnaeus) (Nymphalidae:Heliconiinae) emit a pronounced odor when disturbed. We have identified 6-methyl-5-hepten-2-one; oleic, palmitic, and stearic esters of the corresponding alcohol 6-methyl-5-hepten-2-ol; hexadecyl acetate; 1,16-hexadecanediol diacetate; and 1,15-hexade-canediol diacetate in the glandular exudate. Since we have determined that free-flying birds or birds in a butterfly conservatory discriminate against A. vanillae as prey, we suggest that the constituents in the glands may play a defensive role against potential avian predators.

Abdomen↗
PubMed2001

Enhancement of sweetness ratings of aspartame by a vanilla odor presented either by orthonasal or retronasal routes.

When taste stimuli are presented with specific odor stimuli, the perceived intensity of taste is enhanced, a phenomenon called odor-induced taste enhancement. There is a possibility, however, that the odor substances might have stimulated the taste receptors in the oral cavity as well as odor receptors in the nasal cavity because the odor substances were dissolved in the taste solutions in some preceding studies. Schifferstein and Verlegh (1996) found that the odor-induced taste enhancement effect was not found when the subjects wore a nose clip to prevent the olfactory perception. Thus, it was suggested that the odor-induced taste enhancement did not result from the stimulation of receptors in the oral cavity. To confirm and extend their study, we presented the odor stimuli simultaneously with, but not dissolved in, the taste stimuli with a more advanced approach to stimulus presentation. The participants reported enhancement of sweetness ratings for aspartame when the taste stimuli were presented with a vanilla odor. This odor induced taste enhancement was found when the gaseous odor stimuli were presented either by the retronasal route or by the orthonasal route. There was little possibility that the vanilla odor stimulated the taste receptors during the orthonasal stimulation because the odor stimuli were presented directly into the nasal cavity. Thus, we could show that the odor-induced taste enlancement is elicited by olfactory perception. These results also suggested that there is little functional difference between retronasal and orthonasal olfaction.

Administration, Oral↗
PubMedDate not supplied

beta-Glucosidase and peroxidase stability in crude enzyme extracts from green beans of Vanilla planifolia Andrews.

The extraction method for beta-glucosidase from green vanilla beans has been studied. The effect of storage of green beans and protein extracts on beta-glucosidase and peroxidase activity was investigated: the best method, resulting in the highest enzyme activities, particularly for glucosidase, was through extraction of very fresh green beans in the presence of BisTris propane buffer at pH 8. The best method for storage of the extracts was at -80 degrees C after addition of 15% glycerol, when over 90% of initial activity was still present. Peroxidase activity did not change in frozen beans or in frozen extracts.

Orchidaceae↗
PubMed1981

[A simple method for the detection of staphylococcal enterotoxin type B in vanilla custard using the ELISA (author's transl)].

The ELISA for the detection of staphylococcal enterotoxin type B (SEB) was employed to demonstrate SEB in Dutch Vanilla custard. Due to the sensitivity of the ELISA the extraction procedure, which is necessary when the Ouchterlony test is used, can be abbreviated to a great extent. Two successive extractions at pH 7.4 and pH 4.5 followed by a concentration (1:20) was sufficient to detect 0.1 mcg SEB in 100 g custard.

Enterotoxins↗