The Incorporation of Ciliatine (2-Aminoethylphosphonic Acid) into Lipids of the Rat Liver

Four alcohols, 1-penten-3-ol, n-amylalcohol, trans-2-hexenol and one of the linalool oxides, were newly identified as the components of carbonyl-free neutral fraction of the essential oil of black tea.

On the gas chromatogram of carbonyl fraction three unknown peaks were identified with those of n-valeraldehyde, n-heptanal and trans-2-octenal.

From these results almost all main components of carbonyl and carbonyl free fractions were clarified.

Flavor change during the manufacture of black tea was investigated by gas chromatography. During withering, hexylalcohol, nerol, trans-2-hexenoic acid, trans-2-heхenol, linalool oxide (cis, furanoid), n-valeraldehyde, capronaldehyde, n-heptanal, trans-2-hexenal, trans-2-octenal, benzaldehyde, phenylacetaldehyde, n-butyric, isovaleric, n-caproic, cis-3-hexenoic and salicylic acids and o-cresol were increased, especially the former three greatly increased, while cis-2-pentenol, linalool, geraniol, benzylalcohol, phenylethanol and acetic acid diminished markedly. In the process of fermentation almost all constituents increased, especially, 1-penten-3-ol, cis-2-pentenol, benzylalcohol, trans-2-hexenal, benzaldehyde, n-caproic, cis-3-hexenoic and salicylic acids were remarkable.

On firing, most alcohols, carbonyl and phenolic compounds decreased remarkably whereas acetic, propionic and isobutyric acids greatly increased.     

Volatile Flavor of Black Tea

The volatile components extracted from fresh tea leaf, fermented leaf and black tea were analysed by gas chromatography.

Quantitative difference in the composition of essential oils was observed between fresh leaf and manufactured black tea; the former was rich in alcohols, whereas the latter in aldehydes and acids.

During fermentation process the following components mainly brought about changes: n-capronaldehyde (4.1 times after fermentation for 3hrs.), trans-2-hexen-l-al (13.2 times) and cis-3-hexenoic acid (1.2 times) increased, but n-hexylalcohol (0.7 time), cis-3-hexen-l-ol (0.7 time) and methylsalicylate (0.8 time) decreased.

These changes during fermentation were scarcely carried out in nitrogen atmosphere.     

Volatile Flavor of Black Tea

The first effluent of essential oil of black tea in the gas chromatographic analysis is important for characterizing black tea flavor. The isolation and identification of main unknown components were conducted by means of gas chromatography, and also by infrared spectra and ultraviolet spectra. Ethylacetate, ethylalcohol and β-myrcene were identified as the increasing compounds during fermentation. cis-β-Ocimene and trans-β-ocimene were also identified only in completely manufactured black tea. These three terpenoid hydrocarbons are newly found constituents of essential oil of black tea and are supposed to contribute considerably to the black tea flavor.     

棒状乳杆菌FZU63发酵对红茶汤风味品质改善的作用

乳酸菌发酵可赋予茶饮料独特的香气与滋味,且可改变其物质组成,产生益生因子等。目前,针对乳酸菌在不同发酵阶段对茶汤中风味物质形成影响的研究较少。本研究以从中国传统泡菜中筛选获得的棒状乳杆菌FZU63为发酵菌株,对不同发酵阶段红茶汤中的挥发性香气成分、还原糖、游离氨基酸、有机酸等含量的变化过程进行分析,并对发酵红茶汤的感官品质进行评价。结果表明,棒状乳杆菌FZU63以红茶汤中的葡萄糖、果糖、甘露糖和木糖作为发酵过程中的主要碳源物质。红茶汤经棒状乳杆菌FZU63发酵作用后,香气成分丰度显著增加,且主要香气组分结构发生改变,发酵红茶汤在花香、坚果香的基础上增添了水果香;此外,部分苦味氨基酸含量下降,甜味和鲜味氨基酸含量增加;并且,乳酸、苹果酸、柠檬酸等有机酸含量在发酵过程中呈现积累。同时,感官评定结果表明棒状乳杆菌FZU63发酵可改善红茶汤的感官品质,且在发酵48h后达到较优。本文系统分析了经棒状乳杆菌发酵不同阶段对红茶汤风味的影响,可为乳酸菌发酵茶饮料的品质控制与产业化应用提供理论参考。     

The importance of linoleic acid and linolenic acid as precursors of hexanal and trans-2-hexenal in black tea

During tea fermentation, linoleic acid in the neutral fat fraction,and linolenic acid in both the neutral fat and phospholipidfractions from leaves decreased. The addition of linoleic orlinolenic acid to leaf macerates during fermentation resultedin an increase in hexanal or trans-2-hexenal in the volatilefraction. Tracer experiments showed the direct conversion oflinoleic-U-¹⁴C and linolenic-U-¹⁴C acids to labeled hexanaland trans-2-hexenal, respectively, which were identified as2,4-DNPH derivatives. Further conversion of hexanal and trans-2-hexenal into hexanoicand trans-2-hexenoic acids during tea fermentation was suggestedby the increases in these compounds after the addition of hexanaland trans-2-hexenal to leaf macerates. (Received December 21, 1971; )     

Changes in lactic acid bacteria and components of Awa-bancha by anaerobic fermentation

ABSTRACT

Awa-bancha is a post-fermented tea produced in Naka and Kamikatsu, Tokushima, Japan. We investigated the lactic acid bacteria in each stage of production of Awa-bancha and evaluated the relationships with the components. Lactic acid bacteria were isolated from tea leaves cultured with de Man, Rogosa, and Sharpe (MRS) agar plates, and the species were identified by homology of the 16 S rRNA gene and multiplex polymerase chain reaction (PCR) of the recA gene to distinguish the Lactobacillus plantarum group. As a result, a variety of species were isolated from the raw tea leaves, and Lactobacillus pentosus was isolated most frequently after anaerobic fermentation. Regarding the tea leaf components, organic acids, such as lactic acid, increased, free amino acids decreased, and catechins changed owing to anaerobic fermentation. Our results suggest that the microbial flora mainly composed of L. pentosus is important in the anaerobic fermentation process for flavor formation of Awa-bancha.     

(2S)-2-Amino-5-chloro-4-hydroxy-5-hexenoic acid,a new chloroamino acid,and related compounds fromAmanita gymnopus

Combining different chromatography systems, unusual nonprotein amino acids were isolated and unequivocally identified from a small amount (less than 100 g fresh weight) ofAmanita gymnopus fruit body. Without obtaining crystals of these amino acids, on the basis of¹H-NMR determination, high resolution mass spectrometry, chlorine analysis and oxidation with L-amino acid oxidase, one of them proved to be a new chloroamino acid, (2S)-2-amino-5-chloro-4-hydroxy-5-hexenoic acid (G2). The other three were (2S)-2-amino-5-hexenoic acid (G1), (2S)-2-amino-4,5-hexadienoic acid (G3) and (2S)-2-amino-5-hexynoic acid (G4). Amino acid (G1) was also encountered for the first time in natural products. Amino acid (G3) has been reported from several kinds of fungi belonging toAmanita, subgenusLepidella. The occurrence of amino acid (G4) was already reported fromCortinarius claricolor.Part 23 in the series Biochemical studies of nitrogen compounds in fungi. Part 22, Hatanaka, S. I. et al. 1985. Trans. Mycol. Soc. Japan26: 61–68.     

Flavor of Black Tea

Intermediate and high boiling neutral compounds in the aroma concentrate from black tea were isolated by fractional distillation, silica-gel column chromatography and gas chromatography.

Identification of the compounds was verified by the agreement of IR and mass spectra as well as gas chromatographic data with those of authentic compounds.

Eleven compounds; α-muurolene, δ-cadinene, furfuryl alcohol, methyl phenyl carbinol, cadinenol, geranial, pyrrole-2-aldehyde, benzyl formate, phenylethyl formate, cis-3-hexenyl benzoate and indole, were newly identified as constituents of black tea aroma and ten known components; α-terpineol, 3, 7-dimethyl-l, 5, 7-octatrien-3-ol, trans, trans-2, 4-decadienal, 2-phenyl-2-butenal, α- and β-ionone, cis-jasmone, theaspirone, lactone of 2-hydroxy-2, 6, 6-trimethylcyclohexylidene-l-acetic acid and phenylacetonitrile were confirmed. The geometric structure of theaspirone in tea aroma was determined as the cis-form.     

Nouvelle Synthèse de l’α-Damascone

The gardenia absolute was separated into basic, phenolic, acidic, lactonic and neutral fractions and analysed by using GC, combined GC-MS, IR and NMR. A total of 130 components was identified. Among them, the characteristic constituents responsible for the sweet-green odor of this flower were jasmin lactone, cis-3-hexenol, esters of cis-3-hexenol, cis-3-hexenoic acid and tiglic acid.     

Constituents and Composition of Steam Volatile Aroma from Ceylon Tea

The constituents of steam volatile aroma, which were responsible for topnote of Ceylon tea aroma, were identified. A total of 57 compounds were identified, of which 10 (ter-pinolene, n-nonanal, trans-2-pentenal, trans-3-octen-2-one, 6-methyl-3,5-heptadien-2-one, n-nonanol, cis-3-hexenylbutyrate, cis-3-hexenylcaproate, α-terpinylacetate and nerylacetate) had not previously been reported as associated with aroma of black tea. Approximate composition of topnote aroma from Ceylon flavory tea was also determined.     

Carboxylic Acids in Cultured Broth of Sporobolomyces odorus

Carboxylic acids found in the cultured broth of Sporobolomyces odorus AHU 3246 which produces γ-lactones as principles of the aromatic flavor, were analyzed. The concentrate of methylated acids was steam-distilled and in the residue, succinic acid, nonanedioic acid (azelaic acid), undecanedioic acid and 2-hydroxy-3-phenylpropionic acid (β-phenyllactic acid) were identified as their methyl esters by GLC and spectroscopic methods. Phthalic acid and its mono-n-butyl ester were also found, but these compounds were thought to arise from di-n-butyl phthalate, one of impurities of deionized water.     

A chlorohydrin amino acid from Amanita abrupta

A new amino acid, (2S,4Z)-2-amino-5-chloro-6-hydroxy-4-hexenoic acid, has been isolated from Amanita abrupta. Three other unusual amino acids were also isolated from the same fungus.     

Occurrence of Free Base of Phytosphingosine in Candida intermedia (IFO 0761)

The aroma concentrates from Vietnamese green tea and lotus tea were prepared and analyzed. Characterization of the components were carried out using coupled gas chromatography and mass spectrometry and infrared spectrometry, besides gas chromatographic retention data.

Anethole and 1,4-dimethoxybenzene have been identified for the first time as the flavor constituents in green tea. Linalool, two linalooloxides (cis and trans, five membered), 3,7-dimethyl-1,5,7-octatriene-3-ol, 2,5 (or 2,6)-dimethylpyrazine and 1-ethyl-2-formylpyrrole were the predominant components in Vietnamese green tea.

1,4-Dimethoxybenzene has been identified as the main component in lotus tea. The compound was also isolated from both dried and fresh lotus pollen.     

Fungal Reduction of C6 α,β-Unsaturated Carboxylic Acids

The metabolism of sorbic acid (trans-2,trans-4-hexadienoic acid) and its related compounds by Mucor sp. A-73 was investigated. Sorbic acid was reduced by this fungus to trans-4-hexenol (more than 90% yield). In a series of hexamonoenoic acids, carboxyl groups and α,β-double bond were reduced, but β,γand γ,δ double bonds were hardly reduced. The reduction of cis-2-hexenoic acid was slower than that of the corresponding trans isomer. Sorbic alcohol, one of α,β-unsaturated alcohols, was converted well to trans-4-hexenol by the fungus. These results showed that this fungus could carry out two independent reductions: (i) carboxyl group→alcohol, (ii) α,β-unsaturated alcohol→αβ-saturated one. Furthermore, α,β-unsaturated alcohols were temporarily detected in the course of fungal reductions of some α,β-unsaturated acids. The fact suggested that the reduction of α,β-unsaturated acids to α,β-saturated alcohols was initiated by the reaction (i) and followed by (ii). The biological hydrogenation of α,β-unsaturated alcohols is a new reaction.     

The characteristic smell emitted from two scale insects,Ceroplastes japonicus and Ceroplastes rubens

ABSTRACT

The volatile components emitted from two scale insects, Ceroplastes japonicus and Ceroplastes rubens, were identified using GC–MS analysis. The major volatile components of the solvent extract from C. japonicus were α-humulene (35.8%) and δ-cadinene (17.0%), while those of C. rubens were β-selinene (10.3%) and β-elemene (5.1%). In GC/olfactometry, linalool, butyric acid, 3-methylbutyric acid, 2-methylbutyric acid, and vanillin were identified as the odor-active components of the extract from C. japonicus, in addition to trace amounts of trans-4,5-epoxy-(2E)-decenal, 4-methyl-(3E)-hexenoic acid, and phenylacetic acid. With regard to C. rubens, trans-4,5-epoxy-(2E)-decenal, 3-methylbutyric acid, and phenylacetic acid were identified as the odor-active components. Besides, decan-1,4-olide (γ-decalactone) with milky cherry-like note and 3-hydroxy-4,5-dimethylfuran-2(5H)-one (sotolone) with brown sugar-like note were also detected as the characteristic cherry-like sweet-and-sour note of these two scale insects.     

Chemical Studies on Components of Dried Bonito, “Katsuobushi”

The flavor concentrate obtained by the extraction of “Katsuobushi” of bonito (Katsuwonus pelamis) with 80% ethanol and by the subsequent steam distillation of the extract was fractionated by the usual method and the resulting neutral, non-carbonyl oxygenated fraction was investigated by gas chromatography. The following components were tentatively identified: 2-pentanol and 2-methyl-1-heptanol as free alcohols, and 4 alcohols of n- and isobutanol, n-pentanol and n-dodecanol and 9 carboxylic acids of propanoic, n-butanoic, n-pentanoic, n-octanoic, n-nonanoic n-decanoic, n-dodecanoic, n-tetradecanoic and n-hexadecanoic acid as the constituents of esters. A constituent alcohol existing in the largest amount was isolated by gas chromatography and identified as 2-methyl-1-heptanol by elemental analysis, NMR, IR, and MS. A constituent acid existing in large amount was also isolated and investigated similarly, and the structure was partially estimated. 2-Methyl-1-heptanol holds a fresh woody aroma and seems to have a major effect on “Katsuobushi” flavor.     

Flavor of Black Tea

The neutral fraction of the essential oils from three kinds of black tea (same samples as described in the previous paper,¹⁾ i.e., Assam, Shan and Benihomare) was separated into carbonyl and carbonyl-free fractions and analysed by gas chromatography. On the basis of relative retentions and aroma of effluents with the references of the chromatographic data obtained by the previous works,^2–4) the major alcohols were found to be cis-2-pentenol, n-hexanol, cis-3-hexen-1-ol, three isomers of linalooloxide, linalool, nerol, geraniol, benzylalcohol, and phenylethylalcohol. In the carbonyl fraction, phenylacetaldehyde was newly identified, and besides it, the presence of iso- and n-butyr-, iso- and n-valer- aldehyde, methylethylketone, trans-2-hexenal, benzaldehyde were recognized. There were no differences in the components among three kinds of black tea, but the relative quantity of each component in the essential oil was different among three varieties.     

Volatile Flavor Components of Kumazasa (Sasa albo-marginata)

The volatile flavor components of Kumazasa (Sasa albo-marginata) were studied by headspace and steam distillation analyses. Thirty nine and 90 components were identified in the headspace and steam distillation concentrate respectively by GC and GC-MS. The identified components include 7 hydrocarbons, 23 alcohols, 14 aldehydes, 8 ketones, 17 phenols and 14 acids.

The components which are believed to contribute to the characteristic flavor of Kumazasa are deduced to be: 1-penten-3-ol, trans-2-hexenal, 1-hexanol, cis-3-hexen-1-ol, cyclohexanol, α-ter-pineol, 4-octanolide and β-ionone.     

Formation of Aldehyde Flavor (n-hexanal, 3Z-nonenal and 2E-nonenal) in the Brown Alga, Laminaria Angustata

2E-Nonenal and n-hexanal are the major and minor flavor compounds in the edible brown alga, Laminaria angustata, respectively. They are believed to characterize the flavor of this alga. However the metabolism of the two compounds is not precisely known. The pathways were clarified by elucidation of the intermediate structure through purification of the intermediate compounds from an enzymatic reaction and identification using HPLC and GC-MS techniques. Formation of n-hexanal, 3Z-nonenal and 2E-nonenal are proposed to be via two cascades from unsaturated fatty acids. They are C18:2(n-6), linoleic acid cascade and C20:4(n-6), arachidonic acid cascade through their hydroperoxides as intermediates by the lipoxygenase/fatty acid hydroperoxide lyase pathway.     

Muscle fat composition of pheasants (<Emphasis Type="Italic">Phasianus colchicus)</Emphasis>, wild ducks (<Emphasis Type="Italic">Anas platyrhynchos</Emphasis>) and black coots (<Emphasis Type="Italic">Fulica atra</Emphasis>)

The aim of this investigation was to characterise the fatty acid composition within intramuscular fat (IMF) of two muscles (breast and thigh) from 28 pheasants, ten wild ducks and 27 black coots from Slovakia. A high variability for all single fatty acids (FA) and the total fat concentration in muscles of wild birds was identified. Black coots deposited the highest fat in breast muscle whereas wild ducks and pheasants accumulated more lipids in thigh muscle. In general, the content of polyunsaturated fatty acids (PUFA) of the IMF in wild bird muscles was high, and the saturated FA concentration was lower compared with muscles of domestic farm animals. The ratio between PUFA and saturated fatty acids (PSQ) ranked between 0.6 and 1.2, and the ratio of n-6/n-3 fatty acid was favourably low in black coot and wild pheasants (3.2 and 2.9, respectively). Farmed pheasants had increased IMF and more saturated and n-6 fatty acids deposited in thigh muscle but not in breast muscle.