Tannins are plant defense substances that exhibit a strong astringent taste and precipitate proteins, leading to the inhibition of protein functions; however, owing to their relatively low toxicity, tannins must be accumulated in high concentrations in cell vacuoles. Therefore, the solubility of tannins is crucial for their functions. In this review, the structure and reactions of tannins related to solubility; insolubilization of persimmon proanthocyanidins on fruit ripening; pigment formation from cinnamon procyanidins by reaction with cinnamaldehyde in case of wounding; and insolubilization of ellagitannins in chestnut wood is discussed. In addition, the development of functional polyphenols including oil-soluble tea catechins is introduced.
We designed and synthesized a series of N,N-disubstituted allylic amine type aminophosphines 2, 3 and 4, which are derivatives of chiral ligands 1. Aminophosphines 2–4 (except 2a) exist in C(aryl)–N(amine) bond axial chirality by chiral HPLC analysis. Both enantiomeric isomers of 4b were successfully obtained in an enantiomerically pure form. We demonstrated that 1a, 1b, and 4b can be used as effective chiral ligands for the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate with malonates in high enantioselectivities (up to 90% ee).
An essential oil from dried “wakame” (Undaria pinnatifida), prepared by a simultaneous distillation extraction method, was analyzed by GC-MS, indicating the presence of one major component of volatiles. The volatile component was identified as (6Z,9Z,12Z,15Z,18Z)-1,6,9,12,15,18-henicosahexaene by comparison with the GC-MS and NMR spectra of synthetic. The henicosahexaene showed a subtly marine aroma. (6Z,9Z,12Z,15Z)-1,6,9,12,15-Henicosapentaene was also detected as a minor polyene in the essential oils. It was suggested that these polyenes contribute to the characteristic aroma of the dried wakame.
A highly efficient and simple method for the synthesis of 2-alkylbenzothiazoles through the condensation of 2-aminothiophenol and aliphatic aldehydes in the presence of active carbon/silica gel is described. The reaction proceeded under solvent-free and microwave irradiation to afford 2-alkylbenzothiazoles in high yields. This method was extended to the synthesis of bile acid derivatives containing a benzothiazole ring and obtained the desired products in high yields. The anti-inflammatory activity and cytotoxicity of the newly synthesized benzothiazole derivatives of bile acid were tested; the results showed that anti-inflammatory activities of all tested compounds tested were higher than that of standard drugs, such as indomethacin.
A volatile compound was isolated from the fruit of Habanero pepper (Capsicum chinense) and related varieties and identified as 6-methyl-(E)-4-heptenyl 3-methylbutyrate by 1H and 13C NMR spectroscopy and two-dimensional NMR experiments, including HMQC, HMBC, and 1H-1H COSY. The compound has a retention index of 1387 and is one of the major volatile compounds in Habanero pepper. This compound would be useful as a new flavor.
The present study provides valuable data that the herbal water byproduct of Japanese peppermint, produced during the steam distillation extraction of an essential oil, can be utilized as an antibacterial agent. The major ingredient in the herbal water from Japanese peppermint ‘Hokuto’ was menthol, with a concentration close to its water solubility. The herbal water produced showed excellent antibacterial efficacy against typical gram-negative and gram-positive bacterial strains of Escherichia coli and Staphylococcus aureus, respectively, and the antibacterial efficacy was maintained even when the herbal water was diluted up to an appropriate concentration of 50%. The efficacy of the herbal water against E. coli was higher than that against S. aureus, which is likely because of the difference in the efficacy of menthol against these two different bacterial strains. The excellent antibacterial efficacy of the herbal water is mainly attributed to the function of menthol, while other trace ingredients also contributed to the antibacterial efficacy. The Japanese peppermint herbal water byproduct, generally treated as industrial waste and disposed, can be easily commercialized as an antibacterial agent if efforts are made to maintain a constant menthol concentration throughout the steam distillation essential oil extraction process.
Terpene synthase (TPS) genes were isolated and functionally characterized from three traditional edible plants, Acanthopanax sciadophylloides (“Koshiabura”) and Acanthopanax sieboldianus (“Himeukogi”), belonging to the family Araliaceae, and Curcuma zedoaria (zedoary, “Gajutsu”), belonging to the family Zingiberaceae. These plants emit characteristic fragrances and are used for traditional foods and folk medicines. From their fragrant tissues, i.e., sprouts of Araliaceae plants and developing rhizomes of zedoary, total RNAs were extracted and reverse transcribed. The resultant cDNAs were used for degenerate PCR followed by rapid amplification of cDNA ends. From the contig sequences obtained, full-length Tps genes were amplified by PCR with newly synthesized primer sets. The isolated full-length genes were introduced into engineered Escherichia coli cells, which can utilize acetoacetate to synthesize farnesyl diphosphate, the substrate for TPSs, through the mevalonate pathway. TPS products synthesized in the transformed E. coli cells were analysed by gas chromatography-mass spectrometry, nuclear magnetic resonance, and optical rotation. Consequently, the isolated Tps genes were found to encode β-caryophyllene synthase, germacrene D synthase, linalool/(3S)-(+)-nerolidol synthase, β-eudesmol synthase, and germacrene B synthase. These results lead us to expect that some of the effective ingredients in folk medicines are volatile terpenes and that intake of traditional foods including these edible plants would have some positive effects on our health.
Organicpigment, 2-Methyl-3-(4-fluorophenylthio)-1,4-naphthalenedione (2), that is a new Vitamin K derivative bearing a fluorine group, did not show any polymorphism disregard of three different solvents. For comparison, its naphthoquinone analogue with a bromine group (1) showed clearly polymorphism susceptible to these solvents.
Biotransformation of (+)- and (-)-carvone (1 and 2) by the larvae of common cutworm (Spodoptera litura) has been investigated. (+)-Carvone was transformed to (+)-(4S)-10-hydroxycarvone (1-1), (+)-(4S)-7- hydroxycarvone (1-2), and (-)-(4S)-8,9-dihydroxy-8,9-dihydrocarvone (1-3). (-)-Carvone (2) was transformed to (-)-(4R)-10-hydroxycarvone (2-1), (-)-(4R)-7-hydroxycarvone (2-2), (+)-(4R)-8,9-dihydroxy-8,9- dihydrocarvone (2-3), and (-)-(2R,4R)-10-hydroxycarveol (2-4). The results indicate that the main metabolic reaction of carvones by S. litura larvae is oxidation at vinyl group (C-8 and C-9).
Carotenoids of the rosary goby Gymnogobius castaneus (juzukakehaze in Japanese) were investigated. A new acetylenic carotenoid, (3R,3’R,6’S)-7,8-didehydro-β,ε-carotene-3,3’-diol (1), named 6’-epimonadoxanthin, was isolated along with 18 known carotenoids. The structure of 6’-epimonadoxanthin was determined by UV-VIS, ESI-TOF MS, 1H-NMR, and CD spectral data. The metabolic pathway from diatoxanthin to 6’-epimonadoxanthin is also discussed.
The volatile components of the Tahitian liverwort Cyathodium foetidissimum was analyzed using headspace solid phase micro-extraction (SPME) and GC-MS. Three volatile components, 4-methoxystyrene (24.4%), 3,4-dimethoxystyrene (28.7%), and skatole (15.9%) were identified as the major components from the fresh C. foetidissimum, along with several aliphatic aldehydes, n-octanal, n-nonanal, and n-decanal. However, (E)-2-nonenal recognized as aged malodor was not identified. In GC-O analysis, 2-aminoacetophenone was detected as one of the minor components with a strong aging note. In fact, C. foetidissimum showed the characteristic aging odor reminiscent the damp smell from old chest of drawers, or the civet like note with very strong feces and urine odor. The mixture consisted of 4-methoxystyrene, 3,4-dimethoxystyrene, and skatole in the detected ratio showed the sedative effect on CNV (contingent negative variation) measurement.
The seed oil of andiroba (Carapa guianensis, Meliaceae) was found to promote collagen synthesis in normal human dermal fibroblasts. To characterize the active constituents of this oil, the collagen synthesis-promoting activities of 10 principal limonoid constituents, gedunin (1), 6α-acetoxygedunin (2), 7-deacetoxy-7-oxogedunin (3), 7-deacetoxy-7α-hydroxygedunin (4), andirolide H (5), 6α-hydroxygedunin (6), methyl angolensate (7), 17β-hydroxyazadiradione (8), and carapanosides C (9) and R (10), were examined. Among them, 1–4, 6, 7, and 9 were found to significantly promote collagen synthesis without cytotoxicity at the effective concentrations.
Herein, to achieve individual and concomitant quantifications of phospholipid classes, an absolute quantification 31P NMR method using an internal standard was examined. Phospholipid standards and dietary foods were dispersed to prepare test solutions in an anionic surfactant (sodium cholate) solution containing EDTA, as a modification based on a reported method. Each phospholipid class showed a reproducible chemical shift at a near-neutral test solution pH of 6.90±0.04 and temperature of 30.0±0.1°C. The quantity of synthetic phosphatidylcholine measured using 31P NMR was consistent with that measured by 1H NMR using an internal standard. As the principal phospholipid class of soybean and egg yolk lecithin is phosphatidylcholine, the measurement conditions of 31P NMR (pulse interval time and number of scans) were optimized such that minor phospholipids, including lysophospholipids, also present in lecithin could be quantified simultaneously. Phospholipid classes in commercial polar lipid samples derived from porcine brain, yeast, and soybean were individually quantified using the above conditions. Using phosphoserine as the internal standard material allowed the absolute molar quantity of the phospholipid class to be precisely determined with traceability to the SI. The determined molar amounts of phospholipid classes were then translated to the weight amount by assuming that each phospholipid class contained two stearic acid molecules as the constituent fatty acid. The calculated total contents of each phospholipid class by 31P NMR were in good agreement with those obtained by molybdenum blue colorimetry. Furthermore, the quantitative values of the principal phospholipid classes in the polar lipid samples obtained by 31P NMR corresponded in a broad view, however, was more informative for the separation of individual phospholipid species rather than the quantitative 2D thin-layer chromatography.
The chemical characteristics, rheological properties and sensory evaluation of nine different brands of the sesame pastes were investigated. The sesame pastes showed a significant difference for the crude fat, protein, crude fibre, total sugars, total ash, moisture content, and acid values (p < 0.05). The fat content ranged from 51.80% to 61.56%, and the protein content varied between 16.08% and 18.97%. All sesame paste samples are pseudoplastic materials. The flow indexes lied between 0.67 and 0.81 for the tested sesame pastes (p > 0.05). The consistency coefficient of the different sesame paste brands varied significantly (p < 0.05), ranging from 4.48 to 24.21 Pa・sn, indicating that the consistency coefficient is a more sensitive parameter for measuring the flow behaviour of foodstuff. The areas of the hysteresis loops of the white-sesame paste of “Haoweisi” brand and the black-sesame paste of “A Yimeng couple” brand were higher than the other sesame pastes, indicating that these two samples were difficult to be restored to their original structures and such restoration required a longer time. Both Storage modulus (G′) and loss modulus (G″) of the sesame pastes increased with increasing frequency, and G′ values were greater than the G″ values, exhibiting the typical properties of the viscoelastic solid, the results may provide the valuable reference for choosing the sesame pastes as the spreadable butters or salad dressings, and for further processing.
This study used a rice bran oil solid fat fraction (RBOSF) to produce cocoa butter alternatives via interesterification reaction catalyzed by immobilized lipase (Lipozyme® RM IM) in hexane. Effects of reaction time (6, 12, and 18 h), temperature (55, 60, and 65°C), mole ratios of 3 substrates [RBOSF:palm olein:C18:0 donors (1:1:2, 1:2:3, and 1:2:6)] were determined. The substrate system was dissolved in 3 mL of hexane and 10% of lipase was added. Two sources of C18:0 donors, stearic acid (SAd) and ethyl stearate (ESd) were used. Pancreatic lipase – catalyzed sn-2 positional analysis was also performed on both substrates and structured lipids (interesterification products). Structured lipids (SL) were analyzed by gas – liquid chromatography (G40.35LC) for fatty acid composition. Major fatty acids of RBOSF were C18:1, oleic acid (OA, 41.15±0.01%), C18:2, linoleic acid (LA, 30.05±0.01%) and C16:0, palmitic acid (PA, 22.64±0.01%), respectively. A commercial raw cocoa butter (CB) contained C18:0, stearic acid (SA, 33.13±0.04%), OA (32.52±0.03%), and PA (28.90±0.01%), respectively. Fatty acids at sn-2 position of RBOSF were OA (46.52±0.63%) and LA (42.98±1.1%), while major fatty acid at sn-2 position of CB was OA (85.24±1.22%). The RBOSF had low SA (2.40±0.01%) compared to CB (33.13±0.04%). The content of OA (46.52±0.63%) at sn-2 position in RBOSF was half of that found in CB (85.24±1.22%). Optimal reaction was 1:2:6 mole ratio of the substrate (RBOSF:PO:SAd), at 65°C for 12 h. Fatty acid compositions of the SL were 31.72±0.99% SA, 30.91±0.53% LA, 23.18±0.32% OA, and 13.26±0.34% PA, respectively. Fatty acids at sn-2 position of the SL were 53.72±4.21% OA, 25.11±3.69% LA, 14.18±1.58% PA, and 6.99±0.02% SA, respectively. DSC curves showed the melting point of CB at 20.94°C, while those of the SL were 14.15 and 40.35°C, respectively. The melting completion temperature (Tmc) of CB was 25.5°C while that of SL was 43.9°C, respectively.
Bacillus licheniformis NBRC 104464 produces a cyclic lipopeptide different from surfactin. After we performed liquid chromatography fractionation and purification, we used structural analyses to identify the cyclic lipopeptide as lichenysin. Surface tension measurements of lichenysin sodium salt in water yielded a critical micelle concentration (CMC) of 1.0×10–5 M. The surface tension at the CMC was 28.9 mN/m. Comparative analysis of Ca2+-influenced micellar aggregation of lichenysin and surfactin revealed that the formation rate of the lichenysin-Ca2+ complex aggregate remained low up to a [Ca2+]/[lichenysin] molar ratio of 80, whereas the surfactin-Ca2+ complex formed micellar aggregates at the same molar ratio. Further excessive addition of Ca2+ to the micellar solution of lichenysin induced higher turbidity than surfactin.
Nuts-enriched diets were shown to bear beneficial effects for human’s health. Among nuts, hazelnut plays a major role in human nutrition and health because of its unique fatty acid composition (predominantly MUFA), fat soluble bioactives (tocopherols and phytosterols), vitamins (vitamin E), essential minerals (selenium), essential amino acids, antioxidant phenolics (caffeic acid), dietary fiber (soluble form), and bioactive phtytochemicals. The current study was designed to explore the cellular effects of two particular hazelnut strains (Ordu and Tonda).
Four hazelnut oils were obtained from 2 common strains (Ordu hazelnut oil, Ordu cuticle oil, Tonda “gentile” hazelnut oil, Tonda “gentile” cuticle oil). The metabolic and nutritional effects of the four hazelnut oils were assessed using an in vitro model of mouse myoblasts, identifying the intracellular mechanisms involved in muscle differentiation and in the modulation of specific muscle genes.
We demonstrated that hazelnut oils induced morphological changes in neo-formed myotubes increasing myotubes size. In particular, the diversified effects of the hazelnuts and cuticle oils on muscle fibres shape (on length and diameter respectively) determine a diversified pattern of action on elongation or hypertrophy of the muscle fibres. Furthermore, hazelnut oils regulate different pathways associated with myoblasts growth and development, stimulate signal transduction, and activate cell commitment and differentiation. The present results provide evidence that hazelnut oils may affect skeletal muscle growth and differentiation, constituting the proof of principle for the future development of novel foods and integrators.
A microwave-assisted hydrodistillation (MAHD) method was investigated for extraction of essential oils from lavender. The essential oil extracts at optimized MAHD conditions was compared with hydrodistillation (HD). Response surface methodology coupled with Box-Behnken design was applied to optimize the parameters for MAHD. The optimized MAHD conditions were 500 W microwave power, 17 mL/g liquid-to-solid ratio and 40 min microwave time. The ANOVA results revealed that microwave time had the greatest impact on the essential oil yield followed by liquid-to-solid ratio and microwave power. Under the MAHD optimized conditions, the essential oil yield was 3.19%, approximating the predicted yield (3.20%). MAHD was superior in terms of saving energy and extraction time (40 min, compared to 120 min in HD). The essential oil analyzed by GC-MS, presented 39 compounds constituting 98.37% and 97.51% of the essential oils obtained through MAHD and HD, respectively. No obvious differences were found in composition between MAHD oil and HD oil. Antimicrobial study showed that the lavender essential oil exhibited broad-spectrum antibacterial activity and the MAHD oil showed a higher antimicrobial activity than the HD oil. This study revealed that MAHD could be a good method for extracting essential oil in lavender and other aromatic plants.
Several studies have shown that cadmium (Cd) induces nephrotoxicity and many plant foods phytochemicals have been found useful but their possible mechanism of action still remains unexplored. Hence, this study aimed to investigate the nephroprotective effect of essential oils from Nigeria ginger and turmeric rhizomes in cadmium-treated rats by examining their effect on renal function biomarkers (creatinine, urea and BUN), inflammatory cytokines (IL-6, IL-10 and TNF-Alpha) and renal adenosine deaminase (ADA) activity. The result revealed that essential oils from ginger and turmeric rhizomes exert anti-inflammatory effect by preventing alterations of renal function markers and cytokines (IL-6, IL-10 and TNF-Alpha) levels in Cd-treated rats. In addition, the essential oils inhibited renal ADA activity in Cdtreated rats. In conclusion, inhibition of ADA activity and modulation of inflammatory cytokines could be suggested as the possible mechanism of action by which essential oils from ginger and turmeric rhizomes exert their nephroprotective activities.
We investigated the pigments in Thai purple rice using electron paramagnetic resonance (EPR), X-band (9 GHz) EPR imaging (EPRI), and HPLC. The location and spatial distribution of the paramagnetic species in purple and white rice were determined by EPR and EPRI. EPR primarily detected three paramagnetic species in purple rice, which were identified as stable radicals, Mn2+, and Fe3+ based on the gvalues and hyperfine components of the EPR signals. Subsequent noninvasive two-dimensional (2D) EPRI revealed that these stable radicals are primarily located in the pigmented region of purple rice, while very few radicals were observed in the interior of the rice. HPLC revealed that the major compounds were cyanidin-3-O-glucoside and peonidin-3-O-glucoside. Scavenging activities, EPR, and EPR imaging results indicate that the stable radicals contain the radical state of anthocyanins and are mostly found within the pigmented embryo region of purple rice. They could be either associated with scavenging activities or could be one of the products of their oxidative decomposition.
Abdominal aortic aneurysm (AAA) is a common disease among the elderly. Recently, proprotein convertase subtilisin/kexin type 9 (PCSK9) inhibitors have been indicated as useful therapeutic tools for the treatment of cardiovascular diseases. The aim of this study was to elucidate the role of PCSK9 in the pathogenesis of AAA. We used fluorescence immunohistochemistry to assess the expression of PCSK9 in aortic tissues resected from 24 patients with AAA. Histological examination showed that PCSK9 expression in the adventitia region of the aneurysms was decreased in AAA samples. In the same region, the expression of CD36 increased. We hypothesized that CD36 expression might upregulate the transport of fatty acids into cells such as the adipocytes, and subsequently cause degradation of the adventitia in the aortic wall, contributing to AAA development.