The approximate rates and stoichiometry of the reaction of excess potassium 2-thexyl-1,3,2-dioxaborinane hydride(KTDBNH) with 55 selected compounds containing representative functional groups under standardized conditions (tetrahydrofuran, TEX>$0^{\circ}C$, reagent : compound=4 : 1) was examined in order to define the characteristics of the reagent for selective reductions. Benzyl alcohol and phenol evolve hydrogen immediately. However, primary, secondary and tertiary alcohols evolve hydrogen slowly, and the rate of hydrogen evolution is in order of $1^{\circ}$> $2^{\circ}$> $3^{\circ}$. n-Hexylamine is inert toward the reagent, whereas the thiols examined evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to give the corresponding alcohols. Cinnamaldehyde is rapidly reduced to cinnamyl alcohol, and further reduction is slow under these conditions. The reaction with p-benzoquinone dose not show a clean reduction, but anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol. Carboxylic acids liberate hydrogen immediately, further reduction is very slow. Cyclic anhydrides slowly consume 2 equiv of hydride, corresponding to reduction to the caboxylic acid and alcohol stages. Acid chlorides, esters, and lactones are rapidly and quantitatively reduced to the corresponding carbinols. Epoxides consume 1 equiv hydride slowly. Primary amides evolve 1 equiv of hydrogen readily, but further reduction is slow. Tertiary amides are also reduced slowly. Both aliphatic and aromatic nitriles consume 1 equiv of hydride rapidly, but further hydride uptake is slow. Analysis of the reaction mixture with 2,4-dinitrophenylhydrazine yields 64% of caproaldehyde and 87% of benzaldehyde, respectively. 1-Nitropropane utilizes 2 equiv of hydride, one for hydrogen evolution and the other for reduction. Other nitrogen compounds examined are also reduced slowly. Cyclohexanone oxime undergoes slow reduction to N-cyclohexylhydroxyamine. Pyridine ring is slowly attacked. Disulfides examined are reduced readily to the correponding thiols with rapid evolution of 1 equiv hydrogen. Dimethyl sulfoxide is reduced slowly to dimethyl sulfide, whereas the reduction of diphenyl sulfone is very slow. Sulfonic acids only liberate hydrogen quantitatively without any reduction. Finally, cyclohexyl tosylate is inert to this reagent. Consequently, potassium 2-thexyl-1,3,2-dioxaborinane hydride, a monoalkyldialkoxyborohydride, shows a unique reducing characteristics. The reducing power of this reagent exists somewhere between trialkylborohydrides and trialkoxyborohydride. Therefore, the reagent should find a useful application in organic synthesis, especially in the field of selective reduction.
Rhizomes of the common reed (Phragmites communis Trin.) were incubated for three days in the dark. Methanol extract of the shoots was thin layer chromatographed with several solvent systems and visualized with five reagents. The results may be summarized as follows: 1. Serotonin, tryptophan, and tryptamine were identified by cochromatography with the respective authentic compounds. Bufotenine, N-methylserotonin, and N,N-dimethyltryptamine were tentatively identified by their Rf values and colour reactions. The presence of skatole and gramine was suggested. 2. It was esteemed that the common reed might have an active methylation/hydroxylation system of indole compounds at least for a period of time. 3. The presently devised 'overlap' thin layer chromatographic technique may be a useful tool for the identification of a compound whose Rf value was diverse from that of the authentic one by the interferance containing in a sample material.
A gas chromatography/mass spectrometric (GC/MS) method has been developed for the determination of trace mono-n-butyltin (MBT), di-n-butyltin (DBT), and tri-n-butyltin (TBT) compounds in sediments. Samples were extracted by 10% acetic acid in methanol containing 0.03% tropolone and were then derivatized for GC/MS analysis. Ethylation by sodium tetraethylborate and phenylation by sodium tetraphenylborate were evaluated as a derivatization reaction of the organotins in sample extract. n-Hexane was added into reaction media in the beginning of the reaction for the continuous extraction of derivatized organotins. Ethylation requires less than 2 hours to get proper derivatization yields for MBT, DBT, and TBT altogether and produces relatively low amounts of side reaction products. Compared to ethylation, phenylation requires much longer time but provides relatively lower yield and produces considerable amounts of side reaction products. Therefore, the ethylation reaction was applied for the analysis of organotin compounds in sediment. An isotope dilution mass spectrometric (IDMS) method based on GC/MS has been applied to the accurate determination of DBT compounds in the sediments. The IDMS results from the analyses of sediment samples showed a reasonable repeatability and a good agreement with the values obtained by IDMS based on liquid chromatography/induced coupled plasma/mass spectrometry.
Rho Ho Sik;Baek Heung Soo;Kim Sujong;Kim Sunam;Kim Duck Hee;Chang Ih Seop;Lee Ok-Sub
Journal of the Society of Cosmetic Scientists of Korea
/
v.30
no.3
s.47
/
pp.405-408
/
2004
Several hydroxamic acid derivatives are synthesized to observe retinoidal effect and transactivation potential for $RAR{\alpha}/{\gamma]$ is screened. Among the synthesized compounds, N-(4-N-hydroxycarbamoyl )phenyl) [4-(tert-butyl )phenyl] carboxamide (2f) showed the best compatibility for potent $RAR{\alpha}/{\gamma].$ The acidic hydroxy of hydroxamic acid was easily deprotonated to form an enolate. A formed enolate has a similar role like that of all-trans-retinoic acid. This is the first example of the hydroxamic acid derivative with retinoidal activity. The retinoidal activity of 2f was further confirmed by enhancing activity for the expression of retinoid-responsive genes. To evaluate the possibility for anti.-aging agent, effect on the expression of MMP-1 was measured comparing with all-trans-retinoic acid and retinol. At 10 uM treatment, compound 2f inhibited the expression of MMP-1. These results suggest that new hydroxamic acid derivative 2f could be used as a promising anti-aging agent.
With the objective to design and synthesis of Schiff's base symmetrical liquid crystal dimmers and to study the effect of molecular structure variation ($o-ortho$, $m-meta$, $p-para$) and change in alkoxy terminal chain length on mesomorphic properties of liquid crystals, We have synthesized Schiff base dimers from dialdehyde derivative containing 2-hydroxy-1,3-dioxypropylene as short spacer with aniline derivatives having different lengths of terminal alkoxy chains ($n$ = 5, 7, 9). The chemical structure of the final products was characterized by proton nuclear magnetic resonance ($^1H$ NMR) spectroscopy and fourier transform infrared (FT-IR) spectroscopy. The mesomorphic properties and optical textures of the resultant dimers were characterized by differential scanning calorimetry (DSC) and polarized optical microscopy (POM). The existence of smectic A phase transition was confirmed by the observation of batonnets and fan shaped textures in optical microscopy when compound were heated from crystalline phase. All of the dimers of this series, with the exception of $\mathbf{2S_5}$ -ortho, -meta, -para, were thermotropic liquid crystal. The compound $\mathbf{2S_9}$ -meta was monotropic, while the rest were enantiotropic. It was found that the change in terminal alkoxy chain length has pronounced effect on the mesomorphic properties. The temperature range of smectic A phase window widens with increasing alkoxy chain length.
Nama Ryu;Lim, Soon-Sung;Jung, Sang-Hoon;Cho, Sae-Yun;Shin, Kuk-Hyun
Proceedings of the Korean Society of Applied Pharmacology
/
1998.11a
/
pp.185-185
/
1998
As part of our continuing attempts to evaluate biologically active compounds from fruiting bodies of cultivated fungus of Paecilomyces japonicus Yasuda, we conducted series of experiments on various fractions and compounds isolated by systematic fractionations. Our main efforts were concentrated on searching for compounds showing antitumor activities, which were tested on mice carrying Sarcoma-180 ascitic tumor. The antitumor activity was assessed by the life spans after these mice were administered Lp. with test compounds for consecutive 20 days. One of two pure compounds, which we have isolated to date, demonstrated significant prolongation of life span. ( Mean Survival Time: 30.3 days compared to that of control: 23.6 days). Structural analysis showed that this compound corresponds to D-mannitol. On the other hand, Ergosterol, another isolated pure compound didn't show efficient antitumor activity. We also obtained water-soluble fractions containing protein-bound polysaccharides and n-butantol fractions, which showed strong antitumor activities, 35.4(150%) and 32.1(136.0%) days of MST, respectively. In SRB assay, however, the test materials didn't show any toxic effects, but the level of acid phosphatase increased significantly when they were applied in cultured macrophage in vitro. Therefore, we concluded that antitumour activities might be attributed to immunostimulating rather than cytotoxic effects. Further experiments are underway to purify and structurally characterize new antitumour compounds from the active fractions.
Background: Pollinators help plants to reproduce and support economically valuable food for humans and entire ecosystems. However, declines of pollinators along with population growth and increasing agricultural activities hamper this mutual interaction. Nectar and pollen are the major reward for pollinators and flower morphology and volatiles mediate the specialized plant-pollinator interactions. Limited information is available on the volatile profiles attractive to honey bees and bumblebees. In this study we analyzed the volatile organic compounds of the flowers of 9 different plant species that are predominantly visited by honey bees and bumblebees. The chemical compositions of the volatiles were determined using a head space gas chromatography-mass spectrometry (GC-MS) method, designed to understand the plant-pollinator chemical interaction. Results: Results showed the monoterpene 1,3,6-octatriene, 3,7-dimethyl-, (E) (E-𝞫-ocimene) was the dominating compound in most flowers analyzed, e.g., in proportion of 60.3% in Lonicera japonica, 48.8% in Diospyros lotus, 38.4% Amorpha fruticosa and 23.7% in Robinia pseudoacacia. Ailanthus altissima exhibited other monoterpenes such as 3,7-dimethyl-1,6-octadien-3-ol (𝞫-linalool) (39.1%) and (5E)-3,5-dimethylocta-1,5,7-trien-3-ol (hotrienol) (32.1%) as predominant compounds. Nitrogen containing volatile organic compounds (VOCs) were occurring principally in Corydalis speciosa; 1H-pyrrole, 2,3-dimethyl- (50.0%) and pyrimidine, 2-methyl- (40.2%), and in Diospyros kaki; 1-triazene, 3,3-dimethyl-1-phenyl (40.5%). Ligustrum obtusifolium flower scent contains isopropoxycarbamic acid, ethyl ester (21.1%) and n-octane (13.4%) as major compounds. In Castanea crenata the preeminent compound is 1-phenylethanone (acetophenone) (46.7%). Conclusions: Olfactory cues are important for pollinators to locate their floral resources. Based on our results we conclude monoterpenes might be used as major chemical mediators attractive to both honey bees and bumblebees to their host flowers. However, the mode of action of these chemicals and possible synergistic effects for olfaction need further investigation.
A field experiment was conducted to find out the effects of liming (soil pH) and sources of N on the chemical constituents of soil and leaf lamina of burley tobacco. Treatments consisted of liming (nonliming, liming to soil pH 5.5 and 6.5) as the main plot and N sources[compound fertilizer of containing 3.9% $NH_4-N$ and 6.1% $NH_2-N,\;NaNO_3,\;(NH_2)_2CO\;and\;(NH_4)_2SO_4$]as the sub-plot. The soil pH was high in $NaNO_2$ plot, while low in $(NH_4)_2SO_4$. But the differences of Ca concentration in top soil among N sources were not detected. The $NO_3-N$ concentration in top soil was high in high limed and $NaNO_3$ plot. The $NO_3-N$ content of leaf (lamina) at 75 days after transplanting was high in $NaNO_3$ plot and CaO con-tent of leaf at 45 days after transplanting was high in high limed plot. But neither liming nor N source had effect on the contents of total nitrogen, $P_2-O_{5}\;and\;K_2O$ of leaf during growing season. There was no significant differences in total alkaloid and total nitrogen contents of cured leaf (lamina) to liming and N source. But when the source of N was $NaNO_3$, the content of total alkaloid was increased by adding lime. When the source of N was $(NH_4$)_2SO_4$, the content of $K_2O$ in cured leaf was high while CaO was low. But neither liming nor N source had effect on the contents of $P_2-O_{5}$ and MgO in cured leaf.
This study was conducted to evaluate the dry matter (DM) yield, quality and utilization of nutrients in Korean lespedeza (Lespedeza stipulacea Maxim.) swards as a roughage source. DM yield in various stages, chemical composition, and DM digestibility were observed, and DM intake, digestibility and utilization of nitrogen and energy by Korean native goat were determined. Experimental diets include three treatments: mixture hay (MH) 100%, MH (80%)+wild Korean lespedeza hay (LH) 20% and MH (60%)+LH (40%). As growth stage advanced, the DM yield of Korean lespedeza tended to increase significantly (p<0.05). The mean DM yield of all growing stages was observed as 7,336 kg/ha. Crude protein (CP) content of Korean lespedeza tended to decrease, but fibrous contents tended to increase when the growth stage advanced. The tannin content of Korean lespedeza was the highest at the bud stage (64.7 mg/g). However, it showed a tendency to decrease as the growth stage advanced, and thus it was the lowest at the ripe seed stage (26.8 mg/g) (p<0.05). With increasing level of LH, voluntary DM intake by Korean native goats slightly increased, but no differences were observed between diets. The digestibility of DM, cellular constituents and NDF was slightly higher in LH containing diets than that of MH 100% diet (p<0.05). There was no significant difference in apparently digested N% among all diets, but retained N% and retained N% of the absorbed were higher in MH (60%)+LH (40%) than those of other diets (p<0.05). A difference in the utilization of energy was not detected. In conclusion, Juvenile LH improved the digestibility of nutrients, presumably due to its high CP content and low fibrous compound. Especially, tannin in LH did not affect in DM intake, but increased the nitrogen utilization of Korean native goats. Accordingly, it could be suggested that Korean lespedeza has a potential to be provided as a roughage source for Korean native goats.
(2S,3R)-3-hydroxyhomoserine lactone (HSL) has been used as a key intermediate for the synthesis of various biologically active compounds. In this study, we demonstrated an efficient synthesis of HSL via anti selective dihydroxylation of a protected vinyl glycine analog with an oxabicyclo[2.2.2]octyl orthoester (OBO) ester group. Because the acyclic conformation of the substrate was efficiently controlled by the bulky OBO ester group, a diastereoselectivity of > 10 : 1 was obtained in the dihydroxylation reaction without the use of a chiral reagent. By using this result, the target compound 1 can be obtained from commercially available N-Cbz-L-serine 2 in seven steps with an overall yeid of 34%. This result could be applied to the stereoselective synthesis of biologically active molecules containing a vicinal amino diol moiety.
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