• YAKHAK HOEJI
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• v.50 no.6
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• pp.403-408
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• 2006

1-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3- (3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with hydroxylamine, and reduction with an overall yield of 74%. 2-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3-(3,4-dirnethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with isoamylnitrite, reduction in NaOH and reaction with HCI to form 5,6-dimethoxy-2-indanone, which was reacted with hydroxylamine and reduced with an overall yield of 42%. 5,6-Dimethoxyindan-1,2-dione-2-oxime, which was catalytically hydrogenated to afford cis-, and trans-1-amino-5,6-dimethoxyindan-1-ol as 3 : 1 ratio. This mixture was treated with Li and reacted with chloroacetyl chloride. Cis isomer was acylated and cyclized to synthesize rir -( ${\pm}$ )-7,8-dimethoxy-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one, but trans isomer was just acylated to form amide.

• Journal of the Korean Society of Food Science and Nutrition
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• v.40 no.12
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• pp.1734-1742
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• 2011

Conjugated linolenic acid (CLnA) and conjugated linoleic acid (CLA) are positional geometric isomers with three and two double bonds, respectively. In this study, perilla seed oil containing 60% ${\alpha}$-linolenic acid (C18:3) and 30% linoleic acid (C18:2) was used as a reaction substrate. After the perilla seed oil was hydrolyzed, conjugated fatty acids were synthesized using different reaction parameters, such as reaction time and concentration of sodium hydroxide. As a result, CLnA, CLA, and other newly synthesized conjugated isomers were present at levels of 14.5%, 14%, and 42.2%, respectively, when the reaction was performed with 20% NaOH, at $180^{\circ}C$, and for 1 hr. The results of GC-MS and fourier transform infrared spectroscopy (FT-IR) showed that CLnA isomer of cis-9, trans-11, and trans-13 octadecatrienoate, CLA isomer of cis-9, trans-11, and trans-10, cis-12 octadecadienoate, and other conjugated isomers were produced. Using urea, ${\alpha}$-linolenic acid could be concentrated from perilla seed oil hydrolysate. After concentration by urea, the concentration of ${\alpha}$-linolenic acid reached about 70%. After alkaline-isomerization was performed on the urea fraction containing 70% ${\alpha}$-linolenic acid, the content of CLnA increased up to 16.6%.

• Bulletin of the Korean Chemical Society
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• v.29 no.3
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• pp.541-545
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• 2008

Stable molecular isomers were calculated for the azobenzene crown ether p-tert-butylcalix[4]arene (1) in the host and their alkali-metal-ion complexes. The structures of two distinct isomers (cis and trans) have been optimized using DFT B3LYP/6-31G(d,p) method. Trans isomer of 1 is found to be 11.69 kcal/mol more stable than cis analogue. For two different kinds of complexation mode, the alkali-metal-cation in the crown-ether moiety (exo) has much better complexation efficiency than in the benzene-rings (endo) pocket for both isomers of 1. Sodium ion has much better complexation efficiency than potassium ion in all kinds of complexation mode with host 1. The Na+ complexation efficiency of the trans-complex (1) in the exo-binding mode is 8.24 kcal/mol better than cis-exo analogue.

• Bulletin of the Korean Chemical Society
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• v.16 no.9
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• pp.835-839
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• 1995

Mer,trans-Re(≡NC6H5)(PPh3)2Cl3, Ⅰ, reacted with trimethylphosphine to give a mixture of two stereoisomers, mer,trans-Re(≡NC6H5)(PMe3)2Cl3,Ⅱ, and fac,cis-Re(≡NC6H5)(PMe3)2Cl3, Ⅲ. These compounds could also be prepared from the reaction of Re(≡NC6H5)(PMe3)(PPh3)Cl3 with trimethylphosphine. In both reactions the mer,trans-isomer is a major product. The products have been characterized by NMR, elemental analysis, and X-ray crystallography. Crystal data for Ⅱ: monoclinic space group P21, a=10.053(1) Å, b=10.844(1) Å, c=10.058(2) Å, β=113.45(2)°, Z=2, R(wR2)=0.0348 (0.0894). Crystal data for Ⅲ: monoclinic space group P21/n, a=7.183(2) Å, b=16.983(4) Å, c=15.543(4) Å, β=90.38(2)°, Z=4, R(wR2)=0.0603 (0.1484).

• Journal of Microbiology and Biotechnology
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• v.23 no.2
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• pp.237-245
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• 2013

Canthaxanthin (cx) is a potent antioxidant that is chemically synthesized at the industrial scale and has imperative applications in the cosmetic and feed industries. An orange pigmented mesophilic bacterium, designated as K44, was isolated from soil samples of Kargil, India. Biochemical tests, 16S rRNA gene sequencing, and FAME analysis of the bacterium indicated it to belong in the genus Dietzia and is distinct from human isolates. The strain showed 98% 16S rRNA gene sequence homology with Dietzia maris DSM 43102. High-performance liquid chromatography profile of the pigments isolated from K44 showed two major peaks absorbing at 465.3 and 475 nm. The liquid chromatography-mass spectrometry (LC-MS) analysis of both these peaks revealed their m/z to be 564. The molecular weights, LC-MS/MS fragmentation patterns, and ${\lambda}_{max}$ of these fractions corresponded to all-trans- (475 nm) and 9-cis-(465.3 nm) cx isomers. The antioxidant activities of cis- and trans-cx isomers isolated from this bacterium were found to differ, where the cis-isomer showed higher free radical, superoxide radical, and reactive oxygen species scavenging activities than the alltrans- isomer, suggesting that 9-cis-cx is more effective as an antioxidant than the all-trans-cx.

• Journal of Photoscience
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• v.9 no.2
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• pp.302-304
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• 2002

pharaonis phoborhodopsin (ppR), a photophobic sensor of haloalkaliphilic bacteria, Natronobacterium phar-aonis, has retinal as a chromophore covalently bound to Lys in G-helix via a protonated Schiff base (PSB), as is the same as bacteriorhodopsin (bR). For ppR, the corresponding counter-ion is Asp residue (Asp75) located in C-helix. Here we investigated the influence of the protonated state of this counter-ion and its location on the chromophore configuration. Under alkaline condition, the chromophore configuration of D75E mutant was analyzed by HPLC. D75E had a much larger content of 13-cis isomer: the ratio of 13-cis to all-trans was 6:4 while the wild-type had this ratio of 1 :9. On the other hand, under acidic condition where Glu was associated, D75E had no 13-cis retinal isomer. Mutants whose Asp75 was replaced by neutral amino acids (D75N and D75Q) did not contain 13-cis retinal. Furthermore, retinal isomer compositions and the change in the visible ab- sorption spectra (indicating the dissociation state of Glu75) were measured under varying pH, and these were almost the same dependencies. These results indicate that an important factor determining the 13-cis isomer content is the presence of negative charge of the counter-ion against PSB, but not the size of this residue. Com- parison between the wild-type and D75E in alkaline solutions indicates the influence of the location of the counter-ion.

• Korean journal of food and cookery science
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• v.5 no.1
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• pp.69-74
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• 1989

Trans fatty acids are formed during refining process of vegetable oils (deodorization), hydrogenation, the high temperature treatment of oils and rancidity. Trans fatty acids contents were measured in vegetable oils added to tuna, oyster and mussel Can by Glass Capillary Gas Chromatography. Also Acid Values, Peroxide Values, iodine Values and Saponification Values of vegetable oils added to Can were determined. The results were as follows; 1. Among vegetable oils added to Can, trans fatty acids isomer of cotton seed oil were mostly t,c-18:2 and t,c,c-18:3. 2. Total average contents of trans fatty acids of soybean oil added to tuna Can (Ab) were shown the highest values among tuna (Aa, Ab), oyster, mussel (Cb) Cans. 3. All of oils added to Can had been keeping safe quality during 1 year or more with low Acid and Peroxide Values.

• Bulletin of the Korean Chemical Society
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• v.22 no.7
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• pp.693-698
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• 2001

Ab initio density functional calculations on the structural isomers, the hydration energies, and the hydrogen bond many-body interactions for gauche-, trans-protonated ethylenediamine-(water)3 complexes (g-enH+(H2O)3, t-enH+(H2O)3) have been performed. The structures and relative stabilities of three representative isomers (cyclic, tripod, open) between g-enH+(H2O)3 and t-enH+(H2O)3 are predicted to be quite different due to the strong interference between intramolecular hydrogen bonding and water hydrogen bond networks in g-enH+(H2O)3. Many-body analyses revealed that the combined repulsive relaxation energy and repulsive nonadditive interactions for the mono-cyclic tripod isomer, not the hydrogen bond cooperativity, are mainly responsible for the greater stability of the bi-cyclic isomer.

• Nutrition Research and Practice
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• v.3 no.2
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• pp.77-83
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• 2009

Retinoic acids (RAs) modulate growth, differentiation, and apoptosis in normal, pre-malignant & malignant cells. In the present study, the effects of RA isomers (all-trans RA, 13-cis RA, and 9-cis RA) on the cell signal transduction of human breast cancer cells have been studied. The relationship between RAs and an enzymatic antioxidant system was also determined. Estrogen-receptor (ER) positive MCF-7 and ER-negative MDA-MB-231 human breast cancer cells were treated with different doses of each RA isomers, all-trans RA, 13-cis RA, or 9-cis RA. Treatment of RA isomers inhibited cell viability and induced apoptosis of MCF-7 cells as a result of increased caspase activity in cytoplasm and cytochrome C released from mitochondria. All-trans RA was the most effective RA isomer in both cell growth inhibition and induction of apoptosis in MCF-7 cells. However, no significant effect of RA isomers was observed on the cell growth or apoptosis in ER-negative MDA-MB-231 cells. In addition, activities of antioxidant enzymes such as catalase and glutathione peroxidase were decreased effectively after treatment of RA in MCF-7 cells, whereas SOD activity was rarely affected. Thus, the present data suggest that all-trans RA is the most potential inducer of apoptosis and modulator of antioxidant enzymes among RA isomers in MCF-7 human breast cancer cells.

• Journal of the Korean Society of Food Science and Nutrition
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• v.33 no.9
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• pp.1529-1536
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• 2004

This study was designed to determine total trans fatty acids (tFAs) content of processed foods commonly consumed in the Korean diet and to prepare the database for the estimation of tFAs intake in Koreans. Total fat and tFAs content was determined by Soxhlet extraction method and attenuated total reflection infrared spectroscopy (ATR-IR), respectively. The tFAs positional isomers were analyzed using GC/MS spectrometer. In margarines, the content of tFAs ranged from 8.27% to 28.53%. Shortenings contained higher levels of tFAs (1.98~11.33%) than lards (1.83~1.96%). The content of tFAs in grilled confectioneries was wide (7.37~26.54%). Instant popcorns contained the highest amount of tFAs. Fried chickens had 0.44 to 14.85% of tFAs and french fries had 5.18 to 27.01% of tFAs. In fried snacks (crispy) and chocolates, tFAs were not detected. The amount of tFAs per serving size was the highest in instant popcorn, followed by french fries, fried snack (tortilla), doughnuts, and grilled confectioneries. TFAs isomer of margarines was mostly C18:1${\Delta}$9t. In shortenings and lards, the most abundant positional isomer of tFAs was C18:1${\Delta}$9t and C18:2${\Delta}$9t ${\Delta}$12t. Correlation coefficient of tFAs content between IR and GC/MS method was $r^2$=0.91.