• Microbiology and Biotechnology Letters
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• v.34 no.3
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• pp.204-210
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• 2006

Ethyl (S)-4-chloro-3-hydroxybutyrate is a useful intermediate for the synthesis of Atorvastatin, a chiral drug to hypercholesterolemia. In this research, two 4-chloro-3-hydroxybutyro-nitrile-degrading strains were isolated from soil sample. They were identified as Rhodococcus erythropolis strains by 16S rRNA analysis. The nitrile-degrading enzyme(s) were suggested to be nitrile hydratase and amidase rather than nitrilase from the result of thin layer chromatography analysis. The corresponding genes were obtained by PCR cloning method. The predicted protein sequences had identities more than 96% with nitrile hydratase ${\alpha}-subunit$, nitrile hydratase ${\beta}-subunit$, and amidase of R. erythropolis. The 4-chloro-3-hydroxybutyronitrile-hydrolyzing activities in both strains were increased dramatically by ${\varepsilon}-caprolactam$ which was known as good inducer for nitrile hydratase. Both intact cells and cell-free extract could hydrolyze the nitrile compound. So, the intact cell and the enzymes could be used as potential biocatalyst for the production of 4-chloro-3-hydroxybutyric acid.

• Natural Product Sciences
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• v.17 no.3
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• pp.175-180
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• 2011

Eleven compounds were isolated from fresh leaves of Abies koreana (Pinaceae), and structures of these compounds were determined to be 3-hydroxy-2-methyl-4-pyrone (1), maltol-3-O-${\beta}$-D-glucoside (2), (-)-epicatechin (3), naringenin 7-O-${\beta}$-D-glucopyranoside (4), naringenin-7-O-rhamnoglucoside (5), kaempferol 3-O-${\beta}$-D-glucopyranoside (6), (+)-isolariciresinol (7), secoisolariciresinol (8), rhododendrol (9), ferulic acid (10) and 4-(4-hydroxyphenyl)butan-2-one (rheosmin) (11) by comparing $^1H$-, $^{13}C$-NMR and MS spectroscopic data with reference values. Compounds 3, 5, 7, 8, 9, 10, 11 were isolated for the first time from A. koreana. Among eleven isolates, compounds 1, 7 and 11 showed inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglia in a concentration dependent manner.

• Archives of Pharmacal Research
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• v.26 no.1
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• pp.15-20
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• 2003

Two quinazolone alkaloids, (+)-febrifugine (1) and isofebrifugine (2), along with three coumarin derivatives, 6-hydroxy coumarin (3), skimmin (5), and $umbelliferone-7-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}4)-{\beta}-D-glucopyranoside$ (6), were isolated from the roots of Hydrangea chinensis. Compound 6 is a new compound. In addition, umbelliferone (4), linoleic acid (7), two steroidal glycosides (8, 9), three furfural derivatives (10-12), and butyl-$\beta$-D-fructofuranoside (13) were isolated from the leaves of the same plant. The structures of all isolates were elucidated by spectral methods.

• Korean Journal of Soil Science and Fertilizer
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• v.38 no.1
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• pp.25-31
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• 2005

A soil bacterium, Bacillus subtilis HJ927, exhibiting strong antagonistic property against pathogenic fungi was isolated from pepper fields infested with Phytophthora capsici. Pepper plants inoculated with P. capsici revealed severe root mortality while plants co-inoculated with B. subtilis HJ927 and P. capsici showed drastically reduced root mortality. Low molecular weight substances released by B. subtilis HJ927 mediated the plant protective effect. The anti-fungal compounds released by B. subtilis HJ927 were identified as 3-methylbutyric acid, 2-methylbutyric acid, and methyl 2-hydroxy, 3-phenylpropanoate by high-performance liquid chromatography and gas chromatography-mass spectrometry. In addition to these compounds, B. subtilis HJ927 also produced ${\beta}$-1,3-glucanase, a hydrolytic enzyme implicated in antifungal activity.

• Animal Bioscience
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• v.37 no.3
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• pp.522-535
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• 2024

Objective: Transition period is considered from 3 weeks prepartum to 3 weeks postpartum, characterized with dramatic events (endocrine, metabolic, and physiological) leading to occurrence of production diseases (negative energy balance/ketosis, milk fever etc). The objectives of our study were to analyze the periodic concentration of serum beta-hydroxy butyric acid (BHBA), glucose and oxidative markers along with identification, and validation of the putative markers of negative energy balance in buffaloes using in-silico and quantitative real time-polymerase chain reaction (qRT-PCR) assay. Methods: Out of 20 potential markers of ketosis identified by in-silico analysis, two were selected and analyzed by qRT-PCR technique (upregulated; acetyl serotonin o-methyl transferase like and down regulated; guanylate cyclase activator 1B). Additional two sets of genes (carnitine palmotyl transferase A; upregulated and Insulin growth factor; downregulated) that have a role of hepatic fatty acid oxidation to maintain energy demands via gluconeogenesis were also validated. Extracted cDNA (complementary deoxyribonucleic acid) from the blood of the buffaloes were used for validation of selected genes via qRTPCR. Concentrations of BHBA, glucose and oxidative stress markers were identified with their respective optimized protocols. Results: The analysis of qRT-PCR gave similar trends as shown by in-silico analysis throughout the transition period. Significant changes (p<0.05) in the levels of BHBA, glucose and oxidative stress markers throughout this period were observed. This study provides validation from in-silico and qRT-PCR assays for potential markers to be used for earliest diagnosis of negative energy balance in buffaloes. Conclusion: Apart from conventional diagnostic methods, this study improves the understanding of putative biomarkers at the molecular level which helps to unfold their role in normal immune function, fat synthesis/metabolism and oxidative stress pathways. Therefore, provides an opportunity to discover more accurate and sensitive diagnostic aids.

• Applied Biological Chemistry
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• v.44 no.3
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• pp.191-196
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• 2001

${\alpha},{\beta}$-Unsaturated carboxanilides 5 with trifluromethylated dihydro-1,4-oxathiins were synthesized for the development of new agrochemical fungicide. Chlorination of trifluoromethylated ${\beta}-keto$ ester 6 followed by the reaction with 1,2-mercaptoethanol gave intermediate 1,4-oxathiane 11. Without purification of 11, substitution of hydroxy group by chlorine, followed by dehydrochlorination of 10 in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-oxathiin ethyl ester 9. Acylation of the hydroxy group of the carboxylic acid 12 followed by treatment of various amines gave the corresponding trifluoromethylated dihydro-1,4-oxathiin carboxamides 5. Antifungal screening (in vivo) of the synthesized compounds against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. Where meta position of the phenyl group was substituted with isopropoxy or isopropyl group, excellent antifungal activities against rice sheath blight and wheat leaf rust were detected.

• Bulletin of the Korean Chemical Society
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• v.35 no.10
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• pp.2945-2949
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• 2014

As a part of ongoing phytochemical research on Euonymus alatus leaves and twigs, we have isolated one new reissantane-type triterpene (1), together with eight known triterpenes, isoarborinol (2), friedelin (3), abruslactone A (4), $3{\beta},22{\alpha}$-dihydroxyolean-12-en-29-oic acid (5), $3{\alpha},22{\alpha}$-dihydroxyolean-12-en-29-oic acid (6), $3{\alpha},22{\beta}$-dihydroxyolean-12-en-29-oic acid (7), $22{\alpha}$-hydroxy-3-oxoolean-12-en-29-oic acid (8), demethylregelin (9). The structure of 1 has been elucidated as 24,24-dimethyl-reissant-7(8),25-dien-$3{\alpha}$-ol, by extensive 1D and 2D spectroscopic methods including $^1H$-NMR, $^{13}C$-NMR, $^1H-^1H$ COSY, HSQC, HMBC and NOESY. Anti-inflammatory activities of the isolated compounds were determined as potential regulating excessive inflammatory responses in RAW264.7 macrophage cells. Particularly, abruslactone A (4) and demethylregelin (9) showed the most potent activity, which effectively reduced the expression of iNOS protein and subsequent nitric oxide production induced by lipopolysaccharide in RAW264.7 cells.

• YAKHAK HOEJI
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• v.51 no.1
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• pp.56-62
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• 2007

Twelve epoxy and hydroxydiosgenin derivatives (DI-1${\sim}$DI-12) were synthesized from diosgenin (25(R)-5-spirosten-3${\beta}$-ol). Diosgenin was epoxidized with m-chloroperoxybenzoic acid (mCPBA) to oxidize 25(R)-4${\alpha}$,5${\alpha}$-epoxyspirostane (DI-1). Diosgenin was reacted with DDQ to form 25(R)-1,4,6-spirostatrien-3-one (DI-2), which was treated with 30% H$_2$O$_2$ to give 25(R)-1${\alpha}$,2${\alpha}$-epoxy-4,6-spirostadien-3-one (DI-3) and treated with mCPBA to form 25(R)-6${\alpha}$,7${\alpha}$-epoxy-1,4-spirostadien-3-one (DI-7), respectively. DI-3 was reduced with NaBH$_4$ to afford 25(R) -1${\alpha}$,2 ${\alpha}$-epoxy-4,6-spirostadien-3${\beta}$-ol(DI-4) and reacted with Li metal in absolute ethanol to form 25(R)-2-ethoxy-1,4,6-spirostatrien-3-one (DI-5). DI-7 was reduced with NaBH$_4$ to produce 25(R)-3${\beta}$,7${\alpha}$-dihydroxy-4-spirostene (DI-8) and treated with Li metal in liquid ammonia to produce 25(R)-7${\alpha}$-hydroxy-4-spirosten-3-one (DI-9). DI-2 was reduced with NaBH$_4$ to form 25(R) -4,6-spirestadien-3${\beta}$-ol(DI-10), which was stirred with 30% H$_2$O$_2$ to synthesize 25(R)-4,6-spirostadien-3-one (DI-11) and reacted with mCPBA to give 25(R)-4${\beta}$,5${\beta}$ -epoxy-6-spirosten-3${\beta}$-ol (DI-12), respectively. The antinociceptive effects of synthesiz ed compounds were measured by hot plate method and compound DI-7 signifcantly exhibited antinociceptive effect. DI-2 decreased the serum triglyceride and total cholesterol levels in poloxamer P-407 injected rat.

• Natural Product Sciences
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• v.20 no.4
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• pp.269-273
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• 2014

Activity guided phytochemical examination of the rhizome of Phragmites communis has led to the isolation of two phenolic acids and two lignans. Structures of these compounds were elucidated as methyl gallate (1), ${\rho}$ -hydroxy cinnamic acid (2), (+) -lyoniresinol (3), (+)-lyoniresinol-9'-O-${\beta}$-D-glucopyranoside (4) by comparisons with previously reported spectral data. To investigate the melanogenesis inhibitory effects of these compounds, the melanin level and tyrosinase activity were examined in B16F10 melanoma cell. Each compound inhibited both tyrosinase activity and melanin synthesis compared with positive control, kojic acid and arbutin. These results suggest that the phenolic compounds from Phragmites communis might be developed as a potent skin whitenting cosmeceuticals.

• Journal of Microbiology and Biotechnology
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• v.21 no.9
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• pp.930-936
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• 2011

Two new cyclic depsipeptides wewakamide A (1) and guineamide G (2) have been isolated from the marine cyanobacterium Lyngbya semiplena and Lyngbya majuscula, respectively, collected from Papua New Guinea. The amino and hydroxy acid partial structures of wewakamide A and guineamide G were elucidated through extensive spectroscopic techniques, including HR-FABMS, 1D $^1H$ and $^{13}C$ NMR, as well as 2D COSY, HSQC, HSQC-TOCSY, and HMBC spectra. The sequence of the residues of wewakamide A was determined through a combination of ESI-MS/MS, HMBC, and ROESY. Wewakamide A possesses a ${\beta}$-amino acid, 3-amino-2-methylbutanoic acid (Maba) residue, which has only been previously identified in two natural products, guineamide B (3) and dolastatin D (4). Although both new compounds (1,2) showed potent brine shrimp toxicity, only guineamide G displayed significant cytotoxicity to a mouse neuroblastoma cell line with $LC_{50}$ values of 2.7 ${\mu}M$.