• Archives of Pharmacal Research
• /
• v.24 no.2
• /
• pp.105-108
• /
• 2001

$\alpha$-Benzoyloxypaeoniflorin (1), a new antioxidant monoterpene $\alpha$-glycoside anomer was isolated from Paeonia suffruticosa along with known compounds, $\beta$-benzoyloxypaeoniflorin (2), paeonolide, paeoniflorin and mudanpioside H. The structure of 1 has been determined by comparing spectral data with those of $\beta$-Benzoyloxypaeoniflorin(2). Compound 1 exhibited moderately potent radical scavenging activity on DPPH radical.

• Bulletin of the Korean Chemical Society
• /
• v.19 no.11
• /
• pp.1233-1238
• /
• 1998

Transglycosylation reactions among methyl 2,3,4,6-tetra-O-methyl-D-glycopyranosides and isomeric butyl alcohols or cyclohexanol took place in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in dichloromethane. The extent of the reaction after 1 h and 24 h from mixing was determined by gas chromatography (GC). Anomerization of the substrate took place during the course of transglycosylation, which favors α anomer regardless of the anomeric configurations of the starting glycosides. Transglycosylation also favors the a anomer regardless of the steric bulkiness of the alcohol. tert-Butyl alcohol did not give any transglycosylation, suggesting the steric hindrance of approaching the bulky alcohol to the oxonium intermediate. A mechanism for the transglycosylation have been proposed.

• Korean Journal of Food Science and Technology
• /
• v.30 no.3
• /
• pp.709-716
• /
• 1998

Three kinds of anti-complementary system and macrophage activating polysaccharides, AB-20-Ia, AB-20-IIa-2a and AB-20-IVa-2 were isolated from the fruit body of Agaricus bisporus and their structures were characterized. The proteoglycan, AB-20-IVa-2 showing the most potent anti-complementary and macrophage activity was composed of glucose, galactose, mannose, xylose, fucose and arabinose in a molar ratio of 3.48:1.83:1.00:0.79:0.74:0.11 and its main component amino acids were phenylalanine (34.72%) and valine (27.84%). The neutral polysaccharides, AB-20-Ia and AB-20-IIa-2a showing lower activity than AB-20-IVa-2, consisted of xylose, glucose, mannose, fucose and arabinose in molar ratios of <0.05:<0.05:2.07:1.00:2.72 and 2.16:1.58:1.00:0.20:0.14, respectively. The molecular weights of AB-20-Ia, AB-20-IIa-2a and AB-20-IVa-2 were 840,000, 750,000 and 650,000 respectively. In the $^1H-\;and\;^{13}C-NMR$ spectra of AB-20-Ia and AB-20-IIa-2a, AB-20-Ia showed only ${\beta}-configuration\;(^1H:\;4.8\;ppm,\;^{13}C:\;107.0\;ppm)$ in the anomerization of the glycosidic linkages, while AB-20-IIa-2a had both ${\alpha}-anomer\;(^1H:\;5.4\;ppm,\;^{13}C:\;102.0\;ppm)\;and\;{\beta}-anomer$. Especially, AB-20-Ia and AB-20-IIa-2a showed acetyl signals $(^1H:\;2.5\;ppm,\;^{13}C:\;21.0\;ppm)$. In the methylation analysis of the three polysaccharides, high proportion of 1,6-linked glucofuranosyl residues were detected in AB-20-Ia, whereas 1,6-linked glucopyranosyl residues and branches linked at position 4 of those mainly contained in AB-20-IIa-2a. AB-20-IVa-2 consisted mainly of 1,2-linked xylofuranosyl residues and 1,6-linked glucopyranosyl residues and branches linked at position 3 of those.

• Proceedings of the PSK Conference
• /
• 2003.10b
• /
• pp.175.1-175.1
• /
• 2003

Galactosyl ceramides paly important roles in biological system as immunomodulator and essential constituents of membranes and cell walls. An efficient synthesis of $\alpha$-galactosyl ceramide, KRN 7000, derived from marine sponge Agelas mauritianus as accomplished via a short reaction involving the coupling ceramide moiety and trichloroacetimidate as glycosylation donor. We could synthesize $\alpha$-galactosyl ceramide stereoselectivity without $\beta$-anomer formation on a multigram scale.

• Journal of Applied Biological Chemistry
• /
• v.57 no.4
• /
• pp.321-324
• /
• 2014

Fresh and chopped aerial parts of Oryza sativa were extracted in 80% aqueous mehthanol, and the concentrated extract was successively partitioned in n-hexane, ethyl acetate (EtOAc), n-butanol (n-BuOH), and $H_2O$ fractions. From the n-BuOH fraction, two compounds were isolated through repeated silica gel and ODS column chromatography (c.c.). Based on nuclear magnetic resonance (NMR), mass spectrometry and infrared spectroscopy spectroscopic data, the compounds were identified to be adenosine (1) and phlomuroside (2). Especially, the configuration of both the anomer hydroxyl groups was determined as ${\beta}$ from the coupling constants of the anomer protons (J =6.0 and 7.6 Hz) in the $^1H-NMR$ spectra. This is the first report for the isolation of these compounds from Oryza sativa L.

• Journal of Applied Biological Chemistry
• /
• v.57 no.4
• /
• pp.347-352
• /
• 2014

The roots of Pueraria mirifica were extracted with 70% aqueous ethyl alcohol and partitioned into ethyl acetate (EtOAc), n-butyl alcohol (BuOH), and $H_2O$ fractions, successively. From the EtOAc fraction, four norsesquiterpenes were isolated through the repeated silica gel, octadecyl silica gel and Sephadex LH-20 column chromatographies. On the basis of physicochemical and spectroscopic data including nuclear magnetic resonance (NMR), mass spectrometry, and infrared spectroscopy, the chemical structures were identified as megastigm-5-en-3,9-diol (1), linarionoside B (2), 3,5,6,9-tetrahydroxymegastigm-7-ene (3) and 3,4,9-trihydroxymegastigma-5,7-diene (4). Especially, the configuration of the anomer hydroxyl group was determined as a from the coupling constants of the anomer proton (J =8.0 Hz) in the $^1H$-NMR spectrum. These compounds were isolated for the first time from the roots of P. mirifica in this study.

• Applied Biological Chemistry
• /
• v.48 no.1
• /
• pp.16-22
• /
• 2005

Many chitosanases, glycosyl hydrolases that catalyze the degradation of chitosan, have been found in microorganism. In this paper, classification of the enzyme has been described, which is based on the amino acid sequence (families) and splitting patterns (subclasses). Glycohydrolytic mechanisms such as inversion and retention of the substrate anomer are also discussed in context of the families. Interrelationship among the primary structure, clan, anomeric conversion and the splitting patterns has been suggested. In addition, advanced definition of chitosanase was introduced through the investigation of enzymatic products from partially N-acetylated chitosan as a substrate.

• Journal of Marine Bioscience and Biotechnology
• /
• v.12 no.2
• /
• pp.81-90
• /
• 2020

Sialic acid, which is contained in about 60-160 mg/kg in the edible bird's nest (EBN), is known to facilitate in the proper formation of synapses and improve memory function. The objective of this study is to extract effectively the sialic acid from edible bird's nest using affinity bead technology (ABT). After preparing the non-polar polymeric bead "KJM-278-28A" having a porous network structure, and then desorbed sialic acid was concentrated and dried. The analysis of the physicochemical properties of bead "KJM-278-28A" showed that the particle size was 400-700 ㎛, the moisture holding capacity was 67-70%, the surface area (BET) was 705-900 ㎡/g, and the average pore diameter 70-87 Å. The adsorption capacity of the bead "KJM-278-28A" for sialic acid was shown a strong physical force to bind sialic acid to the bead surface of 400 mg/L. In addition, as a result of analyzing the adsorption and desorption effects of sialic acid on water, ethanol, and 10% ethanol on the bead, it was confirmed that desorption effectively occurs from the beads when only ethanol is used. As a result of HPLC measurement of the separated sialic acid solution, a total of four sialic acid peaks of N-acetyl-neuraminic acid (Neu5Ac), α,β-anomer of Neu5Ac and N-glycoly-neuraminic acid were identified. Through these results, it was confirmed that it is possible to separate sialic acid from EBN extract with efficient and high yield when using ABT.

• Applied Biological Chemistry
• /
• v.48 no.4
• /
• pp.431-434
• /
• 2005

The quantitative analytical method for major antioxidants, ellagic acid and punicalagin, in pomegranate husk (Granati pericarpium) were established by HPLC. The optimal HPLC conditions were as follows: Column; Agilent Zorbax Eclipse XDB-C18 ($4.6{\times}150mm,\;5{\mu}m$), mobile phase; 1% formic acid in water (A) and 1% formic acid in MeCN (B) (gradient elution of 5% to 100% B for 50 min), flow rate; 0.8 ml/min., detection; UV 254 nm. The optimal pre-treatment conditions for HPLC analysis were as follows: 5 g of pomegranate husk in 100 ml of 95% EtOH, refluxed for 3 h. Under these analytical conditions, punicalagin and ellagic acid contents in Korean pomegranates husks which were cultivated in five different sites were determined. As results, the ellagic acid and punicalagin (as a mixture of ${\alpha-\;and\;{\beta}-anomer$) contents were the highest in Haepyung pomegranate husk $(15.27{\mu}g/mg)$ and Jangsung pomegranate husk $(16.21{\mu}g/mg)$, respectively.

• The Korean Journal of Mycology
• /
• v.29 no.1
• /
• pp.1-8
• /
• 2001

To examine the structural properties of the proteoglycan (GMPG, Ganoderma lucidum mycelial proteoglycan) obtained from mycelia in Ganoderma lucidum IY009, we obtained the low and high molecular proteoglycan by ultrafiltration and sepharose CL-4B column chromatography. The physicochemical properties of these fractions were as follows. When the proteoglycan separated by ultrafiltration and sepharose CL-4B column chromatography, its was not fractionated completely. The molecular weight of high molecular proteoglycan by the gel column chromatography (CH) was 250 kD and 2,000 kD, and low molecular proteoglycan was 12kD. The total carbohydrate was consisted of 75.7% (UH) and 96.7% (CH), and the low fraction was 72.7% (UL) and 87.1% (CL), respectively. The sugar of high and low molecular proteoglycan composed of glucose, mannose, fructose, galactose, xylose, ribose and arabinose. Glucose contents of all fraction were ranged from $46.9%{\sim}82.4%$ of the total sugar and the ratio of ${\alpha}$\;and\;{\beta}-glucose$ was $0.84{\sim}1.14$, and its indicated the proteoglycan to be ${\beta}-glucan$. Amino acids pattern showed that the fractions contained a large amount of aspartie acid, glutamic acid, alanine and leucine. These fractions showed the characteristics of IR absorption for ${\beta}-glucan$ at $890\;cm^{-1}\;and\;^{13}C-NMR$ spectroscopy showed the presence of the ${\beta}-1,3-glucan$ and a ${\beta}-1,6-glucan$.