• Title/Summary/Keyword: 1-O-acetyl-4R

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Two Polymorphs of Structures of $\alpha,\alpha$-Trehalose Octaacetate Monohydrate

  • Park, Young-Ja;Shin, Jung-Mi
    • Bulletin of the Korean Chemical Society
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    • v.14 no.2
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    • pp.200-206
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    • 1993
  • Structures of two polymorphs of ${\alpha},{\alpha}$-trehalose octaacetate monohydrate, $C_{28}H_{38}O_{19}\;{\cdot}\;H_2O$, have been studied by X-ray diffraction method. ${\alpha},{\alpha}$-trehalose (${\alpha}$-D-glucopyranosyl ${\alpha}$-D-glucopyranoside) is a nonreducing disaccharide. The polymorph I belongs to the monoclinic $P2_1$, and has unit cell parameters of a=10.725(l), b=15.110(4), c=11.199(5) ${\AA}$, ${\beta}=108.16(2)^{\circ}$ and Z=2. The polymorph II is orthorhombic $P2_12_12_1$, with a=13.684(4), b=15.802(4), c=17.990(9) ${\AA}$ and Z=4. The final R and R$_w$ values for monoclinic polymorph I are 0.043 and 0.048 and for orthorhombic polymorph II are 0.116 and 0.118, respectively. Those R values of polymorph II are high because the large thermal motions of acetyl groups and the poor quality of the crystal. The molecular conformations in the two polymorphs are similar. Both D-glucopyranosyl rings have chair $^4C_1$ conformations and atoms of glycosidic chain ${\alpha}(1{\rightarrow}1)$ linkage are coplanar. The primary acetate groups of the pyranose residues assume both gauche-trans conformations. The molecules of two polymorphs have pseudo-C$_2$ symmetry at glycosidic O(1) atom. The bond lengths and angles are normal compared with those in other acetylated sugar compounds. The molecules in the monoclinic crystal are held by the hydrogen bonds with the water molecules and by van der Waals forces.

Preparation of a New Chiral Stationary Phase Based on (2S,3S)-O,O'-Bis-(10-undecenoyl)-N,N'-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol and Its Application

  • Hyun, Myung Ho;Boo, Chang-Jin;Choi, Hee-Jung;Kim, Yun-Kyoung;Kang, Bu-Sung;Ha, Hyun-Ju;Choi, Min-Ki;Tan, Guang-Hui
    • Bulletin of the Korean Chemical Society
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    • v.27 no.11
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    • pp.1769-1774
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    • 2006
  • A new liquid chromatographic chiral stationary phase based on (2S,3S)-O,O'-bis-(10-undecenoyl)-N,N'-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butandiol was prepared starting from (2R,3R)-1,4-bis(benzyloxy)-2,3-butanediol. The new chiral stationary phase was applied to the resolution of racemic anilide derivatives of N-acetyl-a-amino acids, 1,1'-bi-2-naphthol and 3,3'-diaryl-1,1'-bi-2-naphthols. The CSP was also applied to the resolution of some chiral drugs including a diuretic, bendroflumethiazide, and non-steroidal anti-inflammatory agents such naproxen and alminoprofen. In every case, the chiral recognition efficiency of the new CSP was quite excellent.

Studies on the Xylans of Tropical Hardwoods (III) - Property of Purified Xylan - (열대산활엽수재(熱帯産闊葉樹材)의 Xylan에 관(関)한 연구(硏究) (III) - 정제(精製) Xylan의 성상(性状) -)

  • Lee, Jong Yoon
    • Journal of Korean Society of Forest Science
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    • v.56 no.1
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    • pp.77-81
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    • 1982
  • The property of four tropical hardwoods were analyzed. xylans, extracted with 24% of potassium hydroxide and purified according to ethanol titration procedure, were examined for Pn, the uronic acid, methoxyl groups and acetyl groups content. Only mangrove, whose xylan content is similar to that of hardwoods in the temperature zone, had the ratio of units of xylose residue to the units of uronic acid residue as high as that of hardwoods in the temperature zone. Content of methoxyl groups showed the same result as uronic acid residue content. Various hemicellulose including D-xylose residue were contained in xylans extracted by D M S O. Acetyl groups content was compressed of 5.4% of M D X and 6.8% of R D X. Xylans unextracted by D M S O had acetyl groups. Pn measured by the viscosity method was about 200 and similar to the hardwood xylans of temperature zone. DPn calculated by uronic acid residue was similar to that of tropical zone.

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Purification and Structural Analysis of Antitumor Polysaccharides Obtained from Ganoderma lucidum IY 009 (Ganoderma lucidum IY 009로 부터 분리된 항암성 다당류의 정제 및 구조분석)

  • Lee, Kweon-Haeng;Jeong, Hoon;Lee, June-Woo;Han, Man-Deuk;Choi, Kyoung-Sook;Oh, Doo-Hwan
    • Microbiology and Biotechnology Letters
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    • v.22 no.2
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    • pp.190-196
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    • 1994
  • Alkali soluble(AS) fraction, revealed the highest antitumor activity of the alkali extracted fractions of G. lucidum IY 009, was loaded on DEAE cellulose(OH$^{-}$ form) column. AS-1, AS-2, AS-3, AS-4 and AS-5 were obtained by stepwise elution with H$_{2}$O, 0.1 M NaHCO$_{3}$, 0.3 M NaHCO$_{3}$, 0.5 M NaHCO$_{3}$ and 0.5 N NaOH respectively, and their antitumor activities(I.R. %) against the sarcoma 180 were 97.5%, 68.0%, 73.0%, 81.0% and 66.0% respectively. AS-1 observed highest antitumor activity was appeared as single peak on the Sepharose CL-4B column chromatography, and their molecular weight was about 580,000 dalton. The carbohydrate content of AS-1 was 98.9%, their monosaccharide consisted of 67.5% of mannose, 22.5% of xylose, 5.8% of glucose, 1.8% of galactose and 2.0% of ribose. AS-1 was assumed $\alpha $linkaged xylomannan having infrared absorption at 864.3 cm$^{-1}$. The main alditol acetates of AS-1 were identified as 1,5-Di-O-acetyl1-2,3,4-Tri-O-methylxylitol, 1,4,5-Tro-O-acety1-2,3,6-Tri-O-methylmannitol and 1,3,4,5-Tetra-O-acety1-2,6-Di-O-methylmannitol by methylation analysis, and their molar ratio was 1 : 2 : 1. The core portion of AS-1 might be $\alpha $-(1$\longrightarrow $ 4)mannopyranosyl unit branched with side chain, C1 of xylopyranosyl residue linked to C3 of every 3 mannopyranosyl units, and the degree of polymerization of structural unit in AS-1 was about 835.

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Integracide K: A New Tetracyclic Triterpenoid from Desmodium uncinatum (Jacq.) DC. (Fabaceae)

  • Tsafack, Borice Tapondjou;Ponou, Beaudelaire Kemvoufo;Teponno, Remy Bertrand;Nono, Raymond Ngansop;Jenett-Siems, Kristina;Melzig, Matthias F.;Park, Hee Juhn;Tapondjou, Leon Azefack
    • Natural Product Sciences
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    • v.23 no.2
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    • pp.113-118
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    • 2017
  • A new tetracyclic triterpenoid [4,4,24-trimethylcholesta-${\Delta}^{8,9;14,5;24,28}$-trien-$3{\beta},11{\beta},12{\alpha}$-triol-12-acetate, 3-sulfate] sodium salt (1), together with eight known compounds including ergosterol $5{\alpha},8{\alpha}$-endoperoxide (2), 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (3), 3-O-${\beta}$-D-2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (4), hydnocarpin (5), derrone (6), isovitexin (7), erythrinin C (8), and 5,4'-dihydroxy-2"-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone (9), were isolated from the EtOAc soluble fraction of the methanol extract of aerial part of Desmodium uncinatum collected in the western highland of Cameroon. The structures of these compounds were established by comprehensive interpretation of their spectral data mainly including 1D- ($^1H$ and $^{13}C$), 2D-NMR($^1H$-$^1H$ COSY, HMQC, HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis. The isolation of an integracide-like compound from plant origin is a very unusual finding.

Interchange Reaction Kinetics and Sequence Distribution of Liquid Crystalline Poly(ethylene terephthalate-co-2(3)-chloro-1,4-phenylene terephthalate)

  • Rhee, Do-Mook;Ha, Wan-Shik;Youk, Ji-Ho;Yoo, Dong-Il
    • Fibers and Polymers
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    • v.2 no.2
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    • pp.86-91
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    • 2001
  • Liquid crystalline (LC) poly(ethylene terephthalate-co-2(3)-chloro-1,4-phenylene terephthalate) [copoly(ET/CPT)] was prepared using poly(ethylene terephthalate) (PET) as a flexible spacer, terephthalic acid (TPA), and chlorohydroquinone diacetate (CHQDA). All reactions involved in the copolymerization were investigated using some model compounds: TAP was used for acidolysis, diphenylethyl terephthalate (DPET) for interchange reaction between PET chains, and 야-o-chlorophenyl terephthalate (DOCT) and di-m-chlorophenyl terephthalate (DMCT) for interchange reaction between PET and rigid rodlike segments. Activation energies obtained for the acidolysis of PET with TPA and for interchange reaction of PET with DPET, DOCT, and DMCT were 19.8 kcal/mol, 26.5 kcal/mole, and 45.9 kcal/mole, respectively. This result supports that the copolymerization proceeds through the acidolysis of PET with TPA first and subsequent polycondensation between carboxyl end group and CHQDA or acetyl end group, which is formed from the reaction of CHQDA and TPA. Also, it was found that ester-interchange reaction can be influenced by the steric hindrance. Copoly(ET/CPT)s obtained has ethylene acetate end groups formed from acetic acid hydroxy ethylene end groups and showed almost the random sequence distribution for all compositions.

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The Development of Korean Traditional Wine Using the Fruits of Opuntia ficus-indica var. saboten - I. Characteristics of Mashes and Sojues - (손바닥 선인장 열매를 이용한 전통주 개발 - I. 전통주 제조기법을 이용한 발효주 및 증류주의 특성 -)

  • Bae, In-Young;Yoon, Eun-Ju;Woo, Jeong-Min;Kim, Joo-Shin;Yang, Cha-Bum;Lee, Hyeon-Gyu
    • Applied Biological Chemistry
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    • v.45 no.1
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    • pp.11-17
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    • 2002
  • Fermentation characteristics with/without nitrogen source and quality of the fruit distillate of Opuntia ficus-indica var. saboten were investigated during the manufacturing process of a Korean traditional liquor. As the fermentation period increased, acidity, brix degree, and alcohol concentration increased, whereas pH and contents of reducing sugar decreased. Acidity, pH, and brix degree were higher, whereas the content of reducing sugar lower, in the nitrogen source-added distillate than in the distillate without nitrogen source. The growth of yeast increased, while that of bacteria decreased; this trend was more prominent with the addition of a nitrogen source. Sojues, distilled from two types of mashes and diluted with $H_2O$ and tails of distillate into 22% alcohol concentration, showed pH $3.7{\sim}4.0$, acidity $0.02{\sim}0.10$, and $5.4{\sim}6.1$ $^{\circ}Brix$. Analysis through GC using direct injection methods revealed common volatile flavor compounds in sojues, including acetaldehyde, acetyl acetone, acetic acid ethyl ester, ethyl alcohol, 2-propyl alcohol, acetone, n-propyl alcohol, butanoic acid methyl ester, 2-phenyl ethanol, thymol, acetic acid phenyl ester, and vanillic aldehyde. As revealed through the sensory evaluation, no significant difference (p>0.05) in overall acceptability was shown among four experimental groups, while color and flavor showed significant differences(p<0.05).

Anti-osteoarthritis effect of Boswellia serrata gum resin extract in monosodium iodoacetate-induced osteoarthritic Sprague-Dawley rats (Monosodium iodoacetate 유도 골관절염 동물모델에서 보스웰리아 검레진 추출물의 항골관절염 효과 연구)

  • Jae In Jung;Ryong Kim;Eun Ji Kim
    • Journal of Nutrition and Health
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    • v.56 no.3
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    • pp.231-246
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    • 2023
  • Purpose: The aim of this study was to investigate the anti-osteoarthritic effect of the ethanol extract of Boswellia serrata gum resin (FJH-UBS) enriched with keto-β-boswellic acid and 3-O-acetyl-11-keto-β-boswellic acid compared to the conventional Boswellia serrata extract by adding the process of removing oil with hexane, in the monosodium iodoacetate (MIA)-induced osteoarthritis rat model. Methods: Sprague-Dawley (SD) rats were orally administered 0, 40, or 80 mg of FJH-UBS/kg body weight (BW)/day for 5 weeks and injected with MIA intra-articularly into right knee joints on day 15 to induce osteoarthritis. Changes in the knee joint microarchitecture, cartilage degradation, the expression of inflammatory mediators, cytokines, and matrix metalloproteinases (MMPs) in serum and synovia were observed. Results: Oral administration of FJH-UBS (80 mg/kg BW/day) reduced MIA-induced knee swelling and cartilage degradation and increased the expression of type II collagen and aggrecan in articular cartilage. Furthermore, FJH-UBS administration reduced MIA-induced increases in the serum levels of prostaglandin E2, leukotriene B4, interleukin (IL)-1β, IL-6, and MMP-13, and MIA-induced increases in the mRNA expressions of inducible nitric oxide synthase, cyclooxygenase-2, 5-lipoxygenase, IL-1β, IL-6, TNF-α, MMP-2, MMP-9, and MMP-13 in the synovia of knee joints. Conclusion: These results indicate that FJH-UBS exerts its anti-osteoarthritic effects by suppressing the expressions of inflammatory cytokines and MMPs and, thus, cartilage degradation. Furthermore, they suggest that FJH-UBS has potential use as a functional food that improves joint and cartilage health.