• Title/Summary/Keyword: Cyclitol

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A New Cyclitol Derivative from a Sponge Stelletta Species

  • Zhao, Qingchun;Liu, Yong-Hong;Hong, Jong-Ki;Lee, Chong-O.;Park, Jong-Hee;Lee, Dong-Seok;Jung, Jee-H.
    • Natural Product Sciences
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    • v.9 no.1
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    • pp.18-21
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    • 2003
  • Guided by the brine shrimp lethality assay, a new (4) and three known cyclitol derivatives (1-3) were isolated from the marine sponge Stelletta sp. Norsarcotride A (4) showed significant cytotoxicity against a small panel of five human tumor cell lines.

Cytotoxic Effects of Furanosesterterpenes, Cyclitol Derivatives, and Bromotyrosine Derivative Isolated from Marine Sponges

  • Sohn, Jae-Hak;Oh, Hyun-Cheol;Jung, Jee-H.;Bae, Song-Ja
    • Preventive Nutrition and Food Science
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    • v.10 no.3
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    • pp.257-261
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    • 2005
  • Marine sponges are known to produce a number of cytotoxic secondary metabolites. In the course of searching for cytotoxic metabolites from marine organisms, we have evaluated cytotoxic activities of six marine secondary metabolites isolated from various sponges. The cytotoxic compounds 1-6 were isolated by the application of various chromatographic methods, including column chromatography and HPLC. The molecular structures were mostly determined using mass spectrometry (MS) and Nuclear Magnetic Resonance (NMR) Spectroscopy. Furanosestererpenes (compounds 1-3) from Psammocinia sp., cyclitol derivatives (compounds 4 and 5) from Sarcotragus sp., and bromotyrosine-type compound (6) from an association of two sponges Jaspis wondoensis and Poecillastra wondoensis were evaluated for their cytotoxic activity against three cancer cell lines; Hep G2, HeLa, and MCF-7. All tested compounds exhibited cyctoxicity at concentrations ranging from $5\;\mug/mL\;to\;25\;\mug/mL.$ Particularly, among the tested compounds, compound 6 showed the highest potency displaying at least $80\%$ of cytotoxicity at $5\;\mug/mL$ level against all three cancer cell lines.

Synthesis of Cyclitol Derivatives (Ⅲ). Electrolytic Oxidation of myo-Inositol (Cyclitol 유도체 합성에 관한 연구 (제3보)-myo-Inositol의 전해 산화-)

  • Joo Hwan Sohn;Chong Woo Nam;Yu Ok Kim
    • Journal of the Korean Chemical Society
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    • v.15 no.3
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    • pp.127-132
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    • 1971
  • To obtain the various kinds of inosose stereomers, the process of electrochemical oxidation is more effective than chemical oxidation of myo-inositol. So that myo-inositol aqueous solution was electrolyzed by platinum and lead peroxide anode to confirming the occurrence of electrochemical oxidation. The result is that myo-inosose-2 is producing with high yield comparatively by electrolytic oxidation of myo-inositol. Also we studied about the relation between the electrolytic current efficiency and electrolytic temperature and anodic current density. The current efficiency is rising with lowering of electrolytic temperature identically in both anode such as platinum and lead peroxide and also rising with increasing of anodic current density in platinum anode, but inversely in lead peroxide.

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Synthesis of Cyclitol Derivatives (IV) Electrolytic Reduction of DL-epi-inosose-2 (Cyclitol 유도체 합성에 관한 연구 (제4보) DL-epi-inosose-2의 전해환원)

  • Sohn, Joo-Hwan;Nam, Chong-Woo;Park, Heung-Cho
    • Journal of the Korean Chemical Society
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    • v.16 no.2
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    • pp.93-99
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    • 1972
  • To obtain the various kinds of inositol stereomers, we have selected the process of electrolytic reduction of DL-epi-inosose-2 using Ni, Ta, Cu, Mo, Pb, Sn, W, Cd and Hg etc., as cathode. We think that this process gives greater variety than chemical processes. DL-epi-inosose-2 was synthesized by chemical oxidation of myo-inositol, dissolved in aqueous solution of potassium hydroxide, and used as electrolytic solution. To prevent anodic oxidation of cathode products the H-type diaphragm cell was used. As the results of paper chromatography of cathodic products, we obtained the $R_f$ values of myo-inositol and epi-inositol were in good agreement with literature values.

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Antidiabetic Coumarin and Cyclitol Compounds from Peucedanum japonicum

  • Lee, Sung-Ok;Choi, Sang-Zin;Lee, Jong-Hwa;Chung, Sung-Hyun;Park, Sang-Hyun;Kang, Hee-Chol;Yang, Eun-Young;Cho, Hi-Jae;Lee , Kang-Ro
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1207-1210
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    • 2004
  • The antidiabetic activity-guided fractionation and isolation of the 80% EtOH extracts from Peucedani Radix (Peucedanum japonicum, Umbelliferae) led to the isolation and characterization of a coumarin and a cyclitol as active principles, that is, peucedanol 7-O-${\beta}$ -D-glucopyranoside (1) and myo-inositol (2). Their structures were identified by spectroscopic methods. Compound 1 showed 39% inhibition of postprandial hyperglycemia at 5.8 mg/kg dose, and compound 2 also significantly inhibited postprandial hyperglycemia by 34% (P<0.05).

'Studies on the Synthesis of Cyclitol derivatives' -Synthesis of Inositols, p-Hydroxybenzoates and thier Antimicrobial test for food industry ('Cyclitol 유도체(誘導體) 합성(合成)에 관(關)한 연구(硏究)' -Inositol stereomer 와 p-Hydroxybenzoate의 합성(合成)과 식품공업상(食品工業上) 응용(應用)을 위한 항균시험(抗菌試驗)-)

  • Sohn, Joo-Hwan
    • Applied Biological Chemistry
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    • v.13 no.3
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    • pp.197-205
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    • 1970
  • Inositols are cyclohexanehexol and they have been known to be nine stereomers. Scyllo-inositol, epi-inositol and muco-inositol could be synthesized from myo-inositol. Scyllo-inositol and epi-inositol were obtained by oxidation and reduction process from myo-inositol. Myo-inositol and epi-inositol were oxidized by treatment, in solution, with dilute hydrogen peroxide. In all cases, only axial hydroxyl groups were oxidized and monoketons were obtained. Reduction of myo-inosose-2 with sodium boron hydride was carried out in $pH2{\sim}3.$ The reduction products were equatorial alcohol but: reduction of DL-epi-inosose-2 by catalytic reduction produced axial alcohol obtained. Inositol could be esterified. Hexa-O-(p-hydroxy benzoyl)-esters of myo-inositol, scyllo-inositol, epi-inositol and muco-inositol were synthesized and their antimicrobial action on microbes were tested for application to food industry. As the results, it was found that the activities of muco-inositol ester was more vigorous than others.

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Studies on the Synthesis of Cyclitol derivatives -Part 5. Synthesis of O-(p-hydroxybenzoyl)-inositols and their test for food industry- (Cyclitol 유도체(誘導體) 합성(合成)에 관(關)한 연구(硏究) -제(第)5보(報) O-(p-hydroxybenzoyl)-inositol류(類)의 합성(合成)과 식품공업상(食品工業上) 응용(應用)을 위한 시험(試驗)-)

  • Sohn, Joo-Hwan
    • Korean Journal of Food Science and Technology
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    • v.5 no.4
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    • pp.240-248
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    • 1973
  • Reduction of penta-O-acetyl-myo-inosose-2 by catalytic hydrogenation and with sodium-amalgam was carried out in alcohol solution of pH $3{\sim}4$. The former reduction product was axial-alcohol, and the latter equatorial-alcohol. On reduction of penta-O-acetyl-DL-epi-inosose-2 with sodium borohydride and sodium-amalgam in the previous condition, ax.-alcohol and eq.-alcrhol have been obtained. The synthesis of various inositol-p-hydroxybezoate are described. The esters have been characterized by paper chromatography and saponification, and their antimicrobial activities on some microbes were tested for the application of food industry. As the result, it was found that the antimicrobiol activity of epi-inositol ester was superior to its analogues.

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Studies on the Synthesis of Cyclitol derivatives -Part 6. Synthesis of O-(5-nitro-2-furoyl)-inositols and their test for food industry- (Cyclitol 유도체(誘導體) 합성(合成)에 관(關)한 연구(硏究) -제(第)6보(報) O-(5-nitro-2-furoyl)-inositol류(類)의 합성(合成)과 식품공업상(食品工業上) 응용(應用)을 위한 시험(試驗)-)

  • Sohn, Joo-Hwan;Kim, Yong-In;Park, Young-Rang
    • Korean Journal of Food Science and Technology
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    • v.5 no.4
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    • pp.249-257
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    • 1973
  • In the previous work, as we have reported on the reduction of penta-O-acetyl-myo-inosose-2 and penta-O-acetyl-DL-epi-inosose-2, axial and equatorial alcohol have been produced. The synthesis of various inositol 5-nitro-2-furoate are described. The esters have been obtained by reaction of 5-nitro-2-furoylchloride with inositol stereomers in chloroform at low temperature. The ester have been characterized by paper chromatography and other determination. For the applicable purpose of food industry, their antimicrobial activities on microbes were tested, and it was found that the antimicrobial activity of muco-inositol ester was superior to the others, and considered that result would be related to the stereochemical structure.

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Biochemical Components and Physiological Activities of Ice Plant (Mesembryanthemum crystallinum) (아이스플랜트(Mesembryanthemum crystallinum)의 생화학적 성분 및 생리활성 효과)

  • Kang, Seungmi;Kim, Seonjeong;Ha, Suhyun;Lee, Changryul;Nam, Sanghae
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.12
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    • pp.1732-1739
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    • 2016
  • The general components and cyclitol compounds of ice plant (Mesembryanthemum crystallinum) were analyzed to examine the possibility of using extracts as functional food materials, the antioxidant effects and antidiabetic activities of the extracts by solvent fraction were tested. Among the mineral contents, contents of K and Na were the largest ($1,213.33{\pm}2.52$ and $545.53{\pm}12.01mg/100g$, respectively), followed by S, Ca, P, and Mg in order of precedence. Among cyclitol compounds, content of D-pinitol was the largest ($4.04{\pm}0.08mg/g$) while contents of chiro-inositol and myo-inositol were relatively small ($2.82{\pm}0.01$ and $0.25{\pm}0.01mg/g$, respectively). Among total phenol contents by solvent fraction, contents of chloroform and ethyl acetate fractions were large ($35.80{\pm}1.33$ and $23.70{\pm}0.62mg\;GAE/g$, respectively). Among antioxidant activity levels examined by DPPH, ABTS, FRAP, and lipid/MA assays, the chloroform fraction commonly showed the highest level of activity while the ethyl acetate fraction showed relatively high levels of activity. The antioxidant activity levels were proportional to total phenol contents by solvent fraction. As for antidiabetic effects, all solvent fractions showed at least 50% ${\alpha}-glucosidase$ inhibitory activity levels while the ethyl acetate, butanol, and chloroform fractions showed high levels activity of $90.33{\pm}0.40$, $87.98{\pm}0.16$, and $86.38{\pm}0.51%$, respectively. The ${\alpha}-amylase$ inhibitory actively levels were in the range of $25.63{\pm}1.45{\sim}60.34{\pm}2.67%$, which was lower than the ${\alpha}-glucosidase$ inhibitory activity levels, but the inhibitory activity levels by solvent fraction were similar. Given the above study results, ice plant can be utilized as a natural material with antioxidative and antidiabetic functionality.