• 제목/요약/키워드: cyclitol derivatives

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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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    • 제10권3호
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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.

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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    • 제9권1호
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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.

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

  • 손주환;남종우;김유옥
    • 대한화학회지
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    • 제15권3호
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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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Cyclitol 유도체 합성에 관한 연구 (제4보) DL-epi-inosose-2의 전해환원 (Synthesis of Cyclitol Derivatives (IV) Electrolytic Reduction of DL-epi-inosose-2)

  • 손주환;남종우;박흥조
    • 대한화학회지
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    • 제16권2호
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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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'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)- ('Studies on the Synthesis of Cyclitol derivatives' -Synthesis of Inositols, p-Hydroxybenzoates and thier Antimicrobial test for food industry)

  • 손주환
    • Applied Biological Chemistry
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    • 제13권3호
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    • pp.197-205
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    • 1970
  • 1. myo-inositol (aeeeee) 에서 scyllo- (eeeeee), epi-(aeaeee) 및 muco-inositol (aaaeee)에 도달(到達)시킬 수 있었다. 2. inositol의 과산화수소(過酸化水素) 산화(酸化)는 ax. 수산기(水酸基)가 산화(酸化)되어 microbial oxidation, 접촉산화(接觸酸化)에서와 대등(對等)한 inosose를 얻고, 이것은 산성(酸性)에서 $NaBH_4$로 환원(還元)하면 eq.-alcohol이 되며, 한편 접촉산원(接觸還元)하면 az. alcohol 이 된다. 3. inositol의 p-HBA ester인 사종(四種) 신화합물(新化合物) [III], [XII], [XVI], [XXI]을 합성(合成)하였다. 4. 이들 ester는 모두 항균작용(抗菌作用)이 있고 pH의 저하(低下)로 증대(增大)되는 경향(領向)이 있으며 muco-inositol ester는 가장 강력(强力)하고, 이는 입체구조(立體構造)와 관련(關聯)되는 것 같다.

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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)- (Studies on the Synthesis of Cyclitol derivatives -Part 5. Synthesis of O-(p-hydroxybenzoyl)-inositols and their test for food industry-)

  • 손주환
    • 한국식품과학회지
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    • 제5권4호
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    • pp.240-248
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    • 1973
  • 1. myo-inositol의 산화(酸化) 생성물(生成物)인 inosose를 환원(還元)하여 ax.- 및 eq.-alcohol에 도달(到達)시켰다. 2. 2-O-(p-hydroxybenzoyl)-myo-inositol [IX], 4-O-(p-hydroxybenzoyl)-myo-inositol [X], O-(p-hydroxybenzoyl)-scyllo-inositol [XX], 그리고 2-O-(p-hydroxybenzoyl)-epi-inositol [XXVI] 등(等) 신화합물(新化合物) 4종(種)을 합성(合成)하였고 이것을 얻기 위하여 합성(合成)한 [V], [VI], [VII], [VIII], [XVIII], [XIX], [XXIV], [XXV] 등(等) 8종(種) 화합물(化合物)도 아직까지의 문헌(文獻)에 기재(記載)가 없는 화합물(化合物)들이다. 3. 여기서 합성(合成)한 ester [IX] [X], [XX], [XXVI] 4종(種)은 모두 항균력(抗菌力)이 나타나며 epi-inositol ester [XXVI] 의 Aspergillus oryzae에 대(對)한 항균력(抗菌力)이 가장 강력(强力)하게 나타난다. 이와 같이 항균력(抗菌力)은 화합물(化合物)의 입체구조(立體構造)와 관련(關聯)되는 것 같다.

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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)- (Studies on the Synthesis of Cyclitol derivatives -Part 6. Synthesis of O-(5-nitro-2-furoyl)-inositols and their test for food industry-)

  • 손주환;김용인;박영랑
    • 한국식품과학회지
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    • 제5권4호
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    • pp.249-257
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    • 1973
  • 1. myo-inositol에서 산화(酸化), 환원반응(還元反應)을 거쳐서 scyllo-[XVI], epi-inositol[XXI], ax.-과 eq.-alcohol[III],[IV],[XXIII],[XXIV]등(等)에 도달(到達)시켰고, muco-inositol[XXIX]을 합성(合成)하였다. 2. inositol stereomer의 5-nitrofuroic acid ester인 8종(種) 신화합물(新化合物)을 합성(合成)하였다. 즉 hexakis-O-(5-nitro-2-furoyl)-myo-inositol [IX], hexakis-O-(5-nitro-2-furoyl)-scyllo-inositol [XXI], hexakis-O-(5-nitro-2-furoyl)-epi-inositol [XXVII], hexakis-O-(5-nitro-2-furoyl)-muco-inositol [XXXII], 2-O-(5-nitro-2-furoyl)-myo-inositol [VII], 4-O-(5-nitro-2-furoyl)-myo-inositol [VIII], O-(5-nitro-2-furoyl)-scyllo-inositol [XX], 그리고 2-O-(5-nitro-2-furoyl)-epi-inositol [XXVI] 등(等)이다. 3. 이 8종(種) ester는 모두 항균력(抗菌力)이 있고, scyllo-, myo-, epi-, muco-inositol ester 의 순(順)으로 증대(增大)되는 경향(傾向)이 있으며 항균력(抗菌力)은 ester의 입체구조(立體構造)와 관련(關聯)되는 것이라 생각된다.

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Cyclitol 유도체합성을 위한 Furfural 유도체의 반응에 관한 연구. Furfural, 5-Bromo-및 5-Methylfurfural의 Cannizzaro 반응 (Reaction of Furfural Derivatives. Cannizzaro reaction of Furfural, 5-Bromo-and 5-Methylfurfural)

  • 손주환;김용인;남기대
    • 대한화학회지
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    • 제16권5호
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    • pp.290-297
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    • 1972
  • 메탄올(95%) 용매내 $0{\sim}40^{\circ}C$에서 푸르푸랄, 5-메틸 및 5-브로모푸르푸랄의 알코올성 수산화칼륨에 의한 Cannizzaro 반응은 4차반응이며 푸르푸랄은 5-메틸푸르푸랄보다 3배, 5-브로모푸르푸랄은 푸르푸랄보다 10배 빠르게 진행된다. 그리고 이 반응에서 푸르푸랄, 5-메틸푸르푸랄, 5-브로모푸르푸랄의 활성화에너지는 각각 10.46 Kcal/mole, 16.27 Kcal/mole, 9.62 Kcal/mole이며 ${\Delta}H^{\neq}$${\Delta}S^{\neq}$를 계산한 바 5-브로모푸르푸랄, 푸르푸랄, 5-메틸푸르푸랄의 순으로 증가 되었다.

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