• Archives of Pharmacal Research
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• 제27권7호
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• pp.751-756
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• 2004

Flavonoids have been demonstrated to exhibit a wide range of biological activities including anti-inflammatory and neuroprotective actions. Although a significant amount of flavonoids has been identified to be present as glycosides in medicinal plants, determinations of the biological activities of flavonoids were mainly carried out with aglycones of flavonoids. Therefore, the exact role of the glycosidation of flavonoid aglycones needs to be established. In an attempt to understand the possible role of glycosidation on the modulation of the biological activities of flavonoids, diverse glycosides of kaempferol, quercetin, and aromadendrin were examined in terms of their anti-inflammatory activity determined with the suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV2 microglial cells. The results indicated that glycosidation of aglycones attenuated the suppressive activity of aglycones on LPS-induced NO production. Although attenuated, some of glycosides, depending on the position and degree of glycosidation, maintained the inhibitory capability of LPS-induced NO production. These findings suggest that glycosidation of flavonoid aglycones should be considered as an important modulator of the biological activities of flavonoids.

• 한국응용과학기술학회지
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• 제18권2호
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• pp.127-135
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• 2001

Alkyl polyglucosides were synthesized by solvent-free glycosidation using ultrasonic emulsification. We examined glycosidation conditions of fatty alcohol with glucose hydrate and anhydrous glucose in the presence of p-toluenesulfonic acid. Glucose was emulsified in a molar excess of fatty alcohol for 20 minutes with a ultra-sonicator at room temperature and converted in a stirred reactor to more than 95% polyglucoside within $2.5{\sim}3.5$ hr under $20{\sim}30$ mmHg at $110^{\circ}C$ with a three-fold molar ratio of fatty alcohol to glucose in the presence of 1mol% p-toluenesulfonic acid. It was possible to obtain a polyglucoside mixture of HLB 13 consisting of 65% monoglucoside and 35% oligoglucoside with less than 1% of fatty alcohol.

• 대한화학회지
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• 제42권1호
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• pp.78-83
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• 1998

Campylobacter jejuni 그램 음성균의 O-antigen 부위를 구성하는 삼탄당의 반복 단위를 합성하기 위해서 먼저 이들에 포함된 알트로헵토오스의 합성과 ${\alpha}$-알트로피라노시드를 선택적으로 형성시키는 방법을 개발하여야 한다. 본 연구에서는 알알 유도체에 선택적으로 1, 2-trans glycosidation을 시킴으로서 ${\alpha}$-알트로피라노시드 결합을 갖는 이당류를 합성하고자 하였다. 4, 6-O-Benzylidene-D-allal을 DMDO(3, 3-dimethyl diox-irane)와 반응시켜 1, 2-무수당 중간체를 만들고 아릴 알코올과 글루칼 유도체들과 반응시킨 결과 아릴 ${\alpha}$-알트로피라노시드 유도체와 ${\alpha}$-알트로피라노시드 결합을 갖는 이당류를 효과적으로 합성할 수 있었으며 마노오스등에서 간접적으로 ${\alpha}$-알트로피라노시드를 만드는 기존의 방법을 대체할 새로운 방법임을 확인 할 수 있었다.

• 대한화학회지
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• 제43권4호
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• pp.375-377
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• 1999

• 약학회지
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• 제40권2호
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• pp.163-169
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• 1996

Glycosidation of 20(S)-protopanaxadiol obtained by the alkaline hydrolysis of total ginsenosides with 2,3,4,6-tetra-O-acetyl-${\alpha$-D-glucopyranosyl bromide in the presence of $CdCO_3$ in benzene-dioxane gave a mixture of acetylated monoglucosides and diglucosides in a total yield of 68%. Under the same condenstion condition, 20-dehydroxyglucosides were formed by dehydration of 12-O-glucosides. The structures of produced glycosides were elucidated as 3-O-${\beta$-D-glucopyranosyl-20(S)-protopanaxadiol, 12-O-${\beta$-D-glucopyranosyl-dammar-20(22), 24-dien-$3{\beta},12{\beta}$-diol, 3,12-di-O-${\beta}$-D-glucopyranosyl-dammar-20(22), 24-dien-$3{\beta},\;12{\beta}$-diol, respectively.

• 약학회지
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• 제38권4호
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• pp.425-429
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• 1994

The genuine aglycone, 20(S)-protopanaxadiol, obtained from the leaves of Panax ginseng as a result of direct alkaline treatment was isolated and characterized by spectroscopic evidences. The study on the yield of genuine aglycone which is produced from the treatment of some kinds of alkali was carried out. $Ginsenoside-Rh_2$ was synthesized by conjugation of 2,3,4,6-tetra-O-acetyl-${\alpha}$-D-glucopyranosyl bromide to 20(S)-protopanaxadiol in the presence of silver carbonate and cadmium cabonate. The preparation of $ginsenoside-Rh_2$ by this method is a new one which the yield of this saponin can be improved in the mild condition.

• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 1993년도 제2회 신약개발 연구발표회 초록집
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• pp.115-115
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• 1993

i) total ginsenoside의 분리 시판백삼(900g)을 상법에 따라 처리, 조 saponin을 얻었으며 (24g) 이를 20(S)-protopanaxadiol을 얻는 원료로 사용하였다. ii) 20(S)-protopanaxadiol의 분리연구 본 연구에서 가장 중요한 단계는 20(S)-protopanaxadiol을 다량 얻는 것이다. 그러나 인삼 saponin을 산으로 가수분해하면 진성 aglycone 인 20(S)-protopanaxadiol이 얻어지지 않고 artifact sapogenol인 panaxadiol이 얻어진다. 이를 해결하기 위하여 sodium ethoxide의 ethanol 용액, sodium butoxide의 butanol 용액, sodium methoxide의 pyridine 용액, sodium methoxide의 DMSO 용액등의 조건에서의 가수분해를 검토한 결과 aprotic polar splvent인 DMSO용매중에서의 분해가 가장 좋음을 알았다. iii) ginsenoside Rh$_2$의 합성연구 Koenigs-Knorr 법에 의하여 bromosugar와 20(S)-protopanaxadiol의 glycosidation 반응결과 약 40%의 수득률로 합성됨을 확인하였다.

• 약학회지
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• 제45권6호
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• pp.575-581
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• 2001

The galactolipid M-5, which showed anti-inflammatory activity is glycoglycerolipid isolated from the Okinawa marine sponge Phyllospongia foliascens. Glycolipids have been synthesized by various methods, especially it were generally known that synthetic method of M-5 analogue and synthetic method of various glycolipids by glycosidation after synthesis of glycerolipid part. The others, it was not suggested that synthetic method via glycosylglycerol obtained by degradation from diglycoside. This study was carried out to investigate the synthesis of galactosylglycerol from melibiose as M-5 intermediate. Synthesis of galactosylglycerol was accomplished by selective protection of hydroxy group of sugar and diol cleavage by Pb(OAc)$_4$. As a result, galactosylglycerol was synthesized by 8 steps pathway and their structures were elucidated by analysis instrument.

• 대한화학회지
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• 제23권1호
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• pp.46-51
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• 1979

Silver triflate와 syn-collidine 존재하에서 3,4,6-tri-O-acetyl-2-phthalimido-${\beta}$-D-glucopyranosyl bromide (2)와 1,2;3,4-di-O-isopropylidene-${\alpha}$-D-galactopyranose (3)를 반응시켜 1,2;3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-${\beta}$-D-glucopyranosyl)-${\alpha}$-D-galactopyranose (4)를 $86{\%}$의 수득률로 얻었다. 화합물 4를 hydrazine과 작용시켜 phthalimido기와 acetyl기를 동시에 제거한후, 다시 acetyl화하고 isopropylidene기와 O-acetyl기를 가수분해하면 6-O-(2-acetamido-2-deoxy-${\beta}$-D-glucopyranosyl)-D-galactopyranose (1)가 총수득율 $65.8{\%}$로 얻어졌다. 또한 화합물 4를 변형시켜 특정위치에 hydroxyl기를 가진 몇 가지 유도체도 합성하였다.