• Natural Product Sciences
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• 제4권4호
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• pp.268-273
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• 1998

Two new triterpenoid saponins, named segetoside D and E, have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical reactions and spectral data, structures of segetoside D and E have been established as: $28-O-[{\beta}-D-xylopyranosyl-(1{\rightarrow}4)-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)]-[5-O-acetyl-{\alpha}-arabinofuranosyl(1{\rightarrow}3)]-[4-O-acetyl-{\beta}-D-fucopyranosyl]-quillaic\;acid-3-O-[{\beta}-D-galactopyranosyl(1{\rightarrow}2)]6-O-methyl\;ester-{\beta}-D-glucuronopyranoside$ and $28-O-[{\beta}-D-xylopyranosyl-(1{\rightarrow}4)-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)]-[5-O-acetyl-{\alpha}-arabinofuranosyl(1{\rightarrow}3)]-[4-O-acetyl-{\beta}-D-fucopyranosyl]-quillaic\;acid\;-3-O-[{\beta}-D-galactopyranosyl(1{\rightarrow}2)]-6-O-n-butyl\;ester-{\beta}-D-glucuronopyranoside$, respectively.

• 약학회지
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• 제54권6호
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• pp.441-448
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• 2010

In present study, classification and quality control of Genus Polygonatum were developed using the isolated from Polygonati Odorati Rhizoma and Polygonati Rhizoma. 3 components were isolated from Butanol fractions of Polygonati Rhizoma, and 2 components were isolated from Hexane and Butanol fractions of Polygonati Odorati Rhizoma. All the components were obtained using silica gel and ODS column chromatography. The compounds were identified as adenosine, 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside, 22-O-methyl-14-hydrocxyfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-Dgalactopyranosyl-26-O-${\beta}$-D-glucopyranoside, ${\beta}$-Sitosteryl-3-O-${\beta}$-D-D-glucopyranoside, 14-hydoxylfurost-5-ene-3-O-${\beta}$-Dglucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-($1{\rightarrow}3$)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranoside through physicochemical data, spectroscopic methods ($^1H$-NMR, $^{13}C$-NMR, Mass) according references. The quality control of genus Polygonatum were conducted using HPLC quantitative analysis of 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\beta}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside, 14-hydoxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-($1{\rightarrow}3$)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranoside in 30 samples collected throughout Korea and China. This method provided a tool for standardization of mix or misusing the commercial Odorati Rhizoma and Polygonati Rhizoma. As a result, contained quantity of 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside was measured $0.008{\pm}0.006%$ and 14-hydoxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-(13)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-Dgalactopyranoside was measured $0.026{\pm}0.012%$.

• 생약학회지
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• 제30권2호
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• pp.168-172
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• 1999

Five compounds were isolated from the roots of Polygala tenuifolia (Polygalaceae). On the basis of spectroscopic evidences, the structures of these compounds were characterized as ${\alpha}-D-(6-O-sinapoyl)-glucopyranosyl(1{\rightarrow}2')-{\beta}-D-(3'-O-sinapoyl)-fructofuranoside$ (P3), ${\alpha}$-D-{6-O-(p-methoxybenzoyl)}-glucopyranosyl-$(1{\rightarrow}2')$-${\beta}$-D-{3'-O-(3',4',5'-trimethoxycinnamoyl)}-fructofuranoside(P4), ${\alpha}$-D-{6-O-(p-hydroxybenzoyl)}-glucopyranosyl-$(1{\rightarrow}2')$-${\beta}$-D-{3'-O-(3',4',5'-trimethoxycinnamoyl)}-fructofuranoside(P5), ${\alpha}-D-glucopyranosyl-(1{\rightarrow}2')-{\beta}-D-(1'-O-sinapoyl)-fructofuranoside$(P6), $1,5-anhydro-D-glucitol$(P7) respectively. ${\alpha}$-D-{6-O-(p-Methoxybenzoyl)}-glucopyranosyl-$(1{\rightarrow}2')$-${\beta}$-D-{3'-O-(3',4',5'-trimethoxycinnamoyl)}-fructofuranoside(P4) and ${\alpha}-D-glucopyranosyl-(1{\rightarrow}2')-{\beta}-D-(1'-O-sinapoyl)-fructofuranoside$(P6) were isolated for the first time from the genus of Polygala. 1,5-Anhydro-D-glucitol(P7) was isolated without hydrolysis for the first time from the root of Polygala tenuifolia.

• Korean Journal of Mathematics
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• 제20권4호
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• pp.415-422
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• 2012

In this paper, we define the weak property (${\beta}_{\kappa}$) and get the following strict implications. $$(UC){\Rightarrow}w-({\beta}_1){\Rightarrow}w-({\beta}_2){\Rightarrow}\;{\cdots}\;{\Rightarrow}w-({\beta}_{\infty}){\Rightarrow}(BS)$$.

• Journal of the Korean Wood Science and Technology
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• 제43권2호
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• pp.214-223
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• 2015

The bark of Acer komarovii was collected, ground, and extracted with 70% aqueous acetone to obtain concentrates. The concentrates were suspended in $H_2O$, and then successively partitioned with n-hexane, dichloromethane and ethylacetate to be freeze dried. A portion of ethylacetate fraction was chromatographed on a Sephadex LH-20 and a RP C-18 column with various aqueous MeOH-$H_2O$ (1:0, 1:1, 1:2, 1:5, 1:7, 1:9, 1:10, 3:1, and 4:1, v/v) eluents. Four compounds were isolated; (-)-epicatechin (9.6 g), procyanidin A2 (epicatechin-($4{\beta}{\rightarrow}8$, $2{\beta}{\rightarrow}O{\rightarrow}7$)-epicatechin) (1.3 g), procyanidin B2 (epicatechin-($4{\beta}{\rightarrow}8$)-epicatechin) (40.0 mg), and cinnamtannin B1 (epicatechin-($4{\beta}{\rightarrow}8$, $2{\beta}{\rightarrow}O{\rightarrow}7$)-epicatechin-($4{\beta}{\rightarrow}8$)-epicatechin) (690 mg). The analysis of the bark procyanidins showed that the basic unit constituting condensed tannins was only (-)-epicatechin. This study, for the first time, report the procyanidins of Acer komarovii bark.

• Applied Biological Chemistry
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• 제41권1호
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• pp.110-117
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• 1998

Ghana산 cacao bean으로부터 acetone으로 추출하고 Sephadex LH-20, MCI-gel CHP-20, Bondapak $C_{18}$ 및 Fuji gel ODS $G_3$, chromatography 등을 이용하여 7종의 polyphenol 화합물(compound 1 - compound 7)을 분리 정제하였고, 이들 화합물의 화학구조를 $^1H-NMR$, $^{13}C-NMR$, IR 및 MS를 사용하여 검색하였고 아울러 angiotensin converting enzyme(ACE) 저해효과를 조사 검토하였다. 분리정제한 7종의 polyphenol 화합물의 구조를 분석한 결과, compound 1: [(+)-catechin], compound 2: [(-)-epicatechin], compound 3: [procyanidin B-1, (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(+)-catechin], compound 4 : [procyanidin B-2, (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin], compound 5: [procyanidin B-7, (-)-epicatechin-$(4{\beta}{\rightarrow}6)$-(+)-catechin], compound 6 : (procyanidin B-2,3,3'-O-digallate) 및 compound 7: [cinnamtannin A-2, (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin]임을 동정하였다. ACE의 저해효과는 procyanidin B-2,3,3'-O-digallate (compound 6)가 $100\;{\um}M$에서 94.6%로 매우 우수하였으며, (+)-catechin (compound 1), (-)-epicate -chin (compound 2), procyanidin B류 (compound 3, 4, 5) 및 cinnamtannin A-2 (compound 7)도 각각 67.9%, 61.9%, 88.6%, 82.5%, 72.2% 및 82.3%의 비교적 우수한 저해효과가 있었다. 아울러 결합방식에서는 $4{\beta}{\rightarrow}6$보다 $4{\beta}{\rightarrow}8$의 결합방식이, 그리고 procyanidin 류에서는 gallate를 갖는 물질이 이를 함유하지 많은 물질보다 더욱 높은 ACE의 저해효과를 나타내었으며, 또한 hydroxyl 기가 많을수록 효소 저해효과도 증가하는 것으로 나타났다. 이와 같은 결과는 chocolate의 주원료인 cacao bean의 polyphenol 성분 또한 녹차 등에서 볼 수 있는 생리활성효과에 손색없는 것으로 판단되고, 이러한 기능성에 기초하여 chocolate, 음료 등의 식품이나 의약품의 기능성 소재로서의 산업적 응용 가능성이 높은 것으로 사료된다.

• Journal of Microbiology and Biotechnology
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• 제29권4호
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• pp.562-570
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• 2019

${\beta}$-Glucosylglycerol (${\beta}-GG$) and their derivatives have potential applications in food, cosmetics and the healthcare industry, including antitumor medications. In this study, ${\beta}-GG$ and its unnatural glycosides were synthesized through the transglycosylation of two enzymes, Sulfolobus shibatae ${\beta}$-glycosidase (SSG) and Deinococcus geothermalis amylosucrase (DGAS). SSG catalyzed a transglycosylation reaction with glycerol as an acceptor and cellobiose as a donor to produce 56% of ${\beta}-GGs$ [${\beta}$-$\text\tiny{D}$-glucopyranosyl-($1{\rightarrow}1/3$)-$\text\tiny{D}$-glycerol and ${\beta}$-$\text\tiny{D}$-glucopyranosyl-($1{\rightarrow}2$)-$\text\tiny{D}$-glycerol]. In the second transglycosylation reaction, ${\beta}$-$\text\tiny{D}$-glucopyranosyl-($1{\rightarrow}1/3$)-$\text\tiny{D}$-glycerol was used as acceptor molecules of the DGAS reaction. As a result, 61% of ${\alpha}$-$\text\tiny{D}$-glucopyranosyl-($1{\rightarrow}4$)-${\beta}$-$\text\tiny{D}$-glucopyranosyl-($1{\rightarrow}1/3$)-$\text\tiny{D}$-glycerol and 28% of ${\alpha}$-$\text\tiny{D}$-maltopyranosyl-($1{\rightarrow}4$)-${\beta}$-$\text\tiny{D}$-glucopyranosyl-($1{\rightarrow}1/3$)-$\text\tiny{D}$-glycerol were synthesized as unnatural glucosylglycerols. In conclusion, the combined enzymatic synthesis of the unnatural glycosides of ${\beta}-GG$ was established. The synthesis of these unnatural glycosides may provide an opportunity to discover new applications in the biotechnological industry.

• Applied Biological Chemistry
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• 제43권2호
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• pp.136-140
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• 2000

방울비짜루의 MeOH 추출물 및 수포화 BuOH추출물로부터 항균활성을 확인하고 그 원인물질을 구명하던 중 두 종의 steroid saponin을 분리하였다. 이들의 구조확인을 위해 $^1H,\;^{13}C$ NMR 및 2D NMR 등 분광학적 방법을 사용하였으며 최종 이들의 구조가 25S-spirostane계의 steroid saponin인$3-O-[{\beta}-D-glucopyranosyl-(1{\rightarrow}2)-{\beta}-D-glucopyranosyl]-(25S)-spirostan-3{\beta}-ol$ 및 $3-O-{{\beta}-D-glucopyranosyl-(1{\rightarrow}2)-[{\beta}-D-xylopyranosyl-(1{\rightarrow}4)]-{\beta}-D-glucopyranosyl}-(25S)-spirostan-3{\beta}-ol$인 것으로 동정되었다. 이 두 화합물은 방울비짜루로부터는 처음으로 분리되었다. 이들 saponin의 항균활성 및 항균 스펙트럼을 검사하기 위하여 20개 균주에 대한 MIC를 실시하였다. 이들은 그중 10개 균주에 대해 $100\;{\mu}g/ml$의 농도에서 세균의 성장을 저지하는 항균력이 있었으며 광범위한 항균 스펙트럼을 나타내었다.

• Archives of Pharmacal Research
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• 제22권4호
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• pp.423-427
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• 1999

A study was carried out to evaluate flavonol glycosides in leaves of Symplocarpus renifolius (Araceae). From the water fraction of the MeOH extract, three new flavonol glycosides were isolated along with three known compounds, Kaempferol-3-O-$\beta$-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranoside, quercetin-3-O-$\beta$-D-glucopyranosy-1-($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, and caffeic acid. The structures of the new flavonol glycosides were elucidated by chemical and spectral analyses a quercetin-3-O-$\beta$-D-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranoside, isorhamnetin-3-O-$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glucopyranosyl-7-O-$\beta$-D-glucopyranosdie, and quercetin-3-O$\beta$-D-glucopyranosyl-($1{\rightarrow}2$)-$\beta$-D-glycopyranosyl-7-O-($6^{IIII}$-trans-caffeoyl)-$\beta$-D-glucopyranoside.

• 한국식품과학회지
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• 제48권3호
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• pp.296-300
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• 2016

The effect of different temperatures (45, 55, 65, and $75^{\circ}C$) on the extraction of ${\beta}$-glucan and the properties of extracted ${\beta}$-glucan were investigated with four different varieties of barley. Jeju naked barley, blue barley, beer barley, and black barley contained 6.85, 5.13, 3.58, and 4.16% of ${\beta}$-glucan, respectively. ${\beta}$-glucan in barley was extracted in the range of 64.88 to 93.84% depending on the extraction temperature and barley variety. The ${\beta}$-glucans in Jeju naked barley, Jeju blue barley, and black barley were optimally extracted at $65^{\circ}C$ for 3 h and Jeju beer barley at $75^{\circ}C$. The extracted ${\beta}$-glucan resolubilized to 43.48-81.73% and the ratio of ${\beta}(1{\rightarrow}3)$ to ${\beta}(1{\rightarrow}4)$ linkage was in the range of 1:3.8-5.8. These results suggest that purification and properties of ${\beta}$-glucan depend not only on the water extraction temperature, but also on the barley variety.