• 약학회지
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• 제35권3호
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• pp.240-244
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• 1991

A new lupane triterpenoid saponin, 3, 11-dihydroxy-lupan-20-en-28-oic acid 28-o-$\alpha$-L-rhamnopyranosyl-(1$\rightarrow$4)-$\beta$-D-glucopyranosyl-(1$\rightarrow$6)-B-D-glucopyranosyl ester, have been isolated from the leaves of Acanthopanax koreanum Nakai (Araliaceae) together with one known flavonol glycoside, rutin. The structure were elucidated on the basis of spectral and chemical evidence.

• Bulletin of the Korean Chemical Society
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• 제21권6호
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• pp.562-566
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• 2000

$\beta-D-Mannopyranosyl$ disaccharides have been obtained from the coupling of 4,6-O-benzylidene derivatives of ethylthio $\alpha-D-mannopyranoside$ employing NIS-TfOH promoter. NIS-TfOH promoted couplings of the corresponding ethylthio $\beta-D-glucopyranoside$ and produced $\alpha-D-glucopyranosyl$ disaccharides. IDCP (iodonium dicollidine perchlorate) was inactive toward the 4,6-O-benzylidenated ethylthio glucopyranosyl donor. However,lDCP coupled the 4,6-O-benzylidenated $ethylthio-\beta-D-galactopyranoside$ to give a-D-galactopyranosyl disaccharides.

• Archives of Pharmacal Research
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• 제26권9호
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• pp.706-708
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• 2003

A new 24-nor-lupaneglycoside was isolated from the leaves of Acanthopanax trifoliatus. Based on spectroscopic data its chemical structure was determined as 24-nor-11$\alpha$-hydroxy-3-oxo-lup-20(29)-en-28-oic acid 28-Ο-$\alpha$-L-rhamnopyranosyl-(1$\rightarrow4)-\beta-D-glucopyranosyl-(1\rightarrow6)-\beta$-D-glucopyranosyl ester.

• 생약학회지
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• 제51권2호
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• pp.93-99
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• 2020

This study was performed to find anti-inflammatory or antitumor compounds from the polar fraction obtained from the extract of Clinopodium chinense var. shibetchense (H. Lev) Koidz (Labiatae). Chromatography of the BuOH fraction yielded two flavonoid glycosides (compounds 1 and 2) and two saponins (compounds 3 and 4). On the basis of spectroscopic data, compounds 1 and 2 were identified to be ponciretin 7-O-α-L-rhamnopyranosyl-(1→6)-α-D-glucopyranoside (neoponcirin) and naringenin 7-O-α-L-rhamnopyranosyl-(1→6)-α-D-glucopyranoside (isonaringin). Compounds 3 and 4 were identified to be 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl}-saikogenin F (buddlejasaponin IV) and 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl}-21β-hydroxysaikogenin F (clinoposaponin XV). In addition, ursolic acid (5) was isolated and identified from the CHCl₃ fraction. Inducible nitric oxide synthase (iNOS) assay and sulforhodamine B (SRB) assay were performed to lead a potential anti-inflammatory or anti-tumor compounds from C. chinense var. shibetchense. Of the four compounds (1 - 4), compound 3 considerably inhibited cancer cell growth and NO production (IC₅₀s, 5.59 μM in iNOS assay and 6.62 - 14.88 μM in SRB assay).

• Journal of the Korean Wood Science and Technology
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• 제37권3호
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• pp.239-244
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• 2009

본 연구에서는 느티나무 심재부에서 단리한 7-hydroxy-3-methoxycadalene이 나타내는 세포독성을 경감시키고 물에 대한 낮은 용해도를 향상시킬 목적으로 반응물의 7번 위치에 존재하는 수산기를 친수성이 강하고 세포 독성이 없는 글루코오스로 치환시켜 7-O-${\beta}$-D-glucopyranosyl -3-methoxycadalene을 합성하였으며, 수율은 약 55%에 이르렀다. 7-O-${\beta}$-D-glucopyranosyl -3-methoxycadalene은 반응 전 7-hydroxy-3-methoxycadalene에 비해 물에 대한 수용성이 크게 증가하였다. 카달렌-글루코오스 유도체는 정상 폐조직 세포(WI-38 cell line)와 폐암 세포주(A-549 cell line)에 대한 세포생존율, 즉 반수치사율(IC50)이 각각 $298.2{\mu}m$과 $88.6{\mu}m$로 나타났다. 이러한 결과는 7-hydroxy-3-methoxycadalene에 글루코오스 한 분자를 치환함으로써 폐암세포의 증식억제에 미치는 약리적 효과가 3배 이상으로 향상되었음을 의미한다.

• Bulletin of the Korean Chemical Society
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• 제31권10호
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• pp.2786-2790
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• 2010

Three new oleanane-type triterpene saponins (1, 2 and 3) were isolated from aerial parts of Gladiolus gandavensis, along with two known compounds (4 and 5). Their structures were elucidated as 29-O-($\beta$-D-glucopyranosyl)-$2{\beta}$,$3{\beta}$-dihydroxyolean-12-en-28-oicacid(1), 3-O-($\beta$-D-xylopyranosyl)-29-O-($\beta$-D-glucopyranosyl)-12-en-28-oic acid (2), and $2{\beta}$,$3{\beta}$,29-trihydroxyolean-12-en-28-oic acid 28-O-[$\beta$-D-glucopyranosyl($1{\rightarrow}2$)-($\alpha$-L-rhamnopyranosyl($1{\rightarrow}6$))-$\beta$-D-glucopyranosyl] ester (3), by spectroscopic methods, and by comparison with known analogues. These oleanane-type triterpene saponins glycosidated at C-29 were not obtained frequently.

• Archives of Pharmacal Research
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• 제23권6호
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• pp.568-573
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• 2000

A reversed-phase high-performance liquid chromatographic method was developed to determine the optical purity of bevantolol enantiomers. (S)-(-)-Menthyl chloroformate((-)-MCF), (S)-(-)-$\alpha$-methylbenzyl isocyanate((-)-MBIC) and 2,3,4,6-tetra-O-acetyl-$\beta$-D-glucopyranosyl isothiocyanate(GITC), which can react with the secondary amine group of bevantolol were investigated as chiral derivatization reagents. Among them indirect chiral HPLC method using CITC gave the best result. The derivatization proceeded quantitatively within 20 min at room temperature. Separation of the enantiomers as diastereomers was achieved by reversed-phase HPLC within 20min using ODS column. Different ratios of (S)-(-)-bevantolol and (R)-(+)-bevantolol were prepared. Enantiomeric separation of these mixtures took place on a chiralcel OD column or, after derivatization with GITC, on a ODS column. No racemization was found during the experiment. This method allowed determination of 0.05% of either enantiomer in the presence of its stereoisomer and method validation showed adequete linearity over the required range.

• 생약학회지
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• 제31권1호
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• pp.34-38
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• 2000

Three compounds were isolated from the roots of Astragalus membranaceus (Leguminosae). On the basis of spectroscopic evidences, the structures were characterized as $3-0-{\beta}-D-xylopyranosyl-(2',3'-O-diacetyl)-6-0-{\beta}-D-glucopyranosyl-3{\beta},6{\alpha},16{\beta},25-tetrahydroxy-20(R)$,24(S)-epoxy-cycloartane(Astragaloside I), $3-0-{\beta}-D-xylopyranosyl-(2'-O-acetyl)-6-0-{\beta}-D-glucopyranosyl-3{\beta},6{\alpha},16{\beta},25-tetrahydroxy-20(R)$,24(S)-epoxy-cycloartane(Astragaloside II), $3-0-{\beta}-D-xylopyranosyl-(2',4'-O-diacetyl)-6-0-{\beta}-D-glucopyranosyl-3{\beta},6{\alpha},16{\beta},25-tetrahydroxy-20(R)$,24(S)-epoxycycloartane(Isoastragaloside I). Full data of NMR including HMBC and 1D-TOCSY experiment of these compounds were reported for the first time.

• Journal of Microbiology and Biotechnology
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• 제11권2호
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• pp.242-250
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• 2001

A Gram-positive bacterium (strain JB-13) that was isolated from soil as a producer of cyclodextrin glucanotransferase (CGTase) [EC 2.4.1.19] was identified as Panibacillus sp. JB-13. This CGTase could catalyze the transglucosylation reaction from soluble starch to L-ascorbic acid (AA). A main product formed by this enzyme with ${\alpha}-glucosidase$ was identified as $2-O-{\alpha}-D-glucopyranosyl{\;}_{L}-ascorbic$ acid (AA-2G) by the HPLC profile and the elemental analysis. CGTase was purified to homogeneity using ammonium sulfate fractionation, ion-exchange chromatography on DEAE-Seohadex A-50, and gel chromatography on Sephacryl S-200HR. The molecular weight was determined to be 66,000 by both gel chromatography and SDS-PAGE. The isoelectric point of the purified enzyme was 5.3. The optimum pH and temperature was PH 7.0 and $45^{\circ}C$ respectively. The enzyme was stable in the range of pH 6-9 and at temperatures of $75{\circ}C$ or less in the presence of 15 mM ${CaCl_2}.\;{Hg^2+},\;{Mn^+2},{Ag^+},\;and\;{Cu^2+}$ all strongly inhibited the enzyme's activity.

• Archives of Pharmacal Research
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• 제22권3호
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• pp.317-319
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• 1999

Anticomplementary activity of hederagenin and related saponins isolated from Dipsacus asper was investigated in vitro. HN saponin F (3) was most potent with $IC_{50}$ value of$ 3.7{\times}10^{-5} M$ followed by 3-O-${\beta}-D-glucopyranosyl-(1{\rightarrow} 3)-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)-{\beta}-L-arabinopyranosyl$ hederagenin $28-O-{\beta}-D-glucopyranosyl-(1{\rightarrow}6)-beta$-D-glucopyrano side (8), $3-O-{\beta}-L-arabinopyranosyl$ hederagenin $28-O-{\beta}-D-glucopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (5), dipsacus saponin A (4), and hederagenin (1) on the classical pathway (CP) of complement system, while the saponins 3-5 did not show the inhibition of hemolysis and rather increase the hemolysis on the alternative pathway (AP). However, all of C-3 monodesmosides [prosapogenin CP (2), dipsacus saponin B (6), and dipsacus saponin C (7)] evoked hemolysis directly on the erythrocytes.