• Journal of Microbiology and Biotechnology
• /
• v.30 no.6
• /
• pp.946-954
• /
• 2020

Platycodon grandiflorum root (Platycodi radix) saponins, platycosides, have been used as health supplements and food items for the treatment of respiratory disorders and pulmonary diseases. Deglycosylated saponins have been known to exert stronger biological effects than their glycosylated forms. In the present study, glycosylated platycosides in Platycodi radix extract were biotransformed into deglycosylated 3-O-β-ᴅ-glucopyranosyl platycosides, including 3-O-β-ᴅ-glucopyranosyl platycodigenin, 3-O-β-ᴅ-glucopyranosyl polygalacic acid, and 3-O-β-ᴅ-glucopyranosyl platyconic acid, by pectinase from Aspergillus aculeatus. This is the first report on the quantitative enzymatic production of 3-O-β-ᴅ-glucopyranosyl platycosides. The chemical structures of 3-O-β-ᴅ-glucopyranosyl platycosides were identified with LC/MS. Moreover, the biotransformation pathways of the three types of platycosides in Platycodi radix into 3-O-β-ᴅ-glucopyranosyl platycosides were established.

• Archives of Pharmacal Research
• /
• v.22 no.4
• /
• pp.428-431
• /
• 1999

Seven known oleanolic acid glycosides (1-7) were isolated form the MeOH extract of Tiarella polyphylla. The structures were identified to be 3-O-($\beta$-glucopyranosyl) oleanolic acid (1), 3-O-[$\beta$-D-glucopyranosyl-(1 3)-$\beta$-D-glucopyranosyl] oleanolic acid (2), 3-O-D-[$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glycopyranosyl] oleanolic acid (3), 3-O-[$\beta$-D-glucopyranosyl-(1 3)-$\beta$-D-glucopyranosyl] oleanolic acid 28-O-$\beta$D-glucopyranosyl ester (4), 3-O-[$\beta$-D-glucopyranosyl-(1 2)-$\beta$-D-glucopyranosyl] oleanolic acid 28-O-$\beta$-D-glucopyranosyl ester (5), 3-O-[a-L-rahmnopyranosyl-(1 3)-$\beta$-D-glucururonopyranosyl] oleanolic acid (6), and 3-O-[$\alpha$-L-rhamnopyranosyl-(1 3)-$\alpha$-D-glucuronopyranosyl] oleanolic acid 28-O-$\alpha$-D-glucopyranosyl ester (7) on the basis of physicochemical and spectral data. These triterpene glycosides were tested for the anti-complement activity and hemolytic activity. Bisdesmosidic saponins, 4, 5, and 7, showed anti-complement activity; in contrast, monodesmosidic saponins, 1-3, and 6, showed direct hemolytic activity. Methyl esterified monodesmosidic saponins showed anti-complement activity at a low concentration and hemolytic activity at a high concentration.

• Archives of Pharmacal Research
• /
• v.22 no.4
• /
• pp.423-427
• /
• 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.

• Korean Journal of Pharmacognosy
• /
• v.23 no.4
• /
• pp.221-224
• /
• 1992

From the roots of Angelica dahurica Bentham et Hooker(Umbelliferae), three coumarin glycosides have been isolated and identified as skimmin, $8-O-{\beta}-D-glucopyranosyl$ xanthotoxol and $tert.-O-{\beta}-D-glucopyranosyl-heralenol$. $8-O-{\beta}-D-Glucopyranosyl-xanthotoxol$ was isolated for the first time from plant source.

• Korean Journal of Pharmacognosy
• /
• v.30 no.2
• /
• pp.168-172
• /
• 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.

• YAKHAK HOEJI
• /
• v.54 no.6
• /
• pp.441-448
• /
• 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 $0.026{\pm}0.012%$.

• Journal of the Korean Wood Science and Technology
• /
• v.35 no.6
• /
• pp.135-144
• /
• 2007

The dried barks of Maackia amurensis were ground, extracted with 95% EtOH, concentrated, and fractionated with a series of light petroleum ether, dichloromethane, ethyl acetate and water on a separatory funnel. Each fraction was concentrated, then a portion of dichloromethane and ethyl acetate soluble was chromatographed on a Sephadex LH-20 and silica gel 60 column using a various solvent system as eluents. The isolated compounds were identified by cellulose TLC, $^1H-$, $^{13}C-NMR$, COSY, NOESY, HMQC, HMBC, FAB and EI-MS. The structures were determined as: 7-O-$\beta$-D-glucopyranosyl-4'-methoxyisoflavone, 7-O-$\beta$-glucopyranosyl(1'''->6'')-$\beta$-D-glucopyranosyl-4'-methoxyisoflavone, 7-O-$\beta$-D-glucopyranosyl(1''''->6''')-$\beta$-D-glucopyranosyl(1'''->6'')-$\beta$-D-glucopyransoyl-4'-methoxyisoflavone, 7-O-$\beta$-D-glucopyranosyl-4', 6-dimethoxyisoflavone. The Free radical scavenging activity using DPPH of the isolated compounds were similar with that of BHT but lower than of $\alpha$-tocopherol.

• Applied Biological Chemistry
• /
• v.43 no.2
• /
• pp.136-140
• /
• 2000

Two steroidal saponins were isolated from MeOH extract of the rhizomes of Asparagus oligoclonos. Using the spectroscopic techniques of $^1H,\;^{13}C$ NMR and 2D NMR, they were identified as $3-O-[{\beta}-D-glucopyranosyl-(1{\rightarrow}2)-{\beta}-D-glucopyranosyl]-(25S)-spirostan-3{\beta}-ol$ and $3-O-{{\beta}-D-glucopyranosyl-(1{\rightarrow}2)-[{\beta}-D-xylopyranosyl-(1{\rightarrow}4)]-{\beta}-D-glucopyranosyl}-(25S)-spirostan-3{\beta}-ol$, respectively. They were first isolated from A. oligoclonos. The in vitro antibacterial activities as well as antibacterial spectrums against 20 bacteria strains were investigated with MIC test. Both saponins inhibited the growth of 10 bacteria strains at the concentration of$100\;{\mu}g/ml$.

• Korean Journal of Plant Resources
• /
• v.9 no.1
• /
• pp.55-62
• /
• 1996

The caffeic acid, 4-O-$\beta$-D-glucopyranosyl caffeic acid, 4-O-$\beta$-D-glucopyranosyl-$\rho$-coumaric acid and 7-O-$\beta$-D-glucuronide of ($\pm$)-eriodictyol have been isolated from the root of Vitis thunbergii var. sinuata. The structures of compounds were determined by chemical and spectroscopic methods.

• Journal of the Korean Chemical Society
• /
• v.23 no.1
• /
• pp.46-51
• /
• 1979

Condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-${\beta}$-D-glucopyranosyl bromide (2) with 1,2;3,4-di-O-isopropylidene-${\alpha}$-D-galactopyranose (3) in the presence of silver triflate and syn-collidine gave 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) in $86{\%}$ yield. Cleavage of phthalimido group and de-O-acetylation with hydrazine, acetylation, and hydrolysis of isopropylidene and O-acetyl groups furnished 6-O-(2-acetamido-2-deoxy-${\beta}$-D-glucopyranosyl)-D-galactopyranose (1) with overall yield of $65.8{\%}$ starting from 3. Some other derivatives of 1 which have free hydroxyl groups at the specific position have also been prepared from 4. These compounds could be used as precursors for further glycosidation reactions.