• Bulletin of the Korean Chemical Society
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• v.29 no.3
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• pp.551-554
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• 2008

An improved HPLC method for the separation of madecassoside isomers (madecassoside and asiaticoside-B) has been developed. The isomers can be separated with high resolution from extracts of Centella asiatica by HPLC using $\beta$-cyclodextrin as a mobile phase added on a $C_{18}$ column. The result shows that the isomers can be separated with a mobile phase consisting of methanol:water (50:50, v/v) with 4 mmol/L $\beta$-CD. To elucidate the mechanism of the separation of madecassoside and asiaticoside-B, this paper studied the separation of their aglycon parts (madecassic acid and terminolic acid), another pair of isomers. The isomers can also be separated with high resolution with a mobile phase consisting of methanol:water (65:35, v/v) with 4 mmol/L $\beta$-CD and the pH of the mobile phase was adjusted to 4. The paper also studied the separation of the two isomers by HPLC using $\alpha$-CD and Glucosyl-$\beta$-CD as a mobile phase additive in order to elucidate the mechanism of the separation process.

• Journal of Microbiology and Biotechnology
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• v.26 no.11
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• pp.1918-1923
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• 2016

Two baicalein derivatives, baicalin and oroxylin A, were synthesized in this study. These derivatives exhibit diverse biological activities, such as anxiolytic and anticancer activities as well as memory enhancement. In order to synthesize baicalin from aglycon baicalein using Escherichia coli, we utilized a glycosyltransferase that regioselectively transfers glucuronic acid from UDP-glucuronic acid to the 7-hydroxy group of baicalein. To increase baicalin productivity, an araA deletion E. coli mutant, which accumulates UDP-glucuronic acid, was used, and ugd, which converts UDP-glucose to UDP-glucuronic acid, was overexpressed. Using these strategies, approximately $720.3{\mu}M$ baicalin was synthesized from $1,000{\mu}M$ baicalein. Oroxylin A was then synthesized from baicalein. Two O-methyltransferases (OMTs), ROMT-15 and POMT-9, were tested to examine the production of oroxylin A from baicalein. E. coli harboring ROMT-15 and E. coli harboring POMT-9 produced reaction products that had different retention times, indicating that they are methylated at different positions; the structure of the reaction product from POMT-9 was consistent with oroxylin A, whereas that from ROMT-15 was 7-O-methyl baicalein. Using E. coli harboring POMT-9, approximately 50.3 mg/l of oroxylin A ($177{\mu}M$) was synthesized from 54 mg/l baicalein ($200{\mu}M$).

• Bulletin of the Korean Chemical Society
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• v.30 no.8
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• pp.1811-1816
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• 2009

An extensive phytochemical investigation of the polar fractions of a methanolic extract of Egyptian medicinal food, black cumin (seeds of Nigella sativa L.) led to the isolation of two new triterpene saponins, named sativosides A and B (1-2), along with four known saponins (3-6). Sativoside A (1) is the first example of saponins containing 18-ene triterpene aglycon not only in this Nigella genus but also in the family Ranunculaceae. The structure of the new saponins was elucidated mainly by a combination of 1D and 2D NMR data, together with HRFABMS and acid hydrolysis. Three compounds (1-3) showed the significant inhibition effect of phorbol 12-myristate 13-acetate (PMA) plus calcium ionophore A23187-induced production of IL-6 in a human mast cell (HMC-1) line.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.48 no.5
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• pp.392-396
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• 2003

Maysin, a C-glycosylflavone, was isolated from the silks of maize, Zea mays L. The ESI mass spectrum indicates that molecular weight of maysin is $577\textrm{M}^+$m/z, and the ether-linked sugar is rhamnose, $431\textrm{M}^+$m/z (MW$^{+}$-146). The DPPH (1,1-Diphenyl-2-picrylhydrazyl) radical scavenging activity of maysin was higher than that of rutin. However, as compared with its aglycon luteolin, maysin showed the relatively moderate DPPH scavenging activity mainly due to the glycosylation of two sugars moieties, keto-fucose and rhamnose. In the in vitro cytotoxicity test against the five human tumor cell lines such as lung (A549), ovarian (SK-OV-3), melanoma (SK-MEL-2), central nerve system (XF-489), and colon (HCT-15), maysin exhibited the relatively weaker activities than cisplatin. The $\textrm{ED}_{50}$ values of maysin were 62.24, 43.18, 16.83, 37.22, and 32.09/$m\ell$, respectively. Result suggests that maysin is a potential cytotoxicity compound, particularly for human colon, central nerve system, and melanoma tumors.s.

• Journal of Microbiology and Biotechnology
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• v.18 no.5
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• pp.866-873
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• 2008

2-Deoxystreptamine is a core aglycon that is vital to backbone formation in various aminoglycosides. This core structure can be modified to develop hybrid types of aminoglycoside antibiotics. We obtained three genes responsible for 2-deoxystreptamine production, neo7, neo6, and neo5, which encode 2-deoxy-scyllo-inosose synthase, L-glutamine: 2-deoxy-scyllo-inosose aminotransferase, and dehydrogenase, respectively, from the neomycin gene cluster. These genes were cloned into pIBR25, a Streptomyces expression vector, resulting in pNDOS. The recombinant pNDOS was transformed into a non-aminoglycoside-producing host, Streptomyces venezuelae YJ003, for heterologous expression. Based on comparisons of the retention time on LC-ESI/MS and ESI-MS data with those of the 2-deoxystreptamine standard, a compound produced by S. venezuelae YJ003/pNDOS was found to be 2-deoxystreptamine.

• Korean Journal of Pharmacognosy
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• v.50 no.2
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• pp.124-132
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• 2019

This study compared the contents of phenolic components depending on the extracting conditions of Acanthopanax koreanum stem to provide basic information for developing Acanthopanax koreanum-based functional foods. Our findings show that the content of total phenolic component peaked at 16 hours of extraction (WAK-16, 7.22%) and when water extracted at $100^{\circ}C$. However, 11-hours water extraction (WAK-11) showed highest eleutheroside B concentration of 1.32%, a main component of A. koreanum, and the level of chlorogenic acid concentration was the highest when 1-hour water extraction (WAK-1) was conducted, being 2.12%. Moreover, highest concentration of eleutheroside E was observed in 16-hours water extraction (WAK-16) as 1.49%. With 60-hours water extraction (WAK-60), the content of syringaresinol, an active phenolic aglycon substance, concentration was the highest with the value of 0.10%. Isofraxidin showed the highest concentration of water extract(0.09%) for 20 hours (WAK-20) and 0.42% for sinapyl alcohol[16 hours (WAK-16)].

• Journal of Ginseng Research
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• v.47 no.5
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• pp.605-614
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• 2023

Ginsenosides are bioactive components of Panax ginseng with many functions such as anti-aging, anti-oxidation, anti-inflammatory, anti-fatigue, and anti-tumor. Ginsenosides are categorized into dammarane, oleanene, and ocotillol type tricyclic triterpenoids based on the aglycon structure. Based on the sugar moiety linked to C-3, C-20, and C-6, C-20, dammarane type was divided into protopanaxadiol (PPD) and protopanaxatriol (PPT). The effects of ginsenosides on skin disorders are noteworthy. They play antiaging roles by enhancing immune function, resisting melanin formation, inhibiting oxidation, and elevating the concentration of collagen and hyaluronic acid. Thus, ginsenosides have previously been widely used to resist skin diseases and aging. This review details the role of ginsenosides in the anti-skin aging process from mechanisms and experimental research.

• Korean Journal of Microbiology
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• v.29 no.2
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• pp.85-91
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• 1991

.betha.-1,4-D-Glucan glucanohydrolase(EC 3.2.1.4;F-II-IV) purified from Trichoderma koningii was identified as a glycoprotein containing 9% carbohydrate. Isoelectric point of the enzyme was estimated to be 4.9 and molecular weight was determined to be approximately 58,000. The porducts of p-nitrophenyl-cellobioside ($PNPG_{2}$) catalyzed by the enzyme were p-nitrophenol(PNP) and p-nitrophenyl-glucoside($PNPG_{1}$). The Km value for $PNPG_{2}$ was estimated to be 0.97 mM in case of the holoside lindage and 10.4 mM in case of the aglycon linkage and their kcat values were $1.8*10^{5}$$ min^{-1}$ and $7.5*10^{5}$ $min^{-1}$ respectively. The product of p-nitrophenyl cellotriose($PNPG_{3}$) was only $PNPG_{1}$. The Km value for $PNPG_{3}$ was 69.5 .$\mu$M and kcat was $1*10^{8}$ $min^{-1}$ which implicates that the enzyme have higher affinity and higher hydrolysis rate toward $PNPG_{3}$ than toward $PNPG_{2}$. The enzyme showed its optimal activity at pH 4.0-4.5 and at 60.deg.C. The effect of gluconolactone on the activity toward $PNPG_{2}$ showed competitive inhibition pattern but glucose and cellobiose did not. The enzyme contained a high content of acidic and hydroxylated amino acids in contrast to basic amino acids.

• Korean Journal of Medicinal Crop Science
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• v.16 no.5
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• pp.332-336
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• 2008

PPD ginsenosides in ginseng leaf were analyzed to determine effects of either FIR heat or steaming heat treatment. Among the PPD ginsenosides, Rb1, Rc and Rb3 forming four glycoside-attached aglycons were increased as FIR heat temperatures were increased from 60 to $120^{\circ}C$, while Rb3 was decreased. In addition, FIR heat treatment was effective to increase Rd forming a three glycoside-attached aglycon. Rg3 and Rh2 were not increased by the FIR heat treatment. In steaming heat treatment, Rb1 was significantly decreased, while Rb2 was increased. Rd was also increased by increased steaming temperature, yet its content was lower than in the FIR heat treatment. However, the steaming heat treatment increased yields of Rg3 and Rh2, which were not observed in the FIR heat treatment. Thus, FIR heat treatment was beneficial to efficient products of Rb1, Rc, Rb3 and Rd. Steaming heat treatment was effective to higher collection of Rb2, Rg3 and Rh2.

• Journal of Microbiology and Biotechnology
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• v.28 no.6
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• pp.931-937
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• 2018

Glycosyltransferases (GTs) from microbes are an emerging and rich source for efficient glycol-transformation of natural/unnatural compounds. Here, we probed the catalytic capability and substrate promiscuity of BmmGT1 from marine-derived Bacillus methylotrophicus B-9987. The regioselectivity of BmmGT1 on macrolactin A (1) was explored by optimization of the reaction conditions, in which a series of O-glycosylated macrolactins (1a-1e) were generated, including two new di/tri-O-glucosyl analogs (1b and 1e). Furthermore, BmmGT1 was able to catalyze the glycosylation of the thiol (S-) or amine (N-) sites of phenolic compounds (2 and 3), leading to the generation of N- (2a) or S-glycosides (3a and 3b). The present study demonstrates that BmmGT1 could serve as a potential enzyme tool for O-, N-, or S-glycosyl structural diversification of compounds for drug discovery.