• Journal of the Korean Chemical Society
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• v.55 no.6
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• pp.988-993
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• 2011

Cyclodehydration of 6-amino-5-cyano pyrimidine derivative (2) afforded pyrimidoisoindole derivatives (3). Compound (3) reacted with carbethoxymethylene derivative to give pyridopyrimidine derivatives (5a,b). Compound (3) was also reacted with formamide to give the corresponding pyrimidopyrimdine derivatives (6) that condensed with benzaldehyde to give Schiff's base (7). Refluxing of compound (3) with triethyl orthoformate afforded compound (8) that cyclized with ammonium hydroxide giving the same compound (6). Compound (8) cyclized with hydrazine hydrate giving compound (9) which also cyclized with triethyl orthoformate affording compound (10). Diazotization of compound (3) led to the formation of triazinopyrimidine derivative (11). Cyclization of compound (11) upon treatment with hydrazine hydrate afforded compound (12). Compound (15) was prepared from reaction of compound (3) and ethylenediamine in presence of carbon disulfide. The behaviour of compound (15) toward benzoyl chloride, triethyl orthoformate, nitrous acid and/or carbon disulfide was also described. All proposed structures were supported by elemental analyses, spectroscopic data and some of the new products showed antimicrobial activity.

• Journal of Ginseng Research
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• v.37 no.4
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• pp.451-456
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• 2013

Compound K is a major metabolite of ginsenoside Rb1, which has various pharmacological activities in vivo and in vitro. However, previous studies have focused on the pharmacokinetics of a single metabolite or the parent compound and have not described the pharmacokinetics of both compounds in humans. To investigate the pharmacokinetics of ginsenoside Rb1 and compound K, we performed an open-label, single-oral dose pharmacokinetic study using Korean Red Ginseng extract. We enrolled 10 healthy Korean male volunteers in this study. Serial blood samples were collected during 36 h after Korean Red Ginseng extract administration to determine plasma concentrations of ginsenoside Rb1 and compound K. The mean maximum plasma concentration of compound K was $8.35{\pm}3.19$ ng/mL, which was significantly higher than that of ginsenoside Rb1 ($3.94{\pm}1.97$ ng/mL). The half-life of compound K was 7 times shorter than that of ginsenoside Rb1. These results suggest that the pharmacokinetics, especially absorption, of compound K are not influenced by the pharmacokinetics of its parent compound, except the time to reach the maximum plasma concentration The delayed absorption of compound K support the evidence that the intestinal microflora play an important role in the transformation of ginsenoside Rb1 to compound K.

• Korean Journal of Food Science and Technology
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• v.35 no.5
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• pp.959-967
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• 2003

The polyphenol compounds of Korean pears were extracted with 60% acetone for 4 days at room temperature and purified using Sephadex LH-20 column chromatography, MCI gel column chromatography, Bondapak $C_{18}$ column chromatography, TLC, and HPLC. As a result, three compounds were isolated. The chemical structures of each compound were determined and identified using NMR, FAM-mass, and FT-IR. The compounds were confirmed as (+)-catechin (compound A), (+)-gallocatechin (compound B), (-)-epigallocatechin (compound C), and procyanidin B-3-3-o-gallate (compound D).

• Journal of the Korean Applied Science and Technology
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• v.38 no.6
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• pp.1466-1475
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• 2021

Compound K (20-O-β-(_D-glucopyranosyl)-20(S)-protopanaxadiol) is an active ingredient of ginsenosides. Compound K has been known to produce from biotransformation by β-glucosidase action of human intestinal microbes after oral admistration of ginseng. We have investigated the cytotoxicity of compound K obtained from bio-converted ginseng extract. As a result, compound K showed no significant cytotoxicity in the concentration of 0.001 to 1 ㎍/mL and inhibited the production of TNF-α, MCP-1, IL-6 and NO in RAW 264.7 cells induced by LPS inflamation. In the same concentration, HaCaT cells induced by inflammation with TNF-α and IFN-γ decreased IL-8 production due to compound K treatment. In the brine shrimp lethality assay, the LC₅₀ of compound K was 0.37 mg/mL indicating some toxicity, but the bioconverted product containing 35% compound K showed relatively low toxicity with an LC₅₀ of 0.87 mg/mL. These results suggest that the compound K enriched extract is a potential functional material for acne relief cosmetic products.

• Journal of the Korean Applied Science and Technology
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• v.38 no.5
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• pp.1335-1344
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• 2021

Ginsenoside Compound K is a triterpene saponin found in the leafs, stems and roots of Panax ginseng. This study aimed to prepare a valuable ginsenoside Compound K using ginseng extracts with the enzyme(Plantase). Plantase showed very efficient activity to produce Compound K from ginseng extracts. Plantase exhibited the highest activity at pH 5 and 50 ℃, as a result of investigating the yield of Compound K by changing the temperature and pH, while fixing the enzyme concentration to 10% or 15% over 48 hours of reaction time. Under optimium conditions, Plantase produced and accumulated Compound K over 35 wt% of whole ginseng extracts. Antimicrobial activitiy of bioconvertied ginseng extracts showed selectivity against Cutibacterium acnes KCTC 3314. Minimal inhibitory concentration (MIC) of bioconverted ginseng extract (35% of Compound K enriched extract) against Cutibacterium acnes KCTC 3314 strain is 31.25ug/mL. These results suggest that the Compound K enriched extract is potential materials for cosmetic products and Plantase is a very useful enzyme for Compound K production.

• Korean Journal of Food Science and Technology
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• v.34 no.3
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• pp.493-497
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• 2002

The polyphenol compounds of Korea ginseng radix were extracted with 60% acetone for 4 days at room temperature and purified using Sephadex LH-20 column chromatography, MCI gel column chromatography, Bondapak $C_{18}$, column chromatography, TLC and HPLC. As a result in three compounds were isolated from Korean ginseng. In the inhibitory activities of angiotensin converting enzyme, compound Ⅱ showed the highest value of 31.86% inhibition at 157 ppm. Compound I showed 19.4% inhibition at 157 ppm. In the inhibitory activities of xanthine oxidase, compound I, II showed complete inhibition at 666 ppm but compound III didn't have inhibitory activity. In the inhibitory activities of tyrosninase, compound III showed 6.1% inhibition at 300 ppm and 28.6% at 400 ppm.

• Natural Product Sciences
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• v.10 no.6
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• pp.347-352
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• 2004

When saponin extracts of dried ginseng and red ginseng were anaerobically incubated with human intestinal microflora, these extracts were metabolized to compound K and ginsenoside $Rh_2$, respectively. However, when these extracts were incubated with commercial lactic acid bacteria, these did not metabolize these ginsenosides to compound K or ginsenoside $Rh_2$. Among some intestinal bacteria isolated from human feces, Bacteroides C-35 and C-36 transformed these saponin extracts to compound K and ginsenoside $Rh_2$, respectively. These bacteria also transformed water extracts of dried ginseng and red ginseng to compound K and ginsenoside $Rh_2$, respectively, similarly with that of the saponin extracts. Among transformed ginsenosides, compound K and 20(S)-ginsenoside $Rh_2$ exhibited the most potent cyotoxicity against tumor cells.

• Food Quality and Culture
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• v.1 no.1
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• pp.18-21
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• 2007

The objective of this study was to prepare bioactive ginseng yogurts containing compound K, which is transformed from ginsenosides, and to investigate the compound's cytotoxicity against tumor cells. Milk containing ginseng was fermented by Bifidobacteria KK-I and KK-2, and their activities for transforming ginsenosides to compound K were measured. Among the tested concentrations of ginseng in the milk, compound K was effectively produced in the 3% and 6% ginseng yogurts fermented for 48 hrs. These fermented ginseng yogurts were extracted with BuOH, and their cytotoxicities against tumor cells were examined. The BuOH extract of the yogurt made from the 3% ginseng milk showed cytotoxic activity against P388 and HeLa tumor cells. However, the nonfermented ginseng milk did not exhibit cytotoxicity against these cells. Therefore, we deem that the ginseng yogurt, which contained compound K, could be developed as a potential fermented drink product.

• Proceedings of the SCSK Conference
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• 2003.09a
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• pp.741-762
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• 2003

Ginsenosides, the major active ingredients of ginseng, show a variety of biomedical efficacies such as anti-aging, anti oxidation and anti-inflammatory activities. To understand the effects of compound K (20-O-D-glucopyranosyl-20 (S)-protopanaxadiol), one of the major metabolite of ginsenosides on the skin, we assessed the expression level of ∼ 100 transcripts in compound K-treated HaCaT cells using cDNA microarray analysis. Compound K treatment induced differential expression of 21 genes, which have been reported to be involved in the organization of ECM structure as well as defense responses in human skin cells. One of the most interesting findings is 2-fold increase in hyaluronan synthase2 (HAS2) gene expression by compound K. We found that change in expression of HAS2 gene represents a specific response of HaCaT cells to compound K because hyaluronan synthase 1, 3 was not changed by treatment with compound K. We also demonstrated that the compound K effectively induced hyaluronan synthesis in human skin cells and hairless mouse skin. The human clinical study indicates that topical application of compound K-containing oil-in-water emulsion showed improvement of xerosis, wrinkle and fine lines in the aged skin. We concluded that compound K has anti-aging effects by the induction of HAS2 gene expression and following hyaluronan synthase.

• Food Science and Biotechnology
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• v.17 no.4
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• pp.805-808
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• 2008

Ginsenosides are responsible for the pharmacological and biological activities of ginseng. In this study, ginsenoside Rh1 and compound K were isolated and purified from fermented ginseng substrate and their anti-allergic effects were assessed in compound 48/80-induced anaphylactic shock model. The fermented ginseng substrate was extracted by methanol and ginsenoside Rh1 and compound K were efficiently purified by preparative high performance liquid chromatography (prep HPLC). Their quality and quantity were analyzed by liquid chromatography-mass spectrometer (LC-MS) and HPLC. Ginsenoside Rh1 showed better anti-allergic effects than compound K in compound 48/80-induced anaphylactic shock model. This study suggested that fermented ginseng extracts with enriched Rh1 may be utilized as a potential biomaterial of functional food for the alleviation of allergic symptoms.