• Archives of Pharmacal Research
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• 제19권5호
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• pp.429-431
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• 1996

A new cycloartane glycoside (1) was isolated from the aerial part of Thalictrum uchiyamai Nakai (Ranunculaceae). On the basis of chemical and physicochemical evidence, the aglycone structure of this compound was characterized as 116, 25-dihydroxy-3, 24-diacetoxy-9, 19-cycloartane-29-oic acid, a new derivative of cycloartane triterpene. Also the oli-gosaccharide moiety of this glycoside were determined as 29-O-${alpha}$-L-rhanmnopyranosyl- ($1rightarrow2$)-[${beta}$-D-xylofuranosyl-($1rightarrow6$)-${beta}$-D-glucopyranose by application of HMBC technoque. Consequently, the structure of compound 1 was elucidated as 29-O-${alpha}$-L-rhanmnopyranosy-($1rightarrow2$)-[${beta}$-D-xylofuranosyl-($1rightarrow6$)-${beta}$-D-glucopyranosyl-16, 25-dihydroxy-3, 24-diacetoxy-9, 19-cycloartane-29-oic acid ester.

• 공업화학
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• 제9권6호
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• pp.842-845
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• 1998

디히드록시 화합물과 oxalyl chloride의 반응에 의해 4가지 새로운 lactone류와 ${\alpha}$,${\omega}$-dibromo 화합물과의 반응에 의해 dibenzo crown ether를 합성하였다. 5,6,11,12- Tetracarbonyl-2,2,3,3,8,8,9,9-octaphenyl-1,4,7,10-tetraoxacyclododecane(1), 5,6,11,12- tetracarbonyl-2,2,3,3,8,8,9,9-octamethyl-1,4,7,10-tetraoxacyclododecane(2), 7,8,15,16- tetracarbonyl-1,6,9,14-tetraoxacylclohexadecane(3), 5,6,11,12-tetracarbonyl-2,3,8,9- tetraphenyl-1,4,7,10-tetraoxacyclododecane(4)는 pyridine 존재 하에서 각각 benzopinacol, pinacol, 2,2'-dihydroxybiphenyl, hydrobenzoin과 oxalyl chloride의 반응에 의해 합성하였다. Dibenzo-13-crown-4(5)는 catechol과 1,3-dibromopropane/1,2-dibromoethane의 반응에 의해 각각 25%, 12%, 20%, 75%, 25%의 수율로 합성하였다.

• 생명과학회지
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• 제16권4호
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• pp.647-652
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• 2006

마속 식물들은 오래 전부터 다양한 민간처방에 사용되어 왔으며, 재배마의 근경은 다양한 생리활성물질들이 보고되어, 건강식품으로 인식되고 있다. 재배마의 주아는 매년 2,000톤 이상 생산되고 있으나, 다음해의 종자로 일부 이용될 뿐 거의 폐기되고 있으며, 생리활성에 대한 보고도 거의 없는 실정이다. 본 연구에서는 마의 주아로부터 3종의 phenanthrene 및 2종의 phenanthraquinone를 분리하였으며, 이들의 구조를 규명하였다. 이들 중 6-hydroxy-2,7-dimethoxy-1,4-phenanthraquinone은 처음으로 분리 되었다. 분리된 5종을 대상으로 항균활성을 평가한 결과, 6,7-dihydroxy-2,4-dimethoxyphenanthrene은 Candida albicans에 대해 $25\;{\mu}g/ml$의 MIC와 MFC를 나타내어, 강력한 항균활성으로 실제적 사용 가능성을 나타내었다. 본 연구결과는 phenanthrene 링 구조의 -OH 및 $-OCH_3$ 수식이 항균활성 및 항균 스펙트럼 결정의 중요한 인자임을 제시하였다.

• Asian Pacific Journal of Cancer Prevention
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• 제16권6호
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• pp.2227-2230
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• 2015

Background: Prostate cancer (PCa) is one of the most commonly diagnosed neoplasms and the second leading cause of cancer death in men in the Western world. Vitamin D (1,25dihydroxy vitamin D) is linked to many biological processes that influence oncogenesis but data on relations between its genetic variants and cancer risk have been inconsistent. The aim of this study was to determine associations between a vitamin D genetic polymorphism and 25-hydroxyvitamin D [25(OH)D] levels and prostate cancer. Materials and Methods: Genomic DNA was extracted from 124 Jordanian prostate cancer patients and 100 healthy volunteers. Ethical approval was granted from the ethical committee at Hashemite University and written consent was given by all patients. PCR was used to amplify the vitamin D receptor Fok1 polymorphism fragment. 25(OH)D serum levels were measured by competitive immunoassay. Results: All genotypes were in Hardy-Weinberg equilibrium. Genotype frequency for Fok1 genotypes FF, Ff and ff was 30.7%, 61.3% and 8.06%, for prostate cancer patients, while frequencies for the control group was 28.0%, 66.0% and 6.0%, respectively, with no significant differences. Vitamin D serum level was significantly lower in prostate cancer patients (mean 7.7 ng/ml) compared to the control group (21.8 ng/ml). No significant association was noted between 25(OH)D and VDR Fok1 gene polymorphism among Jordanians overall, but significant associations were evident among prostate cancer patients (FF, Ff and ff : 25(OH)D levels of 6.2, 8.2 and 9.9) and controls (19.0, 22.5 and 26.3, respectively). An inverse association was noted between 25(OH)D serum level less than 10ng/ml and prostate cancer risk (OR 35.5 and 95% CI 14.3- 88.0). Conclusions: There is strong inverse association between 25(OH)D serum level less than 10ng/ml level and prostate cancer risk.

• Bulletin of the Korean Chemical Society
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• 제10권6호
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• pp.509-514
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• 1989

Reactions of thianthrene cation radical perchlorate (1) with N-(p-methoxyphenyl)benzenesulphonamide (14) in acetonitrile at room temperature afforded various products : thianthrene (3), N-(p-hydroxyphenyl)benzenesulphonamide (16), benzenesulphonamide (18), hydroquinone (20); 5-(5-benzenesulphonamido-2-methoxyphenyl)-thia nthrenium perchlorate(21), 2-benzenesulphonamido-2'-hydroxy-5,5'-dimethoxy biphenyl(24), 2-benzenesulphonamido-2',5'-dihydroxy-5-methoxy -biphenyl(25), and a traceable amount of p-quinone(23). The formations of part of (3) and (21) can be explained by either disproportionation or half-regeneration mechanism but those of the remainders by diverse reactions of sulphonamidyl radical (27) derived from (14) (through single electron transfer, followed by deprotonation processes). Similar results were observed from the reaction with N-(p-methoxyphenyl)methanesulphonamide (15).

• Food Science and Biotechnology
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• 제16권6호
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• pp.963-966
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• 2007

The objectives of this study were to identity antioxidant substance in heated garlic juice (HGJ). We evaluated the antioxidant activities of heated garlic juice exposed to 120, 130, and $140^{\circ}C$ for 2 hr. The HGJ was partitioned using the solvents of hexane, chloroform, ethyl acetate, butanol, and water. The ethyl acetate fraction of HGJ treated at $130^{\circ}C$ for 2 hr showed strong antioxidant activity; this extract was isolated and purified using silica gel column chromatography and semi-preparative high-performance liquid chromatography. The structure of the purified compound was determined using spectroscopic methods, i.e., ultraviolet, mass spectrometry, infrared, $^1H$ NMR, $^{13}C$ NMR, DEPT, HMBC, and HMQC. The isolated compound was identified as thiacremonone (2,4-dihydroxy-2,5-dimethyl-thiophene-3-one). Thiacremonone showed strong 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity, with a 50% inhibition concentration ($IC_{50}$) of $22.25{\pm}0.44\;{\mu}g/mL$, which is much higher than that of the antioxidants ascorbic acid ($30.06{\pm}0.42\;{\mu}g/mL$), ${\alpha}$-tocopherol ($71.30{\pm}0.97\;{\mu}g/mL$), and butylated hydroxyanisole ($50.54{\pm}0.94\;{\mu}g/mL$).

• 한국식품영양과학회지
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• 제31권2호
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• pp.177-183
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• 2002

대두 및 대두발효식품인 청국장과 된장의 cerebroside 구성성분인 지방산, 당 및 장쇄 sphingoid base들을 GC-MS로 분석하였다. Cerebroside 산-가수분해물의 지방산들을 O-TMS methylester 유도체로 만들어 분석하였으며 대두 및 청국장의 경우 2-hydroxyhexadecanoic acid(16 : 0h)가 각각 52.2% 및 62.0%로 가장 많았고 2-hydroxydocosanoic acid(22 : 0h) 및 2-hydroxytetracosanoic acid(24 : 0h)도 15.0~17.6%이었다. 그러나 된장의 경우 16 : 0h는 10.2%로 많은 감소를 보인 반면 24 : 0h는 40.9%, 22 : 0h는 23.4% 었으며 23 : 0h, 25 : 0h 및 26 : 0h도 대두 및 청국장에 비하여 많았다. Cerebroside 산-가수분해물의 장쇄 sphingoid base들은 N-acetyl-O-TMS 유도체로 분석하였으며 대두 및 청국장에서 4- trans, 8-trans-sphingadienine (d18 : 2 $\Delta$$^{4trans, 8trans}$) 는 59.9% 및 44.5%이었으며 4-hydroxy-8-trans, cis-sphingening (t18 : 1$\Delta$$^{8trans or cis}$)는 20.9% 및 35.9% 이었고 된장 cerebroside 역시 dl8 : 2$\Delta$$^{4trans, 8trans}$가 가장 많았다. 그러나 phytosphingosine(t18 : 0) 및 sphingosine 이 성질체(d18 : 1)들은 거의 보이지 않았다. 또한 된장의 경우 오랜 기간 미생물들에 의하여 발효되었지만 Aspergillus 속들의 cerebroside가 가지는 것으로 알려진 2-hydroxyoxtadec-3-enoic acid(18 : 1h) 및 9-methyl-4,8-sphingadienine 등은 발견되지 않았다. 대두, 청국장 및 된장 cerebroside의 당유도체 mass spectrum 분석 결과 99%이상이 glucose 1번 탄소가 ceramide backbone에 결합된 monoglucocerebroside 인 것으로 나타났다.

• The Korean Journal of Physiology and Pharmacology
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• 제16권5호
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• pp.313-320
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• 2012

In this study, we focused to identify whether eupatilin (5,7-dihydroxy-3',4',6-trimethoxyflavone), an extract from Artemisia argyi folium, prevents $H_2O_2$-induced injury of cultured feline esophageal epithelial cells. Cell viability was measured by the conventional MTT reduction assay. Western blot analysis was performed to investigate the expression of 5-lipoxygenase by $H_2O_2$ treatment in the absence and presence of inhibitors. When cells were exposed to 600 ${\mu}M$ $H_2O_2$ for 24 hours, cell viability was decreased to 40%. However, when cells were pretreated with 25~150 ${\mu}M$ eupatilin for 12 hours, viability was significantly restored in a concentration-dependent manner. $H_2O_2$-treated cells were shown to express 5-lipoxygenase, whereas the cells pretreated with eupatilin exhibited reduction in the expression of 5-lipoxygenase. The $H_2O_2$-induced increase of 5-lipoxygenase expression was prevented by SB202190, SP600125, or NAC. We further demonstrated that the level of leukotriene $B_4$ ($LTB_4$) was also reduced by eupatilin, SB202190, SP600125, NAC, or nordihydroguaiaretic acid (a lipoxygenase inhibitor) pretreatment. $H_2O_2$ induced the activation of p38MAPK and JNK, this activation was inhibited by eupatilin. These results indicate that eupatilin may reduce $H_2O_2$-induced cytotoxicity, and 5-lipoxygenase expression and $LTB_4$ production by controlling the p38 MAPK and JNK signaling pathways through antioxidative action in feline esophageal epithelial cells.

• Natural Product Sciences
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• 제21권2호
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• pp.111-121
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• 2015

The root of Panax ginseng, is a Korea traditional medicine, which is used in both raw and processed forms due to their different pharmacological activities. As part of a continued chemical investigation of ginseng, the focus of this research is on the isolation and identification of compounds from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, semi-preparative-high performance liquid chromatography, Fast atom bombardment mass spectrometric, and nuclear magnetic resonance. Dammarane-type triterpenoid saponins were isolated from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, and semi-preparative-high performance liquid chromatography. Their structures were identified as protopanaxadiol ginsenosides [gypenoside-V (1), ginsenosides-Rb1 (2), -Rb2 (3), -Rb3 (4), -Rc (5), and -Rd (6)], protopanaxatriol ginsenosides [20(S)-notoginsenoside-R2 (7), notoginsenoside-Rt (8), 20(S)-O-glucoginsenoside-Rf (9), 6-O-[$\alpha$-L-rhamnopyranosyl(1$\rightarrow$2-$\beta$-D-glucopyranosyl]-20-O-$\beta$-D-glucopyranosyl-$3\beta$,$12\beta$, 20(S)-dihydroxy-dammar-25-en-24-one (10), majoroside-F6 (11), pseudoginsenoside-Rt3 (12), ginsenosides-Re (13), -Re5 (14), -Rf (15), -Rg1 (16), -Rg2 (17), and -Rh1 (18), and vinaginsenoside-R15 (19)], and oleanene ginsenosides [calenduloside-B (20) and ginsenoside-Ro (21)] through the interpretation of spectroscopic analysis. The configuration of the sugar linkages in each saponin was established on the basic of chemical and spectroscopic data. Among them, compounds 1, 8, 10, 11, 12, 19, and 20 were isolated for the first time from P. ginseng root.

• 대한한의학방제학회지
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• 제16권1호
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• pp.117-130
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• 2008

Korean traditional medicine has been used for the treatment of the various diseases based on both oriental medicinal theory and clinical trials. Thus, the prescriptions of Korean traditional medicine would be useful for the development of new therapeutics. This research focuses on the fundamental study in Korean traditional prescriptions for the development of new hepatoprotective agents. We found two prescriptions. Injinho-Tang and Osumogwa-Tang, showed the significant DPPH free radical scavenging and hepatoprotective effect, respectively. It is well-known that free radical scavenging effect is related to the prevention of various pathological events including liver injury. This paper deals with hepatoprotective effects on tacrine-induced cytotoxicity in Hep G2 cells, free radicals scavenging on both DPPH and superoxide of above two prescriptions. Hot water extract of Injinho-Tang did not show the significant hepatoprotective effect on tacrine-induced cytotoxicity in Hep G2 cells, however, it shows the significant scavenging effects for both DPPH and superoxide radicals. On the other hand, all of the hot water extracts of constituent herbal drugs in Injinho-Tang exhibited the promising protective effect on tacrine-induced cytotoxicity in Hep G2 cells. Of these, water extract of Rhei Rhizoma showed the most prominent effect on tacrine-induced cytotoxicity in Hep G2 cells. Bioassay-guided fractionation of Rhei Rhizoma extract has furnished four compounds, and their chemical structures have been identified by comparison of their spectral data with those of literature as chrysophanol (1), emodin (2), 3,5-dihydroxy-4'- methoxystilbene (3), and rhapontigenin (4), respectively. Among the isolated compounds, compounds 2-4 revealed the significant hepatoprotective effect in vitro when their $EC_{50}$ values compare with that of silybin, as a positive control. It also exhibited that emodin possessed the most hepatoprotective effect among these active compounds. In case of Osumogwa-Tang, its hot water extract showed the moderate protective effect on tacrine-induced cytotoxicity in Hep G2 cells. Hot water extract of Chaenomelis Fructus, one of the constituent herbal drug of this prescription, exhibited the significant hepatoprotective effect with $EC_{50}$ value of $7.8{\pm}0.1\;{\mu}g/ml$, however, it showed strong cytotoxicity in Hep G2 cells above the concentration of $25\;{\mu}g/ml$. It was revealed that both hot water extract of Evodiae Fructus and its butanol soluble fraction showed the moderate hepatoprotective effect but concentration-dependent activity in Hep G2 assay system. Two quinolone alkaloids, evocarpine and dihydroevocarpine, also tested for their hepatoprotective effects on tacrine-induced cytotoxicity in Hep G2 cells, however, these two compounds derived from the Evodiae Fructus as the major constituents did not show in vitro hepatoprotective effect. From these results, it would be necessary to further isolation of its hepatoprotective compounds from the butanol soluble fraction of the hot water extract of Evodiae Fructus.