• Preventive Nutrition and Food Science
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• 제20권1호
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• pp.73-77
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• 2015

As an approach to search for chemopreventive agents, we tested p-coumaric acid, 3-methoxy-p-coumaric acid (ferulic acid), and 3,5-dimethoxy-p-coumaric acid (sinapic acid) in B16/F10 melanoma cells. Intracellular melanin contents were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay and cytotoxicity of the compounds were examined by lactate dehydrogenase (LDH) release. p-Coumaric acid showed inhibitory effect on melanogenesis, but ferulic acid increased melanin content, and sinapic acid had almost no effect on melanogenesis. Treatment with ferulic acid resulted in a 2 to 3 fold elevation in the production of melanin. Correlatively, cell viability decreased in a dose-dependent manner when treated with ferulic acid. However, ferulic acid did not affect the LDH release from the cells. Treatment with sinapic acid resulted in a 50~60% elevation in the release of LDH when treated with a $200{\mu}g/mL$ concentration and showed neither cytostasis nor increase of melanin synthesis in a dose-dependent manner. Taken together, p-coumaric acid inhibits melanogenesis, ferulic acid induces melanogenesis, and sinapic acid exerts cytotoxic effects in B16/F10 murine melanoma cells. The results indicate that the addition of methoxy groups to p-coumaric acid shows the melanogenic or cytotoxic effects in melanoma cells compared to the original compound. Therefore, this study suggests the possibility that methoxylated p-coumaric acid, ferulic acid can be used as a chemopreventive agent.

• Journal of Applied Biological Chemistry
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• 제44권3호
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• pp.143-146
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• 2001

Eight flavonoids, including rutin, naringin, hesperidin, quercetin, hesperetin, nobiletin, 3,5,6,7,8,3',4'-methoxylated flavone, and tangeretin, in the peels of satsuma mandarin (Citrus unshiu) species of Halla, Gungcheon, Hungjin, Namgam-20, Illnam-1, and Chungdo harvested between August and December were analyzed through HPLC. Hesperidin content of Halla harvested during early maturation was 28.70 mg/g, and was the highest among the tested citrus fruits. Rutin content of Hungjin harvested during early maturation was 2.66 mg/g. Naringin in all citrus species and hesperetin in Halla, Gungchun, Namgam-20, and Chungdo were only detected in the peel of fruits harvested during early maturation. Hesperidin and rutin were detected mainly in all citrus species, and other flavonoids in trace. Flavonoid content in the peel of fruits was high during early maturation. Flavonoid contents in the peels of all fruit samples were generally high in the early stage of maturation, which then decreased rapidly.

• BMB Reports
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• 제44권7호
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• pp.423-434
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• 2011

A female hormone, estrogen, is linked to breast cancer incidence. Estrogens undergo phase I and II metabolism by which they are biotransformed into genotoxic catechol estrogen metabolites and conjugate metabolites are produced for excretion or accumulation. The molecular mechanisms underlying estrogen-mediated mammary carcinogenesis remain unclear. Cell proliferation through activation of estrogen receptor (ER) by its agonist ligands and is clearly considered as one of carcinogenic mechanisms. Recent studies have proposed that reactive oxygen species generated from estrogen or estrogen metabolites are attributed to genotoxic effects and signal transduction through influencing redox sensitive transcription factors resulting in cell transformation, cell cycle, migration, and invasion of the breast cancer. Conjuguation metabolic pathway is thought to protect cells from genotoxic and cytotoxic effects by catechol estrogen metabolites. However, methoxylated catechol estrogens have been shown to induce ER-mediated signaling pathways, implying that conjugation is not a simply detoxification pathway. Dual action of catechol estrogen metabolites in mammary carcinogenesis as the ER-signaling molecules and chemical carcinogen will be discussed in this review.

• Journal of the Korean Wood Science and Technology
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• 제28권4호
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• pp.25-28
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• 2000

Two flavan 3,4-diol derivatives were isolated from the heartwood of Robinia pseudoacacia and characterized by spectroscopic methods including $^1H$ and $^{13}C$ NMR and positive FAB-MS. The structures were identified as 2,3-trans-3,4-cis-3,4,7,3',4',5'-hexahydroxy flavan, one of isomeric leucorobinetinidins, and 4'-methoxy-2,3-trans-3,4-cis-3,4,7,3',5'-pentahydroxy flavan.

• Applied Biological Chemistry
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• 제50권3호
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• pp.154-159
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• 2007

제주산 병귤을 침출주의 소재로 활용하기 위하여 $30{\sim}95%$ 주정농도에 건조과피를 각각 500 g/10 l(5%, w/v) 비율로 첨가하여 70일간 침출특성을 검토하였다. 주정농도 30%에서 pH는 $5.19{\sim}4.80$으로 가장 낮았으며, 침출 후 10일까지 주정농도가 낮을수록 감소하는 경향이었다. 주정농도가 높을수록 색도 a값이 낮아지고, b값이 증가하였다. 가용성고형물은 주정농도 $30{\sim}70%$에서 $2.00{\sim}2.19%(w/v)$로, 지속적으로 증가하는 경향이었다. 산함량은 주정농도 $30{\sim}70%$에서 $0.18{\sim}0.21%(v/v)$로 차이가 거의 없었으며, 주정농도 95%에서는 $0.13{\sim}0.15%(v/v)$였다. 주정농도 낮을수록 fructose와 glucose가 많았으며, 침출기간이 길어질수록 sucrose 함량은 낮았다. 병귤과피의 주요 flavonoid는 narirutin, hesperidin, nobiletin, 3,5,6,7,8,3'4'-methoxylated flavone, tangeretin이었고, 대부분의 flavonoids는 침출 후 $3{\sim}5$일에 80%이상 용출되었다. 총 폴리페놀 함량은 주정농도 $30{\sim}70%$로 20일 침출에서 $628.8{\sim}711.2$ ${\mu}g/ml$였으며, 주정원액에서 가장 높은 함량을 나타내었다. 따라서 병귤과피를 침출주 원료로 사용하였을 때, 주정농도 $50{\sim}70%$에서 20일 동안 침출시키는 방법이 효과적이었다.

• 한국식품과학회지
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• 제31권3호
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• pp.815-822
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• 1999

우리 나라 전역에 자생하는 쑥(Artemisia vulgaris)의 전초의 수용성 에탄올추출물로 부터 21가지의 flavonoids를 분리하였다. 이들 화합물의 동정은 H-NMR, mass, UV-스펙트럼을 이용하여 동정하였으며, 동정된 flavonoids들은 tricin, jaceosidine, eupafolin, diosmetin, chrysoeriol, humoeridictyol, isorhamnetin, apigenin, eriodictyol, luteolin, luteolin 7-glucoside, kaempferol 3-glucoside, kaempferol 7-glucoside, kaempferol 3-rhamnoside, kaempferol 3-rutinoside, quercetin, quercetin 3-glucoside, quercetin 3-galactoside, quercetin, quercetin 7-glucoside, rutin 그리고 vitexin으로 동정 되었다. 이들 분리된 각 flavonoids들에 대하여 쥐의 간에서 추출한 마이크로좀에 대하여 지질과산화 효과를 살펴보았다. 이들 flavonoids화합물들의 항산화효과는 비타민 E와 비교하였을 때 높은 활성이 나타났다. 이미 강력한 항산화물질로 잘 알려진 quercetin, apigenin, eriodictyol등의 화합물의 $IC_{50}$ 값은 각각 0.9, 0.3, $0.3\;{\mu}g/mL$로 나타났으며, methoxylated flavonoids인 eupafolin, jaceosidine, diosmetin 등의 화합물도 $IC_{50}$ 값이 1.0, 1.4, $1.0\;{\mu}g/mL$로 나타나 비타민 E에 비교할 때 높은 활성을 나타냈다.

• Journal of Microbiology and Biotechnology
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• 제13권1호
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• pp.43-49
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• 2003

Metabolism of a new fungicide ethaboxam by soil fungi was studied. Among the fungi tested, Cunninghamelia elegans produced metabolites from ethaboxam, which were not found in the control experiments. M5, a major metabolite from ethaboxam was firmly identified as N-deethylated ethaboxam by LC/MS/MS and NMR. N-Deethylated ethaboxam has been found as a single metabolite in in vitro metabolism with rat liver microsomes. Ml was proved to be 4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide (ETC) by comparing with the authentic compound. In addition, M2, M3, and M4, and M6 were tentatively Identified by LC/MS/MS as hydroxylated and methoxylated ethaboxams, respectively. Production of the major metabolite, N-deethylated ethaboxam, by the fungus suggested that C. elegans would be an efficient eukaryotic microbial candidate for evaluating xenobiotic-driven mammalian risk assessment.

• Food Science and Biotechnology
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• 제15권2호
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• pp.163-167
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• 2006

Pectin was enzymatically extracted from industrial lemon pomace by using an endo-polygalacturonase from Aspergillus niger as a processing aid and compared to pectin extraction by hot hydrochloric acid. The yield of pectin was 17.6 and 20.2% with enzymatic and acidic treatments, respectively. The molecular weight distribution did not vary greatly between the samples extracted with enzyme or acid. Large differences in charge density were observed, however, when the samples were analyzed by anionic-exchange chromatography. Pectin extracted by the enzymatic treatment indicated higher charge density than that obtained by hydrochloric acid. The higher charge density could due to the presence of endogenous lemon pectinesterase, which was activated at low pH 4.5 in situ conditions during the process of enzymatic extraction, leading to low methoxylated pectin with a higher charge density.

• 대한화학회지
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• 제46권3호
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• pp.205-212
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• 2002

청피의 생리활성 물질인 methoxy flavonoids를 컬럼크로마토그래피와 preparative-HPLC 방법으로분리하였으며 흰쥐의 기관지 평활근에 미치는 이완효과를 조사하였다. Acetylcholine($ED_{50}:3{\times}10^{-6}M$)으로 흰쥐의 기관지 평활근을 수축시킨 후, 크로마토그래피의 분획별로 처리하였다. 수축된 기관지 평활근을 에칠아세테이트의 2차분리 분획무로 처리한 결과 methoxy기가 6개인 flavonoid(nobiletin)의 분획물이 가장 좋은 결과를 나타내었다. 이로써 nobiletin과 그의 유사물질이 기관지 천식이나 해소의 유망한 치료제로 작용할 수 있음을 알았다.

• Preventive Nutrition and Food Science
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• 제15권1호
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• pp.57-66
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• 2010

Passion fruit fiber pectin gels represent a new alternative pectin source with potential for food and non-food applications on a commercial scale. Pectic polysaccharides were extracted from passion fruit (Passiflora edulis) fiber using citric acid as a clean catalyst and autoclaved for 20 to 60 min at $121^{\circ}C$. The best condition of pectin yield with the highest molecular weight was obtained with 1.0% of citric acid (250 mg/g dry passion fruit fiber pectin) for 20 min of autoclaving. Spectroscopic analyses by Fourier transform infrared, enzymatic degradation reactions, and ion-exchange chromatography assays showed that passion fruit pectin extracted for 20 min was homogeneous high methoxylated pectin (70%). Gel permeation analysis confirmed that the pectin extract obtained by autoclaving by 20 min showed higher molecular weights than those autoclaved for 40 and 60 min. Passion fruit pectin extracted for 20 min was enzymatically modified with fungal pectinmethylesterase to create restructured gels. Short autoclave treatment (20 min) with citric acid as extractant resulted in a significant increase of gel strength, improving pectin extraction in terms of functionality. The treatment of solubilized material (pectic polysaccharides) in the presence of insoluble material (cellulose and hemicellulose) with pectinmethylesterase and calcium led to the creation of a stiffer passion fruit fiber pectin gel, while syneresis was not observed.