• 대한화학회지
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• 제33권5호
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• pp.551-557
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• 1989

아닐린과 부틸, 헥실, 옥틸기를 가진 n-알킬 알코올류로부터 6-alkylbenzofuroxan류를 합성하고, 이들과 1,3,5-trihydroxybenzene을 반응시켜 7-alkyl-1,3-dihydroxyphenazine-5,10-dioxide류를 합성하였다. 그리고 benzofuroxan과 1,3,5-trihydroxybenzene을 반응시켜 1,3-dihydroxyphenazine-5,10-dioxide도 합성하였다. 이들 phenazine dioxide 유도체의 수용액에 대한 표면장력을 측정하였는데 알킬기의 탄소수가 증가할수록 표면장력이 저하됨을 알았다. 또한 항균성을 희석법에 의하여 조사하였는데 알킬기의 탄소수가 4개인 부틸유도체의 경우가 가장 항균성이 강했으며, 알킬기가 없는 phenazine dioxide 유도체보다는 알킬기가 치환된 phenazine dioxide 유도체의 항균성이 더 강하다는 것을 알았다.

• 약학회지
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• 제36권5호
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• pp.440-448
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• 1992

7-Substituted 2,3-dihydroxyphenazine 5,10-dioxides were synthesized by the reaction of 1,2,4-trihydroxybenzene with 6-substituted benzofuroxan derivatives which had been obtained from aniline derivativies bearing methoxy, methyl, acetyl and nitro group at the para position. 2,3-Dihydroxyphenazine 5,10-dioxide was also prepared by the reaction of 1,2,4-trihydroxybenzene with benzofuroxan. The antimicrobial activities of these phenazine dioxide were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. It was observed that the antimicrobial activity of the phenazine dioxides bearing electron releasing substituents was stronger than that of those bearing electron withdrawing substitutents. From this result, it was concluded that the antimicrobial activity of phenazine dioxide derivatives has a direct relationship with the electronic effect of the substituents.

• Biomolecules & Therapeutics
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• 제32권4호
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• pp.499-507
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• 2024

Specific sensitivity of the skin to ultraviolet B (UVB) rays is one of the mechanisms responsible for widespread skin damage. This study tested whether 1,3,5-trihydroxybenzene (THB), a compound abundant in marine products, might inhibit UVB radiationinduced NADPH oxidase 4 (NOX4) in both human HaCaT keratinocytes and mouse dorsal skin and explore its cytoprotective mechanism. The mechanism of action was determined using western blotting, immunocytochemistry, NADP⁺/NADPH assay, reactive oxygen species (ROS) detection, and cell viability assay. THB attenuated UVB-induced NOX4 expression both in vitro and in vivo, and suppressed UVB-induced ROS generation via NADP⁺ production, resulting in increased cell viability with decreased apoptosis. THB also reduced the expression of UVB-induced phosphorylated AMP-activated protein kinase (AMPK) and phosphorylated c-Jun N-terminal kinase (JNK). THB suppressed UVB-induced NOX4 expression and ROS generation by inhibiting AMPK and JNK signaling pathways, thereby inhibiting cellular damage. These results showed that THB could be developed as a UV protectant.

• Applied Biological Chemistry
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• 제45권3호
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• pp.168-172
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• 2002

한국산 옻나무의 메탄올추출물과 유기용매 분획의 항산화 효과를 조사하였다. 항산화 효과는 수소공여 억제능, 과산화지질 형성 억제능, xanthine oxidase저해 활성과 아질산염 소거능으로 측정한 결과, ethyl acetate 분획이 가장 뛰어난 효과를 나타내었다. 이 분획의 생리활성 물질을 분리하기 위하여, rotatory locular counter current chromatography(RLCCC), Sephadex LH-20 column chromatograpy와 HPLC등의 방법을 사용하여, 1,2,3-trihydroxybenzene, methyl 3,4,5-trihydroxybenzoat와 3,4,5-trihydroxybenzoic acid를 분리하였다. 이중 methyl 3,4,5-trihydroxybenzoate는 butylated hydroxyanisole(BHA)이나 butylated hydroxytoluene(BHT)보다도 강한 항산화 효과를 나타내었다. 그러나 세포독성 실험에서는 이들 물질들이 암세포주에 대하여 활성이 높지 않았다. 이상의 결과로 methyl 3,4,5-trihydroxybenzoate은 뛰어난 항산화 효과를 지닌 식품첨가물로서의 이용 가능성을 제시할 수 있다.

• Biomolecules & Therapeutics
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• 제29권1호
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• pp.90-97
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• 2021

Ultraviolet B (UVB) radiation causes DNA base modifications. One of these changes leads to the generation of 8-oxoguanine (8-oxoG) due to oxidative stress. In human skin, this modification may induce sunburn, inflammation, and aging and may ultimately result in cancer. We investigated whether phloroglucinol (1,3,5-trihydroxybenzene), by enhancing the expression and activity of 8-oxoG DNA glycosylase 1 (Ogg1), had an effect on the capacity of UVB-exposed human HaCaT keratinocytes to repair oxidative DNA damage. Here, the effects of phloroglucinol were investigated using a luciferase activity assay, reverse transcription-polymerase chain reactions, western blot analysis, and a chromatin immunoprecipitation assay. Phloroglucinol restored Ogg1 activity and decreased the formation of 8-oxoG in UVB-exposed cells. Moreover, phloroglucinol increased Ogg1 transcription and protein expression, counteracting the UVB-induced reduction in Ogg1 levels. Phloroglucinol also enhanced the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2) as well as Nrf2 binding to an antioxidant response element located in the Ogg1 gene promoter. UVB exposure inhibited the phosphorylation of protein kinase B (PKB or Akt) and extracellular signal-regulated kinase (Erk), two major enzymes involved in cell protection against oxidative stress, regulating the activity of Nrf2. Akt and Erk phosphorylation was restored by phloroglucinol in the UVB-exposed keratinocytes. These results indicated that phloroglucinol attenuated UVB-induced 8-oxoG formation in keratinocytes via an Akt/Erk-dependent, Nrf2/Ogg1-mediated signaling pathway.