• 제목/요약/키워드: apigenin derivatives

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Chemical Constituents of the Root of Dystaenia takeshimana and Their Anti-Inflammatory Activity

  • Kim, Ju-Sun;Kim, Jin-Cheul;Shim, Sang-Hee;Lee, Eun-Ju;Jin, Wen-Yi;Bae, Ki-Hwan;Son, Kun-Ho;Kim, Hyun-Pyo;Kang, Sam-Sik;Chang, Hyeun-Wook
    • Archives of Pharmacal Research
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    • 제29권8호
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    • pp.617-623
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    • 2006
  • In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5- lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin $D_2\;(PGD_2)$ and leukotriene $C_4\;(LTC_4)$ in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with ${\beta}-sitosterol$ (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)- marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.

한국산 닭의덩굴속 호장근절(마디풀과)의 화학분류학적 연구 (Flavonoid chemistry of Fallopia sect. Reynoutria (Polygonaceae) in Korea)

  • 박진희;문혜경;박종욱
    • 식물분류학회지
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    • 제41권1호
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    • pp.10-15
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    • 2011
  • 본 연구에서는 한국산 닭의덩굴속 호장근절 분류군들을 대상으로 개체군 수준에서 flavonoid 분석을 수행하여, 본 절 분류군에서 나타나는 형태변이 양상을 화학적 측면에서 파악하고, 이를 토대로 한반도에 분포하는 본 절 분류군들의 실체 및 한계를 정확히 파악하고자 하였다. 그 결과, 한국산 본 절 3분류군 15개체군의 잎으로부터 19종류의 서로 다른 flavonoid compound가 분리, 동정되었으며, 이들은 flavonol인 quercetin 및 kaempferol 3-O-glycoside들과 flavone인 apigenin및 luteolin C-glycoside들이었다. 이들 compound들 중 한국산 본 절 식물에 분포하는 주요 flavonoid compound는 quercetin 3-O-galactoside 와 quercetin 3-O-glucoside이었다. 본 절 한국산 분류군들은 그 flavonoid 조성에 의해 뚜렷이 구분되는 것으로 밝혀졌으며, 이러한 결과는 기존의 외부 형태학적 연구 결과와 전반적으로 일치하였다. 한편, 잡종으로 추정되는 논산 개체군의 flavonoid 조성은 F. japonica var. japonica, F. forbesii 및 F. sachalinensis와 일부 compound를 공유하는 것으로 나타났다. Fallopia japonica var. japonica의 경우, 염색체수 배수화에 따른 flavonoid 조성의 정성적 차이는 발견할 수 없었으나, 지리적 변이가 일부 나타나는 것으로 밝혀졌다.

구절초 chrysanthemum sibiricum FISCHER의 성분 연구 (Studies on the consituents of Chrysanthemum sibiricum FISHER)

  • 이용주
    • 약학회지
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    • 제11권1_2호
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    • pp.7-16
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    • 1967
  • A yellowish microneedles, $C_{28}$ H$_{32}$ $O_{14}$ ${\cdot}$ I$_{1}$/$_2$, H$_{2}$O, m.p.262-$4^{\circ}$ , [${\alpha}$$_{D}^{20}$= -71,$43^{\circ}$(C = 0.42, pyridine), its acetate m.p.123-5.deg., were obtained in 0.3% yield from the leaves of Chrysanthemum sibiricum F$_{ISCHER}$. This substance is insoluble in water and the usual organic solvents except pyridine and ethylene glycol and, is not decomposed by dilute mineral acids but undergoes decomposition on being boiled in 60% H$_{2}$SO$_{4}$ or 35% HCl, giving one moel each of acacetin, glucose and rhamnose. It was not hydrolysed with a rhamnodiastase preparation obtained from the seeds of Rhamnus koraiensis. After permethylation of it, the uncrystallized product was hydrolysed and apigenin-5,4'-dimethyl ehter, m.p.$262^{\circ}$ was obtained, indicating that the disaccharide residue is at the 7 position of acacetin. Partial hydrolysis of this acacetin-7-rhamnoglucoside in cyclohexanol with formic acid gave acacetin-7-glucoside, m.p.246.deg. and rutinose, identifying them with authentic specimen on a paper chromatography. It was thus identified as linarin(acacetin-7-rutinoside) by means of mixed fusion, of paper partition chromatography and of its derivatives. Zemplen and Bognar suggested that the glucosidic linkage of linarin is .betha. by means of synthesis of this substance. But there is no evidence whether it is hydrolysed by emulsin or maltase or not. Linarin itself was not hydrolysed by an emulsin existing in the seed of Apricot or a maltase, but acacetin-7-glucoside(tilianin) which obtained from linarin gave acacetin and glucose on hydrolysis with the same emulsin and accordingly the glucosidic linkages of linarin and tilianin are thus regarded as ${\beta}$.

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Antioxidative and anti-inflammatory activities of Phaseolus aureus

  • Hong, In-Taik;Kim, Beom-Jun;Yu, Duck-Cho;Kim, Jung-Haeng;Kim, Jung-Han;Heo, Moon-Young;Lee, Song-Jin;Kim, Hyun-Pyo
    • 대한화장품학회지
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    • 제22권2호
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    • pp.41-51
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    • 1996
  • Phaseolus aureus (mung bean), Leguminosae, has been used as an antidote from the ancient time. Especially, it has been widely used for cleaning face and skin in oriental countries. Although several constituents such as fatty acids, phytoallexin and phaseol derivatives were reported in P. aureus and related species including seedlings, there has been a few report to describe its biological activity. Therefore, in this investigation, the ethanol extract from P. aureus was obtained and its biological activities including the antioxidative and anti-inflammatory activities were studied. The 70% ethanol extract from P. aureus showed dose-dependent antioxidative activity (52.3% inhibition at 4 mg/ml) against lipid peroxidation assay, while the extract did not show the inhibitory activity of superoxide radical formation. The extract also showed the topical anti-inflammatory activity against croton-oil and arachidonic acid induced mouse ear edema test (18-19% inhibition at 7.5 mg/ear) as well as mild inhibitory activity against picryl chloride induced delayed hypersensitivity in mouse. For investigating active principles, vitexin and isovitexin (apigenin C-glycoside) as flavonoids, and adenosine were isolated from the extract using silica gel chromatography. The actual contents of vitexin and isovitexin were found to be 3.7 and 2.4 mg/g extract, respectively. Vitexin and isovitexin showed the antioxidative activity. They showed the topical anti-inflammatory activity, although the activities were not potent compared to the reference compounds. These results suggested that vitexin and isovitexin may be, at least in part, the compounds contributing the antioxidative activity in vitro and the topical anti-inflammatory activity of P. aureus in vivo. All results of present study might be one of the scientific rationale in using mung bean for skin care from the ancient time.

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