• 동의생리병리학회지
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• 제33권6호
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• pp.349-355
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• 2019

The anti-inflammatory effects of 4'-O-methylalpinumisoflavone (OMAI) has been reported in recent years. To develop effective and safe skin whitening agents, we investigated the anti-oxidative and melanogenic effects of OMAI isolated from fruit of Maclura tricuspidata Carrière (Cudrania tricuspidata) in macrophage and melanoma cell lines. In our results, OMAI showed effective superoxide scavenging activity and suppressed production of lipopolysaccharide (LPS)-induced intracellular reactive oxygen species (ROS) in RAW264.7 cells. In addition, α-melanocyte stimulation hormone (MSH)-induced production of melanin was also reduced by OMAI in B16F10 cells. Finally, OMAI significantly inhibited tyrosinase activity in B16F10 cells. These results suggest that OMAI suppressed melanin production via scavenging reactive oxygen species and inhibition of tyrosinase activity.

• International Journal of Molecular Medicine
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• 제43권5호
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• pp.2177-2186
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• 2019

The epidemiological, animal and cell effects of plant metabolites suggest versatile health benefits of flavonoids. However, whether flavonoids affect the deleterious biological activity of oxygenated cholesterol molecules remains to be elucidated. The present study investigated the effects of 4'-O-methylalpinumisoflavone (mAI) isolated from Maclura tricuspidata (Cudrania tricuspidata) on the 27-hydroxycholesterol (27OHChol)-induced activation of monocytes/macrophages using human THP-1 cells. mAI dose-dependently impaired the expression of C-C motif chemokine ligand (CCL)2 chemokine and the migration of monocytic cells enhanced by 27OHChol. mAI downregulated the surface and cellular levels of CD14 and inhibited the release of soluble CD14. This isoflavone significantly weakened the lipopolysaccharide responses that were enhanced in the presence of 27OHChol, and inhibited the transcription and secretion of the active gene product of matrix metalloproteinase-9. mAI also suppressed the expression of C-C motif chemokine receptor 5 ligands, including CL3 and CCL4, and M1-phenotype markers induced by 27OHChol. Furthermore, mAI impaired phosphorylation of the nuclear factor-κB p65 subunit without affecting the phosphorylation of Akt. These results indicate that mAI inhibits the activation of monocytes/macrophages to the immunostimulatory phenotype in a milieu rich in 27OHChol, suggesting potential benefits of the flavonoid for the treatment of diseases in which the pathogenesis is linked to 27OHChol-induced inflammatory responses.

• Journal of the Korean Wood Science and Technology
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• 제44권3호
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• pp.337-349
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• 2016

본 연구는 꾸지뽕나무 열매에서 분리 및 정제한 isoflavonoid 성분에 대하여 Ultra Performance Liquid Chromatography(UPLC)을 이용하여 분석법을 개발하고 검증하고자 하였다. 꾸지뽕나무 열매를 methanol로 추출하여 n-hexane, ethyl acetate, 물 순으로 분액 후, ethyl acetate 추출물을 silica gel 컬럼과 sephadex LH-20 컬럼을 사용하여 4종의 isoflavonoid들을 분리하였다. 분리한 4종의 isoflavonoid들은 기기분석(UV-Vis spectroscopy, ESI-MS, $^1H\;NMR$, $^{13}C\;NMR$)을 통하여 alpinumisoflavone, 6,8-diprenyl orobol, 6,8-diprenyl genistein, 4'-O-methylalpinumisoflavone으로 확인 및 동정하였다. 이 성분들을 2% acetic acid 용액(용매 A)과 2% acetic acid가 함유된 MeOH 용액(용매 B)을 기울기 이동상으로 하여 $C_{18}$ 컬럼이 장착된 UPLC로 분석하였다. 분석 조건은 ICH (International Conference on Harmonisation) 가이드라인에 기술된 선택성, 직선성, 정량한계, 검출한계, 정확성 및 정밀성을 측정하여 분석법의 타당성을 검증하였다. 또한 검증한 분석방법을 이용하여 꾸지뽕나무 열매의 채취시기별 함량을 조사하였다. 그 결과, 미숙과는 7월과 8월에 각 성분의 함량이 증가하였다가 9월에는 감소하였고, 성숙과의 경우 9월 미숙과 보다 각 성분들이 전반적으로 많이 함유되어 있었다.

• Journal of Applied Biological Chemistry
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• 제48권4호
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• pp.193-197
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• 2005

Isoflavones 4'-O-methylalpinumisoflavone (1) and 5, 7, 4'-trihydroxy-6,8-diprenylisoflavone (2) were isolated from stem bark of Cudrania tricuspidata (Carr.) Bureau. These compounds were the first reported from this plant. Antioxidant activities 1 and 2 were evaluated by measuring their ability to scavenge DPPH and ABTS radicals. Diprenylisoflavone 2 showed strong scavenging activity against ABTS ($IC_{50}\;=\;16.3\;{\mu}M$), three-fold higher compared to genistein, which do not possess prenylated group which indicates strong scavenging activity against ABTS radical of isoflavone 2 was due to prenyl group.

• Archives of Pharmacal Research
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• 제28권12호
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• pp.1324-1327
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• 2005

A methylene chloride soluble fraction of the fruits of Cudrania tricuspidata significantly inhibited the mouse brain monoamine oxidase (MAO). Three known prenylated isoflavones were isolated and identified by activity-guided fractionation. Gancaonin A (1), 4'-O-methylalpinumisoflavone (2), and alpinumisoflavone (3) inhibited MAO activity in a concentration-dependent manner with $IC_{50}$ values of 19.4, 23.9, and 25.8 $\mu$M, respectively. Of these, gancaonin A (1) showed a selective and potent inhibitory effect against MAO-B ($IC_{50}$ 0.8 $\mu$M) than MAO-A ($IC_{50}$ >800 $\mu$M). The kinetic analysis using Lineweaver-Burk plots indicated that gancaonin A (1) competitively inhibited MAO-B.