• 제목/요약/키워드: Prenylated flavonoid

검색결과 15건 처리시간 0.018초

Xanthone and Flavonoid Derivatives from the Leaves of Maclura tricuspidata with Antioxidant and Anti-tyrosinase Activity

  • Jo, Yang Hee;Lee, Solip;Ryu, Se Hwan;Yeon, Sang Won;Turk, Ayman;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Natural Product Sciences
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    • 제27권4호
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    • pp.234-239
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    • 2021
  • Masclura tricuspidata, also called as Cudrania tricuspidata, is one of the most common Moraceae family plants in East Asia. Its trivial name follows mulberry due to the similar morphology. Investigation of the bioactive constituents of M. tricuspidata leaves yielded a new xanthone derivative along with twenty known compounds through various chromatographic techniques. A new compound was defined as mascluraxanthone (3), a prenylated xanthone glucoside on the basis of 1D and 2D NMR and MS data. Twenty known compounds were identified as four xanthone derivatives (1-2 and 4-5), two flavans (6-7), six flavanol derivatives (8-13), a flavonone (14) and seven flavonol derivatives (15-21). Among the isolated compounds, flavanol and flavonoid derivatives with 3',4'-OH groups showed antioxidant and anti-tyrosinase activities. Conclusively, the leaves of M. tricuspidata are rich in aromatic compounds including xanthones and flavonoids. In addition, these constituents showed antioxidant and anti-tyrosinase potentials, which might be useful for oxidative stress related diseases.

Anti-Inflammatory Activity of the Total Flavonoid Fraction from Broussonetia papyrifera in Combination with Lonicera japonica

  • Jin, Jeong-Ho;Lim, Hyun;Kwon, Soon-Youl;Son, Kun-Ho;Kim, Hyun-Pyo
    • Biomolecules & Therapeutics
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    • 제18권2호
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    • pp.197-204
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    • 2010
  • To establish the anti-inflammatory activity of the total flavonoid fraction of the root barks of Broussonetia papyrifera (EBP) and a new formula, the ethanol extract of the root barks of B. papyrifera was fractionated with ethylacetate, yielding the hydrophobic prenylated flavonoid-enriched fraction. EBP and the ethanol extract of the whole Lonicera japonica (ELJ) plant were then mixed at a ratio of 1:1 (w/w) to give a new preparation (BL) in the hope of obtaining an optimal formula with a higher anti-inflammatory activity. Evaluation of the effects of these preparations on A23187-treated rat basophilic leukemia (RBL-1) cells revealed that EBP potently inhibited 5-lipoxygenase (5-LOX), while ELJ showed weak inhibition. Additionally, the mixture (BL) clearly showed stronger inhibitory effects against 5-LOX than either preparation alone. These preparations also inhibited cyclooxygenase-2-catalyzed $PGE_2$ and inducible nitric oxide (NO) synthase-catalyzed NO production by lipopolysaccharide-treated RAW 264.7 cells. When tested against arachidonic acid-induced mouse ear edema, EBP showed strong inhibitory activity at doses of 5-200 mg/kg when administered orally, but BL had obviously stronger inhibitory effects. When tested against ${\lambda}$-carrageenan-induced paw edema in mice, BL showed a potent and synergistic anti-inflammatory effect. In addition, in the acetic acid-induced writhing test, BL was found to have strong analgesic activity at 50-400 mg/kg. Taken together, these results indicate that each of these preparations exert anti-inflammatory activity in vitro and in vivo. In particular, BL showed stronger anti-inflammatory activity than EBP, and these anti-inflammatory effects were partially related to the inhibition of eicosanoid and NO production. BL may be useful for the treatment of human inflammatory disorders.

Xanthoangelol and 4-Hydroxyderricin Are the Major Active Principles of the Inhibitory Activities against Monoamine Oxidases on Angelica keiskei K

  • Kim, Ji Ho;Son, Yeon Kyung;Kim, Gun Hee;Hwang, Keum Hee
    • Biomolecules & Therapeutics
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    • 제21권3호
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    • pp.234-240
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    • 2013
  • Monoamine oxidase inhibitors (MAOI) have been widely used as antidepressants. Recently, there has been renewed interest in MAO inhibitors. The activity-guided fractionation of extracts from Angelica keiskei Koidzumi (A. keiskei K.) led to the isolation of two prenylated chalcones, xanthoangelol and 4-hydroxyderricin and a flavonoid, cynaroside. These three isolated compounds are the major active ingredients of A. keiskei K. to inhibit the MAOs and DBH activities. Xanthoangelol is a nonselective MAO inhibitor, and a potent dopamine ${\beta}$-hydroxylase (DBH) inhibitor. $IC_{50}$ values of xanthoangelol to MAO-A and MAO-B were calculated to be 43.4 ${\mu}M$, and 43.9 ${\mu}M$. These values were very similar to iproniazid, which is a nonselective MAO inhibitor used as a drug against depression. The $IC_{50}$ values of iproniazid were 37 ${\mu}M$, and 42.5 ${\mu}M$ in our parallel examination. Moreover, $IC_{50}$ value of xanthoangelol to DBH was calculated 0.52 ${\mu}M$. 4-Hydroxyderricin is a potent selective MAO-B inhibitor and also mildly inhibits DBH activity. The $IC_{50}$ value of 4-hydroxyderricin to MAO-B was calculated to be 3.43 ${\mu}M$ and this value was higher than that of deprenyl (0.046 ${\mu}M$) used as a positive control for selective MAO-B inhibitor in our test. Cynaroside is a most potent DBH inhibitor. The $IC_{50}$ value of cynaroside to DBH was calculated at 0.0410 ${\mu}M$. Results of this study suggest that the two prenylated chalcones, xanthoangelol and 4-hydroxyderricin isolated from A. keiskei K., are expected for potent candidates for development of combined antidepressant drug. A. keiskei K. will be an excellent new bio-functional food material that has the combined antidepressant effect.

Sophora Flavescens Suppresses Degranulation and Pro-inflammatory Cytokines Production through the Inhibition of NF-${\kappa}B$ (p65) Activation in the RBL-2H3 cells

  • Lyu, Ji-Hyo;Park, Sang-Eun;Hong, Su-Hyun;Kim, Dong-Kyu;Ko, Woo-Shin;Hong, Sang-Hoon
    • 동의생리병리학회지
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    • 제23권1호
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    • pp.206-213
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    • 2009
  • 본 연구는 RBL-2H3 세포에서 고삼의 NF-${\kappa}B$ (p65) 활성 억제를 통한 과립감소와 전염증성 시토카인 억제 효과에 관한 것으로 주요 내용은 다음과 같다. 본 연구에서는 PMA와 A23187로 유발된 흰쥐 백혈병(RBL-2H3) 세포에서 고삼의 항알레르기 효과에 대하여 알아보았다. 고삼은 투여량에 따라 $\beta$-hexosaminidase의 방출과 TNF-$\alpha$, IL-4, COX-2 등의 생성과 발현을 억제하였다. 실험결과 고삼은 $NF-{\kappa}B$ (p65)의 조절을 통하여 항알레르기 효과를 나타내었는데 이는 $I{\kappa}B-{\alpha}$ 저해의 억제와 항염증 시토카인 발현 억제와도 관계가 있다는 내용이다.

느타리버섯의 항암수목자원 배지속 함유성분의 분해능 평가 (Metabolizing analysis according to the sawdust media of the known anticancer trees by Pleurotus ostreatuss)

  • 신유수;양보현;강보연;김현수;이지현;홍윤표;이상원;이찬중;김승유
    • 한국버섯학회지
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    • 제9권4호
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    • pp.186-189
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    • 2011
  • 가래나무(J. mandchurica), 구지뽕나무(C. tricuspidata), 감태나무(L. glauca)는 최근 항암효과가 있다고 보고되고 있는 수목자원이다. 한방에서는 가래나무 수피를 말린 것을 추목피라하며, 소염성 수렴과 해열, 눈을 맑게 하는 등의 효능이 있어 장염, 이질, 설사, 눈이 충혈하고 붓는 통증 등에 처방하고 있으며, 주요성분으로 naphthoquinones, naphthalenyl glucosides, ${\alpha}$-tertalonyl glucopyranosides, diarylheptanoyl glucopyranosides, flavonoids 등의 페놀성 화합물들이 보고되었다. 구지뽕나무는 한방에서 자양, 강장의 효능이 있으며, 신체허약증, 정력 감퇴, 불면증, 시력감퇴 등에 효과가 크며, 부인병 치료와 항암치료에도 처방되고 있다. 구지뽕나무의 주요 성분으로 근피에서 새로운 iso-prenylated xanthone 화합물인 cudraxanthone A, B, C, D, H, I, J 및 K 그리고 isoprenylated flavone 화합물인 cudraflavone A, B cycloartocarpesin, populnin, quercimetrin 등이 알려졌으며, 목부에서는 ${\beta}$-sitosterol glucoside, arthocarpesin, norarthoca-rpetin, 5-O-methyl genistein 등이 분리되어졌다. flavonoid, morin, kaempherol-7-giucoside, poupulnin, stachydrine, proline, glutamicaoid, arginine, asparaginic acid 등의 화합물들이 보고되었다. 또한, 감태나무는 한방에서 열매를 산호초라 하며, 염증을 삭히며 통증을 없애는 효능이 있어, 풍습성 관절염이나 신경통, 손발이 저린 곳, 관절통과 근육통, 배가 차갑고 아픈 곳, 여성의 산후통과 뼈가 허약한 곳이나 허리와 무릎이 아픈 곳에 처방하고 있다. 감태나무의 주요 성분으로 지방유, 정유, cineol, caryophyllene bornylacttate, camphene pinene, limonene 등의 화합물들이 보고되었다. 본 연구는 항암효과가 알려진 가래나무, 구지뽕나무, 감태나무를 느타리버섯의 새로운 톱밥배지자원으로서 활용하여 이들 자원의 함유성분이 담자균류인 느타리버섯에 의해 분해되거나 다른 유도체화합물로 이행되는지를 검토하였다. 3종의 수목자원의 톱밥배지에서 재배한 느타리버섯과 공시재료를 80% 메탄올로 추출하여 조추출물을 조제하고 이를 액체배지에 첨가하여 생육한 느타리버섯 균사체를 HPLC분석 시료로 사용하였다. HPLC를 이용하여 공시재료들의 함유성분들의 크로마토그래피 패턴을 비교 분석한 결과, 가래나무, 구지뽕나무, 감태나무 톱밥배지에서 생육한 느타리버섯은 각각의 수목자원 톱밥배지속의 함유성분을 분해 또는 다른 유도체화합물로 이행시키지 않는 것으로 나타났다. 또한, 수목자원 추출물을 첨가하여 액상배지에서도 느타리버섯 균사체가 이들 추출물의 성분을 분해 또는 다른 유도체화합물로의 이행은 나타나지 않았다. 그러나 이들 추출물은 느타리버섯 균사체의 생육에 영향을 주어 느타리버섯 균사체의 2차대사산물의 생성 및 억제를 하고 있음을 나타냈다.