• 제목/요약/키워드: flavonoid derivatives

검색결과 70건 처리시간 0.026초

Cytotoxic Constituents from Boesenbergia pandurate (Roxb.) Schltr

  • Ching, Amy Yap Li;Lian, Gwendoline Ee Cheng;Rahmani, Mawardi;Khalid, Kaida;Sukari, Mohd Aspollah
    • Natural Product Sciences
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    • 제13권2호
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    • pp.110-113
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    • 2007
  • Five flavonoid derivatives, pinostrobin (1), pinocembrin (2), alpinetin (3), cardamonin (4) and boesenbergin A (5) were isolated from the rhizomes of Boesenbergia pandurata. All compounds were elucidated based on its spectroscopic data and by the comparison with the previous works. 2D NMR technique was used for the structure elucidation of boesenbergin A to complement the data reported previously. The extracts and pure compounds were screened for cytotoxic activity against HL-60 cancer cell lines (human promyelocytic leukemia). Cytotoxic screening showed most of the extracts and pure compounds isolated from the rhizomes of Boesenbergia pandurata were active against HL-60 cancer cell line. The chloroform extract and boesenbergin A showed the most potent cytotoxic activity.

자화지정(Viola mandshurica)의 아미노산과 유용성분 비교 분석 (Comparative Analysis of the Amino Acids and Effective Components from Viola mandshurica)

  • 이양숙;김남우
    • 한국식품저장유통학회지
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    • 제15권5호
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    • pp.699-705
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    • 2008
  • 본 연구는 한방생약재로 사용되고 있는 자화지정의 식품학적 가치와 식품소재로서의 개발 가능성을 검토하기 위하여 국내에서 채집된 자화지정의 기원식물인 제비꽃과 한방재료로 유통, 판매되고 있는 중국산 자화지정을 비교, 분석하였다. 분석 결과 자화지정 꽃의 환원당과 유리당이 각각 10,485.11 mg%와 118.85 mg%로 가장 많았으며, 수용성 단백질과 폴리페놀의 함량도 각각 1,259.26 mg%와 2366.67 mg%로 함량이 높은 것으로 확인되었다. 플라보노이드 함량은 중국산 잎에서 2,370.75 mg%이었으며, 잎은 1,844.43 mg%을 함유하였다. 유리아미노산은 잎(5,345.21 mg%) > 뿌리(4,692.24 mg%) > 꽃(3,807.87 mg%) > 중국산 잎 (3,613.81 mg%)의 순으로 특히 뿌리에는 arginine의 함량이 전체의 55 %이상 차지하였으며 모든 부위에서 valine, aspartic acid, glutamic acid, alanine, arginine 등의 함량이 비교적 높은 것으로 나타났다. 아미노산 유도체는 잎에서 9,058.80 mg%로 가장 많이 함유하였으며 $\alpha$-aminoadipic acid는 모든 부위에서 50% 이상을 함유하였으며 특히 잎에서는 아미노산 유도체(7,124.23 mg%) 중 약 80%를 차지하였다. 무기질 함량은 중국산 잎이 5,917.57 mg%로 가장 높았으며, 모든 부위에서 K, Ca와 Mg의 함량이 매우 높았으며, 특히 잎과 꽃의 95% 이상을 차지하였다. 이상의 결과 국내에서 채집된 자화지정의 잎이 중국산 잎보다는 환원당과 폴리페놀, 플라보노이드 그리고 무기질의 함량은 낮았으나 수용성 단백질과 아미노산을 다량 함유하였으며, 국내에서 채집된 자화지정의 뿌리와 꽃에서도 유용한 유용성분들을 다량 함유하므로 음료나 건강보조식품 등 다양한 기능성 제품 개발에 이용될 수 있는 한방약용자원인 것으로 사료된다.

참느릅나무에서 추출된 catechin 유도체 화합물의 멜라닌 생성 억제 효과 (Tyrosinase Inhibition-mediated Anti-melanogenic Effects by Catechin Derivatives Extracted from Ulmus parvifolia)

  • 황태혁;이효정;강동민;문경미;유재철;안미정;문동규;우동균
    • 생명과학회지
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    • 제33권2호
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    • pp.169-175
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    • 2023
  • 자외선으로 야기되는 피부조직의 손상에 대한 방어기전으로 멜라닌세포는 멜라닌 색소를 생산한다. 이러한 멜라닌 생성에는 tyrosinase 효소가 중추적인 역할을 수행한다. 그러나 과다한 멜라닌 생성은 피부조직에 주근깨와 검버섯 등의 과다 색소침착 병변을 일으킨다. 따라서 tyrosinase 발현이나 활성을 조절함으로써, 과도한 멜라닌 생성을 억제하는 물질을 발굴하는 것은 임상적인 의미가 있다. Catechin은 tyrosinase 발현을 저해함으로써 멜라닌 생성을 억제하는 화합물로 알려져 있다. 본 연구에서는 B16F10 마우스 흑색종 세포주와 버섯에서 추출된 tyrosinase를 사용하여, 참느릅나무의 줄기 껍질에서 추출 및 동정된 catechin 유도체 화합물(C5A, C7A, C7G, 및 C7X)의 멜라닌 생성 억제 효능을 검증하였다. 먼저, B16F10 세포주에서, 세포독성을 나타내지 않는 농도의 catechin 유도체 화합물 처리는, 모두α-MSH로 촉진된 멜라닌 생합성을 억제하는 효능을 보였다. Catechin 유도체 화합물의 이러한 효능은 멜라닌 생합성 저해제로 잘 알려진 kojic acid와 비슷한 수준이였다. 또한, C5A와 C7A는 버섯에서 추출된 tyrosinase의 효소 활성을 통계적으로 유의하게 억제하였다. 또한, 컴퓨터 분석을 통해 C5A와 C7A는 kojic acid와 유사한 수준으로 tyrosinase의 active site에 결합할 것으로 예측되었다. 이에 더하여, 4종류의 catechin 유도체 화합물 모두가 α-MSH 처리된 B16F10 세포주에서 tyrosinase 단백질 발현을 감소시켰다. 본 연구결과를 종합하면, 참느릅나무에서 추출/동정된 catechin 유도체 화합물은 멜라닌세포의 멜라닌 생성을 효과적으로 억제하였다. 따라서, 본 연구결과는 이러한 catechin 유도체 화합물이 피부의 과다 색소침착 질환 제어를 위한 새로운 조절 물질로 응용될 수 있음을 제시한다.

한국산 씀바귀의 Flavonoid 성분에 관한 연구 (Flavonoidal constituent in Korean Lactuca dentata Makino)

  • 정강현;윤광로;김준평
    • 한국식생활문화학회지
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    • 제9권2호
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    • pp.131-136
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    • 1994
  • 한국산 씀바귀(Lactuca dentata Makino)의 ethylacetate 추출물에서 6 종류의 flavonoid 성분이 TLC에 의해서 검출 되었으며, 이들은 극성에 따라서 A에서 F가지 명명되었다. 그들 중 주성분으로 생각되는 물질 E를 column chromatography을 이용하여 분리정제 하였다. 물질 E의 녹는 점은 $249.5^{\circ}C-251^{\circ}C$ 로 나타났으며, 그 구조를 밝히기 위하여, 물질 E와 이를 가수분해한 genin에 대한 여러가지 shift reagent에서 UV와 IR분석을 하고 또한 물질 E와 그의 acetyl 유도체에 대한 NMR 분석을 하였으며 물질 E에 결합된 당은 TLC에 의하여 확인하였다. 이와같은 분석 결과에서 물질 E는 luteolin 모핵에 glucose가 결합된 $luteolin-7-0-{\beta}-D-glucoside$로서 확인되었다.

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TI-I-174, a Synthetic Chalcone Derivative, Suppresses Nitric Oxide Production in Murine Macrophages via Heme Oxygenase-1 Induction and Inhibition of AP-1

  • Kim, Mi Jin;Kadayat, Taraman;Kim, Da Eun;Lee, Eung-Seok;Park, Pil-Hoon
    • Biomolecules & Therapeutics
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    • 제22권5호
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    • pp.390-399
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    • 2014
  • Chalcones (1,3-diaryl-2-propen-1-ones), a flavonoid subfamily, are widely known for their anti-inflammatory properties. Propenone moiety in chalcones is known to play an important role in generating biological responses by chalcones. In the present study, we synthesized chalcone derivatives structurally modified in propenone moiety and examined inhibitory effect on nitric oxide (NO) production and its potential mechanisms. Among the chalcone derivatives used for this study, TI-I-174 (3-(2-Hydroxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one) most potently inhibited lipopolysaccharide (LPS)-stimulated nitrite production in RAW 264.7 macrophages. TI-I-174 treatment also markedly inhibited inducible nitric oxide synthase (iNOS) expression. However, TI-I-174 did not significantly affect production of IL-6, cyclooxygenase-2 (COX-2) and tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$), implying that TI-I-174 inhibits production of inflammatory mediators in a selective manner. Treatment of macrophages with TI-I-174 significantly inhibited transcriptional activity of activator protein-1 (AP-1) as determined by luciferase reporter gene assay, whereas nuclear factor-${\kappa}B$ (NF-${\kappa}B$) activity was not affected by TI-I-1744. In addition, TI-I-174 significantly inhibited activation of c-Jun-N-Terminal kinase (JNK) without affecting ERK1/2 and p38MAPK, indicating that down-regulation of iNOS gene expression by TI-I-174 is mainly attributed by blockade of JNK/AP-1 activation. We also demonstrated that TI-I-174 treatment led to an increase in heme oxygenase-1 (HO-1) expression both at mRNA and protein level. Transfection of siRNA targeting HO-1 reversed TI-I-174-mediated inhibition of nitrite production. Taken together, these results indicate that TI-I-174 suppresses NO production in LPS-stimulated RAW 264.7 macrophages via induction of HO-1 and blockade of AP-1 activation.

Inhibition of Carcinogen-Activating Cytochrome P450 Enzymes by Xenobiotic Chemicals in Relation to Antimutagenicity and Anticarcinogenicity

  • Shimada, Tsutomu
    • Toxicological Research
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    • 제33권2호
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    • pp.79-96
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    • 2017
  • A variety of xenobiotic chemicals, such as polycyclic aromatic hydrocarbons (PAHs), aryl- and heterocyclic amines and tobacco related nitrosamines, are ubiquitous environmental carcinogens and are required to be activated to chemically reactive metabolites by xenobiotic-metabolizing enzymes, including cytochrome P450 (P450 or CYP), in order to initiate cell transformation. Of various human P450 enzymes determined to date, CYP1A1, 1A2, 1B1, 2A13, 2A6, 2E1, and 3A4 are reported to play critical roles in the bioactivation of these carcinogenic chemicals. In vivo studies have shown that disruption of Cyp1b1 and Cyp2a5 genes in mice resulted in suppression of tumor formation caused by 7,12-dimethylbenz[a]anthracene and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, respectively. In addition, specific inhibitors for CYP1 and 2A enzymes are able to suppress tumor formation caused by several carcinogens in experimental animals in vivo, when these inhibitors are applied before or just after the administration of carcinogens. In this review, we describe recent progress, including our own studies done during past decade, on the nature of inhibitors of human CYP1 and CYP2A enzymes that have been shown to activate carcinogenic PAHs and tobacco-related nitrosamines, respectively, in humans. The inhibitors considered here include a variety of carcinogenic and/or non-carcinogenic PAHs and acethylenic PAHs, many flavonoid derivatives, derivatives of naphthalene, phenanthrene, biphenyl, and pyrene and chemopreventive organoselenium compounds, such as benzyl selenocyanate and benzyl selenocyanate; o-XSC, 1,2-, 1,3-, and 1,4-phenylenebis(methylene)selenocyanate.

Inhibitory Effects of Naringenin and Its Novel Derivatives on Hyaluronidase

  • Moon, Sun-Hee;Kim, Kee-Tae;Lee, Na-Kyoung;Han, Ye-Sun;Nah, Seung-Yeol;Cho, Ssang-Goo;Park, Yong-Sun;Paik, Hyun-Dong
    • Food Science and Biotechnology
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    • 제18권1호
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    • pp.267-270
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    • 2009
  • Naringenin is a bioactive flavanone containing antioxidative, anti-inflammatory, and anticarcinogenic properties. The inhibitory effects on hyaluronidase of naringenin and its novel derivatives were evaluated. Among these flavonoids at $200{\mu}M$ concentration, 7-O-butyl naringenin had the highest inhibitory effect on hyaluronidase with 44.84%. In addition, For naringenin at concentrations of 0, 150, and $190{\mu}M$, the apparent Michaelis constants ($_{app}K_m$) were calculated to be $0.60{\pm}0.02$, $0.43{\pm}0.02$, and $0.41{\pm}0.01\;mg/mL$ of substrate, respectively; for 7-O-butyl naringenin at 0, 20, and $30{\mu}M$ concentrations, those were $0.44{\pm}0.03$ and $0.27{\pm}0.03\;mg/mL$, respectively. The $V_{max}$ values at 150 and $190{\mu}M$ naringenin were $0.59{\pm}0.02$ and $0.56{\pm}0.01\;mg/mL/min$, respectively; and those at 20 and $30{\mu}M$ 7-O-butyl naringenin were $0.50{\pm}0.02$ and $0.33{\pm}0.02\;mg/mL/min$, respectively. However, the slopes of each inhibitory reaction were not significantly different. Therefore, naringenin and 7-O-butyl naringenin were shown to be uncompetitive inhibitors. These results demonstrate the potential use of 7-O-butyl naringenin as an anti-inflammatory substance.

Macakurzin C Derivatives as a Novel Pharmacophore for Pan-Peroxisome Proliferator-Activated Receptor Modulator

  • Hyejin Ko;Seungchan An;Hongjun Jang;Sungjin Ahn;In Guk Park;Seok Young Hwang;Junpyo Gong;Soyeon Oh;Soo Yeon Kwak;Won Jun Choi;Hyoungsu Kim;Minsoo Noh
    • Biomolecules & Therapeutics
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    • 제31권3호
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    • pp.312-318
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    • 2023
  • The natural flavonoid macakurzin C (1) exhibited adiponectin biosynthesis-inducing activity during adipogenesis in human bone marrow mesenchymal stem cells and its molecular mechanism was directly associated with a pan-peroxisome proliferator-activated receptor (PPAR) modulator affecting all three PPAR subtypes α, γ, and δ. In this study, increases in adiponectin biosynthesis-inducing activity by macakurzin C derivatives (2-7) were studied. The most potent adiponectin biosynthesis-inducing compound 6, macakurzin C 3,5-dimethylether, was elucidated as a dual PPARα/γ modulator. Compound 6 may exhibit the most potent activity because of the antagonistic relationship between PPARδ and PPARγ. Docking studies revealed that the O-methylation of macakurzin C to generate compound 6 significantly disrupted PPARδ binding. Compound 6 has therapeutic potential in hypoadiponectinemia-related metabolic diseases.

구아바 잎 추출물 및 컬럼크로마토그래피를 이용한 메탄올 분획물의 항산화 활성 (Antioxidant activity of ethanol extract and methanol fractions via column chromatography from Psidium guajava Leaf)

  • 최병규
    • Journal of Applied Biological Chemistry
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    • 제66권
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    • pp.266-271
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    • 2023
  • 본 실험에서는 에탄올로 추출한 Psidium guajava 잎과 컬럼크로마토그래피를 이용한 메탄올 분획물의 항산화 능력을 측정하기 위해 DPPH, ABTS 라디컬소거능법, 총 페놀, 플라보노이드법, SOD assay법을 활용하였다. 항산화 활성 결과에서 40, 60% 메탄올 분획물이 의미있는 측정값을 나타냈고, 두 분획물을 선정하여 HPLC와 핵자기공명(NMR)을 활용한 화학적 분석을 통해 주요 성분의 분리 및 물질탐색을 진행하였다. HPLC 정제를 통해 quercitrin (1)와 isoquercetin (2) 두 종류의 quercetin 유도체를 분리 및 구조 동정하였다. SOD assay 결과에서 컬럼크로마토그래피법을 활용하여 얻은 몇몇의 분획물과 단일물질로 분리한 화합물들은 추출물보다 향상된 항산화 활성을 보였다.

Two New Flavonoids from Dragon's Blood of Dracaena cambodiana

  • Mei, Wen-Li;Luo, Ying;Wang, Hui;Shen, Hai-Yan;Zeng, Yan-Bo;Dai, Hao-Fu
    • Bulletin of the Korean Chemical Society
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    • 제34권6호
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    • pp.1791-1794
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    • 2013
  • Phytochemical investigation on dragon's blood of Dracaena cambodiana led to the discovery of two new flavonoid derivatives, cambodianin G (1) and cambodianin H (2). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. The two compounds were observed to exhibit antibacterial activities against Staphylococcus aureus, and compound 1 showed cytotoxicities against K562 and SGC-7901 cell lines.