• Title/Summary/Keyword: Synthetic flavonoid

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Effect of Quercetin on Auxin-induced Ethylene Production in Barley Coleoptiles (Quercetin이 보리 자엽초에서 옥신에 의해 유도되는 에틸렌 생성에 미치는 영향)

  • 이준승
    • Journal of Plant Biology
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    • v.35 no.4
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    • pp.409-414
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    • 1992
  • Effect of quercetin, a kind of natural plant flavonoids, on auxin-induced ethylene production in barley coleoptiles was studied. Auxin-induced ethylene production was apparently stimulated by quercetin. This stimulatory effect of quercetin appeared after 4 h of incubation period. Ethylene production was stimulated 200% over the control after 8 h of incubation by $3{\times}10^{-5}\;M$ quercetin. The quercetin effect was most prominent at $10^{-4}\;M$ of IAA. Ethylene production induced by the synthetic auxin, 2,4-D and NAA, was not significantly affected by quercetin. Also ACC-based ethylene production was unaffected by the flavonoid. In an effort to elucidate mechanisms of quercetin action on auxin-induced ethylene production, the effect of quercetin on 1M metabolism was studied. Data obtained from these experiments indicate that quercetin treatment resulted in about 90% inhibition of IAA oxidase activity. IAA ($3{\times}10^{-5}\;M$) conjugation was found to be not affected by quercetin. This results suggest that the stimulatory effect of quercetin on auxin-induced ethylene production may be due to the fact that quercetin inhibits 1M oxidase activity, thus increasing the free IAA level.

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Antifungal Activity of Eucalyptus-Derived Phenolics Against Postharvest Pathogens of Kiwifruits

  • Oh, Soon-Ok;Kim, Jung-A;Jeon, Hae-Sook;Park, Jong-Cheol;Koh, Young-Jin;Hur, Hyun;Hur, Jae-Seoun
    • The Plant Pathology Journal
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    • v.24 no.3
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    • pp.322-327
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    • 2008
  • Antifungal activities of natural substrances from Eucalyptus darlympleana, E. globules, E. gunnii and E. unigera were evaluated against postharvest pathogens of kiwifruits, Botrytis cinerea, Botryosphaeria dothidea, and Diaporthe actinidiae, to screen effective natural substances as an alternative to chemical fungicides. Methanol extract of the Eucalyptus trees showed strong antagonistic activity against the pathogenic fungi. Among them, E. unigera and E. darlympleana effectively inhibited mycelial growth of the pathogens. For chemical identification of the antifungal substances, the methanol extract of E. darlympleana leaves was successively partitioned with $CH_2Cl_2$, EtOAc, n-BuOH and $H_2O$. Among the fractions, $CH_2Cl_2$ and n-BuOH showed strong inhibitory activity of mycelial growth of the fungi. Five compounds were isolated from EtOAc and n-BuOH fractions subjected to $SiO_2$ column chromatography. Two phenolic compounds(gallic acid and 3,4-dihydroxybenzoic acid) and three flavonoid compounds(quercetin, quercetin-3-O-$\alpha$-L-rhamnoside, quercetin-3-O-$\beta$-glucoside) were identified by $^1H$-NMR and $^{13}C$-NMR spectroscopy. Among them, only gallic acid was found to be effective in mycelial growth and spore germination of B. cinerea at relatively high concentrations. The results suggest that gallic acid can be a safer and more acceptable alternative to current synthetic fungicides controlling soft rot decay of kiwifruit during postharvest storage.

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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    • v.22 no.5
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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.

Comparison of Biological Activities of Extracts from Different Parts and Solvent Fractions in Cornus kousa Buerg (산딸나무의 부위별 추출물 및 용매 분획물의 생리활성 비교)

  • Kim, Young-Jung;Jeong, Jin-A;Kwon, Su-Hyun;Lee, Cheol-Hee
    • Korean Journal of Plant Resources
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    • v.21 no.1
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    • pp.28-35
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    • 2008
  • Several extracts of different parts and solvent fractions of Cornus kousa were obtained and their functional material contents, antioxidant activities and tyrosinase inhibition effects were determined. Content of total polyphenols and flavonoids contents in flower were 169.638 $mg{\cdot}g^{-1}$ and 25.418 $mg{\cdot}g^{-1}$, respectively, which were much higher than those of other parts. Also, flower extracts showed the strongest effects on DPPH and ABTS radicals scavenging and ferrous ion chelating. In flower, leaf, and stem extracts, inhibition effects on peroxidation of linoleic acid determined by ferric thiocyanate(FTC) method were higher than a synthetic antioxidant, BHT. Tyrosinase inhibition activities were shown only in flower extract. Flower and leaf extracts, showing high biological activities in various system, were successively reextracted with n-hexane, chloroform, ethylacetate and n-butanol. Total polyphenol contents of water fractions were higher than any other solvent fractions in both flower and leaf, 67.006 $mg{\cdot}g^{-1}$ and 67.739 $mg{\cdot}g^{-1}$, respectively. But total flavonoid contents were higher in ethyl acetate fraction for flower extract and butanol fraction for leaf extract. Among the solvent fractions, the highest efficiency of free radical scavenging activities was obtained in ethyl acetate fraction for flower extract and n-butanol fraction for leaf extract. Tyrosinase inhibition activities were higher in water fraction for both flower and leaf extracts, 49.24% and 31.8%, respectively.

Identification of Antioxidative Components from Ethanol Extracts of Dalbergia odorifera T.CHEN (강진향(Dalbergia odorifera T.CHEN) 에탄올 추출물로부터 항산화 활성물질의 구조동정)

  • Choi, Ung;Kim, In-Won;Baek, Nam-In;Shin, Dong-Hwa
    • Korean Journal of Food Science and Technology
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    • v.34 no.5
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    • pp.893-897
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    • 2002
  • The chloroform layer from 75% ethanol extract of Dalbergia odorifera T.CHEN showed strong antioxidative activity on lard and palm oil as tested by Rancimat method. Antioxidative active compound isolated and identified by silica gel column chromatography, thin layer chromatography, mass spectrophotometer, $^1H-NMR$ and $^{13}C-NMR$ was identified as mucronulatol (3(R&S)-3,7-Dihydroxy-2',4-dimethoxyisoflavan). Results of Rancimat method revealed the induction period of Mucronulatol increased longer than those of synthetic antioxidant, BHA and BHT, at the same concentration. Mucronulatol combined with ${\delta}-tocopherol(200ppm)$, and with ascorbic acid (200 ppm) and citric acid (200 ppm) on lard and palm oil, respectively, showed strong synergistic effects.

Antioxidant Effect of 80% Ethanol Extracts Obtained from Three Dendranthema Species (국화과 Dendranthema속 식물 3종 80% 에탄올 추출물의 항산화 효과)

  • Woo, Jeong-Hyang;Shin, So-Lim;Lee, Cheol-Hee
    • Korean Journal of Plant Resources
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    • v.23 no.1
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    • pp.47-53
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    • 2010
  • Flowers and shoots of three species of Dendranthema boreale, Dendranthema indicum, Dendranthema zawdskii var. lucidum, were extracted with 80% ethanol by reflux, and polyphenol content, scavenging activity on DPPH and ABTS radicals, ferrous ion chelating effects and inhibition effects on lipid peroxidation were analyzed. Total polyphenol and flavonoid contents were highest in D. zawdskii var. lucidum, especially in the flower part. Scavenging activity on DPPH and ABTS was also highest in D. zawdskii var. lucidum flower with less activity in shoot. Ferrous ion chelating effects was highest with D. boreale flower and lowest in D. zawdskii var. lucidum flower. Inhibition activity on lipid peroxidation was highest in D. zawdskii var. lucidum shoot with 41.01% inhibition activity showing 32 days after reaction, which is higher than synthetic antioxidant BHT. Due to higher antioxidant level and activity of shoot and flower of D. zawdskii var. lucidum is promising material for natural plant antioxidant. It was also shown that antioxidant activity is different according to plant part ever in same plant, and proper plant species should be used for antioxidant after careful studies.

Pathogen, Insect and Weed Control Effects of Secondary Metabolites from Plants (식물유래 2차 대사물질의 병충해 및 잡초 방제효과)

  • Kim, Jong-Bum
    • Applied Biological Chemistry
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    • v.48 no.1
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    • pp.1-15
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    • 2005
  • Pathogens, insects and weeds have significantly reduced agricultural productivity. Thus, to increase the productivity, synthetic agricultural chemicals have been overused. However, these synthetic compounds that are different from natural products cannot be broken down easily in natural systems, causing the destruction of soil quality and agricultural environments and the gradually difficulty in continuous agriculture. Now agriculture is faced with the various problems of minimizing the damage in agricultural environments, securing the safety of human health, while simultaneously increasing agricultural productivity. Meanwhile, plants produce secondary metabolites to protect themselves from external invaders and to secure their region for survival. Plants infected with pathogens produce antibiotics phytoalexin; monocotyledonous plants produce flavonoids and diterpenoids phytoalexins, and dicotylodoneous plant, despite of infected pathogens, produce family-specific phytoalexin such as flavonoids in Leguminosae, indole derivatives in Cruciferae, sesquitepenoids in Solanaceae, coumarins in Umbelliferae, making the plant resistant to specific pathogen. Growth inhibitor or antifeedant substances to insects are terpenoids pyrethrin, azadirachtin, limonin, cedrelanoid, toosendanin and fraxinellone/dictamnine, and terpenoid-alkaloid mixed compounds sesquiterpene pyridine and norditerpenoids, and azepine-, amide-, loline-, stemofoline-, pyrrolizidine-alkaloids and so on. Also plants produces the substances to inhibit other plant growths to secure the regions for plant itself, which is including terpenoids essential oil and sesquiterpene lactone, and additionally, benzoxazinoids, glucosinolate, quassinoid, cyanogenic glycoside, saponin, sorgolennone, juglone and lots of other different of secondary metabolites. Hence, phytoalexin, an antibiotic compound produced by plants infected with pathogens, can be employed for pathogen control. Terpenoids and alkaloids inhibiting insect growth can be utilized for insect control. Allelochemicals, a compound released from a certain plant to hinder the growth of other plants for their survival, can be also used directly as a herbicides for weed control as well. Therefore, the use of the natural secondary metabolites for pest control might be one of the alternatives for environmentally friendly agriculture. However, the natural substances are destroyed easily causing low the pest-control efficacy, and also there is the limitation to producing the substances using plant cell. In the future, effects should be made to try to find the secondary metabolites with good pest-control effect and no harmful to human health. Also the biosynthetic pathways of secondary metabolites have to be elucidated continuously, and the metabolic engineering should be applied to improve transgenics having the resistance to specific pest.