• Title/Summary/Keyword: Flavonoid biosynthesis

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Genomics Reveals Traces of Fungal Phenylpropanoid-flavonoid Metabolic Pathway in the Filamentous Fungus Aspergillus oryzae

  • Juvvadi Praveen Rao;Seshime Yasuyo;Kitamoto Katsuhiko
    • Journal of Microbiology
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    • v.43 no.6
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    • pp.475-486
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    • 2005
  • Fungal secondary metabolites constitute a wide variety of compounds which either playa vital role in agricultural, pharmaceutical and industrial contexts, or have devastating effects on agriculture, animal and human affairs by virtue of their toxigenicity. Owing to their beneficial and deleterious characteristics, these complex compounds and the genes responsible for their synthesis have been the subjects of extensive investigation by microbiologists and pharmacologists. A majority of the fungal secondary metabolic genes are classified as type I polyketide synthases (PKS) which are often clustered with other secondary metabolism related genes. In this review we discuss on the significance of our recent discovery of chalcone synthase (CHS) genes belonging to the type III PKS superfamily in an industrially important fungus, Aspergillus oryzae. CHS genes are known to playa vital role in the biosynthesis of flavonoids in plants. A comparative genome analyses revealed the unique character of A. oryzae with four CHS-like genes (csyA, csyB, csyC and csyD) amongst other Aspergilli (Aspergillus nidulans and Aspergillus fumigatus) which contained none of the CHS-like genes. Some other fungi such as Neurospora crassa, Fusarium graminearum, Magnaporthe grisea, Podospora anserina and Phanerochaete chrysosporium also contained putative type III PKSs, with a phylogenic distinction from bacteria and plants. The enzymatically active nature of these newly discovered homologues is expected owing to the conservation in the catalytic residues across the different species of plants and fungi, and also by the fact that a majority of these genes (csyA, csyB and csyD) were expressed in A. oryzae. While this finding brings filamentous fungi closer to plants and bacteria which until recently were the only ones considered to possess the type III PKSs, the presence of putative genes encoding other principal enzymes involved in the phenylpropanoid and flavonoid biosynthesis (viz., phenylalanine ammonia-lyase, cinnamic acid hydroxylase and p-coumarate CoA ligase) in the A. oryzae genome undoubtedly prove the extent of its metabolic diversity. Since many of these genes have not been identified earlier, knowledge on their corresponding products or activities remain undeciphered. In future, it is anticipated that these enzymes may be reasonable targets for metabolic engineering in fungi to produce agriculturally and nutritionally important metabolites.

Antioxidant Components from Broussonetia kazinoki (닥나무 뿌리껍질의 항산화 성분)

  • Lee, Hwa-Jin;Park, Jae-Hyun;Jang, Dong-Il;Ryu, Jae-Ha
    • YAKHAK HOEJI
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    • v.41 no.4
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    • pp.439-443
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    • 1997
  • From the root bark of Broussonetia kazinoki (Moraceae) two antioxidant components were identified. Their structures were determined as kazinol A (1) and kazinol E (2) (is oprenylated flavan and isoprenylated 1,3-diphenyl propan derivatives) by comparing NMR data with those of the reported compounds from relative plants. The antioxidant activity of 1 and 2 were monitored by the method of DPPH radical scavenging activity, whose $SC_{50}$ values were $41.4{\mu}M\;and\;33.4{\mu}M$, respectively. These compounds also exhibited inhibitory activity against tyrosinase, which is the sole key enzyme for the melanin biosynthesis and play a role in conversion of tyrosine to dopa, and dopa to dopaquinone. The antioxidant effect and the suppression of melanin biosynthesis are useful for anti-aging, increasing vitality in the incidence of major degenerative diseases, and cosmetic products in relation to hyperpigmentation.

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Light modulates the transcriptomic accumulation of anthocyanin biosynthetic pathway genes in red and white grapes

  • Puspa Raj Poudel ;Kazuya Koyama ;Nami Goto-Yamamoto
    • Journal of Plant Biotechnology
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    • v.49 no.4
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    • pp.292-2999
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    • 2022
  • Anthocyanin, an important component in the grape berry skin, strongly affects grape quality. The transcription factors VvMYBA1 and VvMYBA2 (VvMYBA1/2) control anthocyanin biosynthesis. In addition, cultivation and environmental factors, such as light, influence anthocyanin accumulation. The present study aimed to clarify the effect of shading (reduced light condition) on the transcriptomic regulation of anthocyanin biosynthesis using a red-wine grape cultivar, Vitis vinifera 'Pinot Noir', and its white mutant, 'Pinot Blanc', caused by the deletion of the red allele of VvMYBA1/2. The grape berry skins were analyzed for anthocyanin content and global gene transcription accumulation. The microarray data were later validated by quantitative real-time PCR. A decisive influence of VvMYBA1/2 on the expression of an anthocyanin-specific gene, UDP glucose: flavonoid 3-O-glucosyltransferase, was observed as expected. In contrast, upstream genes of the pathway, which are shared by other flavonoids, were also expressed in 'Pinot Blanc', and the mRNA levels of some of these genes decreased in both cultivars on shading. Thus, the involvement of light-sensitive transcription factor(s) other than VvMYBA1/2 was suggested for the expression control of the upstream genes of the anthocyanin biosynthetic pathway. Furthermore, it was suggested that the effects of these factors are different among isogenes.

Antioxidant capacity in seedling of colored-grain wheat under water deficit condition

  • Kim, Dae Yeon;Hong, Min Jeong;Jung, Woo Joo;Seo, Yong Weon
    • Proceedings of the Korean Society of Crop Science Conference
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    • 2017.06a
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    • pp.140-140
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    • 2017
  • Nutritious and functional foods from crop have received great attention in recent years. Colored-grain wheat contains high phenolic compound and a large number of flavonoid. The anthocyanin and polyphenolic synthesis and accumulation is generally stimulated in response to biotic or abiotic stresses. Here, we analyzed genome wide transcripts in seedling of colored-grain wheat response to ABA and PEG treatment. About 900 and 1500 transcripts (p-value < 0.05) from ABA and PEG treatment were aligned to IWGSC1+popseq DB which is composed of over 110,000 transcripts including 100,934 coding genes. NR protein sequences of Poaceae from NCBI and protein sequence of transcription factors originated from 83 species in plant transcription factor database v3.0 were used for annotation of putative transcripts. Gene ontology analysis were conducted and KEGG mapping was performed to show expression pattern of biosynthesis genes related in flavonoid, isoflavonoid, flavons and anthocyanin biopathway. DroughtDB (http://pgsb.helmholtz-muenchen.de/droughtdb/) was used for detection of DEGs to explain that physiological and molecular drought avoidance by drought tolerance mechanisms. Drought response pathway, such as ABA signaling, water and ion channels, detoxification signaling, enzymes of osmolyte biosynthesis, phospholipid metabolism, signal transduction, and transcription factors related DEGs were selected to explain response mechanism under water deficit condition. Anthocyanin, phenol compound, and DPPH radical scavenging activity were measured and antioxidant activity enzyme assays were conducted to show biochemical adaptation under water deficit condition. Several MYB and bHLH transcription factors were up-regulated in both ABA and PEG treated condition, which means highly expressed MYB and bHLH transcription factors enhanced the expression of genes related in the biosynthesis pathways of flavonoids, such as anthocyanin and dihydroflavonols in colored wheat seedlings. Subsequently, the accumulation of total anthocyanin and phenol contents were observed in colored wheat seedlings, and antioxidant capacity was promoted by upregulation of genes involved in maintaining redox state and activation of antioxidant scavengers, such as CAT, APX, POD, and SOD in colored wheat seedlings under water deficit condition. This work may provide valuable and basic information for further investigation of the molecular responses of colored-grain wheat to water deficit stress and for further gene-based studies.

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Accumulation of Flavonols in Response to Ultraviolet-B Irradiation in Soybean Is Related to Induction of Flavanone 3-β-Hydroxylase and Flavonol Synthase

  • Kim, Bong Gyu;Kim, Jeong Ho;Kim, Jiyoung;Lee, Choonghwan;Ahn, Joong-Hoon
    • Molecules and Cells
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    • v.25 no.2
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    • pp.247-252
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    • 2008
  • There are several branch points in the flavonoid synthesis pathway starting from chalcone. Among them, the hydroxylation of flavanone is a key step leading to flavonol and anthocyanin. The flavanone 3-${\beta}$-hydroxylase (GmF3H) gene was cloned from soybean (Glycine max cultivar Sinpaldal) and shown to convert eriodictyol and naringenin into taxifolin and dihydrokaempferol, respectively. The major flavonoids in this soybean cultivar were found by LC-MS/MS to be kamepferol O-triglycosides and O-diglycosides. Expression of GmF3H and flavonol synthase (GmFLS) was induced by ultraviolet-B (UV-B) irradiation and their expression stimulated accumulation of kaempferol glycones. Thus, GmF3H and GmFLS appear to be key enzymes in the biosynthesis of the UV-protectant, kaempferol.

Study of antioxidation activity and melanocyte effect of Pueraria Lobata Root Extract (갈근추출물의 항산화 활성 및 멜라닌세포 효과에 관한 연구)

  • Moon, Ji-sun;Lee, Jin-Hee;Kim, Young-Bae
    • Journal of the Korean Applied Science and Technology
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    • v.34 no.2
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    • pp.418-425
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    • 2017
  • This study investigated antioxidation activity through the content of total polyphenol, that of flavonoid and DPPH radical scavenging activity and measured the cytotoxicity against B16F10 melanoma and inhibiting function of melanin biosynthesis to evaluate antioxidation activity and melanocyte effect of pueraria lobata root extract. As the results of study, it was recognized that the toxicity did not show against B16F10 melanoma and the increase of generating melanin was inhibited as the results of measuring the inhibition function of melanin biosynthesis after inducing the generation of melanin by ${\alpha}$-MSH against B16F10 melanoma cell. The high contents of polyphenol and flavonoid was found as the contents of pueraria lobata root extract increases and DPPH radical scavenging activity as the results of antioxidation activity. Through this study, it was recognized that pueraria lobata root extract has the feasibility that can be used as the material of cosmetics as it has the excellent effect of antioxidation activity and inhibiting the generation of melanin against melanocyte, low toxicity against skin cell and its safety against melanocyte of skin was found.

Transcriptome analysis of a medicinal plant, Pistacia chinensis

  • Choi, Ki-Young;Park, Duck Hwan;Seong, Eun-Soo;Lee, Sang Woo;Hang, Jin;Yi, Li Wan;Kim, Jong-Hwa;Na, Jong-Kuk
    • Journal of Plant Biotechnology
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    • v.46 no.4
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    • pp.274-281
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    • 2019
  • Pistacia chinensis Bunge has not only been used as a medicinal plant to treat various illnesses but its young shoots and leaves have also been used as vegetables. In addition, P. chinensis is used as a rootstock for Pistacia vera (pistachio). Here, the transcriptome of P. chinensis was sequenced to enrich genetic resources and identify secondary metabolite biosynthetic pathways using Illumina RNA-seq methods. De novo assembly resulted in 18,524 unigenes with an average length of 873 bp from 19 million RNA-seq reads. A Kyoto Encyclopedia of Genes and Genomes (KEGG) annotation tool assigned KO (KEGG orthology) numbers to 6,553 (36.2%) unigenes, among which 4,061 unigenes were mapped into 391 different metabolic pathways. For terpenoid backbone and carotenoid biosynthesis pathways, 44 and 22 unigenes encode enzymes corresponding to 30 and 16 entries, respectively. Twenty-two unigenes encode proteins for 16 entries of the carotenoid biosynthesis pathway. As for the phenylpropanoid and flavonoid biosynthesis pathways, 63 and 24 unigenes were homologous to 17 and 14 entry proteins, respectively. Mining of simple sequence repeat identified 2,599 simple sequence repeats from P. chinensis unigenes. The results of the present study provide a valuable resource for in-depth studies on comparative and functional genomics to unravel the underlying mechanisms of the medicinal properties of Pistacia L.

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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    • v.31 no.3
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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.

Transcriptomic Insights into Abies koreana Drought Tolerance Conferred by Aureobasidium pullulans AK10

  • Jungwook Park;Mohamed Mannaa;Gil Han;Hyejung Jung;Hyo Seong Jeon;Jin-Cheol Kim;Ae Ran Park;Young-Su Seo
    • The Plant Pathology Journal
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    • v.40 no.1
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    • pp.30-39
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    • 2024
  • The conservation of the endangered Korean fir, Abies koreana, is of critical ecological importance. In our previous study, a yeast-like fungus identified as Aureobasidium pullulans AK10, was isolated and shown to enhance drought tolerance in A. koreana seedlings. In this study, the effectiveness of Au. pullulans AK10 treatment in enhancing drought tolerance in A. koreana was confirmed. Furthermore, using transcriptome analysis, we compared A. koreana seedlings treated with Au. pullulans AK10 to untreated controls under drought conditions to elucidate the molecular responses involved in increased drought tolerance. Our findings revealed a predominance of downregulated genes in the treated seedlings, suggesting a strategic reallocation of resources to enhance stress defense. Further exploration of enriched Kyoto Encyclopedia of Genes and Genomes pathways and protein-protein interaction networks revealed significant alterations in functional systems known to fortify drought tolerance, including the terpenoid backbone biosynthesis, calcium signaling pathway, pyruvate metabolism, brassinosteroid biosynthesis, and, crucially, flavonoid biosynthesis, renowned for enhancing plant drought resistance. These findings deepen our comprehension of how AK10 biostimulation enhances the resilience of A. koreana to drought stress, marking a substantial advancement in the effort to conserve this endangered tree species through environmentally sustainable treatment.

Molecular cloning, sequences analysis and in vitro expression of the dihydroflavonol 4-reductase gene from Gypsophila paniculata L. (안개초(Gypsophila paniculata L.)로부터 dihydroflavonol 4-reductase 유전자의 분리 및 분석)

  • Min, Byung-Whan;Cheong, Dong-Chun
    • Journal of Plant Biotechnology
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    • v.37 no.1
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    • pp.89-95
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    • 2010
  • Dihydroflavonol 4-reductase (DFR) is a key enzyme of the flavonoid biosynthesis pathway which catalyses the NADPH-dependent reduction of 2R,3R-trans-dihydroflavonols to leucoanthocyanidins. In this study we describe cloning and expression of the genes encoding the flavonoid-biosynthetic enzyme DFR in Gypsophila paniculata L. Inspection of the 1279 bp long sequence revealed an open reading frame 1063 bp, including a 36 bp 5' leader region and 181 bp 3' untranslated region. Comparison of the coding region of this DFR cDNA sequence including the sequences of Arabidopsis thaliana, Citrus sinensis, Dianthus caryophyllus, Ipomoea batatas, Matthiola incana, Nierembergia sp, Petunia hybrida, Solanum tuberosum, Vitis vinifera reveals an identity higher than 69% at the nucleotide level. The function of this nucleotide sequences was verified by comparison with amino acid sequences of the amino-terminus and tryptic peptides from purified plant enzyme, by northern blotting with mRNA from wild type and mutant plants, by in vitro expression yielding and enzymatically active reductase, as indicated by the small leucopelargonidin peak. Genomic southern blot analysis showed the presence of only one gene for DFR in Gypsophila paniculata.