• Natural Product Sciences
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• v.11 no.3
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• pp.136-138
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• 2005

Bioassay-guided fractionation of an organic extract of the broth from the marine-derived fungus of the genus Aspergillus led to the isolation of the polyketides, (+)-epoxydon (1), (+)-epoxydon monoacetate (2), gentisyl alcohol (3), 3-chlorogentisyl alcohol (4), and methylhydroquinone (5). Compounds 1-5 showed a potent antibacterial activity against the methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA) with MIC (minimum inhibitory concentration) values of 12.5, 12.5, 12.5, 50.0, and $6.2\;{\mu}g/mL$, respectively. Compounds 1-4 also exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with $IC_{50}$ values of 6.0, 15.0, 7.0, and $1.0\;{\mu}M$, respectively.

• Korean Journal of Pharmacognosy
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• v.48 no.1
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• pp.1-4
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• 2017

Four polyketides, tyrosol (1), (3R,4R)-(-)-4-hydroxymellein (2), (3R,4S)-(-)-4-hydroxymellein (3), and 1-phenyl-1,2-ethanediol (4) were isolated from organic extracts of cultures of an endophytic fungus Arthrinium sp. (JS420) isolated from stem of a halophyte Suaeda japonica Makico. Chemical structures of the isolated compounds were elucidated by comparison of their spectral data such as NMR and ESIMS with reported literature values. Among the isolated compounds, 3 and 4 were isolated for the first time from this fungus.

• Natural Product Sciences
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• v.26 no.1
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• pp.10-27
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• 2020

Endophytes are defined as microorganisms that spend part of lifetime interior of plant tissues without causing negative effects. They have been used for agricultural purpose, biofuel production, bioremediation, medication, etc. In particular, endophytes have been emerged as a good source for bioactive secondary metabolites. A large number of secondary metabolites are currently being reported. In this report, we focus on the secondary metabolites that were originated from endophytic fungi inhabiting medicinal plants. They were classified into several groups such as nitrogenous compounds, steroids, sulfide-containing metabolites, terpenoids, polyketides, and miscellaneous for discussion of chemical structures and biological activities.

• Bulletin of the Korean Chemical Society
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• v.31 no.6
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• pp.1695-1698
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• 2010

Protulactones A (1) and B (2), two new polyketide-derived fungal metabolites, have been isolated from an EtOAc extract of the marine-derived fungus Aspergillus sp. SF-5044 by various chromatographic methods. The structures of 1 and 2 were mainly determined by analysis of the NMR spectroscopic data and MS data, along with chemical methods such as Mosher method. Protulactones A (1) and B (2) are new members of polyketide-derived secondary metabolites, possessing unique ring systems among the fungal metabolites produced by the genus Aspergillus.

• Bulletin of the Korean Chemical Society
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• v.28 no.6
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• pp.990-994
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• 2007

Bioassay-guided fractionation of the MeOH extract from the sponge Discodermia calyx collected off the coast of Jeju Island, South Korea, led to the isolation of a polyketide, icadamide C (1), along with previously reported theopederin K (3). Structure elucidation was performed by a combination of high resolution mass and 2D-NMR (principally COSY, HMBC, HSQC, and NOESY) spectroscopy. Stereochemistry of compound 1 was determined as 2R*, 3R*, 6R*, 10S*, 11S*, 12R*, 13S*, 15R* and 2'S by NMR data and Marfey analysis. Isolated metabolites displayed potent cytotoxic activity against a small panel of five human solid tumor cell lines with ED50 values of less than 0.1 μg/mL.

• Journal of Microbiology and Biotechnology
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• v.16 no.4
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• pp.637-638
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• 2006

Bioassay-guided fractionation of an organic extract of the culture broth from an unidentified marine-derived fungus led to the isolation of a new metabolite, N-[2-(4-hydroxyphenyl) acetyl]formamide (1), along with four known polyketides, 4-hydroxyphenyl acetamide (2), 4-hydroxyphenyl acetic acid (3), 3,4-dihydroxyphenyl acetic acid (4), and N-[2-(4-hydroxyphenyl)ethenyl]formamide (5). The structures of 1-5 were elucidated by spectral data analyses. Among them, compounds 1, 4, and 5 exhibited significant radical scavenging activity against 1, 1-diphenyl-2-picrylhydrazyl (DPPH) with $IC_{50}$ values of 8.4, 11.9, and $0.2{\mu}M$, respectively.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2019.04a
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• pp.34-34
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• 2019

About 60% of the present drugs were developed from natural products with unique chemical diversity and biological activities. Hence, discovery of new bioactive compounds from natural products is still important for the drug development. On the other hand, breakthrough made in synthetic biology has also begun to supply us with many useful compounds through manipulation of biosynthetic gene for secondary metabolites. Theoretically, this approach can also be exploited to generate new unnatural compounds by intermixing genes from different biosynthetic pathway. Considering the potential, we are studying about bioactive compounds in natural sources, as well as the biosynthesis of natural products including engineering of the secondary metabolite enzymes to make new compounds in order to construct the methodological basis of the synthetic biology. In this symposium, engineering of secondary metabolite enzymes that are involved in the biosynthesis of plant polyketides to generate new compounds in our laboratory will be mainly introduced.

• Mycobiology
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• v.42 no.1
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• pp.34-40
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• 2014

Usnea longissima has a long history of use as a traditional medicine. Several bioactive compounds, primarily belonging to the polyketide family, have been isolated from U. longissima. However, the genes for the biosynthesis of these compounds are yet to be identified. In the present study, three different types of non-reducing polyketide synthases (UlPKS2, UlPKS4, and UlPKS6) were identified from a cultured lichen-forming fungus of U. longissima. Phylogenetic analysis of product template domains showed that UlPKS2 and UlPKS4 belong to group IV, which includes the non-reducing polyketide synthases with an methyltransferase (MeT) domain that are involved in methylorcinol-based compound synthesis; UlPKS6 was found to belong to group I, which includes the non-reducing polyketide synthases that synthesize single aromatic ring polyketides, such as orsellinic acid. Reverse transcriptase-PCR analysis demonstrated that UlPKS2 and UlPKS4 were upregulated by sucrose; UlPKS6 was downregulated by asparagine, glycine, and alanine.

• Journal of Microbiology and Biotechnology
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• v.16 no.1
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• pp.153-157
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• 2006

A soil metagenomic library was constructed using an E. coli-fosmid cloning system with environmental DNAs extracted from Kwangreung forest topsoil. We targeted the genes involved in the biosynthesis of bacterial polyketides. Initially, a total of 36 clone pools (10,800 clones) were explored by the PCR-based method using the metagenomic DNAs from each pool and a degenerate primer set, which has been designed based on the highly conserved regions among ketoacyl synthase (KS) domains in actinomycete type I polyketide synthases (PKS Is). Six clone pools were tentatively selected as positive and further examined through a hybridization-based method for selecting a fosmid clone containing PKS I genes. Colony hybridization was performed against fosmid clones from the 6 positive pools, and finally 4 clones were picked out and confirmed to contain the conserved DNA fragment of KS domains. In this study, we present a simple and feasible sorting method for a desired clone from metagenomic libraries.

• Journal of Microbiology and Biotechnology
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• v.25 no.10
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• pp.1648-1652
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• 2015

Azaphilone polyketides are synthesized by iterative non-reducing fungal polyketide synthases (NR-fPKSs) with a C-terminus reductive domain (-R). Several azaphilone biosynthetic gene clusters contain a putative serine hydrolase gene; the Monascus azaphilone pigment (MAzP) gene cluster harbors mppD. The MAzP productivity was significantly reduced by a knockout of mppD, and the MAzP NR-fPKS-R gene (MpPKS5) generated its product in yeast only when co-expressed with mppD. Site-directed mutations of mppD for conserved Ser/Asp/His residues abolished the product formation from the MpPKS5/mppD co-expression. MppD and its homologs are thus proposed as a new protein factor involved in the product formation of NR-fPKS-R.