• Title/Summary/Keyword: C-C bond formation

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Formation of Cyclodextrin Adsorbent Using Fatty Acid as a Ligand and Fractionation of $\alpha$-, $\beta$- and ${\gamma}$-cyclodextrins (Fatty Acid를 Ligand로한 Cyclodextrin Adsorbent의 제조와 $\alpha$-, $\beta$-, ${\gamma}$-Cyclodextrin의 분획)

  • 정승환;박동찬이용현
    • KSBB Journal
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    • v.10 no.5
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    • pp.491-498
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    • 1995
  • In order to fraclionate ${\alpha}$-, ${\beta}$- and ${\gamma}$-cyclodextrins(CDs) from CD reaction mixture, various CD adsorbents were manufactured using fatty acids as the ligand molecules and anion exchange resins as matrix. Among several anion exchange resins, DEAE Cellulose was found to be the most suitable matrix for binding fatty acid. The binding stability between DEAE Cellulose and capric acid was tested under the various operation conditions, such as temperature, ethanol concentration, and ionic strength. Specific CD adsorbents manufactured with different chain-length fatty acids, saturated and unsaturated, were compared in terms of the recovery yield and selectivity of ${\alpha}$-, ${\beta}$- and ${\gamma}$-CDs. Stearic acid (C18, saturated) was identified as the most effective ligand for fractionation of ${\alpha}$-CD, and linoleic acid ((C18, unsaturated ) for ${\beta}$-CD. The spacer length between the matrix and ligand was required for effective adsorption of CDs, and the double bond in fatty acid molecules was also acted as an important factor determining recovery yield and selectivity. The elusion patterns of ${\alpha}$- and ${\alpha}$-, ${\beta}$-CD from column packed with stearic acid and linoleic acid CD adsorbents were also investigated at the various elusion conditions for fractionation of ${\alpha}$- and ${\beta}$-CD.

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Durability of GFRP Rebar with Ribs Containing Milled Alkaline Resistant Glass Fibers (알카리저항 초단유리섬유를 리브에 사용한 유리섬유 보강근의 내구성능)

  • Moon, Do Young;Oh, Hong Seob
    • Journal of the Korea institute for structural maintenance and inspection
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    • v.15 no.1
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    • pp.281-287
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    • 2011
  • GFRP rebars could be deteriorated by concrete alkalinity. This paper focuses on the investigation of durability of GFRP rebars with ribs exposed to alkaline environment of concrete. It has been reported that the milled E-glass fibers in the ribs of GFRP rebar can increase bond strength between GFRP rebars and the concrete. In this study, the effect of milled alkaline resistant glass fibers (milled AR glass) and milled E-glass in the ribs on the durability of GFRP rebar is investigated through ISS tests and moist absorption tests of the bare rebar. To accelerate the effect of the alkalinity, high temperature($40^{\circ}C$) was applied. According to the test results, mix ratio of milled glass fibers in the ribs by weight had significant effect on durability of GFRP rebars with ribs. It is because that the high mix ratio may leads more voids in the ribs due to lower workability and formability. On the other hand, changing fiber type in the ribs from E-glass to AR-glass had no improvements on ISS strength of the GFRP rebar. Therefore, it is found that determination of proper mix ratio of milled glass fiber in the mixture for the formation of the ribs of the GFRP rebar is important.

Water-Soluble Conjugated Polymer and Graphene Oxide Composite Used as an Efficient Hole-Transporting Layer for Organic Solar Cells (수용성 공액고분자/그래핀 옥사이드 복합체를 이용한 유기태양전지의 정공수송층에 대한 연구)

  • Kim, Kyu-Ri;Oh, Seung-Hwan;Kim, Hyun Bin;Jeun, Joon-Pyo;Kang, Phil-Huyn
    • Polymer(Korea)
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    • v.38 no.1
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    • pp.38-42
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    • 2014
  • The poly[(9,9-bis((6'-(N,N,N-trimethylammonium)hexyl)-2,7-fluorene)-alt-(9,9-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-9-fluorene)) dibromide (WPF-6-oxy-F)] and graphene oxide (GO) was blended and irradiated with gamma ray under ambient condition. This WPF-6-oxy-F-GO composite was investigated as a hole-transporting layer (HTL) in organic solar cells (OSCs). Compared with the pristine GO, the sheet resistance ($R_{sheet}$) of irradiated WPF-6-oxy-F-GO was decreased about 2 orders of magnitude. The reason for the decrease of $R_{sheet}$ is the effect of efficient ${\pi}-{\pi}$ packing resulted from the formation of C-N bond between WPF6-oxy-F and GO. As a result, the efficiency of OSCs was dramatically enhanced ~ 6.10% by introducing irradiated WPF-6-oxy-F-GO as a HTL. WPF-6-oxy-F-GO is a sufficient candidate for HTL to facilitate the low-cost and high efficiency OSCs.

Evolutionary Explanation for Beauveria bassiana Being a Potent Biological Control Agent Against Agricultural Pests

  • Han, Jae-Gu
    • 한국균학회소식:학술대회논문집
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    • 2014.05a
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    • pp.27-28
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    • 2014
  • Beauveria bassiana (Cordycipitaceae, Hypocreales, Ascomycota) is an anamorphic fungus having a potential to be used as a biological control agent because it parasitizes a wide range of arthropod hosts including termites, aphids, beetles and many other insects. A number of bioactive secondary metabolites (SMs) have been isolated from B. bassiana and functionally verified. Among them, beauvericin and bassianolide are cyclic depsipeptides with antibiotic and insecticidal effects belonging to the enniatin family. Non-ribosomal peptide synthetases (NRPSs) play a crucial role in the synthesis of these secondary metabolites. NRPSs are modularly organized multienzyme complexes in which each module is responsible for the elongation of proteinogenic and non-protein amino acids, as well as carboxyl and hydroxyacids. A minimum of three domains are necessary for one NRPS elongation module: an adenylation (A) domain for substrate recognition and activation; a tholation (T) domain that tethers the growing peptide chain and the incoming aminoacyl unit; and a condensation (C) domain to catalyze peptide bond formation. Some of the optional domains include epimerization (E), heterocyclization (Cy) and oxidation (Ox) domains, which may modify the enzyme-bound precursors or intermediates. In the present study, we analyzed genomes of B. bassiana and its allied species in Hypocreales to verify the distribution of NRPS-encoding genes involving biosynthesis of beauvericin and bassianolide, and to unveil the evolutionary processes of the gene clusters. Initially, we retrieved completely or partially assembled genomic sequences of fungal species belonging to Hypocreales from public databases. SM biosynthesizing genes were predicted from the selected genomes using antiSMASH program. Adenylation (A) domains were extracted from the predicted NRPS, NRPS-like and NRPS-PKS hybrid genes, and used them to construct a phylogenetic tree. Based on the preliminary results of SM biosynthetic gene prediction in B. bassiana, we analyzed the conserved gene orders of beauvericin and bassianolide biosynthetic gene clusters among the hypocrealean fungi. Reciprocal best blast hit (RBH) approach was performed to identify the regions orthologous to the biosynthetic gene cluster in the selected fungal genomes. A clear recombination pattern was recognized in the inferred A-domain tree in which A-domains in the 1st and 2nd modules of beauvericin and bassianolide synthetases were grouped in CYCLO and EAS clades, respectively, suggesting that two modules of each synthetase have evolved independently. In addition, inferred topologies were congruent with the species phylogeny of Cordycipitaceae, indicating that the gene fusion event have occurred before the species divergence. Beauvericin and bassianolide synthetases turned out to possess identical domain organization as C-A-T-C-A-NM-T-T-C. We also predicted precursors of beauvericin and bassianolide synthetases based on the extracted signature residues in A-domain core motifs. The result showed that the A-domains in the 1st module of both synthetases select D-2-hydroxyisovalerate (D-Hiv), while A-domains in the 2nd modules specifically activate L-phenylalanine (Phe) in beauvericin synthetase and leucine (Leu) in bassianolide synthetase. antiSMASH ver. 2.0 predicted 15 genes in the beauvericin biosynthetic gene cluster of the B. bassiana genome dispersed across a total length of approximately 50kb. The beauvericin biosynthetic gene cluster contains beauvericin synthetase as well as kivr gene encoding NADPH-dependent ketoisovalerate reductase which is necessary to convert 2-ketoisovalarate to D-Hiv and a gene encoding a putative Gal4-like transcriptional regulator. Our syntenic comparison showed that species in Cordycipitaceae have almost conserved beauvericin biosynthetic gene cluster although the gene order and direction were sometimes variable. It is intriguing that there is no region orthologous to beauvericin synthetase gene in Cordyceps militaris genome. It is likely that beauvericin synthetase was present in common ancestor of Cordycipitaceae but selective gene loss has occurred in several species including C. militaris. Putative bassianolide biosynthetic gene cluster consisted of 16 genes including bassianolide synthetase, cytochrome P450 monooxygenase, and putative Gal4-like transcriptional regulator genes. Our synteny analysis found that only B. bassiana possessed a bassianolide synthetase gene among the studied fungi. This result is consistent with the groupings in A-domain tree in which bassianolide synthetase gene found in B. bassiana was not grouped with NRPS genes predicted in other species. We hypothesized that bassianolide biosynthesizing cluster genes in B. bassiana are possibly acquired by horizontal gene transfer (HGT) from distantly related fungi. The present study showed that B. bassiana is the only species capable of producing both beauvericin and bassianolide. This property led to B. bassiana infect multiple hosts and to be a potential biological control agent against agricultural pests.

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Are Bound Residues a Solution for Soil Decontamination\ulcorner

  • Bollag, Jean-Marc
    • Proceedings of the Korean Society of Soil and Groundwater Environment Conference
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    • 2003.10a
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    • pp.111-124
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    • 2003
  • Processes that cause immobilization of contaminants in soil are of great environmental importance because they may lead to a considerable reduction in the bioavailability of contaminants and they may restrict their leaching into groundwater. Previous investigations demonstrated that pollutants can be bound to soil constituents by either chemical or physical interactions. From an environmental point of view, chemical interactions are preferred, because they frequently lead to the formation of strong covalent bonds that are difficult to disrupt by microbial activity or chemical treatments. Humic substances resulting from lignin decomposition appear to be the major binding ligands involved in the incorporation of contaminants into the soil matrix through stable chemical linkages. Chemical bonds may be formed through oxidative coupling reactions catalyzed either biologically by polyphenol oxidases and peroxidases, or abiotically by certain clays and metal oxides. These naturally occurring processes are believed to result in the detoxification of contaminants. While indigenous enzymes are usually not likely to provide satisfactory decontamination of polluted sites, amending soil with enzymes derived from specific microbial cultures or plant materials may enhance incorporation processes. The catalytic effect of enzymes was evaluated by determining the extent of contaminants binding to humic material, and - whenever possible - by structural analyses of the resulting complexes. Previous research on xenobiotic immobilization was mostly based on the application of $^{14}$ C-labeled contaminants and radiocounting. Several recent studies demonstrated, however, that the evaluation of binding can be better achieved by applying $^{13}$ C-, $^{15}$ N- or $^{19}$ F-labeled xenobiotics in combination with $^{13}$ C-, $^{15}$ N- or $^{19}$ F-NMR spectroscopy. The rationale behind the NMR approach was that any binding-related modification in the initial arrangement of the labeled atoms automatically induced changes in the position of the corresponding signals in the NMR spectra. The delocalization of the signals exhibited a high degree of specificity, indicating whether or not covalent binding had occurred and, if so, what type of covalent bond had been formed. The results obtained confirmed the view that binding of contaminants to soil organic matter has important environmental consequences. In particular, now it is more evident than ever that as a result of binding, (a) the amount of contaminants available to interact with the biota is reduced; (b) the complexed products are less toxic than their parent compounds; and (c) groundwater pollution is reduced because of restricted contaminant mobility.

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Study on the soluble exoression of recombinant human eoidermal growth factor using various fusion oartners in Escherichia coli (재조합 대장균에서 다양한 융합 파트너를 이용한 인간 상피세포성장인자의 발현 연구)

  • Kim, Byung-Lip;Baek, Jung-Eun;Kim, Chun-Sug;Lee, Hyeok-Weon;Ahn, Jung-Oh;Lee, Hong-Weon;Jung, Joon-Ki;Lee, Eun-Gyo;Kim, In-Ho
    • KSBB Journal
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    • v.23 no.3
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    • pp.205-212
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    • 2008
  • The efficient soluble expression of human epidermal growth factor (hEGF) was achieved by using functional fusion partners in cytoplasm and periplasm of Escherichia coli (E. coli). hEGF was over-expressed in inactive inclusion body form in cytoplasm of E. coli due to improper disulfide bond formation and hydrophobic interaction, yielding about 5.9 mg/L in flask culture. Six functional fusion partners were introduced by linking to N-terminal part of hEGF gene for the high-level expression of soluble and active hEGF in cytoplasm and peri plasm region. Three fusion partners for cytoplasmic expression such as acidic tail of synuclein (ATS), thioredoxin (Trx) and lipase, and three fusion partners for periplasmic expression such as periplasmic cystein oxidoreductases (DsbA and DsbC) and maltose binding protein (MBP) were investigated. hEGF fused with ATS and DsbA showed over 90% of solubility in cytoplasm and periplasm, respectively. Especially DsbA was found to be an efficient fusion partner for soluble and high-level expression of hEGF, yielding about 18.1 mg/L and three-fold higher level compared to that of insoluble non-fusion hEGF in cytoplasm. Thus, heterologous proteins containing complex disulfide bond and many hydrophobic amino acids can effectively be produced as an active form in E. coli by introducing a suitable peptide or protein.

Construction of Candida antarctica Lipase B Expression System in E. coli Coexpressing Chaperones (대장균에서의 Chaperone 동시 발현을 통한 Candida antarctica Lipase B 발현 시스템 구축)

  • Jung, Sang-Min;Lim, Ae-Kyung;Park, Kyung-Moon
    • KSBB Journal
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    • v.23 no.5
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    • pp.403-407
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    • 2008
  • Recently, Candida antarctica lipase B (CalB) draws attention from industries for various applications for food, detergent, fine chemical, and biodiesel, because of its characteristics as an efficient biocatalyst. Since many industrial processes carry out in organic solvent and at high temperature, CalB, which is stable under harsh condition, is in demand from many industries. In order to reform CalB promptly, the expression system which has advantages of ease to use and low cost for gene libraries screening was developed using E. coli. The E. coli strains, Rosettagami with competence for enhanced disulfide bond formation, Novablue, and $DH5{\alpha}$, were exploited in this study. To obtain the soluble CalB, the pCold I vector expressing the cloned gene at $15^{\circ}C$ and the chaperone plasmids containing groES/groEL, groES/groEL/tig, tig, dnaK/dnaJ/grpE, and dnaK/dnaJ/grpE/groES/groEL were used for coexpression of CalB and chaperones. The colonies expressing functional lipase were selected by employing the halo plate containing 1% tributyrin, and the CalB expression was confirmed by SDS-PAGE. E. coli Rosettagami and $DH5{\alpha}$ harbouring groES/groEL chaperones were able to express soluble CalB effectively. From a facilitative point of view, E. coli $DH5{\alpha}$ is more suitable for further mutation study.

Control of Graphene's Electrical Properties by Chemical Doping Methods

  • Lee, Seung-Hwan;Choi, Min-Sup;La, Chang-Ho;Yoo, Won-Jong
    • Proceedings of the Korean Vacuum Society Conference
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    • 2011.08a
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    • pp.119-119
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    • 2011
  • This study examined the synthesis of large area graphene and the change of its characteristics depending on the ratio of CH4/H2 by using the thermal CVD methods and performed the experiments to control the electron-hole conduction and Dirac-point of graphene by using chemical doping methods. Firstly, with regard to the characteristics of the large area graphene depending on the ratio of CH4/H2, hydrophobic characteristics of the graphene changed to hydrophilic characteristics as the ratio of CH4/H2 reduces. The angle of contact also increased to 78$^{\circ}$ from 58$^{\circ}$. According to the results of Raman spectroscopy showing the degree of defect, the ratio of I(D)/I(G) increases to 0.42% from 0.25% and the surface resistance also increased to 950 ${\Omega}$ from 750 ${\Omega}$/sq. As for the graphene synthesis at the high temperature of 1,000$^{\circ}$ by using CH4/H2 in a Cu-Foil, the possibility of graphene formation was determined as a function of the ratio of H2 included in the fixed quantity of CH4 as per specifications of every equipment. It was observed that the excessive amount of H2 prevented graphene from forming, as extra H-atoms and molecules activated the reaction to C-bond of graphene. Secondly, in the experiment for the electron-hole conduction and the Dirac-point of graphene using the chemical doping method, the shift of Dirac-point and the change in the electron-hole conduction were observed for both the N-type (PEI) and the P-type (Diazonium) dopings. The ID-VG results show that, for the N-type (PEI) doped graphene, Dirac-point shifted to the left (-voltage direction) by 90V at an hour and by 130 V at 2 hours respectively, compared to the pristine graphene. Carrier mobility was also reduced by 1,600 cm2/Vs (1 hour) and 1,100 cm2/Vs (2 hours), compared to the maximum hole mobility of the pristine graphene.

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Kinetic Studies on the Reaction of 4-Substituted-2,6-dinitrochlorobenzenes with Substituted Anilines in MeOH-MeCN Mixtures (MeOH-MeCN 혼합용매계에서 4-치환-2,6-이니트로 염화벤젠과 아닐린 치환체와의 반응에 대한 속도론적 연구)

  • Dae-Ho Kang;In-Sun Koo;Jong Gun Lee;Ikchoon Lee
    • Journal of the Korean Chemical Society
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    • v.29 no.6
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    • pp.565-574
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    • 1985
  • The rates of reaction between 4-substituted-2,6-dinitrochlorobenzenes with para-substituted anilines in methanol-acetonitrile mixtures were measured by conductometry. It was observed that the rate constant increases in the order of X = 4-$NO_2 {\gg}4-CN {\gg}4- CF_3$, where X is a substituent in the substrate. The rate constant also increases in the order of Y = p-O$CH_3{\gg}p- CH_3{\gg}H {\gg}p-Cl{\gg}m- NO_2$, where Y is a substituent in the aniline ring. Kinetic studies in the methanol-acetonitrile solvent system with various nucleophiles showed that the N-C bond forming step is making a great contribution to the overall second order rate constant. The electrophilic catalysis by methanol probably consists of the hydrogen bonding between alcoholic hydrogen and leaving chloride in the transition state. The nucleophilic catalysis by methanol may be ascribed to the formation of hydrogen bonds between alcoholic oxygen and hydrogens of amines in the transition state. All these experimental facts are supporting the operation of $S_N$Ar machanism with the second step being the rate determining. This mechanism can be successfully fitted to the PES model.

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Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 2016.05a
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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