• 제목/요약/키워드: secondary metabolites compounds

검색결과 171건 처리시간 0.024초

영지버섯(Ganoderma lucidum)으로 부터 분리한 이차대사산물 및 이들의 항 염증 활성 (Secondary Metabolites Isolated from Ganoderma lucidum and Their Anti-inflammatory Activity)

  • 김혜지;구만형;이준혁;서승석;윤의중
    • 생약학회지
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    • 제50권3호
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    • pp.232-238
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    • 2019
  • Phytochemical study of Ganoderma lucidum (Polyporaceae) let to the isolation of five lanostane triterpenoid (1-5), along with two nitrogen derived phenolic compounds, N-phenylethylformamide (6) and N-acetylphenethylamine (7). The structures of the compounds were determined by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with published values. Compounds 6 and 7 were isolated for the first time from the genus Ganoderma and this species. All the compounds were evaluated for cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in mouse macrophage RAW 264.7 cells in vitro. Among the isolates, compounds 2 and 3 showed moderate inhibitory activity against NO production.

Secondary Metabolite Profiling in Various Parts of Tomato Plants

  • Kim, Dong Sub;Na, Haeyoung;Kwack, Yurina;Chun, Changhoo
    • 원예과학기술지
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    • 제32권2호
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    • pp.252-260
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    • 2014
  • Contents of carotenoids, phenolic compounds, volatile organic compounds, and alkaloids in leaves, internodes, fruits, and roots of tomatoes in different developmental stages were measured. Lycopene, ${\beta}$-carotene, and lutein were detected in all the tested parts except roots and green fruits. Lycopene content in red fruits was $49.04{\mu}g{\cdot}g^{-1}$ FW, while that in the other parts was below $40{\mu}g{\cdot}g^{-1}$ FW. ${\beta}$-Carotene and lutein contents in 24th leaves were 5.81 and $6.40{\mu}g{\cdot}g^{-1}$ FW, respectively, and were greater than those in the other parts. Caffeic, chlorogenic, and vanillic acids were detected in all the tested parts except roots. The content of chlorogenic acid in the 18th leaves was $40.11{\mu}g{\cdot}g^{-1}$ FW, while that in the other parts was lower than $31.00{\mu}g{\cdot}g^{-1}$ FW. The contents of caffeic and vanillic acids in the 24th leaves were 9.18 and $1.64{\mu}g{\cdot}g^{-1}$ FW, respectively, and were greater than those in the other parts. Moreover, younger leaves contained the more diverse volatile organic compounds including monoterpenes and sesquiterpenes. Contents of dehydro-tomatine and ${\alpha}$-tomatine were greatest in leaves, followed by internodes, roots and fruits. Younger leaves and internodes contained more dehydro-tomatine and ${\alpha}$-tomatine than older leaves and internodes. The contents of dehydro-tomatine and ${\alpha}$-tomatine in the 24th leaves were 0.89 and $1.42mg{\cdot}g^{-1}$ FW, respectively, and were greatest among all the tested parts. Our results indicated that, except lycopene, tomato leaves included greater secondary metabolites contents than red fruits. The results suggest that inedible parts of tomato plants can be used as raw material for antioxidants, anti-inflammatory agents, fungistats, and pesticides.

Heterologous Expression of Novel Cytochrome P450 Hydroxylase Genes from Sebekia benihana

  • Park Nam-Sil;Park Hyun-Joo;Han Kyu-Boem;Kim Eung-Soo
    • Journal of Microbiology and Biotechnology
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    • 제16권2호
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    • pp.295-298
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    • 2006
  • Actinomycetes are ubiquitous Gram-positive soil bacteria and a group of the most important industrial microorganisms for the biosynthesis of many valuable secondary metabolites as well as the source of various bioconversion enzymes. Cytochrome P450 hydroxylase (CYP), a hemebinding protein, is known to be involved in the modification of various natural compounds, including polyketides, fatty acids, steroids, and some aromatic compounds. Previously, six different novel CYP genes were isolated from a rare actinomycetes called Sebekia benihana, and they were completely sequenced, revealing significant amino acid similarities to previously known CYP genes involved in Streptomyces secondary metabolism. In the present study, these six CYP genes were functionally expressed in Streptomyces lividans, using an $ermE^{*}$ promoter-containing Streptomyces expression vector. Among six CYP genes, two S. benihana CYP genes (CYP503 and CYP504) showed strong hydroxylation activities toward 7-ethoxycoumarin. Furthermore, the recombinant S. lividans containing both the S. benihana CYP506-ferredoxin genes as well as the S. coelicolor feredoxin reductase gene also demonstrated cyclosporin A hydroxylation activity, suggesting potential application of actinomycetes CYPs for the biocatalysts of natural product bioconversion.

LC/MS/MS를 이용한 어린이 소변 중 프탈레이트 대사산물 분석 (Determination of Phthalate Metabolites in Korean Children's Urine by High Performance Liquid Chromatography with Triple Quadrupole Tandem Mass Spectrometry)

  • 고영림;정지연;최경호;김판기
    • 한국환경보건학회지
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    • 제34권4호
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    • pp.271-278
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    • 2008
  • Dialkylated phthalates have been commonly used as plasticizers and a variety of applications. Phthalate diesters have been shown to be developmental and reproductive toxicants. It is very difficult to exactly estimate the dose of dialkylated phthalates taken up by the general population because of environmental contamination. Urinary metabolites of phthalates enabled to estimate internal exposure. The objective of this study was quantitative determination of phthalate metabolites by LC/MS/MS with on-line cleanup method to analyze phthalate metabolites in Korean children's urine. We employed LC/MS/MS with on-line enrichment and column-switching techniques for this biological monitoring. Metabolites determined were 4 primary metabolites; MEHP, MnBP, MiBP, MEP and 2 secondary metabolites of DEHP; 5-OH-MEHP), 5-oxo-MEHP. We analyzed children's urine from 30 boys and 30 girls. The method detection limit of phthalate metabolites were 0.03 ng/mL for MEP, 1.05 ng/mL for MBP, 0.22 ng/mL for MEHP, 0.15 ng/mL for 5-OHMEHP and 0.16 ng/mL for 5-oxo-MEHP, respectively. Switching Column LC/MS/MS was proven to be a useful tool to determine metabolites of phthalate diesters in human urine. The correlation among phthalate metabolites was very high and statistically significant, except MEP. The children's age (months) was negatively correlated to the concentration of phthalate metabolites. The geometric mean concentration of phthalate metabolites (mg/g creatinine) in children's urine were 25.5 for MEP, 130.3 for MnBP, 56.8 for MiBP, 19.5 for MEHP, 85.6 for 5-OH-MEHP and 83.1 for 5-oxo-MEHP, respectively. Levels of estimated daily intake of parent phthalate compounds (${\mu}g$/kg bw/day) were 0.8 for DEP, 5.0 for DnBP, 1.9 for DiBP and $8.9{\sim}14.2$ for DEHP, respectively. Estimated daily intake for DEP and DiBP were lower than those of other studies but the value for DEHP was higher than that of other study.

칠면초 유래 내생균(Arthrinium sp. JS420)이 생산하는 이차대사산물 규명 (Secondary Metabolites Produced by an Endophytic Fungus Arthrinium sp. JS420 of Halophytic Plant Suaeda japonica)

  • 최현규;심상희
    • 생약학회지
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    • 제48권1호
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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.

Polyketide 이차대사물질의 생합성 (Biosynthesis of Polyketide Secondary Metabolites)

  • 윤여준;송재경
    • 생명과학회지
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    • 제12권5호
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    • pp.632-648
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    • 2002
  • The term polyketide defines a class of natural products synthesized through the successive condensation of small arboxylic acids, which results in products containing multiple carbonyl or hydroxyl groups, each separated by one arbon atom, as in the structural element CH$_2$C(=0)CH$_2$CH(OE)CH$_2$C(=0)-. Plant flavonoids, fungal aflatoxins, as well as undreds of compounds of different structures that can inhibit the growth of bacteria, viruses, fungi, parasites or human umor cells are included in this diverse group. Some of antifungal polyketides also have immunosuppresive activity. olyketides can vary widely in structure, and the diversity of polyketide structures reflects the wide variety of their iological properties. This review focuses on the biosynthesis of polyketides and recent progress in combinatorial iosynthesis of new hybrid polyketide compounds.

Methyl jasmonate 처리에 의한 인삼 (Panax ginseng C.A. Meyer) 부정근의 이차대사산물 및 항산화활성 증가 (Increasement of Secondary Metabolites and Antioxidative Activity in Panax ginseng Adventitious Root by Methyl Jasmonate)

  • 임순;배기화;신차균;김윤영;김윤수
    • Journal of Plant Biotechnology
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    • 제32권3호
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    • pp.225-231
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    • 2005
  • 인삼부정근 배양에서 MeJA 처리가 부정근내 진세노사이드와 페놀화합물의 생산에 미치는 영향과 이러한 이차대사 산물의 증가에 따른 인삼부정근의 항산화활성의 효과를 조사하였다. 다양한 농도의 MeJA를 인삼부정근에 처리한 결과, $100\;{\mu}M$ MeJA에서 부정근내 진세노사이드의 생산은 26.6 mg/g dry wt로 대조구보다 약 8배 이상 생산하는 것으로 나타났다. 하지만, MeJA의 처리는 부정근의 생장을 감소시키는 것으로 나타났다. 페놀화합물의 생산 역시 MeJA처리에 의하여 증가되는 경향을 나타냈으며 $50\;{\mu}M$ MeJA에서 0.38 mg/g dry wt로 대조구에 비하여 약 3배 이상 증가한 것으로 나타났다. 이러한 MeJA의 처리효과는 조건배지 (CM)를 이용하는 것이 신선배지 (FM)를 이용하는 것보다 유리한 것으로 나타났다. 배지성분이 결핍된 조건배지에서의 진세노사이드 생산은 신선배지에서 보다 약 1.7배가 증가한 것으로 나타났으며, 페놀화합물 역시 조건배지에서약 1.2배가 증가한 것으로 나타났다. 이러한 MeJA 처리에 의한 진세노사이드와 페놀화합물의 증가는 결과적으로 인삼부정근의 항상화활성을 무처리구인 대조구에 비해서 약 72%이상 증가시키는 것으로 나타났다.

Isolation, Purification, and Characterization of Five Active Diketopiperazine Derivatives from Endophytic Streptomyces SUK 25 with Antimicrobial and Cytotoxic Activities

  • Alshaibani, Muhanna M.;MohamadZin, Noraziah;Jalil, Juriyati;Sidik, Nik Marzuki;Ahmad, Siti Junaidah;Kamal, Nurkhalida;Edrada-Ebel, RuAngelie
    • Journal of Microbiology and Biotechnology
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    • 제27권7호
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    • pp.1249-1256
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    • 2017
  • In our search for new sources of bioactive secondary metabolites from Streptomyces sp., the ethyl acetate extracts from endophytic Streptomyces SUK 25 afforded five active diketopiperazine (DKP) compounds. The aim of this study was to characterize the bioactive compounds isolated from endophytic Streptomyces SUK 25 and evaluate their bioactivity against multiple drug resistance (MDR) bacteria such as Enterococcus raffinosus, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumanii, Pseudomonas aeruginosa, and Enterobacter spp., and their cytotoxic activities against the human hepatoma (HepaRG) cell line. The production of secondary metabolites by this strain was optimized through Thornton's medium. Isolation, purification, and identification of the bioactive compounds were carried out using high-performance liquid chromatography, high-resolution mass liquid chromatography-mass spectrometry, Fourier transform infrared spectroscopy, and nuclear magnetic resonance, and cryopreserved HepaRG cells were selected to test the cytotoxicity. The results showed that endophytic Streptomyces SUK 25 produces four active DKP compounds and an acetamide derivative, which were elucidated as $cyclo-({\text\tiny{L}}-Val-{\text\tiny{L}}-Pro)$, $cyclo-({\text\tiny{L}}-Leu-{\text\tiny{L}}-Pro)$, $cyclo-({\text\tiny{L}}-Phe-{\text\tiny{L}}-Pro)$, $cyclo-({\text\tiny{L}}-Val-{\text\tiny{L}}-Phe)$, and N-(7-hydroxy-6-methyl-octyl)-acetamide. These active compounds exhibited activity against methicillin-resistant S. aureus ATCC 43300 and Enterococcus raffinosus, with low toxicity against human hepatoma HepaRG cells. Endophytic Streptomyces SUK 25 has the ability to produce DKP derivatives biologically active against some MDR bacteria with relatively low toxicity against HepaRG cells line.

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 한국균학회 2016년도 춘계학술대회 및 임시총회
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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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Marine Sponges as a Drug Treasure

  • Anjum, Komal;Abbas, Syed Qamar;Shah, Sayed Asmat Ali;Akhter, Najeeb;Batool, Sundas;Hassan, Syed Shams ul
    • Biomolecules & Therapeutics
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    • 제24권4호
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    • pp.347-362
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    • 2016
  • Marine sponges have been considered as a drug treasure house with respect to great potential regarding their secondary metabolites. Most of the studies have been conducted on sponge's derived compounds to examine its pharmacological properties. Such compounds proved to have antibacterial, antiviral, antifungal, antimalarial, antitumor, immunosuppressive, and cardiovascular activity. Although, the mode of action of many compounds by which they interfere with human pathogenesis have not been clear till now, in this review not only the capability of the medicinal substances have been examined in vitro and in vivo against serious pathogenic microbes but, the mode of actions of medicinal compounds were explained with diagrammatic illustrations. This knowledge is one of the basic components to be known especially for transforming medicinal molecules to medicines. Sponges produce a different kind of chemical substances with numerous carbon skeletons, which have been found to be the main component interfering with human pathogenesis at different sites. The fact that different diseases have the capability to fight at different sites inside the body can increase the chances to produce targeted medicines.