• 제목/요약/키워드: trans,trans-farnesol

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목재부후균에 의한 trans,trans-farnesol의 생물변환 (Biotransformation of trans,trans-farnesol by Wood Rot Fungi)

  • 김영훈;이수연;박미진;최인규;이재원
    • 미생물학회지
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    • 제48권1호
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    • pp.37-41
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    • 2012
  • 본 연구에서는 sesquiterpene류의 생물학적 변환을 위한 생촉매로서 목재부후균을 선발하고 생물변환 가능성을 확인하였다. Sesquiterpene류 합성 전구체로 알려진 trans,trans-farnesol을 기질로 하여 총 19종의 목재부후균에 대해여 저항성 실험을 실시하였다. 기질의 농도를 달리하여 저항성 테스트를 실시하여 생물변환 가능성을 갖는 5종의 균주를 선발하였으며 선정된 균주를 이용하여 액체배지 조건에서 trans,trans-farnesol의 생물변환을 시도하였다. GC/MS를 이용하여 분석한 결과 Laetiporus sulphureus var. miniatus (jungh) Imaz, Coriolus versicolor (L. Fr). Prlar, Fomitopsis pinicola, Lampteromyces japonicas 등 4개의 균주에서 각각 nerolidol, eicosane, isoborneol, isocyclocitral 등의 대사산물을 확인할 수 있었다. 이와 같은 결과로 sesquiterpene류의 생물학적 변환을 위한 생촉매로서 목재부후균의 가능성을 확인하였다.

Characteristic Impact Odorants of Changpo (Acorus calamus var. angustatus Bess) Root Essential Oil

  • Choi, Hyang-Sook
    • Food Science and Biotechnology
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    • 제14권4호
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    • pp.450-455
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    • 2005
  • This study was conducted to determine firstly the composition of the essential oil from fresh changpo (Acorus calamus var. angustatus Bess) roots quantitatively and qualitatively by use of two internal standards, and secondly volatile compounds which are primarily responsible for the aroma of changpo roots. Simultaneous steam distillation and extraction method was used for essential oil extraction, and aroma extract dilution analysis (AEDA) and sniffing test by gas chromatography/olfactometry (GC/O) were used to detect the characteristic impact odorants. According to the instrumental analysis of changpo root essential oil, cis, trans-famesol (47.56 mg/kg of fresh wt), octanoic acid (23.73 mg/kg of fresh wt), trans-2-dodecenal (20.28 mg/kg of fresh wt) and trans, trans-farnesol (13.81 mg/kg of fresh wt) were the most abundant compounds. Geranyl acetate, trans-nerolidol and trans, trans-farnesyl acetate were evaluated as the characteristic impact odorants of changpo roots from results of AEDA and sniffing test. Especially, geranyl acetate was considered as the most similar odor component to changpo roots by organoleptic evaluation with GC/O.

The chloroform fraction of Citrus limon leaves inhibits human gastric cancer cell proliferation via induction of apoptosis

  • Osman, Ahmed;Moon, Jeong Yong;Hyun, Ho Bong;Kang, Hye Rim;Cho, Somi Kim
    • Journal of Applied Biological Chemistry
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    • 제59권3호
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    • pp.207-213
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    • 2016
  • Little information about the biological activities of Citrus limon (lemon) leaves has been reported, whereas the fruit of Citrus limon (lemon) has been well-documented to contain various pro-health bio-functional compounds. In the present study, the antiproliferative activities of the lemon leaves were evaluated using several cancer cell lines. From the n-hexane, chloroform, ethyl acetate, n-butanol, and water fractions of methanolic extract of the leaves, the chloroform fraction of lemon leaves (CFLL) showed the most potent antiproliferative activity in the AGS human gastric cancer cells. The current study demonstrates that CFLL induces apoptosis in AGS cells, as evidenced by an increase in apoptotic bodies, cell population in the sub-G1 phase, Bax/Bcl-2 ratio, and cleavage of poly (ADP-ribose) polymerase (PARP), caspase-3 and caspase-9. Compositional analysis of the CFLL using gas chromatography mass spectrometry (GC-MS) resulted in the identification of 27 compounds including trans, trans-farnesol (3.19 %), farnesol (3.26 %), vanillic acid (1.45 %), (-)-loliolide (5.24 %) and palmitic acid (6.96 %). Understanding the modes of action of these compounds individually and/or synergistically would provide useful information about their applications in cancer prevention and therapy.

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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노간주나무(Juniperus rigida Sieb. et Zucc.) 열매의 지질 및 향기성분 분석 (Analyses of Lipid and Volatile Components in Juniper Seed(Juniperus rigida Sieb. et Zucc.))

  • 신원선;하재호
    • 한국식품영양과학회지
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    • 제32권6호
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    • pp.795-800
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    • 2003
  • 우리 나라의 해안지역 및 전국의 산야에 분포하고 있는 노간주나무는 예로부터 열수추출하거나, 알코올로 추출하여 민간요법에 이용해온 예는 다수 있으나, 현재에는 그 이용여부가 보고된 바 없다. 노간주나무의 잎 및 열매로부터 추출한 지질의 물리화학적 특성을 규명하기 위하여 노간주나무의 잎과 열매의 지질의 일반성분 및 지방산 조성을 분석하고 굴절률, 산가, 검화가, 요오드화가, 인 함량 등을 측정하였다. 노간주나무의 열매로부터 추출한 지질의 경우, 산가는 91.04, 요오드가는 133.60, 굴절률은 1.4724, 검화가는 82.38, 불검화가는 15.52, 인 함량은 11.02 ppm이었다. 열매의 지방산조성을 분석한 결과, 8월에 채취한 시료로부터 추출한 지질에서는 중쇄 지방산인 lauric acid 및 caprylic acid 등이 약 50% 정도 차지하고 있었으나, 열매의 성수기에 접어드는 10월에 채취한 시료에는 전체 지방함량중 linoleic acid가 47.64%, linolenic acid가 17.55%, oleic acid가 16.05%, palmitic acid가 11.19%의 순으로 계절에 따른 지방산의 분포 및 조성비가 상이한 것으로 나타났다. 노간주나무의 열매로부터 SPME를 이용하여 추출한 정유성분의 휘발성성분의 조성을 GC-MSD로 분석한 결과, 주된 향기성분은 $\beta$-myrcene, $\alpha$-pinene, $\beta$-farnesene, $\beta$-cubebene, limonene 등이었으며, transcaryophyllene, $\alpha$-terpinolene 등과 camphene, sabinene, $\beta$-pinene, ${\gamma}$-terpinene, 1,4-terpineol, $\alpha$-fenchyl acetate, 2-undecanone, neryl acetate, jupinene, $\delta$-cadinene, germa acrene, farnesol 등이 검출되었고 원자방출검출기 (AED)를 이용하여 분석한 결과, 특이적인 황화합물 및 질소화합물 등이 검출되지 않았다.

저장조건에 따른 당귀의 정유성분 변화 (Volatile Flavor Components of Angelica gigas Nakai by the Storage Conditions)

  • 최성희;김혜정
    • 한국식품과학회지
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    • 제32권3호
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    • pp.513-518
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    • 2000
  • 당귀의 정유물을 Nickerson 동시 중류 추출법으로 추출하여, 저장온도와 기간에 따른 정유량의 변화를 비교하였고, 저장 60일째의 각 시료의 휘발성 성분을 GC 및 GC-MS법으로 분석, 동정하였다. 당귀의 정유함량을 비교한 결과 저장 10일째는 저온저장$(1{\sim}5^{\circ}C)$과 상온저장한 당귀는 저장직전에 분석한 당귀의 정유량과 거의 차이가 없었으나 20일 이후에는 저온저장한 당귀 시료의 정유량이 상온저장한 당귀의 정유량보다 함량이 많았다. 상온저장한 시료는 저장기간이 길어짐에 따라 정유량의 중가가 완만하다가 60일에는 정유량이 증가하였다. 저온 저장한 시료는 저장기간 20일째는 정유량의 현저한 중가추세를 보였으나 60일까지는 유지 혹은 완만한 중가추세를 보였다. 당귀의 휘발성 성분을 분석한 결과 당귀의 주요 향기성분으로 극성 컬럼에서는 ${\beta}-elemene$ 등의 terpene hydrocarbon류, eudesmol 등의 terpene alcohol류, (-)-trans-myrtanyl acetate ester 등이 둥정되었다. 비극성 컬럼에서는 camphene 등의 terpene hydrocarbon류, ${\alpha}-eudesmol$ 둥의 terpene alcohol류, butylidene phthalide 등이 동정되었다. 특히 eudesmol류는 상온저장에서 전체 정유량의 45%, 저온저장에서 48%를 차지했다. 당귀의 휘발성 성분으로 극성과 비극성 컬럼에서 함량이 많은 eudesmol과 terpene alcohol류 등은 독특하고 상쾌한 당귀의 향에 기여하리라고 생각된다. 저장 방법 면에서 상온저장한 시료와 저온 저장한 시료를 비교해보면 당귀의 대부분의 향기성분의 함량은 저온저장한 시료에서 많았다. 그리고 eudesmol은 전체적으로 상온저장 시료와 저온저장 시료 양쪽에서 많았으나 저온저장한 시료 쪽의 함량이 더 많았다.

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