• 제목/요약/키워드: Eudesmol

검색결과 32건 처리시간 0.031초

Influence of ${\beta}-Eudesmol$ on Blood Pressure

  • Lim, Dong-Yoon;Kee, Young-Woo
    • Natural Product Sciences
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    • 제11권1호
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    • pp.33-40
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    • 2005
  • The present study was undertaken to investigate the effects of ${\beta}-eudesmol$, one of various ingredients isolated and identified from the bark of Magnolia obovata Thunberg, on arterial blood pressure and vascular contractile responses in the normotensve rats and to establish its mechanism of action. ${\beta}-Eudesmol\;(30{\sim}300\;{\mu}g/kg)$ given into a femoral vein of the normotensive rat produced a dose-dependent depressor response. These ${\beta}-eudesmol-induced$ hypotensive responses were markedly inhibited in the presence of chlorisondamine (1.0 mg/kg, i.v.) or phentolamine (2.0 mg/kg, i.v.). Interestingly, the infusion of ${\beta}-eudesmol$ (1.0 mg/kg/30min) into a femoral vein made a significant reduction in pressor responses induced by intravenous norepinephrine. Furthermore, the phenylephrine $(10^{-5}\;M)-induced$ contractile responses were depressed in the presence of high concentrations of ${\beta}-eudesmol\;(10{\sim}40\;{\mu}g/ml)$, but not affected in low concentration of ${\beta}-eudesmol\;(2.5{\sim}5\;{\mu}g/ml)$. Also, high potassium $(5.6{\times}10^{-2}\;M)-induced$ contractile responses were greatly inhibited in the presence of ${\beta}-eudesmol\;(10{\sim}40\;{\mu}g/ml)$ in a dose-dependent fashion. Taken together, these results obtained from the present study demonstrate that intravenous ${\beta}-eudesmol$ causes a dose-dependent depressor action in the anesthetized rat at least partly through the blockade of vascular adrenergic ${\alpha}_1-receptors$, in addition to the some unknown mechanism of direct vasorelaxation.

$\beta$-EUDESMOL CAUSES VASODILATORY EFFECT IN THE NORMOTENSIVE RAT

  • Lim, Dong-Yoon;Shin, Hye-Gyeong
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.138.1-138.1
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    • 2003
  • $\beta$-Eudesmol is one of various compounds derived from the bark of Magnolia obovata Thunberg, a medicinal plant. It has been shown that $\beta$-eudesmol also markedly alleviated muscle fasciculation, tremor and convulsion induced by diisopropylfluorophosphate and prolonged the time to death in mice (Chiou et al., 1995). Actually, the extract of magnolia bark has been shown to have depressant actions on the cental nervous system (Watanabe et al., 1973). (omitted)

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Angelica속 생약의 정유성분에 관한 연구 (I). -참당귀의 정유성분- (Studies on Essential Oils of Plants of Angelica Genus in Korea (I). -Essential Oils of Angelicae gigantis Radix-)

  • 지형준;김현수
    • 생약학회지
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    • 제19권4호
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    • pp.239-247
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    • 1988
  • Essential oil of the root of Angelica gigas Nakai (Umbelliferae) was investigated. Essential oil was obtained from the dried roots by steam distillation and fractionated by column chromatography. Each isolate or fraction was identified by GC, GC-MS and spectral analysis. It was found to contain eleven monoterpenes such as ${\alpha}-pinene,\;camphene,\;{\beta}-pinene,\;myrcene,\;{\alpha}-phellandrene,\;{\Delta}-3-carene,\;{\alpha}-terpinene,\;p-symene,\;limonene,\;{\gamma}-terpinene$ and terpinolene and also found to contain 4-vinylguauacol, myristicin, elemol, ${\beta}-eudesmol,\;{\alpha}-eudesmol,\;four\;sesquiterpenes\;involving\;{\Delta}-elemene$. Four sesquiterpenes and five sesquiterpene alcohols were tentatively identified by comparison of their mass spectra.

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국내산 참당귀 추출물의 휘발성 향기성분

  • 곽재진;이재곤;장희진;김옥찬
    • 한국연초학회지
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    • 제20권2호
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    • pp.210-217
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    • 1998
  • Volatile flavor components of extracts produced from the domestic angelica root, which are oleoresin and absolutes type, for tobacco flavoring materials were isolated by solvent extraction method and were analyzed by GC and GC/MSD. And then volatile flavor components of oleoresin were compared with volatiles isolated from absolutes. A total of 65 components were identified in the angelica root extracts, from which 41 components were identified in the oleoresin volatiles, contained 15 hydrocarbons, 12 alcohols, 6 acids, 10 esters and 2 miscellaneous components. The major components were hexadecanoic acid (7.79%), methyl palmitate (6.49%), ethyl palmitate (2.02 %) and sesquiterpenes and sesquiterpene alcohols, such as elemol (2.92 %), ${\gamma}$-selinene (2.19%), $\beta$-selinene (2.02%), $\alpha$-eudesmol (3.49%) and $\beta$-eudesmol (6.12%). On the other hand, volatiles of absolutes, from which 60 components were identified, contained 28 hydrocarbons, 14 alcohols, 5 acids, 10 esters and 3 miscellaneous components. The major components were hyrocarbons, such as undecane (5.11 %), dodecane (3.10%) and pentadecane (1.14 %), and $\alpha$-muurolene (1.64 %), ${\gamma}$-selinene (1.49%), $\beta$-selinene (2.12 %), $\alpha$-eudesmol (2.25%), $\beta$-eudesmol (4.87%), hexadecanoic acid (12.67%) and hexanoic acid (1.87 %).

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Eudesmols Induce Apoptosis through Release of Cytochrome c in HL-60 Cells

  • Hoang, Duc Manh;Trung, Trinh Nam;He, Long;Ha, Do Thi;Lee, Myoung-Sook;Kim, Bo-Yeon;Luong, Hoang Van;Ahn, Jong-Seog;Bae, Ki-Hwan
    • Natural Product Sciences
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    • 제16권2호
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    • pp.88-92
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    • 2010
  • We verified that the apoptosis activities were examined by DNA fragmentation, flow cytometric analysis with annexin V staining, activation of caspase-3, and cytochrome c release. In the result, $\alpha$- and $\beta$-eudesmol induced DNA fragmentation in HL-60 cells at a concentration of $80\;{\mu}M$, respectively. Additionally, pro-apoptotic cells sorted by flow cytometry analysis were detected in HL-60 cells to 31.77 and 29.67% with $\acute{a}$- and $\beta$-eudesmol of $80\;{\mu}M$. Thus, both $\alpha$- and $\beta$-eudesmol exerted caspase-3 activation and cytochrome c release at $80\;{\mu}M$ in HL-60 cells. These results are firstly reported that the sesquiterpenes, $\alpha$- and $\beta$-eudesmol are apoptosis inducers through mitochondria-dependent caspase cascade in HL-60 cells.

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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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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삼나무 정유의 표재성 진균에 대한 항진균 활성 (Antifungal activity of essential oil from Cryptomeria japonica against dermatophytic fungi)

  • 김선홍;이수연;홍창영;정한섭;박미진;최인규
    • Journal of the Korean Wood Science and Technology
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    • 제40권4호
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    • pp.276-286
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    • 2012
  • 본 연구에서는 표재성 진균에 의한 피부질환 개선용 소재로의 개발을 위해 삼나무 정유의 표재성 알레르기성 진균, Trichophyton schoenleinii, Trichophyton tonsurans, Trichophyton mentagrophytes (interdigitale), Trichophyton rubrum, Epidermophyton floccosum, Aspergillus fumigatus에 대한 항진균 활성을 평가하여 삼나무 정유의 표재성 진균에 의한 피부질환 개선 소재로의 개발 가능성을 평가하고자 하였다. 항진균 활성 평가는 삼나무 정유의 MIC (Minimum Inhibitory Concentration) 측정과 TLC bioassay, 한천희석법을 통해 측정하였다. 또한 활성 성분의 주성분을 확인하기 위해 GC/MS 분석을 실시하였다. 삼나무 정유 crude oil의 MIC는 모든 균에서 500 ppm 이하의 농도 값을 나타냈으며, TLC bioassay를 통해 spot 1에서 항진균 효과를 확인하였다. 한천희석법을 통한 항진균 활성은 A. fumigatus를 제외한 모든 진균에 대해 삼나무 정유 crude oil의 경우, 500 ppm 이상에서 100%의 활성을 나타냈고, 분획 D의 경우, 100 ppm에서도 100%의 활성을 나타냈다. TLC bioassay를 통해 항진균 활성을 나타낸 spot 1과 한천희석법을 통해 활성을 나타낸 분획 D를 GC/MS로 분석한 결과 주성분은 elemol, ${\gamma}$-eudesmol, ${\beta}$-eudesmol이었다. 따라서 elemol, eudesmol 등은 표재성 진균에 의한 피부질환의 개선 소재로의 이용 가능성이 충분하다고 사료된다.

Angelica속 생약의 정유성분에 관한 연구(IV) -강활의 정유성분- (Studies on Essential Oils of Plants of Angelica Genus in Korea (IV) -Essential Oils of Angelicae koreanae Radix-)

  • 지형준;김현수
    • 생약학회지
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    • 제24권2호
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    • pp.111-115
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    • 1993
  • Essential oil of the root of Angelica koreana Max. (Umbelliferae) was investigated. Essential oil was obtained from the dried roots by steam distillation and fractionated by column chromatography. Each isolate or fraction was identified by GC, GC-MS and spectral analysis. It was found to contain nine monoterpenes such as ${\alpha}-pinene$(7.0%), camphene, ${\beta}-pinene$, myrcene, ${\alpha}-phellandrene$, ${\Delta}-3-carene$, p-cymene, limonene(2.8%), terpinolene and also found to contain m-cresol(11.6%), citronellol, citral b, methylcinnamate, eudesmol and osthol. 2-Hydroxy-5-methylacetophenone and twelve compounds were tentatively identified.

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New Assay Method for Surveying Anti-Emetic Compounds from Natural Sources

  • Akita, Y.;Yang, Y.;Kawai, T.;Kinoshita, K.;Koyama, K.;Takahashi, K.;Watanabe, K.
    • Natural Product Sciences
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    • 제4권2호
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    • pp.72-77
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    • 1998
  • The new assay method was developed by using young chicks instead of frogs for screening of anti-emetic compounds from natural sources. Comparing with our previous method using leopard and ranid frogs, the advantages of the new method were not only completely parallel results but also decreasing standard errors. Hinesol and eudesmol were isolated from MeOH extract of Atractylodes lancea rhizome as the anti-emetic principles.

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