• 제목/요약/키워드: terpene compounds

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Allelopathy 작용성(作用性)을 나타내는 잡초(雜草)중의 휘발성(揮發性) Terpene류(類)의 동정(同定) (An Identification of Volatile Terpenes in Allelopathic Weeds)

  • 전재철;한강완
    • 한국잡초학회지
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    • 제9권2호
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    • pp.149-153
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    • 1989
  • Allelopathy 작용성(作用性)을 나타내는 4종(種)의 잡초(雜草) 중에 존재(存在)하는 휘발성(揮發性) terpene 물질(物質)을 GC 및 GC-MS로 동정(同定)하였다. 쑥에서는 26종(種)의 휘발성(揮發性) terpene 류(類)를 분리(分離) 동정(同定)하였는데 이들은 monoterpene 16종(種)과 sesquiterpene 10종(種)이었다. 또한 토끼풀에서는 4종(種), 쇠비름과 냉이에서 각(各) 3종(種)이 확인(確認)되었다. 동정(同定)된 terpene 중 allelopathy 작용성(作用性)을 나타내는 물질(物質)로는 쑥에서 ${\alpha}$-phellandrene, 1,8-cineole, limonene, ${\beta}$-pinene, borneol, selinene 및 caryophyllene, 토끼풀에서 ${\alpha}$-pinene과 ${\beta}$-caryophyllene, 그리고 냉이에서 ${\alpha}$-pinene 등이었고, 쇠비름 중에는 allelopathy 작용성(作用性)을 나타내는 휘발성(揮發性) terpene 류(類)는 없는 것으로 나타났다.

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Analysis of Volatile Compounds in Bulgogi Prepared by Different Heating Procedure

  • Cho, In-Hee;Lee, Hyong-Joo;Kim, Young-Suk
    • Food Science and Biotechnology
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    • 제14권3호
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    • pp.428-432
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    • 2005
  • To compare volatile compounds in bulgogi cooked by different heating procedures, bulgogi was prepared by convection oven, electric pan and charcoal grill. A total of 61 volatile compounds, consisting of 4 pyrazines, 10 sulfur-containing compounds, 7 carbonyls, 7 alcohols, 7 aliphatic hydrocarbons, 25 terpene hydrocarbons, and 1 miscellaneous compound, were tentatively identified in bulgogi cooked by the three heating methods. Comparatively, the difference in volatile compounds identified in bulgogi using the three different heating methods was not significant, except for sulfur-containing compounds and carbonyls which were detected at higher levels in the bulgogi cooked by convection oven than in that cooked by the other two heating methods. On the other hand, some compounds, such as furfural, benzaldehyde, and (E,E)-2,4-decadienal, were detected only in the bulgogi cooked by charcoal.

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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Changes in terpenes of three kinds of pine needles during litter decomposition

  • Jo, Gyu-Gap;Kim, Jong-Hee
    • Journal of Ecology and Environment
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    • 제33권2호
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    • pp.175-186
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    • 2010
  • This study was designed to evaluate changes in the terpene composition of 3 types of pines (Pinus densiflora, Pinus thunbergii and Pinus rigida), while decomposing their leaf litter. Needle litters were placed at two different organic layer depths, one on the surface and the other beneath the litter layer. Changes in the terpene composition of this litter were detected using a gas chromatograph-mass spectrometer. Among the monoterpenes acquired from the fresh needles of P. densiflora and P. rigida, $\alpha$-pinene (12.05% and 19.87%, respectively) was the major one, followed by $\beta$-pinene (2.90% and 14.07%). However, from the needles of P. thunbergii, $\beta$-pinene (20.77%) was the major one, followed by $\alpha$-pinene (10.79%). Among the sesquiterpenes detected in P. densiflora, trans-caryophyllene (3.12%) was the highest composition compound, whereas germacrene-D (6.09%) for P. thunbergii and 1,6-cyclodecadiene (7.41%) and endo-1-bourbonanol (7.41%) for P. rigida were the highest content compounds. However, the total amounts of terpenes decreased sharply by 40-85.4% in all three types of pine needle after 90-120 days of the experiment. The concentration of each terpene differed during decomposition, and the majority of compounds disappeared from beneath the litter layer. It was determined that three types of reducing patterns of each compound appeared on the rate of loss of concentration during decomposition; one pattern decreasing sharply during the initial period, another pattern steadily or slowly decreasing, and a newly detected pattern at low concentration occurring during decomposition.

Terpenes from Forests and Human Health

  • Cho, Kyoung Sang;Lim, Young-ran;Lee, Kyungho;Lee, Jaeseok;Lee, Jang Ho;Lee, Im-Soon
    • Toxicological Research
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    • 제33권2호
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    • pp.97-106
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    • 2017
  • Forest bathing has beneficial effects on human health via showering of forest aerosols as well as physical relaxation. Terpenes that consist of multiple isoprene units are the largest class of organic compounds produced by various plants, and one of the major components of forest aerosols. Traditionally, terpene-containing plant oil has been used to treat various diseases without knowing the exact functions or the mechanisms of action of the individual bioactive compounds. This review categorizes various terpenes easily obtained from forests according to their anti-inflammatory, anti-tumorigenic, or neuroprotective activities. Moreover, potential action mechanisms of the individual terpenes and their effects on such processes, which are described in various in vivo and in vitro systems, are discussed. In conclusion, the studies that show the biological effectiveness of terpenes support the benefits of forest bathing and propose a potential use of terpenes as chemotherapeutic agents for treating various human diseases.

Structural Insights into the Interaction of Terpenoids with Streptomyces avermitilis CYP107P2

  • Eunseo Jeong;Vitchan Kim;Changmin Kim;Yoo-bin Lee;Donghak Kim
    • Biomolecules & Therapeutics
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    • 제32권4호
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    • pp.474-480
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    • 2024
  • Streptomyces avermitilis genome includes 33 genes encoding monooxygenation-catalyzing cytochrome P450 enzymes. We investigated the structure of CYP107P2 and its interactions with terpenoid compounds. The recombinant CYP107P2 protein was expressed in Escherichia coli and the purified enzyme exhibited a typical P450 spectrum upon CO-binding in its reduced state. Type-I substrate-binding spectral titrations were observed with various terpenoid compounds, including α-pinene, β-pinene, α-terpinyl acetate, and (+)-3-carene. The calculated binding affinities (Kd) ranged from 15.9 to 50.8 µM. The X-ray crystal structure of CYP107P2 was determined at 1.99 Å resolution, with a well-conserved overall P450 folding conformation. The terpenoid compound docking models illustrated that the structural interaction between monoterpenes and CYP107P2, with the distance between heme and terpenes ranging from 3.4 to 5.4 Å, indicates potential substrate binding for P450 enzyme. This study suggests that CYP107P2 is a Streptomyces P450 enzyme capable of catalyzing terpenes as substrates, signifying noteworthy advancements in comprehending a novel P450 enzyme's involvement in terpene reactions.

무등산 숲과 도심에서 휘발성유기화합물질의 분포 특성 (Distribution characteristics on volatile organic compounds at the forest of Mt. mudeung and downtown)

  • 이대행;박강수;이세행;송형명;이기원;정희윤;서광엽;조영관;김은선
    • 분석과학
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    • 제28권3호
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    • pp.246-254
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    • 2015
  • 무등산 탐방로 8개 지점과 도심 1개 지점에서 2013~2014년에 자연 기원 휘발성유기화합물질 (BVOCs)과 인위적인 휘발성유기화합물질 (AVOCs)의 분포특성을 GC-MSD를 사용하여 조사하였다. 자연기원 휘발성유기화합물인 테르펜 발생량은 편백숲인 PA 지점이 821 pptv으로 가장 높았고, WH 지점이 785 pptv, NZ 지점이 679 pptv, DJ 지점이 513 pptv, JB 지점이 476 pptv, SS 지점이 464 pptv 순으로 조사되었다. 테르펜은 지점별로 11~15 종이 검출되었는데, 5월에 PA 지점에서는 α-pinene이 20%로 가장 높고, coumarin, sabinene, phellandrene, myrcene, borneol, eucalyptol, β-pinene, cymene, δ-limonene, γ-terpinene, camphor, camphene, mentol 순이었다. 인위적인 휘발성유기화합물질(AVOCs)은 5~7월에 숲 8개 지점에서 0.74~2.52 ppbv 이었고, 도심(JW 지점)에서는 3.14 ppbv로 나타나 도심/산림 비율은 1.9~4.0로 도심지역이 높았다. JW 지점에서 벤젠과 톨루엔만 합한 농도는 평균 2.37 ppbv로 AVOCs 10항목 전체의 75%를 차지했다. 6월 중 AVOCs 종별 분포조사 결과, 숲인 DJ 지점에서 toluene이 44.1%로 가장 많았고, 도심인 JW 지점에서도 toluene이 53.1%로 가장 많았다. 또한, 숲에서 AVOCs와 BVOCs 농도의 상관성 분석 결과, 양의 상관계수가 0.328이나 유의인자(p)는 0.184로서 통계적으로 유의하지 않는 것으로 나타나 숲에서의 AVOCs는 도심에서 영향을 받은 것으로 추정된다.

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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Cytotoxic Terpene Hydroperoxides from the Aerial Parts of Aster spathulifolius

  • Lee, Sung-Ok;Choi, Sang-Zin;Choi, Sang-Un;Kim, Gun-Hee;Kim, Young-Choong;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • 제29권10호
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    • pp.845-848
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    • 2006
  • Three new sesquiterpene hydroperoxides, 1-[3-(2-hydroperoxy-3-methylbut-3-en)-4-hydroxyphenyl]ethanone (2), $7{\beta}-hydroperoxy-eudesma-11-en-4-ol$ (3), and $7{\alpha}-hydroperoxymanool$ (4), together with three known compounds, germacrone (1), ent-germacra-4(15),5,10(14)-trien-$1{\alpha}$-ol (5) and teucdiol A (6) were isolated from the aerial parts of Aster spathulifolius (Compositae). Their structures were characterized using chemical and spectroscopic methods. The isolated compounds were tested for their cytotoxicity against five human tumor cell lines in vitro using a SRB method. The two new compounds, 3 and 4, showed moderate cytotoxicity against human cancer cells with $ED_{50}$ values ranging from 0.24 to $13.27\;{\mu}g/mL$.