• Title/Summary/Keyword: monoterpene

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Biotransformation of (-)-α-Pinene by Whole Cells of White Rot Fungi, Ceriporia sp. ZLY-2010 and Stereum hirsutum

  • Lee, Su-Yeon;Kim, Seon-Hong;Hong, Chang-Young;Kim, Ho-Young;Ryu, Sun-Hwa;Choi, In-Gyu
    • Mycobiology
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    • v.43 no.3
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    • pp.297-302
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    • 2015
  • Two white rot fungi, Ceriporia sp. ZLY-2010 (CER) and Stereum hirsutum (STH) were used as biocatalysts for the biotransformation of (-)-${\alpha}$-pinene. After 96 hr, CER converted the bicyclic monoterpene hydrocarbon (-)-${\alpha}$-pinene into ${\alpha}$-terpineol (yield, 0.05 g/L), a monocyclic monoterpene alcohol, in addition to, other minor products. Using STH, verbenone was identified as the major biotransformed product, and minor products were myrtenol, camphor, and isopinocarveol. We did not observe any inhibitory effects of substrate or transformed products on mycelial growth of the fungi. The activities of fungal manganese-dependent peroxidase and laccase were monitored for 15 days to determine the enzymatic pathways related to the biotransformation of (-)-${\alpha}$-pinene. We concluded that a complex of enzymes, including intra- and extracellular enzymes, were involved in terpenoid biotransformation by white rot fungi.

Apoptosis-Inducing Costunolide and a Novel Acyclic Monoterpene from the Stem Bark of Magnolia sieboldii

  • Park, Hee-Juhn;Kwon, Sang-Hyuk;Han, Yong-Nam;Choi, Jong-Won;Miyamoto, Ken-ichi;Lee, Sung-Ho;Lee, Kyung-Tae
    • Archives of Pharmacal Research
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    • v.24 no.4
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    • pp.342-348
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    • 2001
  • In a course of obtaining more amount of bioactive costunolide and successive phytochemical isolation from Magnolia sieboldii (Magnoliaceae), a novel acyclic monoterpene 1 named deoxygeraniol (2,6(E)-dimethyl-2,6-octadiene) was isolated along with $\beta$-sitosterol 3-O-linoleate (2), trilinolein (3) and high amount of costunolide (4) in the pure state. The structure of compound 1 was determined on the basis of spectroscopic data. Costunolide was found to induce apoptotic cell death in a dose-dependent manner by nucleosomal DNA ladder and flow cytometric analysis. Immunoblot analysis showed that the level of the anti-apoptotic protein, Bcl-2, was decreased, whereas the cleavage of poly-(ADP-ribose) polymerase was, activated furthermore, the N-acetyl-L-cysteine antioxidant effectively prevented costunolide-induced cytotoxicity. These results suggest that costunolide-induced cell death is mediated by reactive oxygen species.

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Lipoxygenase Inhibitory and Antioxidant Activities of Isolated Compounds from Moutan Cortex

  • Ha, Do-Thi;Trung, Trinh-Nam;Thuan, Nguyen-Duy;Yim, Nam-Hui;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.16 no.2
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    • pp.68-74
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    • 2010
  • Phytochemical investigation on the ethyl acetate and n-butanol fractions of Moutan Cortex resulted in the isolation and characterization of a new monoterpene glycoside (3) and twenty known monoterpene glycosides (1, 2, 4-21). The structure of 3 was determined by spectroscopic data interpretation and physico-chemical properties. Compounds 1 and 8 presented a remarkable inhibitory activity against lipoxygenase-1 (LOX-1) with $IC_{50}$ values of 45.2 and $37.5\;{\mu}M$, respectively. Compounds 9, 10, 13, 18, 19, and 21 showed significant 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging effect with $IC_{50}$ values of 9.8, 25.5, 6.4, 15.2, 18.7, and $23.7\;{\mu}M$, respectively. Benzoylpaeoniflorin (8), which exhibited the highest inhibitory effect with an $IC_{50}$ value of $37.5{\pm}0.7{\mu}M$, was further analyzed the inhibition kinetics by Lineweaver-Burk plots. Results indicated that 8 is a non-competitive inhibitor, and the kinetic parameter values were estimated to be ($31.04\;{\mu}M$, Ki), ($0.29\;{\mu}M/min$, $V_m$), and ($48.50\;{\mu}M$, $K_m$).

Research of Monoterpenes Content in the Atmosphere of Forest (산림치유 효능물질 함량에 관한 연구)

  • Ham, Kwang-Joon;Park, Keun-Young;Kim, Min-Su;Song, Jae-Mo;Lee, Sang-Soo;Ok, Yong-Sik
    • Korean Journal of Soil Science and Fertilizer
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    • v.44 no.6
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    • pp.1226-1231
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    • 2011
  • The biogenic emission of the atmospheric volatile organic compounds (VOCs) from the forests is dominated by monoterpenes. This study investigated the changes in the concentration of monoterpenes distributed in various types of forest near the Gangwon Nature Environment Research Park, Hongcheon, Gangwon Province, Korea. Samples were collected from the three sites of different types of forest, including coniferous, broad-leaved and mixed forests. Additionally, the seasonal and daily changes of monoterpene compounds were monitored. Our results found the several types of monoterpene such as ${\alpha}$-pinene, ${\beta}$-pinene, camphene, d-limonene, p-cymene and ${\alpha}$-terpinene. The highest total concentration of terpene compounds was observed in the coniferous forest. For the summer season, the total concentration of terpene compounds was highest in coniferous and mixed forests, and that was also highest in broad-leaved forest for the autumn.

Biochemical Substances from Normal Needles and Infested Needles Attacked by Thecodiplosis japonensis in Pinus densiflora, Pinus thunbergii and Pinus rigida (소나무, 해송(海松) 및 리기다소나무에 있어서 건전엽(健全葉)과 솔잎혹파리 피해엽(被害葉)의 생화학적(生化學的) 물질비교(物質比較))

  • Han, Sang Urk;Lee, Don Koo;Chon, Sang Keun
    • Journal of Korean Society of Forest Science
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    • v.50 no.1
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    • pp.49-55
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    • 1980
  • Monoterpenes, phenolic substances, growth substances and total nitrogen from normal needles and infested needles attacked by Thecodiplosis japonensis were compared for Pinus densiflora, Pinus thunbergii and Pinus rigida. The results obtained in this study were as follows: 1. Major monoterpene components in P. densiflora needles were ${\beta}$-phellandrene, ${\alpha}$-pinene and those in P. rigida needles were ${\beta}$-pinene and ${\alpha}$-pinene. In P. rigida resistant to this insect, infested needles showed higher ${\alpha}$-pinene, ${\beta}$-pinene and myrcene but lower camphene, limonene and ${\beta}$-phellandrene than normal needles. 2. Orcinol, catechol ferulic acid, salicylic acid and five unknowns were detected in P. rigida needles whereas orcinol, catechol, ferulic acid and four unknowns in P. densiflora needles. 3. Tryptophan, a precursor of IAA, was detected in larvae and also in gall tissues of both P. densiflora and P. thunbergii needles. This fact shows that growth substances may involve in gall formation by Thecodiplosis japonensis. 4. Total nitrogen contents per unit needle weight were neither significantly different between P. densiflora and P. rigida, nor between normal and infested needles.

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Comparison of Antifungal Activites of Monoterpenes and Sesquiterpenes in Essential Oil from Chamaecyparis obtusa against Dermatophytes (피부사상균에 대한 편백정유의 Mono- 및 Sesquiterpene 항진균 활성 비교)

  • Gwak, Ki-Seob;Park, Mi-Jin;Jeung, Eui-Bae;Chang, Je-Won;Choi, In-Gyu
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.3
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    • pp.46-55
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    • 2006
  • This study was to compare the antifungal activitiy of monoterpenes with that of sesquiterpenes, which were major constituents of antifungal active essential oil of Chamaecyparis obtusa, to investigate which constituents had more effective against dermatophytes, and to evaluate the synergistic effect of combination of the antifungal active constituents. The antifungal activities of seven fractions (A, B, C, D, E, F, and G) from C obtusa essential oil by column chromatography were tested against Trichophyton mentagrophytes. Fraction D, E, F, and G were more active than fraction A, B, and C, and their major compounds were mono- and sesquiterpenes analyzed by GC/MS. Borneol, linalool, and ${\alpha}$-terpineol were selected as monoterpenes, and ${\alpha}$-cedrol, nerolidol, and ${\beta}$-eudesmol as sesquiterpenes, respectively. The antifungal activities of the constituents were respectively examined against Trichophyton mentagrophytes (KCTC6077), Microsporum canis (KCTC6591), and Microsporum gypseum. The constituents of sesquiterpenes were more active than those of monoterpenes. By comparing single and combined sesquiterpenes with fraction F containing the higher ratio of sesquiterpenes, combined sesquiterpenes were the most active. This result indicated that there was the synergistic antifungal effect against dermatophytes when sesquiterpenes were combined together.

Emission Properties of Volatile Compounds from Medicine Herb Residues Board (한약재 찌꺼기로 제조한 한방보드의 휘발성 성분의 방출 특성)

  • Roh, JeongKwan
    • Journal of the Korean Wood Science and Technology
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    • v.44 no.3
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    • pp.430-439
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    • 2016
  • Medicine herb residues boards were manufactured by using medicine herb residues, and emission properties of volatile compounds from boards were examined under various temperature conditions. The volatile compounds were identified with analysis of TD GC/MS by absorbing their flavor components in Tenax tubes. Total 88 volatile compounds were identified from the board. The number of identified compounds at temperature conditions of $25^{\circ}C$, $35^{\circ}C$, and $45^{\circ}C$ were 44, 55, and 65 kinds, respectively. The number of volatile compounds and the total peak area tended to increase with an increase in the temperature. The number of the flavor components detected in all temperature conditions were 34 kinds. Hydrocarbon compounds showed 93% of the detected flavor compounds at $25^{\circ}C$, 92% at $35^{\circ}C$, and 90% at $45^{\circ}C$. Ether compounds accounted for 4% and ketone, aldehyde, and acid-type compounds were detected in a small quantity. The hydrocarbons were composed of 17 kinds of monoterpenes and 39 kinds of sesquiterpenes, which accounted for 11% and 80%, respectively. The most detected compound of monoterpene was limonene, and the major flavor components of sesquiterpenes were ${\alpha}-curcumene$, zingiberene, ${\beta}-elemene$, ${\beta}-selinene$, ${\alpha}-amorphene$, and ${\alpha}-copaene$. Anethole (3.26%) known for ether compounds was detected considerably in all temperature conditions. The results suggest that the manufactured medicine herb residues board include various types of flavor compounds and the flavor compounds might be useful for the manufacture of various products.

Breeding of Varieties of Pines Resistant to Pine Gall Midge. (Thecodiplosis japonensis Uchida et Inouye) (II) -Seasonal Variation of Needle Monoterpene Composition in Resistant Pinus thunbergii.- (솔잎혹파리 내충성(耐蟲性) 품종(品種) 육성(育成)에 관(關)한 연구(硏究) -2. 솔잎혹파리 내충성(耐蟲性) Pinus thunbergii의 침엽내(針葉內) monoterpene의 계절적변화(季節的變化))

  • Kim, C.S.;Hong, S.H.;Ryu, J.B.;Choi, C.;Kim, J.S.
    • Journal of Korean Society of Forest Science
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    • v.32 no.1
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    • pp.16-20
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    • 1976
  • Employing 7-15 resistant and 8-15 susceptible Japanese black pine (Pinus thunbergii Parl.) trees to pine gall midge (Thecodiplosis japonensis Uchida et Inouye) as samples, needle monoterpenes were analysed by GLC in January and June, and observation was made on the oviposition preference. Following results were obtained. 1. In January, the resistant trees showed higher contents of myrcene, limonene, ${\beta}$-phellandrene and terpinolene but lower contents of ${\alpha}$-and ${\beta}$-pinene and camphene compared to the susceptible trees. But in June, ${\alpha}$-pinene, camphene, limonene, ${\beta}$-phellandrene and terpinolene were higher and the content of ${\beta}$-pinene and myrcene were lower in the resistant trees than the susceptible trees. 2. The content of limonene was higher by the 6.8 percent and the content of ${\beta}$-pinene was lower by the 9.2 percent in the resistant trees than in the susceptible trees in June. 3. No preference for oviposition was found between resistant and susceptible trees. But in the resistant trees gall formation rate was quite lower than the susceptible trees. It was considered, therefore, that limonene and ${\beta}$-pinene content in the needle might be used as an indicator of the resistant Japanese black pine to the pine gall midge regardless of season.

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Comparison of Phytoncide (monoterpene) Concentration by Type of Recreational Forest (산림휴양지 유형에 따른 피톤치드(모노테르펜) 농도 비교)

  • Lee, Yong-Ki;Woo, Jung-Sik;Choi, Si-Rim;Shin, Eun-Sang
    • Journal of Environmental Health Sciences
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    • v.41 no.4
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    • pp.241-248
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    • 2015
  • Objectives: This study was conducted to provide scientific and effective information on phytoncides, which are associated with forest healing, and to activate recreational forests. Methods: The target sites were natural recreation forests, a forest park and an arboretum, and the control sites were three urban parks. The samples were collected at a volume of 6.0 L and a flow rate of 0.1 L/min for one hour using a low volume pump and the solid adsorbent sampling method. The phytoncide compounds adsorbed in the Tenax TA tube were analyzed by a automatic heat desorption unit and GC-MS. Results: By type of recreational forest, the annual concentrations of phytoncide (monoterpene) for the forest park showed the highest concentration with $1.450{\mu}g/m^3$, while those for the arboretum showed the lowest concentration at $0.892{\mu}g/m^3$, and thus the concentration of the forest park was approximately 1.6 times higher than the arboretum. The season showing the highest concentration of phytoncides was summer (June) and the forest park was the highest among the recreational forests. The concentrations of major components for phytoncide showed in descending order: ${\alpha}-pinene$, ${\beta}-pinene$, camphene, 3-carene and limonene. The seasonal concentration of ${\alpha}-pinene$, camphene and ${\beta}-pinene$ by type of recreational forest increased in April, which is characterized by low temperature and humidity, and the seasonal concentration of camphene decreased with higher humidity. The meteorological factors which had the high correlation with the concentration of total terpene were temperature and humidity. $CO_2$ and $O_2$ showed an inverse correlation. Conclusion: The major components of phytoncide were ${\alpha}-pinene$, ${\beta}-pinene$, camphene, 3-carene and limonene in descending order of concentration. Further and systematic study on the chemical nature of individual phytoncides, and on the effect of phytoncides on humans needs to be performed.

Peroxide Constituents in the Natural Product Research (천연물 연구에서의 Peroxide 성분)

  • Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.22 no.3
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    • pp.145-155
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    • 1991
  • Peroxides in natural products have been recently received a considerable attention due to their various biological and pharmacological properties. Nearly 300 peroxides have been isolated and structually characterized from natural sources, mainly as constituents of Compositae and marine sponge, and occur randomly in about 10 other plant families. Among peroxides studied, sesquiterpene endoperoxide, quinghaosu, has been already clinically applied as a new antimalarial drug. Based on the peroxides reported, structural classification, natural distribution and biological and pharmacological activities are reviewed. Color reagent and spectroscopic identification of peroxide are also described.

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