• Title/Summary/Keyword: caryophyllene oxide

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Emission Rates of Biogenic Volatile Organic Compounds from Various Tree Species in Korea (II): Major Species in Urban Forests (국내 수종별 BVOCs 방출량(II): 도시 숲 주요 수종)

  • Hanna, Chang;Jounga, Son;Juwan, Kim;Junhyuk, Kim;Yeongseong, Kim;Won-Sil, Choi;Young-Kyu, Lee
    • Journal of Korean Society of Forest Science
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    • v.111 no.4
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    • pp.490-501
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    • 2022
  • In this study, the isoprene and terpene emissions from 32 major urban tree species were investigated. We conducted sampling using a dynamic enclosure system between June and July 2021. Seedlings aged < three years were enclosed in a chamber consisting of a 400 L transparent Tedlar bag. The air flow from the outlet of the chamber was sampled using Tenax-filled sorbent tubes under standard conditions (temperature: 30°C; PAR: 1,000 μmol/m2/sec). A thermal desorption gas chromatography/mass spectrometry system was used to analyze the following 38 biogenic volatile organic compounds: isoprene, monoterpenes, sesquiterpenes, oxygenated monoterpenes, and oxygenated sesquiterpenes. Isoprene emitters included Quercus mongolica, Salix koreensis, Robinia pseudoacacia, and Salix chaenomeloides. Monoterpene emitters included Pinus strobus, Cedrela sinensis, and Cercis chinensis. The monoterpene emission profiles were dominated by á-pinene, myrcene, camphene, and limonene. The predominant oxygenated monoterpene and oxygenated sesquiterpene were eucalyptol and caryophyllene oxide, respectively. For all species, the contributions of sesquiterpenes and oxygenated sesquiterpenes were relatively low.

Profiling of Volatile Components Using Gas Chromatography-Mass Spectrometry in Commercial Pine Needle (Pinus densiflora S. and Z.) Powder

  • Kim, Joo-Shin;Chung, Hau-Yin
    • Preventive Nutrition and Food Science
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    • v.16 no.1
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    • pp.45-54
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    • 2011
  • Volatile components in commercial pine needle (Pinus densiflora S. and Z.) powder were extracted using simultaneous steam distillation and a solvent extraction (SDE) apparatus, and were analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 230 compounds divided into 13 groups were identified, which included alcohols (42), ketones (39), aldehydes (32), terpenes (30), alkenes (17), esters (14), furans (14), benzenes (10), alkanes (8), napthalenes (7), acids (6), miscellaneous compounds (6), and phenols (5). Among the 230 compounds identified, 96 compounds were positively confirmed and quantified, and the rest of the compounds were tentatively identified. The major volatile components identified at relatively high levels were dodecanoic acid, hexadecanoic acid, hexanal, benzaldehyde, (Z)-3-hexen-1-ol, 1-penten-3-one, limonene, and $\beta$-caryophyllene oxide. Among the groups, terpenes accounted for 60.18% of the total concentration of all the volatile components. Some volatile components might account for the unique aroma and the biological activity of the sample.

Phytochemical Constituents of Amomum xanthioides

  • Choi, Jung-Wook;Kim, Ki-Hyun;Lee, Il-Kyun;Choi, Sang-Un;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.15 no.1
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    • pp.44-49
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    • 2009
  • Seven monoterpenes, three sesquiterpenes, three phenolics and one flavonoid were isolated from the MeOH extract of Amomum xanthioides. Their structures were determined by spectroscopic methods to be caryophyllene oxide (1), bornyl acetate (2), nerolidol (3), spathulenol (4), (-)-borneol (5), (+)-5-endohydroxycamphor (6), vanillic acid (7), protocatechuic acid methyl ester (8), betulabuside A (9), (1R,4S,6R)-6-hydroxyfenchan-2-one-6-O-$\beta$-D-glucopyranoside (10), (1S,4R,6S)-6-hydroxybornan-2-one-6-O-$\beta$-D-glucopyranoside (11), (1R,2S,4S,5R)-angelicoidenol 2-O-$\beta$-D-glucopyranoside (12), 1-O-vanilloyl-$\beta$-D-glucopyranoside (13), and quercetin-3-rhamnopyranoside (14). Compounds 6-14 were isolated for the first time from this plant source. Compounds 3 and 4 exhibited moderate cytotoxicity against four human cancer cell lines in vitro using a SRB bioassay.

Chemical Composition of Cirsium japonicum var. ussurience Kitamura and the Quantitative Changes of Major Compounds by the Harvesting Season (엉겅퀴 정유의 화학적 조성 및 수확시기에 따른 주요 화합물 함량 변화)

  • Choi, Hyang-Sook
    • The Korean Journal of Food And Nutrition
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    • v.29 no.3
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    • pp.327-334
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    • 2016
  • This study investigated the chemical composition of Cirsium japonicum var. ussurience Kitamura essential oil and the quantitative changes of major volatile flavor compounds according to the harvesting season. The essential oils obtained by the method of hydrodistillation extraction from aerial parts of C. japonicum var. ussurience Kitamura were analyzed by GC and GC-MS. Sixty-four volatile flavor compounds were identified in the essential oil from C. japonicum var. ussurience Kitamura harvested in May 2012; hexadecanoic acid (49.31%) was the most abundant compound, followed by 6,10,14-trimethyl-2-pentadecanone (13.72%), phytol (13.40%) and 9-hexadecenoic acid (4.16%). Eighty-three compounds were identified in the essential oil from the plant harvested in October 2012; phytol (40.56%), hexadecanoic acid (17.69%), 6,10,14-trimethyl-2-pentadecanone (13.71%), and caryophyllene oxide (4.15%) were the most abundant compounds. Types and levels of volatile compounds from different harvesting seasons varied. The essential oil composition of C. japonicum var. ussurience Kitamura harvested in the spring and autumn was characterized by higher contents of aliphatic fatty acid, diterpene and sesquiterpene, respectively.

Antioxidant Activity of Essential Oils from Wedelia chinensis (Osbeck) in vitro and in vivo Lung Cancer Bearing C57BL/6 Mice

  • Manjamalai, A.;Grace, V.M. Berlin
    • Asian Pacific Journal of Cancer Prevention
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    • v.13 no.7
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    • pp.3065-3071
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    • 2012
  • Aim: The present investigation was to evaluate the effects of essential oils of Wedelia chinensis (Osbeck) on free radicals and in vivo antioxidant properties. Methods: Essential oils were extracted using hydro-distillation and compound analysis was performed by GC-MS analysis. Screening for inhibitory activity was conducted by DPPH and OH-scavenging assays. In addition an in vivo study was carried out in cell line implanted cancer bearing mice with assessment of levels of catalase, superoxide dismutase, glutathione peroxidase, lipid peroxidation, nitric oxide and reduced glutathione. Finally, lungs were dissected out for histopathology study of metastasis. Results: GC-MS analysis revealed the presence of carvocrol and trans-caryophyllene as the major compounds with 96% comparison with the Wilily and NBS libraries. The essential oil exhibited significant inhibition in DPPH free radical formation. Whereas reducing power and hydroxyl radical scavenging activity are dose dependent. When compared with the standard, it was found that the essential oil has more or less equal activity in scavenging free radicals produced. In the animal studies, the level of antioxidant enzymes catalase, superoxide dismutase and glutathione peroxidase, as well as glutathione, were found to be increased in treated groups whereas lipid peroxidation and nitric oxide were reduced. Histopathology report also shows that the essential oil has a significant combating effect against cancer development. Conclusion: In all the in vitro assays, a significant correlation existed between the concentrations of the essential oil and percentage inhibition of free radicals. The in vivo studies also has shown a very good antioxidant property for the essential oil during cancer development. From, these results the essential oil can be recommended for treating disease related to free radicals and to prevent cancer development.

The Respective Effects of Shoot Height and Conservation Method on the Yield and Nutritive Value, and Essential Oils of Wormwood (Artemisia montana Pampan)

  • Kim, S.C.;Adesogan, A.T.;Ko, Y.D.
    • Asian-Australasian Journal of Animal Sciences
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    • v.19 no.6
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    • pp.816-824
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    • 2006
  • This study was conducted to evaluate the shoot height at which the yield and nutritive value of wormwood (Artemisia montana) is optimized in order to provide information on its potential to support animal production (Experiment 1). A second objective was to determine how the essential oil (EO) concentration in wormwood hay and silage differ (Experiment 2). In Experiment 1, Artemisia montana was harvested at five different shoot heights (20, 40, 60, 80 and 100 cm) from triplicate $1.8{\times}1.8m$ plots. Dry matter (DM) yield was measured at each harvest date and the harvested wormwood was botanically separated into leaf, stalk and whole plant fractions and analyzed for chemical composition and in vitro dry matter digestibility (DMD). Values for total digestible nutrients (TDN), digestible energy (DE) and metabolizable energy (ME) were subsequently calculated using prediction equations. Dry matter yields of stalk and whole plant increased linearly (p<0.001) and leaf yield increased quadratically (p<0.01) with shoot height, whereas the leaf/stalk ratio decreased linearly (p<0.001). As shoot height increased, there was a linear increase (p<0.001) in leaf DM, ether extract (EE) and neutral detergent fiber (NDF) contents and a quadratic increase (p<0.05) in leaf acid detergent fiber (ADF) and nitrogen free extract (NFE) contents, and stalk and whole plant DM (p<0.001), organic matter (OM, p<0.01 and p<0.05), NDF (p<0.001 and 0.05) and NFE (p<0.05) contents. However, there were decreases in leaf crude protein content (CP, quadratic, p<0.001) and stalk and whole plant EE content (linear, p<0.001), CP (quadratic, p<0.05) and ash (quadratic, p<0.05) contents. Digestibility of DM and TDN, and DE and ME value in leaves were not affected by increasing shoot height, but these measures linearly decreased (p<0.001) in stalk and whole plant. In Experiment 2, the hay had higher DM and CP concentrations, but lower EE concentration than the silage. Essential oil (EO) content in wormwood silage (0.49 g/100 g DM) was higher (p<0.05) than that in wormwood hay (0.32 g/100 g DM). Wormwood hay contained 25 essentail oils (EO) including camphor (10.4 g/100 g), 1-borneol (11.6 g/100 g) and caryophyllene oxide (27.7 g/100 g), and wormwood silage had 26 EO constituents including 3-cyclohexen-1-ol (8.1 g/100 g), trans-caryophyllene (8.6 g/100 g) and ${\gamma}$-selinene (16.8 g/100 g). It is concluded that the most ideal shoot height for harvesting wormwood is 60 cm based on the optimization of DM yield and nutritive value. Wormwood silage had a greater quantity and array of EO than wormwood hay.

Analyzing of the Essential Oil Chemical Constituents in Artemisia lavandulaefolia and its Pharmacological Property on Antibacterial Activity

  • Kim, Kyong-Heon;Kim, Baek-Cheol;Lee, Hwa-Jung;Jeong, Seung-Il;Kim, Hong-Jun;Ju, Young-Sung
    • The Journal of Korean Medicine Ophthalmology and Otolaryngology and Dermatology
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    • v.17 no.3
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    • pp.26-32
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    • 2004
  • Objective: The aim of this work is to investigate the antibacterial activity of the essential oil obtained from Artemisia lavandulaefolia (A. lavandulaefolia), as the development of microbial resistance to antibiotics make it essential to constantly look for new and active compounds effective against pathogenic bacteria. Method: The aerial parts of A. lavandulaefolia (1 kg) were subjected to steam distillation for 3 h, using a modified Clevenger type apparatus in order to obtain essential oil. Diethyl ether was the extracting solvent kept at 25?. The essential oil were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The essential oil and the composition were tested for antimicrobial activities against 15 different genera of oral bacteria. Ninety-nine compounds accounting for 94.74$\%$</TEX> of the oil were identified. The main compounds in the oil were 1,8-cineole (5.63$\%$), yomogi alcohol (4.49$\%$), camphor (4.92$\%$), a-caryophyllene (16.10$\%$), trans-a-famesene (5.09$\%$), a-terpineol (3.91$\%$), borneol (5.27$\%$), cis-chrysanthenol (6.98$\%$), and a-humulene oxide (3.33$\%$). The essential oil and its compounds were tested for antimicrobial activity against 10 different genera of oral bacteria. Conclusion: The essential oil of A. lavandulaefolia exhibited considerable inhibitory effects against all obligate anaerobic bacteria (MICs, 0.025 - 0.05 ㎎/ml) tested, while their major compounds demonstrated various degrees of growth inhibition

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Artemisia fukudo essential oil attenuates LPS-induced inflammation by suppressing NF-${\kappa}B$ and MAPK activation in RAW 264.7 cells

  • Yoon, Weon-Jong
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2010.10a
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    • pp.13-13
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    • 2010
  • In the present study, the chemical constituents of Artemisia fukudo essential oil (AFE) were investigated using GC-MS. The major constituents were ${\alpha}$-thujone (40.28%), ${\beta}$-thujone (12.69%), camphor (6.95%) and caryophyllene (6.01%). We also examined the effects of AFE on the production of nitric oxide (NO), prostaglandin $E_2$ ($PGE_2$), tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$), interleukin-IL-$1{\beta}$ (IL-$1{\beta}$), and IL-6 in lipopolysaccharide (LPS)-activated RAW 264.7 cells. Western blotting and RT-PCR analyses indicated that AFE has potent dose-dependent inhibitory effects on pro-inflammatory cytokines and mediators. We investigated the mechanism by which AFE inhibits NO and $PGE_2$ by examining the level of nuclear factor-${\kappa}B$ (NF-${\kappa}B$: p50 and p65) activation within the mitogen-activated protein kinase (MAPK: ERK, JNK and p38) pathway, which is an inflammation induced signal pathway in RAW 264.7 cells. AFE inhibited LPS-induced ERK, JNK and p38 phosphorylation. Furthermore, AFE inhibited the LPS-induced phosphorylation and degradation of $I{\kappa}B-{\alpha}$, which is required for the nuclear translocations of the p50 and p65 NF-${\kappa}B$ subunits in RAW 264.7 cells. Our results suggest that AFE might exert an anti-inflammatory effect by inhibiting the expression of pro-inflammatory cytokines. Such an effect is mediated by a blocking of NF-${\kappa}B$ activation which consequently inhibits the generation of inflammatory mediators in RAW 264.7 cells. AFE may be useful for treating inflammatory diseases.

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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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    • 2016.05a
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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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