• Title/Summary/Keyword: Terpene

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Production of Mono-Hydroxylated Derivatives of Terpinen-4-ol by Bacterial CYP102A1 Enzymes

  • Jeong-Hoon Kim;Chan Mi Park;Hae Chan Jeong;Gyeong Han Jeong;Gun Su Cha;Sungbeom Lee;Chul-Ho Yun
    • Journal of Microbiology and Biotechnology
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    • v.34 no.3
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    • pp.725-734
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    • 2024
  • CYP102A1 from Bacillus megaterium is an important enzyme in biotechnology, because engineered CYP102A1 enzymes can react with diverse substrates and produce human cytochrome P450-like metabolites. Therefore, CYP102A1 can be applied to drug metabolite production. Terpinen-4-ol is a cyclic monoterpene and the primary component of essential tea tree oil. Terpinen-4-ol was known for therapeutic effects, including antibacterial, antifungal, antiviral, and anti-inflammatory. Because terpenes are natural compounds, examining novel terpenes and investigating the therapeutic effects of terpenes represent responses to social demands for eco-friendly compounds. In this study, we investigated the catalytic activity of engineered CYP102A1 on terpinen-4-ol. Among CYP102A1 mutants tested here, the R47L/F81I/F87V/E143G/L188Q/N213S/E267V mutant showed the highest activity to terpinen-4-ol. Two major metabolites of terpinen-4-ol were generated by engineered CYP102A1. Characterization of major metabolites was confirmed by liquid chromatography-mass spectrometry (LC-MS), gas chromatography-MS, and nuclear magnetic resonance spectroscopy (NMR). Based on the LC-MS results, the difference in mass-to-charge ratio of an ion (m/z) between terpinen-4-ol and its major metabolites was 16. One major metabolite was defined as 1,4-dihydroxyp-menth-2-ene by NMR. Given these results, we speculate that another major metabolite is also a mono-hydroxylated product. Taken together, we suggest that CYP102A1 can be applied to make novel terpene derivatives.

Relationship between NVOCs Concentration and Korean Red Pine (Pinus densiflora S. et Z.) Forest Environment in Spring Season (봄철 소나무숲의 NVOC 농도와 숲환경과의 상관관계)

  • Kim, GeonWoo;Kwon, ChiWon;Yeom, DongGeol;Joung, Dawou;Choi, Yoon Ho;Park, Bum-Jin
    • Journal of Korean Society of Forest Science
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    • v.103 no.3
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    • pp.483-489
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    • 2014
  • This study aimed at a scientific examination of the relationship between NVOCs concentration and the physical environment of red pine forest in spring season. Atmospheric NVOC samples in red pine forest was collected through five trials conducted from March to May 2013, using Tanax-Ta-charged disposable tubes and mini-pumps. At each trial, measurements were taken at three different points in daytime (sunrise, southing and sunset). For maximum accuracy, two tubes were used for each measurement at the same location, and the mean value was used for analysis. Compound analysis on the NVOC samples was done using the HS-SPME method and GC-MS. Analysis of the relationship between NVOC and the physical forest environment found higher concentrations of most substances, including ${\alpha}$-pinene and ${\beta}$-pinene, with higher temperature, dew point, and lower concentrations with higher wind velocity. The findings of this study offer scientific evidence which can inform the creation of 'healing forests' and 'recreational forests' as well as forest environment in general, helping to promote public health and recreational activities.

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.

Characterization and Expression Profile Analysis of a New cDNA Encoding Taxadiene Synthase from Taxus media

  • Kai, Guoyin;Zhao, Lingxia;Zhang, Lei;Li, Zhugang;Guo, Binhui;Zhao, Dongli;Sun, Xiaofen;Miao, Zhiqi;Tang, Kexuan
    • BMB Reports
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    • v.38 no.6
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    • pp.668-675
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    • 2005
  • A full-length cDNA encoding taxadiene synthase (designated as TmTXS), which catalyzes the first committed step in the Taxol biosynthetic pathway, was isolated from young leaves of Taxus media by rapid amplification of cDNA ends (RACE). The full-length cDNA of TmTXS had a 2586 bp open reading frame (ORF) encoding a protein of 862 amino acid residues. The deduced protein had isoelectric point (pI) of 5.32 and a calculated molecular weight of about 98 kDa, similar to previously cloned diterpene cyclases from other Taxus species such as T. brevifolia and T. chinenisis. Sequence comparison analysis showed that TmTXS had high similarity with other members of terpene synthase family of plant origin. Tissue expression pattern analysis revealed that TmTXS expressed strongly in leaves, weak in stems and no expression could be detected in fruits. This is the first report on the mRNA expression profile of genes encoding key enzymes involved in Taxol biosynthetic pathway in different tissues of Taxus plants. Phylogenetic tree analysis showed that TmTXS had closest relationship with taxadiene synthase from T. baccata followed by those from T. chinenisis and T. brevifolia. Expression profiles revealed by RT-PCR under different chemical elicitor treatments such as methyl jasmonate (MJ), silver nitrate (SN) and ammonium ceric sulphate (ACS) were also compared for the first time, and the results revealed that expression of TmTXS was all induced by the tested three treatments and the induction effect by MJ was the strongest, implying that TmTXS was high elicitor responsive.

Elucidation of the Biosynthetic Pathway of Vitamin B Groups and Potential Secondary Metabolite Gene Clusters Via Genome Analysis of a Marine Bacterium Pseudoruegeria sp. M32A2M

  • Cho, Sang-Hyeok;Lee, Eunju;Ko, So-Ra;Jin, Sangrak;Song, Yoseb;Ahn, Chi-Yong;Oh, Hee-Mock;Cho, Byung-Kwan;Cho, Suhyung
    • Journal of Microbiology and Biotechnology
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    • v.30 no.4
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    • pp.505-514
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    • 2020
  • The symbiotic nature of the relationship between algae and marine bacteria is well-studied among the complex microbial interactions. The mutual profit between algae and bacteria occurs via nutrient and vitamin exchange. It is necessary to analyze the genome sequence of a bacterium to predict its symbiotic relationships. In this study, the genome of a marine bacterium, Pseudoruegeria sp. M32A2M, isolated from the south-eastern isles (GeoJe-Do) of South Korea, was sequenced and analyzed. A draft genome (91 scaffolds) of 5.5 Mb with a DNA G+C content of 62.4% was obtained. In total, 5,101 features were identified from gene annotation, and 4,927 genes were assigned to functional proteins. We also identified transcription core proteins, RNA polymerase subunits, and sigma factors. In addition, full flagella-related gene clusters involving the flagellar body, motor, regulator, and other accessory compartments were detected even though the genus Pseudoruegeria is known to comprise non-motile bacteria. Examination of annotated KEGG pathways revealed that Pseudoruegeria sp. M32A2M has the metabolic pathways for all seven vitamin Bs, including thiamin (vitamin B1), biotin (vitamin B7), and cobalamin (vitamin B12), which are necessary for symbiosis with vitamin B auxotroph algae. We also identified gene clusters for seven secondary metabolites including ectoine, homoserine lactone, beta-lactone, terpene, lasso peptide, bacteriocin, and non-ribosomal proteins.

Investigation of Active Antifungal Compounds of Essential Oil from Chamaecyparis obtusa Against Dermatophytes, Microsporum canis and Trichophyton Mentagrophytes (피부사상균 Microsporum canis 및 Trichophyton mentagrophytes에 대한 편백정유의 항진균활성물질 탐색)

  • Park, Mi-Jin;Lee, Soo-Min;Gwak, Ki-Seob;Jeung, Eui-Bae;Chang, Je-Won;Choi, In-Gyu
    • Journal of the Korean Wood Science and Technology
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    • v.33 no.3 s.131
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    • pp.72-78
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    • 2005
  • The present study was conducted to evaluate the application of Chamaecyparis obtusa and to investigate potential utilization of essential oil from C. obtusa as plant-based medicine. The antifungal activity of essential oil from leaves and twigs of C. obtusa (Sieb. Et Zucc) was determined and the major components of active fractions against Microsporum canis (KCTC6591) and Trichophyton mentagrophytes (KCTC6077) were identified by GC/MS analysis. In treatment of essential oil from C. obtusa, the strain M. canis was more resistant than the other, T. mentagrophytes. In the agar diffusion assay, essential oil from C. obtusa inhibited hyphal growth of M. canis and T. mentagrophytes at the concentration of more than 5,000 ppm. The zones named B and C in the TLC assay of essential oil from C. obtusa showed antifungal activities. Among four sub-fractions of n-hexane extract from B and C zones, named as B-1, B-2, C-1 and C-2, the C-2 showed the highest antifungal activity. Instrumental GC/MS analysis for sub-fractions showed that a major component of C-1 was ${\alpha}$-terpineol as terpene alcohol, while C-2 contained sesquiterpenes such as elemol, cedrol and eudesmol.

Extraction and Biological Activities of Essential Oil from Thuja occidental Leaves (서양측백나무 잎으로부터 식물정유 추출 및 생리활성)

  • Seo, Weon-Taek;Yang, Jae-Kyung;Kang, Byung-Kuk;Park, Woo-Jin;Hong, Seong-Cheol;Kang, Young-Min;Jung, Hee-Young;Kim, Yong-Duck;Kang, Seung-Mi;Kim, Seon-Won;Choi, Myung-Suk
    • Korean Journal of Medicinal Crop Science
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    • v.11 no.5
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    • pp.364-370
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    • 2003
  • Essential oil of Thuja occidental leaves was extracted by steam distillation method, and chemical composition of essential oil was analyzed by GC-MS. The essential oil was tested to antimicrorbiaI activity against 28 test microorganisms and antioxident assay through DPPH free radical scaveging test and insecticidal activity by mosquito insecticide assay. The major constituents in the essential oil of T. occidental were monoterpene as d-isothujone, ${\alpha}-thujone$, camphor, L-fenchone, and hornyl acetate. The essential oil have broad antimicrobiaI activity, which showed strong antimicrobiaI activity for Streptococcus pyogenes as bacteria, Alternaria alternata, Aspergillus niger, Aspergillus oryzae, Saccharomyces cerevisiae, and Streptococcus mutans as fungi. The essential oil also showed DPPH free radical scavenging ability at concentration of $36\;{\mu}{\ell}/m{\ell}$. In spraying and fumigation tests, the essential oil had strong insecticidal activity against mosquito.

The Manufacture of Absorbents and Removal Characteristics of VOCs by Essential Oil and Photocatalyst (식물정유와 광촉매를 이용한 흡수제 제조 및 VOCs 제거특성에 관한 연구)

  • Jeong, Hae-Eun;Yang, Kyeong-Soon;Kang, Min-Kyoung;Cho, Joon-Hyung;Oh, Kwang-Joong
    • Clean Technology
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    • v.23 no.1
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    • pp.54-63
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    • 2017
  • Volatile organic compounds (VOCs) are widely used in both industrial and domestic activities. VOCs are one of the most unpleasant, frequently complaint-rousing factors of pollution around the world. It is now necessary to research and develop an alternative technology that could overcome the problems of the existing odor-control and VOC-eliminating techniques. In this study, essential oil and photocatalytic process was applied in the removal of benzene and toluene, typical VOCs in petrochemistry plant. therefore, this study conducted experiments on the selection of appropriate essential oil, photodegradation, hydroxyl radical generation capacity. The removal efficiency and reaction rate were performed to selecte the type and concentration of essential oil. As a result, removal efficiency of Hinoki Cypress oil was approximately 70% and reaction rate of Hinoki Cypress was high. The results of photolysis experiment, photocatalytic oxidation process showed that the decomposition efficiency of VOCs increased considerably with increasing UV lamp power. In addition, the conversion of VOCs was increased up to $0.1gL^{-1}$ photocatalysts. The hydroxyl radicals measure was performed to determine the ability to generate hydroxyl radicals. The analytical result showed that high $TiO_2$ concentration and lamp power was produced many hydroxyl radical. Experiments of the removal efficiency and reaction rate were performed using essential oil and photooxidation. As a result, the removal efficiency showed that the removal efficiency was increased high temperature and reaction time. The activation energy was calculated from the reaction rate equation at various temperature condition. Activation energy was approximately $18kJmol^{-1}$.

A Comparison of Volatile Compounds in Pine Extracts Obtained by Supercritical Fluid Extraction with Those by Simultaneous Steam Distillation and Solvent Extraction (초임계유체 추출과 SDE에 의한 솔 추출물의 휘발성분 비교)

  • Woo, Gaung-Yaul;Kim, Kong-Hwan;Lee, Mi-Jung;Lee, Yang-Bong;Yoon, Jung-Ro
    • Korean Journal of Food Science and Technology
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    • v.31 no.5
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    • pp.1268-1274
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    • 1999
  • Pine twigs with buds were cut into $2{\sim}3\;mm$ long pieces and about 18g was used for each experiment. Pressure and temperature ranges employed were $100{\sim}300\;bar$ and $35{\sim}55^{\circ}C$, respectively. Volatile compounds of extracts were isolated and identified by gas chromatography and mass selective detector. Twenty three compounds from the extracts were identified. Limonene and ${\beta}-pinene$ were found to be the major components with $32.6{\sim}43.4%$ being limonene. Extracts obtained by supercritical fluid extraction were lower in monoterpene and higher in oxygenated terpenoids than those by steam distillation and solvent extraction (SDE). Sensory evaluation showed that the pine flavor extracted using supercritical carbon dioxide was much better in quality than that of SDE. In conclusion, it was found out that supercritical fluid extraction can successfully be applied to extract high quality flavor from pine.

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The Forest Landscape Management of Therapeutic Forests by Visual Preference on the Simulation of Tree Density (임목밀도 시뮬레이션의 시각적 선호도를 통한 치유의 숲 산림경관 관리)

  • Lee, Yeon Hee;Kim, Ki Weon
    • Journal of Korean Society of Forest Science
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    • v.101 no.4
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    • pp.648-655
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    • 2012
  • This research is aimed at suggesting the reasonable guideline for managing tree density of a therapeutic forest to enhance the therapeutic efficiency. To obtain visually preferable tree density for 4 coniferous tree species; Pinus koraiensis, Chamaecyparis obtusa, Pinus densiflora, Larix kaempferi, the simulations of tree density according to the 3 diameter classes are used. 250 people participated in questionnaire and 239 people of them were analyzed. The tree density preferences of 4 tree species are as follows; Pinus koraiensis forest; tree density for trees with Diameter (DBH=D)<25 cm about 816/ha, tree density for trees with 25=D<40 about 400/ha and tree density for trees with 40=D about 277/ha. Chamaecyparis obtusa forest; tree density for trees with D<25 about 625/ha, tree density for trees with 25=D<40 about 625/ha and tree density for trees with 40=D about 400/ha. Pinus densiflora forest; tree density for trees with D<25 about 816/ha, tree density for trees with 25=D<40 about 625/ha and tree density for trees with 40=D about 400/ha. Larix kaempferi forest; tree density for trees with D<25 about 625/ha, tree density for trees with 25=D<40 about 625/ha and tree density for trees with 40=D about 277/ha.