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Effect of Trialkylborane on the Stereochemistry of Ketone Reduction with Lithium Borohydride

  • Nung-Min Yoon;Jin-Soon Cha;Won-Suh Park
    • Bulletin of the Korean Chemical Society
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    • v.4 no.1
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    • pp.14-17
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    • 1983
  • The effects of trialkylborane on the stereochemistry of ketone reduction with lithium borohydride were studied for the four representative ketones, namely 4-t-butylcyclohexanone, 2-methylcyclohexanone, norcamphor, and camphor. The presence of trialkylborane increased the yields of the less stable alcohols. For example, in the presence of tri-s-butylborane, 42 % yield of cis-4-t-butylcyclohexanol was observed whereas only 8 % yield with lithium borohydride alone in the reduction of 4-t-butylcyclohexanone. The in situ formation of lithium trialkylborohydride, by the hydride transfer from lithium trialkoxyborohydride to trialkylborane, was demonstrated as a possible mechanism for the catalytic effect of trialkylborane.

Essential Oil Conten and Composition of Aromatic Constituents in Some Medicinal Plant (몇가지 약용식물의 향기성분 조성 및 식물정유 함량)

  • 김상국
    • Korean Journal of Plant Resources
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    • v.11 no.3
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    • pp.279-282
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    • 1998
  • This expriment was carried out to get basic information on composition and yield of aromatic constituents in leaves of four medicinal plants, Angelica tenuissima, Chrysanthemum zawadskii. ssp. latilobum, Artemisia iwayomogi and Artemisia capillaris. Volatile aromatic constituents, 28 compounds in Angelica tenuissima were identified and 19 compounds were indentified in Chrysanthemum zawadskii ssp. latilobum. Volatile aromatic constituents, 23 compounds in Artemisia iwayomogi and Artemisia capillaris were identified. Major volatile aromatic consitiuents analyzed by GC/MS in four plants were $\alpha$-pinene, camphene, sabinene, cis-2-hexanol, and camphor etc. Content of essential oils in Angelica tenuissima, Chrysanthemum zawadskii ssp. latilobum, Artemisia iwayomogi and Artemisia capillaris were 0.014, 0.275, 0.785, and 0.452%, respectively. As a result, it was suggested that a medicinal plant, Artemisia iwayomogi, was worthy of using as a useful material of perfume.

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Comparision of Monoterpene in Ambient Air at Forest and Essential Oil (숲속 공기와 주변 우점수목 정유의 모노테르펜류 분포 비교)

  • Oh, Gil-Young;Seo, Yun-Gyu;Park, Gui-Hwan;Kim, Ik-San;Bae, Ju-Soon;Park, Song-In;Ha, Hun;Yang, Soo-In;Lee, Ji-Hun;Lee, Wan-Jin
    • Journal of Korean Society of Forest Science
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    • v.102 no.3
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    • pp.309-314
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    • 2013
  • The concentration of terpene (18 species) was measured from spring to fall in ambient air and essential oil at three different forests located in Jeollanamdo province. Sampling was conducted at 4-hour-interval a day of each season. In the ambient air, ${\alpha}$-pinene, ${\beta}$-pinene and 2-carene were the most abundant compounds throughout the sampling periods and areas. The highest three-season average concentration of total terpene was 2,597 pptv at Jeamsan(Mt.) in Boseong which was predominantly populated by Pinaceae. The seasonal averages were observed to peak during spring with their max at Palyeongsan(Mt.) in Goheung and Jeamsan(Mt.) in Boseong, and during fall at Woodland in Jangheung. Most of terpenes had diurnal variations with higher concentrations during the daytime, and lower during the nighttime. However in essential oil, the highest annual average concentration of total terpene was $798{\mu}g/dry-g$ at Goheung which was predominantly populated by Chamaecyparis obtusa. Also, the component proportion ratio showed different distribution between ambient air and essential oil. From the results of this study, we suggest that Chamaecyparis obtusa species is more useful, and younger tree is more economical than older one, and spring is the best season for lumbering in order to use essential oil.

Effect of Essential Oils and Paraffin Oil on Black Cutworm, Agrotis ipsilon (Lepidoptera: Noctuidae) (식물정유와 파라핀오일이 검거세미나방에 미치는 영향)

  • Lee, Dong Woon;Potter, D.A.
    • Weed & Turfgrass Science
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    • v.2 no.1
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    • pp.62-69
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    • 2013
  • The black cutworm, Agrotis ipsilon (Hufnagel), damages various cultivated crops and it can also be a serious pest of turfgrass, especially on golf courses. Essential oils have potential as alternative control agents for insect pests. Sixteen essential oils (anise, camphor, cinnamon, citronella, clove, fennel, geranium, lavender, lemongrass, linseed, neem, peppermint, pine, thyme, turpentine and tea saponin) and paraffin oil were assessed in the laboratory, the green house and field trials for their efficacy against black cutworms in turf. Treatment of potted cores of perennial ryegrass turf with anise, cinnamon, neem, paraffin or turpentine reduced black cutworm damage in a greenhouse trial, and in a similar trial, applying neem oil at 4000, 2000 and 1000 ppm resulted in 100, 100 and 64% mortality, respectively, of black cutworms. Weight of survivors at the 1000 ppm rate was 5- fold less than weight of comparably-aged controls. Neem oil (2000 ppm) reduced growth of black cutworms feeding on treated clippings. A high rate of neem oil followed by irrigation (0.1 L of 20000 ppm neem oil with 0.9 L watering/$m^2$) was more effective than a lower concentration (1 L of 2000 ppm neem oil/$m^2$) against $2^{nd}$ and $3^{rd}$ instars in potted turf cores and field plots, respectively. However, not even the aforementioned higher rate effectively controlled $4^{th}$ instars in the field.

Fumigant Toxicity of the Constituents of Coriander Oil, Coriandum sativum against Blattella germanica (바퀴에 대한 Coriander Oil (Coriandum sativum) 성분의 훈증효과)

  • Bae Jeong-Sook;Kim Gil-Hah
    • Korean journal of applied entomology
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    • v.44 no.1 s.138
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    • pp.37-41
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    • 2005
  • Essential oil of five plants were screened for fumigation toxicity against Blattella germanica male adults. Among them, coriander oil showed $100\%$ fumigation toxicity against B. germanica male adults at 20 and $10{\mu}{\ell}/{\ell}$ (air) dose, respectively. Through the constituent analysis using GC and GC/MS, we confirmed that main constituents of coriander oil were ${\alpha}$-pinene ($6.1\%$), camphene ($1.1\%$), ${\beta}$-pinene ($0.5\%$), ${\beta}$-myrcene ($0.8\%$), limonene ($2.5\%$), ${\gamma}$-terpinene ($4.5\%$), ${\rho}$-cymene ($1.8\%$), ${\alpha}$-terpinolene ($0.5\%$), camphor ($4.9\%$), linalool ($70.5\%$), ${\alpha}$-tepineol ($0.7\%$), geranyl acetate ($2.8\%$) and geraniol ($1.4\%$). Among them, ${\gamma}$-terpinene and geranyl acetate showed $100\%$ fumigation toxicity at $10{\mu}{\ell}/{\ell}$ (air) dose, respectively. It can be concluded that coriander oil is potential control agents against B. germanica.

Bioactive Constituents and Utilities of Artemisia sp. as Medicinal Herb and Foodstuff (쑥(艾)의 생리활성 물질과 이용)

  • 이성동;박홍현;김동원;방병호
    • The Korean Journal of Food And Nutrition
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    • v.13 no.5
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    • pp.490-505
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    • 2000
  • Mugwort (Artemisia sp.) abounds on hedgebank, waysides and grassy places in most part of Europe, Asia and Northern America. This herb has long been associated with witch-craft and magic as a protective charm. Mugwort has been a value as a foodstuff of relieving famine. Proximate composition of mugwort is similar to green vegetables, but it has high level in calcium, potassium and vitamin A content. For medicinal uses, the leaves are harvested twice in spring and autumn before the plant comes into flower and are dried for later uses. Aqueous or organic solvents extracts often have physiologically active constituents. Some extracts of mugwort include cineol, thujone, borneol, camphor, caryophyllene, coumarin, cubebene, pinene, linalool, absinthin etc. The dried leaves have traditionally been used as an antihelmintic, anti-inflammatory, antispasmodic, antitumor, hepatic stimulant, chologogue, emmenagogue, febrifuge, stomachic, tonic etc. Mugwort has been used the dried or green leaves as a flavoring and coloring agents for tea, cake. pastry, bread, noodle, alcoholic liquor, soap and hygienic band.

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Effects of Treatments on the Distribution of Volatiles in Artemisia princeps Pampan (쑥의 처리조건에 따른 휘발성 성분 변화)

  • Park, Min-Hee;Kim, Mi-Ja;Cho, Wan-Il;Chang, Pahn-Shick;Lee, Jae-Hwan
    • Korean Journal of Food Science and Technology
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    • v.41 no.5
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    • pp.587-591
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    • 2009
  • Volatiles in Artemisia princeps Pampan. cv. sajabal (sajabalssuk) and A. princeps Pampan. (ssuk) treated with different processing were analyzed using headspace-solid phase microextraction (HS-SPME)/gas chromatography- a mass selective detector (GC-MS). Sajabalssuk and ssuk were treated with steam distillation (SD) and freeze-dried/steam distillation (FD/SD) while controls were raw sajabalssuk and raw ssuk. Sajabalssuk had significantly more total volatiles than ssuk in control and FD/SD treated samples (p<0.05). Major volatiles in raw sajabalssuk were 2-hexenal, 1,8-cineol, trans-caryophyllene, and hexanal while those in raw ssuk were 1-hexanol, ${\beta}$-myrcene, limonene, and 2-hexenal, which implies that substantial lipid oxidation occurred in raw samples. Sajabalssuk with SD and FD/SD treatment had higher peak areas of 1,8-cineole, 4-terpineol, 1-octen-3-ol, and ${\alpha}$-terpineol while ssuk with SD and FD/SD treatment possessed 1,8-cineol, camphor, borneol, artemisia ketone, ${\alpha}$-thujone, and 1-octen-3-ol, which showed that steam distillation produced more volatiles from terpenoids than raw samples. Based on the results of HS-SPME/GC-MS, relative amounts of volatiles from lipid oxidation including 2-hexenal, hexanal, and 1-hexanol were reduced in sajabalssuk and ssuk with freeze-drying and/or steam distillation treatment.

Fumigant Toxicity of Essential Oils against Adults of Culex pipiens pallens (빨간집모기 성충(Culex pipiens pallens)에 대한 식물오일의 훈증효과)

  • Kang, Shin-Ho;Kim, Min-Ki;Seo, Dong-Kyu;Kim, Gil-Hah
    • The Korean Journal of Pesticide Science
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    • v.10 no.2
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    • pp.117-123
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    • 2006
  • Fumigant toxicity of 34 plant essential oils were tested against female adults of Culex pipiens pallens. Seven oils (basil, coriander, fennel, pennyroyal, peppermint, thyme red, thyme white) showed more than 60% mortality at 1 ${\mu}L\;L^{-1}$ air concentration and pennyroyal oil appeared to have the highest adulticidal activity. GC and GC-MS analysis of the seven essential oils and bioassay of their components revealed that pulegone (a major component of pennyroyal oil) and anethole (a major component of fennel and basil oil, $LD_{50}$, ${\mu}L\;L^{-1}$ air =0.49) showed higher adulticidal activities than others. In addition to the above two components, linalool ($LT_{50}$, min=0.91), camphor ($LT_{50}$, min=1.06), fenchone ($LT_{50}$, min=1.16), 1,8-cineole ($LT_{50}$, min=2.93), and geranyl acetate ($LT_{50}$, min=1.60) also showed higher adulticidal activity than empenthrin ($LT_{50}$, min=3.45).

Anti-Porcine Epidemic Diarrhea Virus (PEDV) Activity and Antimicrobial Activities of Artemisia dubia Essential Oil (참쑥(Artemisia dubia) 오일의 돼지 유행성 설사 바이러스(Porcine Epidemic Diarrhea Virus)에 대한 항바이러스 항균활성)

  • Kim, Jong-Im
    • Microbiology and Biotechnology Letters
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    • v.40 no.4
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    • pp.396-402
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    • 2012
  • The chemical composition, anti-porcine epidemic diarrhea virus (PEDV) activity and antimicrobial activity of Artemisia dubia essential oil were evaluated in this study. Fifty eight compounds from A. dubia essential oil were identified through analysis by gas chromatography-mass spectrometry (GC-MS). The major constituents of the oil were camphor (17.18 %), germacrene-D (15.70%), trans (${\beta}-$) racaryophyllene (6.79%), ene thujones (6.57%), 1, 8-cineole (5.94%) and camphene (5.08%). The essential oil was evaluated for antiviral activity against PEDV in Vero cells using a cytopathic effect (CPE) reduction method. The oils actively inhibited PEDV replication with a 50% inhibitory concentration ($IC_{50}$) of 43.7 ${\mu}^3/mL$. The 50% cytotoxicity concentration ($CC_{50}$) of the oils was over 100 ${\mu}/mL$ and the derived therapeutic index was >2.3. Similar analysis of the ribavirin revealed that they have a relatively weaker efficacy when compared to the oils. The antimicrobial activity of the essential oil against 5 microorganisms was evaluated by the disc diffusion method. The essential oil exhibited antimicrobial activity against 5 tested microorganisms with a clear zone of 8-22 mm. Among the tested microorganisms, Streptococcus pyogenes was the most sensitive and Candida albicans the least. Therefore, in can be concluded that essential oils of A. dubia may have interesting applications for microbial control or the control of PEDV-derived diseases.

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.