• Title/Summary/Keyword: terpinen-4-ol

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Qualitative, Quantitative Analysis and Chiral Characterization of the Essential Oils of Juniperus phoenicea L. and Juniperus oxycedrus L.

  • Dahmane, Dahmane;Dahmane, Fahima Abdellatif;Dob, Tahar;Chelghoum, Chaabane
    • Natural Product Sciences
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    • v.26 no.1
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    • pp.97-107
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    • 2020
  • Isolation of oils from leaves of Juniperus phoenicea and Juniperus oxycedrus was obtained by steam distillation extraction method. The compositions of essential oils (EOs) were studied by means of GC-MS and GC-FID, using the internal standard method and relative response factors. Around ninety eight compounds were determined in total, representing 98.25 g/100 g of EO of J. phoenicea and 98.48 g/100 g of EO of J. oxycedrus, respectively. The volatile leaf oils were dominated by the terpenic hydrocarbon fractions (79.87 g/100 g) and (61.27 g/100 g) characterized by high contents of α-pinene (64.6 g/100 g) and (54.0 g/100 g) in J. phoenicea and J. oxycedrus, respectively, as the main component. Also, the enantiomeric distribution of α-pinene, sabinene, camphene, δ-3-carene, β-pinene, limonene, linalool, terpinen-4-ol, bornyl acetate, and borneol in both oils is presented for the first time.

Analysis of the Content of Hesperidin and Essential Oils from the Peels of Various Citrus Species (진피류(陳皮類) 한약재의 Hesperidin과 정유성분 비교)

  • Ham, In-Hye;Jung, Eui-Dong;Lee, Kyung-Jin;Lee, Je-Hyun;Bu, Young-Min;Kim, Ho-Cheol;Choi, Ho-Young
    • The Korea Journal of Herbology
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    • v.23 no.4
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    • pp.159-170
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    • 2008
  • Objectives: This study was carried out to evaluate the quality of the peels of various Citrus species. Method: The contents of hesperidin from fruit peels used as Citri Pericarpium such as C. natsudaidai, C. grandis, C. unshiu, and C. sunki, were analyzed by HP-TLC, HPLC, and essential oils of those were analyzed by GC/MS. Results: HPLC analysis showed that the hesperidin from the peel of C. unshiu and C. reticulata was satisfied the standard of Korean Pharmacopoeia. The essential oil was analyzed by GC/MS. As a result, limonene, furfural, 5-methyl-2-furfural, linalool oxide(cis), linalool oxide(trans), terpinen-4-ol, $(-)-{\alpha}$-terpineol, germacrene D, 4-methyl-2,6-di-tert-butylphenol was detected in all 4 kinds of Citrus species. Conclusions: As a result of chemotaxonomical similarity analysis with essential oils, the peels of C. natsudaidai and C. grandis are closely related, while C. unshiu is distantly related to the others.

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Studies on Measuring Volatile Terpenoids in Carrots Using the Direct Headspace Sampling Method (Direct Headspace Sampling 방법을 이용한 당근의 휘발성 Terpenoids 분석에 관한 연구)

  • Park, Yong;Ryu, Jang-Bal;Park, Sang-Gyu;Park, Shin
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.536-540
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    • 1997
  • Volatile terpenoids of carrots were measured by the direct headspace sampling method(DHS) with gas chromatography as a study for the breeding of high quality carrots. Using this method, 7 terpenoids such as ${\alpha}-pinene$, ${\beta}-pinene$, ${\beta}-myrcene$, ${\alpha}-terpinene$, limonene, ${\gamma}-terpinene$, and terpinolene were clearly separated. However ${\alpha}-phellandrene$ was not clearly separated from ${\beta}-myrcene$. In addition to this, higher boiling point compounds such as terpinen-4-ol, bornyl acetate, and ${\alpha}-bisbolol$ were not found. The coefficients of $determination(r^2)$ for the 7 terpenoids were higher than 0.99 and the standard curves were highly significant. Four replicated samples using this method demonstrated great reproducibility; the coefficidnt of variation (C.V.) for ${\alpha}-pinene$, ${\beta}-pinene$, ${\beta}-myrcene$, limonene, ${\gamma}-terpinene$, terpinolene, and total terpenoids were 6.8, 6.8, 8.4, 7.1, 3.8, 10.1, 7.1%. Sixty five carrot cultivars breeded worldwide were evaluated for the 7 terpenoids and total terpenoids; the range for ${\alpha}-pinene$, ${\beta}-pinene$, ${\beta}-myrcene$, ${\alpha}-terpinene$, limonene, ${\gamma}-terpinene$, terpinolene, and total terpenoids were $0.28{\sim}2.48\;ppm$, $0.35{\sim}1.87\;ppm$, $0.56{\sim}1.51\;ppm$, 0 ppm, $0.59{\sim}1.84\;ppm$, $0.87{\sim}3.33\;ppm$, $5.15{\sim}35.81\;ppm$, and $9.07{\sim}42.30\;ppm$, respectively. Big differences in each terpenoid and total terpenoids were found among cultivars. On the total terpenoids of the 65 cultivars, 5 cultivars(7.7%) contained less than 10 ppm, 15 cultivars (23.1%) $10{\sim}11.99\;ppm$, 14 cultivars(21.5%) $12{\sim}13.99\;ppm$, 9 cultivars(13.8%) $14{\sim}15.99\;ppm$, 10 cultivars(15.4%) $16{\sim}17.99\;ppm$, 4 cultivars(6.2%) $18{\sim}19.99\;ppm$, 5 cultivars(7.7%) $20{\sim}29.99\;ppm$, and 3 cultivars(4.6%) were higher than 30 ppm. Generally, cultivars developed in Japan contained less total terpenoids than cultivars developed in Europe and America.

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Changes of VOCs Emission on Pine (Pinus Rigida) Board by Finishing with Different Coating Types (도장처리에 따른 소나무 판재의 휘발성유기화합물 방출특성 변화)

  • Park, Sang-Bum;Lee, Min;Lee, Sang-Min;Kang, Yeong-Seok
    • Journal of the Korea Furniture Society
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    • v.26 no.2
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    • pp.122-129
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    • 2015
  • In previous study, VOC emission characteristics of coating materials for wood finishing were conducted and results showed that eco-friendly products has about 15~46% lower TVOC emission than typical products. In this study, lower TVOC emitted coating materials were applied on pine and then changes of VOC emission characteristics from pine with treatments were determined. Non-treated pine emitted $604.7{\mu}g/m^2h$ of TVOC that contained 66% of NVOC ($399.7{\mu}g/m^2h$). However, $V_2$ finished pine showed no NVOC emission rather than AVOC emission that consisted of Toluene, Ethylbenzene, m,p-Xylene, o-Xylene, 1,2,4- Trimethylbenzene. All coating materials inhibited ${\alpha}$-Pinene emission which originally from pine, but waterborne stain ($W_1$ and $W_3$) showed lower disruption of that emission. Moreover, $W_3$/wood showed higher NVOC emission such as ${\alpha}$-Terpinol, Terpinen-4-ol which are known as antioxidant substrates. Based on results, VOC emission characteristic of pine was significantly affected by coating materials with negatively in terms of ${\alpha}$-Pinene emission or positively in terms of NVOC emission. Therefore, coating material is important factor for indoor air quality when it would apply on wood products. For the future study, VOC emission characteristic of coated wood will be conducted continuously.

Studies on the Zanthoxylum piperitum $D_E$ $C_{ANDOLIE}$ - 1. Pungent principles and Essential oil composition - (천초(川椒)에 관(關)한 연구(硏究) - 1. 신미성분(辛味成分)과 정유성분(精油成分) -)

  • Jung, Hyun-Sook
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.16 no.2
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    • pp.123-127
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    • 1987
  • The Pungent principles and Essential oil compositions of Zanthoxylum piperitum $D_E$ $C_{ANDOLIE}$(peel, barb) were analysed by HPLC and GC, respectively. Total Pungent principle contents of peels were about as 12 times as those of barks. The Sanshool I, Sanshool IV, Sanshool III and Sanshoo V were the major Pungent principles in the peels and barks. Besides, several Unknown Pungent principles were discovered in the peels and barks, too. Total Essential oil contents of peels were higher than those of barks at the ratio of 1.8 % to 0.5%. The Cineol+Limonene(37.7%) were the main Essential oil compositions in the peels, while ${\alpha}-Terpineol(16.5%)$ and Pinene(15.5%) were the major portion in the barks. The Essential oil of peels and barks were composed Pinen, Myrcene, Cineol+Limonene, Linalool, Isopulegol, Terpinen-4-ol, ${\alpha}-Terpineol$ and Piperitone. Besides, seven Unknown compositions were discovered, too.

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In Vitro and In Vivo Anti-Tobacco Mosaic Virus Activities of Essential Oils and Individual Compounds

  • Lu, Min;Han, Zhiqiang;Xu, Yun;Yao, Lei
    • Journal of Microbiology and Biotechnology
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    • v.23 no.6
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    • pp.771-778
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    • 2013
  • Essential oils are increasingly of interest for use as novel drugs acting as antimicrobial and antiviral agents. In the present study, we report the in vitro antiviral activities of 29 essential oils, extracted from Chinese indigenous aromatic plants, against the tobacco mosaic virus (TMV). Of these essential oils, those oils from ginger, lemon, tea tree, tangerine peel, artemisia, and lemongrass effected a more than 50% inhibition of TMV at 100 ${\mu}g/ml$. In addition, the mode of antiviral action of the active essential oils was also determined. Essential oils isolated from artemisia and lemongrass possessed potent inactivation and curative effects in vivo and had a directly passivating effect on TMV infection in a dose-dependent manner. However, all other active essential oils exhibited a moderate protective effect in vivo. The chemical constitutions of the essential oils from ginger, lemon, tea tree, tangerine peel, artemisia, and lemongrass were identified by gas chromatography and gas chromatography-mass spectrometry. The major components of these essential oils were ${\alpha}$-zingiberene (35.21%), limonene (76.25%), terpinen-4-ol (41.20%), limonene (80.95%), 1,8-cineole (27.45%), and terpinolene (10.67%). The curative effects of 10 individual compounds from the active essential oils on TMV infection were also examined in vivo. The compounds from citronellal, limonene, 1,8-cineole, and ${\alpha}$-zingiberene effected a more than 40% inhibition rate for TMV infection, and the other compounds demonstrated moderate activities at 320 ${\mu}g/ml$ in vivo. There results indicate that the essential oils isolated from artemisia and lemongrass, and the individual compound citronellal, have the potential to be used as an effective alternative for the treatment of tobacco plants infected with TMV under greenhouse conditions.

Effects of Drying Conditions on the Profile of Volatile Terpenoid and Colour of Schizandra Fruit(Schizandra Chinensis fructus) (건조 조건이 오미자의 휘발성 terpene류 및 색도에 미치는 영향)

  • Kim, Yun-Je;Lee, Young-Guen;Choi, Young-Whan;Kim, Yong-Chul
    • Journal of Life Science
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    • v.18 no.8
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    • pp.1066-1071
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    • 2008
  • Schizandra fruit (Schizandra chinensis fructus) were dried by three processes, $50^{\circ}C$ (50HAD), $70^{\circ}C$ hot air (70HAD) and freeze drying process (FRD). Terpenoid were collected by SDE(Simultaneous Steam Distillation-Extraction) and followed by GC-MSD analysis. Also colour profile of each dried samples were measured by Hunter colorimeter. From fresh schizandra fruit, were detected 15 kinds of monoterpene, 28 kinds of sesquiterpene and 7 kinds of terpene alcohol. Myrcene(56.97 ${\mu}g/g$) and ${\gamma}$-terpinene(58.49 ${\mu}g/g$) were the major monoterpenes, ${\beta}$-elemene(120.16 ${\mu}g/g$), ${\alpha}$-bergamotene (103.45 ${\mu}g/g$), ${\gamma}$-selinene (75.97 ${\mu}g/g$), ${\beta}$-cubebene(66.69 ${\mu}g/g$), aristolene (51.25 ${\mu}g/g$) and ${\alpha}$-ylangene(28.06 ${\mu}g/g$) were the sesquiterpenes, and T-muurolol (96.45 ${\mu}g/g$) and terpinen-4-ol(46.02 ${\mu}g/g$) were the terpene alcohols. The dried samples lost more than half of terpenoid content of fresh schizandra fruit during early stage of drying process, and then the level of terpenoid content was not significantly changed. The content of sesquiterpenes appeared to increase until 6 day of FRD. The amount of residual terpene alcohols contained in schizandra fruit dried by FRD was more than those remained after drying by other processes, and schizandra fruit dried by 70HAD exhibited the least residual terpene alcohols. Brightness parameter $L^{\ast}$ decreased with the rise in the level of drying temperature, to which redness parameter $a^{\ast}$ and yellowness $b^{\ast}$ appeared to be similar.

Emission Characteristics of Volatile Organic Compounds by Humidifier with Using Hinoki Cypress Extracts (편백잎추출수의 실내 가습시 휘발성유기화합물 방출 특성)

  • Lee, Min;Park, Sang-Bum;Lee, Sang-Min;Lee, Hee-Young;Kil, Duck-Han
    • Journal of the Korean Wood Science and Technology
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    • v.42 no.6
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    • pp.747-757
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    • 2014
  • Since the air contamination by air pollutants from indoor construction materials and daily supplies has been increased in recent decades, the public interest of using environmentally friendly products and improving indoor air quality also attracted much attention. As known as effects of phytoncide, it has been used in construction materials and daily supplies with various method. In this study, hinoki cypress (Chamaecyparis obtusa) was used because of its high contents of phytoncide. The leaves of hinoki cypress (C. obtusa), which generated by pruning, were extracted by steam distillation, and then used as humidification water source. Volatile organic compound (VOC) from C. obtusa were characterized by GC-MS (Gas chromatograph-Mass spectrophotometry) in order to evaluate effects and risks of using C. obtusa extracts. Total 86 types and 116 types of VOC were detected from distilled water (DI water) and C. obtusa extracts, respectively. Aromatic compounds (DI water: 13 types, 53%; C. obtusa extracts: 13 types, 38%) and terpenoids (DI water: 16 types, 23%; C. obtusa extracts: 23 types, 33%) were detected more diverse types and higher amount than other compound categories. No additional aromatic compounds were found from C. obtusa extracts, so C. obtusa extracts did not affect on aromatic compounds emission. However, in terpenoids, total amount of emission from C. obtusa extracts increased to 33% from 23% (DI water) and 7 more types of compounds were found from C. obtusa extracts. Especially, from C. obtusa extracts, terpinen-4-ol was emitted 71 times higher than DI water. During the humidification with C. obtusa extracts, emitted terpenoid compounds were well known for higher anti-bacterial, anti-insect, and anti-septic functions, but also these had anti-hypertensive and anti-cancer activities. Therefore, terpenoids from C. obtusa extracts can help to improve public health by using humidifier.

Phytochemical Analysis and Anti-cancer Investigation of Boswellia Serrata Bioactive Constituents In Vitro

  • Ahmed, Hanaa H;Abd-Rabou, Ahmed A;Hassan, Amal Z;Kotob, Soheir E
    • Asian Pacific Journal of Cancer Prevention
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    • v.16 no.16
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    • pp.7179-7188
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    • 2015
  • Cancer is a major health obstacle around the world, with hepatocellular carcinoma (HCC) and colorectal cancer (CRC) as major causes of morbidity and mortality. Nowadays, there isgrowing interest in the therapeutic use of natural products for HCC and CRC, owing to the anticancer activity of their bioactive constituents. Boswellia serrata oleo gum resin has long been used in Ayurvedic and traditional Chinese medicine to alleviate a variety of health problems such as inflammatory and arthritic diseases. The current study aimed to identify and explore the in vitro anticancer effect of B. Serrata bioactive constituents on HepG2 and HCT 116 cell lines. Phytochemical analysis of volatile oils of B. Serrata oleo gum resin was carried out using gas chromatography-mass spectrometry (GC/MS). Oleo-gum-resin of B. Serrata was then successively extracted with petroleum ether (extract 1) and methanol (extract 2). Gas-liquid chromatography (GLC) analysis of the lipoidal matter was also performed. In addition, a methanol extract of B. Serrata oleo gum resin was phytochemically studied using column chromatography (CC) and thin layer chromatography (TLC) to obtain four fractions (I, II, III and IV). Sephadex columns were used to isolate ${\beta}$-boswellic acid and identification of the pure compound was done using UV, mass spectra, $^1H$ NMR and $^{13}C$ NMR analysis. Total extracts, fractions and volatile oils of B. Serrata oleo-gum resin were subsequently applied to HCC cells (HepG2 cell line) and CRC cells (HCT 116 cell line) to assess their cytotoxic effects. GLC analysis of the lipoidal matter resulted in identification of tricosane (75.32%) as a major compound with the presence of cholesterol, stigmasterol and ${\beta}$-sitosterol. Twenty two fatty acids were identified of which saturated fatty acids represented 25.6% and unsaturated fatty acids 74.4% of the total saponifiable fraction. GC/MS analysis of three chromatographic fractions (I,II and III) of B. Serrata oleo gum resin revealed the presence of pent-2-ene-1,4-dione, 2-methyl- levulinic acid methyl ester, 3,5- dimethyl- 1-hexane, methyl-1-methylpentadecanoate, 1,1- dimethoxy cyclohexane, 1-methoxy-4-(1-propenyl)benzene and 17a-hydroxy-17a-cyano, preg-4-en-3-one. GC/MS analysis of volatile oils of B. Serrata oleo gum resin revealed the presence of sabinene (19.11%), terpinen-4-ol (14.64%) and terpinyl acetate (13.01%) as major constituents. The anti-cancer effect of two extracts (1 and 2) and four fractions (I, II, III and IV) as well as volatile oils of B. Serrata oleo gum resin on HepG2 and HCT 116 cell lines was investigated using SRB assay. Regarding HepG2 cell line, extracts 1 and 2 elicited the most pronounced cytotoxic activity with $IC_{50}$ values equal 1.58 and $5.82{\mu}g/mL$ at 48 h, respectively which were comparable to doxorubicin with an $IC_{50}$ equal $4.68{\mu}g/mL$ at 48 h. With respect to HCT 116 cells, extracts 1 and 2 exhibited the most obvious cytotoxic effect; with $IC_{50}$ values equal 0.12 and $6.59{\mu}g/mL$ at 48 h, respectively which were comparable to 5-fluorouracil with an $IC_{50}$ equal $3.43{\mu}g/mL$ at 48 h. In conclusion, total extracts, fractions and volatile oils of B. Serrata oleo gum resin proved their usefulness as cytotoxic mediators against HepG2 and HCT 116 cell lines with different potentiality (extracts > fractions > volatile oil). In the two studied cell lines the cytotoxic acivity of each of extract 1 and 2 was comparable to doxorubicin and 5-fluorouracil, respectively. Extensive in vivo research is warranted to explore the precise molecular mechanisms of these bioactive natural products in cytotoxicity against HCC and CRC cells.