• Title/Summary/Keyword: caryophyllene oxide

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Composition of the Essential Oil of Chrysanthemum sibiricum, and Cytotoxic Properties

  • Lee, Kyung-Tae;Choi, Jong-Won;Park, Jong-Hee;Jung, Won-Tae;Jung, Hyun-Ju;Park, Hee-Juhn
    • Natural Product Sciences
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    • v.8 no.4
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    • pp.133-136
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    • 2002
  • GC-MS data on the volatile oil (CS-oil) of Chrysanthemum sibiricum herbs led to the identification of 2-methoxythioanisol, (+)-camphor, geraniol, citral, thymol, eugenol, ${\beta}-caryophyllene$ oxide, ${\beta}-caryophyllene$, ${\beta}-eudesmol$, juniper camphor together with an unknown substance using the mass spectral library and literature data. CS-oil exhibited significant cytotoxicities on HL-60 $(IC_{50}\;12.5\;{\mu}g/ml)$ cell and mild on HepG-2 cell $(IC_{50}\;102.4\;{\mu}g/ml)$, though the antioxidant ability was found not to be potent $(IC_{50}\;97.2\;{\mu}g/ml)$. However, the component eugenol showed potent antioxidant ability but mild cytotoxicity. Methyleugenol with no phenolic OH showed less potent cytotoxic and antioxidative properties than eugenol suggesting that phenolic OH plays an important role for the cytotoxic and antioxidant abilities. The oil-pretreatment prevented lipid peroxidation induced by bromobenzene in the rat. Therefore, it was demonstrated that CS-oil could be a cytotoxic agent with antioxidant properties.

Flavoral Essential Oil Components in the Stems of Agastache rugosa for Aromatherapy (아로마테라피용 배초향(Agastache rugosa) 줄기의 방향성 정유 성분)

  • Kim, Jeong-Mee
    • Journal of the Korean Society of Food Culture
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    • v.36 no.3
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    • pp.317-324
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    • 2021
  • This study was carried out to investigate the flavoral essential oil components in the stems of Agastache rugosa. These components were analyzed using gas chromatography-mass selective detector (GC-MSD). The stems of Agastache rugosa were contained alcohols, aldehydes, ketones, fatty acid esters, and terpenoids. The peak area (%) of estragole was highest among its oil components and the next were pulegone and menthone. The terpenoid alcohols found were 1-octen-3-ol, chavicol, spatulenol, 3-hexen-1-ol, 2-cyclohexen-1-ol, methyl eugenol, and octaethyllene glycol. The stems also contained ketones such as pulegone, menthone, cis-isopulegone, 2-cyclohexene-1-one, 3-octanone, 1-cyclohexanone, isoindole-1-one, t-ionone, inden-2-one, as well as the aldehydes of 4-methoxycinnam and benzaldehyde. The following esters were also detected 1-isopulegone-3-yl acetate, caryophyllene oxide, acetate and benzendicarboxylic acid ester. The terpenoids in the stems were identified as caryophyllene, limonene, cyclohexasiloxane-D, germacrene-D, anethole, cadinene, muurolene, and bourbonene. Overall Agastache rugosa contained several functional oil components including phenylpropanoids and terpenoids as flavoral essential oil components for natural aromatherapy.

The Quantitative Changes of Major Compounds from Aster koraiensis Nakai Essential Oil by Harvesting Time (수확 시기에 따른 벌개미취 정유의 주요 화합물 함량 변화)

  • Choi, Hyang-Sook
    • The Korean Journal of Food And Nutrition
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    • v.27 no.2
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    • pp.194-202
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    • 2014
  • This study investigates the chemical compositions of Aster koraiensis Nakai essential oils and the quantitative changes of major terpene compounds according to various harvesting times. The essential oils obtained by hydrodistillation from the aerial parts of Aster koraiensis Nakai are being analyzed by GC and GC-MS. The essential oil compositions of Aster koraiensis Nakai are characterized byhigher contents of sesquiterpene compounds. Ninety-seven volatile flavor compounds are being identified in the essential oils from Aster koraiensis Nakai harvested in 2010, and caryophyllene oxide (8.38%), aristolene (7.08%), epiglobulol (5.57%), and ethyl furanone (4.73%) are the most abundant compounds. Ninety-five compounds are identified in the essential oils from the plants harvested in 2011, and aristolene (11.56%), calarene (9.33%), phytol (8.28%), ethyl furanone (7.63%), and epiglobulol (7.18%) are the most abundant compounds. Ninety-five compounds are being identified in the essential oils from the plants harvested in 2012, and calarene (15.3%), aristolene (14.24%), ethyl furanone (7.21%), phytol (6.98%) are the major compounds. The contents of aristolene, ${\alpha}$-caryophyllene, ${\alpha}$-muurolene, ${\alpha}$-calacorene, aromadendrene oxide, and calarene increase significantly from 2010 to 2012. The contents of ${\alpha}$-cubebene, isocaryophyllene, and diepi-${\alpha}$-cedrene epoxide decrease significantly from 2010 to 2012. The quantitative changes of aristolene and calarene according to harvesting time can be served as a quality index of the Aster koraiensis Nakai essential oils.

Analysis of aroma components from flower tea of German chamomile and Chrysanthemum boreale Makino (국화과 허브류인 수입산 캐모마일차와 국내산 국화차의 향기성분 비교)

  • Im, Sung-Im;Bae, Jung-Eun;Choi, Sung-Hee
    • Korean journal of food and cookery science
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    • v.22 no.6 s.96
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    • pp.768-773
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    • 2006
  • The aroma components of german chamomile tea in Europe and kukwha (Chrysanthemum boreale Makino) tea in Korea belonging to genus chrysanthemum were analyzed and compared. The volatile components of chamomile tea and kukwha tea were collected by a simultaneous steam distillation-solvent extraction method (SDE). The extracted components were analyzed gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Forty-six compounds, including cubebene(14.59%), ${\beta}$-elememe(4.88%) and ${\delta}$-cadinol(1.54%) were identified in chamomile tea. Forty-five compounds including santalol(6.25%), bomyl acetate(3.47%), farnesene(3.37%), 1,8-nonadiene (2.80%), caryophyllene oxide(2.77%) and thymol (2.16%) were identified in kukwha tea. Twenty-two compounds including 4-terpineol, ${\alpha}$-terpineol, thymol, phenylacetaldehyde, V-terpinene were found in both samples.

Changes of Volatile Compounds in the Pericarp of Chopi (Zanthoxylum piperitum DC.) During Maturation (초피 과피의 성숙정도에 따른 향기성분의 변화)

  • ;;;;;;;;Ken C. Sink
    • Journal of Life Science
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    • v.13 no.2
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    • pp.206-213
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    • 2003
  • This study was conducted to estimate volatile compounds in pericarp of Zanthoxylum piperitum DC (Chopi). Chopi which harvested on lune 2, July 14 and September 11 in 2001 was dried at room temperature for one week. Fifty-two, 47, and 44 volatile compounds were analyzed with GC-MS in pericarp harvested on lune 2, July 14 and September 11, respectively. Eight terpenes including myrcene, ${\gamma}$-terpinene, $\alpha$-terpinolene, $\alpha$-phellandrene and $\beta$-caryophyllene were detected in pericarp harvested on tulle 2 and July 14, but not $\alpha$-phellandrene and $\beta$-caryophyllene in pericarp harvested on September 11. Thirteen alcohols or terpene alcohols including linalool L and citronellol were detected in pericarp harvested on lune 2, and added cis-linallol oxide and piperitol isomer in pericarp harvested on July 14 and September 11. Three aldehydes or terpene aldehydes were not affected by degree of maturation, but citronellal was increased in pericarp harvested on September 11. Five volatile compounds of ketones containing cryptone and piperitone were detected, and their concentration was changed during maturation. Six esters including lavandulyl acetate and $\alpha$-terpinenyl acetate were detected in pericarp harvested on lune 2, and [(E)-6,7-ephoxy-3,7-dimethyl-2-octenyl]ester of acetic acid was added in pericarp harvested on July 14 and September 11. Seven hydrocarbons including $\delta$-cadinene and neopentylidene cyclohexane were detected in pericarp harvested on June 2 and $\alpha$-muurolene was newly added in pericarp harvested on July 14 and September 11. We suggest that kinds and concentration of volatile compounds in pericarp were remarkably different from those in mature stage.

Emission Rates of Biogenic Volatile Organic Compounds (BVOCs) from Various Tree Species in Korea (I) (국내 수종별 BVOCs 방출량 (1))

  • Chang, Hanna;Son, Jounga;Je, Sun Mi;Oh, Chang-Young;Cho, Minseok;Kim, Juwan;Kim, Jaehyeon;Choi, Won-Sil;Lee, Young-Kyu
    • Journal of Korean Society of Forest Science
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    • v.110 no.4
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    • pp.543-553
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    • 2021
  • This research focused on the investigation of isoprene and terpene emissions from 30 major urban tree species. We conducted sampling using a specific dynamic enclosure system between August and September 2020. Seedlings less than three years old were enclosed in a chamber consisting of a 400 L transparent Tedlar bag. The air-flows from the chamber's outlet were sampled using Tenax-filled sorbent tubes in the presence of standard conditions (temperature: 30℃, PAR: 1,000 μmol/m2/sec). A thermal desorption GC/MS system was used to analyze 38 BVOC compounds (isoprene, monoterpene, sesquiterpene, oxygenated monoterpene, and sesquiterpene). Isoprene emitters included Phyllostachys bambusoides, Quercus serrata, Daphniphyllum macropodum, and Buxus Koreana. Monoterpene emitters included Pinus rigida, Acer pictum subsp. mono, Larix kaempfer, Magnolia denudata, Metasequoia glyptostroboides, Pinus koraiensis, Pinus densiflora, and Abies holophylla. The monoterpene emission profiles were dominated by α-pinene, myrcene, limonene, β-pinen, and sabinene, while caryophyllene and farnesene were the prominent sesquiterpenes. Predominant oxygenated monoterpene compounds were also discovered as pulegone, borneol, menthol, eucalyptol, and nerol, while caryophyllene oxide were the prominent oxygenated sesquiterpenes. Sesquiterpenes and oxygenated sesquiterpenes had relatively lower contributions for all species.

Di- and Sesqui-Terpenoids Isolated from the Pods of Sindora sumatrana and Their Potential to Inhibit Lipopolysaccharide-Induced Nitric Oxide Production

  • Jang, Dae-Sik;Min, Hye-Young;Jeong, Yeon-Hee;Lee, Sang-Kook;Seo, Eun-Kyoung
    • Archives of Pharmacal Research
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    • v.27 no.3
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    • pp.291-294
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    • 2004
  • Activity-guided fractionation of the n-hexane and ${CHCl_3}-soluble$ fractions of Sindora sumatrana using a bioassay based on the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production by inducible nitric oxide synthase (iNOS) in murine macrophage RAW 264.7 cells led to the isolation of the known compound, $(+)-7{\beta}-acetoxy-15,16-epoxy-3$, 13(16), 14-clero-datriene-18-oic acid (2) as an active constituent. In addition, a new trans-clerodane diterpenoid, (+)-2-oxokolavenic acid (1), together with six known compounds, (+)-3, 13-clerodadiene-16,15-olide-18-oic acid (3), $(+)-7{\beta}-acetoxy-3$,13-clerodadiene-16,15-olide-18-oic acid (4), $(+)-7{\beta}-acetoxy-16-hydroxy-3$,13-clerodadiene-16, 15-olide-18-oic acid (5), ${\beta}-caryophyllene$ oxide (6), $clovane-2{\beta},9{\beta}-diol (7),{\;}and{\;}caryolane-1,9{\beta}-diol$ (8) were isolated and found to be inactive. The structure of compound 1 was determined using physical and spectroscopic methods such as 1D and 2D-NMR experiments. The known compounds 2-8 were identified by the spectroscopic data and by comparison with the published values. Of eight isolates (1-8), only compound 2 exhibited an iNOS inhibitory activity with $IC_{50}$/ value of $51.6{\;}\mu\textrm{m}M$.

Volatile Flavor Components In a Mixed Tea of Pueraria Radix and Green Tea (녹차와 갈근을 혼합한 차의 휘발성 향기성분)

  • Jeon, Ju-Yeon;Choi, Sung-Hee
    • Journal of Life Science
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    • v.20 no.3
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    • pp.350-355
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    • 2010
  • This study was carried out in order to characterize the flavor of Pueraria radix-green tea. To make a new tea with good flavor and functional properties, Pueraria radix was mixed with green tea. Volatile flavor compounds of Pueraria radix-green tea were extracted by simultaneous distillations and extraction methods using a Likens and Nickerson's extraction apparatus. The concentrated extract was analyzed and identified by GC and GC-MS. Forty-nine compounds including $\beta$-selinene, $\beta$-caryophyllene, hexanal and nonanal were isolated and identified from Pueraria radix. Sixty-four compounds including nerolidol, linalool, linalool oxide and phenylethyl alcohol were isolated and identified from green tea. Eighty-two compounds including linalool, $\delta$-cadinene, limonene, $\beta$-caryophyllene and $\beta$-ionone were isolated and identified from Pueraria radix-green tea.

Herbicidal Activity of Natural Product Chrysophanic Acid (천연 물질 Chrysophanic acid의 제초 활성)

  • Jang, Hyun-Woo;Seo, Bo-Ram;Hwang, Hyun-Jin;Kim, Jae-Deog;Kim, Jin-Seog;Kim, Song-Mun;Chun, Jae-Chul;Choi, Jung-Sup
    • Korean Journal of Weed Science
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    • v.30 no.2
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    • pp.143-152
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    • 2010
  • Herbicidal characterisitcs of natural product chrysophanic acid were investigated in a greenhouse condition. At early- and middle-stage post-emergence treatments, several grasses and broadleaf weeds appeared to be very susceptible to chrysophanic acid. However, any significant herbicidal activity treated by pre-emergence did not occur at concentration ranges from 31.3 to 1,000 ug $mL^{-1}$. Herbicidal activity of chrysophanic acid estimated by visual injury for large crabgrass was much higher when applied at 7 to 14 days after seeding than at 21 and 28 days after seeding. By post-emergence treatment, chrysophanic acid caused very considerable phytotoxicity on several grasses and broadleaf crops. In herbicidal interaction experiments determined by Colby's method, the effect of chrysophanic acid and caryophyllene oxide tank-mixture showed very high synergistic activity. Although chrysophanic acid did not give any pre-emergence effect, herbicidal spectrum tended to be very wide and strong when treated by post-emergence. These results suggest that chrysophanic acid possesses a possible potential to develop as a natural herbicide.

Effect of $\gamma$-Irradiation of Volatile Organic Compounds of Houttuynia cordata Thunb. (방사선 조사에 의한 어성초의 휘발성 유기성분 변화)

  • Ryu, Keun-Young;Shim, Sung-Lye;Jung, Min-Seok;Jun, Sam-Nyeo;Jo, Cheor-Un;Song, Hyun-Pa;Kim, Kyong-Su;Kim, Youn-Soon
    • Food Science and Preservation
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    • v.15 no.3
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    • pp.411-420
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    • 2008
  • This study was performed to examine the effect of $\gamma$-irradiation on the volatile organic compounds in Houttuynia cordata Thunb.(H. cordata). 1be volatile compounds of non-irradiated and 10 kGy $\gamma$-irradiated H. cordata were isolated using SDE apparatus and analyzed by GC/MS. For each treatment the number of volatile compounds were detected at 83 and 85, respectively, 1be predominant functional groups of volatile organic compounds from H. cordata were identified as alcohols and ketones. H. cordata was mainly composed of hexahydrofarnesyl acetone (12.81 %), phytol, decanoic acid, dodecanoic acid, octadecanol, caryophyllene oxide, 2-undecanone and menthol. Houttuynum which is characteristic compound of H. cordata was found in all samples and there was no significant difference with irradiation doses. Consequently, $\gamma$-irradiation of H. cordata would be an effective process for sanitation and to increase extraction efficiency.