• 제목/요약/키워드: sesquiterpene compound

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산국으로부터 분리한 Sesquiterpene Lactones의 흰쥐 복수암에 대한 효과 (Effects of Sesquiterpene Lactones Isolated from Chrysanthemum boreale M. against Sarcoma180 Implanted in ICR Mice)

  • 남상해;최상도;최진상;장대식;최상욱;양민석
    • 한국식품영양과학회지
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    • 제26권1호
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    • pp.144-147
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    • 1997
  • 산국의 꽃으로부터 2종의 sesquiterpene lactones을 분리정제하였으며, 각각 Compound I 과 II로 명명하였으며, 이 두 물질을 Sarcoma180에 감염된 ICR mouse에 대하여 항암효과실험을 수행한 결과 Compound I과 II의 투여농도가 10mg/kg일 때 수명 연장효과가 각 각 143%, 134%로 나타났다. 또한 Compound I 과 II 를 1mg/kg 씩을 섞어서 투여하였을 때에 158%의 수명 연장효과가 나타났다

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우산나물 정유의 테르펜 화합물 분석 및 수확 연도에 따른 Sesquiterpene 화합물 변화 조사 (Analysis of the Terpenoids from Syneilesis palmata Essential Oil and the Variation of the Sesquiterpene Compounds by Harvest Year)

  • 최향숙
    • 한국식품영양학회지
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    • 제26권2호
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    • pp.287-294
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    • 2013
  • This study was investigated the chemical composition from Syneilesis palmata essential oil and the tendency of variation of the sesquiterpene compounds according to the harvesting time. The essential oils obtained by hydro distillation from the aerial parts of Syneilesis palmata were analyzed by GC and GC-MS. Ninety-eight compounds consisting of 9 aliphatic hydrocarbons, 17 sesquiterpene hydrocarbons, 11 aliphatic aldehydes, 1 terpene aldehyde, 8 aliphatic alcohols, 4 monoterpene alcohols, 16 sesquiterpene alcohols, 3 diterpene alcohols, 6 ketones, 11 esters, 8 oxides and epoxides, 3 acids and 1 miscellaneous one were identified from the oil. Spathulenol (22.33%) was the most abundant compound, followed by ${\beta}$- caryophyllene (6.23%), germacrene D (5.57%), longipinane (4.10%), and epiglobulol (3.65%). The volatile composition of Syneilesis palmata was characterized by higher contents of sesquiterpene compounds, especially sesquiterpene alcohols. The total content of 13 sesquiterpene compounds was decreased significantly from 2010 to 2012. ${\alpha}$-Caryophyllene, ${\beta}$-bisabolene, elemol, germacrene D, ${\beta}$-zingiberene, longipinane, and ${\beta}$-caryophyllene alcohol contents decreased, while ${\beta}$-bisabolol content increased during 3 years. The ecological responses to recent climate change may be influenced in the chemical components of natural plant terpenoids.

인삼 Sesquiterpene의 새로운 분리방법 (New Methods for Isolation of Sesquiterpene from Panax ginseng)

  • 위재준;신지영
    • Journal of Ginseng Research
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    • 제21권3호
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    • pp.214-218
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    • 1997
  • New simple methods for the Isolation of sesquiterpenes from Panax ginseng were developed. First, volatile compounds were isolated by simultaneous distillation and extraction (SDE) with 30% methanol and $\alpha$-hexane instead of water and ethyl ether/pentane (1:1). Secondly, head space volatiles in U-shaped tube at 7$0^{\circ}C$ were passed through C18 Sep-Pak by nitrogen gas streaming and the adsorbed volatiles were fluted by $\alpha$-hexane. TLC analysis showed that the volatile concentrates consisted mainly of terpenes when colored by vanillin-sulfuric and. GC/MS data revealed that approximately 30 sesquiterpenes of molecular weight 204 occupied 81.1% or more of the volatile concentrates isolated by those two newly developed methods. Among these, alloaromadendrene, germacrene B, isocaryophyllene, $\alpha$-neoclovene, ${\gamma}$-muurolene, $\beta$-panaslnsene, and $\alpha$-humulene were identified as being major sesqulterpenes by authentic samples or literatme search Key words : Panax ginseng, volatile compound, sesquiterpene, isolation, new method, GC/MS.

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산국의 잎과 줄기에서 분리한 Sesquiterpene Lactone들의 구조규명 및 생리활성 (Structural Analysis and Biological Activities of Sesquiterpene Lactones Isolated from the Leaves and Stems of Chrysanthemum boreale Makino)

  • 이종록;박문기
    • 한국환경과학회지
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    • 제26권11호
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    • pp.1285-1295
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    • 2017
  • Chrysanthemum boreale Makino is widely distributed in Korea, China, Japan and Southeast Asian countries. C. boreale is one of the herbs used for treating various inflammatory diseases in oriental medicine. The present study was conducted to identify biologically active compounds from the leaves and stems of C. boreale. We isolated two sesquiterpene sactones from the leaves and stems of C. boreale using silica gel column chromatography and recyclic high perfomance liquid chromatography. The lactones were characterized by their spectroscopic data (NMR, IR, MASS). These compounds were subjected to Farnesyl Protein Transferase (FPTase) inhibition, Nitric Oxide (NO) release inhibition and apoptosis inhibition. The structur of the following isolated compound were elucidated 8,10-${\small{O}$-Acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 4,10-dihydroxy-8-${\small{O}$-Acetyl-2,11(13)-guaiadiene-12,6-olide. In the NO release inhibition assay, compound 2 showed strong activities, with an $IC_{50}$ value of $7{\mu}g/mL$, whereas compound 1 did not exhibit significant activity with an $IC_{50}$ value of over $14{\mu}g/mL$ against murine macrophage.

A New Guaiane type Sesquiterpene from Torilis japonica

  • Ryu, Jae-Ha;Jeong, Yeon-Su
    • Archives of Pharmacal Research
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    • 제24권6호
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    • pp.532-535
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    • 2001
  • A new guaiane type sesquiterpene was isolated from the fruit of Torilis japonica (Umbelliferae). Based on NMR, IR and mass spectroscopy its structure was confirmed as deangeloyloxy torilin, $1{\beta},{\;}7{\alpha},{\;}10{\alpha}$H-11-acetoxy-guaia-4-en-3-one (1). This is the first report showing that this compound can be isolated from Torilis japonica.

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Tissue Factor Inhibitory Sesquiterpene Glycoside from Eriobotrya japonica

  • Lee, Ming-Hong;Son, Yeon-Kyoung;Han, Yong-Nam
    • Archives of Pharmacal Research
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    • 제27권6호
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    • pp.619-623
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    • 2004
  • Tissue factor (TF, tissue thromboplastin) is a membrane bound glycoprotein, which acceler-ates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor for activated factor VII (Vila). The TF-factor Vila complex (TF/VIIa) proteolytically activates factors IX and X, which leads to the generation of thrombin and fibrin clots. In order to isolate TF inhibitors, by means of a bioassay-directed chromatographic separation technique, from the leaves of Eriobotrya japonica Lindley (Rosaceae), a known sesquiterpene glycoside (2) and ferulic acid (3) were isolated as inhibitors that were evaluated using a single-clotting assay method for determining TF activity. Another sesquiterpene glycoside (1) was also isolated but was inactive in the assay system. Compound 3 was yielded by alkaline hydrolysis of compound 2. The structures of compounds 1, 2, and 3 were identified by means of spectral analysis as $3-O-{\alph}-L-rhamnopyranosyl-(1{\rightarrow}4)-a-L-rhamnopyranosyl-(1{\rightarrow}2)-[{\alph}-L-rhamnopyrano-syl-(1{\rightarrow}6)]-{\beta}-D-glucopyranosyl nerolidol$ (1), $3-O-{\alph}-L-rhamnopyranosyl-(1{\rightarrow}4)-{\alph}-L-rhamnopyr-anosyl-(1{\rightarrow}2)-[{\alph}-L-(4-trans-feruloyl)-rhamnopyranosyl-(1{\rightarrow}6)]-{\beta}-D-glucopyranosyl$ nerolidol (2) and ferulic acid (3), respectively. Compounds 2 and 3 inhibited 50% of the TF activity at con-centrations of 2 and $369{\;}\mu\textrm{m}/TF$ units, respectively.

A Sesquiterpene ortho-Naphthoquinone from the Root Bark of Ulmus davidiana Planch

  • Kim, Jong-Pyung;Kim, Won-Gon;Park, Jong-Hee;Jung, Jin;Koshino, Hiroyuki;Yoo, Ick-Dong
    • 생약학회지
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    • 제27권1호
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    • pp.26-31
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    • 1996
  • A sesquiterpene ortho-naphtpoquinone was isolated from the 80% aqueous methanolic extract of root bark of Ulmus davidiana Planch whose stem and root bark have been used as an oriental medicine for the treatment of edema, mastitis, gastric cancer and inflammation. On the basis of spectral data obtained from UV-vis, IR, HR-EIMS and NMR spectrometry, including the pulse field gradient (PFG) HMQC and HMBC techniques, the structure of this compound was determined as 2,3-dihydro-3-hydroxy-3,6,9-trimethylnaphtho(1,8-b,c)pyran-7,8-dione which has been known as mansonone 1. This compound has been isolated only from the heart-wood of Mansonia altissima Chev, a Sterculiacea from West Africa. Thus, this compound was isolated for the second time from natural source in this study. This is the first report to present the carbon chemical shift assignment of mansonone I.

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Antibiotic Components from the Rhizomes of Curcuma zedoaria

  • Jeong, Choon Sik;Shim, Sang Hee
    • Natural Product Sciences
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    • 제21권3호
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    • pp.147-149
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    • 2015
  • Two terpenoids, including one uniquely aromatized one (1), were isolated from CH2Cl2-soluble fraction of MeOH extracts of Curcuma zedoaria. They were identified to be a sesquiterpene ketolactone (1) and orobanone (2), respectively on the basis of their NMR data. The structure of compound 1 was confirmed by X-ray chrystallography and the reported NMR assignments for 1 were revised in this study. Antibiotic activities for compounds 1 and 2 were evaluated using disk diffusion assay. Compound 1 showed potent antibacterial activities against Listeria monocytogenes and Staphylococcus pseudointermedius while compound 2 was active against Bacillus cereus.

Hymenoxys brachyactis의 화학성분에 관한 연구(II) (The study of chemical substances in Hymenoxys brachyactis(II))

  • 이상준;김성한;김정한
    • Applied Biological Chemistry
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    • 제38권5호
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    • pp.473-477
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    • 1995
  • Hymenoxys brachyactis지상부의 디클로로메탄 추출액으로부터 3개의 sesquiterpene lactone들과 새로운 lactone화합물인 isohymenograndin을 확인하였다. 그리고 2개의 sesquiterpene lactone축합물인 biennine C와 독성이 있는 것으로 알려진 flavone화합물인 hispidulin을 분리하여 각각을 고자장 NMR, Mass등의 기기를 이용하여 구조결정 하였다. Biennine C는 gas chromatography와 Mass분석을 통하여 독성화합물 hymenoxon과 화합물 8과의 Diels-Alder축합물임을 확인하였다. biennine C를 포함한 이상의 lactone화합물들은 ${\alpha},{\beta}$-unsaturated lactone으로서 독성화합물군으로서 알려진 hymenovin과 공통적인 구조를 갖고 있어서 생체독성을 나타낼 가능성이 높은 화합물들로 사료된다.

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Sesquiterpene Lactones from the Roots of Ixeris sonchifolia

  • Jo, Young-Mi;Suh, Ji-Young;Bae, Song-Ja;Jung, Jee-H.;Im, Kwang-Sik
    • Natural Product Sciences
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    • 제11권2호
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    • pp.55-57
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    • 2005
  • Three known sesquiterpene lactones were isolated from the n-BuOH traction of the roots of Ixeris sonchifolia. Their structures were identified as macrocliniside A (1), glucozaluzanin C (2), and ixerin H (3), by spectral analyses. Compounds 1 and 2 are guaiane-type, while compound 3 is a germacrane-type sesquiterpene lactone. Compounds 1-3 are first isolated from I. sonchifolia.