• Title/Summary/Keyword: Sesquiterpene glucopyranoside

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Phytochemical Study of the Aerial Parts of Conyza discoridis Growing in Saudi Arabia

  • Alqasoumi, Saleh I.
    • Natural Product Sciences
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    • v.15 no.2
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    • pp.66-70
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    • 2009
  • Phytochemical investigation of the aerial parts of Conyza discoridis (L.) Desf. resulted in the isolation of the new sesquiterpene dilactone ester vernomenin-6-(2-hydroxymethyl)-acrylate (4) and two known sesquiterpene dilactones vernolepin (1) and vernomenin (3). Two known flavonols, 3-O-methylquercetin (2) and transilin (3-O-methylquercetin 7-O-${\beta}$-D-glucopyranoside) (5), were also identified. The structures were determined utilizing physical, chemical and spectral methods.

Cytotoxic Constituents of the Leaves of Ixeris sonchifolia

  • Suh, Ji-Young;Jo, Young-Mi;Kim, Nam-Deuk;Bae, Song-Ja;Jung, Jee-H.;Im, Kwang-Sik
    • Archives of Pharmacal Research
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    • v.25 no.3
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    • pp.289-292
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    • 2002
  • The ethyl acetate extract of the leaves of Ixeris sonchifolia afforded two new and two known sesquiterpene lactone glucosides of the guaiane-type, together with a known alkenol glucoside. The known compounds were identified as ixerin Z (1), ixerin Z-6'-p-hydroxyphenylace-tate (2), and (Z)-3-hexen-1-ol-$\beta$-D-glucopyranoside (3), respectively. The structures of the new compounds were elucidated as 11, 13a-dihydroixerin Z [4, 3-hydroxy-2-oxo-guaia-1 (10), $3-dien-5{\alpha},6{\beta},7{\alpha},11{\beta}H-12,6-olide-3-O-{\beta}-D-glucopyranoside],{\;}and{\;}3,10{\$beta}-dihydroxy-2-oxo-guaia-3,11(13)-dien-1{\alpha},5{\alpha},6{\alpha},7aH-12,6-olide-10-O-{\beta}-D-glucopyranoside$ (5), respectively. The cytotoxicity of these compounds against human hepatocellular carcinoma cell (HepG2) and human melanoma cell (SK-MEL-2) was evaluated.

Dentatins: Sesquiterpene Glucosides from lxeris dentata

  • Chung, Ha-Sook;Woo, Won-Sik;Lim, Sook-Ja
    • Archives of Pharmacal Research
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    • v.17 no.5
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    • pp.323-326
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    • 1994
  • Three new sesquiterpene lactone glucosides named dentatins A, B and C were isolated from lxeris dentata and the structures were elucidated as $3{\betha}, {\;}8{\betha}-dihydroxy-(1{\alpha}, 5{\alpha})guainan-10(14)-ene-6{\alpha}, {;\}12-olide-3-O-{\betha}-D-giucopyuranoside{\;}(1), {\;}3{\betha}, {\;}8{\betha}-dihydroxy-(1{\alpha}, {\;}5{\alpha})-guaian-4(15), {\;}10(14)-diene-6{\alpha}, {\;}12-plide-3-O-{\betha}-D-glucopyranoside{\;}(3)$, respectively, on the basis of spectral evidence.

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Cyclofarnesane sesquiterpene glucoside from the whole plant of Loranthus tanakae and its cytotoxicity ('꼬리겨우살이'(Loranthus tanakae) 전초로부터 cyclofarnesane sesquiterpene glucoside의 분리 동정 및 세포독성)

  • Joo, Sun-Woo;Kim, Hyoung-Geun;Oh, Eun-Ji;Ko, Jung-Hwan;Lee, Yeong-Geun;Kang, Se-Chan;Lee, Dae Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.62 no.1
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    • pp.7-10
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    • 2019
  • The whole plants of Loranthus tanakae were repeatedly extracted with 80% aqueous MeOH and the concentrate was partitioned into ethyl acetate (EtOAc), n-butyl alcohol (n-BuOH) and $H_2O$ fractions. The repeated silica gel ($SiO_2$), octadecyl $SiO_2$ (ODS), and Sephadex LH-20 column chromatographies for the n-BuOH fraction led to isolation of a cyclofarnesane sesquiterpene glucoside. The chemical structure including stereo structure was determined to be a (1'R,3'S,5'R,8'S,2E,4E)-dihydrophaseic acid $3^{\prime}-O-{\beta}-{\text\tiny{D}}$-glucopyranoside on the basis of spectroscopic analyses. This compound was isolated for the first time from L. tanakae in this study. Compound 1 showed a moderate dose-dependent cytotoxicity against human Caucasian gastric adenocarcinoma cells and human hepatocyte cari-noma cells cell lines at higher than $50{\mu}g/mL$.

A New Sesquiterpene Hydroperoxide from the Aerial Parts of Aster oharai

  • Choi, Sang-Zin;Lee, Sung-Ok;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.26 no.7
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    • pp.521-525
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    • 2003
  • Phytochemical works on the aerial parts of Aster oharai (Compositae) led to the isolation of a new sesquiterpene hydroperoxide, 7$\alpha$-hydroperoxy-3, 11-eudesmadiene (2) and seven known compounds, teucdiol B (1), $\alpha$-spinasterol (3), oleanolic acid (4), $\alpha$-spinasterol 3-Ο-$\beta$-D-glucopyranoside (5), methyl 3,5-di-Ο-caffeoyl quinate (6), 3,5-di-Ο-caffeoylquinic acid (7), 3,4-di-Ο-caffeoylquinic acid (8). The chemical structures of 1-8 were established by chemical and spectroscopic methods. Compound 2 showed cytotoxicity against cultured human tumor cell lines in vitro, SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), and HCT15 (colon) with $ED_{50}$ values ranging from 3.86-17.21 $\mu$g/mL.

The constituents of taraxacum hallaisanensis roots

  • Yang, Deuk-Suk;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.507-513
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    • 1996
  • Three sesquiterpene lactone compounds, two novel(1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha.,7.alpha.H -eudesm-12, 6-olide-1-O-.betha.-D-glucopyranoside, 1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha.,7.alpha.H-eudes m-12,6-olide-1-O-.betha.-D-glucopyranoside) and 1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha., 7.alpha.H-eudesm-12,6-olide were isolated from the aqueous fraction of MeOH extract of the roots from Taraxacum hallaisanensis (Compositae) employing Amberlite XAD-2, ODS-gel, silica gel and Sephadex LH-20 column chromatographics. Another known compound, (-)-epicatechin, was isolated from the aqueous fraction of the MeOH extract. The total MeOH extract also contained phytosterol and a mixture of .betha.-amyrin acetate, .alpha.-amyrin acetate and lupeol acetate. Structures of isolated compounds were elucidated by spectroscopic parameters of IR, Mass, /sup 13/C-NMR, /sup 1/H-NMR, /sup 1/H-/sup 1/H COSY, /sup 13/C-/sup 1/H COSY and HMBC.

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Fragrance and Metabolite Components of Flowers from Korean Native Apocynum lancifolium Russanov

  • Kim, JoHoon;Lee, JaeMyun;Park, YeGun;Ann, SeoungWon;Baik, JungAe
    • Journal of Environmental Science International
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    • v.30 no.10
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    • pp.879-889
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    • 2021
  • This study characterizes the volatile aromatic and metabolite components of domestic native Apocynum lancifolium blossom. The accurate characterization of fragrances collected from the blossom was carried out using gas chromatography-mass. A total of 70 chemical components were identified, including ketones of acetophenone (29.22%), phenylethyl alcohol (10.54%), methyl-benzenemethanol (8.43%), benzyl alcohol (7.97%), natural bicyclic sesquiterpene types of caryophyllene (6.08%), gurjunene (6.20%), humulene (1.90%), and ocimene (1.04%). Overall, the content of ketones, alcohols, and terpenes was higher than that of others. The major metabolite components were pentanoic acid, malic acid, fructofuranoside, quinic acid, tagatose, sorbose, galactose, inositol, galactaric acid, glucopyranoside, and octadecenoic acid.