Skip to main content
Log in

The constituents ofTaraxacum hallaisanensis roots

  • Research Articles
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Three sesquiterpene lactone compounds, two novel(1β, 3β-dihydroxy-6β, 11β, 4α, 5α, 7αH-eudesm-12,6-olide-1-O-β-D-glucopyranoside, 1β, 3β-dihydroxy-6β, 4β, 5α, 7αH-eudesm-11 en-12,6-olide-1-O-β-D-glucopyranoside) and 1β, 3β-dihydroxy-6β, 11β, 4α, 5α, 7αH-eudesm-12,6-olide were isolated from the aqueous fraction of MeOH extract of the roots fromTaraxacum 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 β-amyrin acetate, α-amyrin acetate and lupeol acetate. Structures of isolated compounds were elucidated by spectroscopic parameters of IR, Mass,13C-NMR,1H-NMR,1H-1H COSY,13C-1H COSY and HMBC.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References Cited

  • Ageta, H., Shiojima, K. and Masuda, K., Compositae Constituents., Four New Triterpenoids, Neolupenol, Tarolupenol And Their Acetate Isolated From Roots of a Japanese Dandelion.Taraxacum Japonicum. Tetrahedron Letters, 22, 242–289 (1981).

    Google Scholar 

  • Akihisa, T., Thakur, S., Rosentein, F. and Matsumoto, T., Sterols of Cucurbitaceae; The Configurations at C-24 of 4-Alkyl-Δ5-, Δ7-, and Δ8-Sterol.Lipids, 21(1), 39–47 (1986).

    Article  CAS  Google Scholar 

  • Arias, J.M. and Breton, J.L., Microbial Transformation of Sesquiterpenoids: Conversation of Deoxyvulgarin byRhizopus nigricans andAspergillus ochraceous.J. Chem. Soc., Perk-in. Trans., 1, 471–474 (1987).

    Article  Google Scholar 

  • Barrera, J.B., Breton, J.L., Fajardo, M. and Gonzalez, A.G., Terpenoids from the Sonchus VI Tuberiferine from Sonchus Tuberifer Svent.Tetrahedron Letters, 36, 3475–3476 (1967).

    Article  Google Scholar 

  • Bass, W. J., Berkel, I.E.M., Heerma, C.V.W. and Kreyenbroek, M.N., Ring A fissioned 3,4-seco-3-nor-triterpene-2-aldehydes and related pentacyclic triterpenoids from the leaf wax ofHoya australis.Phytochemistry, 31(6), 2073 (1992).

    Article  Google Scholar 

  • Booth, V.H., Taraxien, The Carotenoid Ester in Dandelion Flowers.Phytochemistry, 3, 229–234 (1964).

    Article  CAS  Google Scholar 

  • Brauno, M. and Herz, W., Eudesmanolides fromPicris aculeata.Phytochemistry, 27(4), 1201–1203 (1988).

    Article  Google Scholar 

  • Budzikiewicz, H., Wilson, J.M. and Djerassi, C., Mass Spectrometry in Structural and Stereochemical Problems XXXII. Pentacyclic Triterpenes.J. Am. Chem. Soc., 85, 3688–3699 (1963).

    Article  CAS  Google Scholar 

  • Fischer, N.H., Oliver, E.J. and Fischer, H.D., The Biogenesis and Chemistry of Sesquiterpene Lactones, Progress in the Chemistry of Organic Natural Products. Springer-Verlag, 134 (1979).

  • Fraga, M., Hernandez, G., Mestres, M. and Perales, A., Eudesman Sesquiterpene fromTeucrium Heterophyllium. The X-ray Structure of Teucdiol A.Phytochemistry, 34(4), 1083–1086 (1993).

    Article  CAS  Google Scholar 

  • Garg, V.K. and Nes, W.R., Codisterol and other Δ5-Sterols in the Seeds ofCucurbita maxima.Phytochemistry, 23(12), 2925–2929 (1984).

    Article  CAS  Google Scholar 

  • Goren, N. and Tahtasakal, E., Sesquiterpenoids ofTanacetum chiliophylium var. heimerlei.Phytochemistry, 34(4), 1071–1073 (1993).

    Article  CAS  Google Scholar 

  • Hansel, R., Katarahardja, M., Huang, J. T. and Bohlmann, F., Sesquiterpene lactone-β-D-glucopyranoside Sowie Ein Neues Eudesmanolid AusTaraxacum officinale.Phytochemistry, 19, 857–861 (1980).

    Article  Google Scholar 

  • Harapanhalli, R.S., Synthesis of Erivanin and 1-Epierivanin from 1-(α)-Santonin.J. Chem. Soc. Perkin. Trans 1, 2633–2637 (1988).

    Article  Google Scholar 

  • Holub, M., Contribution to the Biogenesis of Sesquiterpene lactones of the Species of Umbelliferae family.Natural product Chemistry, 37–49 (1984).

  • Holub, M., Budesinsky, M., Smitalova, Z. and Saman, D., 5βH, 6αH, 7αH, 10α CH3-Eudesman-6,12-Olides: A Novel Stereochemical Group of Natural Sesquiterpene Lactones Stereo Structure of Isosilerolide.Tetrahedron Letters, 23(46), 4853–4856 (1982).

    Article  CAS  Google Scholar 

  • Huh, J., Dong I Bo Gam. Namsan-dang, 1211 (1986).

  • Kim, M.H., Flora of Cheju island, Cheju-do. 484 (1992).

  • Kim. I.H., Pharmacal Botany. Jin-Myong Publishing Co., 339 (1974).

  • Kouno, I., Mori, K., Okamoto, S. and Sato, S., Structure of Anislactone A and B, Novel type of Sesquiterpene lactones from the Pericarps ofIllicium anisatum.Chem. Pharm. Bull., 38(11), 3060–3063 (1990).

    CAS  Google Scholar 

  • Irie, H., Matsumoto, R., Nishimura, M. and Zhang, Y., Synthesis of (+)-Heritol, a Sesquiterpene Lactone belonging to the Aromatic Cadinane Group.Pharmaceutical Society of Japan, 38(7), 1852–1856 (1990).

    CAS  Google Scholar 

  • Irwin, M.A. and Geissman, T.A., Ridentin-B An Eudesmanolide fromArtemisia. Tripartita ssp. rupicola.Phytochemistry, 12, 871–873 (1973).

    Article  CAS  Google Scholar 

  • Jimenez, A., Pereda-Miranda, R., Bye, R., Linarrest, E. and Mata, R., Ratibinolide III, A Sesquiterpene Lactone Glucoside, fromRatibida Latipalearis.Phytochemistry, 34 (4), 1079–1082 (1993).

    Article  CAS  Google Scholar 

  • Lee, K.H. and Geissman, T.A., Sesquiterpene lactones of Artemisia constituents ofA. Ludoviciana ssp. Mexicana.Phytochemistry, 9, 403–408 (1970).

    Article  CAS  Google Scholar 

  • Marco, J.A. and Carda, M.,13C-NMR Spectra of Eudesmanolides 1-Eudesman-12, 6-olides.Magnetic Resonance in Chemistry, 25, 628–634 (1987).

    Article  CAS  Google Scholar 

  • Mahmoud, Z.F., Salam, N.A.A., Sarg, T.M. and Bohlmann, F., A Carotane Derivative and a Eudesmanolide fromInula Crithmoides.Phytochemistry, 20(4), 735–738 (1981).

    Article  CAS  Google Scholar 

  • Miyase, T. and Fukushima, S., Sesquiterpene Lactones fromAinsliaea acerifolia Sch. Bip. andA. Disecta Franch et Sav.,Chem. Pharm. Bull., 32(8), 3043–3046 (1984).

    CAS  Google Scholar 

  • Moon K. B., Flora of Korean plant. Moon Kyo Boo, 1264–1265 (1965).

  • Nes, W.R., Norton, R.A. and Benson, M., Carbon-13 NMR Studies on Sitosterol Biosynthesized from [13C] Mevalonates.Phytochemistry, 31(3), 805–811 (1992).

    Article  CAS  Google Scholar 

  • Oshima, Y., Tanaka, K. and Hikino, H., Sesquiterpenoid fromRehmannia Glutinosa roots.Phytochemistry, 33(1), 233–234 (1993).

    Article  CAS  Google Scholar 

  • Porter, L.J., Newman, R.H., Foo, L.Y. and Wong, H., Polymericproanthocyanidins.J. Chem. Soc. Perkin 1, 1217 (1982).

    Article  Google Scholar 

  • Radosevich, M.B., Delfel, N.E. and England, R., Gaschromatography-mass spectrometry of oleanane and ursane type triterpenes-application toChenopodium Quuinoa triterpenes.Phytochemistry, 24(9), 2063 (1985).

    Article  Google Scholar 

  • Rauwald, H.W. and Huang, J., Taraxacoside, A type of Acylated r-Butyrolactone Glycoside FromTaraxacum officinale.Phytochemistry, 24, 1557 (1985).

    Article  CAS  Google Scholar 

  • Rutherford, P.P. and Deacon, A.C., Fructofuranosidases from Roots of Dandelion (Taraxacum officinale).Biochem. J., 126, 569–573 (1972).

    CAS  PubMed  Google Scholar 

  • Sanz, J. F. and Marco, J. A., New Eudesmanolides Related To Torrentin fromArtemisia herba-alba subsp. valentina.Planta Med., 57, 74 (1991).

    Article  CAS  PubMed  Google Scholar 

  • Sanz, J.F., Falco, E. and Marco, J.A., Further new Sesquiterpene Lactones fromArtemisia herba-alba subsp. valentina.Journal of Natural Products, 53(4), 940–945 (1990).

    Article  CAS  Google Scholar 

  • Whang, W.K., Oh, I.S., Lee, M.T., Yang, D.S. and Kim, I.H., Pharmaco-constituents ofTaraxacum hallaisanensis(I): Phenolic Compounds from Aerial Part ofTaraxacum hallaisanensis.Kor. J. Pharmacogn. 25(3), 209–213 (1994).

    CAS  Google Scholar 

  • Yamakawa, K. and Nishitani, K., Studies on the Terpenoids and related Alicyclic Compounds VIII.Chem. Pharm. Bull., 24(11), 2810–2817 (1976).

    CAS  Google Scholar 

  • Yaoita, Y., Nagata, K., Suzuki, S. and Kikuchi, M., Structure of Eremophilenolide from the Rhizomes ofPetasites japonicus.Chem. Pharm. Bull., 40(12), 3277–3279 (1992).

    CAS  Google Scholar 

  • Yook, C.S.,Flora of Korean medicinal plant. Jin-Myong Publishing Co., pp. 406, 1981.

  • Young, H.S., Park, J.C. and Choi, J.S., Isolation of (+)-catechin from the roots ofRosa rugosa.Kor. J. Pharmacogn., 18(3), 177 (1987).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yang, D.S., Whang, W.K. & Kim, I.H. The constituents ofTaraxacum hallaisanensis roots. Arch. Pharm. Res. 19, 507–513 (1996). https://doi.org/10.1007/BF02986020

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02986020

Key words

Navigation