Download PDF
Planta Med 2005; 71(8): 792-794
DOI: 10.1055/s-2005-871227
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Diterpene Glycosides from Egletes viscosa

Dongho Lee1 , 4 , Chen Li1 , Tyler N. Graf1 , Jose Schunke Vigo2 , James G. Graham3 , 5 , Fernando Cabieses2 , Norman R. Farnsworth3 , Geoffrey A. Cordell3 , A. Douglas Kinghorn3 , 6 , David J. Kroll1 , Mansukh C. Wani1 , Nicholas H. Oberlies1
  • 1Natural Products Laboratory, Research Triangle Institute, Research Triangle Park, North Carolina, USA
  • 2Instituto Nacional de Medicina Tradicional (INMETRA), Minesterio de Salud, Jesus Maria, Lima, Peru
  • 3Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois, USA
  • 4Korea Research Institute of Bioscience and Biotechnology, Daejeon, Korea
  • 5Center for Ethnobiology and Natural Products, Florida International University, University Park Campus, Miami, Florida, USA
  • 6Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio, USA
Further Information

Publication History

Received: November 11, 2004

Accepted: February 2, 2005

Publication Date:
11 August 2005 (online)

    Permissions and Reprints

Abstract

A phytochemical investigation of the CHCl3-soluble extract of the entire plant of Egletes viscosa (Asteraceae), collected in Peru, afforded two new labdane glycosides, 13-hydroxy-7-oxolabda-8,14-diene 13(R)-O-α-L-arabinopyranoside and 13-hydroxylabda-7,14-diene 13(R)-O-α-L-arabinopyranoside, along with four known compounds. The structures of the new compounds were elucidated by spectroscopic and chemical methods.

References

  • 1 Lima M AS, Silveira E R, Marques M SL, Santos R HA, Gambardela M TP. Biologically active flavonoids and terpenoids from Egletes viscosa .  Phytochemistry. 1996;  41 217-23
    CrossrefPubMedGoogle Scholar
  • 2 Rao V SN, Mendezes A MS, Gadelha M GT. Antifertility screening of some indigenous plants of Brazil.  Fitoterapia. 1988;  59 17-20
    PubMedGoogle Scholar
  • 3 Rao V SN, Santos F A, Sobreira T T, Souza M F, Melo C L, Silveira E R. Investigations on the gastroprotective and antidiarrhoeal properties of ternatin, a tetramethoxyflavone from Egletes viscosa .  Planta Med. 1997;  63 146-9
    PubMedGoogle Scholar
  • 4 Guedes M M, Cunha A N, Silveira E R, Rao V SN. Antinociceptive and gastroprotective effects of diterpenes from the flower buds of Egletes viscosa .  Planta Med. 2002;  68 1044-6
    Article in Thieme ConnectPubMedGoogle Scholar
  • 5 Kinghorn A D, Farnsworth N R, Soejarto D D, Cordell G A, Swanson S M, Pezzuto J M. et al . Novel strategies for the discovery of plant-derived anticancer agents.  Pharm Biol. 2003;  41 (supplement) 53-67
    CrossrefPubMedGoogle Scholar
  • 6 Batterham T J, Highet R J. Nuclear magnetic resonance spectra of flavonoids.  Aust J Chem. 1964;  17 428-32
    PubMedGoogle Scholar
  • 7 Rodriguez B, Valverde S, Fraga B M, Gonzalez A G, Hernandez M G. Determination of stereochemistry of C-14 in 8,13-epi-epoxy-14,15-dihydroxylabdanes using proton NMR spectroscopy.  An Quim. 1976;  72 850-4
    PubMedGoogle Scholar
  • 8 Stierle D B, Stierle A A, Larsen R D. Terpenoid and flavone constituents of Polemonium viscosum .  Phytochemistry. 1988;  27 517-22
    CrossrefPubMedGoogle Scholar
  • 9 Torrenegra R, Robles J, Waibel R, Lowel M, Achenbach H. Diterpenes and diterpene xylosides from Conyza trihecatactis .  Phytochemistry. 1994;  35 195-9
    PubMedGoogle Scholar
  • 10 Ahmed A A, Mahmoud A A, Ahmed U M, El-Bassuony A A, Abd El-Razk M H, Pare P W. et al . Manoyl oxide α-arabinopyranoside and grindelic acid diterpenoids from Grindelia integrifolia .  J Nat Prod. 2001;  64 1365-7
    CrossrefPubMedGoogle Scholar
  • 11 Jakupovic J, Ellmauerer E, Bohlmann F, King R M, Robinson H. ent-Labdanes from Austrobrickellia patens .  Phytochemistry. 1986;  25 1927-9
    CrossrefPubMedGoogle Scholar
  • 12 Wu C -L, Lin H -R. Labdanoids and bis(bibenzyls) from Jungermannia species.  Phytochemistry. 1997;  44 101-5
    CrossrefPubMedGoogle Scholar
  • 13 Kim N -C, Desjardins A E, Wu C D, Kinghorn A D. Activity of triterpenoid glycosides from the root bark of Mussaenda macrophylla against two oral pathogens.  J Nat Prod. 1999;  62 1379-84
    CrossrefPubMedGoogle Scholar
  • 14 Uchio Y, Nagasaki M, Eguchi S, Matsuo A, Nakayama M, Hayashi S. Labdane diterpene glycosides with 6-deoxy-L-idose from Aster spathulifolius Maxim.  Tetrahedron Lett. 1980;  21 3775-8
    CrossrefPubMedGoogle Scholar
  • 15 Khan M R, Gray A I, Waterman P G. Clerodane diterpenes from Zuelania guidonia stem bark.  Phytochemistry. 1990;  29 2939-42
    CrossrefPubMedGoogle Scholar
  • 16 Choi S Z, Kwon H C, Choi S U, Lee K R. Five new labdane diterpenes from Aster oharai .  J Nat Prod. 2002;  65 1102-6
    CrossrefPubMedGoogle Scholar
  • 17 Gu J -Q, Graf T N, Lee D, Chai H -B, Mi Q, Kardono L BS. et al . Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia.  J Nat Prod. 2004;  67 1156-61
    CrossrefPubMedGoogle Scholar
  • 18 Wall M E, Wani M C, Brown D M, Fullas F, Oswald J B, Josephson F F. et al . Effect of tannins on screening of plant extracts for enzyme inhibitory activity and techniques for their removal.  Phytomedicine. 1996;  3 281-5
    CrossrefPubMedGoogle Scholar
  • 19 Torrenegra R, Pedrozo J, Robles J, Waibel R, Achenbach H. Diterpenes from Gnaphalium pellitum and Gnaphalium graveolens .  Phytochemistry. 1992;  31 2415-8
    CrossrefPubMedGoogle Scholar

Nicholas H. Oberlies

Natural Products Laboratory

Research Triangle Institute

P.O. Box 12194

Research Triangle Park

North Carolina 27709

USA

Fax: +1-919-541-6499

Email: oberlies@rti.org

      >