Download PDF
Planta Med 2003; 69(9): 846-850
DOI: 10.1055/s-2003-43212
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Terpenoids of Salvia hydrangea: Two New, Rearranged 20-Norabietanes and the Effect of Oleanolic Acid on Erythrocyte Membranes

Majid Sairafianpour1 , Babak Bahreininejad2 , Matthias Witt3 , Hanne L. Ziegler1 , Jerzy W. Jaroszewski1 , Dan Stærk1
  • 1Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, Copenhagen, Denmark
  • 2Medicinal Plants Unit, Isfahan Research Centre of Natural Resources and Animal Science, Isfahan, Islamic Republic of Iran
  • 3Bruker Daltonik GmbH, Bremen, Germany
Further Information

Publication History

Received: January 28, 2003

Accepted: March 11, 2002

Publication Date:
04 November 2003 (online)

Also available at
    Permissions and Reprints

Abstract

Four abietane-type terpenoids, including two known royleanones and two new, rearranged 20-norabietanes, were isolated from the roots of the Iranian medicinal plant Salvia hydrangea DC. ex Bentham (Lamiaceae), which is used as an anthelmintic and antileishmanial remedy. Their structures were established using COSY, NOESY, HSQC, and HMBC spectral data. The possible identity of one of the 20-norabietanes with demethylmulticauline, previously reported from a different Salvia species, is discussed. A moderate in vitro antiplasmodial effect of the extract of S. hydrangea flowers was found to be associated with the presence of large amounts of pentacyclic triterpenes, mainly oleanolic acid. The observed antiplasmodial activity of oleanolic acid is apparently due to its incorporation into the erythrocyte membrane, which adversely affects the growth of Plasmodium falciparum parasites. Thus, oleanolic acid caused transformation of erythrocytes into stomatocytes in the concentration range where the in vitro antiplasmodial activity was observed.

Key words

Salvia hydrangea - Lamiaceae - norabietanes - Plasmodium falci-parum - royleanones - stomatocytes - erythrocyte membrane

References

  • 1 Huang K C. The Pharmacology of Chinese Herbs,. 2nd edn., Boca Raton; CRC Press 1999: 91-4
    Search in Google Scholar
  • 2 Baricevic D, Bartol T. The biological/pharmacological activity of the Salvia genus.  Medicinal and Aromatic Plants Industrial Profiles. 2000;  14 143-84
    PubMedSearch in Google Scholar
  • 3 Ji X Y, Tan B K, Zhu Y Z. Salvia miltiorrhiza and ischemic diseases.  Acta Pharmacologica Sinica. 2000;  21 1089-94
    PubMedSearch in Google Scholar
  • 4 Sabri N N, El-Lakany A M. Diterpenoids in the genus Salvia: diterpene quinones.  Alexandria Journal of Pharmaceutical Sciences. 1990;  4 95-105
    PubMedSearch in Google Scholar
  • 5 Chang H M, Cheng K P, Choang T F, Chow H F, Chui K Y, Hon P M, Tan F WL, Yang Y, Zhong Z P, Lee C M, Sham H L, Chan C F, Cui Y X, Wong H NC. Structure elucidation and total synthesis of new tanshinones isolated from Salvia miltiorrhiza Bunge (Danshen).  Journal of Organic Chemistry. 1990;  55 3537-43
    CrossrefPubMedSearch in Google Scholar
  • 6 Sairafianpour M, Christensen J, Stærk D, Budnik B A, Kharazmi A, Bagherzadeh K, Jaroszewski J W. Leishmanicidal, antiplasmodial and cytotoxic activity of novel diterpenoid 1,2-quinones from Perovskia abrotanoides: new source of tanshinones.  Journal of Natural Products. 2001;  64 1398-403
    CrossrefPubMedSearch in Google Scholar
  • 7 Esquivel B, Calderon J S, Flores E, Sanchez A A, Rivera R R. Abietane and icetexane diterpenoids from Salvia ballotaeflora and Salvia axillaris .  Phytochemistry. 1997;  46 531-4
    CrossrefPubMedSearch in Google Scholar
  • 8 Nagy G, Günther G, Mathe I, Blunden G, Yang M, Crabb T A. Diterpenoids from Salvia glutinosa, S. austriaca, S. tomentosa and S. verticillata roots.  Phytochemistry. 1999;  52 1105-9
    CrossrefPubMedSearch in Google Scholar
  • 9 Patudin A, Romanowa A, Sokolow W S, Pribylowa G. Das Vorkommen von Phenanthrenchinonen in Arten der Gattung Salvia .  Planta Medica. 1974;  26 201-7
    PubMedSearch in Google Scholar
  • 10 Amin G. Popular Medicinal Plants of Iran. Vol 1., Teheran; Ministry of Health Publications 1991: 41
    Search in Google Scholar
  • 11 Ghannadi A, Samsam-Shariat S H, Moattar F. Composition of the leaf oil of Salvia hydrangea grown in Iran.  Journal of Essential Oil Research. 1999;  11 745-6
    PubMedSearch in Google Scholar
  • 12 Rustaiyan A, Masoudi S, Jassbi A. Essential oil of Salvia hydrangea DC. ex Benth.  Journal of Essential Oil Research. 1997;  9 599-600
    PubMedSearch in Google Scholar
  • 13 Kuo Y H, Wu T R, Cheng M C, Wang Y. Five new compounds from the heartwood of Juniperus formosana Hayata.  Chemical and Pharmaceutical Bulletin. 1990;  38 3195-201
    PubMedSearch in Google Scholar
  • 14 Tezuka Y, Kasimu R, Li J X, Basnet P, Tanaka K, Namba T, Kadota S. Constituents of roots of Salvia deserta Schang. (Xinjiang-Danshen).  Chemical and Pharmaceutical Bulletin. 1998;  46 107-12
    CrossrefPubMedSearch in Google Scholar
  • 15 Matsumoto T, Hasrada S. The total synthesis of (+)-taxoqionone, (-)-7α-acetoxyroyleanone, (-)-dehydroroyleanone, (-)-horminone, (-)-7-oxoroyleanone, and (+)-inurpyleanol.  Bulletin of the Chemical Society of Japan. 1979;  52 1459-63
    PubMedSearch in Google Scholar
  • 16 Ziegler H L, Stærk D, Christensen J, Hviid L, Hägerstrand H, Jaroszewski J W. In vitro Plasmodium falciparum drug sensitivity assay: inhibition of parasite growth by incorporation of stomatocytogenic amphiphiles into erythrocyte membrane.  Antimicrobial Agents and Chemotherapy. 2002;  46 1441-6
    CrossrefPubMedSearch in Google Scholar
  • 17 Ziegler H L, Jensen T H, Christensen J, Stærk D, Hägerstrand H, Sittie A A, Olesen C E, Staalsø T, Ekpe P, Jaroszewski J W. Possible artefacts in the in vitro determination of antimalarial activity of natural products that incorporate into lipid bilayer: apparent antiplasmodial activity of dehydroabietinol, a constituent of Hyptis suaveolens .  Planta Medica. 2002;  68 547-9
    Thieme ConnectPubMedSearch in Google Scholar
  • 18 Bessis M. Red cell shapes, an illustrated classification and its rationale. In Bessis M, Weed RI, Leblond PF (eds.) Red Cell Shape. Physiology, Pathology, Ultrastructure. Heidelberg; Springer-Verlag 1973: 1-24
    Search in Google Scholar
  • 19 Ulubelen A, Topcu G, Johansson C B. Norditerpenoids and diterpenoids from Salvia multicaulis with antituberculous activity.  Journal of Natural Products. 1997;  60 1275-80
    CrossrefPubMedSearch in Google Scholar
  • 20 Chow Y L, Buono-Core G E, Zhang L M, Johansson C I. The photocycloaddition of methoxynaphthalenes with acetylenes and acid-catalysed retardation: reactions of non-fluorescent exciplexes. Journal of Chemical Society, Perkin Transactions 2 1995: 1691-8
    Search in Google Scholar
  • 21 Ewing D E. 13C Substituent effects on monosubstituted benzenes.  Organic Magnetic Resonance. 1979;  12 499-524
    CrossrefPubMedSearch in Google Scholar
  • 22 Long S AT, Memory J D. H-H, C-H and C-C NMR spin-spin coupling constants calculated by the FP-INDO method for aromatic hydrocarbons.  Journal of Magnetic Resonance. 1978;  29 119-24
    PubMedSearch in Google Scholar
  • 23 Steele J CP, Warhurst D C, Kirby G C, Simmonds M SJ. In vitro and in vivo evaluation of betulinic acid as an antimalarial.  Phytotherapy Research. 1999;  13 115-9
    CrossrefPubMedSearch in Google Scholar
  • 24 Samuel B U, Mohandas N, Harrison T, McManus H, Rosse W, Reid M, Haldar K. The role of cholesterol and glycosylphosphatidylinositol-anchored proteins of erythrocyte rafts in regulating raft protein content and malarial infection.  Journal of Biological Chemistry. 2001;  276 29 319-29
    PubMedSearch in Google Scholar
  • 25 Han S K, Ko Y I, Park S J, Jin I J, Kim Y M. Oleanolic acid and ursolic acid stabilize liposomal membranes.  Lipids. 1997;  32 769-73
    PubMedSearch in Google Scholar

Dr. Dan Stærk

Department of Medicinal Chemistry

The Danish University of Pharmaceutical Sciences

Universitetsparken 2

2100 Copenhagen

Denmark

Fax: +45 3530 6040

Email: ds@dfh.dk