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

Majid Sairafianpour; Babak Bahreininejad; Matthias Witt; Hanne L. Ziegler; Jerzy W. Jaroszewski; Dan Stærk

doi:10.1055/s-2003-43212

Planta Medica, Table of Contents

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

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

Full Text

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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