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Planta Med 2020; 86(09): 643-654
DOI: 10.1055/a-1157-9463
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Investigation of Antiplasmodial Effects of Terpenoid Compounds Isolated from Myrrh

Hippolyt L. Greve
1   Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany
,
Marcel Kaiser
2   Swiss Tropical and Public Health Institute, Basel, Switzerland
3   University of Basel, Basel, Switzerland
,
Thomas J. Schmidt
1   Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany
› Author AffiliationsSupported by: Apothekerstiftung Westfalen-Lippe
Further Information

Publication History

received 02 December 2019
revised 25 March 2020

accepted 04 April 2020

Publication Date:
04 May 2020 (online)

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Abstract

As part of our ongoing search for antiprotozoal natural products from plants, we examined different resins from the Burseraceae family. The dichloromethane extract obtained from myrrh, the oleo-gum-resin of Commiphora species, showed promising in vitro activity against Plasmodium falciparum with an IC50 value of 1 µg/mL. Bioactivity-guided fractionation led to the isolation and characterization of 18 sesquiterpenoids, namely, β-elemene (1), elemyl acetate (2), curzerenone (3), 8-hydroxyisogermafurenolide (4), 2-methoxyisogermafurenolide (5), 8-epi-2-methoxyisogermafurenolide (6), furanodienone (7), 1(10)Z,4Z-furanodien-6-one (8), rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (9), (1(10)E)-2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one (10), 2R-methoxyfuranodiene (11), 2-acetyloxyglechomanolide (12), 8-epi-2-acetyloxyglechomanolide (13), (1R,2R,4S)-1,2-epoxyfuranogermacr-10(15)-en-6-one (14), hydroxylindestrenolide (15), isohydroxylindestrenolide (16), myrrhone (17), and myrrhterpenoid O (18). Moreover, nine (nor-)triterpenoids were isolated: mansumbinol (19), mansumbinol epoxide (20), mansumbinone (21), mansumbin-13(17)-en-3,16-dione (22), 3,4-seco-mansumbinoic acid (23), rel-20S-hydroxy-dammar-24-en-3,16-dione (24), rel-(16S,20S)-dihydroxydammar-24-en-3-one (25), cycloart-24-en-1α,2α,3β-triol (26), and 3β-isovaleroyloxycycloart-24-en-1α,2α-diol (27). All compounds were identified by MS and NMR spectroscopic analyses. To the best of our knowledge, compounds 5, 6, 12, 13, 16, 18, and 20 are reported for the first time. All isolated compounds were tested in vitro for activity against P. falciparum and cytotoxicity. The sesquiterpene 7 and the triterpene 25 were the most active compounds found in this study with IC50 values of 7.4 and 2.8 µM, respectively.

Key words

Myrrh - Commiphora - Plasmodium falciparum - antiprotozoal activity - Burseraceae - terpenoids

Supporting Information

    Analytical data of known compounds in comparison with literature data, bioactivity data of extracts and main fractions (Tables 1S–3S), spectroscopic data and molecular models with key NOESY correlations for compounds 5, 6, 12, 13, 15, 16, 18, 20, and 24 (Figs. 1S–48S; copies of further original spectra are available from the corresponding author), and dose-effect diagrams from the biological tests of all compounds for antiplasmodial and cytotoxic activity (Figs. 49S and 50S, respectively) are available as Supporting Information.

  • Supporting Information
 

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