Investigation of Antiplasmodial Effects of Terpenoid Compounds Isolated from Myrrh

Hippolyt L. Greve; Marcel Kaiser; Thomas J. Schmidt

doi:10.1055/a-1157-9463

Planta Medica, Table of Contents

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

¹Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany

,

Marcel Kaiser

²Swiss Tropical and Public Health Institute, Basel, Switzerland

³University of Basel, Basel, Switzerland

,

Thomas J. Schmidt

¹Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany

› Author Affiliations

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

Full Text

References

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