Terpenoids from the Oleo-Gum-Resin of Boswellia serrata and Their Antiplasmodial Effects In Vitro

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

doi:10.1055/s-0043-116943

Planta Medica, Inhaltsverzeichnis

Planta Med 2017; 83(14/15): 1214-1226
DOI: 10.1055/s-0043-116943

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Terpenoids from the Oleo-Gum-Resin of Boswellia serrata and Their Antiplasmodial Effects In Vitro

Hippolyt L. Greve

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

,

Marcel Kaiser

²Swiss Tropical and Public Health Institute, Basel, Switzerland

³University of Basel, Basel, Switzerland

,

Reto Brun

²Swiss Tropical and Public Health Institute, Basel, Switzerland

³University of Basel, Basel, Switzerland

,

Thomas J. Schmidt

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

› Institutsangaben

Abstract

In the course of our ongoing search for new natural products as leads against protozoal diseases, the dichloromethane extract of Indian frankincense, the oleo-gum-resin obtained from Boswellia serrata, showed in vitro activity against Plasmodium falciparum. Bioactivity-guided fractionation led to the isolation of eight diterpenes: (1S,3E,7E,11R)-verticilla-3,7,12(18)-triene (1), cembrene A (2), serratol (3), 1S,3E,7R,8R,11E-7,8-epoxy-cembra-3,11-dien-1-ol (4), incensole oxide (5), rel (1S,3R,7E,11S,12R)-1,12-epoxy-4-methylenecembr-7-ene-3, 11-diol (6), isoincensole oxide (7), and isodecaryiol (8). Furthermore, 10 triterpenes, namely, oleanolic acid (9), 11-keto-β-boswellic acid (10), 3-epi-neoilexonol (11), uvaol (12), β-boswellic aldehyde (13), 5α-tirucalla-8,24-dien-3α-ol (14), isoflindissone lactone (15), isoflindissol lactone (16), rel (8R,9S,20R)-tirucall-24-ene-3β,20-diol (17), and rel (3α,8R, 9S,20R,24S)-20,24-epoxytirucalla-3,25-diol (18) as well as the sesquiterpene β-bourbonene (19), the monoterpene carvacrol (20) and the phenyl propanoids methyleugenol (21), and p-methoxycinnamaldehyde (22) were isolated. All compounds were identified by mass spectrometry and nuclear magnetic resonance spectroscopic measurements. Compounds 6, 11, and 16–18 are described for the first time. Compounds 13 – 15 are isolated as natural products for the first time, compound 8 for the first time from a plant. Antiplasmodial IC₅₀ values and cytotoxicity against L6 rat skeletal myoblasts were determined. Isoflindissone lactone (15) was the most active compound with an IC₅₀ of 2.2 µM against P. falciparum and a selectivity index of 18.

Key words

Boswellia serrata - Plasmodium falciparum - antiprotozoal activity - Burseraceae - diterpenes - triterpenes

Volltext

Referenzen

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