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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
1   Institute for 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
,
Reto Brun
2   Swiss Tropical and Public Health Institute, Basel, Switzerland
3   University of Basel, Basel, Switzerland
,
Thomas J. Schmidt
1   Institute for Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany
› Author Affiliations
Further Information

Publication History

received 16 May 2017
revised 07 July 2017

accepted 13 July 2017

Publication Date:
24 July 2017 (online)

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Erratum: Terpenoids from the Oleo-Gum-Resin of Boswellia serrata and Their Antiplasmodial Effects In VitroPlanta Med 2017; 83(14/15): E4-E4
DOI: 10.1055/s-0043-118649

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

Supporting Information

    Bioactivity data of extracts and main fractions are available in the Supporting Information (Table 1S) as well as NMR spectra and molecular models with key NOESY correlations for 6 + 7 and 11–18 (Fig. 1S–71S, Supporting Information). Copies of further original spectra are available from the corresponding author. Dose-effect diagrams from the biological tests of all compounds for antiplasmodial and cytotoxic activity are also available as Supporting Information (Figs. 72S and 73S, respectively).

  • Supporting Information
 

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