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Chemical profiling of Phlomis thapsoides (Lamiaceae) and in vitro testing of its biological activities

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Abstract

A phytochemical study of Phlomis thapsoides (Lamiaceae) resulted in the isolation of one new compound, 6,10,17-trimethyl-2-octadecanone, and three known compounds (sitosterol-3-O-β-glucoside, and the iridoid glucosides ipolamiide and lamiide). The structures of the isolated compounds were elucidated using mass spectrometry, 1D/2D NMR spectroscopy experiments in comparison with published data. The chemical composition of the essential oil obtained from aerial parts of P. thapsoides was determined by gas liquid chromatography and gas liquid chromatography-mass spectroscopy. The main volatile constituents were phenylethyl alcohol (6.81 %), trans-3-hexenol (5.55 %), 1-octen-3-ol (5.10 %), α-cadinol (4.92 %), and α-muurolol (4.67 %). The antioxidant activity of the extracts was evaluated by three methods: 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activity, 2,2′-azinobis-[3-ethylbenzthiazoline-6-sulfonic acid] and ferric reducing antioxidant power assay along with the determination of total phenolic content. Although the ethyl acetate extract contained 362.06 mg of gallic acid equivalents, the antioxidant activities, as revealed by 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azinobis-[3-ethylbenzthiazoline-6-sulfonic acid] and ferric reducing antioxidant power assays, were of medium strength (IC50 of 73.08 ± 3.18, 9.48 ± 0.71 µg/mL and 9.33 ± 0.17 mM of FeSO4 equivalents, respectively). Only lamiide inhibited soybean 5-lipoxygenase with an IC50 value of 72.92 µg/mL in vitro. In-silico molecular modeling studies on 5-lipoxygenase and human 5-lipoxygenase-activating protein were used to evaluate the potential anti-inflammatory activity. Sitosterol-3-O-β-glucoside followed by the iridoid glucoside lamiide exhibited the highest inhibition of 5-lipoxygenase whereas the new compound 6,10,17-trimethyl-2-octadecanone and sitosterol-3-O-β-glucoside exhibited the highest inhibition of 5-lipoxygenase-activating protein as evidenced from their higher fitting scores. The cytotoxicity of the plant extracts and lamiide against Caco2 and HepG-2 cancer cells resulted in IC50 values of >100 µg/mL indicating a low cytotoxicity.

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Acknowledgments

The authors would like to thank the DAAD for a scholarship to N.Z. Mamadalieva and the Egyptian government for providing financial support for T. Mohamed. The authors express their special thanks to Dr. M.G. Levkovich, Dr. K. Bobakulov and Mr. T. Timmermann for their help recording NMR spectrum and to Dr. Olim Nigmatullaev for collecting the plant materials. Part of this study was funded through a grant from the Republic of Uzbekistan State Foundation for Basic Research (Grant No. FA-F6-Т-209).

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Authors and Affiliations

  1. Institute of Pharmacy and Molecular Biotechnology, Heidelberg University, Im Neuenheimer Feld 364, 69120, Heidelberg, Germany

    Mansour Sobeh, Tamer Mohamed, Sonja Krstin & Michael Wink

  2. Laboratory of Chemistry of Glycosides, Institute of the Chemistry of Plant Substances AS RUz, Tashkent, 100170, Uzbekistan

    Nilufar Z. Mamadalieva & Shahnoz S. Azimova

  3. Department of Pharmacognosy, Faculty of Pharmacy, Ain Shams University, Organization of African Unity Street, Abbasia, 11566, Cairo, Egypt

    Fadia S. Youssef & Mohamed L. Ashour

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  1. Mansour Sobeh
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  2. Nilufar Z. Mamadalieva
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  3. Tamer Mohamed
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  5. Fadia S. Youssef
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  6. Mohamed L. Ashour
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  7. Shahnoz S. Azimova
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  8. Michael Wink
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Correspondence to Michael Wink.

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Sobeh, M., Mamadalieva, N.Z., Mohamed, T. et al. Chemical profiling of Phlomis thapsoides (Lamiaceae) and in vitro testing of its biological activities. Med Chem Res 25, 2304–2315 (2016). https://doi.org/10.1007/s00044-016-1677-9

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  • DOI: https://doi.org/10.1007/s00044-016-1677-9

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