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Alkyl phenols, alkenyl cyclohexenones and other phytochemical constituents from Lannea rivae (chiov) Sacleux (Anacardiaceae) and their bioactivity

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Abstract

Six novel compounds, 3-nonadec-14′-(Z)-enyl phenol (1a); 4,5-dihydroxy-4,2′-epoxy-5-[16′-Z-18′-E-heneicosenyldiene]-cyclohex-2-enone (2), 2,4,5-trihydroxy-2-[16′-Z-heneicosenyl]-cyclohexanone (3); 4S,6R-dihydroxy-6-[12′-Z-heptadecenyl]-cyclohex-2-enone (4a); 4S,6R-dihydroxy-6-[14′-Z-nonadecenyl]-cyclohex-2-enone (4b); and 1,2,4-trihydroxy-4-[16′-Z-heneicosenyl]-cyclohexane (5) were identified from the roots and stems of Lannea rivae in addition to the known cardanols, 3-heptadec-12′-Z-enyl phenol (1b), 3-pentadec-10′-Z-enyl phenol (1c) and 3-pentadecyl phenol (1d), sitosterol (6), sitosterol glucoside (7), taraxerone (8), taraxerol (9), E-lutein (10), myricetin (11), myricetin-3-O-α-rhamnopyranoside (12), myricetin-3-O-β-galactopyranoside (13) and (-)-epicatechin-3-O-gallate (14). The ketones 4a and 4b were isolated as a mixture and were qualitatively separated and identified by GCMS. Myricetin (11) and epicatechin gallate (14) displayed over 90 % DPPH radical-scavenging activity at 50 μg mL−1, while its glycosides (12 and 13) showed percentages of over 70 % in the same assay. The same compounds 11 and 14 showed antibacterial activity similar to erythromycin and vancomycin against Gram-positive bacteria and were also active against Gram-negative bacteria, but not as much as the cefuroxime, ciprofloxacin and nalidixic acid standards. Compounds 1a–d, 4a–b and 5 were all relatively non-toxic, while 2 (the epoxy cyclohex-2-enone) and 3 (the trihydroxy cyclohexanone) showed more toxicity than the others. These two toxic compounds, 2 and 3 also showed antiplasmodial activity with IC50 values between 0.48 and 2.05 μg mL−1. The mixture of dihydroxy cyclohex-2-enones 4a and 4b, which was far less toxic than 2 and 3, also showed promising antiplasmodial activity and may be a possible lead for further investigation as an antiplasmodial drug.

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Acknowledgments

The authors are grateful to TWOWS for financial assistance. We also thank Mr. Philip Apamo and Mr. Charles Maasai of the Center for Disease Control, Kisian, Kenya, for technical assistance with antibacterial assays. We thank Prof. Peter Smith of Stellenbosch University for conducting cytotoxicity assays. Lastly, we thank Ms. Agnes Cheruiyot, Mr. Charles Okudo and Ms. Redemptah Yeda for Plasmodium falciparum culture and sensitivity testing.

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  1. School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, South Africa

    Dorothy A. Okoth & Neil A. Koorbanally

  2. Department of Emerging Infectious Diseases, United States Army Medical Research Unit-Kenya (USAMRU-K), Kenya Medical Research Institute (KEMRI)/Walter Reed Project, P.O. Box 54, Kisian-Kisumu, Kenya

    Hoseah M. Akala & Jacob D. Johnson

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  1. Dorothy A. Okoth
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Okoth, D.A., Akala, H.M., Johnson, J.D. et al. Alkyl phenols, alkenyl cyclohexenones and other phytochemical constituents from Lannea rivae (chiov) Sacleux (Anacardiaceae) and their bioactivity. Med Chem Res 25, 690–703 (2016). https://doi.org/10.1007/s00044-016-1521-2

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