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A Novel Normethylfriedelane-Type Isoprenoid from Syzygium guineense Stem Bark

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Chemistry of Natural Compounds Aims and scope

Isolated from the n-hexane soluble fraction of the chloroform extract of Syzygium guineense stem bark were two friedelane-type isoprenoids, friedelan-3-one (1) and a novel derivative 12-hydroxy-27-normethylfriedelan-3-one (2). Mass, NMR (1- and 2-D), and FTIR spectroscopic techniques were used for structural elucidation. GC-MS analysis of the lipoidal column eluate afforded the known isoprenoids γ-sitosterol (3) and olean-12-en-3-one (4) and the two fatty acids n-hexadecanoic acid (5) and octadecanoic acid (6). This is the first report on the phytochemistry and isolation of the novel 12-hydroxy-27-normethylfriedelan-3-one (2) from the stem bark of this plant. The pharmacological and nutritional profiles of these isoprenoids and fatty acids are highlighted.

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Acknowledgment

The authors thank Prof. Ian Catros-Gamboa of the Sao Paulo State University, Araraquara, Brazil for making their NMR facilities available and accessible, the Sao Paulo Research Foundation (FAPESP) for a conference traveling grant award to the corresponding author to attend the 2013 Sao Paulo Advanced School of Bio-organic Chemistry (ESPCA) in Brazil that made it possible for him to meet Prof. Ian Catros-Gamboa, and the ICCBS, Pakistan where the mass spectroscopic analysis was done.

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Authors and Affiliations

  1. Department of Chemistry, University of Ibadan, Ibadan, Nigeria

    I. A. Oladosu & O. O. Aiyelaagbe

  2. Department of Pharmacognosy and Phytotherapy, University of Port-Harcourt, P.M.B 5324, Choba, Port Harcourt, 50004, Nigeria

    O. E. Afieroho

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  1. I. A. Oladosu
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  2. O. O. Aiyelaagbe
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  3. O. E. Afieroho
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Corresponding author

Correspondence to O. E. Afieroho.

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Published in Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2018, pp. 97–100.

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Oladosu, I.A., Aiyelaagbe, O.O. & Afieroho, O.E. A Novel Normethylfriedelane-Type Isoprenoid from Syzygium guineense Stem Bark. Chem Nat Compd 54, 112–116 (2018). https://doi.org/10.1007/s10600-018-2271-9

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  • DOI: https://doi.org/10.1007/s10600-018-2271-9

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