Maghamesin, a new prenylated flavanone from artocarpus heterophyllus lam. (moraceae)

Abstract

The chemical investigation of the methanol root extract of Artocarpus heterophyllus Lam. led to the isolation of a new prenylated flavanone, 5,7,4′-trihydroxy-3′-(3-methylbuta-1,3-dienyl)-5′-(3-methylbut-2-enyl)flavanone, trivially named maghamesin (1), together with nine known compounds, 5-hydroxy-3’,4’,5’,7-tetramethoxy-8-prenylflavanone (2), cycloheterophyllin (3), cyclomorusin (4), isobavachalcone (5), trans-isoferulic acid (6), 24-methylenecycloartan-3α-ol (7), stigmasterol (8), β-sitosterol (9) and β-sitosterol-3-O-β-D-glucopyranoside (10). The structures of the isolates were elucidated by extensive spectroscopic and spectrometric analyses (1D and 2D NMR, ESI-MS) and by comparison with previously reported data. The absolute configuration of 1 was deduced by comparison of its experimental CD with that of a reported similar compound. Compounds 1-3 and 6-7 were tested for their antibacterial and antifungal activities. Compound 1 displayed a significant antibacterial activity against Staphylococcus aureus with MIC value of 15.625 μg/mL. The others tested compounds showed moderate antibacterial and antifungal activities against several microorganisms with MIC values of either 31.25 or 62.5 μg/mL.

Graphical Abstract

Keywords:

• Artocarpus heterophyllus lam
• moraceae
• prenylated flavanone
• antibacterial activity
• antifungal activity

Acknowledgement

The authors acknowledge the laboratory of Chemistry of the University of Douala for its supports.

Author’s contributions

Conceptualisation, M.J.N.K., M.F.N., A.T.T., S.B.K, J.L.S, F.A.A.T.; Formal analysis, M.F.N., K.G.S., A.T.T.; Methodology, M.J.N.K., M.F.N., A.T.T., J.H.P., K.G.S., V.S.M.M. S.B.K., E.N.H.; writing—original draft preparation, M.F.N., A.T.T., K.G.S., F.A.A.T, writing—review and editing, All the authors. All authors have read and agreed to the published version of the manuscript.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Data availability statement

The datasets supporting this article have been uploaded as part of the Electronic Supplementary Material.

Figure 1. Structures of compounds 1-10 from the methanol root extract of A. heterophyllus.

Additional information

Funding

The author(s) reported there is no funding associated with the work featured in this article.