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

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  μ g/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.