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 compou...

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Published in:Natural product research 2024-07, p.1-10
Main Authors: Njindi Kouotou, Mohamar JR, Nsangou, Mohamed Foundikou, Kenmogne, Sidonie Beatrice, Tcho, Alain Tadjong, Peyeino, Jules Hugues, Sikam, Klev Gaitan, Mandou Michiren, Vanini Samiyatou, Happi, Emmanuel Ngeufa, Songue, Jules Lobe, Toze, Flavien Aristide Alfred
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Language:English
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Summary: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.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.
ISSN:1478-6419
1478-6427
1478-6427
DOI:10.1080/14786419.2024.2372664