Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre
Seven new metabolites, 3-hydroxy-1-(2,6-dihydroxyphenyl)butan-1-one (1), 1-(2-hydroxy-6-methoxyphenyl)butan-1-one (3), 2,3-dihydro-5-methoxy-2-methylchromen-4-one (6), the dimeric naphthalenes nodulisporin A (9) and B (10), and the first naturally occurring dimeric indanone, nodulisporin C (12), as well as (4E,6E)-2,4,6-trimethylocta-4,6-dien-3-one (13) were isolated together with ten known compounds (2, 4, 5, 7, 8, 11, 14–17) from the culture extract of the endophytic fungus Nodulisporium sp. from Juniperus cedre from Gomera Island. The structure of dictafolin-A, previously erroneously assigned as structure 6, is not identical with 2,3-dihydro-5-methoxy-2-methylchromen-4-one, isolated in this investigation. The structures of new compounds were determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and mass spectral measurements) and X-ray single crystal analysis. All but one of the thirteen tested compounds exhibit herbicidal, antifungal and/or antibacterial activities. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)