Metabolites from the endophytic fungus Nodulisporium sp firom 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. ((c) Wiley-VCH Verlag GmbH & Co. KGdA, 69451 Weinheim, Germany, 2006)