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Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre

2006; Wiley; Volume: 2006; Issue: 15 Linguagem: Inglês

10.1002/ejoc.200600261

1434-193X

Jingqiu Dai, Karsten Krohn, Ülrich Flörke, Siegfried Draeger, Barbara Schulz, Attila Kiss‐Szikszai, Sándor Antus, Tibor Kurtán, Teunis van Ree,

Bioactive natural compounds

Abstract 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 (4 E ,6 E )‐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)