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Antifungal eudesmanoids from Parthenium argentatum x P. tomentosa

1996; Elsevier BV; Volume: 41; Issue: 2 Linguagem: Inglês

10.1016/0031-9422(95)00580-3

1873-3700

Galal T. Maatooq, David K. Stumpf, Joseph J. Hoffmann, Louis K. Hutter, Barbara N. Timmermann,

Natural product bioactivities and synthesis

Investigation of guayule resin for antifungal activity has led to the isolation and characterization of six eudesmane-type sesquiterpenoids, five of which are new: 2-methoxy-eudesma-1,4,6-trien-3-one (argentone); 2-methoxy-15-nor-eudesma-1,4,6-trien-3-one (15-nor-argentone); 2-methoxy-15-hydroxy-eudesma-1,4,6-trien-3-one (15-hydroxy-argentone); 2-methoxy-eudesma-1,4,6-trien-3,8-dione (8-oxo-argentone); 2-methoxy-15-nor-eudesma-1,4,6-trien-3,8-dione (8-oxo-15-nor-argentone); and the previously identified 11-hydroxy-eudesma-4-en-3-one (carissone). Their structures were elucidated by one- and two-dimensional NMR spectroscopy and mass spectrometry. After 6 weeks all inhibited the growth of Aspergillus fumigatus (ATCC-13073) at 1.0 mg ml− 1 and complete inhibition of A. niger (UA-172-1) for 2-methoxy-eudesma-1,4,6-trien-3-one and 2-methoxy-15-nor-eudesma-1,4,6-trien-3-one. At 0.25 mg ml− 1 2-methoxy-eudesma-1,4,6-trien-3-one demonstrated 100% control against A. fumigatus and 80% control against A. niger.