Fernene Triterpenoids from the Lichen Pyxine berteriana

MARTA S. MAIER; MARÍA L. ROSSO; ALEJANDRA T. FAZIO; MÓNICA T. ADLER; MARÍA D. BERTONI

JOURNAL OF NATURAL PRODUCTS

American Chemical Society and American Society of Pharmacognosy

Año: 2009 vol. 72 p. 1902 - 1904

0163-3864

Two new fernene triterpenoids, fern-9(11)-en-3,19-dione (1) and 3
-acetoxyfern-9(11)-en-19-one (2), together with the known 3
-acetoxyfern-9(11)-en-19
-ol (3) and lichexanthone (4), have been isolated from the acetone extract of the lichen Pyxine berteriana. The structures of the new compounds were established on the basis of IR, extensive 1D and 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. lichen Pyxine berteriana. The structures of the new compounds were established on the basis of IR, extensive 1D and 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. lichen Pyxine berteriana. The structures of the new compounds were established on the basis of IR, extensive 1D and 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. lichen Pyxine berteriana. The structures of the new compounds were established on the basis of IR, extensive 1D and 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. lichen Pyxine berteriana. The structures of the new compounds were established on the basis of IR, extensive 1D and 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. lichen Pyxine berteriana. The structures of the new compounds were established on the basis of IR, extensive 1D and 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. 2D NMR, and MS analyses. Although several fern-9(11)-enes have been isolated from lichens, compounds 1 and 2 are the first examples of naturally occurring fernene triterpenoids with a carbonyl function at C-19. the first examples of natura