Phellinus tremulae

Methoxycarbonylbenzene oxide (48), the valence tautomer of 2-methoxycarbonyloxepin, was isolated from liquid cultures of wood-rotting fungus Phellinus tremulae <93TL1589>. 

CgHgOg, Mr 152.15, liquid. A metabolite from cultures of the fungus Phellinus tremulae (Basidiomycetes). According to its h NMR spectrum the compound exists as an equilibrium mixture with its valence tautomer methyl 1,6-epoxy-2,4-cyclohexadiene-1 -carboxylic... 

Phellinus tremulae (Bond.) Bond Boriss. = Fomes igniarius (L. Fr.) Kickx. Pholiota destruens (Brond.) Quel. 

When grown in liquid medium Phellinus tremulae produced 2-carbomethoxyoxepin (70), the precursor of methyl salicylate, and a... 

Chart 12. The metabolites of the aspen rotting fungus Phellinus tremulae... 

The new fungus Phoma etheridgei isolated from black galls of aspen was known to be strongly antagonistic to the aspen decay fungus Phellinus tremulae. The bioassay guided isolation of metabolites from... 

Trifonov, L.S., P. Chakravarty, Y. Hiratsuka, and W.A. Ayer Antifugal activity of metabolites of Peniophora polygonia against the aspen decay fungus Phellinus tremulae. Eur. J. For. Path. 22, 441 (1992). 

Ayer, W.A., and E.R. Cruz The tremulanes, a new group of sesquiterpenes from the aspen rotting fungus Phellinus tremulae. J. Org. Chem. 58, 7529 (1993). 

Cruz, E.R. The biosynthesis of the new tremulene sesquiterpenes isolated from Phellinus tremulae. Can. J. Chem. 75, 834 (1997). 

Crane, P.E., P.V. Blenis, and Y. Hiratsuka Black stem galls on aspen and their relationship to decay by Phellinus tremulae. Canad. J. For. Res. 24, 2240 (1994). 

Isol. from cultures of Phellinus tremulae. Proposed biogenetic precursor of methyl salicylate. Yellow oil. Po.o2 48-50°. 

There is strong evidence that the biosynthesis of salicylic acid 75 from benzoic acid 72 by the fungus Phellinus tremulae runs via an arene oxide 73 [36] (Fig. 12). The mechanism is principally the same as that for naphthalene and quinoline, but in this case the rearrangement product 2-carbomethoxyoxepin 74 was also found in the supernatant of the fungus. 

Figure 12 Biosynthesis of salicyclic acid from benzoic in Phellinus tremulae.

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