Pinosylvin dimethyl ether and three other stilbene ethers were prepared by condensing the appropriate diethylbenzylphosphonates with an aromatic aldehyde. Cleavage of pinosylvin dimethyl ether with boron tribromide gave in good yield the monomethyl ether, while fusion with pyridine hydrochloride yielded pinosylvin.
On 2% malt extract agar media containing 10% lodgepole pine heartwood meal, laccase-producing Peniophora pseudo-pini Weres. & Gibson and Fomes pini (Thore ex Fr.) Lloyd survived 400 p.p.m. of dispersed non-solvated pinosylvin, double the lethal dose of pinosylvin for these fungi on 2% malt extract agar. Non-laccase-producing Coniophora puteana Schum. ex Fr. survived 200 p.p.m. of pinosylvin on 2% malt extract agar containing 10% heartwood meal. The lethal dose of pinosylvin for C. puteana on 2% malt extract agar was 50 p.p.m.On 2% malt extract agar and on 2% malt extract containing 1% cellobiose, 200 p.p.m. of the flavanone pinocembrin permitted the survival of P. pseudo-pini in the presence of 200 p.p.m. of pinosylvin. F. pini survived 200 p.p.m. of pinosylvin on 2% malt extract agar containing 1% cellobiose. This fungus survived when 200 p.p.m. of the flavanone pinocembrin were added to 200 p.p.m. of pinosylvin on 2% malt extract agar.
The heartwood of lodgepole pine (Pinus contorta Dougl. var. latifolia Engelm.) contains considerable amounts of fungitoxic phenolics, but also possesses an extensive fungus flora. Two of the most frequently isolated fungi, Peniophora pseudo-pini Weres. & Gibson and Tympanis hypopodia Nyl., effected the most rapid decrease in concentration of pinosylvin, pinosylvinmonomethyl ether, pinocembrin, and pinobanksin in lodgepole pine heartwood meal. Three mechanisms for the removal of pinosylvin were observed. The laccase-producing ascomycetes, Coryne sarcoides (Dicks. ex Fr.) Bon. and T. hypopodia, caused a decrease in optical density as well as a maximum absorption shift of pinosylvin from 310 mμ to 300 mμ. This shift could be related to the appearance of a new compound which absorbed at 300 mμ. Three laccase-producing basidiomycetes, P. pseudo-pini, Stereum sanguinolentum Alb. & Schw. ex Fr., and Fomes pini (Thore ex Fr.) Lloyd, caused decreases in the concentration of pinosylvin that were concurrent with red stain formation in infected heartwood meal, but were not associated with maximum absorption shifts. The non-laccase-producing brown rot fungus, Coniophora puteana Schum. ex Fr., caused a maximum absorption shift of pinosylvin from 310 to 320 mμ. However, the concentration of altered pinosylvin did not decrease below that of pinosylvin in the control. All fungi were living at the conclusion of the experiment.
In an investigation to determine the fungal flora of lodgepole pine logging slash and the growth rates and decaying abilities of the principal fungi in vitro as contrasted with conditions in nature, four hymenomycetes were isolated consistently and proved to cause most of the decay; Lenzites saepiaria Wulf. ex Fr., Peniophora phlebioides Jacks. and Dearden, Stereum sanguinolentum Alb. and Schw. ex Fr., and Coniophora puteana (Schum. ex Fr.) Karst. These four fungi comprised 80% of the basidiomycetes isolated from slash. Peniophora phlebioides predominated in the upper portions of individual pieces of slash, Lenzites saepiaria in the center, and Coniophora puteana and Stereum sanguinolentum in the lower portions. Relatively broad temperature ranges and high temperature optima were demonstrated for P. phlebioides and L. saepiaria to grow and cause decay, in contrast with the narrower temperature ranges and lower optimal temperatures demonstrated for C. puteana and S. sanguinolentum. The internal temperatures of slash were proved to fluctuate between wider extremes in the upper portions of slash than in the lower portions. This is believed to be a partial explanation of the characteristic distributions of individual fungi within slash. The relative decaying abilities of the four main fungi as indicated by wood block tests, in decreasing order of importance were: L. saepiaria, C. puteana, P. phlebioides, S. sanguinolentum. Because of its greater frequency, however, P. phlebioides probably ranks higher in the scale of slash decayers than C. puteana.
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