Synthesis of (+/−) arthrographol

1991 ◽  
Vol 69 (12) ◽  
pp. 1909-1916 ◽  
Author(s):  
William A. Ayer ◽  
Peter A. Craw

A total synthesis of (+/−) arthrographol (1) in seven steps from vanillin is reported. Key steps in the synthesis are a single-step conversion of 5-allylvanillin (2) into the benzofuranmethanol 6, alkylation of the chloride 25 with the lithium anion of crotyl phenyl sulfide to give the sulfide 26, and formation of the 1(E),3(E)-1,3-pentadienyl side chain of arthrographol (1) via oxidation of the sulfide 26 and subsequent elimination of phenylsulfenic acid. The synthetic (+/−) arthrographol (1) inhibits the growth of Ophiostoma clavigerum (Robin.-Jeff. & Davids.) Harrington, the most pathogenic of the fungi associated with the blue stain disease of lodgepole pine (Pinus contorta Dougl. var latifolia Engelm.). Key words: arthographol, alkylation, 2-butenyl phenyl sulfide, polyketide.

1990 ◽  
Vol 36 (2) ◽  
pp. 77-82 ◽  
Author(s):  
Lynne Sigler ◽  
Yuichi Yamaoka ◽  
Yasuyuki Hiratsuka

Arthrographis pinicola sp.nov. (Hyphomycetes) is described; it was isolated from galleries and adult beetles of Ips latidens and from galleries of Dendroctonus ponderosae in Pinus contorta var. latifolia in western Canada. In I. latidens infested lodgepole pine, this species extensively colonizes nuptial chambers and egg galleries, characteristically forming floccose conidiomata composed of repeatedly branched hyphae which divide to form arthroconidia having schizolytic dehiscence. The fungus is antagonistic to some blue stain fungi in vitro. Arthrographis pinicola is compared with other species of Arthrographis, and with Arthropsis microsperma and the discomycete Pezizella chapmanii. Key words: Arthrographis pinicola, Hyphomycetes, bark beetle fungi, antifungal compound, arthrographol.


1987 ◽  
Vol 65 (1) ◽  
pp. 95-102 ◽  
Author(s):  
H. S. Whitney ◽  
R. J. Bandoni ◽  
F. Oberwinkler

A new basidiomycete, Entomocorticium dendroctoni Whitn., Band. & Oberw., gen. et sp. nov., is described and illustrated. This cryptic fungus intermingles with blue stain fungi and produces abundant essentially sessile basidiospores in the galleries and pupal chambers of the mountain pine bark beetle (Dendroctonus ponderosae Hopkins Coleoptera: Scolytidae) in lodgepole pine (Pinus contorta Dougl. var. latifolia Engelm.). The insect apparently disseminates the fungus. Experimentally, young partially insectary reared adult beetles fed E. dendroctoni produced 19% more eggs than beetles fed the blue stain fungi.


1971 ◽  
Vol 103 (11) ◽  
pp. 1495-1503 ◽  
Author(s):  
H. S. Whitney

AbstractThe physical association between Dendroctonus ponderosae Hopk. and its associated blue stain fungi Ceratocystis montia Rumb. and Europhium clavigerum Robinson and Davidson and the yeasts Pichia pini (Holst) Phaff, Hansenula capsulata Wickerham, and H. holstii Wickerham is described in single broods reared in bolts of lodgepole pine, Pinus contorta Dougl. var. latifolia Engelm. Eggs just prior to hatch and first-instar larvae were always in contact with the microorganisms whereas newly laid eggs, second-, third-, and fourth-instar larvae were not. During pupation, blue stain fungi and yeasts colonized pupal chamber walls. Transfer of these microorganisms to the new generation of insects was ensured when tenerals contacted the microorganisms lining the pupal chamber. Ensured physical contact between these organisms supports the hypothesis of a symbiosis between them.


1984 ◽  
Vol 62 (8) ◽  
pp. 1724-1729 ◽  
Author(s):  
R. G. Ballard ◽  
M. A. Walsh ◽  
W. E. Cole

The growth of blue-stain fungi was investigated in naturally blue-stained lodgepole pine (Pinus contorta var. latifolia Engelm.) sapwood. Events occurring at the leading edge of hyphal penetration were studied. Fungi are initially confined to the sapwood rays. Hyphae readily penetrate the primary cell walls of ray parenchyma cells and proliferate within. Hyphae also grow freely in the region of the middle lamella of the rays. Host cell walls are breeched mechanically by a penetration peg originating from an appressoriumlike structure. Eventually, hyphae enter tracheids by penetrating the primary cell walls of pinoid, half-bordered pit pairs. Within the tracheid, fungal hyphae grow in a longitudinal fashion, branching infrequently. Hyphae may pass from tracheid to tracheid via bordered pit pairs. Ensuing water stress and eventual tree death is discussed in light of histological evidence presented.


1989 ◽  
Vol 65 (1) ◽  
pp. 36-41 ◽  
Author(s):  
R. J. Nevill ◽  
J. H. Borden ◽  
H. Merler

In a stand of 45-65-year old lodgepole pine, Pinus contorta Dougl. var. latifolia Engelm., in the interior of British Columbia, Atropellis canker, Atropellis piniphila (Weir) Lohman and Cash, and stalactiform blister rust, Cronartium coleosporioides Arth., reduced the volume of infected trees by 7.9% and 6.2%, respectively. Manufacture of lumber from these trees increased volume losses by up to 28.7% and 26.4%, respectively. Atropellis canker reduced the volume of Standard and Better grade lumber by up to 40.1% and stalactiform blister rust by 33.3%, with corresponding relative increases in the volume of Utility grade up to 80%. The reduction of lumber volume and grade decreased the value of Atropellis-infected trees by 33.4% and stalactiform blister rust-infected trees by 28.7%. Based on the density of stems per hectare and infection rates, the two diseases reduced the potential lumber value of lodgepole pine by $508.40 per hectare. Thus management measures to reduce the incidence and impact of these diseases may be economically justified. Key Words: Lodgepole pine; Pinus contorta; Atropellis piniphila, Cronartium coleosporioides; lumber volume, grade, value.


1991 ◽  
Vol 69 (5) ◽  
pp. 853-855 ◽  
Author(s):  
Nada Stojanac ◽  
Zdenek Valenta

The completion of the total synthesis of d,l-quassin 1 is described. Key steps are a facile intramolecular acylation of a protected cyanohydrin carbanion (4 → 5), a selective deprotonation with trioctyl methyl ammonium hydroxide leading to the removal of HCN from 8, and the unusual sequence 5 → 12 in which the ring C enol ether of 5 is converted selectively into ring C diosphenol of 12. Key words: quassin, synthesis, selective base, diosphenols, acylation.


1985 ◽  
Vol 61 (3) ◽  
pp. 233-238 ◽  
Author(s):  
I. E. Bella

Thinned stands of young lodgepole pine (Pinus contorta Dougl. var. latifolia Engelm.) in west-central Alberta had a higher incidence of attack by common pest organisms than unthinned stands. Based on a sample of nearly 3000 potential crop trees (on 240 temporary plots) growing on 120 naturally regenerated cut blocks, the rate of attack in thinned vs. unthinned stands was 30% and 18% for western gall rust (Endo-cronartium harknessii (J.P. Moore) Y. Hiratsuka) and 25%. and 16% for leader damage due to terminal weevil (Pissodes terminalis Hopp.) and pitch twig moth (Petrova spp.) Damage from other agents, including that from small mammals, was low and little affected by thinning. Forest management implication of these results are discussed. Key words: western gall rust terminal weevil, pitch twig moth, snowshoe hares, red squirrels.


1995 ◽  
Vol 73 (1) ◽  
pp. 70-74 ◽  
Author(s):  
Halvor Solheim

Invasion of lodgepole pine sapwood by blue-stain fungi was followed for 7 weeks after infestation by the mountain pine beetle, Dendroctonus ponderosae. During this period all sapwood was heavily stained blue and blue-stain fungi were always isolated close to the front of visible occlusion. Ophiostoma clavigerum and Ophiostoma montium were commonly isolated, both of which are known to be carried in the mycangia of the mountain pine beetle. Ophiostoma montium was most frequently isolated, but when both fungi were present O. clavigerum was always at the leading edge of fungal penetration. On average O. montium trailed 7.3 mm behind O. clavigerum. Other microorganisms were seldom isolated. Key words: lodgepole pine, Dendroctonus ponderosae, fungal succession, blue-stain fungi.


1986 ◽  
Vol 62 (3) ◽  
pp. 147-151 ◽  
Author(s):  
Yasuomi Tanaka ◽  
L. M. Harper ◽  
N. J. Kleyn

Based on the speed and completeness of laboratory germination and nursery bed emergence, the present study showed that for both Engelmann spruce (Picea engelmannii [Parry] Engelmann) and lodgepole pine (Pinus contorta Dougl.): (1) longer stratification generally improved the rate, and in some cases completeness, of germination more so under a cool temperature (15 °C/5 °C) regime than under a warm, standard temperature (30 °C/20 °C) regime emphasizing its importance for early spring outdoor sowing under suboptimal germination temperatures, (2) for a given stratification period, surface-drying at the end of stratification was at least as effective as surface-drying prior to or during stratification, and (3) stratification periods of 6 weeks or longer were generally the most effective. A 6- to 8-week stratification with seeds surface-dried at the end of stratification is recommended for nursery sowing of both species. Key Words: stratification, pinus contorta, Picea engelmanni, laboratory germination, nursery bed emergence.


1962 ◽  
Vol 40 (4) ◽  
pp. 609-614 ◽  
Author(s):  
Robena C. Robinson

A complex of fungi was isolated from lodgepole pine (Pinus contorta Dougl. var. latifolia Engelm.) at various stages of mountain pine beetle (Dendroctonus monticolae Hopk.) attack. Ceratocystis montia Rumb., Leptographium sp., Pichia pini (Hoist) Phaff, Hansenula holstii Wickerham, Hansenula capsulata Wickerham, and some unnamed yeasts were isolated from beetles, fresh galleries, and blue-stained sapwood. Perithecia of C. montia, Ceratocystis minor (Hedgc.) Hunt, Ceratocystis minuta (Siem.) Hunt, Ceratocystis sp., and Europhium sp. were found on the bark and sapwood of dead, blue-stained trees. Beetles are conclusively shown to be vectors of blue stain fungi. The known ranges of C. montia and P. pini are extended by this study and a possible succession of organisms associated with the development of beetle infestation is discussed.


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