The chemistry of the blue stain fungi. Part 1. Some metabolites of Ceratocystis species associated with mountain pine beetle infected lodgepole pine

Abstract

Metabolites formed in still culture by Ceratocystisclavigera, C. ips, and C. huntii, three of the four Ceratocystis species associated with the blue stain disease of pine, have been identified. In addition to the ubiquitous fungal metabolites ergosterol, ergosterol peroxide, and fatty acids we have isolated succinic acid, β-phenethyl alcohol (1), tryptophol (2), prolylleucyl anhydride (3), tyrosol (4), 3-phenylpropane-1,2-diol (5), 6,8-dihydroxy-3-methylisocoumarin (8), 6,8-dihydroxy-3-hydroxymethylisocoumarin (9), p-hydroxybenzaldehyde (10), phenylacetic acid (11), p-hydroxyphenylacetic acid (12), phenyllactic acid (13), p-hydroxyphenyllactic acid (14), and 2,3-dihydroxybenzoic acid (15). The complex formed by chelation of iron with 2,3-dihydroxybenzoic acid may be responsible, at least in part, for the blue staining of the sapwood of diseased pine.

Tyrosol and tryptophol produced by Ceratocystis adiposa

“…High levels of environmental stress and intense and frequent interactions with other organisms promote the production of metabolically diverse compounds (Wagenaar et al 2002). Fungi of Ceratocystis genus are important pathogens of forest trees, causing problems such as blue stain of conifers, oak wilt and Dutch elm disease (Ayer et al 1986). In some reports, these microorganisms produce metabolites with biological activity in culture broth (Bycroft 1988;Pazzagli et al 1999).…”

The chemistry of the blue stain fungi. Part 3. Some metabolites of Ceratocystisminor (Hedgcock) Hunt

“…The blue stain disease of conifers is a serious disease of pine that currently causes the death of over 40 million pine trees per year in Western Canada (1)(2)(3). The disease is spread by the mountain pine beetle (Dendroctonus ponderosae Hopk.…”

“…The disease is spread by the mountain pine beetle (Dendroctonus ponderosae Hopk. ), which lives symbiotically with a variety of microorganisms (1). Four species of blue stain fungi have consistently been isolated from diseased wood, including Ceratocystis clavigera, C. huntii, C. ips, and C. minor.…”

“…2,3-Dihydroxybenzoic acid (I), which forms an intensely blue complex with ferric ions and which induces blue staining of lodgepole pine shavings and debarked sapwood (I); was isolated as one of the metabolites of C. huntii. It was postulated that the blue stain associated with the fungal infection might be due to metal complexes of compound 1 (1). Since 2,3-dihydroxybenzoic acid was not reported as a metabolite of C. minor (4,6), and since this fungus stains pine most rapidly, we decided to reexamine the metabolites produced by the fungus.…”

Diketopiperazines from the Marine Sponge Axinella sp.

“…[7], Calyx cf. podatypa [17], and sponge-associated microorganisms Alcaligenes faecalis A72 [18], the phytopathogenic fungus Rhizoctonia solani [19], marine bacteria Pecten maximus [8], Ceratocystis species [20], Aspergillus ochraceus and Oopsra destructor [21], sponge-associated bacterium Pseudomonas aeruginosa [22], Scenedesmus sp. [23], and roasted cocoa nibs [11].…”