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.

Selagine, an alkaloid of Lycopodiumselago, is shown to be identical with huperzine A (2). A minor alkaloid, C15H18N2O2, isolated from L. selago is found to be 6β-hydroxyhuperzine A (4). Keywords: huperzine A, selagine, Lycopodium alkaloids, Alzheimer's disease, acetylcholine esterase inhibitor.

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Selagine, previously assigned as (I), is found to be identical with huperzine A (II).

. 65,765 (1987).The metabolites formed in still cultures by Ceratocystis tnirzor, one of the fungal species associated with the blue stain disease of pine, have been isolated and identified as ceratenolone (5), 6,8-dihydroxy-3-methylisocoumarin (2), 8-hydroxy-6-methoxy -3-methylisocoumarin (8),3,4-dihydro-6,8-dihydroxy -3-methylisocoumarin (lo), 3,4-dihydro-3-methy I-3,6,8-trihydroxy-3-methylisocoumarin (12), 3,4-dihydro-3-methyl-3,4,6,8-tetrahydroxyisocoumarin (13), and succinic acid. Ceratenolone (5), a new type of natural product, forms an intensely blue chelate with ferric ions. This chelate may be responsible for the blue coloration of the wood of pine infected by Cerarocysris mitzor.