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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.

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A laboratory-centered approach to teaching introductory organic chemistry has been developed to accommodate large (250+ students) course sections. Through collaborative problem-solving, students are required to begin to develop the critical, creative, and complex thinking skills of chemical practitioners. These skills are emphasized in both classroom and lab components of courses. Course evaluations by students and teaching assistants attest to the success of this pedagogical approach. The teaching style required of teaching assistants is discussed and some of the pedagogical tools that have been developed are discussed.

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