A new depsidone is shown to be 4-O-demethylnotatic acid by thinlayer chromatographic comparison of its diazomethane O-methylation products with those of the known depsidone notatic acid. The new depsidone was found in 22 of 33 taxa that also produce a related pf-orcinol depsidone, hypoprotocetraric acid. Hypoprotocetraric acid-previously known in Ocellularia, Parmelia, and Ramalina--also occurs in Leptotrema, Phaeotrema, and Thelotrema. In addition, some specimens produced 4-O-methylhypoprotocetraric acid and notatic acid. The depsides that correspond to the four depsidones studied here are all known, and this complete depside-depsidone series can be viewed in terms of possible biosynthetic pathways. Several recently described species of Parmelia subgen. Xanthoparmelia contain hypoprotocetraric acid (Hale, 1971a,b; Kurokawa & Elix, 1971), a compound previously known only in Ramalina (W. L. Culberson, 1967) and Ocellularia (C. F. Culberson & Culberson, 1968). In six of the Parmelia species, an unidentified PDsubstance occurs with hypoprotocetraric acid. The possibility that this new substance might be the depsidone corresponding to the depside norobtusatic acid was suggested by a recent discovery (Kurokawa et al., 1971) of 4-O-methylhypoprotocetraric acid and a depsidone, notatic acid, that corresponds to the depside obtusatic acid. The latter pair of depsidones occur together in a new Australian species, P. notata Kur. Experiments described in the present report prove that the new depsidone accompanying hypoprotocetraric acid is 4-O-demethylnotatic acid. The new depsidone was identified microchemically in hypoprotocetraric acid-containing species of several genera. In Parmelia subgen. Xanthoparmelia, the occurrence of these depsidones and their 4-O-methyl derivatives provides a biogenetically interesting parallel to the depside chemistry of some species in subgen. Parmelia sect. Hypotrachyna. MATERIALS AND METHODS Species containing hypoprotocetraric acid were analyzed by thin-layer chromatography (TLC) according to a standardized method (C. F. Culberson, 1972). Except where otherwise indicated, materials were from DUKE and Us. Chemical Studies on P. weberi Hale and P. notata Kur.-A small sample (0.11 g) of P. weberi (Weber &r Charette 3663) from Mexico was extracted four times with benzene at room 1 This study was supported in part by grant CB-25346 from the National Science Foundation. 2 Department of Botany, Duke University, Durham, North Carolina 27706. 3 Department of Botany, Smithsonian Institution, Washington, D.C. 20560. This content downloaded from 207.46.13.172 on Fri, 07 Oct 2016 06:15:05 UTC All use subject to http://about.jstor.org/terms 78 THE BRYOLOGIST [Volume 76
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