Chromatographic analyses of the phloroglucinol derivatives of 86 collections comprising Dryopteris filix-mas (L.) Schott (4x), D. arguta (Kaulf.) Watt (2x), D. marginalis (L.) A. Gray (2x), and the hybrids D. filix-mas × marginalis (3x), D. cristata × marginalis (3x), D. goldiana × marginalis (2x), and D. intermedia × marginalis (2x) in North America is presented. Material of D. filix-mas from the West differed from that collected in the East. The western material was rich in filixic acid, and had a chromatographic spectrum similar to European D. filix-mas s. str. D. marginalis is lacking filixic acid, and is not closely related to D. filix-mas based on chromatographic evidence. Methylene-bisaspidinol, a compound not previously found in Dryopteris, was isolated from D. marginalis. D. arguta contains filixic acid, and has a chromatographic pattern close to that of D. abbreviata (DC.) Newman, which in turn is one of the ancestors of D. filix-mas s. str. in Europe. The influence of D. marginalis in the phloroglucinol spectrum of the interspecific hybrids studied was very strong except in the hybrid D. filix-mas × marginalis.
Phloroglucinol Derivatives of Hagenia abyssinica. II. The Structure Determination of Kosotoxin and Protokosin.