Isolation of Lyngbyatoxin and other Teleocidin species from, Streptomyces Blastmyceticum” culture

Teleocidines originally found in japanese soil bacteria e. g. “Streptomyces mediocidicus” or “Streptomyces blastmyceticum” have aroused interest due to their ability of promoting tumor growth[1]. The structural feature which combines all these Teleocidin type substances is a 9-membered lactam ring linked to an indole nucleus[2]. It was reported that also Lyngbyatoxin, a secondary metabolite of the Hawaiian blue-green algae “Lyngbya Majuscula”, shows this structural feature[3]. Lyngbyatoxin is well-known for causing seaweed dermatitis to swimmers in Hawaii or Okinawa. Due to the structural similarity Lyngbyatoxin apparently was also proved to be a Tumor-promoter[1],[4]. We hereby report that “Streptomyces Blastmyceticum” can be induced to produce a slightly different spectrum of metabolites, by an altered cultivation scheme. Bacteria growth was performed in a very peptone rich medium for 4-5 days. LC / MS analysis of the culture solution showed presence of Lyngbyatoxin and other Teleocidin species. After centrifugation of the biomass, the supernatant solution was extracted with Amberlite XAD 1180N for 1 day. The crude extract was further purified by open normal phase and HPLC reversed phase chromatography. The LC / MS diagram of the purified compound can be seen in the figure below. The exact mass of Lyngbyatoxin was detected with less than 1 ppm error. Other Teleocidin compounds such as Olivoretin and Teleocidin B have been isolated in a similar manner. For further experiments other cultivation conditions will be tested on different strains of “Streptomyces” and the occurrence of Teleocidin compounds will be investigated.

Fig. 1 Upper picture: Chromatogram of crude Amberlite extract, lower picture: Enrichment of purified compound Lyngbyatoxin

• References

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• 2 Sakai S, Aimi N, Yamaguchi K, Hitotsuyanagi Y, Watanabe C, Yokose K, Koyama Y, Shudo K, Itai A. Elucidation of the structure of olivoretin A and D (Teleocidin B). Chem Pharm Bull 1984; 32: 354-357
• 3 Cardellina JH, Marner F, Moore RE. Seaweed Dermatitis: Structure of Lyngbyatoxin A. Sci 1979; 204: 193-195
• 4 Fujiki H, Sugimura T, Moore RE. New Classes of Environmental Tumor Promoters: Indole Alkaloids and Polyacetates. Environ Health Perspect 1983; 50: 85-90.