Oxidized Welwitindolinones from Terrestrial Fischerella spp

• Published in: Journal of natural products (Washington, D.C.) Vol. 62; no. 4; pp. 569 - 572
• Main Authors: Jimenez, Jorge I, Huber, Udo, Moore, Richard E, Patterson, Gregory M. L
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.1999; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Biological and medical sciences; chemical constituents of plants; chemical structure; Chemistry, Medicinal; Cyanobacteria; Fischerella; fischerella major; Fischerella muscicola; General pharmacology; indole alkaloids; Life Sciences & Biomedicine; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Science & Technology; spectral analysis; welwitindolinones; Micronesia; HAPALINDOLES; ALGA HAPALOSIPHON-FONTINALIS; ALKALOIDS; Terrestrial environment; Nitrogen heterocycle; Lactam; Tetracyclic compound; Ketone; Alkaloid; Microbial origin; Chlorine Organic compounds; Cyanobacteria; Organic isothiocyanate; Bacteria; Isolation; Aromatic compound; Isocyanide; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np980485t

3-Hydroxy-N-methylwelwitindolinone C isonitrile (3), 3-hydroxy-N-methylwelwitindolinone C isothiocyanate (4), and the novel cyclic ether N-methylwelwitindolinone D isonitrile (6) are three new alkaloids from two terrestrial Fischerella spp. belonging to the Stigonemataceae. Photooxidation of N-methylwelwitindolinone C isonitrile (1) leads to isonitriles 3 and 6. Isonitrile 3 is readily hydrated to 3-hydroxy-N-methylwelwitindolinone C formamide (5), an artifact produced during the isolation procedure.