Extraction, Hemisynthesis, and Synthesis of Canthin-6-one Analogues. Evaluation of Their Antifungal Activities

• Published in: Journal of natural products (Washington, D.C.) Vol. 68; no. 11; pp. 1581 - 1587
• Main Authors: Soriano-Agatón, Flor, Lagoutte, Delphine, Poupon, Erwan, Roblot, François, Fournet, Alain, Gantier, Jean-Charles, Hocquemiller, Reynald
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.2005; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: alkaloids; Alkaloids - chemistry; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; antifungal properties; Aspergillus fumigatus; Aspergillus fumigatus - drug effects; Biological and medical sciences; Candida albicans; Candida albicans - drug effects; canthin-6-one; Carbolines; chemical structure; Chemistry, Medicinal; Cryptococcus neoformans; Cryptococcus neoformans - drug effects; Drug Evaluation, Preclinical; General pharmacology; Indole Alkaloids; indoles; Indoles - chemical synthesis; Indoles - chemistry; Indoles - isolation & purification; Indoles - pharmacology; Life Sciences & Biomedicine; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Naphthyridines - chemical synthesis; Naphthyridines - chemistry; Naphthyridines - isolation & purification; Naphthyridines - pharmacology; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; plant biochemistry; Plant Sciences; Plants, Medicinal - chemistry; Rutaceae; Saccharomyces cerevisiae; Saccharomyces cerevisiae - drug effects; Science & Technology; Structure-Activity Relationship; structure-activity relationships; Trichophyton - drug effects; Trychophyton mentagrophytes; Zanthoxylum; Zanthoxylum - chemistry; Zanthoxylum chiloperone var. angustifolium; Paraguay; South America; America; ROUTE; BETA-CARBOLINE ALKALOIDS; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; INDOLE; 1-METHOXYCANTHIN-6-ONE; CHILOPERONE VAR. ANGUSTIFOLIUM; (+)-VINCAMINE; CONSTITUENTS; SKELETON; Candida albicans; Cryptococcus neoformans; Bark; Lactam; Rutaceae; Extract; Stem; Medicinal plant; Fungi; Alkaloid; Antifungal agent; Dicotyledones; Angiospermae; Ascomycetes; Fungi Imperfecti; Chemical synthesis; Thallophyta; Hemisynthesis; Pharmacognosy; In vitro; Biological activity; Total synthesis; Plant origin; Spermatophyta; Aspergillus fumigatus; Saccharomyces cerevisiae
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050250z

Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1−3 from the canthin-6-one series were characterized. Derivatives 7−28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one did not show better antifungal activities.