Antifungal 3-Butylisocoumarins from Asteraceae-Anthemideae

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 1; pp. 19 - 25
• Main Authors: Engelmeier, D, Hadacek, F, Hofer, O, Lutz-Kutschera, G, Nagl, M, Wurz, G, Greger, H
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.01.2004; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Artemisia dracunculus; Ascomycota - drug effects; Ascomycota - pathogenicity; Asteraceae - chemistry; Austria; Biological and medical sciences; Chamaemelum mixtum; Chemical control; Chemistry, Medicinal; Control; Coumarins - chemistry; Coumarins - isolation & purification; Coumarins - pharmacology; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; Life Sciences & Biomedicine; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Phytopathology. Animal pests. Plant and forest protection; Plant Leaves - chemistry; Plant Roots - chemistry; Plant Sciences; Plants, Medicinal - chemistry; Pyricularia grisea; Science & Technology; Stereoisomerism; Structure-Activity Relationship; Austria; ACETYLENES; ARTEMIDIN; NATURAL ISOCOUMARINS; 6-METHOXYMELLEIN; RESISTANCE; POLYACETYLENVERBINDUNGEN; INDUCTION; DERIVATIVES; CONSTITUENTS; Plant pathogen; Tarragon; Compositae; Oxygen heterocycle; Pesticide crop; Fungi; Dicotyledones; Angiospermae; Bicyclic compound; Aromatic compound; Fungi Imperfecti; Thallophyta; Pyricularia grisea; Root; Artemisia dracunculus; Pesticides; Lactone; Biological activity; Fungicide; Side chain; Plant origin; Isolation; Flavoring crop; Spermatophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0301339

Seven new naturally occurring 3-butylisocoumarins were isolated and identified from lipophilic extracts of aerial as well as underground organs:  corfin (17) and 3‘-hydroxycorfin (18) from the roots of Chamaemelum mixtum and (−)-(R)-2‘-methoxydihydroartemidin (5), (+)-(S,R)-epoxyartemidin (6a), dracumerin (12), (+)-(R)-(E)-3‘-hydroxyartemidin (13), and capillarin isovalerate (20) from various organs of Artemisia dracunculus (tarragon). Furthermore, six known derivatives, artemidiol (7), (E/Z)-artemidin (11), capillarin (19), artemidinol (21), 8-hydroxyartemidin (22), and 8-hydroxycapillarin (23), were obtained. The antifungal activities of all naturally occurring derivatives were determined in a germ-tube inhibition test against a susceptible strain of rice blast fungus Pyricularia grisea. The 3-butyl side-chain is a prerequisite for high activity. Eleven structurally related synthetic derivatives were additionally tested to explore the influence of structural characteristics on activity. Benlate, blasticidin S, kresoxim-methyl, griseofulvin, and the carrot phytoalexin 6-methoxymellein all served as positive controls.