Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Artocarpus nobilis

• Published in: Phytochemistry (Oxford) 2004-05, Vol.65 (9), p.1287-1290
• Main Authors: Jayasinghe, Lalith, Balasooriya, B.A.I.S, Padmini, W.Chintha, Hara, Noriyuki, Fujimoto, Yoshinori
• Format: Article
• Language: English
• Subjects: 2,2'-diphenyl-1-picrylhydrazyl; Antifungal; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; antifungal properties; antioxidant activity; antioxidants; Artocarpus; Artocarpus - chemistry; Artocarpus nobilis; Biological and medical sciences; Biphenyl Compounds; Chalcone - analogs & derivatives; Chalcone - isolation & purification; Chalcone - pharmacology; Chalcones; Chemical control; chemical structure; Chromatography, Thin Layer - methods; Cladosporium - drug effects; Cladosporium cladosporioides; Control; DPPH; Free Radical Scavengers - chemistry; Free Radical Scavengers - isolation & purification; Free Radical Scavengers - pharmacology; Free Radicals - antagonists & inhibitors; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; fungicides; leaves; Molecular Structure; Moraceae; Nuclear Magnetic Resonance, Biomolecular; Phytopathology. Animal pests. Plant and forest protection; Picrates - antagonists & inhibitors; plant extracts; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Leaves - chemistry; Radical scavenging; radical scavenging activity; spectral analysis
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2004.03.033

Geranyl chalcone derivatives 1– 5 with antifungal activity against Cladosporium cladosporioides and radical scavenging activity towards the 2,2 ′-diphenyl-1-picrylhydrazyl (DPPH) were isolated from the leaves of Artocarpus nobilis. Antifungal activity guided fractionation of the n-butanol extract from the methanol extract of the leaves of Artocarpus nobilis furnished 2 ′,4 ′,4-trihydroxy-3 ′-geranylchalcone ( 1), 2 ′,4 ′,4-trihydroxy-3 ′-[6-hydroxy-3,7-dimethyl-2( E),7-octadienyl]chalcone ( 2), 2 ′,4 ′,4-trihydroxy-3 ′-[2-hydroxy-7-methyl-3-methylene-6-octaenyl]chalcone ( 3), 2 ′,3,4,4 ′-tetrahydroxy-3 ′-geranylchalcone ( 4), 2 ′,3,4,4 ′-tetrahydroxy-3 ′-[6-hydroxy-3,7-dimethyl-2( E),7-octadienyl]chalcone ( 5). The chalcones 3 and 5 are new natural products whereas 1 and 2 are reported first time from the family Moraceae. All these compounds showed good fungicidal activity against Cladosporium cladosporioides and high radical scavenging activity towards the 2,2 ′-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC bio-autography method.