Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Artocarpus nobilis Lalith Jayasinghe a, * , B.A.I.S. Balasooriya a , W. Chintha Padmini a , Noriyuki Hara b , Yoshinori Fujimoto b a Institute of Fundamental Studies, Hantana Road, Kandy, Sri Lanka b Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan Received 14 November 2003; accepted 26 March 2004 Available online 7 May 2004 Abstract Antifungal activity guided fractionation of the n-butanol extract from the methanol extract of the leaves of Artocarpus nobilis furnished 2 0 ,4 0 ,4-trihydroxy-3 0 -geranylchalcone (1), 2 0 ,4 0 ,4-trihydroxy-3 0 -[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]chalcone (2), 2 0 , 4 0 ,4-trihydroxy-3 0 -[2-hydroxy-7-methyl-3-methylene-6-octaenyl]chalcone (3), 2 0 ,3,4,4 0 -tetrahydroxy-3 0 -geranylchalcone (4), 2 0 ,3,4,4 0 - tetrahydroxy-3 0 -[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 Cladospo- rium cladosporioides and high radical scavenging activity towards the 2,2 0 -diphenyl-1-picrylhydrazyl (DPPH) radical in TLC bio-autography method. Ó 2004 Elsevier Ltd. All rights reserved. Keywords: Artocarpus nobilis; Moraceae; Chalcones; Antifungal; Cladosporium cladosporioides; Radical scavenging; DPPH 1. Introduction In a continuation of our research work on search for bioactive compounds from Sri Lankan plants the present investigation was carried out on Artocarpus nobilis Thw. of the family Moraceae. A. nobilis is a tree of moderate size and the only endemic species of the genus Artocarpus found in Sri Lanka. Several phenolic compounds have been reported from the stem bark of the plant (Pav- anasasivam and Sultanbawa, 1973; Pavanasasivam et al., 1974; Kumar et al., 1977; Sultanbawa and Surendraku- mar, 1989). In this paper, we report the isolation and structure elucidation of five chalcone derivatives includ- ing two new with antifungal activity against Cladospo- rium cladosporioides and radical scavenging properties towards 2,2 0 -diphenyl-1-picrylhydrazyl (DPPH) radical from the leaves of A. nobilis. 2. Results and discussion The leaves of A. nobilis were defatted with n-hexane and extracted with methanol. The preliminary investi- gation of the methanol extract and the n-butanol extract from the methanol extract of the leaves of A. nobilis showed positive response in antifungal bioassay against Cladosporium cladosporioides by TLC bio-autography method (Homans and Fuchs, 1970). Antifungal activity guided fractionation of the n-butanol extract by a combination of chromatography over silica gel, RP-18 silica gel, sephadex LH-20 and reversed phase HPLC afforded compounds 1, 2, 3, 4 and 5 (Fig. 1). The absorption maxima observed at 208, 230, 373 nm in the UV spectra of compound 1–5 gave the first clue that all these compounds belongs to the same group of chalcones. Compound 1 was assigned the molecular formula C 25 H 28 O 4 [FABMS()): m/z 391[M–H]  . Detailed analysis of 1 H and 13 C NMR spectral data of 1 including DEPT, H–H COSY, HMQC and HMBC furnished evidence that the compound 1 to be 2 0 , 4,4 0 -tetrahydroxy-3 0 -geranylchalcone. Compound 2 was * Corresponding author. Tel.: +94-8232131; fax: +94-8232002. E-mail address: lalith@ifs.ac.lk (L. Jayasinghe). 0031-9422/$ - see front matter Ó 2004 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2004.03.033 Phytochemistry 65 (2004) 1287–1290 PHYTOCHEMISTRY www.elsevier.com/locate/phytochem