Three putrescine bisamides from the leaves of Aglaia grandis Akira Inada a, *, Kazuhiro Shono a , Hiroko Murata a , Yuka Inatomi a , Dedy Darnaedi b , Tsutomu Nakanishi a a Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan b Herbarium Bogoriense, Jalan Ir, H. Juanda, Bogor 16122, Indonesia Received 20 April 1999; received in revised form 2 September 1999 Abstract Three putrescine (i.e. 1,4-butanediamine) bisamides were isolated from the leaves of Aglaia grandis. Their structures were elucidated by interpretation of spectral data. 7 2000 Elsevier Science Ltd. All rights reserved. Keywords: Aglaia grandis; Meliaceae; Leaf; Putrescine bisamide 1. Introduction The genus Aglaia (Meliaceae) consists of about 130 species of dioecious trees and shrubs, mainly distribu- ted in tropical and subtropical regions of the world. Several bisamides containing either putrescine (1,4- butanediamine) or the corresponding pyrrolidine ring as a diamine part have been characterized from these plants (Babidge, Massy-Westropp, Pyne, Shiengthong, Ungphakorn & Veerachat, 1980; Brader, Vajrodaya, Greger, Bacher, Kalchhauser & Hofer, 1998; Duh et al., 1993; Joshi, Chowdhury, Vishnoi, Shoeb & Kapil, 1987; Nugroho et al., 1999; Saifah, Puripattanavong, Likhitwitayawuid, Cordell, Chai & Pezzuto, 1993; Sai- fah & Suparakchinda, 1998), some of these compounds were shown to exhibit antiviral (Joshi et al., 1987) and cytotoxic (Saifah et al., 1993) activity. In our study of the same genus, we have previously reported the iso- lation of three pregnane-type steroids and two cycloar- tane-type triterpene hydroperoxides from the leaves of A. grandis Korth (Inada, Murata, Inatomi, Nakanishi & Darnaedi, 1997). Here we report three new pu- trescine bisamides (1±3) and a known aromadendrane- type sesquiterpene (4) (Beechan, Djerassi & Eggert, 1978; Bohlmann, Grenz, Jakupovic, King & Robinson, 1983) from the same source. 2. Results and discussion After repeated column chromatography and HPLC separations of the EtOAc-soluble part of a MeOH extract of leaves of A. grandis, three putrescine bisa- mides, named grandiamides A (1), B (2), and C (3) were obtained, together with 4b,10a-dihydroxyaroma- dendrane (4). Identi®cation of 4 was achieved by com- parison with previously reported spectroscopic data (Beechan et al., 1978; Bohlmann et al., 1983). Grandia- mide A (1), a D  108:88 (CHCl 3 ) exhibited a quasi- molecular ion peak (M + H) + of C 38 H 45 N 2 O 9 by HR positive-FABMS and showed absorptions at 1750 (ester), 1665, 1620 (amide), and 1595 cm 1 (benzene ring) in the IR spectrum. The 1 H-NMR spectrum of 1 (Table 1) analyzed with the aid of 2D-NMR exper- iments (COSY, NOESY, and HETCOR ) indicated the presence of three methoxy methyls d 3.67, 3.75, and 3.81), an acetoxyl methyl d 2.26), a tigloyl group d 1.75 (3H) 1.79 (3H), and 6.35 (1H)], four methylenes [(d 1.35±1.5 (4H) and 3.0±3.2 (4H)], three methines d 3.69, 4.42, and 5.87), and aromatic protons. Beside these groups, the 13 C-NMR spectrum of 1 (Table 1) Phytochemistry 53 (2000) 1091±1095 0031-9422/00/$ - see front matter 7 2000 Elsevier Science Ltd. All rights reserved. PII: S0031-9422(99)00519-1 www.elsevier.com/locate/phytochem * Corresponding author.