A novel polyisoprenyl benzophenone derivative from Garcinia eugeniaefolia Sri Hartati a,b , Atiek Soemiati b , Hong-Bing Wang c , Leonardus B.S. Kardono a , Muhammad Hanafi a , Soleh Kosela b * and Guo-Wei Qin c * a Research Center for Chemistry, Indonesia Institute of Science, Komplek Puspiptek Serpong 15314, Indonesia; b Faculty of Sciences, University of Indonesia, Kampus Depok, Indonesia; c Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai 201203, China ( Received 2 February 2007; final version received 8 June 2007 ) A novel polyisoprenyl benzophenone derivative named eugeniaphenone (1) was isolated from the stem bark of Garcinia eugeniaefolia Wall. Its structure was elucidated by spectroscopic methods, including 1D and 2D NMR techniques, and confirmed by single-crystal X-ray diffraction analysis. It is the first example in which an isoprenyl unit formed a cyclobutane- containing side chain in the polyisoprenyl benzophenone derivatives. Keywords: Garcinia eugeniaefolia; Cluciaceae; eugeniaphenone; polyisoprenyl benzophenone 1. Introduction Garcinia species (Cluciaceae) are rich in various oxidized and isoprenylated xanthones and benzophenones, 1,2 of which some exhib- ited a wide range of biological and pharma- cological activities including antimalarial, 3 growth inhibition of human leukemia cells, cytopathic inhibition of in vitro HIV infection and cytotoxicities. 2,4,5 The polyisoprenyl benzophenones are mostly found in Garcinia and its related genera. They are unique in the structures and stereochemistry, possessing a common 2,4,9-triketo-bicycle[3,3,1]nonane moiety with various modified isoprenylated chains in different linkage forms. The biological significance and structural novel- ties of such compounds have attracted our great interests for further chemical study, which resulted in the isolation of lateriflor- one, a cytotoxic spiroxalactone with a novel skeleton from Garcinia lateriflora and gaudichaudiic acids F–I, the novel cytotoxic polyprenyl heptacyclic xanthonoids from Garcinia gaudichaudii. 5,6 In the course of our continuing study on genus Garcinia, we have investigated the species Garcinia eugeniaefolia Wall., a tropical plant distrib- uted in Indonesia (Kalimantan and Sumatra Islands), Philippines, Malaysia and India, and its chemical constituents have never been reported previously. In this paper, we describe the isolation and structural elucidation of eugeniaphenone (1), a minor component with novel polyisoprenyl benzophenone structure from the stem barks of the plant. 2. Results and discussion Eugeniaphenone (1) revealed a molecular formula C 38 H 50 O 6 by the EI-MS (m/z 602, [M] þ ) and 1 H and 13 C NMR spectral data ISSN 1028-6020 print/ISSN 1477-2213 online q 2008 Taylor & Francis DOI: 10.1080/10286020801966922 http://www.informaworld.com *Corresponding authors. Email: s2kimui@mail.cso.ui.ac.id; solehkosela@ui.edu; gwqin@mail.shcnc.ac.cn Journal of Asian Natural Products Research Vol. 10, No. 6, June 2008, 509–513