Sesquiterpenes and alkaloids from Scorodocarpus borneensis Christophe Wiart a , Marie-The´re`se Martin b , Khalijah Awang c , Nathalie Hue b , Laurent Serani b , Olivier Lapre´vote b, *, Mary Paı¨s b , Mawardi Rhamani a a Department of Chemistry, Universiti Pertanian Malaysia, 43400 Serdang, Malaysia b Institut de Chimie des Substances Naturelles, C.N.R.S., 91198 Gif-sur-Yvette Cedex, France c Department of Chemistry, University of Malaya, 59100 Kuala Lumpur, Malaysia Received 4 December 2000; received in revised form 26 February 2001 Abstract A new sesquiterpene, scodopin, and a mixture of three tryptamine-type alkaloids, scorodocarpines A–C, were isolated from the fruits of Scorodocarpus borneensis, together with a known hemisynthetic sesquiterpene, cadalene-b-carboxylic acid, which was iso- lated from the bark. The structures of the new compounds were elucidated by interpretation of spectral data, especially tandem mass spectrometry for the alkaloid mixture. # 2001 Elsevier Science Ltd. All rights reserved. Keywords: Scorodocarpus borneensis; Olacaceae; Sesquiterpenes; Tryptamine-type alkaloids; Tandem mass spectrometry 1. Introduction From the fruits of Scorodocarpus borneensis (Baill.) Becc. (Olacaceae) collected in Malaysia, we have iso- lated a new sesquiterpene scodopin 1 and a mixture of three tryptamine-type alkaloids named scorodocarpines A–C (2–4). In addition, a sesquiterpene 5 of the cada- lene group was isolated from the bark. Compound 5 has been synthesized previously, but was not known as a natural product (Parasmeswara Reddy and Khrisna Rao, 1982). The structures of the new compounds were established especially by 2D NMR along with tandem mass spectrosmetry (LSIMS/MS) for compounds 2–4. 2. Results and discussion Scodopin (1) gave a MH + peak in the HRCIMS at m/z 233.1545 which matched the molecular formula C 15 H 20 O 2 ( 0.0004 u). The UV spectrum (l max 251 and 333 nm) together with the IR spectrum ( 1619 and 1603 cm 1 ) suggested a highly conjugated keto derivative. In the 13 C NMR spectrum, the carbonyl resonated at  174.7 and a peak at  163.5 could be assigned to a phenolic 0031-9422/01/$ - see front matter # 2001 Elsevier Science Ltd. All rights reserved. PII: S0031-9422(01)00103-0 Phytochemistry 58 (2001) 653–656 www.elsevier.com/locate/phytochem * Corresponding author. Tel.: +33-1-69823032; fax: +33-1-690 77247. E-mail address: laprevote@icsn.cnrs-gif.fr (O. Lapre´vote).