Coumarins from Cedrelopsis grevei (Ptaeroxylaceae) Dulcie A. Mulholland a, *, Maria Kotsos a , Hamdani A. Mahomed a , Neil A. Koorbanally a , Milijaona Randrianarivelojosia a,b , Linda Quarles van Ufford c , Albert J.J. van den Berg c a Natural Products Research Group, School of Pure and Applied Chemistry, University of Natal, Durban, 4041, South Africa b Laboratory of Pharmacology, EES Sciences, University of Antananarivo, BP 906, Antananarivo, 101, Madagascar c Department of Medicinal Chemistry, Faculty of Pharmacy, University of Utrecht, PO Box 80082, 3508 TB Utrecht, The Netherlands Received in revised form 26 August 2002 Abstract The stem bark of Cedrelopsis grevei Baill. has yielded the first reported examples of 5-prenylated coumarins, cedrecoumarin A and B as well as the known coumarins, cedrelopsin, scoparone, O-methylcedrelopsin and norbraylin, and the known chromones ptaeroglycol and ptaeroxylinol. # 2002 Elsevier Science Ltd. All rights reserved. Keywords: Cedrelopsis grevei; Ptaeroxylon obliquum; Ptaeroxylaceae; b-Amyrin; Scoparone; O-methylcedrelopsin; Norbraylin; Cedrecoumarin A; Cedrecoumarin B; Ptaeroglycol; Ptaeroxylinol; a and b estrogen receptor agonist; Superoxide anion scavenger 1. Introduction The monotypic genus Ptaeroxylon has given difficulty to botanists, who have placed this genus in the Sapin- daceae, Rutaceae and most popularly, in the Meliaceae. In their generic monograph on the Meliaceae, Styles and Penington (1975) state that the genus Cedrelopsis is closely related to Ptaeroxylon and very similar to it in morphology and in the structure of the secondary xylem. The pollen of Cedrelopsis and Ptaeroxylon have been found to be very similar, unlike that of any known Meliaceous pollen grain but similar to that of some Rutaceae. They concluded that Cedrelopsis and Ptaer- oxylon do not belong to the Meliaceae and that there is insufficient evidence to place them in either the Sapin- daceae or Rutaceae. Thus, these genera are now con- sidered to form a separate family, the Ptaeroxylaceae, which has been shown to be chemically distinct from both the Rutaceae and Meliaceae and to contain a range of chromones and some unusual coumarins (Dean et al., 1967a, b; Dean and Taylor, 1966; Eshiett and Taylor, 1968; Dean and Robinson, 1971). Cedrelopsis grevei Baill. is one of seven species of the genus Cedrelopsis which is confined to Madagascar. This species is commonly referred to as ‘‘Katrafay’’ by the local people, and it is believed to relieve muscular fatigue when the bark is soaked in bath water. Two specimens have been investigated, one specimen from the wetter north-western part of Madagascar which resulted in the isolation of the pentacyclic triterpe- noid, b-amyrin, as well as two novel limonoid- derived compounds, a pentanortriterpenoid, cedmili- nol 1, and a hexanortriterpenoid, cedmiline 2 (Mul- holland et al., 1999; Fig. 1). The isolation of these limonoid derivatives led to the investigation of the second specimen collected in the drier south of Madagascar. Compounds which have been isolated previously from Cedrelopsis grevei include the 6,7-oxygenated chromones ptaeroxylin (Eshiett and Taylor, 1968), alloptaeroxylin, alloptaeroxylin methyl ether, peuci- nin, heteropeucinin, greveiglycol and ptaeroglycol (Dean and Robinson, 1971) as well as the coumarin cedrelopsin (Eshiett and Taylor, 1968). Ptaeroxylin, alloptaeroxylin (Dean and Taylor, 1966) and ptaer- oglycol (Dean et al., 1967b) have also been isolated from the South African Ptaeroxylon obliquum (Ptaeroxylaceae). 0031-9422/02/$ - see front matter # 2002 Elsevier Science Ltd. All rights reserved. PII: S0031-9422(02)00440-5 Phytochemistry 61 (2002) 919–922 www.elsevier.com/locate/phytochem * Corresponding author. Tel.: +27-31-260-1108; fax: +27-31-260- 3091. E-mail address: mulholld@nu.ac.za (D.A. Mulholland).