Typhaphthalide and typharin, two phenolic compounds from Typha capensis Francis O. Shode*, Abdul S. Mahomed, Colin B. Rogers Discipline of Chemistry, School of Physical Sciences, University of Durban-Westville, Private Bag X54001, Durban 4000, South Africa Received 8 May 2002; received in revised form 8 August 2002 Abstract Two new phenolics, named typhaphthalide (a benzylphthalide) and typharin (an isocoumarin) plus sitosterol were isolated and identified from the hexane extract of the rhizomes of Typha capensis. The acetone extract yielded afzelechin, epiafzelechin, and catechin. # 2002 Elsevier Science Ltd. All rights reserved. Keywords: Typha capensis; Typhaceae; Bulrush; Phthalide; Isocoumarin; Typhaphthalide; Typharin 1. Introduction Typha capensis (Rohrb.) N.E.Br, commonly referred to as bulrush, is a robust, reed-like plant sparsely dis- tributed in the North Western Cape region but very common in South Africa (Van Wyk et al., 1997). The rhizomes are used in traditional medicine during preg- nancy to ensure easy delivery, for venereal diseases, dysmenorrhea, diarrhoea, dysentery, and to enhance the male potency and libido, amongst others (Watt and Breyer-Brandwijk, 1962; Hutchings et al., 1996). The phytochemistry of several species of the genus Typha has been documented (Chapman and Hall, 2000). Sev- eral flavones and other phenolic compounds, long chain hydrocarbons as well as various triterpenoids with a steroidal skeleton have been isolated (Chapman and Hall, 1996). Examination of a sample of rhizomes of T. capensis collected in Pinetown near Durban, S.A. has yielded the novel compounds typhaphthalide (1), typharin (2), as well as sitosterol, afzelechin (3), epiafzelechin (4), (+)- catechin (5), and ()-epicatechin (6). The structures of compounds 1 and 2 were elucidated using spectroscopic techniques. 2. Results and discussion A n-hexane extract of rhizomes of T. capensis depos- ited crystals of compound 1 on standing for several days. This compound had the molecular formula C 15 H 12 O 3 as determined by high resolution mass spec- trometry and 13 C NMR analysis. The IR spectrum of 1 showed the presence of a chelated phenolic hydroxyl group (3544 cm 1 , 3437 cm 1 ), a carbonyl group (1714 cm 1 ), a methylene group (2922 cm 1 ), and aromatic ring (1624 cm 1 , 1607 cm 1 , 1471 cm 1 ). The NMR spectra (Table 1) of compound 1 showed the presence of one monosubstituted benzene ring ( H 7.30–7.19 m 5H;  C 129.7 d, 128.6 d, 127.3 d, 5C), a trisubstituted ben- zene ring [ H 6.87 d, 1H (J=8.2 Hz), 7.46 t 1H (J=7.9 Hz), 6.63 d 1H (J=7.4 Hz);  C 115.5 d, 136.6 d, 113.7 d, 3C], a benzylic methylene at  H 3.22 dd (J=6.7 Hz, 14 Hz);  C 40.7 t, and a broad singlet at  H 7.71 1H;  C 156.5 s 1C indicated the presence of a phenolic proton which attenuated in D 2 O. The benzylic methylene at  H 3.22 coupled with one methine [ H 5.68 t (J=6.5 Hz, 6.3 Hz);  C 82.6 d 1C] bearing an ether oxygen. The above spectral evidence and the molecular formula indicated the presence of a g- or -lactone in compound 1. The presence of a 7-hydroxyphthalide group in 1 was suspected and confirmed by comparison of its spectral data (IR and NMR) with known compounds such as 11 (Asakawa et al., 1982; Asakawa et al., 1987; Asakawa et al., 1986), which have similar skeletal structure. This compound 1, which was named 0031-9422/02/$ - see front matter # 2002 Elsevier Science Ltd. All rights reserved. PII: S0031-9422(02)00439-9 Phytochemistry 61 (2002) 955–957 www.elsevier.com/locate/phytochem * Corresponding author. Tel.: +27-31-2044992; fax: +27-31- 2044000. E-mail address: shode@pixie.udw.ac.za (F.O. Shode).