Phytochemical constituents of Sarracenia purpurea L. (pitcher plant) Asim Muhammad a , Pierre S. Haddad b , Tony Durst a , John Thor Arnason a,⇑ a Department of Biology, 20 Marie-Curie, Ottawa, ON K1N 6N5, Canada b Department of Pharmacology, Université de Montréal, Montréal, QC H3T1J4, Canada article info Article history: Received 11 August 2012 Received in revised form 10 May 2013 Available online xxxx Keywords: Pitcher plant Sarracenia purpurea Sarraceniaceae Chemical components 1 and 2D NMR spectroscopy abstract From the leaves of Sarracenia purpurea, collected in Mistissini, Quebec, Canada, four goodyerosides and three phenolics and nine known compounds, were isolated. The structures of the compounds were deter- mined by mass spectrometry, including HRMS, and by 1D and 2D NMR spectroscopy. Ó 2013 Elsevier Ltd. All rights reserved. 1. Introduction Sarracenia purpurea L., commonly known as the purple pitcher plant is a carnivorous plant in the family Sarraceniaceae. Its range includes almost the entire eastern seaboard of the United States, the Great Lakes, and south eastern Canada, making it the most common and broadly distributed pitcher plant, as well as the only member of the genus that inhabits cold temperature climates. The species is the floral emblem of the Canadian province of New- foundland and Labrador. By consuming nitrogen from insects trapped within their pitchers (fused leaves), they adapt to nitro- gen-poor environments, such as bogs and peat lands. This unusual natural history has received considerable attention from an ecolog- ical perspective. The pitcher plant has a long history of use as a tra- ditional medicine among indigenous peoples across the continent (Moerman, 1998; Grieve, 1931), and has been used for a wide vari- ety of conditions including gynecological aid, liver and kidney complaints, and is even reported as a treatment of smallpox during the 19th century. The leaves of this plant have been reportedly used in the treatment of dyspepsia, and constipation (Usher, 1974). Leaves of S. purpurea are used medicinally by the Cree First Nation of Eeyou Istchee, James Bay region, Quebec, Canada. Tradi- tionally, they are used in this area to treat symptoms associated with diabetes mellitus and other diseases (Leduc et al., 2006; Spoor et al., 2006). 2. Results and discussion The ethanol extract of S. purpurea was subjected to chromato- graphic purification using Sephadex LH-20 and repeated RP-C18 column chromatography, followed by preparative-HPLC purifica- tion, respectively, to afford seven new compounds 1–7 (Fig. 1). In addition, nine known compounds were obtained and identified as goodyeroside (Zhang et al., 2009), quercetin-3-O-galactoside (Foo et al., 2000), quercetin-3-O-arabinoside (Jarman and Crowden, 1977), taxifolin-7-O-galactoside (Joyeux et al., 1995), gossypetin-3- O-galactoside (Fawzy et al., 2008), taxifolin (Kanji et al., 1995), tamarixetin-3-O-galactoside (Luecha et al., 2009), betulinic acid (Barthelemy et al., 2009), and ursolic acid (Rosa et al., 2008), respectively, on the basis of their physical and spectroscopic data and by comparison with literature data. The sugars were identified as D-glucose and D-galactose by GC analysis, in which the retention times of derivatives of the sugar residues and standard sugars were compared, as described in Section 4. Compound 1 was obtained as a light brown solid with melting point 220–222 °C, and [a] D +62.5. Its molecular formula was as- signed as C 20 H 24 O 11 by HRESIMS, which showed an m/z 440.1318 (calcd as 440.1320). The major bands in the IR spectrum exhibited absorptions at 3450 (hydroxyl groups), 1770 (five membered lac- tone), and 1640 (an a,b-unsaturated ester) cm À1 . The 1 H and 13 C NMR spectra of 1 showed signals and coupling patterns similar to those of goodyeroside-A, except for the feruloyl moiety (Xiao- Ming et al., 2000). The 13 C NMR spectrum indicated 20 signals (Ta- ble 1), by using DEPT experiment which showed the presence of one methyl, three methylene, 11 methine, and five quaternary carbons. The 13 C NMR spectrum exhibited signals (Table 1) for a 0031-9422/$ - see front matter Ó 2013 Elsevier Ltd. All rights reserved. http://dx.doi.org/10.1016/j.phytochem.2013.05.015 ⇑ Corresponding author. Tel.: +1 613 562 5262; fax: +1 613 562 5765. E-mail address: John.Arnason@uottawa.ca (J.T. Arnason). Phytochemistry xxx (2013) xxx–xxx Contents lists available at SciVerse ScienceDirect Phytochemistry journal homepage: www.elsevier.com/locate/phytochem Please cite this article in press as: Muhammad, A., et al. Phytochemical constituents of Sarracenia purpurea L. (pitcher plant). Phytochemistry (2013), http:// dx.doi.org/10.1016/j.phytochem.2013.05.015