Short communication COX-2 inhibitors from the leaves of Pellacalyx saccardianus Scortech (Rhizophoraceae) Salam Ahmed Abed a, b , Hasnah Mohd Sirat a, * a Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia b Department of Pharmacognosy, College of Pharmacy, Kerbala University, Kerbala, Iraq A R T I C L E I N F O Article history: Received 8 February 2015 Received in revised form 1 May 2015 Accepted 7 May 2015 Available online 27 May 2015 Keywords: Pellacalyx saccardianus Rhizophoraceae Diarylheptanoid alkaloid Phytochemicals Anti-inflammatory activity COX-2 A B S T R A C T Phytochemicals and anti-inflammatory activity were investigated in the leaves of Pellacalyx saccardianus from the Rhizophoraceae family. The powdered leaves were extracted using methanol in a soxhlet extractor. Purification of the methanol extract yielded two new compounds, (3S)(6R)-3-(4 0 - hydroxybenzyl)-6-(6 00 -hydroxyphenethyl)-2,2-dimethyl-piperidin-4-one and 1,2-O-(1-methylethyli- dene)fucoside, together with six known compounds, b-amyrin palmitate, squalene, 24-ethylcholesta- 5,22,25-trien-3b-ol, 5R-hydroxy-1,7-bis(5-hydroxyphenyl)heptan-3-one, 1,7-bis(4-hydroxyphenyl) hept-4-en-3-one and methyl-L-fucoside. An anti-inflammatory assay using COX-2 revealed that b-amyrin palmitate possessed the highest inhibitory effect (96.8%) at the lowest concentration (0.01 mM), which was higher than that of the positive controls, resveratrol (90.2%, 0.01 mM) and indomethacin (79.20%, 100 mM). This is the first report on the isolation of phytochemicals from the leaves of P. saccardianus and their anti-inflammatory activity. ã2015 Published by Elsevier B.V. on behalf of Phytochemical Society of Europe. 1. Introduction Rhizophoraceae species have been used as herbal remedies in folk medicine, prompting investigation into their biological activities and an increase in the number of published reports in this field in recent years. For example, the crude extract from the bark of Rhizophora mangle was shown to have significant gastro- protective activity (Berenguer et al., 2006), and the ethanol extract of the leaves of Ceriops decandra was reported to have anti- nociceptive activity (Shilpi et al., 2012). The Rhizophoraceae species Rhizophora mucronata and Ceriops tagal are used in herbal medicine to control diabetes, and in vitro screening of the 80% aqueous ethanolic extracts from the bark of these species revealed high activity against a-glucosidase, with IC 50 values of 0.08  1.82 and 0.85  1.46 mg/mL, respectively (Lawag et al., 2012). Pellacalyx saccardianus, locally known as Membuluh, belongs to the Rhizophoraceae family and is widely distributed in Malaysia. Women use the leaves for bathing after childbirth (Ong et al., 2012). To date, there have been no reports on the phytochemistry and bioactivity of P. saccardianus, but one publication on the screening of the stems revealed the presence of a tropane alkaloid (Rahmani et al., 1985). Based on the aforementioned reports and the growing demand for active pharmaceutical components obtained from natural sources due to the detrimental side effects of synthesized drugs (Williams et al., 1999), we chose to evaluate the phytochemical components of P. saccardianus and their biological activities. The present work describes the isolation of the leaf extract chemical components to establish phytochemical data and assesses the in vitro inhibitory activity of pure secondary metabolites on prostaglandin synthesis through the COX-2 enzyme. 2. Results and discussion 2.1. Structure analysis Leaves of P. saccardianus were extracted with methanol in a soxhlet apparatus to afford a MeOH extract (PM) (25%). Separation and isolation of the methanol extract yielded two new constit- uents, (3S)(6R)-3-(4 0 -hydroxybenzyl)-6-(6 00 -hydroxyphenethyl)- 2,2-dimethyl-piperidin-4-one (1) and 1,2-O-(1-methylethyli- dene)fucoside (2) (Fig. 1), together with six known compounds 3–8. By comparing the compounds’ physical properties and spectroscopic data (IR, EIMS, 1 H NMR, 13 C and 2D NMR) with literature data, compounds 3–8 were identified as squalene (3) (Alam et al., 2002), b-amyrin palmitate (4) (Chávez et al., 1996; * Corresponding author. Tel.: +6075534319. E-mail addresses: salhmed2@gmail.com (S.A. Abed), hasnah@kimia.fs.utm.my (H.M. Sirat). http://dx.doi.org/10.1016/j.phytol.2015.05.001 1874-3900/ ã 2015 Published by Elsevier B.V. on behalf of Phytochemical Society of Europe. Phytochemistry Letters 13 (2015) 20–29 Contents lists available at ScienceDirect Phytochemistry Letters journal homepa ge: www.elsev ier.com/locate/phytol