Compound (R)-5; Rf = 0.44 (20:80 ethyl acetate/hexane); off white semi-solid; [α]D25 = −25.33 (c = 0.03 g/100 mL); 1H NMR (400 MHz, MeOD) δ: 2.63 (1H, dd, J = 10.7, 13.3 Hz, H-9a), 2.70-2.72 (1H, m, H-3), 3.15 (1H, dd, J = 4.0, 13.5 Hz, Sunitinib nmr H-9b), 3.82 (3H, s, Ar–OCH3-7), 3.87 (3H, s, Ar–OCH3-5), 4.10 (1H, dd, J = 6.9, 11.2 Hz, H-2b), 4.27 (1H, dd, J = 3.9, 11.2 Hz, H-2a), 6.06 (1H,

s, H-6), 6.07 (1H, s, H-8), 6.80 (2H, d, J = 8.4 Hz, H-2′,6′), 7.07 (2H, d, J = 8.4 Hz, H-3′,5′); 13C NMR (100 MHz, MeOD) 32.1 (CH2, C-9), 48.5 (CH, C-3), 55.0 (OCH3, C-7), 55.9 (OCH3, C-5), 68.9 (CH2, C-2), 92.9 (CH, C-8), 93.2 (CH, C-6), 105.3 (C, C-4a), 115.5 (CH, C-3′,5′), 130.2 (C, C-1′), 130.3 (CH, C-2′,6′), 154.5 (C, C-4′), 162.6 (C, C-7), 165.0 (C, C-8a), 165.9 (C,

C-5), 191.7 (C, C-4); HRMS (EI) calcd for C18H19O5 315.1154, found 315.1226. Compound (S)-5; Rf = 0.44 (20:80 http://www.selleckchem.com/products/AZD2281(Olaparib).html ethyl acetate/hexane); off white semi-solid; [α]D25 = +25.66 (c = 0.03 g/100 mL); 1H NMR (400 MHz, MeOD) δ: 2.64 (1H, dd, J = 10.4, 13.5, H-9a), 2.69-2.70 (1H, m, H-3), 3.14 (1H, dd, J = 4.1, 13.4 Hz, H-9b), 3.82 (3H, s, Ar–OMe-7), 3.86 (3H, s, Ar–OMe-5), 4.11 (1H, dd, J = 4.2, 7.0 Hz, H-2b), 4.27 (1H, dd, J = 3.9, 11.2 Hz, H-2a), 6.06 (1H, s, H-6), 6.07 (1H, s, H-8), 6.80 (2H, d, J = 8.4 Hz, H-2′,6′), 7.07 (2H, d, J = 8.4 Hz, H-3′,5′); 13C NMR (100 MHz, MeOD) 32.1 (CH2, C-9), 48.5 (CH, C-3), 55.0 (OCH3, C-7), 55.9 (OCH3, C-5), 68.9 (CH2, C-2), 92.8 (CH, C-8), 93.2 (CH, C-6), 105.3 (C, C-4a), 115.5 (CH, C-3′,5′), 130.1 (C, C-1′), 130.2 (CH, C-2′,6′), 154.7 (C, C-4′), 162.6 (C, C-7), 165.0 (C, C-8a), 165.9 (C, C-5), 191.9 (C, C-4); HRMS (EI) calcd for C18H19O5 315.1154, found 315.1220. Compound (R)-5, (S)-5 and the racemate were assessed for their potential anti-inflammatory activity. Ethical approval (003/09/Animal)

from the University of KwaZulu-Natal Celastrol Animal Ethics subcommittee was obtained prior to the investigation of acute croton oil-induced auricular dermatitis in a mouse model. Guidelines by the University of KwaZulu-Natal Animal Ethics Subcommittee and Biomedical Resources Unit for the maintenance and treatment of laboratory animals were followed. Eight-week old male Balb/c mice of approximately 30 g each were used. Equal volumes of croton oil (25 μl) were mixed with acetone (25 μl) as vehicle and applied (50 μl total volume; 1 h) onto the inner surface of the right auricle of each mouse to induce oedema. 9 Acetone has not been documented to have an anti-inflammatory effect by itself. 10 Thereafter, (R)-5, (S)-5 or the racemate were dissolved in acetone and 0.1 mg applied for 3 or 6 h treatment onto the right auricle to assess the reduction in oedema. The non-steroidal anti-inflammatory drug diclofenac was included as a positive control. Mice were euthanized after treatment for 3 and 6 h.