Chemical Constituents of Murraya koenigii Berries
- PDF / 143,718 Bytes
- 2 Pages / 594 x 792 pts Page_size
- 34 Downloads / 320 Views
CHEMICAL CONSTITUENTS OF Murraya koenigii BERRIES
Siow-Ping Tan,1* Shi-Min Lim,1 Mei-Khee Wong,1 Cherng-Yiing Lim,1 and Mohd Azlan Nafiah2
Murraya koenigii (L.) Spreng. is a member of the Rutaceae family, which is commonly grown in home gardens in Malaysia. It is a highly valuable plant because of its characteristic aroma and medicinal value. It has been used as traditional medicine for the treatment of rheumatism, traumatic injury, and snake bite and has also been reported to have antioxidant, antidiabetic, and antidysenteric activities [1]. In continuation of our previous work [2–4], we present data on the isolation and identification of five carbazole alkaloids and a sesquiterpene from the hexane and dichloromethane crude extracts of the berries of M. koenigii collected from Sibu, Sarawak, Malaysia (TM1009). The berries of the plant (1.0 kg) were collected and extracted using methanol (1 L) via a maceration method to obtain 30.01 g methanol crude. The crude was then further partitioned using hexane, dichloromethane, and ethyl acetate to obtain the crude extract. The hexane crude berry extract (7.10 g) was chromatographed over a silica gel 60F254 (70–230 mesh) column eluted with hexane, hexane–dichloromethane, dichloromethane, and dichloromethane–methanol systems with increasing polarity to give 11 fractions (H1–H11). Fractions H1 and H2 were combined to give compounds 1 (13.1 mg) and 6 (7.8 mg); Frs. H7 and H8 were combined and extensively subjected to silica gel 60F254 (230–400 mesh) columns, leading to the isolation of compounds 2 (7.3 mg) and 4 (16.3 mg). Fractions H9 and H10 were combined and subjected to silica gel 60F254 (230–400 mesh) columns, leading to the isolation of compound 5 (9.2 mg). Meanwhile, the dichloromethane berry extract (2.68 g) of M. koenigii was chromatographed over a silica gel 60F254 (70–230 mesh) column eluted with an increasing-spolarity solvent system of hexane–dichloromethane–methanol to give 15 subfractions (D1–D15). The subfractions with similar TLC spot patterns were combined and extensively subjected to silica gel 60F254 (230–400 mesh) columns eluted with an increasing-polarity hexane–dichloromethane–methanol solvent system; Subfrs. D2–D4 were combined and led to the isolation of compound 2 (71.7 mg); Subfrs. D10 and D11 were combined to give compound 1 (15.5 mg), while Subfrs. D5–D8 were combined and subjected to preparative TLC eluted with the solvent system hexane–dichloromethane (2:8) to give compound 3 (5.3 mg). The structural elucidation of these compounds was done by 1D (1H, 13C, DEPT) and 2D (COSY, HMQC, HMBC) NMR, IR, UV, and MS (HR-ESI-MS) analysis. All the data were in good agreement with the literature data. Koenimbine (1), C19H19NO2, brown solid, mp 193–194°C. UV (CH3OH, λmax, nm): 238, 262, 295. IR (CH3OH, νmax, cm–1): 3334, 1637, 1025. HR-ESI-MS, m/z 294.2071 [M + H]+. PMR (500 MHz, CDCl3, δ, ppm, J/Hz): 7.75 (1H, br.s, NH), 7.64 (1H, s, H-4), 7.42 (1H, d, J = 2.3, H-5), 7.27 (1H, d, J = 8.6, H-8), 6.95 (1H, dd, J = 8.6, 2.3, H-7), 6.60 (1H, d, J = 9.8, H-9), 5
Data Loading...
