Planta Med 2015; 81 - PM_133
DOI: 10.1055/s-0035-1565510

Chemical constituents from Xylocarpus rumphii (Meliaceae)

L Ezra 1, W Waratchareeyakul 1, 2, K Chantrapromma 3, S Chantrapromma 4, MK Langat 1, SL Schwikkard 1, DA Mulholland 1
  • 1Natural Products Research Group, Department of Chemistry, University of Surrey, Guildford, United Kingdom
  • 2Department of Chemistry, Rambhai Barni Rajabhat University, Chantaburi, Thailand
  • 3Institute of Research and Development, Walailak University, Nakhon Si Thammarat, Thailand
  • 44Department of Chemistry, Prince of Songkla University, Songkhla, Thailand

Eleven compounds were isolated from the heartwood of X. rumphii and were identified as xylorumphins A and C (1 and 2), xylorumphiin C (3), xylorumpholides A-G (4 – 10) and odoratone (11). Compounds 4 – 10 have a hemiacetal group which opens and closes in solution making it impossible to purify. Acetylation enabled separation of the α and β forms. Column chromatographic separation of the acetylated fraction of impure 4 – 10 led to the isolation of one acetylated derivative of 4 (4a), four acetylated derivatives of 5 (5a-d), two acetylated derivatives of 6 (6a and 6b), one acetylated derivative of 8 (8a), two acetylated derivatives of 9 (9a and 9b) and one acetylated derivative of 10 (10a). In addition, five compounds were isolated from the bark of the same plant and were identified as xylorumphin B (12), xyloccensin E (13), taraxer-14-en-3β-ol (14), 22ε-hydroxytirucalla-7,24-dien-3,23-dione (15) and 3-oxo-(20S,24S)-epoxydammaran-25-ol (16). Compounds 1, 2, 4 – 10 and 12 have not been described previously. Chemical constituents from the Xylocarpus genus are reported to exhibit several biological activities such as antidiarrhoeal [1], antimalarial [2], anti-inflammatory [3] and insect antifeedant [4], and the aqueous extract of X. granatum is reported to express significant antifilarial activity [5]. Eight compounds, 1 – 6, 4a and 13 were tested at one concentration, 1 × 10 – 5 M, against several leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast cancer cell lines. The compounds did not meet activity criteria in the one-dose NCI59 cell test for further testing.

References:

[1] Shen LR, Guo D, Yu YM et al. Chem Biodivers 2009; 6: 1293 – 1308

[2] MacKinnon S, Durst T, Arnason JT et al. J Nat Prod 1997; 60: 336 – 341

[3] Sarigaputi C, Sommit D, Teerawatananond T et al. J Nat Prod 2014; 77: 2037 – 2043

[4] Champagne DE, Koul O, Isman MB et al. Phytochemistry 1992; 31: 377 – 394

[5] Zaridah MZ, Idid SZ, Omar AW et al. J Ethnopharmacol 2001; 78: 79 – 84

Fig. 1: (PM-133)