Abstract
A dichloromethane extract of the air-dried leaves of Bixa orellana afforded ishwarane 1, phytol 2, polyprenol 3, and a mixture of stigmasterol 4a and sitosterol 4b by silica gel chromatography. The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy. Compound 1 at three doses (25, 50, and 100 mg/kg BW) was tested for prophylactic, gastrointestinal motility, analgesic, hypoglycemic, and antimicrobial potentials. Results of the prophylactic assay demonstrated the anti-toxic property of 1 at 100 mg/kg BW. A 50 mg/kg BW dose of 1 resulted in a more propulsive movement of the gastrointestinal tract (88.38 ± 13.59%) compared to the negative control (78.47 ± 10.61%). Tail flick and acetic acid writhing tests indicated that 100 mg/kg BW 1 had minimal analgesic activity. Compound 1 demonstrated no hypoglycemic potential on the animals tested. Compound 1 exhibited moderate antifungal activity against C. albicans, low activity against T. mentagrophytes, and low antibacterial activity against E. coli, S. aureus, and P. aeruginosa. It was inactive against B. subtilis and A. niger.
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References
Quisumbing E (1978) Medicinal plants of the Philippines. Bureau of Printing, Manila, pp 623–624
Russell KR, Omoruyi FO, Pascoe KO, Morrison EY (2008) Hypoglycemic activity of Bixa orellana in the dog. Method Find Exp Clin Pharmacol 30(4):301–305
Quanico JP, Amor EC, Perez GG (2008) Analgesic and hypoglycemic activities of Bixa orellana, Kyllinga monocephala and Luffa acutangula. Philipp J Sci 137:69–72
Fleisher TC, Ameade EPK, Mensah MLK, Sawer IK (2003) Antimicrobial activity of the leaves of Bixa orellana. Fitoterapia 74(1):136–138
Pino JA, Correa MT (2003) Chemical composition of the essential oil from annatto (Bixa orellana L.) seeds. J Essent Oil Res 15(2):66–67
Grotto M, Sulman F (1967) Modified receptacle method for animal analgesimetry. Arch Int Pharmacodyn Ther 165:152–159
Hirate K, Uchida A, Ogawa Y, Arai T, Yoda K (2006) Zaltoprofen, a non-steroidal anti-inflammatory drug inhibits bradykinin-induced pain responses without blocking bradykinin receptors. Neurosci Res 54:288–294
Ragasa CY, Alimboyoguen AB, Urban S, Raga DD (2008) A bioactive diterpene from Smallanthus sonchifolius. Nat Prod Commun 3(10):1663–1666
Guevara BQ, Recio BV (1985) Phytochemical microbiological and pharmacological screening of medicinal plants. Acta Manilana Supplements. UST Research Center, Manila
Ragasa CY, Javier ESC, Tan IG (2003) Antimutagenic triterpenes from Vitex parviflora. Philipp J Sci 132(1):21–25
Rideout JA, Ragasa C, Ngo HT (2003) Unusual oxygenated cations in electrospray ionisation mass spectroscopy of polyprenols from Jatropa curcas L. ACGC Chem Res Commun 16:34–39
Cayme JM, Ragasa CY (2004) Structure elucidation of β-stigmasterol and β-sitosterol from Sesbania grandiflora [Linn.] Pers. and β-carotene from Heliotropium indicum Linn. by NMR spectroscopy. Kimika 20(1–2):5–12
Vilar R, Milo B, Tomi F, Casanova J, Ferro EA, Canigueral S (2001) Chemical composition of the essential oil from the leaves of Piper fulvescens, a plant traditionally used in Paraguay. J Ethnopharmacol 76:105–107
Lago JHG, de Oliveira A, Guimaraes EF, Kato MJ (2007) 3-Ishwarone and 3-ishwarol, rare sesquiterpenes in essential oil from leaves of Peperomia oreophila Hensch. J Braz Chem Soc 18:1–6
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Raga, D.D., Espiritu, R.A., Shen, CC. et al. A bioactive sesquiterpene from Bixa orellana . J Nat Med 65, 206–211 (2011). https://doi.org/10.1007/s11418-010-0459-9
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DOI: https://doi.org/10.1007/s11418-010-0459-9