Journal of Natural Medicines

, Volume 65, Issue 1, pp 206–211 | Cite as

A bioactive sesquiterpene from Bixa orellana

  • Dennis D. Raga
  • Rafael A. Espiritu
  • Chien-Chang Shen
  • Consolacion Y. RagasaEmail author


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.


Bixa orellana Bixaceae Ishwarane Phytol Polyprenol Prophylactic 


  1. 1.
    Quisumbing E (1978) Medicinal plants of the Philippines. Bureau of Printing, Manila, pp 623–624Google Scholar
  2. 2.
    Russell KR, Omoruyi FO, Pascoe KO, Morrison EY (2008) Hypoglycemic activity of Bixa orellana in the dog. Method Find Exp Clin Pharmacol 30(4):301–305CrossRefGoogle Scholar
  3. 3.
    Quanico JP, Amor EC, Perez GG (2008) Analgesic and hypoglycemic activities of Bixa orellana, Kyllinga monocephala and Luffa acutangula. Philipp J Sci 137:69–72Google Scholar
  4. 4.
    Fleisher TC, Ameade EPK, Mensah MLK, Sawer IK (2003) Antimicrobial activity of the leaves of Bixa orellana. Fitoterapia 74(1):136–138CrossRefGoogle Scholar
  5. 5.
    Pino JA, Correa MT (2003) Chemical composition of the essential oil from annatto (Bixa orellana L.) seeds. J Essent Oil Res 15(2):66–67Google Scholar
  6. 6.
    Grotto M, Sulman F (1967) Modified receptacle method for animal analgesimetry. Arch Int Pharmacodyn Ther 165:152–159PubMedGoogle Scholar
  7. 7.
    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 54:288–294PubMedCrossRefGoogle Scholar
  8. 8.
    Ragasa CY, Alimboyoguen AB, Urban S, Raga DD (2008) A bioactive diterpene from Smallanthus sonchifolius. Nat Prod Commun 3(10):1663–1666Google Scholar
  9. 9.
    Guevara BQ, Recio BV (1985) Phytochemical microbiological and pharmacological screening of medicinal plants. Acta Manilana Supplements. UST Research Center, ManilaGoogle Scholar
  10. 10.
    Ragasa CY, Javier ESC, Tan IG (2003) Antimutagenic triterpenes from Vitex parviflora. Philipp J Sci 132(1):21–25Google Scholar
  11. 11.
    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 16:34–39Google Scholar
  12. 12.
    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):5–12Google Scholar
  13. 13.
    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 76:105–107CrossRefGoogle Scholar
  14. 14.
    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 18:1–6CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer 2010

Authors and Affiliations

  • Dennis D. Raga
    • 1
  • Rafael A. Espiritu
    • 2
  • Chien-Chang Shen
    • 3
  • Consolacion Y. Ragasa
    • 2
    Email author
  1. 1.Biology Department and Center for Natural Sciences and Ecological ResearchDe La Salle UniversityManilaPhilippines
  2. 2.Chemistry Department and Center for Natural Sciences and Ecological ResearchDe La Salle UniversityManilaPhilippines
  3. 3.National Research Institute of Chinese MedicineTaipeiTaiwan

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