Isolation, Structural Elucidation, and Anti-inflammatory Properties of Triterpenoids from the Stem Bark of Khaya senegalensis

International Journal of Chemistry | Vol. 1, No. 11, November 2010 | pp. 169–176

DOI: 10.46882/2010/IJC/000021

Article Type: Original Research Paper

Title: Isolation, Structural Elucidation, and Anti-inflammatory Properties of Triterpenoids from the Stem Bark of Khaya senegalensis

Names of Authors: A. A. Yusuf¹, M. T. Garba², S. O. Amupitan¹*

Authors’ Affiliations:
¹Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria.
²Department of Pharmacology and Therapeutics, Ahmadu Bello University, Zaria, Nigeria.

Abstract: Khaya senegalensis is widely used in West African traditional medicine to manage deep inflammatory conditions, yet specific bioactive compounds responsible for this pathway require isolation. This study reports the extraction, isolation, and structural elucidation of anti-inflammatory triterpenoids from the stem bark of this plant. The dried, powdered bark was extracted using 70% methanol and sequentially fractionated with n-hexane, chloroform, and ethyl acetate. Chromatographic separation of the chloroform fraction over silica gel column chromatography yielded two pure crystalline compounds. Their molecular configurations were determined using mass spectrometry (MS), infrared (IR) spectroscopy, and one-dimensional and two-dimensional nuclear magnetic resonance (¹H-NMR, ¹³C-NMR, COSY, and HSQC) analysis. The isolated compounds were confirmed as methyl angolensate and 7-deacetylkhivorin. In vivo anti-inflammatory screening was conducted using the carrageenan-induced rat paw edema model, benchmarked against indomethacin (10 mg/kg). Oral administration of the isolated triterpenoids at 50 mg/kg significantly suppressed edema volume by 64.2% and 58.8% respectively, after 4 hours. The compounds reduced localized myeloperoxidase activities and lowered systemic tumor necrosis factor-alpha (TNF-alpha) expression, validating that these limonoid-type triterpenoids act as active anti-inflammatory drivers that substantiate the ethnopharmacological use of K. senegalensis.

Keywords: Khaya senegalensis; Limonoids; Triterpenoids; Structural elucidation; Nuclear magnetic resonance; Anti-inflammatory activity

Manuscript Timeline: Received: August 04, 2010; Revised: September 15, 2010; Accepted: October 08, 2010; Published: November 02, 2010.

Citation: Yusuf, A. A., Garba, M. T., & Amupitan, S. O. (2010). Isolation, Structural Elucidation, and Anti-inflammatory Properties of Triterpenoids from the Stem Bark of Khaya senegalensis. International Journal of Chemistry, 1(11), 169–176.

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