Antihypertensive tetranortriterpenes and other metabolites from Swietenia macrophylla King

• Main Author: Sy, Arlene A.
• Format: text
• Language: English
• Published: Animo Repository 2000
• Subjects: Terpenes; Medicinal plants; Mahogany; Metabolites; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/etd_masteral/2503; https://animorepository.dlsu.edu.ph/cgi/viewcontent.cgi?article=9341&context=etd_masteral
• Institution: De La Salle University

Isolation and structure elucidation of some secondary metabolites from the cotyledon and the seed coat of the seeds of Swietenia macrophylla King were undertaken. The chloroform-soluble extracts obtained from the crude methanolic extracts were fractionated by column chromatography and purified by re-chromatography and recrystallization. Four compounds were isolated pure from the shell and were identified as y-sitosterol (MSL1B5), a fatty acid (MSL1B13), swietenolide (MSL25) and swietenine (MSL62). Swietenine (MS1B32) was also obtained pure from the chloroform extract of the seeds along with 3,6-O,O-Diacetylswietenolide (MS1B37). The structure of these compounds were elucidated from their melting points, mass spectral data as well as from 1H NMR and 13C NMR data. The seed coat methanolic extracts (Batch 1) showed significant antihypertensive activity while the cotelydon extracts did not. Hexane, chloroform (CHCl3), ethyl acetate (EtOAc) extracts and the remaining aqueous alcoholic layer were obtained from the crude methanolic extracts of Batch 2 samples. Only the hexane and the EtOAc extracts of both seed coat and cotyledon showed antihypertensive activity and so with the aqueous alcoholic layer of the seed coat. Two pure isolates from the seed coat, swietenolide and swietenine, showed significant antihypertensive activity at different doses. MSL25 was also found to be nontoxic at doses tested.