Terpenoids and sterols from Artocarpus heterophyllus Lam. and Achras zapota Linn

• Main Author: Jorvina, Karen H.
• Format: text
• Language: English
• Published: Animo Repository 2005
• Subjects: Terpenes; Sterols; Medicinal plants; Multipurpose trees; Tropical fruit; Chemistry
• Online Access: https://animorepository.dlsu.edu.ph/etd_masteral/3356; https://animorepository.dlsu.edu.ph/context/etd_masteral/article/10194/viewcontent/CDTG004011_P.pdf
• Institution: De La Salle University

Two Philippine medicinal plants, Artocarpus heterophyllus Lam. and Achras zapota Linn., were studied for their secondary metabolites and antimicrobial properties against seven microorganisms: Staphylococcus aureus and Bacillus subtilis (gram-positive bacteria), Escherichia coli and Pseudomonas aeruginosa (gram-negative bacteria), and Candida albicans, Trichophyton mentagrophytes, and Aspergillus niger (fungi). The freeze-dried unripe fruits of Artocarpus heterophyllus Lam. afforded cycloartenone (KJ1), a 1:0.3 mixture of cycloartenol (KJ2a) and butyrospermol (KJ2b) together with smaller impurities that were not identified, and a 1:0.4 ratio of diastereomeric mixture of 2,3-butanediol (KJ16a and KJ16b). The structure of KJ1 was elucidated by extensive 1D and 2D NMR spectroscopy and mass spectrometry, while the mixture KJ2a and KJ2b, and another mixture KJ16a and KJ16b were determined by comparison of their spectra with those reported in the literature. Antimicrobial tests by the agar cup method afforded the following results. KJ1 gave moderate activity against C. albicans, A. niger, and P. aeruginosa, low activity against E. coli and T. mentagrophytes, and inactive against S. aureus and B. subtilis. The mixture KJ2a and KJ2b, together with smaller impurities indicated low antifungal activity against the three fungi and was found inactive against the four bacteria tested. The diastereomeric mixture of 2,3-butanediol, KJ16a and KJ16b, exhibited same activity as the standard antibiotic against P. aeruginosa, moderate activity against C. albicans, low activity against S. aureus, T. mentagrophytes and A. niger, and inactive against the other microorganism tested. The freeze-dried unripe fruits of Achras zapota Linn. afforded a fatty acid ester of oleanolic acid (CH5), a mixture of spinasterol (CH13a) and 22,23- dihydrospinasterol (CH13b) in a 1:0.4 ratio, and another mixture of short chain fatty acid esters of -amyrin (CH12a) and -amyrin (CH12b) in a 2:1 ratio. The structures of CH5, the mixture of CH13a and CH13b, and another mixture of CH12a and CH12b were determined by comparison of their spectra with those reported in the literature. Antimicrobial tests gave the following results. CH5 was found to have low activity against A. niger, and inactive against the other microorganisms tested. The mixture of CH12a and CH12b showed moderate activity against C. albicans, low activity against A. niger and T. mentagrophytes, and inactive against all the other microorganisms tested.