Azadirone- and gedunin-type limonoids from Carapa procera seeds and their in vitro antimicrobial and antiproliferative activities.

Authors

Moussa Ndao, Samba Fama Ndoye, Ismaila Ciss, Seynabou Sokhna, Abda Ba, Evodie Numbi Wa Ilunga, Lalla Aicha Ba, Insa Seck, Karine Leblanc, Somia Rharrabti, Pascal Retailleau, Eric Huet, Matar Seck, Mehdi A Beniddir

Published in

Fitoterapia. Pages 107506. Oct 04, 2026. Epub Oct 04, 2026.

Abstract

The phytochemical study of the ethyl acetate extract of Carapa procera seeds led to the identification of two new limonoids, an azadirone-type limonoid, 6α,17β-dihydroxyazadiradione (1) and a gedunin-type limonoid, (-)-5-epi-5-hydroxy-7-deacetoxy-7-oxogedunin (2), as well as eleven known compounds, 6α-hydroxyazadiradione (3), 6-deoxydetigloylswietenin (4), mexicanolide (5), 7-deacetylgedunin (6), khayasin (7), 14,15-didehydroruageanin A (8), 17β-hydroxyazadiradione (9), xylomexicanolide A (10), swietmanin H (11), andirolide A (12), and krishnagranatin C (13). The structures were assigned based on comprehensive spectroscopic and X-ray crystallographic analyses in conjunction with TDDFT-ECD calculations. The relative configuration of the various stereocenters of selected molecules was established by ML-J-DP4. The antimicrobial and cytotoxic activities of the isolated compounds were evaluated against Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans, and Mycobacterium marinum, in addition to breast cancer cell lines, and normal cells. In vitro cytotoxic activity was obtained, ranging from 0.758 to 0.035 μM, with the best activity obtained for (-)-5-epi-5-hydroxy-7-deacetoxy-7-oxogedunin (2) on the MCF-7 cell line. With an IC₅₀ of 0.035 μM, this gedunin-type limonoid represents a promising candidate for further antiproliferative investigation. Moreover, 6-deoxydetigloylswietenin (4) exhibited moderate antimicrobial activity against M. marinum at a concentration of 100 μg/mL.

PMID:
42830116
Bibliographic data and abstract were imported from PubMed on 05 Oct 2026.

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