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Five new limonoids named thaigranatins A⁻E ( 1 ⁻ 5 ), containing a C₁⁻ O ⁻C 29 moiety, were isolated from seeds of the Thai Xylocarpus granatum , collected at the mangrove swamp of Trang Province, together with the known limonoid, granatumin L ( 6 ). The structures of these compounds were established by HR-ESIMS and extensive NMR spectroscopic data. The absolute configuration of 1 was unequivocally determined by single-crystal X-ray diffraction analysis, conducted with Cu Kα radiation; whereas that of 2 or 6 was established to be the same as that of 1 by the similarity of their electronic circular dichroism (ECD) spectra. In view of the marked antiviral activity of 6 , its structure was modified via hydrolysis with alkaline KOH, esterification with diazomethane and various organic acids, and oximization with hydroxyamine. Finally, 18 derivatives, viz.  7 ⁻ 10 , 8a ⁻ 8i , 9a ⁻ 9b , and 10a ⁻ 10c , were obtained. In vitro antiviral activities of these derivatives against human immunodeficiency virus 1 (HIV-1) and influenza A virus (IAV) were evaluated. Most notably, 8i exhibited marked inhibitory activity against HIV-1 with an IC 50 value of 15.98 ± 6.87 μM and a CC 50 value greater than 100.0 μM; whereas 10b showed significant inhibitory activity against IAV with an IC 50 value of 14.02 ± 3.54 μM and a CC 50 value greater than 100.0 μM.

Limonoids Containing a C1–O–C29 Moiety: Isolation, Structural Modification, and Antiviral Activity