Abstract
Five new limonoids named thaigranatins A–E (1–5), containing a C1–O–C29 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 IC50 value of 15.98 ± 6.87 μM and a CC50 value greater than 100.0 μM; whereas 10b showed significant inhibitory activity against IAV with an IC50 value of 14.02 ± 3.54 μM and a CC50 value greater than 100.0 μM.
Highlights
Xylocarpus granatum, a true mangrove plant, belongs to the family Meliaceae, of which the main secondary metabolites are limonoids [1,2]
Krishnolide A, a khayanolide-type of limonoid isolated from the Indian mangrove, Xylocarpus moluccensis, showed moderate antiviral activity against human immunodeficiency virus 1 (HIV-1) with an IC50 value of 17.45 ± 1.65 μM and a CC50 value of
To search for new antiviral natural compounds from mangrove plants, seeds of the Thai X. granatum, collected in the mangrove swamp of Trang Province, were investigated to afford five new limonoids collected in the mangrove swamp of Trang Province, were investigated to afford five new limonoids containing a C1 –O–C29 moiety, named thaigranatins A–E (1–5), along with the known one, granatumin containing a C1‒O‒C29 moiety, named thaigranatins A‒E (1‒5), along with the known one, L (6) (Figure 1), which exhibited antiviral activity against HIV-1
Summary
Xylocarpus granatum, a true mangrove plant, belongs to the family Meliaceae, of which the main secondary metabolites are limonoids [1,2]. Krishnolide A, a khayanolide-type of limonoid isolated from the Indian mangrove, Xylocarpus moluccensis, showed moderate antiviral activity against human immunodeficiency virus 1 (HIV-1) with an IC50 value of 17.45 ± 1.65 μM and a CC50 value of. To search for new antiviral natural compounds from mangrove plants, seeds of the Thai X. granatum, collected in the mangrove swamp of Trang Province, were investigated to afford five new limonoids collected in the mangrove swamp of Trang Province, were investigated to afford five new limonoids containing a C1 –O–C29 moiety, named thaigranatins A–E (1–5), along with the known one, granatumin containing a C1‒O‒C29 moiety, named thaigranatins A‒E (1‒5), along with the known one,. To find promising antiviral drug leads, granatumin L (6) (Figure 1), which exhibited antiviral activity against HIV-1. We report the isolation and structural antiviral drug leads, structural modification was applied to granatumin L (6).
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