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Mar. Drugs 2018, 16(11), 434; https://doi.org/10.3390/md16110434

Limonoids Containing a C1O–C29 Moiety: Isolation, Structural Modification, and Antiviral Activity

1,†
,
1,†
,
2
,
1,* and 2,*
1
Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, China
2
School of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Guangzhou 510515, China
These authors contributed equally.
*
Authors to whom correspondence should be addressed.
Received: 3 October 2018 / Revised: 25 October 2018 / Accepted: 31 October 2018 / Published: 4 November 2018
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Abstract

Five new limonoids named thaigranatins A–E (15), containing a C1O–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. 710, 8a8i, 9a9b, and 10a10c, 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. View Full-Text
Keywords: limonoid; a C1O–C29 moiety; isolation; structural modification; anti-HIV; anti-IAV limonoid; a C1O–C29 moiety; isolation; structural modification; anti-HIV; anti-IAV
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ren, J.-L.; Zou, X.-P.; Li, W.-S.; Shen, L.; Wu, J. Limonoids Containing a C1O–C29 Moiety: Isolation, Structural Modification, and Antiviral Activity. Mar. Drugs 2018, 16, 434.

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