Cytotoxic and Antiviral Triterpenoids from the Mangrove Plant Sonneratia paracaseolaris

Abstract

A chemical investigation was conducted on the aerial parts of the mangrove plant Sonneratia paracaseolaris, yielding five new triterpenoid paracaseolins A–E (1–4, and 11) together with twelve known analogues (5–10, 12–17). Their structures were established by extensive spectroscopic methods and comparisons their spectroscopic data with those of the known related compounds. The cytotoxicities against P388, HeLa, A549, and K562 tumor cell lines and anti-H1N1 (Influenza A virus) activities for the isolates were evaluated. Compound 4 showed potent cytotoxicity against the A549 cell line with an IC50 value of 1.89 µM, and compound 1 exhibited significant anti-H1N1 virus activity with an IC50 value of 28.4 µg/mL. A preliminary structure activity relationship was discussed.

Marine natural products

“…Mangroves or their associates were the sources of benzaldehyde 1492 (Rhizophora mangle), 719 sesquiterpenes 1493, 1494 (Rhizophora annamalayana), 720 terpenoids 1495, 1496 (Rhizophora mucronata), 721 diterpenes 1497-1499 (Ceriops tagal), 722 1500 (Wedelia prostrata), 723 triterpenes paracaseolins A-E 1501-1505 (Sonneratia paracaseolaris), 724 1506, 1507 (Rhizophora mucronata), 725 limonoids granaxylocartin A 1508, 726 xylomexicanins I and J 1509, 1510, 727 sundarbanxylogranins A-E 1511-1515, 728 and thaixylogranins A-H 1516-1523 (all from seeds of Xylocarpus granatum) 729 and krishnolides A-D 1524-1527 (from seeds of X. moluccensis) 730 and krishnadimer A 1528, an unusual C 2 -symmetric limonoid dimer (also from seeds of X. moluccensis). 731 The structure of the latter is notable for being the rst example of a dimeric limonoid.…”

High-Resolution PTP1B Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of PTP1B Inhibitors from Miconia albicans

“…Contrary to the seven methyl singlets observed for 13 – 17 , the 1 H NMR spectrum of 18 showed six methyl singlets and a methyl doublet attributed to a methyl group at C-19 (δ 0.95, 3H, d, 6.1 Hz, CH 3 -29). Further analysis based on 1D and 2D NMR and comparison with literature data established that 18 was 3- O - trans - p -coumaroyl-2α-hydroxydulcioic acid [ 34 ] ( Figure 4 ).…”

Ten-Year Research Update Review: Antiviral Activities from Marine Organisms

“…Two dimeric ARs, named integracins A and B, have been shown to have HIV-1 integrase inhibitory activities, with IC 50 values of 3.2 and 6.1 μM, respectively [ 127 ]. Gong et al [ 129 ] tested antiviral activity of triterpenoids isolated from Sonneratia paracaseolaris, a mangrove typically from China [ 140 ]. The isolated compound Paracaseolin A (1b,3b-dihydroxy botulin) was tested against influenza A H1N1 virus and the inhibition of viral activity was evaluated by cytopathic effect of the virus on MDCK cells.…”