Polyoxygenated Steroids from the Octocoral Leptogorgia punicea and in Vitro Evaluation of Their Cytotoxic Activity

Abstract

Five new polyoxygenated marine steroids—punicinols A–E (1–5)—were isolated from the gorgonian Leptogorgia punicea and characterized by spectroscopic methods (IR, MS, 1H, 13C and 2-D NMR). The five compounds induced in vitro cytotoxic effects against lung cancer A549 cells, while punicinols A and B were the most active, with IC50 values of 9.7 μM and 9.6 μM, respectively. The synergistic effects of these compounds with paclitaxel, as well as their effects on cell cycle distribution and their performance in the clonogenic assay, were also evaluated. Both compounds demonstrated significant synergistic effects with paclitaxel.

Marine Invertebrate Extracts Induce Colon Cancer Cell Death via ROS-Mediated DNA Oxidative Damage and Mitochondrial Impairment

“…Nevertheless, the semiquantitative analysis (as determined by the larger normalized area percentage) of the compounds present in the marine extracts utilized revealed that the observed antiproliferative effects might be associated with particular families of compounds (Tables 3-6). For instance, the main candidates to account for the antiproliferative effects of the CR extract might be diterpenes such as spongian-16-one [40], polyoxygenated marine steroids such as punicinol D [52], sesquiterpenes such as dendronephthol C [37], or sesterterpenes such as deoxoscalarin [38]. In the PS extract, furanocembranolide lopholide [56,64] seems to be the most abundant compound with a reported antiproliferative capacity in cancer cells.…”

Marine natural products

“…Relatively potent activity was observed towards phosphodiesterase-4, a target for CNS, inammatory and respiratory diseases. So corals also yielded a variety of steroids including pregnanes 1237 and 1238, 745 seco-sterols 1239-1244 746,747 and hydroxylated/polyhydroxylated sterols 1245-1265 [747][748][749][750][751][752][753] from species of Schleronephthya, Subergorgia, Sarcophyton, Sinularia, Verrucella, Echinogorgia, and Leptogorgia. Noteworthy amongst these compounds, was the enhanced (synergistic) cytotoxicity observed for paclitaxel in the presence of punicinols A 1257 and B 1258 (Leptogorgia punicea) and that the two sterols were also able to inhibit A549 tumour cell growth in a clonogenic assay over a sustained period of ten days.…”

A Review of Toxins from Cnidaria

“…The lowest IC 50 of 0.000005 µg/mL was observed for sesquiterpenes isolated from Isis hippuris (Anthozoa, Octocorallia) and active on human colon adenocarcinoma HT-29 and mouse lymphoma P388. Five new polyoxygenated marine steroids, named punicinols A, B, C, D and E, were isolated from the gorgonian Leptogorgia punicea (Anthozoa, Octocorallia) and showed in vitro cytotoxic activity (evaluated by using the sulforhodamine B assay) against human lung cancer A549 cells [ 205 ]. Punicinols A and B were the most active, with IC 50 values of 9.7 μM and 9.6 μM, respectively.…”