Anti-inflammatory effects of the gorgonian Pseudopterogorgia elisabethae collected at the Islands of Providencia and San Andrés (SW Caribbean)

Abstract

BackgroundWe are reporting for the first time the in vivo anti-inflammatory activity of extracts and fractions, and in vitro anti-inflammatory activity of pure compounds, all isolated from Pseudopterogorgia elisabethae collected at the Providencia (chemotype 1) and San Andrés (chemotype 2) Islands (SW Caribbean).MethodsExtracts from P. elisabethae were fractionated on silica gel to yield fractions: F-1 (pseudopterosins PsQ, PsS and PsU) and F-2 (amphilectosins A and B, PsG, PsK, PsP and PsT and seco-pseudopterosins seco-PsJ and seco-PsK) from chemotype 1, and F-3 (elisabethatrienol, 10-acetoxy-9-hydroxy- and 9-acetoxy-10-hydroxy-amphilecta-8,10,12,14-tetraenes (interconverting mixture) and amphilecta-8(13),11,14-triene-9,10-dione) from chemotype 2. By using preparative RP-HPLC and spectroscopic means, we obtained the pure PsG, PsK, PsP, PsQ, PsS, PsT, PsU, seco-PsK and the interconverting mixture of non-glycosylated diterpenes (IMNGD). The anti-inflammatory properties of extracts and fractions were evaluated using in vivo model "12-O-tetradecanoyl-phorbol-acetate (TPA)-induced mouse ear oedema". The activities of pure compounds and of the IMNGD were evaluated using in vitro assays myeloperoxidase (MPO) release (by human polymorphonuclear neutrophils (PMNs)), nitric oxide release (by J-774 cells) and scavenger activity on NO.ResultsIn the in vivo anti-inflammatory assay, extracts and F-3 showed low inhibition levels of inflammation compared to indomethacin, F-1 and F-2. Additionally, we evaluated the MPO release to the inflammation site, and found a marked inhibition of MPO levels by all extracts and fractions, even superior to the inhibition shown by indomethacin.Furthermore, in the MPO in vitro assay, IMNGD, PsQ, PsS, PsT and PsU, exhibited higher inhibition levels compared to dexamethasone and indomethacin. In the NO release in vitro, IMNGD, PsP and PsT were the most potent treatments. Finally, because the PsG, PsP and seco-PsK did not exhibit any NO scavenger activity, they should inhibit the inducible Nitric Oxide Synthase (iNOS) or other routes that influence this enzyme. Alternatively, PsQ, PsS, and PsU did show scavenger activity.ConclusionAll results presented contribute to demonstrate that the compounds isolated in this work from P. elisabethae are promising molecules with an interesting anti-inflammatory activity profile. Additionally, the results obtained could provide preliminary insights towards their structure-activity relationship.

Cytotoxic and Antimicrobial Activity of Pseudopterosins and seco-Pseudopterosins Isolated from the Octocoral Pseudopterogorgia elisabethae of San Andrés and Providencia Islands (Southwest Caribbean Sea)

“…However, only a limited number of these compounds has been evaluated for anti-inflammatory [21], anti-tuberculosis, anti-viral, anti-malarial and anti-cancer [11] activity.…”

“…Additionally, in in vitro experiments, PsQ, PsS, PsT, PsU and IMNGD showed good activity for the inhibition of MPO release; PsP, PsT and IMNGD inhibit NO release [21] and PsR inhibited thromboxane B2 (TXB 2 ) and the superoxide anion (O 2 − ) [11]. …”

Antiherpes screening of marine organisms from Colombian Caribbean Sea

“…E. fusca contains fuscosides A-D, glycosydicaly bound diterpenes with lobane and eudesmane related diterpene skeleton that presented interesting anti-inflammatory activity (Shin & Fenical, 1991;Jacobson & Jacobs, 1992). On the other hand, P elisabethae has been widely studied by the presence of diterpenes, mainly pseudopterosins and related compounds that present proved activity as anti-inflammatory compounds (Correa et al, 2009). In Colombia, two chemotypes with a different and characteristic contents of pseudopterosins and secopseudopterosins has been reported as part of our research as well as several new compounds have been isolated , Duque et al, 2006.…”

The Natural Products Chemistry of the Gorgonian Genus Pseudopterogorgia (Octocorallia: Gorgoniidae)

“…Critically, pseudopterosin P (16) exhibited the strongest inhibitory activity (76%) against Mycobacterium tuberculosis at 6.25 mg ml À1 , whereas pseudopterosin V (22) showed the most potent in vitro antimalarial activity, with an IC 50 of 1 mg ml À1 . 62 Pseudopterosins X and Y (28,29) showed antibacterial activity selectively against the Gram-positive bacteria Streptococcus pyogenes, Staphylococcus aureus, and Enterococcus faecalis with minimum inhibitory concentration (MIC) values ranging from 0.8 to 2.3 mg ml À1 . Considering the potential ability of some of these diterpene glycosides to inhibit inflammation, pseudopterosins Q (17), R (18), U (21), V (22), and 39-O-acetyl-pseudopterosin U (25) were also evaluated in a three-cell line panel consisting of MCF-7 (breast cancer), National Cancer Institute -NCI-H460 (nonsmall cell lung cancer), and SF-268 (central nervous system -CNS) cells.…”