The Antinociceptive and Anti-Inflammatory Activities of Caulerpin, a Bisindole Alkaloid Isolated from Seaweeds of the Genus Caulerpa

Abstract

The antinociceptive and anti-inflammatory activity of caulerpin was investigated. This bisindole alkaloid was isolated from the lipoid extract of Caulerpa racemosa and its structure was identified by spectroscopic methods, including IR and NMR techniques. The pharmacological assays used were the writhing and the hot plate tests, the formalin-induced pain, the capsaicin-induced ear edema and the carrageenan-induced peritonitis. Caulerpin was given orally at a concentration of 100 μmol/kg. In the abdominal constriction test caulerpin showed reduction in the acetic acid-induced nociception at 0.0945 μmol (0.0103–1.0984) and for dypirone it was 0.0426 μmol (0.0092–0.1972). In the hot plate test in vivo the inhibition of nociception by caulerpin (100 μmol/kg, p.o.) was also favorable. This result suggests that this compound exhibits a central activity, without changing the motor activity (seen in the rotarod test). Caulerpin (100 μmol/kg, p.o.) reduced the formalin effects in both phases by 35.4% and 45.6%, respectively. The possible anti-inflammatory activity observed in the second phase in the formalin test of caulerpin (100 μmol/kg, p.o.) was confirmed on the capsaicin-induced ear edema model, where an inhibition of 55.8% was presented. Indeed, it was also observed in the carrageenan-induced peritonitis that caulerpin (100 μmol/kg, p.o.) exhibited anti-inflammatory activity, reducing significantly the number of recruit cells by 48.3%. Pharmacological studies are continuing in order to characterize the mechanism(s) responsible for the antinociceptive and anti-inflammatory actions and also to identify other active principles present in Caulerpa racemosa.

Marine Natural Products from Seaweeds

“…16 Além disso, conforme resultados anteriormente comentados, novos extratos foram testados e a caulerpina foi o princípio ativo responsável pela atividade anti-inflamatória e antinociceptiva observada nos extratos de Caulerpa racemosa e C. mexicana. [17][18][19] A atividade antioxidante de frações de Halimeda incrassata também foi estabelecida em estudos feitos por pesquisadores brasileiros, porém não foram isolados os seus princípios ativos. 20 Outras algas verdes foram avaliadas quanto ao seu potencial antioxidante, como, por exemplo, os extratos metanólicos de Codium decorticatum, Enteromorpha intestinalis, Ulva fasciata e Chaetomorpha antennina.…”

Phenolic profiles, antioxidant capacity, and acetylcholinesterase inhibitory activity of eight South African seaweeds

“…Their phytochemical properties elevate their potential value for the pharmaceutical industry (Yan et al 1998;Ganesan et al 2011). Seaweed extracts have various pharmacological properties including antioxidant Kannan et al 2013a), antimicrobial (Stirk et al 2007), anticancer, antinociceptive (De Souza et al 2009), photoprotective (Guinea et al 2012), antiinflammatory (De Souza et al 2009), antiacetylcholinesterase (Stirk et al 2007; Kannan et al 2013b); antidiabetic (Kannan et al 2013a), and antiviral (Hudson et al 1999) activities.…”

Taxonomy of Marine Macroalgae Used as Sources of Bioactive Compounds

“…An example is caulerpenyne, a metabolite that showed cellgrowth inhibitory effects (Fischel et al 1995 ) , antiproliferative activity in tumor cell lines (Barbier et al 2001 ) , and has been suggested as a possible alternative source of antitumor drugs (Cavas et al 2006 ) . The metabolite caulerpin has also been reported to have many in vitro biological activities, such as antitumor, growth regulator, and plant root growth stimulant; recently, in vivo bioactivities such as anticonceptive (i.e., analgesic) and anti-infl ammatory have also been described (de Souza et al 2009 ) .…”