New zoanthoxanthins from the mediterranean zoanthidParazoanthus axinellae

Cariello, Lucio; Crescenzi, S.; Prota, Giuseppe; Zanetti, Laura

doi:10.1007/bf01938317

Cited by 35 publications

(25 citation statements)

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“…The secondary metabolome of P. axinellae was first studied in the 1970s with the isolation and structure elucidation of polyaromatic alkaloids named zoanthoxanthins and parazoanthoxanthins 20 21 22 . Recently, a second original family of alkaloids, named parazoanthines, was recovered from the same species 23 .…”

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confidence: 99%

Metabolomic profiling reveals deep chemical divergence between two morphotypes of the zoanthid Parazoanthus axinellae

Cachet

Genta‐Jouve

Ivanišević

et al. 2015

Sci Rep

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Metabolomics has recently proven its usefulness as complementary tool to traditional morphological and genetic analyses for the classification of marine invertebrates. Among the metabolite-rich cnidarian order Zoantharia, Parazoanthus is a polyphyletic genus whose systematics and phylogeny remain controversial. Within this genus, one of the most studied species, Parazoanthus axinellae is prominent in rocky shallow waters of the Mediterranean Sea and the NE Atlantic Ocean. Although different morphotypes can easily be distinguished, only one species is recognized to date. Here, a metabolomic profiling approach has been used to assess the chemical diversity of two main Mediterranean morphotypes, the “slender” and “stocky” forms of P. axinellae. Targeted profiling of their major secondary metabolites revealed a significant chemical divergence between the morphotypes. While zoanthoxanthin alkaloids and ecdysteroids are abundant in both morphs, the “slender” morphotype is characterized by the presence of additional and bioactive 3,5-disubstituted hydantoin derivatives named parazoanthines. The absence of these specific compounds in the “stocky” morphotype was confirmed by spatial and temporal monitoring over an annual cycle. Moreover, specimens of the “slender” morphotype are also the only ones found as epibionts of several sponge species, particularly Cymbaxinella damicornis thus suggesting a putative ecological link.

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confidence: 99%

Metabolomic profiling reveals deep chemical divergence between two morphotypes of the zoanthid Parazoanthus axinellae

Cachet

Genta‐Jouve

Ivanišević

et al. 2015

Sci Rep

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“…Paragracine is isolated from the coelenterate species Parazoanthus gracilis (4). This compound and other related pigments isolated from the Mediterranean species P. axinellae and Epizoanthus arenaceus are classified as zoanthoxanthins (5,6). The basic structure of paragracine, 6-methyl-1,3,7,9-tetraazacyclopent[e]azulene, contains a 7-carbon troponoid ring with two guanidine groups attached to it, carrying two positive charges at pH 7 (see formula below).…”

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Current-dependent block of nerve membrane sodium channels by paragracine

Seyama¹,

Wu²,

Narahashi³

1980

Biophysical Journal

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Paragracine, isolated from the coelenterate species Parazoanthus gracilis, selectively blocks sodium channels of squid axon membranes in a frequency-dependent manner. The blocking action depends on the direction and magnitude of the sodium current rather than on the absolute value of the membrane potential. Paragracine blocks the channels only from the axoplasmic side and does so only when the current is in the outward direction. This block may be reversed by generating inward sodium currents. In axons in which sodium inactivation has been removed by pronase, the frequency-dependent block persists, and a slow time-dependent block is observed. A slow interaction with its binding site in the channel may account for the frequency-dependent block.

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“…Column chromatography (Cariello et al 1974a) was performed using silica-gel (60-120 mesh) and TLC on silica gel G. IR spectra were recorded with KBr pellets on a Perkin-Elmer 1710 FJ-IR spectrophotometer. 1 H NMR spectra were obtained on an Avance Brucker's Instrument DRX 300 with tandem mass spectrometry as an internal standard, while EI-MS was recorded at 70 eV on a Jeol-JMSD-300 mass spectrometer.…”

Section: Extraction and Fractionationmentioning

confidence: 99%

“…The specimens collected were green Zoanthus which measured about 3.8 cm in length. Several workers (Psuda et al 1960;Kittredge and Hughes 1964;Kokke et al 1979;Cariello et al 1974aCariello et al , 1974bCariello et al , 1974cRao et al 1984Rao et al , 1985Rao et al , 1989 have isolated nitrogenous compounds and sterols from Zoanthus. Rao and coworkers isolated an anti-inflammatory and analgesic amine from Zoanthus species; however, antifilarial activity of this marine organism has never been reported.…”

Section: Introductionmentioning

confidence: 99%

Antifilarial activity of Zoanthus species (Phylum Coelenterata, Class Anthzoa) against human lymphatic filaria, Brugia malayi

et al. 2004

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The chloroform methanol (1:1) extract of an unidentified green zoanthus (Phylum Coelenterata, Class Anthozoa) showed promising in vitro adulticidal activity with a lethal concentration of 125 microg/ml on Brugia malayi. This extract brought about a 52.2% reduction in circulating microfilariae of B. malayi when administered to infected Mastomys coucha at 250 mg/kg, orally for 5 consecutive days. Further fractionation of the extract led to the recovery of four fractions, which were evaluated simultaneously in both in vitro and in vivo systems against B. malayi. The chloroform fraction at 250 mg/kg orally for 5 days exhibited the highest macrofilaricidal action (42.5%), closely followed by the insoluble n-butanol fraction (34.3%), the soluble hexane fraction (32.4%), and the soluble n-butanol fraction (20.4%). In addition, the hexane soluble fraction caused 44.3% sterilization of the surviving female parasites. Two compounds isolated were found devoid of antifilarial activity.

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New zoanthoxanthins from the mediterranean zoanthidParazoanthus axinellae

Cited by 35 publications

References 1 publication

Metabolomic profiling reveals deep chemical divergence between two morphotypes of the zoanthid Parazoanthus axinellae

Metabolomic profiling reveals deep chemical divergence between two morphotypes of the zoanthid Parazoanthus axinellae

Current-dependent block of nerve membrane sodium channels by paragracine

Antifilarial activity of Zoanthus species (Phylum Coelenterata, Class Anthzoa) against human lymphatic filaria, Brugia malayi

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