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Novel Natural Compounds and Their Anatomical Distribution in the Stinging Fireworm Hermodice carunculata (Annelida) - PubMed Skip to main page content
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. 2022 Sep 19;20(9):585.
doi: 10.3390/md20090585.

Novel Natural Compounds and Their Anatomical Distribution in the Stinging Fireworm Hermodice carunculata (Annelida)

Sara Righi  1 , Luca Forti  2 , Roberto Simonini  1 , Valentina Ferrari  1 , Daniela Prevedelli  1 , Adele Mucci  3
Affiliations

Novel Natural Compounds and Their Anatomical Distribution in the Stinging Fireworm Hermodice carunculata (Annelida)

Sara Righi et al. Mar Drugs. .

Abstract

Increasing evidence in the field of bioprospection fosters the necessity of studying poorly investigated poisonous marine invertebrates to expand knowledge on animal venom biology. Among marine annelids, amphinomid fireworms are notorious for their bearded trunk equipped with a powerful stinging capacity. Here, a methodological workflow based on analytical chemistry techniques (compound isolation followed by mass spectrometry and spectroscopy analyses) was applied to gain new insights, leading to the identification and structural elucidation of an array of natural products from Mediterranean specimens of Hermodice carunculata. Eight betaine-derived unprecedented compounds, named "carunculines", were detected, bearing two terminal ammonium groups tri-and disubstituted at the Cα (A, B) and a series of different alkyl chains (I-VIII). The mixture of chemicals was found in all the body parts of H. carunculata, supporting a mechanism of action triggered by their vehiculation inside the dorsal chaetae, and subsequent injection when chaetae break off on contact. Preliminary investigations to understand adaptive features were also performed, showing a trend in carunculine abundance that fits into the evolutionary history of these worms. These findings shed light on the chemical ecology of amphinomids, giving reasons for the success of H. carunculata in benthic environments and providing promising novel metabolites for biotechnological implications.

Keywords: amphinomid; aposematism; chemical defences; marine natural products; phylogeny.

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Conflict of interest statement

The authors declare that they have no conflicts of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
Molecular structures of complanines and hypotheses for carunculines. (a) Molecular structures of complanine and neocomplanines [20,21]. (b) Left panel: hypothesized molecular structures for carunculines (1–8) and their isomers derived by matching the structures obtained by NMR spectra and the formulae obtained by HPLC-ESI/HRMS data. R = alkyl chain I–VI; R1 = terminal ammonium portion (A) or (B); R2 = probably –(CH2)2–CHOH–R1. C2 are superimposed in the final structures. Right panel: terminal ammonium groups (A) and (B) and types of alkyl chains (I–VI) derived by NMR analysis.
Figure 2
Figure 2
1H spectrum in D2O of the fraction eluted by H2O + 0.4% AcOH of H. carunculata extract. Diagnostic signals of carunculines are marked with A and B. Cho = choline, EA = ethanolamine.
Figure 3
Figure 3
HPLC-ESI/HRMS chromatograms of carunculines (1–8) eluted by H2O + 0.4% AcOH. (a) Full MS chromatogram of the fraction with a magnified view of the target compounds (on the right). (b) Extracted ion chromatogram of carunculines (1–8) from H. carunculata: the peaks of compounds 1,3,5,8 (up) and 2,4,6,7 (down) and related isomers (i1,i2,i3,i4) are filled in blue, respectively.
Figure 4
Figure 4
Anatomical distribution and relative abundance of carunculines in H. carunculata derived by HPLC-ESI/HRMS chromatograms and peak area counts.
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