Homarine, a Common Metabolite in Edible Mediterranean Molluscs: Occurrence, Spectral Data and Revision of a Related Structure

Polychronopoulos, Panagiotis; Magiatis, Prokopios; Skaltsounis, Alexios‐Léandros; Tillequin, François; Vardala-Theodorou, Evi; Tsarbopoulos, Anthony

doi:10.1080/10575630108041311

Cited by 22 publications

(10 citation statements)

References 15 publications

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“…[ 27 ], its detection being expected in A. maculata and A. tigrina . However, while uncommonly found in other members of the Heterobranchia [ 28 ], in agreement with our results, the same authors reported the detection of homarine in A. tricolorata [ 27 ]. Several roles have been described for the cyclic betaine derivative, considered to be a chemical defense tool in marine invertebrates, acting as both predator deterrent and antifouling agent [ 28 ].…”

Section: Discussionsupporting

confidence: 93%

Profiling of Heterobranchia Sea Slugs from Portuguese Coastal Waters as Producers of Anti-Cancer and Anti-Inflammatory Agents

et al. 2018

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Bioprospection of marine invertebrates has been predominantly biased by the biological richness of tropical regions, thus neglecting macro-organisms from temperate ecosystems. Species that were not the object of studies on their biochemical composition include the Heterobranchia gastropods Armina maculata, Armina tigrina and Aglaja tricolorata, inhabitants of the Portuguese Atlantic coastal waters. Here, we present for the first time the fatty acid profile of neutral lipids and homarine content of these three species. Qualitative and quantitative differences in the fatty acid content among species points to the existence of a fatty acid profile of neutral lipids, particularly of each genus. The results from cytotoxicity assays, using the acetonic extracts of the gastropods on human gastric adenocarcinoma (AGS) and human lung adenocarcinoma (A549) cell lines, revealed a pronounced cytotoxic effect of the A. tigrina extract on both cell lines (IC50 values of 68.75 and 69.77 μg mL−1 for AGS and A549, respectively). It is worth noting the significant reduction of NO levels in LPS-challenged RAW 264.7 macrophages exposed to A. tricolorata extract, at concentrations as low as 125 μg mL−1.

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Section: Discussionsupporting

confidence: 93%

Profiling of Heterobranchia Sea Slugs from Portuguese Coastal Waters as Producers of Anti-Cancer and Anti-Inflammatory Agents

et al. 2018

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“…The presence of TMAO in the plasma for the single Weddell seal that we analyzed indicates that the seal was most likely consuming fish. However, the presence of homarine also suggests a contribution of cephalopods given that homarine is found in squid and octopus [12,29] and Weddell seals have been shown to feed on cephalopods in McMurdo Sound, Antarctica [30]. Because AsB is ubiquitous in marine organisms, it is likely to be present in seal blood regardless of what type of prey a seal is eating.…”

Section: Discussionmentioning

confidence: 99%

“…It has also been found to be the dominant form of arsenic in tissues of marine mammals and seabirds [10,11]. Homarine is a polar nitrogen-containing compound found in numerous marine invertebrates such as mollusks [12] and marine shrimps [13,14]. DMSP, a sulfonium analog of betaine, is produced by marine phytoplankton and algae and is accumulated by filter feeders [15][16][17].…”

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confidence: 99%

Measurement of marine osmolytes in mammalian serum by liquid chromatography–tandem mass spectrometry

Lenky

McEntyre

Lever

2012

Analytical Biochemistry

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“…Polychronopoulos et al . 36 showed that homarine is a common and abundant metabolite in several marine molluscs 36 . In separations of mollusc extracts ( Ostrea edulis, Littorina littorea ) by SEC chromatography, homarine was shown to co-eluate with a major fraction of Zn 2+ 29,37 .…”

Section: Discussionmentioning

confidence: 99%

Distinct pathways for zinc metabolism in the terrestrial slug Arion vulgaris

Dvorak

Schnegg

Salvenmoser

et al. 2019

Sci Rep

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In most organisms, the concentration of free Zn2+ is controlled by metallothioneins (MTs). In contrast, no significant proportions of Zn2+ are bound to MTs in the slug, Arion vulgaris. Instead, this species possesses cytoplasmic low-molecular-weight Zn2+ (LMW Zn) binding compound that divert these metal ions into pathways uncoupled from MT metabolism. Zn2+ is accumulated in the midgut gland calcium cells of Arion vulgaris, where they associate with a low-molecular-weight ligand with an apparent molecular mass of ~ 2,000 Da. Mass spectrometry of the semi-purified LMW Zn binding compound combining an electrospray ion source with a differential mobility analyser coupled to a time-of-flight mass spectrometer revealed the presence of four Zn2+-containing ion signals, which arise from disintegration of one higher MW complex resulting in an ion-mobility diameter of 1.62 nm and a molecular mass of 837 Da. We expect that the novel Zn2+ ion storage pathway may be shared by many other gastropods, and particularly species that possess Cd-selective MT isoforms or variants with only very low affinity to Zn2+.

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Homarine, a Common Metabolite in Edible Mediterranean Molluscs: Occurrence, Spectral Data and Revision of a Related Structure

Cited by 22 publications

References 15 publications

Profiling of Heterobranchia Sea Slugs from Portuguese Coastal Waters as Producers of Anti-Cancer and Anti-Inflammatory Agents

Profiling of Heterobranchia Sea Slugs from Portuguese Coastal Waters as Producers of Anti-Cancer and Anti-Inflammatory Agents

Measurement of marine osmolytes in mammalian serum by liquid chromatography–tandem mass spectrometry

Distinct pathways for zinc metabolism in the terrestrial slug Arion vulgaris

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