Chemistry of Marine Natural Substances: Originality, Diversity, Distribution

Kornprobst, Jean‐Michel

doi:10.1002/9783527335855.marprod003

Cited by 8 publications

(23 citation statements)

References 80 publications

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“…Therefore, compounds 3 and 4 share the same relative configuration, except for carbon C-3. This observation is consistent with the hypothetic pathway from concinndiol to compound 4 inspired by the biosynthetic formation of pannosanol [ 6 ] ( Figure 2 ).…”

Section: Resultssupporting

confidence: 90%

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New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica

et al. 2018

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The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C15-acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,β-unsaturated aldehyde terminal unit. Compound 4 is the first diterpene exhibiting a 19(4→3)abeo-labdane skeleton isolated from a Laurencia species. Isolation of concinndiol (compound 3) together with compound 4 suggests a common biosynthetic origin. Additionally, five known compounds, namely sagonenyne, laurene, α-bromocuparene, microcladallene A, and β-snyderol were identified in chromatographic fractions by NMR analysis using a computerized method that was developed in our laboratory.

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Section: Resultssupporting

confidence: 90%

“…Diterpenes isolated from the Laurencia species or mollusks feeding on them (especially from the genus Aplysia ) are divided into approximately twenty skeletons and one hundred compounds. Labdane-related compounds isolated from the Laurencia species are mostly brominated and represent more than half of the diterpenes [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica

et al. 2018

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“…The identification of these pigments was based on the comparison of their elemental compositions based on exact mass measurements with data from the literature [4,8,20,50,51]. As identification was based on exact mass measurements; we could not determine which isomer corresponds to the Spinochrome D or A.…”

Section: Resultsmentioning

confidence: 99%

The Roles of Spinochromes in Four Shallow Water Tropical Sea Urchins and Their Potential as Bioactive Pharmacological Agents

et al. 2017

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Spinochromes are principally known to be involved in sea urchin pigmentation as well as for their potentially interesting pharmacological properties. To assess their biological role in sea urchin physiology, experiments are undertaken on crude extracts from four species and on four isolated spinochromes in order to test their antibacterial, antioxidant, inflammatory and cytotoxic activities. First, the antibacterial assays show that the use of crude extracts as representatives of antibacterial effects of spinochromes are inaccurate. The assays on purified spinochromes showed a decrease in the growth of four strains with an intensity depending on the spinochromes/bacteria system, revealing the participation of spinochromes in the defense system against microorganisms. Secondly, in the 2,2-diphenyl-1-picrylhydrazyl antioxidant assays, spinochromes show an enhanced activity compared to the positive control. This latter observation suggests their involvement in ultraviolet radiation protection. Third, spinochromes present a pro-inflammatory effect on lipopolysaccharide-stimulated macrophages, highlighting their possible implication in the sea urchin immune system. Finally, cytotoxicity assays based on Trypan blue exclusion, performed in view of their possible future applications as drugs, show a weak cytotoxicity of these compounds against human cells. In conclusion, all results confirm the implication of spinochromes in sea urchin defense mechanisms against their external environment and reveal their potential for pharmacological and agronomical industries.

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“…A growing number of marine organisms are being chemically investigated in the search for new biomolecules with pharmacological potential [6,7]. This is particularly the case of echinoderms in which each class seems to produce specific metabolites, uncommon in the animal kingdom [8]. Quinonic pigments are specific to Echinoidea (i.e., naphtoquinones; [9,10,11]) and Crinoidea (i.e., anthraquinones; [12]) but are not present in Holothuroidea and Asteroidea, which both produce their specific types of triterpenoid glycosides (i.e., saponins) [13,14].…”

Section: Introductionmentioning

confidence: 99%

Triterpenoids in Echinoderms: Fundamental Differences in Diversity and Biosynthetic Pathways

et al. 2019

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Echinoderms form a remarkable phylum of marine invertebrates that present specific chemical signatures unique in the animal kingdom. It is particularly the case for essential triterpenoids that evolved separately in each of the five echinoderm classes. Indeed, while most animals have Δ5-sterols, sea cucumbers (Holothuroidea) and sea stars (Asteroidea) also possess Δ7 and Δ9(11)-sterols, a characteristic not shared with brittle stars (Ophiuroidea), sea urchins (Echinoidea), and crinoids (Crinoidea). These particular Δ7 and Δ9(11) sterols emerged as a self-protection against membranolytic saponins that only sea cucumbers and sea stars produce as a defense mechanism. The diversity of saponins is large; several hundred molecules have been described in the two classes of these saponins (i.e., triterpenoid or steroid saponins). This review aims to highlight the diversity of triterpenoids in echinoderms by focusing on sterols and triterpenoid glycosides, but more importantly to provide an updated view of the biosynthesis of these molecules in echinoderms.

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Chemistry of Marine Natural Substances: Originality, Diversity, Distribution

Cited by 8 publications

References 80 publications

New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica

New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica

The Roles of Spinochromes in Four Shallow Water Tropical Sea Urchins and Their Potential as Bioactive Pharmacological Agents

Triterpenoids in Echinoderms: Fundamental Differences in Diversity and Biosynthetic Pathways

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