Eicosapentaenoic acid: Possible precursor of the phloroglucinol derivatives isolated from the brown alga Zonaria tournefortii (J.V. Lamouroux) Montagne

Hattab, Mohamed El; Bouzidi, Naïma; Ortalo-Magné, Annick; Daghbouche, Yasmina; Richou, Mireille; Chitour, Semch Eddine; Reviers, Bruno de; Piovetti, Louis

doi:10.1016/j.bse.2009.01.003

Cited by 16 publications

(13 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Alternatively, it can be explained by interfering reactions due to the use of a recombinant protein that was only partially purified in the previous study. A major product of the incubation of Esi-PKS1 with malonyl-CoA as an extender and lauroyl-CoA as a starter molecule was also tentatively identified by LC-ESI-MS as an acylphloroglucinol or a tetraketide that are reminiscent of the phenolic lipids (Gerwick and Fenical, 1982) that have been proposed to be derived from various long-chain fatty acids, precursor of phloroglucinol derivatives in the brown seaweed Zonaria tournefortii (El Hattab et al, 2009).…”

Section: Discussionmentioning

confidence: 99%

Structure/Function Analysis of a Type III Polyketide Synthase in the Brown Alga Ectocarpus siliculosus Reveals a Biochemical Pathway in Phlorotannin Monomer Biosynthesis

et al. 2013

View full text Add to dashboard Cite

ORCID ID: 0000-0001-7358-6282 (P.P.).Brown algal phlorotannins are structural analogs of condensed tannins in terrestrial plants and, like plant phenols, they have numerous biological functions. Despite their importance in brown algae, phlorotannin biosynthetic pathways have been poorly characterized at the molecular level. We found that a predicted type III polyketide synthase in the genome of the brown alga Ectocarpus siliculosus, PKS1, catalyzes a major step in the biosynthetic pathway of phlorotannins (i.e., the synthesis of phloroglucinol monomers from malonyl-CoA). The crystal structure of PKS1 at 2.85-Å resolution provided a good quality electron density map showing a modified Cys residue, likely connected to a long chain acyl group. An additional pocket not found in other known type III PKSs contains a reaction product that might correspond to a phloroglucinol precursor. In vivo, we also found a positive correlation between the phloroglucinol content and the PKS III gene expression level in cells of a strain of Ectocarpus adapted to freshwater during its reacclimation to seawater. The evolution of the type III PKS gene family in Stramenopiles suggests a lateral gene transfer event from an actinobacterium.

show abstract

Section: Discussionmentioning

confidence: 99%

Structure/Function Analysis of a Type III Polyketide Synthase in the Brown Alga Ectocarpus siliculosus Reveals a Biochemical Pathway in Phlorotannin Monomer Biosynthesis

et al. 2013

View full text Add to dashboard Cite

show abstract

“…The resulting acylphloroglucinol b-diketone would undergo intramolecular cyclization to afford the spiralisone derivative, then the chromone upon dehydration. While following the same reflection, El Hattab et al [56], supposed that Claisen condensation could be performed on a pentaketide precursor to form directly the acylphloroglucinol b-diketone.…”

Section: Biosynthesis and Total Synthesismentioning

confidence: 97%

“…After oxidation of the obtained secondary alcohol, and AR and ACP represent the largest family of natural lipophenols. In plant, their biosynthesis is believed to follow the polyketide pathway (Scheme 3): in a few words, a fatty acylCoA starter undergoes three condensation reactions with malonylCoA leading to a tetraketide intermediate [56,58], which can undergo two ring formation mechanisms: an aldol condensation (followed by an easy loss of carboxyl) would conduct to AR structures, while Claisen condensation allows to the formation of ACP. However, hypothesis of polyunsaturated long-chain AR biosynthesis has also been proposed for AR compound 33, in which the polyunsaturated part would be formed after cyclization and decarboxylation of a C18-polyketide [55,59] (Scheme 3).…”

Section: Biosynthesis and Total Synthesismentioning

confidence: 99%

Omega-3 polyunsaturated lipophenols, how and why?

et al. 2016

View full text Add to dashboard Cite

Polyphenols and n-3 polyunsaturated fatty acids (PUFAs) are two classes of natural compounds, which have been highlighted in epidemiological studies for their health benefits. The biological activities of those two families of metabolites on oxidation, inflammation, cancer, cardiovascular and degenerative diseases have been reported in vitro and in vivo. On the other hand, chemical bonding between the two structures leading to n-3 lipophenol derivatives (or phenolipids) has been studied in numerous works over the last decade, and some examples could also be found from natural sources. Interest in lipophilization of phenolic structures is various and depends on the domain of interest: in food industry, the development of lipidic antioxidants could be performed to protect lipidic food matrix from oxidation. Whereas, on pharmaceutical purpose, increasing the lipophilicity of polar phenolic drugs could be performed to improve their pharmacological profile. Moreover, combining both therapeutic aspects of n-3 PUFAs and of polyphenols in a single lipophenolic molecule could also be envisaged. An overview of the synthesis and of the natural sources of n-3 lipophenols is presented here, in addition to their biological activities which point out in several cases the benefit of the conjugated derivatives.

show abstract

“…344 The diacylglycerol 301 was reported from Zonaria diesingiana (unspecified location, South China Sea), 345 while ishigoside 302 was isolated from Ishige okamurae (Busan, S. Korea). In 2009 well over half of the $60 papers published were descriptive in nature, or dealt with sulfated polysaccharide (fucoidan) chemistry.…”

Section: Brown Algaementioning

confidence: 99%