Photochemical activity of membrane-localised polyketide derived marine natural products

Powell, Kimberley Jade; Richens, Joanna L.; Bramble, Jonathan P.; Han, Li; Sharma, Pallavi; O'Shea, Paul; Moses, John E.

doi:10.1016/j.tet.2017.10.056

Cited by 13 publications

(12 citation statements)

References 36 publications

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“…Production of pyrones is thus correlated with the establishment of symbiosis and the increased photosynthesis under initial starvation conditions, but decreases after subsequent kleptoplast degradation. Overall, our data thus strongly support previous suggestions that pyrones are critical for maintaining long-term photosynthetic activity in sacoglossans by serving antioxidant and photoprotective roles 22,23 . Both previous biological studies and previous chemical studies provide experiments that suggest a photosynthetic-protective role for the pyrones 20,21,23,25 , and here we provide further chemical, genomic, and transcriptomic evidence supporting this idea.…”

Section: Expression and Biochemical Analysis Ofsupporting

confidence: 91%

“…The polypropionates react via oxidative and photocyclization pathways that are likely non-enzymatic to form the mature natural products 14,[19][20][21] . It is thought that these reactions protect the slugs from damage associated with photosynthesis, and that they may thus be necessary for a photosynthetic lifestyle [19][20][21][22][23] . Thus, the polypropionates are known to originate in these molluscs and to be central to their biology, yet the biochemical source of the compounds remained unknown.…”

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confidence: 99%

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Animal biosynthesis of complex polyketides in a photosynthetic partnership

et al. 2020

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Complex polyketides are typically associated with microbial metabolism. Here, we report that animals also make complex, microbe-like polyketides. We show there is a widespread branch of fatty acid synthase-(FAS)-like polyketide synthase (PKS) proteins, which sacoglossan animals use to synthesize complex products. The purified sacogolassan protein EcPKS1 uses only methylmalonyl-CoA as a substrate, otherwise unknown in animal lipid metabolism. Sacoglossans are sea slugs, some of which eat algae, digesting the cells but maintaining functional chloroplasts. Here, we provide evidence that polyketides support this unusual photosynthetic partnership. The FAS-like PKS family represents an uncharacterized branch of polyketide and fatty acid metabolism, encoding a large diversity of biomedically relevant animal enzymes and chemicals awaiting discovery. The biochemical characterization of an intact animal polyketide biosynthetic enzyme opens the door to understanding the immense untapped metabolic potential of metazoans.

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Section: Expression and Biochemical Analysis Ofsupporting

confidence: 91%

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confidence: 99%

Animal biosynthesis of complex polyketides in a photosynthetic partnership

et al. 2020

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“…Polypropionates with different carbon skeleton were also described from genus Siphonaria (Gastropoda: Tectipleura) such as Siphonaria baconi Reeve, 1856 (now accepted as Siphonaria zelandica Quoy and Gaimard, 1833) 43 , and Siphonaria diemenensis Quoy and Gaimard, 1833 44 . Moreover, other marine molluscs, like photosynthetic members of the order Sacoglossa, harbor a big complex of different polypropionates acting as photoprotectants and antioxidants within the slugs 45 , 46 . These compounds seem to be common within the Onchidiidae and are reported from various localities, including China, Hawaii, and Australia 18 , 44 , 47 .…”

Section: Discussionmentioning

confidence: 99%

From Persian Gulf to Indonesia: interrelated phylogeographic distance and chemistry within the genus Peronia (Onchidiidae, Gastropoda, Mollusca)

Maniei

Moghaddam

Crüsemann

et al. 2020

Sci Rep

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the knowledge of relationships between taxa is essential to understand and explain the chemical diversity of the respective groups. Here, twelve individuals of the panpulmonate slug Peronia persiae from two localities in persian Gulf, and one animal of P. verruculata from Bangka island, indonesia, were analyzed in a phylogenetic and chemotaxonomic framework. Based on the ABGD test and haplotype networking using coi gene sequences of Peronia specimens, nine well-supported clades were found. Haplotype network analysis highlighted a considerable distance between the specimens of P. persiae and other clades. Metabolomic analysis of both species using tandem mass spectrometrybased GnpS molecular networking revealed a large chemical diversity within Peronia of different clades and localities. While P. persiae from different localities showed a highly similar metabolome, only few identical chemical features were found across the clades. the main common metabolites in both Peronia species were assigned as polypropionate esters of onchitriols and ilikonapyrones, and osmoprotectant amino acid-betaine compounds. On the other hand, the isoflavonoids genistein and daidzein were exclusively detected in P. persiae, while cholesterol and conjugated chenodeoxycholic acids were only found in P. verruculata. flavonoids, bile acids, and amino acid-betaine compounds were not reported before from onchidiidae, some are even new for panpulmonates. our chemical analyses indicate a close chemotaxonomic relation between phylogeographically distant Peronia species. Peronia Fleming, 1822, a panpulmonate slug genus, is typically distributed in tropical and subtropical regions of the Indo-Pacific ocean 1. The genus Peronia, with ten acknowledged species, has been reported from many localities ranging from the Indo-Pacific to the East Coast of Africa and to Hawaii 2-4. Due to undetected cryptic speciation, species diversity is often underestimated while the widespread distributions attributed to species is often overestimated 5. The integration of molecular and morphological methods has led to numerous discoveries of cryptic species complexes 6. This is also true for the genus Peronia, as was shown by Maniei et al. 3. To date, only three Peronia species are well investigated by molecular and/or morphology data, i.e.

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“…The polypropionates react via oxidative and photocyclization pathways that are likely non-enzymatic to form the mature natural products 8–10,16 . It is thought that these reactions protect the slugs from damage associated with photosynthesis, and that they may thus be necessary for a photosynthetic lifestyle 8–12 . Thus, the polypropionates are known to originate in the mollusks and to be central to mollusk biology, yet their biochemical sources were unknown.…”

Section: Mainmentioning

confidence: 99%

“…One FAS-like protein uses only methylmalonyl-CoA as a substrate, otherwise unknown in animal lipid metabolism, and is involved in an intricate partnership between a sea slug and captured chloroplasts. The enzyme’s complex, methylated polyketide product results from a metabolic interplay between algal chloroplasts and animal host cells, and also likely facilitates the survival of both symbiotic partners, acting as a photoprotectant for plastids and an antioxidant for the slug 8–12 . Thus, we find that animals can unexpectedly synthesize a large and medically useful class of structurally complex polyketides previously ascribed solely to microbes, and can use them to promote symbiotic organelle maintenance.…”

mentioning

confidence: 99%