Two Ring-A-Aromatized Bile Acids from the Marine Sponge <i>Sollasella Moretonensis</i>

Lu, Zhenyu; Wagoner, Ryan M. Van; Harper, Mary Kay; Hooper, John N. A.; Ireland, Chris M.

doi:10.1177/1934578x1000501011

Cited by 11 publications

(11 citation statements)

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“…To the best of our knowledge, the dereplicated flavonoids, bile acids, and amino acid-betaine compounds were not reported from Onchidiidae before. However, similar flavonoids from Syphonota geographica 33 , betaines from Elysia chlorotica 53 , and bile acid derivatives from octocorals 37 and sponges 38 were previously reported from other sea slugs or marine invertebrates. www.nature.com/scientificreports/ To conclude, our investigation of the genus Peronia revealed nine distinct clades of COI gene sequences, with P. persiae forming a chemically distinct species, only distributed in the Persian Gulf.…”

Section: Discussionsupporting

confidence: 77%

Section: Discussionsupporting

confidence: 76%

“…cholic acids and chenodeoxycholic acids 34 and show anticancer and antibacterial activities 35 , 36 . Cholesterol was previously reported from Onchidium reevesii (Gray, 1850) 17 , octocorals 37 , and sponges 38 , while there are only a few reports of bile acids and derivatives in other marine invertebrates. Bile acid derivatives in marine invertebrates are considered to be of symbiotic microbial origin 39 .…”

Section: Discussionmentioning

confidence: 99%

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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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Section: Discussionsupporting

confidence: 77%

Section: Discussionsupporting

confidence: 76%

Section: Discussionmentioning

confidence: 99%

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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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“…Interestingly, animals such as sponges [71] and coral [72] synthesize steroids with an aromatized A ring and a C17 side chain and could have activated the ancestral ER [69]. Markov et al synthesized one of these steroids, paraestrol A (Figure 3), which has been found in coral [37,69,72], and reported that paraestrol A is a transcriptional activator of an ancestral SR [69].…”

Section: Figure 4 Comparison Of Estradiol δ5-androstenediol and Cholmentioning

confidence: 99%

Steroid Receptors and Vertebrate Evolution

Baker¹

2019

Preprint

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Considering that life on earth evolved about 3.7 billion years ago, vertebrates are young, appearing in the fossil record during the Cambrian explosion about 542 to 515 million years ago.  Results from sequence analyses of genomes from bacteria, yeast, plants, invertebrates and vertebrates indicate that receptors for adrenal steroids (aldosterone, cortisol), and sex steroids (estrogen, progesterone, testosterone) also are young, with receptors for estrogens and 3-ketosteroids first appearing in basal chordates (cephalochordates: amphioxus), which are close ancestors of vertebrates.  An ancestral progesterone receptor and an ancestral corticoid receptor, the common ancestor of the glucocorticoid and mineralocorticoid receptors, evolved in jawless vertebrates (cyclostomes: lampreys, hagfish).  This was followed by evolution of an androgen receptor and distinct glucocorticoid and mineralocorticoid receptors in cartilaginous fishes (gnathostomes: sharks).  Adrenal and sex steroid receptors are not found in echinoderms: and hemichordates, which are ancestors in the lineage of cephalochordates and vertebrates.  The presence of steroid receptors in vertebrates, in which these steroid receptors act as master switches to regulate differentiation, development, reproduction, immune responses, electrolyte homeostasis and stress responses, argues for an important role for steroid receptors in the evolutionary success of vertebrates, considering that the human genome contains about 22,000 genes, which is not much larger than genomes of invertebrates, such as Caenorhabditis elegans (~18,000 genes) and Drosophila (~14,000 genes).

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“…In the most simple invertebrates, such as sponges, there are no digestive juices and hence no metabolic need for these substances. Among the plethora of structurally diverse steroids isolated from marine invertebrates [14,15], there are only a few reports of bile acids and derivatives, and these isolations have been reported mainly from octocorals [16][17][18], and sponges [19]. These infrequent findings of bile acid derivatives in marine invertebrates are usually considered to be of symbiotic microbial origin, since there are reports of several taxa of marine bacteria associated with sponges, which are capable of producing bile acids [20].…”

Section: -Introductionmentioning

confidence: 99%

Antifouling activity of peracetylated cholic acid, a natural bile acid derivative

et al. 2019

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The antifouling activity of peracetylated cholic acid (1), a bile acid derivative which was isolated in a previous work as a natural product from the Patagonian sponge Siphonochalina fortis, was evaluated in laboratory and field trials. Toxicity and settlement assays were performed with the mussel Mytilus edulis platensis, while the field trials were carried out by addition of the compound to experimental soluble-matrix paints, which were then tested in the sea. The results obtained in this work show that 1 has a good antifouling activity and low toxicity, and the paints aditivated with 0,6 % Wt showed promisory performances in the field trials at the sea. These results confirm the previous hypothesis that the few acetylated and lipophilic bile acid derivatives isolated from marine invertebrates may act as natural antifoulants. Compound 1 is a natural, biodegradable product that can be easily prepared from cholic acid, which in turn can be isolated in industrial scale from cattle bile. All these facts make cholic acid a good scaffold for the preparation of derivatives, which can be natural product-like, effective and sustainable antifouling additives for marine paints and other applications.

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Two Ring-A-Aromatized Bile Acids from the Marine Sponge Sollasella Moretonensis

Cited by 11 publications

References 9 publications

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

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

Steroid Receptors and Vertebrate Evolution

Antifouling activity of peracetylated cholic acid, a natural bile acid derivative

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