Chemical Insights into the Anchinopeptolide Series

Silva, Siguara Bastos Lemos; Beniddir, Mehdi A.; Gallard, Jean‐François; Poupon, Erwan; Thomas, Olivier P.; Evanno, Laurent

doi:10.1002/ejoc.201900625

Cited by 7 publications

(6 citation statements)

References 11 publications

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“…Compound 6 was not detected in the sponge extract but could be synthesized by a photoinduced intramolecular [2+2] cycloaddition. This evidence strongly supports the hypothesis of its artefactual origin [32]. Silva et al (2019) isolated anchinopeptolide E (5), the epimer at C-5′ of compound 3 (Figure 2), from a specimen of P. tenacior collected in France.…”

Section: Anchinopeptolidessupporting

confidence: 65%

Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

et al. 2021

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Porifera, commonly referred to as marine sponges, are acknowledged as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention over the years. They are widespread in all continents, and several structurally unique compounds have been identified from this species. Terpenes, mainly sesterterpenoids, are the major secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have presented interesting biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial, and anti-inflammatory activities have been isolated and structurally characterized. This review provides an overview of almost 130 secondary metabolites from Phorbas sponges and their biological activities, and it covers the literature since the first study published in 1993 until November 2021, including approximately 60 records. The synthetic routes to the most interesting compounds are briefly outlined.

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Section: Anchinopeptolidessupporting

confidence: 65%

Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

et al. 2021

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“…As regards steroids, phorbasterones A-D (29)(30)(31)(32), displayed moderate cytotoxicity toward HCT-116 cells [45]. In support of these observations, more recently, the lipid fraction from P. amaranthus, likely enriched of sterols, was found to possess antiproliferative properties in HCT-116 cells [67].…”

Section: Cytotoxic and Cytostatic Activitymentioning

confidence: 68%

“…Compound 6 was indeed not detected in the sponge extract but could be synthesized by a photoinduced intramolecular [2+2] cycloaddition. This evidence strongly suggest that it has artefactual origin [32]. Silva et al (2019) isolated anchinopeptolide E (5), the epimer at C-5' of compound 3 (Figure 2), from a specimen of P. tenacior collected in France.…”

Section: Anchinopeptolide E Cicloanchinopeptolidementioning

confidence: 99%

“…Mazuno et al reported for the first time the steroids phorbasterones A-D (29-34) from Phorbas amaranthus, collected in Florida [45]. These structures share a characteristic ring A-contracted steroid nucleus and differ from each other by the side chain: phorbasterone A (29) possesses a double bond at C-22 and a methyl group at C-24, phorbasterone B (30) has a fully saturated isoprenyl side chain, phorbasterone Ca and Cb (31)(32) keep the double bond at C-22 and bear an ethyl group with opposite configuration at C-24; finally, phorbasterone Da and Db (33-34) lack the double bond at C-22 but keep the ethyl group at C-24 (Figure 10).…”

Section: Phorbasteronesmentioning

confidence: 99%

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Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Caso¹,

Silva²,

Esposito³

et al. 2021

Preprint

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Porifera, commonly referred to as marine sponges, have stood out as major producers of marine natural products (MNPs). Sponges of the genus Phorbas have attracted much attention along years. They are widespread in all continents, and several structurally unique compounds have been identified from species of this genus. Terpenes, mainly sesterterpenoids, represent the great majority of secondary metabolites isolated from Phorbas species, even though several alkaloids and steroids have also been reported. Many of these compounds have shown a variety of biological activities. Particularly, Phorbas sponges have been demonstrated to be a source of cytotoxic metabolites. In addition, MNPs exhibiting cytostatic, antimicrobial and anti-inflammatory activities, have been isolated and structurally characterized. This work brings an overview of Phorbas secondary metabolites reported since the first study published in 1993 until 2020, and their biological activities.

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“…Epimeric 5a , b are likely formed by dimerization of the aryl pyruvamide 12 (Figure ) through tandem reactions: aldol addition (arbitrarily depicted here as base-promoted) at the electrophilic C-8 keto group, and ring closure through aminal formation. Compounds 5a , b represent a structural motif not seen before in BTAs but preceded in the marine natural products literature by the N -coumaroyl-Ala-derived pyrrolidinones, anchinopeptolides A, B–D, and E, from the sponge Anchinoe tenacior , and Br-Trp-derived pyrrolidinones from two ascidians of the genus Eusynstyela . , …”

Section: Resultsmentioning

confidence: 91%

Bioactive Bromotyrosine Alkaloids from the Bahamian Marine Sponge Aiolochroia crassa. Dimerization and Oxidative Motifs

2022

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Nine bromotyrosine alkaloids (BTAs), including debromoianthelline (1), pseudoceratinic acid (2a), methyl pseudoceratinate (2b), 13-oxo-ianthelline (3), aiolochroiamides A–D (4a,b and 5a,b), and 7-hydroxypurealidin J (6), were isolated from a Bahamian Aiolochroia crassa (Hyatt; previously, Pseudoceratina crassa). The structures of 1–6 were established from 1H, 13C, and 2D NMR spectra, IR, and mass spectrometry data. Compounds 2–4 comprise an O-methyl-2,6-dibromotyrosyl ketoxime (subunit A) amide linked to variable groups (subunit B). Compound 1 is debromoianthelline, and 2a and 2b are amides of 3-aminopropanoic acid and methyl 3-aminopropanoate, respectively. BTAs 3 and 4 are linked to 5-(2-aminoethyl)-2-iminoimidazolidin-4-one and a hexahydropyrrolo[2,3-d]imidazol-2(1H)-imine nucleus, respectively, whereas 5 is a self-dimerization motif of an aryl pyruvamide. Alkaloid 6 contains a spirocyclohexadienyl-isoxazoline-carboxamide amide coupled to 2-aminohistamine similar to that found in purealidin J and aerophobin-1 but with hydroxylation at C-7. The 2,4-diaminobutanoic acid residue in 3 was determined to be a 2:1 L- and D- mixture based on hydrolysis followed by derivatization with L-FDTA and LCMS. Diastereomeric pairs, 4a,b and 5a,b, were racemic. The relative configurations of 4a, 4b, 5a, and 5b were assigned by comparison of 1H and 13C chemical shifts with those calculated by DFT. Compounds 5a,b, ningalamide B (9), and ianthelline (7) moderately inhibited butyrylcholinesterase and Candida and Cryptococcus spp.

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Chemical Insights into the Anchinopeptolide Series

Cited by 7 publications

References 11 publications

Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

Exploring Chemical Diversity of Phorbas Sponges as a Source of Novel Lead Compounds in Drug Discovery

Exploring Chemical Diversity of <em>Phorbas</em> Sponges as a Source of Novel Lead Compounds in Drug Discovery

Bioactive Bromotyrosine Alkaloids from the Bahamian Marine Sponge Aiolochroia crassa. Dimerization and Oxidative Motifs

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