Phascoline (N-(3-Guanidinopropionyl)-2-hydroxy-n-heptylamine) and Phascolosomine (N-(3-Guanidinoisobutyryl)-2-methoxy-n-heptylamine), Two New Guanidino Compounds from Sipunculid Worms

Guillou, Yvonne; Robin, Y

doi:10.1016/s0021-9258(19)43557-6

Cited by 11 publications

(9 citation statements)

References 6 publications

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…16,18 The distribution of phascolosomine (7), phascoline (8) and the caruculines within their respective organisms has been investigated, and all compounds have been identified at significantly higher concentrations in the viscera tissue. 8,18 We therefore investigated the distribution of the new phascolosomines A−F (1−6) within the sipunculid worm to determine their relationship with similar annelid metabolites. Six fresh specimens of P. granulatum were dissected to separate the muscular and viscera tissue.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…While P. granulatum contains a diverse array of linear alkaloids, the consistent features among all metabolites are the presence of terminal guanidine and terminal isobutyl moieties connected by an amide-containing chain. The only previously reported metabolites from sipunculid worms were phascolosomine ( 7 ) and phascoline ( 8 ) in 1973 . Phascolosomine A ( 1 ) has a close resemblance with these compounds, featuring the same N -amidino-β-alanine unit, but differs due to a more intricate amide-linked alkyl chain.…”

Section: Results and Discussionmentioning

confidence: 99%

“…The similarities of the new phascolosomines to annelid metabolites have sparked intriguing questions about the biological role of these compounds. Various hypotheses for the role of phascolosomine ( 7 ) and phascoline ( 8 ) have been formed, with the most recent hypothesis suggesting that they may function as toxins due to their in vivo lethality and negative chronotropic activity. , − However, the true functions of these metabolites remain unknown. The complanines and carunculines have excellent data supporting their role as defensive inflammatory irritants. , The distribution of phascolosomine ( 7 ), phascoline ( 8 ) and the caruculines within their respective organisms has been investigated, and all compounds have been identified at significantly higher concentrations in the viscera tissue. , We therefore investigated the distribution of the new phascolosomines A–F ( 1 – 6 ) within the sipunculid worm to determine their relationship with similar annelid metabolites.…”

Section: Results and Discussionmentioning

confidence: 99%

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Highly Concentrated Linear Guanidine Amides from the Marine Sipunculid Phascolosoma granulatum

Jennings,

Kaur,

Ramos

et al. 2024

J. Nat. Prod.

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The chemical diversity of annelids, particularly those belonging to the class Sipuncula, remains largely unexplored. However, as part of a Marine Biodiscovery program in Ireland, the peanut worm Phascolosoma granulatum emerged as a promising source of unique metabolites. The purification of the MeOH/CH 2 Cl 2 extract of this species led to the isolation of six new linear guanidine amides, named phascolosomines A−F (1−6). NMR analysis allowed for the elucidation of their structures, all of which feature a terminal guanidine, central amide linkage, and a terminal isobutyl group. Notably, these guanidine amides were present in unusually high concentrations, comprising ∼3% of the dry mass of the organism. The primary concentration of the phascolosomines in the viscera is similar to that previously identified in linear amides from sipunculid worms and marine fireworms. The compounds from sipunculid worms have been hypothesized to be toxins, while those from fireworms are reported to be defensive irritants. However, screening of the newly isolated compounds for inhibitory bioactivity showed no significant inhibition in any of the assays conducted.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

See 2 more Smart Citations

Highly Concentrated Linear Guanidine Amides from the Marine Sipunculid Phascolosoma granulatum

Jennings,

Kaur,

Ramos

et al. 2024

J. Nat. Prod.

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“…The non‐proteinogenic amino acid βAib is rarely found within natural products, previously reported in only the guanidine phascolosomine from the sipunculid worm Phascolion strombi , [24] and the lipopeptides YM‐170320 and fusaristatins from fungal Candida and Fusarium sp. respectively [25, 26] .…”

Section: Resultsmentioning

confidence: 99%

Euglenatides, Potent Antiproliferative Cyclic Peptides Isolated from the Freshwater Photosynthetic Microalga Euglena gracilis

et al. 2022

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By limiting the nitrogen source to glutamic acid, we isolated cyclic peptides from Euglena gracilis containing asparagine and non-proteinogenic amino acids. Structure elucidation was accomplished through spectroscopic methods, mass spectrometry and chemical degradation. The euglenatides potently inhibit pathogenic fungi and cancer cell lines e.g., euglenatide B exhibiting IC 50 values of 4.3 μM in Aspergillus fumigatus and 0.29 μM in MCF-7 breast cancer cells. In an unprecedented convergence of non-ribosomal peptide synthetase and polyketide synthase assembly-line biosynthesis between unicellular species and the metazoan kingdom, euglenatides bear resemblance to nemamides from Caenorhabditis elegans and inhibited both producing organisms E. gracilis and C. elegans. By molecular network analysis, we detected over forty euglenatide-like metabolites in E. gracilis, E. sanguinea and E. mutabilis, suggesting an important biological role for these natural products.

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β‐Amino Acid Biosynthesis

Spiteller

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Phascoline (N-(3-Guanidinopropionyl)-2-hydroxy-n-heptylamine) and Phascolosomine (N-(3-Guanidinoisobutyryl)-2-methoxy-n-heptylamine), Two New Guanidino Compounds from Sipunculid Worms

Cited by 11 publications

References 6 publications

Highly Concentrated Linear Guanidine Amides from the Marine Sipunculid Phascolosoma granulatum

Highly Concentrated Linear Guanidine Amides from the Marine Sipunculid Phascolosoma granulatum

Euglenatides, Potent Antiproliferative Cyclic Peptides Isolated from the Freshwater Photosynthetic Microalga Euglena gracilis

β‐Amino Acid Biosynthesis

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