Amino Acid-Derived Metabolites from the Ascidian Aplidium sp.

Won, Tae Hyung; Kim, Chang‐Kwon; Lee, So-Hyoung; Rho, Boon Jo; Lee, Sang Kook; Oh, Dong‐Chan; Oh, Ki‐Bong; Shin, Jongheon

doi:10.3390/md13063836

Cited by 12 publications

(3 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The compounds ( 1 ) and ( 3 )– )10 ) were found to be variously bioactive as antibacterial, anticancer, antiparasitic, antiplasmodial, antiinflammatory, and antifouling molecules [ 59 , 60 , 61 , 62 , 63 , 64 ]. A recent study focused on identifying novel marine halogenated tyrosines, identified them as components of valviamides A−D ( 11 – 14 in Table 2 ) from the cnidarians Antipathozoanthus hickmani and Parazoanthus darwini ( Table 2 ).…”

Section: Halo-amino Acids and Halogenated Non-ribosomal Peptidesmentioning

confidence: 99%

Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics

Mardirossian

Rubini

Adamo³

et al. 2021

Molecules

View full text Add to dashboard Cite

The 3D structure and surface characteristics of proteins and peptides are crucial for interactions with receptors or ligands and can be modified to some extent to modulate their biological roles and pharmacological activities. The introduction of halogen atoms on the side-chains of amino acids is a powerful tool for effecting this type of tuning, influencing both the physico-chemical and structural properties of the modified polypeptides, helping to first dissect and then rationally modify features that affect their mode of action. This review provides examples of the influence of different types of halogenation in amino acids that replace native residues in proteins and peptides. Examples of synthetic strategies for obtaining halogenated amino acids are also provided, focusing on some representative compounds and their biological effects. The role of halogenation in native and designed antimicrobial peptides (AMPs) and their mimetics is then discussed. These are in the spotlight for the development of new antimicrobial drugs to counter the rise of antibiotic-resistant pathogens. AMPs represent an interesting model to study the role that natural halogenation has on their mode of action and also to understand how artificially halogenated residues can be used to rationally modify and optimize AMPs for pharmaceutical purposes.

show abstract

Section: Halo-amino Acids and Halogenated Non-ribosomal Peptidesmentioning

confidence: 99%

Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics

Mardirossian

Rubini

Adamo³

et al. 2021

Molecules

View full text Add to dashboard Cite

show abstract

“…Four new iodobenzene containing dipeptides, a related bromotryptophan containing dipeptide, and an iodobenzene amine, have been isolated from the ascidian Aplidium sp. collected from Korean waters [ 149 ]. The compounds displayed moderate cytotoxicity and one, apliamide D, significantly inhibited the Na + /K + -ATPase.…”

Section: Alkaloidsmentioning

confidence: 99%

Ascidian Toxins with Potential for Drug Development

Watters

2018

Marine Drugs

View full text Add to dashboard Cite

Ascidians (tunicates) are invertebrate chordates, and prolific producers of a wide variety of biologically active secondary metabolites from cyclic peptides to aromatic alkaloids. Several of these compounds have properties which make them candidates for potential new drugs to treat diseases such as cancer. Many of these natural products are not produced by the ascidians themselves, rather by their associated symbionts. This review will focus mainly on the mechanism of action of important classes of cytotoxic molecules isolated from ascidians. These toxins affect DNA transcription, protein translation, drug efflux pumps, signaling pathways and the cytoskeleton. Two ascidian compounds have already found applications in the treatment of cancer and others are being investigated for their potential in cancer, neurodegenerative and other diseases.

show abstract

“…The structures of marine natural products are usually characterized by a higher occurrence of halogen atoms than their terrestrial counterparts. Within the marine environment, most of the marine invertebrates but especially algae and sponges are sources of halogenated secondary metabolites. − By far, the most common halogen in marine natural products is bromine. , The incorporation of halogens into natural products is catalyzed by enzymes such as vanadium-dependent haloperoxidases, which have been reported mainly from algae, sponges, or bacteria. ,− Among the different halogenated structural units reported from marine organisms, bromotyrosine derivatives are the most common and mainly found in marine sponges of the order Verongida, − but also some species of ascidians. − Interestingly, a wide range of biological activities including antibacterial, anticancer, antiparasitic, antiplasmodial, anti-inflammatory, and antifouling have been reported for halogenated tyrosine derivatives. − …”

mentioning

confidence: 99%

Halogenated Tyrosine Derivatives from the Tropical Eastern Pacific Zoantharians Antipathozoanthus hickmani and Parazoanthus darwini

et al. 2019

View full text Add to dashboard Cite

In the search for bioactive marine natural products from zoantharians of the Tropical Eastern Pacific, four new tyrosine dipeptides, named valdiviamides A–D (1–4), were isolated from Antipathozoanthus hickmani, and two new tyramine derivatives, 5 and 6, from Parazoanthus darwini. The phenols of all six tyrosine derivatives are substituted by bromine and/or iodine atoms at the ortho positions of the hydroxyl. The planar structures of these aromatic alkaloids were elucidated from 1D and 2D NMR experiments in combination with HRESIMS data, and the absolute configurations of 1–4 were deduced from comparison between experimental and calculated electronic circular dichroism spectra. As halogenated tyrosine derivatives could represent chemotaxonomic markers of these genera, we decided to undertake the first chemical investigation of another species, Terrazoanthus cf. patagonichus. As expected, no halogenated metabolite was evidenced in the species, but we report herein the identification of two new zoanthoxanthin derivatives, named zoamides E (7) and F (8), from this species. Antimicrobial and cytotoxicity bioassays revealed that valdiviamide B (2) displayed moderate cytotoxicity against the HepG2 cell line with an IC50 value of 7.8 μM.

show abstract

Amino Acid-Derived Metabolites from the Ascidian Aplidium sp.

Cited by 12 publications

References 32 publications

Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics

Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics

Ascidian Toxins with Potential for Drug Development

Halogenated Tyrosine Derivatives from the Tropical Eastern Pacific Zoantharians Antipathozoanthus hickmani and Parazoanthus darwini

Contact Info

Product

Resources

About