Amino Alcohols from the Ascidian Pseudodistoma sp.

Won, Tae Hyung; You, Minjung; Lee, So-Hyoung; Rho, Boon Jo; Oh, Dong‐Chan; Oh, Ki‐Bong; Shin, Jongheon

doi:10.3390/md12063754

Cited by 12 publications

(19 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pseudoaminols A–G ( 27 – 33 , Figure 5 ), obtained from a Pseudistoma sp. collected along the Korean coasts [ 55 ], possess structures closely related to those of crucigasterins. Pseudoaminols F ( 32 ) and G ( 33 ) are the first report of glycine-derived amino alcohols, as attested by the presence, in their structures, of a N -carboxymethyl group [ 55 ].…”

Section: Resultsmentioning

confidence: 99%

“…collected along the Korean coasts [ 55 ], possess structures closely related to those of crucigasterins. Pseudoaminols F ( 32 ) and G ( 33 ) are the first report of glycine-derived amino alcohols, as attested by the presence, in their structures, of a N -carboxymethyl group [ 55 ]. All compounds 27 – 33 were screened for their antibacterial activity against strains of Gram-positive and Gram-negative bacteria.…”

Section: Resultsmentioning

confidence: 99%

“…Pseudoaminols A and B (27 and 28) displayed significant activity against all the tested bacterial strains except for E. coli (Table 1); the effects were similar for the two compounds except for Salmonella typhimurium, where 27 was more potent than 28 ( Table 1). Both pseudoaminols A and B were slightly cytotoxic against pulmonary adenocarcinoma A549 and chronic myeloid leukaemia K562 cell lines, too [55].…”

Section: Saturated and Unsaturated Amino Alcoholsmentioning

confidence: 96%

“…The reduction of polarity and/or basicity of the amino and hydroxyl groups, for example, with the introduction of a N-carboxymethyl substituent, as in the inactive compounds 32 and 33, emphasizes the crucial role played by these functions in the bioactivity either for electronic effects or steric hindrance [55]. Moreover, the above data suggest that the number of double bonds in the amino alcohols alkyl chain strongly affects the antimicrobial activity, too; if within the group of pseudoaminols, it seems that, as the number of double bonds increases, the activity decreases [55], and the saturated amino alcohol (2S, 3R)-2-aminododecan-3-ol (34, Figure 5), isolated from a sample of Clavelina oblonga when tested on both oxacillin-resistant and sensitive strain of S. aureus, was Biosynthetic studies strongly suggested that these derivatives are produced starting from both fatty acids and either L-or d-alanine. The 2R absolute configuration in compounds 22-24 implied that they should derive from d-alanine, whereas crucigasterins B and E are L-alanine derivatives [53,54].…”

Section: Saturated and Unsaturated Amino Alcoholsmentioning

confidence: 99%

See 3 more Smart Citations

The Ascidian-Derived Metabolites with Antimicrobial Properties

2020

View full text Add to dashboard Cite

Among the sub-phylum of Tunicate, ascidians represent the most abundant class of marine invertebrates, with 3000 species by heterogeneous habitat, that is, from shallow water to deep sea, already reported. The chemistry of these sessile filter-feeding organisms is an attractive reservoir of varied and peculiar bioactive compounds. Most secondary metabolites isolated from ascidians stand out for their potential as putative therapeutic agents in the treatment of several illnesses like microbial infections. In this review, we present and discuss the antibacterial activity shown by the main groups of ascidian-derived products, such as sulfur-containing compounds, meroterpenes, alkaloids, peptides, furanones, and their derivatives. Moreover, the direct evidence of a symbiotic association between marine ascidians and microorganisms shed light on the real producers of many extremely potent marine natural compounds. Hence, we also report the antibacterial potential, joined to antifungal and antiviral activity, of metabolites isolated from ascidian-associate microorganisms by culture-dependent methods.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Saturated and Unsaturated Amino Alcoholsmentioning

confidence: 96%

Section: Saturated and Unsaturated Amino Alcoholsmentioning

confidence: 99%

See 2 more Smart Citations

The Ascidian-Derived Metabolites with Antimicrobial Properties

2020

View full text Add to dashboard Cite

show abstract

“…In our continuing search for bioactive metabolites from Korean ascidians [ 19 , 20 , 21 , 22 ], we recently encountered the reddish orange Aplidium sp. off the coast of Chuja-do, Korea, whose organic extract exhibited significant cytotoxicity (IC 50 38.6 µg/mL) for the A549 cancer cell-line.…”

Section: Introductionmentioning

confidence: 99%

Amino Acid-Derived Metabolites from the Ascidian Aplidium sp.

et al. 2015

Self Cite

View full text Add to dashboard Cite

Four new iodobenzene-containing dipeptides (1–4), a related bromotryptophan-containing dipeptide (5), and an iodophenethylamine (6) were isolated from the ascidian Aplidium sp. collected off the coast of Chuja-do, Korea. The structures of these novel compounds, designated as apliamides A–E (1–5) and apliamine A (6) were determined via combined spectroscopic analyses. The absolute configuration of the amino acid residue in 1 was determined by advanced Marfey’s analysis. Several of these compounds exhibited moderate cytotoxicity and significant inhibition against Na+/K+-ATPase (4).

show abstract

Enantioselective Synthesis of Clavaminol A, Xestoaminol C and their Stereoisomers Exhibiting Cytotoxic Activity

et al. 2020

View full text Add to dashboard Cite

The simple preparation of the natural sphingoid bases possessing cytotoxic activity – the marine drugs Clavaminol A and Xestoaminol C and all their unnatural stereoisomers – in high enantiomeric purity (ca. 95 % of major enantiomer) was described. The individual enantiomers were obtained by the utilization of asymmetric Henry reaction. The diastereomers of target compounds were separated by column chromatography after transformation into corresponding 2‐phenyloxazoline derivatives. The individual stereoisomers of Clavaminol A and Xestoaminol C were evaluated for antiproliferative activity in cancer cell lines (A‐549; Jurkat; SH‐SY5Y, MG‐63). From the obtained IC50 values is obvious, that the stereoisomers of Xestoaminol C are more potent inhibitors of cell proliferation than the stereoisomers of Clavaminol A. Further, it was found, that stereoisomers with syn‐configuration exhibited larger antiproliferative effects in comparison with the stereoisomers having anti‐configuration, in both sphingoid bases. Nevertheless, the values of IC50 found for individual enantiomers in each of the enantiomeric pairs are rather comparable implying a possibility of using racemic mixtures for induction of cytotoxicity.

show abstract

Amino Alcohols from the Ascidian Pseudodistoma sp.

Cited by 12 publications

References 26 publications

The Ascidian-Derived Metabolites with Antimicrobial Properties

The Ascidian-Derived Metabolites with Antimicrobial Properties

Amino Acid-Derived Metabolites from the Ascidian Aplidium sp.

Enantioselective Synthesis of Clavaminol A, Xestoaminol C and their Stereoisomers Exhibiting Cytotoxic Activity

Contact Info

Product

Resources

About