Cadiolides J–M, antibacterial polyphenyl butenolides from the Korean tunicate Pseudodistoma antinboja

Wang, Weihong; Kim, Hiyoung; Patil, Rahul Shivaji; Giri, Awadut G.; Won, Dong Hwan; Hahn, Dongyup; Sung, Youjung; Lee, Jusung; Choi, Hyukjae; Nam, Sang Jip; Kang, Heonjoong

doi:10.1016/j.bmcl.2016.12.016

Cited by 19 publications

(18 citation statements)

References 12 publications

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“…This suggested both of the distinct HPLC fractions contained the same two separate compounds. This has been observed before for rubrolides O, P, Q, and also cadiolide F [25,32], all of which all exist as two separable but interchangeable isomers, differing by their Δ5,6 geometry. All The remaining peaks in the 1 H NMR spectrum were assigned to the minor rubrolide U isomer (E-4), based on relative peak intensity of the resonances in the two separate HPLC fractions, one enriched in E-4 and the other Z-4, in conjunction with chemical shift values and NOE (ROESY) (Figure 4) data.…”

Section: Resultssupporting

confidence: 77%

Section: Resultssupporting

confidence: 76%

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Targeted Isolation of Rubrolides from the New Zealand Marine Tunicate Synoicum kuranui

et al. 2020

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Global natural products social (GNPS) molecular networking is a useful tool to categorize chemical space within samples and streamline the discovery of new natural products. Here, we demonstrate its use in chemically profiling the extract of the marine tunicate Synoicum kuranui, comprised of many previously reported rubrolides, for new chemical entities. Within the rubrolide cluster, two masses that did not correspond to previously reported congeners were detected, and, following MS-guided fractionation, led to the isolation of new methylated rubrolides T (3) and (Z/E)–U (4). Both compounds showed strong growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis, with minimum inhibitory concentration (MIC) values of 0.41 and 0.91 μM, respectively.

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Section: Resultssupporting

confidence: 77%

Section: Resultssupporting

confidence: 76%

Targeted Isolation of Rubrolides from the New Zealand Marine Tunicate Synoicum kuranui

et al. 2020

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“…However, it Further studies of Synoicum sp. ascidian offshore of Keomun-do Island in Korea afforded the isolation of isocadiolides A-H (127)(128)(129)(130)(131)(132)(133)(134), likely produced by rearrangements followed by oxidization of the furanone ring. These compounds are polybrominated aromatics that possess a tris-bromohydroxyphenil moiety linked to varied cores such as a cyclopentenedione, a dihydrofuran, or a pyranone ring (Figure 13) [135].…”

Section: Ascidians-associated Actinobacteria As Producers Of Antimicrmentioning

confidence: 99%

“…Chemical modification of the structural core determined a significant decrease of bioactivity; all isocadiolides exhibited a weaker activity than the relevant cadiolides. Among compounds 127-134, isocadiolide C (129) was the most potent against S. aureus, with an MIC of 4 µg/mL, together with isocadiolides A, B, and D (127, 128, 130; 16 < MIC (µg/mL) < 32); the Gram-positive E. faecalis was significantly compromised by isocadiolides G (133), which had MIC = 8 µg/mL, whereas isocadiolide B (128) possessed the same MIC against P. hauseri.…”

Section: Ascidians-associated Actinobacteria As Producers Of Antimicrmentioning

confidence: 99%

The Ascidian-Derived Metabolites with Antimicrobial Properties

2020

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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.

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“…The reports on the antibacterial macromolecules from tunicates are relatively few, which led Wang et al to isolate and identify butenolide metabolites from Pseudodistoma antinboja (South Sea, Korea). These class of cadiolide, cadiolides J-M, 1, 3-5, and cadiolide H (2) exhibited considerable antimicrobial activity comparable to the commercial drugs (such as vancomycin and linezolid) against pathogens including four strains of MRSA (1-8 µg/mL) [124].…”

Section: Marine-derived Antimicrobial Compounds From Invertebratesmentioning

confidence: 94%

Antibiotics Development and the Potentials of Marine-Derived Compounds to Stem the Tide of Multidrug-Resistant Pathogenic Bacteria, Fungi, and Protozoa

et al. 2020

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As the search for new antibiotics continues, the resistance to known antimicrobial compounds continues to increase. Many researchers around the world, in response to antibiotics resistance, have continued to search for new antimicrobial compounds in different ecological niches such as the marine environment. Marine habitats are one of the known and promising sources for bioactive compounds with antimicrobial potentials against currently drug-resistant strains of pathogenic microorganisms. For more than a decade, numerous antimicrobial compounds have been discovered from marine environments, with many more antimicrobials still being discovered every year. So far, only very few compounds are in preclinical and clinical trials. Research in marine natural products has resulted in the isolation and identification of numerous diverse and novel chemical compounds with potency against even drug-resistant pathogens. Some of these compounds, which mainly came from marine bacteria and fungi, have been classified into alkaloids, lactones, phenols, quinones, tannins, terpenes, glycosides, halogenated, polyketides, xanthones, macrocycles, peptides, and fatty acids. All these are geared towards discovering and isolating unique compounds with therapeutic potential, especially against multidrug-resistant pathogenic microorganisms. In this review, we tried to summarize published articles from 2015 to 2019 on antimicrobial compounds isolated from marine sources, including some of their chemical structures and tests performed against drug-resistant pathogens.

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Cadiolides J–M, antibacterial polyphenyl butenolides from the Korean tunicate Pseudodistoma antinboja

Cited by 19 publications

References 12 publications

Targeted Isolation of Rubrolides from the New Zealand Marine Tunicate Synoicum kuranui

Targeted Isolation of Rubrolides from the New Zealand Marine Tunicate Synoicum kuranui

The Ascidian-Derived Metabolites with Antimicrobial Properties

Antibiotics Development and the Potentials of Marine-Derived Compounds to Stem the Tide of Multidrug-Resistant Pathogenic Bacteria, Fungi, and Protozoa

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