Marine Spirotetronates: Biosynthetic Edifices That Inspire Drug Discovery

Braddock, Alexander A; Theodorakis, Emmanuel A.

doi:10.3390/md17040232

Cited by 20 publications

(12 citation statements)

References 131 publications

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“…The importance of spirotetronate antibiotics and their improved synthetic routes are highlighted in two review articles by the group of E.A. Theodorakis [ 17 , 18 ].…”

Section: Structure Elucidation and Synthesis Strategiesmentioning

confidence: 99%

Abyssomicins—A 20-Year Retrospective View

Fiedler

2021

Marine Drugs

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Abyssomicins represent a new family of polycyclic macrolactones. The first described compounds of the abyssomicin family were abyssomicin B, C, atrop-C, and D, produced by the marine actinomycete strain Verrucosispora maris AB-18-032, which was isolated from a sediment collected in the Sea of Japan. Among the described abyssomicins, only abyssomicin C and atrop-abyssomicin C show a high antibiotic activity against Gram-positive bacteria, including multi-resistant and vancomycin-resistant strains. The inhibitory activity is caused by a selective inhibition of the enzyme 4-amino-4-deoxychorismate synthase, which catalyzes the transformation of chorismate to para-aminobenzoic acid, an intermediate in the folic acid pathway.

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“…The importance of spirotetronate antibiotics and their improved synthetic routes are highlighted in two review articles by the group of E.A. Theodorakis [ 17 , 18 ].…”

Section: Structure Elucidation and Synthesis Strategiesmentioning

confidence: 99%

Abyssomicins—A 20-Year Retrospective View

Fiedler

2021

Marine Drugs

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“…Compounds 1 and 2 are new members of the spirotetronate-class antibiotics, characterized by a macrocyclic structure containing a trans -decalin unit and a tetronic acid moiety spiro-linked with a cyclohexene ring. To date, more than 100 compounds [ 21 – 22 ], including tetrocarcin [ 23 ] and kijanimicin [ 24 ], are known within the spirotetronate class. Of these, nomimicins A–C ( 4 , 1 , and 2 ) are featured by the smallest macrocyclic ring and highly oxygenated dehydrodecalin moiety.…”

Section: Discussionmentioning

confidence: 99%

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

Zhang

Zhou

Yang

et al. 2021

Beilstein J. Org. Chem.

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Three new tetronate-class polyketides, nomimicins B, C, and D, along with nomimicin, hereafter named nomimicin A, were isolated from the culture extract of Actinomadura sp. AKA43 collected from floating particles in the deep-sea water of Sagami Bay, Japan. The structures of nomimicins B, C, and D were elucidated through the interpretation of NMR and MS analytical data, and the absolute configuration was determined by combination of NOESY/ROESY and ECD analyses. Nomimicins B, C, and D showed antimicrobial activity against Gram-positive bacteria, Kocuria rhizophila and Bacillus subtilis, with MIC values in the range of 6.5 to 12.5 μg/mL. Nomimicins B and C also displayed cytotoxicity against P388 murine leukemia cells with IC50 values of 33 and 89 μM, respectively.

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“…These compounds are divided into two classes: tetronates and spirotetronates, and show a vast structural and functional diversity. Some compounds show antimicrobial activity against Gram-positive bacteria, whereas some show antitumor and anti-retroviral activity [430,431]. Tetronomycin is a linear polyether type tetronate inhibiting the growth of Gram-positive bacteria.…”

Section: Other Antibioticsmentioning

confidence: 99%

Comparison of Antibiotic Resistance Mechanisms in Antibiotic-Producing and Pathogenic Bacteria

Ogawara

2019

Molecules

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Antibiotic resistance poses a tremendous threat to human health. To overcome this problem, it is essential to know the mechanism of antibiotic resistance in antibiotic-producing and pathogenic bacteria. This paper deals with this problem from four points of view. First, the antibiotic resistance genes in producers are discussed related to their biosynthesis. Most resistance genes are present within the biosynthetic gene clusters, but some genes such as paromomycin acetyltransferases are located far outside the gene cluster. Second, when the antibiotic resistance genes in pathogens are compared with those in the producers, resistance mechanisms have dependency on antibiotic classes, and, in addition, new types of resistance mechanisms such as Eis aminoglycoside acetyltransferase and self-sacrifice proteins in enediyne antibiotics emerge in pathogens. Third, the relationships of the resistance genes between producers and pathogens are reevaluated at their amino acid sequence as well as nucleotide sequence levels. Pathogenic bacteria possess other resistance mechanisms than those in antibiotic producers. In addition, resistance mechanisms are little different between early stage of antibiotic use and the present time, e.g., β-lactam resistance in Staphylococcus aureus. Lastly, guanine + cytosine (GC) barrier in gene transfer to pathogenic bacteria is considered. Now, the resistance genes constitute resistome composed of complicated mixture from divergent environments.

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Marine Spirotetronates: Biosynthetic Edifices That Inspire Drug Discovery

Cited by 20 publications

References 131 publications

Abyssomicins—A 20-Year Retrospective View

Abyssomicins—A 20-Year Retrospective View

Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

Comparison of Antibiotic Resistance Mechanisms in Antibiotic-Producing and Pathogenic Bacteria

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