Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2021 May 24;19(6):299.
doi: 10.3390/md19060299.

Abyssomicins-A 20-Year Retrospective View

Hans-Peter Fiedler  1
Affiliations
Review

Abyssomicins-A 20-Year Retrospective View

Hans-Peter Fiedler. Mar Drugs. .

Abstract

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.

Keywords: 4-amino-4-deoxychorismate synthase inhibitor; abyssomicins; chorismate pathway.

PubMed Disclaimer

Conflict of interest statement

The author declares no conflict of interest.

Figures

Figure 1
Figure 1
The bacterial chorismate biosynthetic pathway.
Figure 2
Figure 2
Structures of abyssomicin C and atrop-abyssomicin C produced by Verrucosispora maris AB-18-032.
Figure 3
Figure 3
HPLC analysis of a culture filtrate extract from strain AB-18-032 at a fermentation time of 96 h, monitored at 260 nm. Inserts: UV-visible spectra of abyssomicin B, co-eluted C and atrop-C, and D. Reused with permission from [2], copyright owned by Japan Antibiotics Research Association.
Figure 4
Figure 4
Structures of abyssomicins produced by Verrucosispora maris AB-18-032.
Figure 5
Figure 5
Similarity of the diaxial conformation of chorismate with the abyssomicin C core.
Figure 6
Figure 6
Scanning electron micrograph of Verrucosispora sp. AB-18-032. Bar: 1 µm. Reused with permission from [2], copyright owned by Japan Antibiotics Research Association.
Figure 7
Figure 7
Neighbor-joining phylogenetic tree based on nearly complete 16S rDNA sequences of members of the suborder Micromonosporineae. Reused with permission from [2], copyright owned by Japan Antibiotics Research Association.
See this image and copyright information in PMC

References

    1. Fiedler H.-P., Süssmuth R.D., Zähner H., Bull A.T. Polyzyklische Makrolactone. 103 47 472.2 DE. 2003 Oct 1;
    1. Riedlinger J., Reicke A., Zähner H., Krismer B., Bull A.T., Maldonado L.A., Ward A.C., Goodfellow M., Bister B., Bischoff D., et al. Abyssomicins, inhibitors of the para-aminobenzoic acid pathway produced by the marine Verrucosispora strain AB-18-032. J. Antibiot. 2004;57:271–279. doi: 10.7164/antibiotics.57.271. - DOI - PubMed
    1. Bister B., Bischoff D., Ströbele M., Riedlinger J., Reicke A., Wolter F., Bull A.T., Zähner H., Fiedler H.-P., Süssmuth R.D. Abyssomicin C—A polycyclic antibiotic from a marine Verrucosispora strain as an inhibitor of the p-aminobenzoic acid/tetrahydrofolate biosynthetic pathway. Angew. Chem. Int. Ed. 2004;43:2574–2576. doi: 10.1002/anie.200353160. - DOI - PubMed
    1. Keller S., Nicholson G., Drahl C., Sorensen E., Fiedler H.-P., Süssmuth R. Abyssomicins G and H and atrop-abyssomicin from the marine Verrucosispora strain AB-18-032. J. Antibiot. 2007;60:391–394. doi: 10.1038/ja.2007.54. - DOI - PubMed
    1. Keller S., Schadt H.S., Ortel I., Süssmuth R.D. Action of atrop-abyssomicin C as an inhibitor of 4-amino-4-deoxychorismate synthase PabB. Angew. Chem. Int. Ed. 2007;46:8284–8286. doi: 10.1002/anie.200701836. - DOI - PubMed

MeSH terms

Substances

Supplementary concepts

LinkOut - more resources