Identification of Cyclic Depsipeptides and Their Dedicated Synthetase from Hapsidospora irregularis
- PMID: 28106998
- PMCID: PMC5975237
- DOI: 10.1021/acs.jnatprod.6b00808
Identification of Cyclic Depsipeptides and Their Dedicated Synthetase from Hapsidospora irregularis
Abstract
Seven cyclic depsipeptides were isolated from Hapsidospora irregularis and structurally characterized as the calcium channel blocker leualacin and six new analogues based on the NMR and HRESIMS data. These new compounds were named leualacins B-G. The absolute configurations of the amino acids and 2-hydroxyisocaproic acids were determined by recording the optical rotation values. Biological studies showed that calcium influx elicited by leualacin F in primary human lobar bronchial epithelial cells involves the TRPA1 channel. Through genome sequencing and targeted gene disruption, a noniterative nonribosomal peptide synthetase was found to be involved in the biosynthesis of leualacin. A comparison of the structures of leualacin and its analogues indicated that the A2 and A4 domains of the leualacin synthetase are substrate specific, while A1, A3, and A5 can accept alternative precursors to yield new molecules.
Conflict of interest statement
The authors declare no competing financial interest.
Figures
Similar articles
-
Leualacin, a novel calcium blocker from Hapsidospora irregularis. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties.J Antibiot (Tokyo). 1992 Jun;45(6):899-905. doi: 10.7164/antibiotics.45.899. J Antibiot (Tokyo). 1992. PMID: 1500357
-
Leualacin, a novel calcium blocker from Hapsidospora irregularis. II. Structure determination.J Antibiot (Tokyo). 1992 Jun;45(6):906-13. doi: 10.7164/antibiotics.45.906. J Antibiot (Tokyo). 1992. PMID: 1500358 No abstract available.
-
Tiglicamides A-C, cyclodepsipeptides from the marine cyanobacterium Lyngbya confervoides.Phytochemistry. 2009 Dec;70(17-18):2058-63. doi: 10.1016/j.phytochem.2009.09.010. Epub 2009 Oct 6. Phytochemistry. 2009. PMID: 19815244 Free PMC article.
-
Antimycin-type depsipeptides: discovery, biosynthesis, chemical synthesis, and bioactivities.Nat Prod Rep. 2016 Oct 28;33(10):1146-65. doi: 10.1039/c6np00004e. Epub 2016 Jun 16. Nat Prod Rep. 2016. PMID: 27307039 Review.
-
Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi.Molecules. 2018 Jan 15;23(1):169. doi: 10.3390/molecules23010169. Molecules. 2018. PMID: 29342967 Free PMC article. Review.
Cited by
-
Biosynthesis of depsipeptides, or Depsi: The peptides with varied generations.Protein Sci. 2020 Dec;29(12):2316-2347. doi: 10.1002/pro.3979. Epub 2020 Nov 2. Protein Sci. 2020. PMID: 33073901 Free PMC article. Review.
-
Identification of cyclosporin C from Amphichorda felina using a Cryptococcus neoformans differential temperature sensitivity assay.Appl Microbiol Biotechnol. 2018 Mar;102(5):2337-2350. doi: 10.1007/s00253-018-8792-0. Epub 2018 Feb 2. Appl Microbiol Biotechnol. 2018. PMID: 29396588 Free PMC article.
-
Cadasides, Calcium-Dependent Acidic Lipopeptides from the Soil Metagenome That Are Active against Multidrug-Resistant Bacteria.J Am Chem Soc. 2019 Mar 6;141(9):3910-3919. doi: 10.1021/jacs.8b12087. Epub 2019 Feb 20. J Am Chem Soc. 2019. PMID: 30735616 Free PMC article.
-
The Desotamide Family of Antibiotics.Antibiotics (Basel). 2020 Jul 27;9(8):452. doi: 10.3390/antibiotics9080452. Antibiotics (Basel). 2020. PMID: 32727132 Free PMC article. Review.
-
Structures and function of a tailoring oxidase in complex with a nonribosomal peptide synthetase module.Nat Commun. 2022 Jan 27;13(1):548. doi: 10.1038/s41467-022-28221-y. Nat Commun. 2022. PMID: 35087027 Free PMC article.
References
-
- Chakraborty TK, Ghosh S, Dutta S. Tetrahedron Lett. 2001;42:5085–5088.
-
- Boros C, Smith CJ, Vasina Y, Che Y, Dix AB, Darveaux B, Pearce C. J Antibiot. 2006;59:486–494. - PubMed
-
- Lang G, Kalvelage T, Peters A, Wiese J, Imhoff JF. J Nat Prod. 2008;71:1074–1077. - PubMed
-
- Chung YM, El-Shazly M, Chuang DW, Hwang TL, Asai T, Oshima Y, Ashour ML, Wu YC, Chang FR. J Nat Prod. 2013;76:1260–1266. - PubMed
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
