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Wychimicins E and F from a rare actinomycete of the genus Cryptosporangium

The Journal of Antibiotics (2024)Cite this article

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Abstract

Two new spirotetronate class compounds designated wychimicins E (1) and F (2) were isolated from the culture extract of an actinomycete Cryptosporangium sp. RD061707. Their structures were determined through extensive NMR analysis in comparison with wychimicin C. Both compounds lack one hydroxy group in the decalin moiety, and the relative configuration of the remaining hydroxy group was assigned by NMR analysis of triacetylwychimicin E (3). Compounds 1 and 2 showed potent antimicrobial activity against Kocuria rhizophila and Staphylococcus aureus. These compounds were also modestly cytotoxic against P388 murine leukemia cells.

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References

  1. Barka EA, Vatsa P, Sanchez L, et al. Taxonomy, physiology, and natural products of Actinobacteria. Microbiol Mol Biol Rev. 2016;80:1–43.

    Article  PubMed  Google Scholar 

  2. Genilloud O. Actinomycetes: still a source of novel antibiotics. Nat Prod Rep. 2017;34:1203–32.

    Article  PubMed  CAS  Google Scholar 

  3. Parra J, Beaton A, Seipke RF, Wilkinson B, Hutchings MI, Duncan KR. Antibiotics from rare actinomycetes, beyond the genus Streptomyces. Curr Opin Microbiol. 2023;76:102385.

    Article  PubMed  CAS  Google Scholar 

  4. Liu C, Zhang Z, Fukaya K, Urabe D, Harunari E, Oku N, Igarashi Y. Catellatolactams A–C, plant growth-promoting ansamacrolactams from a rare actinomycete of the genus Catellatospora. J Nat Prod. 2022;85:1993–9.

    Article  PubMed  CAS  Google Scholar 

  5. Liu C, Zhang Z, Fukaya K, Oku N, Harunari E, Urabe D, Igarashi Y. Isolation and structure determination of allopteridic acids A–C and allokutzmicin from an unexplored actinomycete of the genus Allokutzneria. J Antibiot. 2023;76:305–15.

    Article  CAS  Google Scholar 

  6. Lu S, Zhou T, Fukaya K, Harunari E, Oku N, Urabe D, Igarashi Y. Krasilnikolides A and B and detalosylkrasilnikolide A, cytotoxic 20-membered macrolides from the genus Krasilnikovia: assignment of anomeric configuration by J-based configuration analysis. J Nat Prod. 2022;85:2796–803.

    Article  PubMed  CAS  Google Scholar 

  7. Saito S, Atsumi K, Zhou T, Fukaya K, Urabe D, Oku N, Karim MRU, Komaki H, Igarashi Y. A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium. Beilstein J Org Chem. 2020;16:1100–10.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  8. Saito S, Xiaohanyao Y, Zhou T, Nakajima-Shimada J, Tashiro E, Triningsih DW, Harunari E, Oku N, Igarashi Y. Phytohabitols A-C, δ-lactone-terminated polyketides from an actinomycete of the genus Phytohabitans. J Nat Prod. 2022;8:1697–703.

    Article  Google Scholar 

  9. Tamura T, Hayakawa M, Hatano K. A new genus of the order Actinomycetales, Cryptosporangium gen. nov., with descriptions of Cryptosporangium arvum sp. nov. and Cryptosporangium japonicum sp. nov. Int J Syst Bacteriol. 1998;48:995–1005.

    Article  PubMed  CAS  Google Scholar 

  10. AntiSMASH. The AntiSMASH project. https://antismash.secondarymetabolites.org. Accessed 18 Mar 2024.

  11. Rinkel J, Dickschat JS. Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum. Beilstein J Org Chem. 2019;15:789–94.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  12. Biological Resource Center, NITE (NBRC). https://www.nite.go.jp/nbrc/. Accessed 14 Jun 2023.

  13. Kimura T, Umekita M, Hatano M, et al. Wychimicins, a new class of spirotetronate polyketides from Actinocrispum wychmicini MI503-A4. J Antibiot. 2022;75:535–41.

    CAS  Google Scholar 

  14. Pouchert CJ, Behnke J. The Aldrich library of 13C and 1H FT NMR spectra. Ed.1. 1993. Milwaukee, Wis.: Aldrich Chemical Co.

  15. Lacoske MH, Theodorakis EA. Spirotetronate polyketides as leads in drug discovery. J Nat Prod. 2015;78:562–75.

    Article  PubMed  CAS  Google Scholar 

  16. Elsayed SS, Genta-Jouve G, Carrión VJ, Nibbering PH, Siegler MA, de Boer W, Hankemeier T, van Wezel GP. Atypical spirotetronate polyketides identified in the underexplored genus Streptacidiphilus. J Org Chem. 2020;85:10648–57.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

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Authors and Affiliations

  1. Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan

    Desy Wulan Triningsih, Noa Yoshizaki & Yasuhiro Igarashi

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  1. Desy Wulan Triningsih
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  2. Noa Yoshizaki
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  3. Yasuhiro Igarashi
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Correspondence to Yasuhiro Igarashi.

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Triningsih, D.W., Yoshizaki, N. & Igarashi, Y. Wychimicins E and F from a rare actinomycete of the genus Cryptosporangium. J Antibiot (2024). https://doi.org/10.1038/s41429-024-00770-y

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