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N-Acetyl-α-hydroxy-β-oxotryptamine, a racemic natural product isolated from Streptomyces sp. 80H647

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Abstract

N-acetyl-α-hydroxy-β-oxotryptamine (1) along with N-acetyl-β-oxotryptamine (2) and pimprinine (3) were isolated from the culture broth of Streptomyces sp. 80H647. Compound 1 was found to be a racemate via X-ray diffraction analysis and the enantiomers were successfully purified by chiral-phase HPLC. The absolute configuration was assigned by comparison of the calculated and experimental ECD spectra. The α-hydroxy moiety of 1 was vital for cytotoxicity against different cancer cell lines.

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References

  1. Lancianesi S, Palmieri A, Petrini M. Synthetic approaches to 3-(2-Nitroalkyl) indoles and their use to access tryptamines and related bioactive compounds. Chem Rev 2014;114:7108–49.

    Article  CAS  Google Scholar 

  2. Kochanowska-Karamyan AJ, Hamann MT. Marine indole alkaloids: potential new drug leads for the control of depression and anxiety. Chem Rev 2010;110:4489–97.

    Article  CAS  Google Scholar 

  3. Bode HB, Bethe B, Hofs R, Zeeck A. Big effects from small changes: possible ways to explore nature’s chemical diversity. ChemBioChem 2002;3:619–27.

    Article  CAS  Google Scholar 

  4. Zarins-Tutt JS, et al. Prospecting for new bacterial metabolites: a glossary of approaches for inducing, activating and upregulating the biosynthesis of bacterial cryptic or silent natural products. Nat Prod Rep. 2015;33:54–72.

    Article  Google Scholar 

  5. Isono K, et al. Ascamycin and dealanylascamycin, nucleoside antibiotics from Streptomyces sp. J Antibiot. 1984;37:670–2.

    Article  CAS  Google Scholar 

  6. Lopez JAV, Nogawa T, Futamura Y, Shimizu T, Osada HJ. Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647. J Antibiot. 2019;72:991–5.

    Article  CAS  Google Scholar 

  7. Rawa MSA, et al. A new peptaibol, RK-026A, from the soil fungus Trichoderma sp. RK10-F026 by culture condition-dependent screening. Biosci Biotech Biochem. 2021;85:69–76.

    Article  Google Scholar 

  8. Chen Y, Zeeck A, Chen Z, Zahner H. Metabolic products of microorganisms. 222. β-oxotryptamine derivatives isolated from Streptomyces ramulosus. J Antibiot 1983;36:913–5.

    Article  CAS  Google Scholar 

  9. Raju R, Gromyko O, Fedorenko V, Luzhetskyy A, Muller R. Pimprinols A–C, from the terrestrial actinomycete, Streptomyces sp. Tetrahedron Lett. 2012;53:3009–11.

    Article  CAS  Google Scholar 

  10. O’Connor SE, Maresh JJ. Chemistry and biology of monoterpene indole alkaloid biosynthesis. Nat Prod Rep. 2006;23:532–47.

    Article  Google Scholar 

  11. Favrot L, Blanchard JS, Vergnolle O. Bacterial GCN5-related N-acetyltransferases: from resistance to regulation. Biochemistry. 2016;55:989–1002.

    Article  CAS  Google Scholar 

  12. Rudolf JD, Chang CY, Ma M, Shen B. Cytochromes P450 for natural product biosynthesis in streptomyces: sequence, structure, and function. Nat Prod Rep. 2017;34:1141–72.

    Article  CAS  Google Scholar 

  13. Finefield JM, Sherman DH, Kreitman M, Williams RM. Enantiomeric natural products: occurrence and biogenesis. Angew Chem Int Ed 2012;51:4802–36.

    Article  CAS  Google Scholar 

  14. Backlund PS, et al. Daily rhythm in plasma N-acetyltryptamine. J Biol Rhythm 2017;32:195–211.

    Article  CAS  Google Scholar 

  15. Valdes-Tovar M, et al. Circadian modulation of neuroplasticity by melatonin: a target in the treatment of depression. Brit J Pharmacol 2018;175:3200–8.

    Article  CAS  Google Scholar 

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Acknowledgements

We thank Dr. T. Kawamura for the ROS assay. The computer calculation using Gaussian 16 was performed using the HOKUSAI supercomputer at RIKEN.

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Correspondence to Hiroyuki Osada.

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Lopez, J.A.V., Nogawa, T., Futamura, Y. et al. N-Acetyl-α-hydroxy-β-oxotryptamine, a racemic natural product isolated from Streptomyces sp. 80H647. J Antibiot 74, 477–479 (2021). https://doi.org/10.1038/s41429-021-00420-7

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