Wakodecaline A, B

Structure
A: NPEdia
Wakodecaline A
B: NPEdia
Wakodecaline B
Producing organism
Pyrenochaetopsis sp. RK10-F058
Biological activity
moderate antimalarial activity
Abstract
Two new decaline metabolites, wakodecalines A and B, were isolated from a fungus, Pyrenochaetopsis sp. RK10-F058, by screening for structurally unique metabolites using LC/MS analysis. Their structures were determined on the basis of NMR and mass spectrometric measurements. The absolute structures were confirmed by a combination of chemical methods including chemical degradation, a modified Mosher’s method and Marfey’s method, and comparison of the experimental electronic CD (ECD) spectrum with calculated one. Both compounds had a cyclopentanone-fused decaline skeleton and an N-methylated amino acid moiety derived from a serine. They showed moderate antimalarial activity against the Plasmodium falciparum 3D7 strain.
References
  • Nogawa T, Kato N, Shimizu T, Okano A, Futamura Y, Takahashi S, Osada H.: Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058.
    J Antibiot, 71, 123–128 (2018) PMID: 28901329 [ doi: 10.1038/ja.2017.103 ]
  • Additional information