Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

• Main Authors: Suciati, James A. Fraser, Lynette K. Lambert, Gregory K. Pierens, Paul V. Bernhardt, Mary J. Garson
• Format: Article PeerReviewed
• Language: English; English; English
• Published: American Chemical Society 2013
• Subjects: R Medicine; RS Pharmacy and materia medica
• Online Access: http://repository.unair.ac.id/93609/2/C-08%20Artikel.pdf; http://repository.unair.ac.id/93609/3/C-08%20Reviewer.pdf; http://repository.unair.ac.id/93609/1/C-08%20Result.pdf; http://repository.unair.ac.id/93609/; https://pubs.acs.org/doi/10.1021/np4002114
• Institution: Universitas Airlangga

This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines O (6), P (7), Q (8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (1S, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by 1H NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The 3JH–C values in acremine P were measured using the pulse sequence EXSIDE, and the observed 3JH8–C4 of 5.4 Hz and small 3JH–C values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q, NOESY data combined with molecular modeling established the preferred diastereomer 8a.