Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

Suciati and James A. Fraser and Lynette K. Lambert and Gregory K. Pierens and Paul V. Bernhardt and Mary J. Garson (2013) Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum. Journal of Natural Products, 76 (8). pp. 1432-1440. ISSN 0163-3864

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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.

Item Type: Article
Subjects: R Medicine
R Medicine > RS Pharmacy and materia medica
Divisions: 05. Fakultas Farmasi
Lynette K. LambertUNSPECIFIED
Gregory K. PierensUNSPECIFIED
Paul V. BernhardtUNSPECIFIED
Depositing User: Mr M. Fuad Sofyan
Date Deposited: 24 Jan 2020 07:14
Last Modified: 05 Feb 2020 03:17
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