Secondary metabolites of the sponge-derived fungus Acremonium persicinum

Suciati, Fraser, James A., Lambert, Lynette K., Pierens, Gregory K., Bernhardt, Paul V. and Garson, Mary J. (2013) Secondary metabolites of the sponge-derived fungus Acremonium persicinum. Journal of Natural Products, 76 8: 1432-1440. doi:10.1021/np4002114

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Author Suciati
Fraser, James A.
Lambert, Lynette K.
Pierens, Gregory K.
Bernhardt, Paul V.
Garson, Mary J.
Title Secondary metabolites of the sponge-derived fungus Acremonium persicinum
Formatted title
Secondary metabolites of the sponge-derived fungus Acremonium persicinum
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 0163-3864
1520-6025
Publication date 2013-08-23
Year available 2013
Sub-type Article (original research)
DOI 10.1021/np4002114
Open Access Status File (Author Post-print)
Volume 76
Issue 8
Start page 1432
End page 1440
Total pages 9
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Abstract This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines 0 (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 (IS, 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 H-1 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 (3)J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed (3)J(H8-C4) of 5.4 Hz and small (3)J(H-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.
Formatted abstract
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.
Keyword Marine
Byssoides
Strain
NMR
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
Centre for Advanced Imaging Publications
 
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Citation counts: TR Web of Science Citation Count  Cited 12 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 15 times in Scopus Article | Citations
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Created: Fri, 02 Aug 2013, 19:20:01 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences