Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum
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 marin...
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American Chemical Society
2013
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id-langga.936092020-02-05T03:17:38Z http://repository.unair.ac.id/93609/ Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum Suciati James A. Fraser Lynette K. Lambert Gregory K. Pierens Paul V. Bernhardt Mary J. Garson R Medicine RS Pharmacy and materia medica 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. American Chemical Society 2013-07-24 Article PeerReviewed text en http://repository.unair.ac.id/93609/2/C-08%20Artikel.pdf text en http://repository.unair.ac.id/93609/3/C-08%20Reviewer.pdf text en http://repository.unair.ac.id/93609/1/C-08%20Result.pdf 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 https://pubs.acs.org/doi/10.1021/np4002114 doi.org/10.1021/np4002114 |
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R Medicine RS Pharmacy and materia medica Suciati James A. Fraser Lynette K. Lambert Gregory K. Pierens Paul V. Bernhardt Mary J. Garson Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum |
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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. |
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Article PeerReviewed |
author |
Suciati James A. Fraser Lynette K. Lambert Gregory K. Pierens Paul V. Bernhardt Mary J. Garson |
author_facet |
Suciati James A. Fraser Lynette K. Lambert Gregory K. Pierens Paul V. Bernhardt Mary J. Garson |
author_sort |
Suciati |
title |
Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum |
title_short |
Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum |
title_full |
Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum |
title_fullStr |
Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum |
title_full_unstemmed |
Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum |
title_sort |
secondary metabolites of the sponge-derived fungus acremonium persicinum |
publisher |
American Chemical Society |
publishDate |
2013 |
url |
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 |
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