YM-266183 and YM-266184, Novel Thiopeptide Antibiotics Produced by Bacillus cereus Isolated from a Marine Sponge. Part 2. Structure Elucidation.

AbstractVal-Geninthiocin (2), a new member of thiopeptide antibiotics, was isolated from the mycelium of Streptomyces sp. RSF18, along with the closely related geninthiocin (1) and the macrolide, chalcomycin. By intensive NMR and MS studies, Val-geninthiocin (2) was identified as desoxygeninthiocin, a thiopeptide, containing several oxazole and thiazole units and a number of unusual amino acids. Compound 2 shows potent activity against Gram-positive bacteria and minor antifungal activity, while it is not effective against Gram-negative bacteria or microalgae. Here we describe the fermentation, isolation and structure elucidation as well as the biological activity of 2.

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Structurally diverse hamigerans from the New Zealand marine sponge Hamigera tarangaensis: NMR-directed isolation, structure elucidation and antifungal activity

Organic & Biomolecular Chemistry ◽

10.1039/c3ob41305e ◽

2013 ◽

Vol 11 (46) ◽

pp. 8041 ◽

Cited By ~ 26

Author(s):

A. Jonathan Singh ◽

Jonathan D. Dattelbaum ◽

Jessica J. Field ◽

Zlatka Smart ◽

Ethan F. Woolly ◽

...

Keyword(s):

New Zealand ◽

Antifungal Activity ◽

Marine Sponge ◽

Structure Elucidation

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9-(5'-Deoxy-5'-thio-β-D-xylofuranosyl)adenine Disulfide from the Southern Australian Marine Sponge Trachycladus laevispirulifer: the First Natural Occurrence of a Nucleoside Disulfide

Australian Journal of Chemistry ◽

10.1071/ch09645 ◽

2010 ◽

Vol 63 (6) ◽

pp. 873 ◽

Cited By ~ 7

Author(s):

Chongsheng Peng ◽

G. M. Kamal B. Gunaherath ◽

Andrew M. Piggott ◽

Zeinab Khalil ◽

Melissa Conte ◽

...

Keyword(s):

Marine Sponge ◽

Structure Elucidation ◽

Spectroscopic Analysis ◽

Chemical Fractionation ◽

Natural Occurrence ◽

Model Compounds ◽

Anticancer Properties ◽

Synthetic Model ◽

Natural And Synthetic

Chemical fractionation of a southern Australian marine sponge, Trachycladus laevispirulifer, yielded 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide as the first recorded natural occurrence of a nucleoside disulfide, and only the second of a xylo-nucleoside. Structure elucidation of the disulfide was achieved by detailed spectroscopic analysis and comparison to synthetic model compounds. The antibacterial, antifungal, and anticancer properties of the disulfide are documented and the literature surrounding natural and synthetic thionucleosides is reviewed.

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Beyond Polygodial: New Drimane Sesquiterpenes From a Southern Australian Marine Sponge, Dysidea sp.

Australian Journal of Chemistry ◽

10.1071/ch9931255 ◽

1993 ◽

Vol 46 (8) ◽

pp. 1255 ◽

Cited By ~ 22

Author(s):

MS Butler ◽

RJ Capon

Keyword(s):

Marine Sponge ◽

Structure Elucidation ◽

Spectroscopic Analysis ◽

Marine Metabolites ◽

Ecological Relationship ◽

Chemical Correlation ◽

The Absolute ◽

First Time ◽

Absolute Stereochemistry

This report describes the isolation and structure elucidation of four new drimane sesquiterpenes (14)-(17) from a southern Australian marine sponge Dysidea sp. The structures for (14)-(17) were secured by detailed spectroscopic analysis, chemical interconversion and derivatization. Also reported are the known metabolites (+)- euryfuran (7), dihydropallescensin-2 (18), (-)- pallescensin-A (19) and (-)-7-deacetoxyolepupane (6). The rare co-occurrence of two antipodes, (7) and (19), in the same specimen highlights the dangers in assigning absolute stereochemistry based on 'unproven' biosynthetic relationships. The absolute stereochemistry for (6) has been unambiguously established for the first time by chemical interconversion to (7). Furthermore, the absolute stereochemistry of the new marine metabolites listed above, (14)-(17), were determined by chemical correlation to (6). A biosynthetic and ecological relationship is proposed between the metabolites from Dysidea sp. with the known marine and terrestrial antifeedant polygodial (8). Chemical investigations are reported that support this proposition.

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