A New Sesterterpene Tetronic Acid From an Australian Marine Sponge, Psammocinia sp.

1995 ◽  
Vol 48 (11) ◽  
pp. 1899 ◽  
Author(s):  
L Murray ◽  
H Hamit ◽  
JNA Hooper ◽  
L Hobbs ◽  
RJ Capon
Keyword(s):  
Antimicrobial Activity ◽  
Natural Product ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
Structural Isomer ◽  
Tetronic Acid ◽  
Spectroscopic Characteristics

A new sesterterpene tetronic acid (5) exhibiting antimicrobial activity has been isolated from an Australian marine sponge, Psammocinia sp., and its structure secured by detailed spectroscopic analysis. The tetronic acid (5) possesses almost identical spectroscopic characteristics to, and is a structural isomer of, the known marine natural product (6) previously reported from an Australian sponge.

Two for One: Structure Revision of the Marine Sesterterpene Tetronic Acid Strobilinin to (8Z,13E,20Z)-Strobilinin and (8E,13Z,20Z)-Strobilinin

1994 ◽  
Vol 47 (5) ◽  
pp. 933 ◽  
Author(s):  
R Davis ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
Geometric Isomers ◽  
Tetronic Acid ◽  
Naturally Occurring ◽  
Structure Revision ◽  
Single Compound ◽  
The Absolute ◽  
Absolute Stereochemistry

A reinvestigation of the known marine natural product strobilinin has revealed it not to be a single compound (2), but to consist of two naturally occurring geometric isomers, neither of which corresponds to the structure originally assigned. These isomers, (8E,13Z,20Z)- strobilinin (10) and (8Z,13E,20Z)-strobilinin (11), were resolved, characterized and identified as their respective acetate derivatives (6) and (7), and their structures assigned by spectroscopic analysis. It would appear that the absolute stereochemistry of the strobilinins is very likely opposite to that of co-occurring variabilin (1).

Trunculin-F and Contrunculin-A and -B: Novel Oxygenated Norterpenes From a Southern Australian Marine Sponge, Latrunculia conulosa

1993 ◽  
Vol 46 (9) ◽  
pp. 1363 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Methyl Ester ◽  
Natural Product ◽  
Marine Sponge ◽  
Coastal Waters ◽  
Spectroscopic Analysis ◽  
Marine Natural Product ◽  
New Compounds ◽  
Absolute Stereochemistry

A specimen of Latrunculia conulosa from southern Australian coastal waters, previously observed to contain conulosin-A (6) and conulosin-B (7), has also been found to yield the known marine natural product trunculin-C methyl ester (14), along with three new norterpenes, trunculin-F (10), contrunculin-A (11) and contrunculin-B (12). Trunculin-F (10) was isolated, characterized and identified as its methyl ester (13), and its absolute stereochemistry determined by Horeau analysis. The structures for all new compounds were secured by detailed spectroscopic analysis.

Doubly prenylated tryptamines: cytotoxicity, antimicrobial activity and cyclisation to the marine natural product flustramine A

2013 ◽  
Vol 11 (36) ◽  
pp. 6119 ◽  
Author(s):  
Santosh Kumar Adla ◽  
Florenz Sasse ◽  
Gerhard Kelter ◽  
Heinz-Herbert Fiebig ◽  
Thomas Lindel
Keyword(s):  
Antimicrobial Activity ◽  
Natural Product ◽  
Marine Natural Product

A New Sesterterpene Tetronic Acid From an Australian Sponge, Ircinia sp

1987 ◽  
Vol 40 (7) ◽  
pp. 1327 ◽  
Author(s):  
RJ Capon ◽  
JK Macleod
Keyword(s):  
Antimicrobial Activity ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Tetronic Acid

A new sesterterpene tetronic acid* (2), exhibiting antimicrobial activity, has been isolated from an Australian Ircinia species. The structure elucidation was based on detailed spectroscopic analysis of (2), its acetate (3), and two methylated derivatives (4) and (5).

A New Sesterterpene Tetronic Acid and a Pentaprenylated p-Quinol From an Australian Marine Sponge, Spongia sp.

1992 ◽  
Vol 45 (8) ◽  
pp. 1321 ◽  
Author(s):  
D Lumsdon ◽  
RJ Capon ◽  
SG Thomas ◽  
AA Beveridge
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Tetronic Acid

The sesterterpene tetronic acid (1) and the pentaprenylated p- quinol (2) have been isolated from a specimen of sponge, Spongia sp., collected at a depth of 23 m from Port Phillip Bay, Australia. Structures were assigned on the basis of detailed spectroscopic analysis.

Isopalinurin: a Mild Protein Phosphatase Inhibitor From a Southern Australian Marine Sponge, Dysidea sp.

1993 ◽  
Vol 46 (8) ◽  
pp. 1291 ◽  
Author(s):  
L Murray ◽  
ATR Sim ◽  
JAP Rostas ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Protein Phosphatase ◽  
Spectroscopic Analysis ◽  
Ethanol Extract ◽  
Antibiotic Activity ◽  
Tetronic Acid ◽  
Phosphatase Inhibitor ◽  
Protein Phosphatase Inhibitor

A new sesterterpene tetronic acid, isopalinurin (1), has been isolated from an Australian marine sponge, Dysidea sp., collected in Bass Strait. Isopalinurin (1) was identified as the agent responsible for the antibiotic activity and protein phosphatase inhibitory properties exhibited by the crude ethanol extract, and its structure was secured by detailed spectroscopic analysis.

Cometins (A-C), New Furanosesterterpenes From an Australian Marine Sponge, Spongia sp.

1992 ◽  
Vol 45 (8) ◽  
pp. 1255 ◽  
Author(s):  
S Urban ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Ethanol Extract ◽  
Chemical Derivatization ◽  
Tetronic Acid ◽  
Antibiotic Property ◽  
Great Australian Bight

The known marine furanosesterterpene furospinosulin-1 (1), together with three new furanosesterterpenes, namely cometin-A (2), cometin-B (3) and cometin-C (4), were isolated from a marine sponge, Spongia sp., collected during commercial trawling operations in the Great Australian Bight. The structures of these metabolites were determined by detailed spectroscopic analysis and chemical derivatization . The antibiotic property of the crude ethanol extract of this sponge was attributed solely to the furanosesterterpene tetronic acid cometin -A (2).

Synthesis of Norfijimycin A with Activity against Mycobacterium tuberculosis

2017 ◽  
Vol 70 (2) ◽  
pp. 229 ◽  
Author(s):  
Alexander Stoye ◽  
Gayathri Nagalingam ◽  
Warwick J. Britton ◽  
Richard J. Payne
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Mycobacterium Tuberculosis ◽  
Total Synthesis ◽  
Natural Product ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Marine Natural Product ◽  
Significant Activity ◽  
Methyl Group ◽  
Cyclic Depsipeptide

The total synthesis of norfijimycin A, a simplified analogue of the marine natural product fijimycin A, is described. Fijimycin A is a cyclic depsipeptide that has been shown to possess activity against methicillin-resistant Staphylococcus aureus. The natural product contains a rare N,β-dimethyl leucine unit with unknown stereochemistry at the β-carbon. To evaluate the importance of the β-methyl group for antimicrobial activity, we introduced N-methyl leucine into the natural product scaffold. The resulting norfijimycin A was shown to possess significant activity against Mycobacterium tuberculosis, the etiological agent of tuberculosis.

A New Furanosesterpene From the Marine Sponge Psammocinia rugosa

1989 ◽  
Vol 42 (10) ◽  
pp. 1805 ◽  
Author(s):  
V Liokas ◽  
MJ Garson ◽  
JA Carver
Keyword(s):  
Antimicrobial Activity ◽  
Marine Sponge ◽  
Tetronic Acid

A tetronic acid (5), 5-[13-(furan-3-yl)-2,6,10-trimethyltrideca-2,6,8-trienyl]-4-hydroxy 3-methylfuran-2(5H)-one,* with weak antimicrobial activity has been isolated from the sponge Psammocinia sp. and characterized by analysis of 1H and 13C n.m.r. data including 'H-1H correlation (COSY) experiments. The compound may be identical to a tetronic acid isolated by the Roche group, previously assigned structure (3).

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