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).

A New Alkaloid From an Australian Marine Sponge, Spongosorites sp.

1994 ◽  
Vol 47 (12) ◽  
pp. 2279 ◽  
Author(s):  
S Urban ◽  
RJ Capon ◽  
JNA Hooper
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Ethanol Extract ◽  
Chemical Derivatization ◽  
Dihydro Derivative ◽  
Antibiotic Property

A specimen of a marine sponge, Spongosorites sp., collected in Port Phillip Bay, Victoria, Australia, has yielded the alkaloid (2). The structure of (2) was secured by spectroscopic analysis, chemical derivatization and synthesis of a dihydro derivative (4). The antibiotic property of the crude ethanol extract of this sponge was attributed to (2).

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.

cis-3-Hydroxy-N-methyl-L-proline: a New Amino Acid from a Southern Australian Marine Sponge, Dendrilla sp.

1998 ◽  
Vol 51 (2) ◽  
pp. 169 ◽  
Author(s):  
Robert J. Capon ◽  
Simon P. B. Ovenden ◽  
Tim Dargaville
Keyword(s):  
Amino Acid ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Natural Abundance ◽  
Chemical Derivatization ◽  
Great Australian Bight ◽  
Very High

A specimen of the sponge Dendrilla sp. collected during commercial trawling operations in the Great Australian Bight, Australia, analyses for a very high natural abundance of the new amino acid cis-3-hydroxy-N-methyl-L-proline (1). The complete stereostructure for (1) was determined by spectroscopic analysis and chemical derivatization.

Norterpene Dienes From an Australian Marine Sponge Latrunculia brevis

1991 ◽  
Vol 44 (1) ◽  
pp. 77 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Methyl Esters ◽  
Chemical Derivatization

The norditerpene diene acid (4) and norsesterterpene diene acid (5), along with their corresponding methyl esters (6) and (7), were isolated from an Australian marine sponge, Latrunculia brevis, and their structures determined by detailed spectroscopic analysis, chemical derivatization and degradation. Comment is made on the possible intermediacy of dienes such as (4)-(7) in the biosynthesis of norterpene cyclic peroxides, common to other Latrunculia species from the same locality.

Spongiaquinone Revisited: Structural and Stereochemical Studies on Marine Sesquiterpene/Quinones From a Southern Australian Marine Sponge, Spongia sp.

1993 ◽  
Vol 46 (8) ◽  
pp. 1245 ◽  
Author(s):  
RJ Capon ◽  
DR Groves ◽  
S Urban ◽  
RG Watson
Keyword(s):  
Marine Sponge ◽  
Potassium Salt ◽  
Spectroscopic Analysis ◽  
Chemical Investigation ◽  
Chiroptical Properties ◽  
Naturally Occurring ◽  
Great Australian Bight ◽  
Absolute Stereochemistry ◽  
Unambiguous Assignment

A chemical investigation of a large purple sponge, Spongia sp., from the Great Australian Bight, resulted in the isolation of a new sesquiterpene/quinone (8), together with the known compounds dehydrocyclospongiaquinone-1 (4) and spongiaquinone (2). The last compound was also isolated as the potassium salt (9), this being the first recorded account of a naturally occurring marine sesquiterpene/quinone salt. The structure for (8) was assigned by detailed spectroscopic analysis. A re-investigation into the stereostructure of spongiaquinone (2) resulted in the first unambiguous assignment of absolute stereochemistry, and uncovered the peculiar chiroptical properties of spongiaquinone (2) and its potassium salt (9).

Lamellarins Q and R: New Aromatic Metabolites From an Australian Marine Sponge, Dendrilla cactos

1995 ◽  
Vol 48 (8) ◽  
pp. 1491 ◽  
Author(s):  
S Urban ◽  
L Hobbs ◽  
JNA Hooper ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
New South ◽  
New South Wales ◽  
Chemical Derivatization ◽  
South Wales

A specimen of Dendrilla cactos collected off the coast of New South Wales, Australia, has yielded two new alkaloids, lamellarins Q (19) and R (20), the structures of which were secured by spectroscopic analysis and by chemical derivatization.

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.

Sigmosceptrins A - C: New Norditerpenes from a Southern Australian Marine Sponge, Sigmosceptrella sp.

1997 ◽  
Vol 50 (12) ◽  
pp. 1137 ◽  
Author(s):  
Sean Bassett, ◽  
Simon P. B. Ovenden ◽  
Robert W. Gable ◽  
Robert J. Capon
Keyword(s):  
Structural Analysis ◽  
Single Crystal ◽  
Ethyl Ester ◽  
Marine Sponge ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Methyl Esters ◽  
Chemical Degradation ◽  
X Ray ◽  
Great Australian Bight

A Sigmosceptrella sp. of sponge collected during trawling operations in the Great Australian Bight, Australia, has yielded a series of new norterpenes. These include a new bisnorditerpene, sigmosceptrin-A (5); two new norditerpenes, sigmosceptrin-B (14) and sigmosceptrin-C (15), isolated as their methyl esters (6) and (7) respectively; and an ethylated artefact, sigmosceptrin-B ethyl ester (8). Complete stereostructures were assigned to the sigmosceptrins by spectroscopic analysis, chemical degradation, derivatization, and by a single-crystal X-ray structural analysis. A biosynthetic pathway is proposed that requires a common biosynthetic precursor to both the sigmosceptrins and norterpene cyclic peroxides.

Deoxyspongiaquinones: New Sesquiterpene Quinones and Hydroquinones From a Southern Australian Marine Sponge Euryspongia sp.

1996 ◽  
Vol 49 (5) ◽  
pp. 611 ◽  
Author(s):  
S Urban ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Chemical Investigation ◽  
Great Australian Bight

Chemical investigation of a marine sponge, Euryspongia sp., collected from the Great Australian Bight, Australia, resulted in the isolation of two new sesquiterpene quinones , deoxyspongiaquinone (4) and (E)-chlorodeoxyspongiaquinone (5), as well as two sesquiterpene hydroquinones, deoxyspongiaquinol (6) and (E)-chlorodeoxyspongiaquinol (7). The structures for (4)-(7) were determined by detailed spectroscopic analysis, as well as chemical interconversion and degradation.

Mirabilins (A-F): New Alkaloids From a Southern Australian Marine Sponge, Arenochalina mirabilis

1996 ◽  
Vol 49 (7) ◽  
pp. 767 ◽  
Author(s):  
RA Barrow ◽  
LM Murray ◽  
TK Lim ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Great Australian Bight

An Australian marine sponge Arenochalina mirabilis (Lendenfeld 1887) collected from the Great Australian Bight has been found to contain six tricyclic alkaloids, mirabilins A-F (5)-(10), isolated and identified as their N-acetyl derivatives (11)-(16). Structures for the mirabilins were secured by detailed spectroscopic analysis.

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