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.

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).

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.

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.

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).

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.

The Luffarins (A-Z), Novel Terpenes From an Australian Marine Sponge, Luffariella geometrica

1992 ◽  
Vol 45 (10) ◽  
pp. 1705 ◽  
Author(s):  
MS Butler ◽  
RJ Capon
Keyword(s):  
Natural Products ◽  
Marine Sponge ◽  
Coastal Waters ◽  
Marine Natural Products ◽  
Spectroscopic Analysis ◽  
Marine Metabolites ◽  
Chemical Correlation ◽  
The Absolute ◽  
Great Australian Bight ◽  
Absolute Stereochemistry

A marine sponge, Luffariella geometrica Kirkpatrick, collected from the southern Australian coastal waters of the Great Australian Bight, has been found to contain 14 new bicyclic sesterterpenes, luffarin-A (14), -B (15), -C (16), -D (17), -E (18), -F (19), -G (20), -H (21), -I (22), -J (23), -K (24), -L (25), -M (26) and -N (27), a new bicyclic bisnorsesterterpene, luffarin-O (30), a new monocyclic sesterterpene, luffarin-P (32), six new acyclic sesterterpenes, luffarin-Q (35), -R (36), -S (37), -T (38), -U (39) and -V (40), two new diterpenes, luffarin-W (41) and -X (44), and two new bisnorditerpenes luffarin-Y (45) and -Z (46). These novel marine metabolites have been assigned structures, including stereochemistry, on the basis of detailed spectroscopic analysis, chemical correlation, derivatization, and biosynthetic considerations. Studies directed at the absolute stereochemistry of the luffarins have also permitted assignment of absolute stereochemistry to the known marine natural products (E)-neomanoalide (3), (Z)-neomanoalide (4) and dehydroambliol-A (47).

Two New Scalarane Sesterterpenes: Isoscalarafuran-A and -B, Epimeric Alcohols From a Southern Australian Marine Sponge, Spongia hispida

1993 ◽  
Vol 46 (8) ◽  
pp. 1295 ◽  
Author(s):  
R Davis ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Molecular Modelling ◽  
Spectroscopic Analysis ◽  
Model Compounds ◽  
Great Australian Bight ◽  
New Metabolites

A specimen of the marine sponge Spongia hispida ( Lamarck , 1814), collected in the Great Australian Bight, has yielded the known marine sesterterpene hyrtiosal (1), together with two new scalarane sesterterpenes, isoscalarafuran-A (2) and isoscalarafuran -B (3). The structures for these two new metabolites were secured by detailed spectroscopic analysis, comparison with model compounds, and molecular modelling.

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