Trunculins G - I: New Norsesterterpene Cyclic Peroxides from a Southern Australian Marine Sponge, Latrunculia sp.

1998 ◽  
Vol 51 (7) ◽  
pp. 573 ◽  
Author(s):  
Simon P. B. Ovenden ◽  
Robert J. Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Methyl Esters ◽  
I 11 ◽  
The Absolute ◽  
Cyclic Peroxide ◽  
Absolute Stereochemistry

A Latrunculia sp. collected off Port Phillip Bay, Victoria, returned three new norsesterterpene cyclic peroxides. Trunculins G (9), H (10) and I (11) were isolated as their methyl esters (12), (13) and (14) respectively. Gross structures for these new trunculins were assigned on the basis of spectroscopic analysis, while the absolute stereochemistry about the cyclic peroxide terminus was established by application of the Horeau and Mosher procedures.

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

1993 ◽  
Vol 46 (8) ◽  
pp. 1255 ◽  
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.

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).

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.

Investigation into the Absolute Stereochemistry of the Marine Sponge Alkaloid Pyrinodemin A.

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
Stuart P. Romeril ◽  
Victor Lee ◽  
Jack E. Baldwin ◽  
Timothy D. W. Claridge ◽  
Barbara Odell
Keyword(s):  
Marine Sponge ◽  
The Absolute ◽  
Absolute Stereochemistry

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).

New Chromenols From a Southern Australian Tunicate, Aplidium solidum

1996 ◽  
Vol 49 (11) ◽  
pp. 1217 ◽  
Author(s):  
SJ Rochfort ◽  
R Metzger ◽  
L Hobbs ◽  
RJ Capon
Keyword(s):  
Spectroscopic Analysis ◽  
Chemical Degradation ◽  
The Absolute ◽  
Absolute Stereochemistry

Two new chromenols, namely (R)-2-methyl-2-(4-methylpenta-1,3-dienyl)-2H-chromen-6-ol (7) and 1-[(R)-6-hydroxy-2-methyl-2H-chromen-2-yl]-4-methylpentan-2-one (8), have been isolated from a southern Australian tunicate, Aplidium solidum. The structures of (7) and (8) were assigned by spectroscopic analysis, and the absolute stereochemistry of (7) by chemical degradation.

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).

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.

scholarly journals Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 353 ◽  
Author(s):  
Idam Hermawan ◽  
Mikako Higa ◽  
Philipus Uli Basa Hutabarat ◽  
Takeshi Fujiwara ◽  
Kiyotaka Akiyama ◽  
...  
Keyword(s):  
Respiratory Syncytial Virus ◽  
Antiviral Activity ◽  
Spectroscopic Analysis ◽  
Computational Study ◽  
Bioactive Molecules ◽  
Chiral Derivatization ◽  
The Absolute ◽  
Syncytial Virus ◽  
Absolute Stereochemistry

On our quest for new bioactive molecules from marine sources, two cyclic imines (1, 2) were isolated from a dinoflagellate extract, inhibiting the growth of the respiratory syncytial virus (RSV). Compound 1 was identified as a known molecule portimine, while 2 was elucidated to be a new cyclic imine, named kabirimine. The absolute stereochemistry of 1 was determined by crystallographic work and chiral derivatization, whereas the structure of 2 was elucidated by means of spectroscopic analysis and computational study on all the possible isomers. Compound 1 showed potent cytotoxicity (CC50 < 0.097 µM) against HEp2 cells, while 2 exhibited moderate antiviral activity against RSV with IC50 = 4.20 µM (95% CI 3.31–5.33).

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.

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