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.

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).

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).

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.

Parguerenes Revisited: New Brominated Diterpenes From the Southern Australian Marine Red Alga Laurencia Filiformis

1996 ◽  
Vol 49 (1) ◽  
pp. 19 ◽  
Author(s):  
SJ Rochfort ◽  
RJ Capon
Keyword(s):  
Natural Product ◽  
Biosynthetic Pathway ◽  
Spectroscopic Analysis ◽  
Red Alga ◽  
Biosynthetic Precursor ◽  
Chemical Correlation ◽  
New Compounds

Five new pargueranes, 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol 2,7,16-triacetate (20), 15-bromoparguer-9(11)-ene-2,7,16-triol 2,7-diacetate (21), 15-bromoparguer-9(11)-ene-2,16-diol 2-acetate (22), 15-bromoparguer-9(11)-en-16-ol (23) and 15-bromoisoparguer-9(11)-en-16-ol (24), together with a plausible biosynthetic precursor, preparguerene (25), two known parguerenes , 15-bromoparguer-9(11)-ene-2,7,16,19-tetrol tetraacetate (4) and 15-bromoparguer-9(11)-ene-2,7,16-triol 2,16 diacetate (7), and the known algal metabolites (-)- aromadendrene (17), austradiol acetate (18) and austradiol diacetate (19), have been isolated from a collection of the southern Australian marine red alga Laurencia filiformis. The known synthetic parguerane 15-bromoparguer-9(11)-ene-2,7-16-triol triacetate (5) was also found for thefirst time as a natural product. In addition to securing the structures of new compounds by chemical correlation and detailed spectroscopic analysis, a lausible biosynthetic pathway has been proposed linking preparguerene, parguerene, isoparguerene and secoparguerene carbon skeletons.

scholarly journals Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2655 ◽  
Author(s):  
Lei ◽  
Lei ◽  
Zhou ◽  
Hu ◽  
Niu ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Fermentation Broth ◽  
Human Cancer ◽  
Optical Rotation ◽  
Cytotoxic Activities ◽  
Human Cancer Cell Lines ◽  
Chemical Structures ◽  
Ic50 Values ◽  
New Compounds

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.

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).

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.

scholarly journals Natural Product Studies on the Hamigerans

2021 ◽  
Author(s):  
◽  
Ethan Woolly
Keyword(s):  
Amino Acids ◽  
Methyl Ester ◽  
Natural Product ◽  
Structural Elucidation ◽  
The Other ◽  
Nitrogenous Compounds ◽  
New Compounds

<p>This study describes the NMR-directed isolation and structural elucidation of several new and semi-synthesised compounds. Carrying on from the previous examinations on the sponge Hamigera tarangaensis undertaken at VUW resulted in the isolation of an additional seven congeners to the hamigeran family. These included three debrominated analogues (37, 60, 62), an alternative methyl ester analogue (63) and a 4-brominated analogue (64). Two structures with novel functionality were also isolated, which were found in fractions previously not investigated, the nitrile containing hamigeran R (61) and the dimer hamigeran S (65). The isolation of these novel compounds led to the proposal of a biosynthesis from a reaction with hamigeran G (40) and ammonia, similar to the previous nitrogenous hamigerans biosynthesis with amino acids.   Semi-synthesis was undertaken to probe the biosynthesis of these and the other nitrogenous compounds. The results of this produced four new compounds: two imine intermediates, hamigeran G imine (66) and hamigeran B imine (70), a glycine derived hamigeran (68) and the hamigeran D epimer (69).</p>

scholarly journals Dibromopyrrole Alkaloids from the Marine Sponge Acanthostylotella sp

2009 ◽  
Vol 4 (1) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Sherif Saeed Ebada ◽  
RuAngelie Edrada-Ebel ◽  
Nicole J. de Voogd ◽  
Victor Wray ◽  
Peter Proksch
Keyword(s):  
Natural Products ◽  
Carboxylic Acid ◽  
Methyl Ester ◽  
Marine Sponge ◽  
Two Dimensional ◽  
New Compounds

Fourteen dibromopyrrole alkaloids were isolated from the marine sponge Acanthostylotella sp. collected in Indonesia. In addition to the known compounds 4,5-dibromo-N-(methoxy-methyl)-1 H-pyrrole-2-carboxamide (7), 4,5-dibromo-1 H-pyrrole-2-carboxamide (8), mukanadin D (9), (±)-longamide B methyl ester (10), (±)-longamide B (11), (±)-longamide (12), 3,4-dibromo-1 H-pyrrole-2-carboxamide (13), 2-cyano-4,5-dibromo-1 H-pyrrole (14), six compounds were isolated that proved to be new natural products including acanthamides A – D (1 – 4), methyl 3,4-dibromo-1 H-pyrrole-2-carboxylate (5) and 3,5-dibromo-1 H-pyrrole-2-carboxylic acid (6). The structures of the new compounds were unequivocally identified based on one and two dimensional NMR and on HRFTMS as well as by comparison with the literature.

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.

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