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.

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.

scholarly journals Synthesis, Structure Revision, and Absolute Configuration of (+)-Didemniserinolipid B, a Serinol Marine Natural Product from a Tunicate Didemnum sp.

ChemInform ◽  
2003 ◽  
Vol 34 (3) ◽  
Author(s):  
Hiromasa Kiyota ◽  
Darren J. Dixon ◽  
Christine K. Luscombe ◽  
Stephan Hettstedt ◽  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Marine Natural Product ◽  
Structure Revision

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).

Synthesis, Structure Revision, and Absolute Configuration of (+)-Didemniserinolipid B, a Serinol Marine Natural Product from a TunicateDidemnumsp.

2002 ◽  
Vol 4 (19) ◽  
pp. 3223-3226 ◽  
Author(s):  
Hiromasa Kiyota ◽  
Darren J. Dixon ◽  
Christine K. Luscombe ◽  
Stephan Hettstedt ◽  
Steven V. Ley
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Marine Natural Product ◽  
Structure Revision

First Determination of the Absolute Stereochemistry of a Naturally Occurring 1,1′-Biphenanthrene, (-)-Blestriarene C, and Its Unexpected Photoracemization.

ChemInform ◽  
2003 ◽  
Vol 34 (6) ◽  
Author(s):  
Tetsutaro Hattori ◽  
Yuhi Shimazumi ◽  
Osamu Yamabe ◽  
Eiji Koshiishi ◽  
Sotaro Miyano
Keyword(s):  
Naturally Occurring ◽  
The Absolute ◽  
Absolute Stereochemistry

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.

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.

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.

Synthesis and Antitumor Activity of Novel [1,2,4,5]-tetrazepino[6,7-b] indole Derivatives: Marine Natural Product Hyrtioreticuline C and D Analogues

2018 ◽  
Vol 19 (1) ◽  
pp. 79-86 ◽  
Author(s):  
Zeinab A. Muhammad ◽  
Mohamed A.A. Radwan ◽  
Thoraya A. Farghaly ◽  
Hatem M. Gaber ◽  
Mahmuod M. Elaasser
Keyword(s):  
Natural Product ◽  
Carcinoma Cell ◽  
Biologically Active ◽  
Marine Natural Product ◽  
Basic Medium ◽  
Standard Drug ◽  
Reference Drug ◽  
Carcinoma Cell Lines ◽  
Naturally Occurring ◽  
Wide Range

Background: Several biologically active indole alkaloids have been isolated from marine organisms over the previous few years. Many scientsts interested in synthesis of the marine azepinoindole alkaloids due to their wide range of bioliogical activies. </P><P> Objective: We interested herein to synthesize a new series of some analogues of new naturally occurring azepinoindole alkaloids. </P><P> Method: A novel series of [1,2,4,5]tetrazepino[6,7-b]indoles, Marine natural product Hyrtioreticuline C and D analogues, were synthesized via the reaction of 3-hydrazonoindolin-2-one with hydrzaonoyl chlorides in basic medium. </P><P> Results: The spectral data of the products proved their structure. All new derivatives were tested against two carcinoma cell lines ((A-549 & HepG2)) in comparison with the well-known anticancer standard drug (cisplatin) and two derivatives from the tested compounds showed activity more potent than the reference drug. </P><P> Conclusion: We succeeded in synthesis of new antitumor active azepinoindole alkaloids.

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