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).

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.

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).

9-(5'-Deoxy-5'-thio-β-D-xylofuranosyl)adenine Disulfide from the Southern Australian Marine Sponge Trachycladus laevispirulifer: the First Natural Occurrence of a Nucleoside Disulfide

2010 ◽  
Vol 63 (6) ◽  
pp. 873 ◽  
Author(s):  
Chongsheng Peng ◽  
G. M. Kamal B. Gunaherath ◽  
Andrew M. Piggott ◽  
Zeinab Khalil ◽  
Melissa Conte ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Chemical Fractionation ◽  
Natural Occurrence ◽  
Model Compounds ◽  
Anticancer Properties ◽  
Synthetic Model ◽  
Natural And Synthetic

Chemical fractionation of a southern Australian marine sponge, Trachycladus laevispirulifer, yielded 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide as the first recorded natural occurrence of a nucleoside disulfide, and only the second of a xylo-nucleoside. Structure elucidation of the disulfide was achieved by detailed spectroscopic analysis and comparison to synthetic model compounds. The antibacterial, antifungal, and anticancer properties of the disulfide are documented and the literature surrounding natural and synthetic thionucleosides is reviewed.

scholarly journals Epimanool and a New 2,6-Dideoxy-hexopyran-3-ulose Derivative from Celmisia viscosa

2013 ◽  
Vol 8 (6) ◽  
pp. 1934578X1300800
Author(s):  
Catherine E. Sansom ◽  
Lesley Larsen ◽  
Alison C. Evans ◽  
Nigel B. Perry
Keyword(s):  
New Zealand ◽  
Starting Material ◽  
High Yield ◽  
Leaf Surfaces ◽  
The Absolute ◽  
First Time ◽  
Absolute Stereochemistry

Epimanool is reported for the first time in high yield (up to 7% w/w) from the New Zealand endemic shrub Celmisia viscosa (Asteraceae), together with a new derivative, containing the first natural example of a 2,6-dideoxy-hexopyran-3-ulose. The absolute stereochemistry of epimanool was proven by conversion to manool ketone, which also showed the potential of this plant as a source of perfume starting material. Epimanool is present in the sticky exudate on the leaf surfaces of C. viscosa.

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.

Studies of Australian Soft Corals. XLIII. The Structure Elucidation of a New Diterpene From Alcyonium molle

1989 ◽  
Vol 42 (5) ◽  
pp. 665 ◽  
Author(s):  
BF Bowden ◽  
JC Coll ◽  
MC Dai
Keyword(s):  
Absolute Configuration ◽  
High Field ◽  
Structure Elucidation ◽  
Kinetic Resolution ◽  
Soft Coral ◽  
Soft Corals ◽  
Resolution Method ◽  
The Absolute ◽  
First Time

The isolation of a new cladiellin based diterpene (6), (1S,2R,3S,4R,SR,6S,8E,11S,12R,13S,14S)-3-acetoxy-2,12-dibutanoyloxycladiell-8-ene-4,11-diol is reported from the soft coral Alcyonium molle (Octocorallia, Alcyonacea, Alcyoniidae). The structure was deduced by high-field n.m.r. spectroscopy including 13C-lH shift correlated 2D n.m.r. experiments and n.O.e. measurements. The absolute configuration was based on the kinetic resolution method of Horeau. This highly derivatized diterpene (6) is the first alcyonacean derived metabolite to possess hydroxy functionalities protected as butyrate esters, although this feature is relatively common among gorgonacean metabolites. Gorgosterol (7), which cooccurs with (6) in A. molle was identified and its 13C n.m.r. spectrum reported for the first time.

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