Chemistry of the mycalamides: antiviral and antitumour compounds from a New Zealand marine sponge. Part 6.1–3 The synthesis and testing of analogues of the C(7)–C(10) fragment

1997 ◽  
pp. 1647-1654 ◽  
Author(s):  
Andrew D. Abell ◽  
John W. Blunt ◽  
Glenn J. Foulds ◽  
Murray H. G. Munro
Keyword(s):  
New Zealand ◽  
Marine Sponge

Hamigerans R and S: Nitrogenous Diterpenoids from the New Zealand Marine Sponge Hamigera tarangaensis

2018 ◽  
Vol 81 (2) ◽  
pp. 387-393 ◽  
Author(s):  
Ethan F. Woolly ◽  
A. Jonathan Singh ◽  
Euan R. Russell ◽  
John H. Miller ◽  
Peter T. Northcote
Keyword(s):  
New Zealand ◽  
Marine Sponge

Structurally diverse hamigerans from the New Zealand marine sponge Hamigera tarangaensis: NMR-directed isolation, structure elucidation and antifungal activity

2013 ◽  
Vol 11 (46) ◽  
pp. 8041 ◽  
Author(s):  
A. Jonathan Singh ◽  
Jonathan D. Dattelbaum ◽  
Jessica J. Field ◽  
Zlatka Smart ◽  
Ethan F. Woolly ◽  
...  
Keyword(s):  
New Zealand ◽  
Antifungal Activity ◽  
Marine Sponge ◽  
Structure Elucidation

scholarly journals Antifouling Sesterterpenes from the New Zealand Marine Sponge Semitaspongia Bactriana

2009 ◽  
Vol 4 (3) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Michael Stewart ◽  
Craig Depree ◽  
Karen J Thompson
Keyword(s):  
New Zealand ◽  
Marine Sponge ◽  
Relative Stability ◽  
Spectroscopic Techniques ◽  
Bugula Neritina ◽  
Synthetic Analogues ◽  
Test Species ◽  
Nitzschia Closterium

Three antifouling (AF) sesterterpenes have been isolated from the New Zealand marine sponge Semitaspongia bactriana with toxicity against the diatom Nitzschia closterium and bryozoan Bugula neritina. The three metabolites have been characterised by spectroscopic techniques as 7 E, 12 E, 20 Z-variabilin (1), cavernosolide (2) and lintenolide A (3) (also called spongianolide C) and have low micromolar activity against our two test species. The γ-hydroxybutenolide containing sesterterpenes (2 and 3) show the most promise, with relative stability and suitable lipophilicity for incorporation of either these metabolites, or synthetic analogues, as biocides to produce paints or plastics with AF properties.

Avarol and Related Compounds from the New Zealand Marine Sponge Dysidea sp.

1997 ◽  
Vol 50 (4) ◽  
pp. 341 ◽  
Author(s):  
Michael Stewart ◽  
Patrick M. Fell ◽  
John W. Blunt ◽  
Murray H. G. Munro
Keyword(s):  
New Zealand ◽  
Marine Sponge ◽  
Spectroscopic Methods ◽  
New Compounds ◽  
Related Compounds

Bioassay and t.l.c. guided separation of extracts from the New Zealand marine sponge Dysidea sp. has led to the isolation of avarol (1), six other known compounds (2)–(4) and (6)–(8), and seven new compounds (9)–(15). All but one of these, compound (8), are related to avarol. The structures of all the compounds have been established by spectroscopic methods.

ChemInform Abstract: Structurally Diverse Hamigerans from the New Zealand Marine Sponge Hamigera tarangaensis: NMR-Directed Isolation, Structure Elucidation and Antifungal Activity.

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
A. Jonathan Singh ◽  
Jonathan D. Dattelbaum ◽  
Jessica J. Field ◽  
Zlatka Smart ◽  
Ethan F. Woolly ◽  
...  
Keyword(s):  
New Zealand ◽  
Antifungal Activity ◽  
Marine Sponge ◽  
Structure Elucidation

scholarly journals Isolation and Structural Elucidation of Secondary Metabolites from New Zealand Marine Sponge Aaptos confertus

2021 ◽  
Author(s):  
◽  
Charlotte Page
Keyword(s):  
New Zealand ◽  
Secondary Metabolites ◽  
Marine Sponge ◽  
Marine Organism ◽  
Structural Elucidation ◽  
Ether Linkage ◽  
Diverse Range ◽  
Lipid Biomarker ◽  
Branched Chain ◽  
New Compounds

<p>This study reports on the spectroscopy-guided isolation and structural elucidation of secondary metabolites from the New Zealand marine sponge Aaptos confertus. An extraction of the sponge material, followed by several purification steps, led to the isolation of potential new compounds CJP02 20A, CJP02 20C and CJP02 04CB, a known 2,5-diketopiperzine cyclo(L-Phe-L-Pro), and a previously reported 3-((13-methylhexadecyl)oxy)propane-1,2-diol. Corrections to the ¹H NMR data reported for 3-((13-methylhexadecyl)oxy)propane-1,2-diol were also recorded.  The relationship between the oceanic climate where a marine organism habituates and its production of secondary metabolites is discussed. The isolation of a diverse range of compounds, either novel or new to the genus, suggests that organisms originating in temperate climates are similar in value to those from tropical climates, where higher rates of predation (and therefore, selective pressure) are thought to produce superior diversity in their secondary metabolic distribution. In addition to the new compounds isolated, the diketopiperazine described is the first reported molecule of that class from the genus Aaptos.  The significance of the isolated compounds is discussed, in the context of drug discovery and development. The potential of the branched-chain mono-glycerol ether 3-((13-methylhexadecyl)oxy)propane-1,2-diol as a lipid biomarker for the genus Aaptos was examined, as this compound has only been reported from species of that genera. In addition, it’s potential as an immunomodulatory drug is discussed, including the significance of the ether linkage in contrast to the more common ester linkage. The isolation of the 2,5-diketopiperazine cyclo(L-Phe-L-Pro) new to the genus was shown to support the potential in diversity of climate and geographical distribution. This class of molecule is generated through the shikimate biosynthetic pathway; a metabolic route used by bacteria, fungi and algae. A proposed symbiotic relationship between the sponge Aaptos confertus and a proximal bacteria, fungi or algae exemplifies the value of New Zealand’s diverse and unique marine organisms.</p>

scholarly journals Isolation and Structural Elucidation of Secondary Metabolites from New Zealand Marine Sponge Aaptos confertus

2021 ◽  
Author(s):  
◽  
Charlotte Page
Keyword(s):  
New Zealand ◽  
Secondary Metabolites ◽  
Marine Sponge ◽  
Marine Organism ◽  
Structural Elucidation ◽  
Ether Linkage ◽  
Diverse Range ◽  
Lipid Biomarker ◽  
Branched Chain ◽  
New Compounds

<p>This study reports on the spectroscopy-guided isolation and structural elucidation of secondary metabolites from the New Zealand marine sponge Aaptos confertus. An extraction of the sponge material, followed by several purification steps, led to the isolation of potential new compounds CJP02 20A, CJP02 20C and CJP02 04CB, a known 2,5-diketopiperzine cyclo(L-Phe-L-Pro), and a previously reported 3-((13-methylhexadecyl)oxy)propane-1,2-diol. Corrections to the ¹H NMR data reported for 3-((13-methylhexadecyl)oxy)propane-1,2-diol were also recorded.  The relationship between the oceanic climate where a marine organism habituates and its production of secondary metabolites is discussed. The isolation of a diverse range of compounds, either novel or new to the genus, suggests that organisms originating in temperate climates are similar in value to those from tropical climates, where higher rates of predation (and therefore, selective pressure) are thought to produce superior diversity in their secondary metabolic distribution. In addition to the new compounds isolated, the diketopiperazine described is the first reported molecule of that class from the genus Aaptos.  The significance of the isolated compounds is discussed, in the context of drug discovery and development. The potential of the branched-chain mono-glycerol ether 3-((13-methylhexadecyl)oxy)propane-1,2-diol as a lipid biomarker for the genus Aaptos was examined, as this compound has only been reported from species of that genera. In addition, it’s potential as an immunomodulatory drug is discussed, including the significance of the ether linkage in contrast to the more common ester linkage. The isolation of the 2,5-diketopiperazine cyclo(L-Phe-L-Pro) new to the genus was shown to support the potential in diversity of climate and geographical distribution. This class of molecule is generated through the shikimate biosynthetic pathway; a metabolic route used by bacteria, fungi and algae. A proposed symbiotic relationship between the sponge Aaptos confertus and a proximal bacteria, fungi or algae exemplifies the value of New Zealand’s diverse and unique marine organisms.</p>

ChemInform Abstract: The Nitrogenous Hamigerans: Unusual Amino Acid-Derivatized Aromatic Diterpenoid Metabolites from the New Zealand Marine Sponge Hamigera tarangaensis.

ChemInform ◽  
2015 ◽  
Vol 46 (21) ◽  
pp. no-no
Author(s):  
Jonathan D. Dattelbaum ◽  
A. Jonathan Singh ◽  
Jessica J. Field ◽  
John H. Miller ◽  
Peter T. Northcote
Keyword(s):  
New Zealand ◽  
Amino Acid ◽  
Marine Sponge ◽  
Unusual Amino Acid
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