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.

Chemistry of the shellfish toxin domoic acid: characterization of related compounds

1994 ◽  
Vol 72 (2) ◽  
pp. 430-436 ◽  
Author(s):  
John A. Walter ◽  
Michael Falk ◽  
Jeffrey L.C. Wright
Keyword(s):  
Molecular Modelling ◽  
Domoic Acid ◽  
Conformational Flexibility ◽  
Spectroscopic Methods ◽  
Clear Cut ◽  
Nmr Data ◽  
Shellfish Toxin ◽  
New Compounds ◽  
Related Compounds

Five new compounds related to the neurotoxin domoic acid have been characterized by spectroscopic methods. They include a diastereoisomer that occurs naturally with domoic acid in mussels and four hydrogenation products. The stereochemistry of the two epimeric tetrahydro derivatives could not be assigned on the basis of the NMR data alone because of high conformational flexibility. However, a clear-cut assignment was possible by molecular modelling in combination with the NMR data.

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>

The Constituents of Marine Sponges. VI. Diterpenoid Metabolites of the New Zealand Sponge Chelonaplysilla violacea

1993 ◽  
Vol 46 (5) ◽  
pp. 623 ◽  
Author(s):  
PR Bergquist ◽  
BF Bowden ◽  
RC Cambie ◽  
PA Craw ◽  
P Karuso ◽  
...  
Keyword(s):  
New Zealand ◽  
Coastal Waters ◽  
Marine Sponges ◽  
Spectroscopic Methods ◽  
New Compounds

The sponge Chelonaplysilla violacea, collected from New Zealand coastal waters, contains as major constituents the diterpenoids aplyviolene (1a), norrisolide (2), dendrillolide A (3) aplyroseol-7 (4), spongian-16-one (5), chelonaplysin C (6), and a series of new compounds cheloviolene A-F and cheloviolin. Structures were assigned to cheloviolene A (7), [3aR-[3aα,4α(1R*,3aR*,8aS*),5β,6aα]]-5-hydroxy-4(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydrofuro [2,3- b] furan-2(3H)-one, cheloviolene B (8), [3aR-[3aα,4a(1R*,3aR*, 8aS*),5α,6aα]]-5-hydroxy-4-(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydrofuro [2,3-b]furan-2(3H)-one, cheloviolene C (9), [1'ξ(1R*,3aS*,7aS*),4ξ]-4-[1′-( acetyloxymethyl )-2′-(4,4,7a-trimethyloctahydro-1H-inden-1-yl)prop-2′-enyl] dihydrofuran -2(3H)-one, cheloviolene D (10), methyl [3α,4α(1R*,3aR*,8aS*)]-5-oxo-4-(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl)tetrahydrofuran-3-acetate, cheloviolene E (11), methyl [3α,4α-(1R*,3aS*,7aS*)]-5-oxo-4-[1′-(4,4,7a-trimethyloctahydro-1H-inden-1-yl) ethenyl ]tetrahydrofuran-3-acetate, and cheloviolene F (12), [4ξ,5ξ(1R*,3R*,8aS*)]-4-( acetyloxymethyl )-5-(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydro-2H-pyran-2-one, by using spectroscopic methods; the structure (13) was deduced for cheloviolin, [1S-[1α,5α,6α,8R*(1aS*,3aS*,7aS*,7b-R*)]]-6-acetyloxy-8-(4,4,7a-trimethyldecahydrocylopropa[a] naphthalen-la-yl )-2,7-dioxabicyclo- [3.2.1]octan-3-one.

scholarly journals New Nitrogenous Spongian Diterpenes from the New Zealand Marine Sponge Darwinella Oxeata

2021 ◽  
Author(s):  
◽  
Katie Orlagh Dowle
Keyword(s):  
New Zealand ◽  
Amino Acid ◽  
Cell Line ◽  
Marine Sponge ◽  
Detailed Examination ◽  
Marine Sponges ◽  
Side Chain ◽  
Spectroscopic Techniques ◽  
New Compounds ◽  
Mtt Assays

<p>During the course of this research five New Zealand marine sponges were investigated. Detailed examination of one of the species, Darwinella oxeata, has resulted in the isolation of ten compounds whose structures were elucidated using a variety of spectroscopic techniques and a simple derivatisation reaction. These compounds were identified as rearranged spongian diterpenes with the aplysulphurane backbone. Five of these compounds have been previously reported, though two of them were originally isolated from another marine sponge, Dendrilla membranosa. The five new compounds, oxeatamides C to G (25-29), were found to have the same diterpene portion as the oxeatamides already isolated from this sponge. They do, however, differ in the gamma-lactam side chain, which is proposed to be of amino acid origin. The new oxeatamides showed moderate levels of cytotoxicity against the HL-60 cell line in MTT assays.</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>

Two New Clerodane Diterpenes from the New Zealand Marine Sponge Raspailia sp.

1998 ◽  
Vol 51 (12) ◽  
pp. 1097 ◽  
Author(s):  
Lyndon M. West ◽  
Peter T. Northcote ◽  
Chris N. Battershill
Keyword(s):  
New Zealand ◽  
Marine Sponge ◽  
Spectroscopic Methods ◽  
The South ◽  
Clerodane Diterpenes

Two new cis-ring fused clerodane diterpenes, raspailenone (1) and raspailol (2), have been isolated from a Raspailia species collected from subtidal waters of the South Island of New Zealand. The structures of the two compounds have been established by spectroscopic methods.

scholarly journals New Nitrogenous Spongian Diterpenes from the New Zealand Marine Sponge Darwinella Oxeata

2021 ◽  
Author(s):  
◽  
Katie Orlagh Dowle
Keyword(s):  
New Zealand ◽  
Amino Acid ◽  
Cell Line ◽  
Marine Sponge ◽  
Detailed Examination ◽  
Marine Sponges ◽  
Side Chain ◽  
Spectroscopic Techniques ◽  
New Compounds ◽  
Mtt Assays

<p>During the course of this research five New Zealand marine sponges were investigated. Detailed examination of one of the species, Darwinella oxeata, has resulted in the isolation of ten compounds whose structures were elucidated using a variety of spectroscopic techniques and a simple derivatisation reaction. These compounds were identified as rearranged spongian diterpenes with the aplysulphurane backbone. Five of these compounds have been previously reported, though two of them were originally isolated from another marine sponge, Dendrilla membranosa. The five new compounds, oxeatamides C to G (25-29), were found to have the same diterpene portion as the oxeatamides already isolated from this sponge. They do, however, differ in the gamma-lactam side chain, which is proposed to be of amino acid origin. The new oxeatamides showed moderate levels of cytotoxicity against the HL-60 cell line in MTT assays.</p>

scholarly journals New Aromatic Bisabolane Derivatives with Lipid-Reducing Activity from the Marine Sponge Myrmekioderma sp.

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 375 ◽  
Author(s):  
Margarida Costa ◽  
Laura Coello ◽  
Ralph Urbatzka ◽  
Marta Pérez ◽  
Margret Thorsteinsdottir
Keyword(s):  
Spectral Analysis ◽  
Spectral Data ◽  
Marine Sponge ◽  
Metabolic Disorders ◽  
Fat Metabolism ◽  
Nile Red ◽  
2D Nmr ◽  
Reducing Activity ◽  
New Compounds ◽  
Related Compounds

The previously reported 1-(2,4-dihydroxy-5-methylphenyl)ethan-1-one (1), (1’Z)-2-(1’,5’-dimethylhexa-1’,4’-dieny1)-5-methylbenzene-1,4-diol (2), and 1,8-epoxy-1(6),2,4,7,10-bisaborapentaen-4-ol (5) together with four new structures of aromatic bisabolane-related compounds (3, 4, 6, 7) were isolated from the marine sponge Myrmekioderma sp. Compounds 1, 2, and 5 were identified based on spectral data available in the literature. The structures of the four new compounds were experimentally established by 1D and 2D-NMR and (−)-HRESIMS spectral analysis. Cytotoxic and lipid-reducing activities of the isolated compounds were evaluated. None of the isolated compounds were active against the tested cancer cell lines; however, lipid-reducing activity was found for compounds 2–5 and 7 in the zebrafish Nile red fat metabolism assay. This class of compounds should be further explored for their suitability as possible agents for the treatment of lipid metabolic disorders and obesity.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

Sign in / Sign up

Export Citation Format

Share Document