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

10.26686/wgtn.16946008.v1 ◽

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

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.

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Three New Cytotoxic Withanolides from the Chinese Folk Medicine Physalis angulata

Natural Product Communications ◽

10.1177/1934578x1501001211 ◽

2015 ◽

Vol 10 (12) ◽

pp. 1934578X1501001 ◽

Cited By ~ 2

Author(s):

Cai-Yun Gao ◽

Ting Ma ◽

Jun Luo ◽

Ling-Yi Kong

Keyword(s):

Cell Line ◽

Folk Medicine ◽

2D Nmr ◽

Cytotoxic Activities ◽

Spectroscopic Techniques ◽

Aerial Parts ◽

Physalis Angulata ◽

The Absolute ◽

New Compounds

Physagulides M-O, three new withanolides (1–3), were isolated from the aerial parts of Physalis angulata L. Their structures were elucidated through extensive spectroscopic techniques, including 1D and 2D NMR, and HRESIMS. The absolute configurations (22- R) of these new compounds were determined by CD analysis. Compounds 1 and 3 showed significant selective cytotoxic activities on the MG-63 cell line, with IC50 values of 4.28 and 5.44 μM, respectively.

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Antifouling Sesterterpenes from the New Zealand Marine Sponge Semitaspongia Bactriana

Natural Product Communications ◽

10.1177/1934578x0900400306 ◽

2009 ◽

Vol 4 (3) ◽

pp. 1934578X0900400 ◽

Cited By ~ 2

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.

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

Australian Journal of Chemistry ◽

10.1071/c96120 ◽

1997 ◽

Vol 50 (4) ◽

pp. 341 ◽

Cited By ~ 13

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.

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Natural Products Analysis of South Pacific Marine Sponges

10.26686/wgtn.17151566.v1 ◽

2021 ◽

Author(s):

◽

Taitusi Taufa

Keyword(s):

Natural Products ◽

New Zealand ◽

Secondary Metabolites ◽

Optical Rotation ◽

Screening Method ◽

Marine Sponges ◽

Ic50 Value ◽

Products Analysis ◽

New Compounds ◽

Cacospongia Mycofijiensis

This thesis describes the isolation and structure elucidation of 15 new secondary metabolites from Tongan and New Zealand marine sponges. A total of 18 sponge specimens were subjected to an NMR-based screening method, of which four were analysed in detail. Examination of a two-sponge association, Stelletta crater and Desmacella dendyi from New Zealand, resulted in the isolation of two new 4-methylenesterols, craterols A (94) and B (95). To the best of the author’s knowledge, compounds 94 and 95 represent the first secondary metabolites to be reported from either species. Both 94 and 95 possess a double bond between C-5 and C-6, a feature that is unprecedented in this subgroup of marine natural products. An investigation of a Tongan sponge Zyzzya fuliginosa afforded two new pyrroloquinoline alkaloids, 6-bromodamirone B (182) and makaluvamine W (183). Makaluvamine W (183) contains an oxazole moiety, which is uncommon in this group of natural products. Both 182 and 183 lacked activity against the human promyelocytic leukemia cells (HL-60). Five new compounds were isolated from a Tongan sponge of the genus Leucetta, including two glycerol lipids (238 and 239), three glycerol ethers (244–246) and an imidazole alkaloid (243). Naamidine K (243) is a new addition to the naamidine family, while the glycerol metabolites are non-imidazole alkaloid additions to the group of compounds reported from this genus. A spectroscopic investigation into the Tongan sponge Cacospongia mycofijiensis yielded four new zampanolide analogues (282–285) and a new oxygenated sesquiterpene, isodictyodendrillin A (280). The isolation of the zampanolide analogues gives insight into the structure-activity relationship (SAR) in this family of compounds. Zampanolides B–D (282–284) displayed potent antiproliferative activity towards HL-60 cell lines in the low nanomolar range (3–5 nM), while zampanolide E (285) was significantly less potent with an IC50 value of 306 nM. In addition, the re-isolation of dactylolide (281) and zampanolide A (278) from this sponge, established a firm conclusion regarding the controversial configuration of dactylolide (281), which possesses the same absolute configuration as (–)-zampanolide A (278) and has a levorotatory optical rotation.

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

10.26686/wgtn.17067593 ◽

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

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.

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

Australian Journal of Chemistry ◽

10.1071/ch9930623 ◽

1993 ◽

Vol 46 (5) ◽

pp. 623 ◽

Cited By ~ 24

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.

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

ChemInform ◽

10.1002/chin.201521227 ◽

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

10.26686/wgtn.17067593.v1 ◽

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

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.

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