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.

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.

scholarly journals Natural Products Analysis  of South Pacific Marine  Sponges

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

<p>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.</p>

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 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 Natural Products Analysis  of South Pacific Marine  Sponges

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

<p>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.</p>

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.

scholarly journals A new species of sea urchin associating clingfish of the genus Dellichthys from New Zealand (Teleostei, Gobiesocidae)

ZooKeys ◽  
2018 ◽  
Vol 740 ◽  
pp. 77-95 ◽  
Author(s):  
Kevin W. Conway ◽  
Andrew L. Stewart ◽  
Adam P. Summers
Keyword(s):  
New Species ◽  
New Zealand ◽  
Sexual Dimorphism ◽  
Sea Urchin ◽  
Coastal Waters ◽  
Sensory System ◽  
A New Species ◽  
Shallow Coastal Waters

A new species of clingfish, Dellichthystrnskii sp. n. is described on the basis of 27 specimens, 11.9–46.0 mm SL, collected from intertidal and shallow coastal waters of New Zealand. It is distinguished from its only congener, D.morelandi Briggs, 1955 by characters of the cephalic sensory system and oral jaws, snout shape, and colouration in life. A rediagnosis is provided for D.morelandi, which is shown to exhibit sexual dimorphism in snout shape.

scholarly journals Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3186 ◽  
Author(s):  
Vasilyev ◽  
Bizyaev ◽  
Komarov ◽  
Gatilov ◽  
Tkachev
Keyword(s):  
Calculated Data ◽  
Transition Metal Ions ◽  
Synthetic Approach ◽  
Spectroscopic Methods ◽  
Aromatic Diamines ◽  
X Ray ◽  
X Ray Crystallography ◽  
Chemical Structures ◽  
Polydentate Ligands ◽  
New Compounds

A synthetic approach to a new group of stable chiral C2-symmetric diimines with the 4,5-diazafluorene core has been developed based on condensation of dipinodiazafluorene with aromatic diamines. The chemical structures of new compounds were proven by spectroscopic methods and X-ray crystallography. All the compounds form solvates with organic solvents (chloroform, benzene, 1,4-dioxane) and water. Specific spectral data of the new compounds are explained using calculated data (DFT). Diimines of the pinodiazafluorene series give colored reactions with transition metal ions and can be regarded as prospective polydentate ligands with interesting luminescent and chiroptical properties.

scholarly journals Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1440
Author(s):  
Alla A. Kicha ◽  
Dinh T. Ha ◽  
Timofey V. Malyarenko ◽  
Anatoly I. Kalinovsky ◽  
Roman S. Popov ◽  
...  
Keyword(s):  
Coastal Waters ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Effects ◽  
One Dimensional ◽  
The Common ◽  
Polyhydroxylated Steroids ◽  
New Compounds ◽  
Ht 29 ◽  
Inhibit Cell Proliferation

Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

scholarly journals Bioactive Molecules from Mangrove Streptomyces qinglanensis 172205

Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 255
Author(s):  
Dongbo Xu ◽  
Erli Tian ◽  
Fandong Kong ◽  
Kui Hong
Keyword(s):  
Gene Cluster ◽  
Secondary Metabolite ◽  
Biosynthetic Gene Cluster ◽  
Bioactive Molecules ◽  
Spectroscopic Methods ◽  
Biosynthetic Gene ◽  
Electronic Circular Dichroism ◽  
Chemical Structures ◽  
New Compounds ◽  
Antiproliferative Activities

Five new compounds 15R-17,18-dehydroxantholipin (1), (3E,5E,7E)-3-methyldeca-3,5,7-triene-2,9-dione (2) and qinlactone A–C (3–5) were identified from mangrove Streptomyces qinglanensis 172205 with “genetic dereplication,” which deleted the highly expressed secondary metabolite-enterocin biosynthetic gene cluster. The chemical structures were established by spectroscopic methods, and the absolute configurations were determined by electronic circular dichroism (ECD). Compound 1 exhibited strong anti-microbial and antiproliferative bioactivities, while compounds 2–4 showed weak antiproliferative activities.

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