ChemInform Abstract: MINOR AND TRACE STEROLS IN MARINE INVERTEBRATES. 26. ISOLATION AND STRUCTURE ELUCIDATION OF NINE NEW 5α,8α-EPIDOXY STEROLS FROM FOUR MARINE ORGANISMS

1982 ◽  
Vol 13 (6) ◽  
Author(s):  
A. A. L. GUNATILAKA ◽  
Y. GOPICHAND ◽  
F. J. SCHMITZ ◽  
C. DJERASSI
Keyword(s):  
Structure Elucidation ◽  
Marine Invertebrates ◽  
Marine Organisms

scholarly journals The Isolation and Structure Elucidation of Secondary Metabolites from Tongan Marine Invertebrates

2021 ◽  
Author(s):  
◽  
Victoria Helen Woolner
Keyword(s):  
Antifungal Activity ◽  
Secondary Metabolites ◽  
Structure Elucidation ◽  
Sea Cucumber ◽  
Marine Invertebrates ◽  
Marine Sponges ◽  
Marine Organisms ◽  
New Members ◽  
Ic50 Values ◽  
New Compounds

<p>During the course of this study, Tongan marine organisms were investigated for new secondary metabolites. A combination of reversed- and normal-phase chromatographic techniques and NMR spectroscopy was employed, to aid in the isolation and structure elucidation of the five known and four new compounds isolated in this study. A brief investigation into the antifungal activity of Tongan holothurian saponins was instigated in order to compare the activity against saponins isolated from the common New Zealand sea cucumber, Australostichopus mollis. A yeast-based chemical genetics study, determined the antifungal activity, for four partially purified Tongan holothurian extracts, against Saccharomyces cerevisiae, to be similar to neothyonidioside (44), a saponin from A. mollis. This result suggested the antifungal activity to be a common characteristic to sea cucumber saponins. Further interest in secondary metabolites from Tongan marine organisms led this study towards the investigation of Tongan marine sponges. Five sponges were selected for screening, and two chosen for further study which yielded five known compounds (51–53, 61, 62) and four new fascaplysin derivatives; 7-bromoreticulatine,10-bromo-6,7-dimethoxyhomofascaplysin C,10-bromo-6, 7-dimethoxyhomofascaplysin D, and 10-bromohomofascaplysin A (63–66, respectively). Although 63 and 66 are new members of the fascaplysin family solely due to the position of the bromine, it appears that bromination on the A-ring is comparatively rare, with only three of the 24 literature examples displaying A-ring bromination. On the other hand, 64 and 65 present a new sub-class of fascaplysin derivatives due to the presence of a dimethoxy functionality. Both 7-bromoreticulatine (63) and 10-bromohomofascaplysin A (66) were found to be potently cytotoxic in the HL-60 cell line, exhibiting IC50 values of 33.8 and 498 nM, respectively. 10-Bromo-6,7-dimethoxyhomofascaplysins C (64) and D (65) were significantly less cytotoxic with respective IC₅₀ values of 2.7 and 6.0 μΜ. (Abstract continues with diagrams).</p>

scholarly journals The Isolation and Structure Elucidation of Secondary Metabolites from Tongan Marine Invertebrates

2021 ◽  
Author(s):  
◽  
Victoria Helen Woolner
Keyword(s):  
Antifungal Activity ◽  
Secondary Metabolites ◽  
Structure Elucidation ◽  
Sea Cucumber ◽  
Marine Invertebrates ◽  
Marine Sponges ◽  
Marine Organisms ◽  
New Members ◽  
Ic50 Values ◽  
New Compounds

<p>During the course of this study, Tongan marine organisms were investigated for new secondary metabolites. A combination of reversed- and normal-phase chromatographic techniques and NMR spectroscopy was employed, to aid in the isolation and structure elucidation of the five known and four new compounds isolated in this study. A brief investigation into the antifungal activity of Tongan holothurian saponins was instigated in order to compare the activity against saponins isolated from the common New Zealand sea cucumber, Australostichopus mollis. A yeast-based chemical genetics study, determined the antifungal activity, for four partially purified Tongan holothurian extracts, against Saccharomyces cerevisiae, to be similar to neothyonidioside (44), a saponin from A. mollis. This result suggested the antifungal activity to be a common characteristic to sea cucumber saponins. Further interest in secondary metabolites from Tongan marine organisms led this study towards the investigation of Tongan marine sponges. Five sponges were selected for screening, and two chosen for further study which yielded five known compounds (51–53, 61, 62) and four new fascaplysin derivatives; 7-bromoreticulatine,10-bromo-6,7-dimethoxyhomofascaplysin C,10-bromo-6, 7-dimethoxyhomofascaplysin D, and 10-bromohomofascaplysin A (63–66, respectively). Although 63 and 66 are new members of the fascaplysin family solely due to the position of the bromine, it appears that bromination on the A-ring is comparatively rare, with only three of the 24 literature examples displaying A-ring bromination. On the other hand, 64 and 65 present a new sub-class of fascaplysin derivatives due to the presence of a dimethoxy functionality. Both 7-bromoreticulatine (63) and 10-bromohomofascaplysin A (66) were found to be potently cytotoxic in the HL-60 cell line, exhibiting IC50 values of 33.8 and 498 nM, respectively. 10-Bromo-6,7-dimethoxyhomofascaplysins C (64) and D (65) were significantly less cytotoxic with respective IC₅₀ values of 2.7 and 6.0 μΜ. (Abstract continues with diagrams).</p>

scholarly journals Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 330
Author(s):  
Timofey V. Malyarenko ◽  
Alla A. Kicha ◽  
Valentin A. Stonik ◽  
Natalia V. Ivanchina
Keyword(s):  
Marine Invertebrates ◽  
Biological Activities ◽  
Complete Information ◽  
Structural Features ◽  
Marine Organisms ◽  
Structural Components ◽  
Chemical Structures ◽  
The Past ◽  
Complex Lipids ◽  
Complex Sphingolipids

Sphingolipids are complex lipids widespread in nature as structural components of biomembranes. Commonly, the sphingolipids of marine organisms differ from those of terrestrial animals and plants. The gangliosides are the most complex sphingolipids characteristic of vertebrates that have been found in only the Echinodermata (echinoderms) phylum of invertebrates. Sphingolipids of the representatives of the Asteroidea and Holothuroidea classes are the most studied among all echinoderms. In this review, we have summarized the data on sphingolipids of these two classes of marine invertebrates over the past two decades. Recently established structures, properties, and peculiarities of biogenesis of ceramides, cerebrosides, and gangliosides from starfishes and holothurians are discussed. The purpose of this review is to provide the most complete information on the chemical structures, structural features, and biological activities of sphingolipids of the Asteroidea and Holothuroidea classes.

Structure elucidation of a main heptachloro congener of toxaphene in marine organisms after isolation from malipax®

Chemosphere ◽  
1996 ◽  
Vol 33 (6) ◽  
pp. 1005-1019 ◽  
Author(s):  
Bernd Krock ◽  
Walter Vetter ◽  
Bernd Luckas ◽  
Gerd Scherer
Keyword(s):  
Structure Elucidation ◽  
Marine Organisms

Mycosporine-like amino acids in 38 species of subtidal marine organisms from McMurdo Sound, Antarctica

1997 ◽  
Vol 9 (4) ◽  
pp. 392-398 ◽  
Author(s):  
J.B. McClintock ◽  
D. Karentz
Keyword(s):  
Amino Acids ◽  
Marine Invertebrates ◽  
Marine Organisms ◽  
Benthic Species ◽  
Mcmurdo Sound ◽  
Sterechinus Neumayeri ◽  
Low Concentrations ◽  
Low Levels ◽  
Qualitative Measurements ◽  
Iridaea Cordata

Mycosporine-like amino acids (MAAs) that absorb UV radiation (310–360 nm) were investigated in 34 species of benthic marine invertebrates (fourteen sponges, two cnidarians, one nemertean, four molluscs, one bryozoan, two arthropods, eight echinoderms and two tunicates), two species of benthic fish and two species of red algae collected during the spring of 1992 from McMurdo Sound. In addition, MAAs were measured in the ripe ovaries, testes and brooded juveniles of four species of echinoderms. While 90% of the species had MAAs in their tissues, both quantitative and qualitative measurements reflected a general lack of UV protectants among these fauna. Eight MAAs were detected among the species examined, but only four of these (mycosporine-glycine, shinorine, porphyra-334 and palythine) occurred in any appreciable number of the species. Palythinol only occurred in the sponge Isodictya erinacea and asterina-330 and palythene only occurred in the red alga Iridaea cordata. MAAs were detected in the ripe ovaries and testes of the sea urchin Sterechinus neumayeri and the ripe ovaries and brooded young of the sea cucumber Cucumaria ferrari. Low levels and abundances of MAAs may reflect a reduced need for UV protectants in marine organisms inhabiting subtidal (>20 m depth) benthic environments that experience seasonal sea-ice cover. Low concentrations of MAAs may also be a function of diet, since the majority of benthic species present in McMurdo Sound are not herbivorous.

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