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Journal of Natural Products Dec 2023In our continuing efforts to describe the biological and chemical diversity of sponges from Kimbe Bay, Papua New Guinea, the known 30-norlanostane saponin sarasinoside C...
In our continuing efforts to describe the biological and chemical diversity of sponges from Kimbe Bay, Papua New Guinea, the known 30-norlanostane saponin sarasinoside C () was identified along with six new analogues named sarasinosides C, C, C, C, C, and C (-) from the sponge . The structures of the new compounds were elucidated by analysis of 1D and 2D NMR and HRMS data, as well as comparison with literature data. All new compounds are characterized by the same tetraose moiety, β-d-Xyl-(1→6)-β-d-GlcNAc-(1→2)-[β-d-GalNAc-(1→4)]-β-d-Xyl, as described previously for sarasinoside C, but differed in their aglycone moieties. When comparing NMR data of sarasinoside C with those of known analogues, a misassignment was identified in the configuration of the C-8/C-9 diol for the previously described sarasinoside R (), and it has been corrected here using a combination of ROESY analysis and molecular modeling.
Topics: Animals; Porifera; Saponins; Papua New Guinea; Molecular Structure
PubMed: 38032127
DOI: 10.1021/acs.jnatprod.3c01045 -
Molecules (Basel, Switzerland) Mar 2024Makaluvamine J, a pyrroloiminoquinone alkaloid of marine sponge origin, and its analogs were synthesized and assessed for their potential to develop as a novel and...
Makaluvamine J, a pyrroloiminoquinone alkaloid of marine sponge origin, and its analogs were synthesized and assessed for their potential to develop as a novel and selective growth inhibitor targeting human pancreatic cancer PANC-1 cells. Ts-damirone B, a common precursor featuring a pyrroloiminoquinone core structure, was synthesized through Bartoli indole synthesis and IBX-mediated oxidation. Late-stage diversification at -5 and -9 yielded makaluvamine J and several analogs. A structure-activity relationship (SAR) analysis highlighted the significance of the lipophilic side chain at -9 for the growth inhibitory activity of PANC-1 cells. The modest alkyl group at -5 was found to improve selectivity against other cancer cells. Among the prepared analogs, the tryptamine analog showed potent and selective cytotoxicity (IC = 0.029 µM, selective index = 13.1), exceeding those of natural products.
Topics: Animals; Humans; Pyrroloiminoquinones; Structure-Activity Relationship; Porifera; Antineoplastic Agents; Alkaloids
PubMed: 38543025
DOI: 10.3390/molecules29061389 -
Journal of Asian Natural Products... Nov 2023Two new alkaloids, spongimides A () and B (), along with five known ones (-), were isolated from the marine sponge sp. The structures of and were determined by the...
Two new alkaloids, spongimides A () and B (), along with five known ones (-), were isolated from the marine sponge sp. The structures of and were determined by the spectroscopic methods (UV, IR, MS, and NMR) and X-ray diffraction analysis. Compounds , , and were the first examples of 2,4-imidazolidinediones isolated from this genus. In addition, the cytotoxic and antibacterial activities of compounds and were also evaluated.
Topics: Animals; Molecular Structure; Porifera; Antineoplastic Agents; Alkaloids; Magnetic Resonance Spectroscopy
PubMed: 37042722
DOI: 10.1080/10286020.2023.2197227 -
Marine Biotechnology (New York, N.Y.) Dec 2023Sponges (Porifera) harbor a diversity of microorganisms that contribute largely to the production a vast array of bioactive compounds. The microorganisms associated with...
Sponges (Porifera) harbor a diversity of microorganisms that contribute largely to the production a vast array of bioactive compounds. The microorganisms associated with sponge have an important impact on the chemical diversity of the natural products. Herein, our study focuses on an Aaptos suberitoides commonly found in Indonesia. The objective of this study was to investigate the profile of prokaryotic community and the presence of aaptamine metabolites in sponge Aaptos suberitoides. Sponges were collected from two site locations (Liberty Wreck and Drop Off) in Tulamben, Bali. The sponges were identified by barcoding DNA cytochrome oxidase subunit I (COI) gene. The profile of prokaryotic composition was investigated by amplifying the 16S rRNA gene using primers 515f and 806r to target the V4 region. The metabolites were analyzed using LC-MS, and dereplication was done to identify the aaptamines and its derivates. The barcoding DNA of the sponges confirmed the identity of samples as Aaptos suberitoides. The prokaryotic communities of samples A. suberitoides were enriched and dominated by taxa Proteobacteria, Chloroflexi, Actinobacteria, and Acidobacteria. The chemical analysis showed that all sponges produce aaptamine and isoaaptamine except A. suberitoides S2421 produce analog of aaptamines. This is the first report on the profile of prokaryotic community and the aaptamine of tropical marine sponges, A. suberitoides, from Tulamben, Bali.
Topics: Animals; Porifera; Indonesia; RNA, Ribosomal, 16S; DNA
PubMed: 38008858
DOI: 10.1007/s10126-023-10268-7 -
Journal of Natural Products Nov 2023The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10/ mixture of trichotoxin A, was successfully achieved, commencing from...
The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10/ mixture of trichotoxin A, was successfully achieved, commencing from the natural monoterpenoid (-)-citronellal. Key steps in the synthesis involved introducing three alkenes and establishing a stereogenic secondary alcohol center. These transformations were accomplished through olefin cross-metathesis, Tebbe olefination, and enantioselective allylation using a chiral phosphoric acid. A comparison of the spectroscopic data between the synthetic dechlorotrichotoxin A and the reported spectra confirmed that the polyketide isolated from a species corresponds to trichotoxin A rather than dechlorotrichotoxin A.
Topics: Animals; Stereoisomerism; Alkenes; Polyketides; Ethanol; Porifera; Molecular Structure
PubMed: 37793019
DOI: 10.1021/acs.jnatprod.3c00629 -
Zootaxa Sep 2023The present study examines the taxonomy of sponge specimens with unique chemistry collectively known as Fascaplysinopsis reticulata (Hentschel, 1912). Examination of...
Revision of the genus Fascaplysinopsis, the type species Fascaplysinopsis reticulata (Hentschel, 1912) (Porifera, Dictyoceratida, Thorectidae) and descriptions of two new genera and seven new species.
The present study examines the taxonomy of sponge specimens with unique chemistry collectively known as Fascaplysinopsis reticulata (Hentschel, 1912). Examination of Hentschels original species upon which the genus Fascaplysinopsis Bergquist, 1980 was based in conjunction with a comparison with recent Indo-west Pacific collections, using morphological and molecular analyses (ITS and 28S rDNA), revealed extensive variation. Fascaplysinopsis reticulata was found to be a species complex comprising the genus Fascaplysinopsis, as well as two new genera: Skolosachlys gen. nov. and Rubrafasciculus gen. nov. The new species of Fascaplysinopsis described are F. palauensis sp. nov., F. klobos sp. nov. and F. ronquinni sp. nov. The new species of Skolosachlys gen. nov. described herein are: S. enlutea sp. nov. and S. nidus sp. nov. The new species described of Rubrafasciculus gen. nov. includes: R. cerasus sp. nov. and R. fijiensis sp. nov..
Topics: Animals; Phylogeny; DNA, Ribosomal; Porifera
PubMed: 38221341
DOI: 10.11646/zootaxa.5346.3.1 -
Cells Apr 2024Microtubules are an indispensable component of all eukaryotic cells due to their role in mitotic spindle formation, yet their organization and number can vary greatly in...
Microtubules are an indispensable component of all eukaryotic cells due to their role in mitotic spindle formation, yet their organization and number can vary greatly in the interphase. The last common ancestor of all eukaryotes already had microtubules and microtubule motor proteins moving along them. Sponges are traditionally regarded as the oldest animal phylum. Their body does not have a clear differentiation into tissues, but it contains several distinguishable cell types. The choanocytes stand out among them and are responsible for creating a flow of water with their flagella and increasing the filtering and feeding efficiency of the sponge. Choanocyte flagella contain microtubules, but thus far, observing a developed system of cytoplasmic microtubules in non-flagellated interphase sponge cells has been mostly unsuccessful. In this work, we combine transcriptomic analysis, immunofluorescence, and electron microscopy with time-lapse recording to demonstrate that microtubules appear in the cytoplasm of sponge cells only when transdifferentiation processes are activated. We conclude that dynamic cytoplasmic microtubules in the cells of sponges are not a persistent but rather a transient structure, associated with cellular plasticity.
Topics: Microtubules; Animals; Interphase; Cell Differentiation; Porifera
PubMed: 38727272
DOI: 10.3390/cells13090736 -
Marine Drugs Oct 2023Investigation of the Vietnamese marine sponge led to the isolation of two new polar isomalabaricanes: rhabdastrellosides A () and B (). Their structures and...
Investigation of the Vietnamese marine sponge led to the isolation of two new polar isomalabaricanes: rhabdastrellosides A () and B (). Their structures and stereochemistry were elucidated with the application of 1D and 2D NMR, HRESIMS, and HRESIMS/MS methods, as well as chemical modifications and GC-MS analysis. Metabolites and are the first isomalabaricanes with non-oxidized cyclopentane ring in the tricyclic core system. Moreover, having a 3-O-disaccharide moiety in their structures, they increase a very rare group of isomalabaricane glycosides. We report here a weak cytotoxicity of and toward human neuroblastoma SH-SY5Y cells and normal rat H9c2 cardiomyocytes, as well as the cytoprotective activity of rhabdastrelloside B () at 1 µM evaluated using CoCl-treated SH-SY5Y and H9c2 cells.
Topics: Animals; Humans; Rats; Molecular Structure; Glycosides; Drug Screening Assays, Antitumor; Triterpenes; Neuroblastoma; Porifera; Antineoplastic Agents
PubMed: 37999378
DOI: 10.3390/md21110554 -
Proceedings. Biological Sciences Aug 2023Sponges pump water to filter feed and for diffusive oxygen uptake. In doing so, trace DNA fragments from a multitude of organisms living around them are trapped in their...
Sponges pump water to filter feed and for diffusive oxygen uptake. In doing so, trace DNA fragments from a multitude of organisms living around them are trapped in their tissues. Here we show that the environmental DNA retrieved from archived marine sponge specimens can reconstruct the fish communities at the place of sampling and discriminate North Atlantic assemblages according to biogeographic region (from Western Greenland to Svalbard), depth habitat (80-1600 m), and even the level of protection in place. Given the cost associated with ocean biodiversity surveys, we argue that targeted and opportunistic sponge samples - as well as the specimens already stored in museums and other research collections - represent an invaluable trove of biodiversity information that can significantly extend the reach of ocean monitoring.
Topics: Animals; DNA; DNA, Environmental; Biodiversity; Fishes; Porifera
PubMed: 37644836
DOI: 10.1098/rspb.2023.0771 -
Journal of Morphology Sep 2023Reproduction is a key step for propagation of any species. Consequently, gametogenesis is crucial, as it links one generation to the other. Oogenesis is influenced by...
Reproduction is a key step for propagation of any species. Consequently, gametogenesis is crucial, as it links one generation to the other. Oogenesis is influenced by different factors, but it is usually related to the quality and quantity of the food and the capacity of the female to convert these resources into egg production. In Demospongiae (Porifera), oocytes vary in several aspects (e.g., origin, size, and vitellogenic pathways). However, data on oocyte morphology is still fragmentary, and the ultrastructural organization of reproductive cells has been investigated only in a few species, mainly of viviparous sponges. Here, we aimed to comprehend the oogenesis of two tropical oviparous demosponges (Cinachyrella apion and Tethya maza) using light and electron microscopy. In both species, oocytes seemed to originate from archaeocytes. Oocytes of C. apion were surrounded by a collagenous matrix and nurse cells containing many lipid vesicles. The increase of biosynthetic organelles, concomitantly with the presence of yolk vesicle in the ooplasm, indicated that the vitellogenesis was carried out through the mixed pathway. The oocytes of T. maza were surrounded by a follicle cell membrane and nurse cells containing yolk vesicles. The absence of characteristic biosynthetic organelles in the egg of this species indicated that vitellogenesis occured through the heterosynthetic pathway. The oogenesis of C. apion is similar to other species of the genus, while the follicle membrane and nurse cells surrounding the oocytes of T. maza are not observed in any other species of Tethya. These accessory cells were considered to have a trophic role during the oogenesis of the studied species. Moreover, the presence of these accessory cells may have ecological significance, as they accelerate the egg's production through trophic support of the growing oocyte.
Topics: Female; Animals; Oviparity; Oogenesis; Oocytes; Ovarian Follicle; Porifera
PubMed: 37585226
DOI: 10.1002/jmor.21625