scholarly journals Isolation of Smenopyrone, a Bis-γ-Pyrone Polypropionate from the Caribbean Sponge Smenospongia aurea

Marine Drugs ◽  
2018 ◽  
Vol 16 (8) ◽  
pp. 285 ◽  
Author(s):  
Germana Esposito ◽  
Roberta Teta ◽  
Gerardo Della Sala ◽  
Joseph Pawlik ◽  
Alfonso Mangoni ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Chemical Communication ◽  
Spectroscopic Analysis ◽  
Marine Sponges ◽  
Symbiotic Bacteria ◽  
Model Compounds ◽  
Organic Extract ◽  
Bacterial Signaling ◽  
The Caribbean ◽  
Absolute Stereochemistry

The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route such as the smenamides. In this paper, we report the presence of a biogenetically different compound known as smenopyrone, which is a polypropionate containing two γ-pyrone rings. The structure of smenopyrone including its relative and absolute stereochemistry was determined by spectroscopic analysis (NMR, MS, ECD) and supported by a comparison with model compounds from research studies. Pyrone polypropionates are unprecedented in marine sponges but are commonly found in marine mollusks where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. Since pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.

scholarly journals Isolation of Smenopyrone, a Bis-g-Pyrone Polypropionate from the Caribbean Sponge Smenospongia Aurea.

2018 ◽  
Author(s):  
Germana Esposito ◽  
Roberta Teta ◽  
Gerardo Della Sala ◽  
Joseph R. Pawlik ◽  
Alfonso Mangoni ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Chemical Communication ◽  
Spectroscopic Analysis ◽  
Marine Sponges ◽  
Symbiotic Bacteria ◽  
Model Compounds ◽  
Organic Extract ◽  
Bacterial Signaling ◽  
The Caribbean ◽  
Absolute Stereochemistry

The organic extract of the Caribbean sponge Smenospongia aurea has been shown to contain an array of novel chlorinated secondary metabolites derived from a mixed PKS-NRPS biogenetic route, such as the smenamides. Here we report the presence of a biogenetically different compound, smenopyrone (1), a polypropionate containing two -pyrone rings. The structure of smenopyrone, including its relative and absolute stereochemistry, was determined by spectroscopic analysis (NMR, MS, ECD) supported by comparison with model compounds from the literature. Pyrone polypropionates are unprecedented in marine sponges, but are commonly found in marine mollusks, where their biosynthesis by symbiotic bacteria has been hypothesized and at least in one case demonstrated. As pyrones have recently been recognized as bacterial signaling molecules, we speculate that smenopyrone could mediate inter-kingdom chemical communication between S. aurea and its symbiotic bacteria.

scholarly journals Natural Products in Polyclad Flatworms

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 47
Author(s):  
Justin M. McNab ◽  
Jorge Rodríguez ◽  
Peter Karuso ◽  
Jane E. Williamson
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Marine Invertebrates ◽  
Symbiotic Bacteria ◽  
Chemical Defences ◽  
Number Of Species ◽  
Bioactive Secondary Metabolites ◽  
Potential Sources ◽  
Polyclad Flatworms

Marine invertebrates are promising sources of novel bioactive secondary metabolites, and organisms like sponges, ascidians and nudibranchs are characterised by possessing potent defensive chemicals. Animals that possess chemical defences often advertise this fact with aposematic colouration that potential predators learn to avoid. One seemingly defenceless group that can present bright colouration patterns are flatworms of the order Polycladida. Although members of this group have typically been overlooked due to their solitary and benthic nature, recent studies have isolated the neurotoxin tetrodotoxin from these mesopredators. This review considers the potential of polyclads as potential sources of natural products and reviews what is known of the activity of the molecules found in these animals. Considering the ecology and diversity of polyclads, only a small number of species from both suborders of Polycladida, Acotylea and Cotylea have been investigated for natural products. As such, confirming assumptions as to which species are in any sense toxic or if the compounds they use are biosynthesised, accumulated from food or the product of symbiotic bacteria is difficult. However, further research into the group is suggested as these animals often display aposematic colouration and are known to prey on invertebrates rich in bioactive secondary metabolites.

scholarly journals Two New Piperazine-Triones from a Marine-Derived Streptomycetes sp. Strain SMS636

Marine Drugs ◽  
2019 ◽  
Vol 17 (3) ◽  
pp. 186 ◽  
Author(s):  
Xiuli Xu ◽  
Jiahui Han ◽  
Rui Lin ◽  
Steven Polyak ◽  
Fuhang Song
Keyword(s):  
Staphylococcus Aureus ◽  
Minimum Inhibitory Concentration ◽  
Secondary Metabolites ◽  
Deep Sea ◽  
Spectroscopic Analysis ◽  
Inhibitory Concentration ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Bacillus Calmette Guerin ◽  
Methicillin Resistant

Two new piperazine-triones lansai E and F (1, 2), together with four known secondary metabolites lansai D (3), 1-N-methyl-(E,Z)-albonoursin (4), imidazo[4,5-e]-1,2,4-triazine (5), and streptonigrin (6) were isolated from a deep-sea-derived Streptomycetes sp. strain SMS636. The structures of the isolated compounds were confirmed by comprehensive spectroscopic analysis, including HRESIMS, 1D and 2D NMR. Compound 4 exhibited moderate antibacterial activities against Staphylococcus aureus and methicillin resistant S. aureus (MRSA) with Minimum Inhibitory Concentration (MIC) values of 12.5 and 25 μg/mL, respectively. Compound 6 displayed significant antibacterial activities against S. aureus, MRSA and Bacillus Calmette-Guérin (BCG) with MIC values of 0.78, 0.78 and 1.25 μg/mL, respectively.

scholarly journals Pubinernoid A and Apo-9′-fucoxanthinone, Secondary Metabolites from a Gorgonian Coral Pinnigorgia sp

2016 ◽  
Vol 11 (6) ◽  
pp. 1934578X1601100
Author(s):  
Hsin-Huan Chang ◽  
Yu-Chia Chang ◽  
Wu-Fu Chen ◽  
Tsong-Long Hwang ◽  
Lee-Shing Fang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Spectroscopic Data ◽  
Spectroscopic Analysis ◽  
Inhibitory Effect ◽  
Human Neutrophils ◽  
Gorgonian Coral ◽  
First Report ◽  
Significant Inhibitory Effect ◽  
Animal Source

The structures of pubinernoid A (1) and apo-9′-fucoxanthinone (2), isolated from a gorgonian coral Pinnigorgia sp., were elucidated on the basis of spectroscopic analysis and by comparison of their spectroscopic data with those of known compounds. This is the first report of 1 and 2 from an animal source. Apo-9′-fucoxanthinone (2) displayed a significant inhibitory effect on the release of elastase by human neutrophils, with an IC50 value of 5.75 μM.

Fungi from marine sponges: diversity, biological activity and secondary metabolites

2000 ◽  
Vol 104 (11) ◽  
pp. 1354-1365 ◽  
Author(s):  
Ulrich Höller ◽  
Anthony D. Wright ◽  
Gesa F. Matthee ◽  
Gabrielle M. Konig ◽  
Siegfried Draeger ◽  
...  
Keyword(s):  
Biological Activity ◽  
Secondary Metabolites ◽  
Marine Sponges

Trachycladindoles H–M: Molecular Networking Guided Exploration of a Library of Southern Australian Marine Sponges

2020 ◽  
Vol 73 (4) ◽  
pp. 338 ◽  
Author(s):  
Shamsunnahar Khushi ◽  
Laizuman Nahar ◽  
Angela A. Salim ◽  
Robert J. Capon
Keyword(s):  
Chemical Analysis ◽  
Natural Product ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Marine Sponges ◽  
Single Specimen ◽  
Guided Search ◽  
Guided Exploration ◽  
Rare Class ◽  
Great Australian Bight

A global natural product social (GNPS) molecular network guided search of a library of 960 southern Australian marine sponge extracts successfully detected a deep-water Great Australian Bight sponge, Geodia sp. (CMB-01063), as a new source of a rare class of indolo-imidazole alkaloids previously believed to be unique to a single specimen of Trachycladus laevispirulifer (CMB-03397). Chemical analysis of CMB-01063 detected the known trachycladindoles A–G (1–7), and led to the isolation, characterisation, and structure elucidation of the new trachycladindoles H–M (8–13). Structures for 8–13 were assigned on the basis of detailed spectroscopic analysis, with comparison to authentic standards of 1–7.

scholarly journals Fast Detection of Two Smenamide Family Members Using Molecular Networking

Marine Drugs ◽  
2019 ◽  
Vol 17 (11) ◽  
pp. 618 ◽  
Author(s):  
Alessia Caso ◽  
Germana Esposito ◽  
Gerardo Della Sala ◽  
Joseph R. Pawlik ◽  
Roberta Teta ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Cell Lines ◽  
Absolute Configuration ◽  
Antiproliferative Activity ◽  
Spectroscopic Analysis ◽  
Alkyl Chain ◽  
Molecular Networking ◽  
New Members ◽  
Fast Detection ◽  
Mcf 7

Caribbean sponges of the genus Smenospongia are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of S. aurea two new members of the smenamide family, namely smenamide F (1) and G (2). The structure of smenamide F (1) and G (2) was determined by spectroscopic analysis (NMR, MS, ECD). The relative and the absolute configuration at C-13, C-15, and C-16 was determined on the basis of the conformational rigidity of a 1,3-disubstituted alkyl chain system (i.e., the C-12/C-18 segment of compound (1). Smenamide F (1) and G (2) were shown to exert a selective moderate antiproliferative activity against cancer cell lines MCF-7 and MDA-MB-231, while being inactive against MG-63.

scholarly journals Microorganisms Associated with the Marine Sponge Scopalina hapalia: A Reservoir of Bioactive Molecules to Slow Down the Aging Process

2020 ◽  
Vol 8 (9) ◽  
pp. 1262
Author(s):  
Charifat Said Hassane ◽  
Mireille Fouillaud ◽  
Géraldine Le Goff ◽  
Aimilia D. Sklirou ◽  
Jean Bernard Boyer ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Marine Sponge ◽  
Marine Sponges ◽  
Sirtuin 1 ◽  
Bioactive Molecules ◽  
Aging Research ◽  
Fyn Kinase ◽  
The Indian Ocean ◽  
Metabolites Production ◽  
Future Work

Aging research aims at developing interventions that delay normal aging processes and some related pathologies. Recently, many compounds and extracts from natural products have been shown to delay aging and/or extend lifespan. Marine sponges and their associated microorganisms have been found to produce a wide variety of bioactive secondary metabolites; however, those from the Southwest of the Indian Ocean are much less studied, especially regarding anti-aging activities. In this study, the microbial diversity of the marine sponge Scopalina hapalia was investigated by metagenomic analysis. Twenty-six bacterial and two archaeal phyla were recovered from the sponge, of which the Proteobacteria phylum was the most abundant. In addition, thirty isolates from S. hapalia were selected and cultivated for identification and secondary metabolites production. The selected isolates were affiliated to the genera Bacillus, Micromonospora, Rhodoccocus, Salinispora, Aspergillus, Chaetomium, Nigrospora and unidentified genera related to the family Thermoactinomycetaceae. Crude extracts from selected microbial cultures were found to be active against seven targets i.e., elastase, tyrosinase, catalase, sirtuin 1, Cyclin-dependent kinase 7 (CDK7), Fyn kinase and proteasome. These results highlight the potential of microorganisms associated with a marine sponge from Mayotte to produce anti-aging compounds. Future work will focus on the isolation and the characterization of bioactive molecules.

scholarly journals Biological and Chemical Diversity of Marine Sponge-Derived Microorganisms over the Last Two Decades from 1998 to 2017

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 853 ◽  
Author(s):  
Mei-Mei Cheng ◽  
Xu-Li Tang ◽  
Yan-Ting Sun ◽  
Dong-Yang Song ◽  
Yu-Jing Cheng ◽  
...  
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Marine Sponge ◽  
Marine Sponges ◽  
Chemical Diversity ◽  
Comprehensive Overview ◽  
Bioactive Secondary Metabolites ◽  
The Relationship ◽  
Product Chemistry

Marine sponges are well known as rich sources of biologically natural products. Growing evidence indicates that sponges harbor a wealth of microorganisms in their bodies, which are likely to be the true producers of bioactive secondary metabolites. In order to promote the study of natural product chemistry and explore the relationship between microorganisms and their sponge hosts, in this review, we give a comprehensive overview of the structures, sources, and activities of the 774 new marine natural products from sponge-derived microorganisms described over the last two decades from 1998 to 2017.

scholarly journals Natural Product Repertoire of the Genus Amphimedon

Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 19 ◽  
Author(s):  
Nourhan Shady ◽  
Mostafa Fouad ◽  
Mohamed Salah Kamel ◽  
Tanja Schirmeister ◽  
Usama Abdelmohsen
Keyword(s):  
Secondary Metabolites ◽  
Natural Product ◽  
Bioactive Compounds ◽  
Biological Activities ◽  
Marine Sponges ◽  
Rich Source ◽  
Undescribed Species ◽  
Pharmacological Activities ◽  
Wide Range ◽  
Complete Survey

Marine sponges are a very attractive and rich source in the production of novel bioactive compounds. The sponges exhibit a wide range of pharmacological activities. The genus Amphimedon consists of various species, such as viridis, compressa, complanata, and terpenensis, along with a handful of undescribed species. The Amphimedon genus is a rich source of secondary metabolites containing diverse chemical classes, including alkaloids, ceramides, cerebrososides, and terpenes, with various valuable biological activities. This review covers the literature from January 1983 until January 2018 and provides a complete survey of all the compounds isolated from the genus Amphimedon and the associated microbiota, along with their corresponding biological activities, whenever applicable.

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