Isocyanates in marine sponges: Axisocyanate-3, a new sesquiterpene from Acanthella cavernosa

Jumaryatno, Pinus; Rands-Trevor, Karen; Blanchfield, Joanne T.; Garson, Mary J.

doi:10.3998/ark.5550190.0008.713

Cited by 10 publications

(12 citation statements)

References 14 publications

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“…575 A study of the terpenoid content of Acanthella cavernosa (E. coast, Australia) led to the isolation of 10-isothiocyanatoguai-6-ene 484 and 7-isocyano-7,8-dihydro-a-bisabolene 485, 576 while in a separate report, the same group described the isolation of axisocyanate-3 486 from the same sponge. 577 Two ethyl ethers, 11-ethoxy-3-formamidotheonellin 487 and 7-ethoxy-3-formamidobisabolane-8,10-diene 488, were obtained from Axinyssa aff. variabilis (Hainan, China); the authors suggested that they may be artifacts of solvolysis.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2009

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This review covers the literature published in 2007 for marine natural products, with 948 citations(627 for the period January to December 2007) referring to compounds isolated from marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, cnidarians,bryozoans, molluscs, tunicates, echinoderms and true mangrove plants. The emphasis is on new compounds (961 for 2007), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.1 Introduction, 2 Reviews, 3 Marine microorganisms and phytoplankton, 4 Green algae, 5 Brown algae, 6 Red algae, 7 Sponges, 8 Cnidarians, 9 Bryozoans, 10 Molluscs, 11 Tunicates (ascidians),12 Echinoderms, 13 Miscellaneous, 14 Conclusion, 15 References.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2009

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“…Some siphonodictyals and corallidictyals have also been reported to have antimicrobial activity [ 28 , 29 ]. The other sponges from which compounds with antimicrobial activity have been isolated are Fasciospongia cavernosa [ 30 ] and Acanthella cavernosa [ 31 - 33 ]. A careful study of the previous literature showed that several compounds with AChEI activity, isolated from the sponges, mostly derivatives of alkaloids and terpenes [ 22 ].…”

Section: Discussionmentioning

confidence: 99%

A marine sponge associated strain of Bacillus subtilis and other marine bacteria can produce anticholinesterase compounds

et al. 2014

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BackgroundAcetylcholinesterase (AChE) inhibitors or anticholinesterases reduce the activity of enzyme acetylcholinesterase that degrades the neurotransmitter acetylcholine in the brain. The inhibitors have a significant pharmacological role in neurodegenerative diseases like Alzheimer’s and Parkinson’s etc. Although plants have been a significant source of these compounds, there are very few sporadic reports of microorganisms producing such inhibitors. Anticholinesterase activity in bacterial associates of marine soft corals and sponges were not previously reported.ResultsWe screened 887 marine bacteria for the presence of acetylcholinesterase inhibitors, in a microplate based assay, and found that 140 (15.8%) of them inhibit the electric eel enzyme, acetylcholinesterase. Majority of the active isolates were bacterial associates of soft corals followed by sediment isolates while most of the potent inhibitors belonged to the bacterial associates of marine sponges. Maximum inhibition (54%) was exhibited by a bacterial strain M18SP4P (ii), isolated from the marine sponge Fasciospongia cavernosa. Based on phenotypic characterization and 16S rDNA sequencing, the strain was identified as Bacillus subtilis - revealing yet another activity in a strain of the model organism that is considered to be a cell factory. TLC bioautography of the methanol extract of this culture, showed the presence of two major components having this activity, when compared to Galanthamine, the positive control.ConclusionFrom the results of our study, we conclude that acetylcholinesterase inhibitors are quite prevalent in marine bacteria, particularly the bacterial associates of marine invertebrates. Several potential AChE inhibitors in marine bacteria are waiting to be discovered to provide easily manipulable natural sources for the mass production of these therapeutic compounds.

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“…Compared to the diterpenes, the larger group of marine isonitriles and related compounds contain a sesquiterpenoid backbone and are subdivided into nine classes. Similarly to the diterpene variants, these compounds are predominantly found in Bubarida, former members of Suberitida, and closely related species, e.g., [ 150 , 151 ] (see Figure 1 ), while several have also been described from unrelated taxa. These outliers comprise isonitriloids of the classes axanes, eudesmanes, aromadendranes, and epimaalianes, being reported from Axinella cannabina, e.g., [ 152 ], while unspecified Halichondria sp.…”

Section: Specificity and Phylogenetic Relevance Of Sponge Compoundsmentioning

confidence: 99%

A Soft Spot for Chemistry–Current Taxonomic and Evolutionary Implications of Sponge Secondary Metabolite Distribution

et al. 2021

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Marine sponges are the most prolific marine sources for discovery of novel bioactive compounds. Sponge secondary metabolites are sought-after for their potential in pharmaceutical applications, and in the past, they were also used as taxonomic markers alongside the difficult and homoplasy-prone sponge morphology for species delineation (chemotaxonomy). The understanding of phylogenetic distribution and distinctiveness of metabolites to sponge lineages is pivotal to reveal pathways and evolution of compound production in sponges. This benefits the discovery rate and yield of bioprospecting for novel marine natural products by identifying lineages with high potential of being new sources of valuable sponge compounds. In this review, we summarize the current biochemical data on sponges and compare the metabolite distribution against a sponge phylogeny. We assess compound specificity to lineages, potential convergences, and suitability as diagnostic phylogenetic markers. Our study finds compound distribution corroborating current (molecular) phylogenetic hypotheses, which include yet unaccepted polyphyly of several demosponge orders and families. Likewise, several compounds and compound groups display a high degree of lineage specificity, which suggests homologous biosynthetic pathways among their taxa, which identifies yet unstudied species of this lineage as promising bioprospecting targets.

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Isocyanates in marine sponges: Axisocyanate-3, a new sesquiterpene from Acanthella cavernosa

Cited by 10 publications

References 14 publications

Marine natural products

Marine natural products

A marine sponge associated strain of Bacillus subtilis and other marine bacteria can produce anticholinesterase compounds

A Soft Spot for Chemistry–Current Taxonomic and Evolutionary Implications of Sponge Secondary Metabolite Distribution

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