Cheilanthane Sesterterpenes, Protein Kinase Inhibitors, from a Marine Sponge of the Genus <i>Ircinia</i>

Buchanan, Malcolm S.; Edser, Annette; King, Gordon; Whitmore, Jacqueline B; Quinn, Ronald J.

doi:10.1021/np0004597

Cited by 42 publications

(43 citation statements)

References 11 publications

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“…Until now, natural tetracyclic compounds derived from regular polyprenes, known as scalaranes, had been reported only from some marine sponges (21,22). Similar tricyclic structures (cheilanthanes) are known in the geologic record in association with deposits of Tasmanites algae (23).…”

Section: Biological and Environmental Implicationsmentioning

confidence: 99%

A polycyclic terpenoid that alleviates oxidative stress

Bosak

Losick

Pearson

2008

Proc. Natl. Acad. Sci. U.S.A.

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Polycyclic terpenoid lipids such as hopanes and steranes have been widely used to understand ancient biology, Earth history, and the oxygenation of the ocean-atmosphere system. Some of these lipids are believed to be produced only by aerobic organisms, whereas others actually require molecular oxygen for their biosynthesis. A persistent question remains: Did some polycyclic lipids initially evolve in response to certain environmental or metabolic stresses, including the presence of oxygen? Here, we identify tetracyclic isoprenoids in spores of the bacterium Bacillus subtilis. We call them sporulenes. They are produced by cyclization of regular polyprenes, a reaction that is more favorable chemically than the formation of terpenoids such as hopanoids and steroids from squalene. The simplicity of the reaction suggests that the B. subtilis cyclase may be analogous to evolutionarily ancient cyclases. We show that these molecules increase the resistance of spores to a reactive oxygen species, demonstrating a specific physiological role for a nonpigment bacterial lipid biomarker. Geostable derivatives of these compounds in sediments could thus be used as direct indicators of oxidative stress and aerobic environments.biomarker ͉ spores ͉ squalene-hopene cyclase ͉ lipid ͉ peroxide resistance P olycyclic terpenoids are a class of organic molecules that includes cholesterol and numerous other related lipids. Their molecular fossils, which are ubiquitous in the sedimentary rock record, are used as records of ancient bacterial and eukaryotic life. For example, the timing of the onset of oxygenic photosynthesis has been reported to be as early as 2.7 billion years ago (1) based on the detection of polycyclic terpenoids presumably derived from Cyanobacteria (2). However, recent studies have questioned this assumption and have urged caution about making taxonomic associations of specific lipid biomarkers with specific microbial groups (3, 4).Here, we take a different approach to this debate by showing definitively that some polycyclic terpenoids reflect a specific physiological function. The association of molecular fossils with physiological functions reduces the dependence of molecular fossils on specific organisms and taxonomic groups. Significantly, we demonstrate in vivo the protective role of a class of polycyclic terpenoids against a reactive oxygen species. Geostable derivatives of these compounds, called sporulenes, could become more definitive geologic markers for aerobic bacteria and environments. Future studies of the specific biological roles of other polycyclic terpenoids may greatly inform the interpretations of the past, including the oxygenation of the Earth. Biosynthesis of Polycyclic Terpenoids by Bacillus subtilisThe best-studied polycyclic terpenoids, tetracyclic sterols and pentacyclic hopanoids, are produced enzymatically from acyclic 30-carbon (C 30 ) precursors by a family of squalene and oxidosqualene cyclases (5, 6). A gene (sqhC) encoding a putative squalene cyclase enzyme (SqhC) is present in a two...

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Section: Biological and Environmental Implicationsmentioning

confidence: 99%

A polycyclic terpenoid that alleviates oxidative stress

Bosak

Losick

Pearson

2008

Proc. Natl. Acad. Sci. U.S.A.

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“…I. strobilina contains variabilin, a furanosesterterpene that has been identified as a fish feeding deterrent (16). A diverse group of metabolites has been found from other sponges in the genus Ircinia and includes other sesterterpenes (1,3,29,38,52,65,76). The compounds ircinal A and B, precursors of antimalarial manzamine alkaloids, were isolated from the Okinawan marine sponge Ircinia sp.…”

mentioning

confidence: 99%

Monitoring Bacterial Diversity of the Marine Sponge Ircinia strobilina upon Transfer into Aquaculture

Mohamed

Rao

Hamann

et al. 2008

Appl Environ Microbiol

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Marine sponges in the genus Ircinia are known to be good sources of secondary metabolites with biological activities. A major obstacle in the development of sponge-derived metabolites is the difficulty in ensuring an economic, sustainable supply of the metabolites. A promising strategy is the ex situ culture of sponges in closed or semiclosed aquaculture systems. In this study, the marine sponge Ircinia strobilina (order Dictyoceratida: family Irciniidae) was collected from the wild and maintained for a year in a recirculating aquaculture system. Microbiological and molecular community analyses were performed on freshly collected sponges and sponges maintained in aquaculture for 3 months and 9 months. Chemical analyses were performed on wild collected sponges and individuals maintained in aquaculture for 3 months and 1 year. Denaturing gradient gel electrophoresis was used to assess the complexity of and to monitor changes in the microbial communities associated with I. strobilina. Culture-based and molecular techniques showed an increase in the Bacteroidetes and Alpha-and Gammaproteobacteria components of the bacterial community in aquaculture. Populations affiliated with Beta-and Deltaproteobacteria, Clostridia, and Planctomycetes emerged in sponges maintained in aquaculture. The diversity of bacterial communities increased upon transfer into aquaculture.

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“…[73] and extracts from Iotrochota birotulata and Spongia barbara [74];hymenin ( 25 ) and hymenialdisine ( 27 ), from Stylotella aurantium [75];a methanol fraction from Batzella sp. [76];…”

Section: Marine Spongesmentioning

confidence: 99%

Marine Sponges and Bacteria as Challenging Sources of Enzyme Inhibitors for Pharmacological Applications

et al. 2017

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Enzymes play key roles in different cellular processes, for example, in signal transduction, cell differentiation and proliferation, metabolic processes, DNA damage repair, apoptosis, and response to stress. A deregulation of enzymes has been considered one of the first causes of several diseases, including cancers. In the last several years, enzyme inhibitors, being good candidates as drugs in the pathogenic processes, have received an increasing amount of attention for their potential application in pharmacology. The marine environment is considered a challenging source of enzyme inhibitors for pharmacological applications. In this review, we report on secondary metabolites with enzyme inhibitory activity, focusing our attention on marine sponges and bacteria as promising sources. In the case of sponges, we only reported the kinase inhibitors, because this class was the most representative isolated so far from these marine organisms.

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Cheilanthane Sesterterpenes, Protein Kinase Inhibitors, from a Marine Sponge of the Genus Ircinia

Cited by 42 publications

References 11 publications

A polycyclic terpenoid that alleviates oxidative stress

A polycyclic terpenoid that alleviates oxidative stress

Monitoring Bacterial Diversity of the Marine Sponge Ircinia strobilina upon Transfer into Aquaculture

Marine Sponges and Bacteria as Challenging Sources of Enzyme Inhibitors for Pharmacological Applications

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