Marine natural products

Blunt, John W.; Copp, Brent R.; Keyzers, Robert A.; Munro, Murray H. G.; Prinsep, Michèle R.

doi:10.1039/c3np70117d

Cited by 462 publications

(318 citation statements)

References 993 publications

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“…Combined instances of central and axial chirality are known to exist, as in the previously-mentioned example of the bisnicalaterines, however the recent discovery of the diarylheptanoid Tedarene B (Figure 16, compound 71) from extracts of the widespread marine sponge Tedania ignus marked a rare example of a natural product containing axial, planar and point-chiral elements. 115 Though Tedarene B has been briefly mentioned in recent reviews, [116][117][118] its nature as a unique atropisomeric architecture, combined with the brevity of previous reviews warrants its mention herein.…”

Section: Tedarene B: the Smallest Central Planar And Axially-chiralmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583. A twist of nature-the significance of atropisomers in biological systems AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized. AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Section: Tedarene B: the Smallest Central Planar And Axially-chiralmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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“…[1][2][3] Sponge derived compounds are not only displayed unique chemical structures but also interesting biological properties and made sponges become a potent source of lead compounds for new drug discovery. 1,4) Sponge genus Smenospongia (order Dictyoceratida, family Thorectidae) has been found comprising 19 species.…”

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confidence: 99%

Naphtoquinones and Sesquiterpene Cyclopentenones from the Sponge <i>Smenospongia cerebriformis</i> with Their Cytotoxic Activity

et al. 2017

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Two new naphtoquinones (smenoceronesMarine sponges have produced a huge variety of secondary metabolites in which approximate 300 new structures were reported annually in the past decade.1-3) Sponge derived compounds are not only displayed unique chemical structures but also interesting biological properties and made sponges become a potent source of lead compounds for new drug discovery.1,4) Sponge genus Smenospongia (order Dictyoceratida, family Thorectidae) has been found comprising 19 species. Especially, 12 new species were described in recent three years. 5)Smenospongia sponges were mentioned to produce large number of brominated indole alkaloids, 6) popyketides, 7) sesterterpenes, 8) and unique structure of merosesquiterpenes 9,10) such as sesquiterpene quinone, sesquiterpene phenol, and sesquiterpene cyclopentenone. In this paper, we report the isolation, structure determination, and cytotoxic effect towards lung carcinoma (LU-1), hepatocellular carcinoma (HepG-2), promyelocytic leukemia (HL-60), breast carcinoma (MCF-7), and melanoma (SK-Mel-2) human cancer cells of two new naphtoquinones and four known sesquiterpene cyclopentenones from the sponge S. cerebriformis living at the Eastern Sea of Vietnam.

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“…For instance, marine sponges are valued for their ecosystem services, in particular cycling and retaining nutrients on coral reefs (Alexander et al, 2014;de Goeij et al, 2013;Rix et al, 2016), and as a source of bioactive secondary metabolites with commercial potential (Blunt et al, 2014;Konstantinidis & Tiedje, 2004;Leal et al, 2012;Mehbub et al, 2014;Thomas et al, 2010). It is accepted that the low commercialisation rate of sponge holobiont derived natural products is due to the inability to reliably produce sponge biomass (Belarbi, 2003;Leal et al, 2014;Osinga et al, 1999;Schippers et al, 2012;Sipkema et al, 2005;Wijffels, 2008).…”

Section: Overviewmentioning

confidence: 99%

“…In addition to their ecosystem services, marine sponges and their associated bacteria are the most prolific producers of secondary metabolites in the marine environment (Blunt et al, 2014;Haygood et al, 1999;Laport et al, 2009;Leal et al, 2012;Thakur & Müller, 2004;Thomas et al, 2010). Novel bioactive compounds are routinely discovered and identified, but the low concentrations in which they often exist means that sourcing them from wild stocks of sponges would require unsustainable levels of harvesting (Sipkema et al, 2005).…”

Section: Sponges Are Key Nutrient Cyclers and Producers Of Secondary mentioning

confidence: 99%

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Modelling sponge-symbiont metabolism

Watson¹

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Marine sponges are increasingly being recognised for their nutrient cycling ecosystem services, linking pelagic nutrients with the benthic ecosystem. Furthermore, sponges are the most prolific producers of bioactive secondary metabolites in the marine environment. Despite their ecological and commercial value, little is know about the metabolic processes that are responsible. The inability to produce sufficient sponge biomass, and thus specific bioactive compounds, has been repeatedly identified as a major bottleneck towards commercialising sponge holobiont derived drugs. Likewise, nutrient cycling by sponges has been a relatively recent advancement in marine ecology and the scale of this process is unknown. This thesis takes a systems approach to understanding sponge-symbiont metabolic processes by utilising the genomic resources available for the demosponge Amphimedon queenslandica and its bacterial symbiont AqS1. Specifically, I undertake genome-scale modelling and metabolic flux analyses to investigate the metabolic networks present in this sponge as well as its associated vertically-transmitted microbial symbiont. The goal of this thesis is to generate the data required for, and subsequently develop, a dual-species genome-scale metabolic model for A. queenslandica and AqS1. This will provide a framework to further our understanding of how sponges produce their biomass while living in an oligotrophic, tropical reef environment.To develop a genome-scale metabolic model, the biochemical composition of the organism must first be determined. Knowledge of the relative quantities of macromolecules and their respective building blocks (e.g. protein and amino acids) is vital, as each requires different substrates, enzymes and cofactors for their synthesis. I adapted and developed methods to characterise the composition and abundance of DNA, RNA, protein, lipids and carbohydrates in a marine sponge. These methods are described in detail that allows them to be easily transferred to other, non-model, large marine organisms. This is followed by a detailed analysis of A. queenslandica's macromolecular, amino acid, fatty acid and sterol composition. The biochemical data from this chapter was used to generate a biomass equation that represent the average composition of adult A. queenslandica in the metabolic model. 3To understand how the metabolic network may work towards producing more biomass, it must be considered in the context of the environmental conditions that naturally constrain growth. The dominant environmental constraint on growth on an oligotrophic reef system is nutrient availability.The abundance of key elements, such as carbon and nitrogen, were quantified throughout the course of a year. To investigate effects on the sponge of any changes in nutrient availability, I concurrently sampled sponges and analysed their biochemical composition to the macromolecular level. Chapter 4 presents these data and discusses a number of trends and correlations in the biochemical composition of the sponges with chan...

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Marine natural products

Cited by 462 publications

References 993 publications

A twist of nature – the significance of atropisomers in biological systems

A twist of nature – the significance of atropisomers in biological systems

Naphtoquinones and Sesquiterpene Cyclopentenones from the Sponge <i>Smenospongia cerebriformis</i> with Their Cytotoxic Activity

Modelling sponge-symbiont metabolism

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