Names | |
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Systematic IUPAC name (2S,4S)-5,5,5-Trichloro-4-methyl-N-[(1S)-1-(1,3-thiazol-2-yl)ethyl]-2-[(3S)-4,4,4-trichloro-N,3-dimethylbutanamido]pentanamide | |
Other names Dysidenine;Pentanamide, 5,5,5-trichloro-4-methyl-2-(methyl(4,4,4-trichloro-3-methyl-1-oxobutyl)amino)-N-(1-(2-thiazolyl)ethyl)-;(2S,4S)-5,5,5-Trichloro-4-methyl-2-[methyl[(S)-4,4,4-trichloro-3-methyl-1-oxobutyl]amino]-N-[(S)-1-(2-thiazolyl)ethyl]pentanamide | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C17H23Cl6N3O2S | |
Molar mass | 546.166 |
Appearance | Fine white crystalline powder |
Melting point | 98 °C (208 °F; 371 K) |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Dysidenin is a alkaloid toxin derived from the marine sponge Lamellodysidea herbacea and has been identified as lethal to certain fish species and other marine organisms. The toxic mechanism of dysidenin is linked to its ability to inhibit iodide transport in thyroid cells, which is a crucial process for thyroid hormone synthesis and subsequent metabolic regulation in organisms. [1] The inhibition of iodide transport could potentially lead to disrupted thyroid functions, causing a range of metabolic issues. This aspect of dysidenin not only sheds light on ecological interactions within marine environments but also suggests potential medical applications under controlled conditions.
There is a notable regional variation in the metabolites produced by Lamellodysidea herbacea, as evidenced by the isolation of dysidenin from organism samples obtained from the Great Barrier Reef, while it was absent in samples from the Caroline Islands. [2] This geographical variation in metabolite expression could be attributed to differences in environmental conditions, predator-prey interactions, or microbial symbiont communities within these regions. It highlights the adaptive metabolomic responses of marine sponges to their local ecological settings. This variance underscores the need for a deeper understanding of how spatial differences in marine ecosystems influence the chemical ecology of resident organisms.
The scientific exploration of dysidenin commenced in 1977 with its initial isolation. [3] Over the ensuing decades, the elucidation of dysidenin's structural and toxicological properties has contributed significantly to the broader field of marine natural products, which is a domain rich with potential pharmacological candidates and ecological indicators. The trajectory from its discovery to the present understanding exemplifies the gradual, yet rewarding, unraveling of marine-derived substances, mirroring the broader narrative of marine natural product research.
The discourse surrounding dysidenin serves as a reflection of the larger narrative on marine natural products, an arena filled with both potential and challenges. Dysidenin serves as a reminder of the delicate equilibrium within marine ecosystems and the inherent link between the health of marine habitats and the biodiscovery potential they hold. A nuanced understanding of dysidenin, both as an ecological factor and a potential biomedical resource, calls for a multidisciplinary approach anchored by rigorous analytical examination, and an appreciation for the complex, intertwined narratives of marine ecological and biochemical dynamics.
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own, defense, and interactions with other organisms.
A biogenic substance is a product made by or of life forms. While the term originally was specific to metabolite compounds that had toxic effects on other organisms, it has developed to encompass any constituents, secretions, and metabolites of plants or animals. In context of molecular biology, biogenic substances are referred to as biomolecules. They are generally isolated and measured through the use of chromatography and mass spectrometry techniques. Additionally, the transformation and exchange of biogenic substances can by modelled in the environment, particularly their transport in waterways.
Pharmacognosy is the study of crude drugs obtained from medicinal plants, animals, fungi, and other natural sources. The American Society of Pharmacognosy defines pharmacognosy as "the study of the physical, chemical, biochemical, and biological properties of drugs, drug substances, or potential drugs or drug substances of natural origin as well as the search for new drugs from natural sources".
Chemical ecology is the study of chemically mediated interactions between living organisms, and the effects of those interactions on the demography, behavior and ultimately evolution of the organisms involved. It is thus a vast and highly interdisciplinary field. Chemical ecologists seek to identify the specific molecules that function as signals mediating community or ecosystem processes and to understand the evolution of these signals. The substances that serve in such roles are typically small, readily-diffusible organic molecules, but can also include larger molecules and small peptides.
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.
Burkholderia is a genus of Pseudomonadota whose pathogenic members include the Burkholderia cepacia complex, which attacks humans and Burkholderia mallei, responsible for glanders, a disease that occurs mostly in horses and related animals; Burkholderia pseudomallei, causative agent of melioidosis; and Burkholderia cepacia, an important pathogen of pulmonary infections in people with cystic fibrosis (CF). Burkholderia species is also found in marine environments. S.I. Paul et al. (2021) isolated and characterized Burkholderia cepacia from marine sponges of the Saint Martin's Island of the Bay of Bengal, Bangladesh.
The latrunculins are a family of natural products and toxins produced by certain sponges, including genus Latrunculia and Negombata, whence the name is derived. It binds actin monomers near the nucleotide binding cleft with 1:1 stoichiometry and prevents them from polymerizing. Administered in vivo, this effect results in disruption of the actin filaments of the cytoskeleton, and allows visualization of the corresponding changes made to the cellular processes. This property is similar to that of cytochalasin, but has a narrow effective concentration range. Latrunculin has been used to great effect in the discovery of cadherin distribution regulation and has potential medical applications. Latrunculin A, a type of the toxin, was found to be able to make reversible morphological changes to mammalian cells by disrupting the actin network.
Marine pharmacognosy is the investigation and identification of medically important plants and animals in the marine environment. It is a sub branch of terrestrial pharmacognosy. Generally the drugs are obtained from the marine species of bacteria, virus, algae, fungi and sponges. It is a relatively new field of study in western medicine, although many marine organisms were used in traditional Chinese medicine. It was not until 2004 that the first FDA approval of a drug came directly from the sea: ziconotide, which was isolated from a marine cone snail.
Ecotoxicity, the subject of study in the field of ecotoxicology, refers to the biological, chemical or physical stressors that affect ecosystems. Such stressors could occur in the natural environment at densities, concentrations, or levels high enough to disrupt natural biochemical and physiological behavior and interactions. This ultimately affects all living organisms that comprise an ecosystem.
Iodine is an essential trace element in biological systems. It has the distinction of being the heaviest element commonly needed by living organisms as well as the second-heaviest known to be used by any form of life. It is a component of biochemical pathways in organisms from all biological kingdoms, suggesting its fundamental significance throughout the evolutionary history of life.
Stichodactyla helianthus, commonly known as sun anemone, is a sea anemone of the family Stichodactylidae. Helianthus stems from the Greek words ἡλιος, and ἀνθος, meaning flower. S. helianthus is a large, green, sessile, carpet-like sea anemone, from the Caribbean. It lives in shallow areas with mild to strong currents.
Chemical defense is a strategy employed by many organisms to avoid consumption by producing toxic or repellent metabolites or chemical warnings which incite defensive behavioral changes. The production of defensive chemicals occurs in plants, fungi, and bacteria, as well as invertebrate and vertebrate animals. The class of chemicals produced by organisms that are considered defensive may be considered in a strict sense to only apply to those aiding an organism in escaping herbivory or predation. However, the distinction between types of chemical interaction is subjective and defensive chemicals may also be considered to protect against reduced fitness by pests, parasites, and competitors. Repellent rather than toxic metabolites are allomones, a sub category signaling metabolites known as semiochemicals. Many chemicals used for defensive purposes are secondary metabolites derived from primary metabolites which serve a physiological purpose in the organism. Secondary metabolites produced by plants are consumed and sequestered by a variety of arthropods and, in turn, toxins found in some amphibians, snakes, and even birds can be traced back to arthropod prey. There are a variety of special cases for considering mammalian antipredatory adaptations as chemical defenses as well.
Secondary metabolism produces a large number of specialized compounds that do not aid in the growth and development of plants but are required for the plant to survive in its environment. Secondary metabolism is connected to primary metabolism by using building blocks and biosynthetic enzymes derived from primary metabolism. Primary metabolism governs all basic physiological processes that allow a plant to grow and set seeds, by translating the genetic code into proteins, carbohydrates, and amino acids. Specialized compounds from secondary metabolism are essential for communicating with other organisms in mutualistic or antagonistic interactions. They further assist in coping with abiotic stress such as increased UV-radiation. The broad functional spectrum of specialized metabolism is still not fully understood. In any case, a good balance between products of primary and secondary metabolism is best for a plant’s optimal growth and development as well as for its effective coping with often changing environmental conditions. Well known specialized compounds include alkaloids, polyphenols including flavonoids, and terpenoids. Humans use many of these compounds for culinary, medicinal and nutraceutical purposes.
Sea sponge aquaculture is the process of farming sea sponges under controlled conditions. It has been conducted in the world's oceans for centuries using a number of aquaculture techniques. There are many factors such as light, salinity, pH, dissolved oxygen and the accumulation of waste products that influence the growth rate of sponges. The benefits of sea sponge aquaculture are realised as a result of its ease of establishment, minimum infrastructure requirements and the potential to be used as a source of income for populations living in developing countries. Sea sponges are produced on a commercial scale to be used as bath sponges or to extract biologically active compounds which are found in certain sponge species. Techniques such as the rope and mesh bag method are used to culture sponges independently or within an integrated multi-trophic aquaculture system setting. One of the only true sustainable sea sponges cultivated in the world occur in the region of Micronesia, with a number of growing and production methods used to ensure and maintain the continued sustainability of these farmed species.
Phycotoxins are complex allelopathic chemicals produced by eukaryotic and prokaryotic algal secondary metabolic pathways. More simply, these are toxic chemicals synthesized by photosynthetic organisms. These metabolites are not harmful to the producer but may be toxic to either one or many members of the marine food web. This page focuses on phycotoxins produced by marine microalgae; however, freshwater algae and macroalgae are known phycotoxin producers and may exhibit analogous ecological dynamics. In the pelagic marine food web, phytoplankton are subjected to grazing by macro- and micro-zooplankton as well as competition for nutrients with other phytoplankton species. Marine bacteria try to obtain a share of organic carbon by maintaining symbiotic, parasitic, commensal, or predatory interactions with phytoplankton. Other bacteria will degrade dead phytoplankton or consume organic carbon released by viral lysis. The production of toxins is one strategy that phytoplankton use to deal with this broad range of predators, competitors, and parasites. Smetacek suggested that "planktonic evolution is ruled by protection and not competition. The many shapes of plankton reflect defense responses to specific attack systems". Indeed, phytoplankton retain an abundance of mechanical and chemical defense mechanisms including cell walls, spines, chain/colony formation, and toxic chemical production. These morphological and physiological features have been cited as evidence for strong predatory pressure in the marine environment. However, the importance of competition is also demonstrated by the production of phycotoxins that negatively impact other phytoplankton species. Flagellates are the principle producers of phycotoxins; however, there are known toxigenic diatoms, cyanobacteria, prymnesiophytes, and raphidophytes. Because many of these allelochemicals are large and energetically expensive to produce, they are synthesized in small quantities. However, phycotoxins are known to accumulate in other organisms and can reach high concentrations during algal blooms. Additionally, as biologically active metabolites, phycotoxins may produce ecological effects at low concentrations. These effects may be subtle, but have the potential to impact the biogeographic distributions of phytoplankton and bloom dynamics.
This glossary of biology terms is a list of definitions of fundamental terms and concepts used in biology, the study of life and of living organisms. It is intended as introductory material for novices; for more specific and technical definitions from sub-disciplines and related fields, see Glossary of cell biology, Glossary of genetics, Glossary of evolutionary biology, Glossary of ecology, Glossary of environmental science and Glossary of scientific naming, or any of the organism-specific glossaries in Category:Glossaries of biology.
Lacking an immune system, protective shell, or mobility, sponges have developed an ability to synthesize a variety of unusual compounds for survival. C-nucleosides isolated from Caribbean Cryptotethya crypta, were the basis for the synthesis of zidovudine (AZT), aciclovir (Cyclovir), cytarabine (Depocyt), and cytarabine derivative gemcitabine (Gemzar).
A microbiome is the community of microorganisms that can usually be found living together in any given habitat. It was defined more precisely in 1988 by Whipps et al. as "a characteristic microbial community occupying a reasonably well-defined habitat which has distinct physio-chemical properties. The term thus not only refers to the microorganisms involved but also encompasses their theatre of activity". In 2020, an international panel of experts published the outcome of their discussions on the definition of the microbiome. They proposed a definition of the microbiome based on a revival of the "compact, clear, and comprehensive description of the term" as originally provided by Whipps et al., but supplemented with two explanatory paragraphs. The first explanatory paragraph pronounces the dynamic character of the microbiome, and the second explanatory paragraph clearly separates the term microbiota from the term microbiome.
Microbial symbiosis in marine animals was not discovered until 1981. In the time following, symbiotic relationships between marine invertebrates and chemoautotrophic bacteria have been found in a variety of ecosystems, ranging from shallow coastal waters to deep-sea hydrothermal vents. Symbiosis is a way for marine organisms to find creative ways to survive in a very dynamic environment. They are different in relation to how dependent the organisms are on each other or how they are associated. It is also considered a selective force behind evolution in some scientific aspects. The symbiotic relationships of organisms has the ability to change behavior, morphology and metabolic pathways. With increased recognition and research, new terminology also arises, such as holobiont, which the relationship between a host and its symbionts as one grouping. Many scientists will look at the hologenome, which is the combined genetic information of the host and its symbionts. These terms are more commonly used to describe microbial symbionts.
Metabolic gene clusters or biosynthetic gene clusters are tightly linked sets of mostly non-homologous genes participating in a common, discrete metabolic pathway. The genes are in physical vicinity to each other on the genome, and their expression is often coregulated. Metabolic gene clusters are common features of bacterial and most fungal genomes. They are less often found in other organisms. They are most widely known for producing secondary metabolites, the source or basis of most pharmaceutical compounds, natural toxins, chemical communication, and chemical warfare between organisms. Metabolic gene clusters are also involved in nutrient acquisition, toxin degradation, antimicrobial resistance, and vitamin biosynthesis. Given all these properties of metabolic gene clusters, they play a key role in shaping microbial ecosystems, including microbiome-host interactions. Thus several computational genomics tools have been developed to predict metabolic gene clusters.