 | |
| Names | |
|---|---|
| Preferred IUPAC name (12bS)-12b-Methyl-2,3-dihydro-1H-tetrapheno[5,4-bc]furan-6,8,11(12bH)-trione | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
| |
| |
| Properties | |
| C20H14O4 | |
| Molar mass | 318.323 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Xestoquinone is a bio-active isolate of the marine sponge Xestospongia . [1] [2]
Sponges, the members of the phylum Porifera, are a basal animal clade as a sister of the diploblasts. They are multicellular organisms that have bodies full of pores and channels allowing water to circulate through them, consisting of jelly-like mesohyl sandwiched between two thin layers of cells.
Hexactinellid sponges are sponges with a skeleton made of four- and/or six-pointed siliceous spicules, often referred to as glass sponges. They are usually classified along with other sponges in the phylum Porifera, but some researchers consider them sufficiently distinct to deserve their own phylum, Symplasma. Some experts believe glass sponges are the longest-lived animals on earth; these scientists tentatively estimate a maximum age of up to 15,000 years.
The giant barrel sponge is the largest species of sponge found growing on Caribbean coral reefs. It is common at depths greater than 10 metres (33 ft) down to 120 metres (390 ft) and can reach a diameter of 1.8 metres. It is typically brownish-red to brownish-gray in color, with a hard or stony texture. The giant barrel sponge has been called the "redwood of the reef" because of its size and estimated lifespan of hundreds to a thousand or more years. It is perhaps the best-studied species of sponge in the sea; a population on Conch Reef, in the Florida Keys, has been monitored and studied since 1997.
The Liebeskind–Srogl coupling reaction is an organic reaction forming a new carbon–carbon bond from a thioester and a boronic acid using a metal catalyst. It is a cross-coupling reaction. This reaction was invented by and named after Jiri Srogl from the Academy of Sciences, Czech Republic, and Lanny S. Liebeskind from Emory University, Atlanta, Georgia, USA. There are three generations of this reaction, with the first generation shown below. The original transformation used catalytic Pd(0), TFP = tris(2-furyl)phosphine as an additional ligand and stoichiometric CuTC = copper(I) thiophene-2-carboxylate as a co-metal catalyst. The overall reaction scheme is shown below.
Xestospongia testudinaria is a species of barrel sponge in the family Petrosiidae. More commonly known as Giant Barrel Sponges, they have the basic structure of a typical sponge. Their body is made of a reticulation of cells aggregate on a siliceous scaffold composed of small spikes called spicules. Water is taken into the inner chamber of the sponge through ostia. Flagellated choanocytes line the inner chamber and help generate water currents through the sponge.
Arsenicin A is a naturally occurring arsenic heterocycle with the molecular formula C3H6As4O3. It was first isolated from the New Caledonian marine sponge Echinochalina bargibanti. The compound was characterized by computational and spectroscopic techniques and found to possess a cage-like structure similar to adamantane in which the four methanetriyl carbon bridgeheads are replaced by arsenic atoms and three of the six methylene bridges are replaced by oxygen atoms. It is the first polyarsenic compound ever found in nature. Subsequently, the proposed structure was prepared in large quantities via total synthesis and the structure was confirmed by x-ray crystallography. The molecule is chiral, and has been resolved into its two enantiomers. Arsenicin A is active against promelocytic leukemia cells at lower concentrations than the arsenic(III) oxide drug Trisenox.
Spicules are structural elements found in most sponges. The meshing of many spicules serves as the sponge's skeleton and thus it provides structural support and potentially defense against predators.
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.
Callyspongia (Cladochalina) aculeata, commonly known as the branching vase sponge is a species of sea sponge in the family Callyspongiidae. Poriferans are typically characterized by ostia, pores that filter out plankton, with an osculum as the opening which water leaves through, and choanocytes trap food particles.
Neopetrosia proxima is a species of marine petrosiid sponge native to the tropical and subtropical waters of the western Atlantic Ocean.
Neopetrosia subtriangularis is a species of marine petrosiid sponges native to the waters off Florida and the Caribbean Sea. They superficially resemble staghorn corals.
Stevensine is a bromopyrrole alkaloid originally isolated from an unidentified Micronesian marine sponge, as well as a New Caledonian sponge, Pseudaxinyssa cantharella and Axinella corrugata. Total synthesis of stevensine has been achieved by Ying-zi Xu et al., and investigations into the biosynthetic origin has been explored by Paul Andrade et al. Understanding methods to synthesize stevensine and other similar compounds is an important step to accomplish, as marine sponges contain numerous biologically active metabolites that have been shown to function as anything from antitumor to antibacterial agents when tested for medicinal applications. Reasons for why marine sponges contain so many bio-active chemicals has been attributed to their sessile nature, and the need to produce chemical defenses to ensure survival. However, since many of these compounds naturally occur in small amounts, harvesting the sponges has in the past led to near-extinction of some species.
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).
Bacillus sonorensis is a species of bacteria with type strain L87-10T. Its genome has been sequenced.
Poribacteria are a candidate phylum of bacteria originally discovered in the microbiome of marine sponges (Porifera). Poribacteria are Gram-negative primarily aerobic mixotrophs with the ability for oxidative phosphorylation, glycolysis, and autotrophic carbon fixation via the Wood – Ljungdahl pathway. Poribacterial heterotrophy is characterised by an enriched set of glycoside hydrolases, uronic acid degradation, as well as several specific sulfatases. This heterotrophic repertoire of poribacteria was suggested to be involved in the degradation of the extracellular sponge host matrix.
Geodia barretti is a massive deep-sea sponge species found in the boreal waters of the North Atlantic Ocean, and is fairly common on the coasts of Norway and Sweden. It is a dominant species in boreal sponge grounds. Supported by morphology and molecular data, this species is classified in the family Geodiidae.
Micromonospora andamanensis is a Gram-positive bacterium from the genus Micromonospora which has been isolated from the sponge Xestospongia near Phuket, Thailand.
Gymnascella dankaliensis is a moderate to slow growing fungus commonly found in the soil of warmer climates. It is characterized by round yellow, orange or red-brown ascospores encircled by undifferentiated filaments. They have been found in ear, nail and skin infections. Their metabolites have been isolated and shown to have cytotoxic and anti-tumor properties.
Pseudoceratina is a genus of sponge within the family Pseudoceratinidae. They are characterized by possession of a dendritic fiber skeleton lacking laminar bark but containing pith. They have been found in a variety of habitats including the Great Barrier reef, the Red Sea, and Jamaica. Sponges of this genus have a microbiome known to produce a variety of chemicals that are used in pharmaceutical and anti-fouling activities. Notably, a species in this genus produces a chemical that is effective in inhibiting the migration of metastatic breast cancer cells.
Robertus Wilhelmus Maria (Rob) van Soest, born in 1946, is a Dutch marine biologist. He works at the Naturalis Biodiversity Center and is also affiliated with the University of Amsterdam. He co-authored with John N. A. Hooper Systema Porifera: A Guide to the Classification of Sponges, a standard reference for sponge classification.
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