Identifiers | |
---|---|
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
| |
| |
Properties | |
C17H19BrN6O2 | |
Molar mass | 419.283 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Barettin is a brominated alkaloid made of a dehydrogenated brominated derivative of tryptophan linked by two peptide bonds to an arginine residue, forming a 2,5-diketopiperazine nucleus. [1] [2] It is a cyclic dipeptide.
Barettin is the major compound in the deep-sea sponge Geodia barretti . [3] It was isolated for the first time in 1986 by Göran Lidgren, Lars Bohlin and Jan Bergman at Uppsala University, Sweden [1] but the correct chemical structure was determined later in 2002. [2] Barettin is written with one 'r' because the authors misspelled Geodia barretti with one 'r' in the original paper. [1]
Barettin seems to show antioxidant and anti-inflammatory properties which could be used in treating diseases that affect the immune system and diseases that are caused by inflammation. [4] Atherosclerosis, a disease characterized by stiffening and a buildup of compounds in arteries, [5] may be prevented by barettin due to its anti-inflammatory properties. [4] The effects barettin has on inflammation may be due to its inhibitory properties on two protein kinases, receptor-interacting serine/threonine kinase 2 (RIPK2) and calcium/calmodulin-dependent protein kinase 1α (CAMK1α). [6]
In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH2−C6H5. Benzyl features a benzene ring attached to a methylene group group.
The Pauson–Khand (PK) reaction is a chemical reaction, described as a [2+2+1] cycloaddition. In it, an alkyne, an alkene and carbon monoxide combine into a α,β-cyclopentenone in the presence of a metal-carbonyl catalyst.
The Corey–Itsuno reduction, also known as the Corey–Bakshi–Shibata (CBS) reduction, is a chemical reaction in which a prochiral ketone is enantioselectively reduced to produce the corresponding chiral, non-racemic alcohol. The oxazaborolidine reagent which mediates the enantioselective reduction of ketones was previously developed by the laboratory of Itsuno and thus this transformation may more properly be called the Itsuno-Corey oxazaborolidine reduction.
Orellanine or orellanin is a mycotoxin found in a group of mushrooms known as the Orellani of the family Cortinariaceae. Structurally, it is a bipyridine N-oxide compound somewhat related to the herbicide diquat.
Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug during the 1910s. It is present in Hydrastis canadensis and other plants of the family Ranunculaceae.
Solenopsin is a lipophilic alkaloid with the molecular formula C17H35N found in the venom of fire ants (Solenopsis). It is considered the primary toxin in the venom and may be the component responsible for the cardiorespiratory failure in people who experience excessive fire ant stings.
Yuehchukene is a dimeric indole alkaloid natural product that possesses anti-fertility and estrogenic activities. Yuehchukene is isolated from the roots of Murraya paniculata and other species of the plant genus Murraya. Its natural abundance is in the range of 10-52 ppm.
Paxilline is a toxic, tremorgenic diterpene indole polycyclic alkaloid molecule produced by Penicillium paxilli which was first characterized in 1975. Paxilline is one of a class of tremorigenic mycotoxins, is a potassium channel blocker, and is potentially genotoxic.
Ianthella basta is a species of fan-shaped sea sponge in the class Demospongiae. It is also known as the elephant ear sponge, paper sponge, or scroll sponge.
Bakuchiol is a meroterpene in the class terpenophenol.
Callyspongia truncata is a species of marine sea sponge. Like all marine sponges, C. truncata is a member of phylum Porifera and is defined by its filter-feeding lifestyle and flagellated choanocytes, or collar cells, that allow for water movement and feeding. It is a species of demosponge and a member of Demospongiae, the largest class of sponges as well as the family Callyspongiidae. C. truncata is most well known for being the organism from which the polyketide Callystatin A was identified. Callystatin A is a polyketide natural product from the leptomycin family of antibiotics. It was first isolated in 1997 from this organism, which was collected from the Goto Islands in the Nagasaki Prefecture of Japan by the Kobayashi group. Recent studies have revealed numerous other bioactive compounds that have been found in this species.
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.
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.
Ellipticine is an alkaloid first extracted from trees of the species Ochrosia elliptica and Rauvolfia sandwicensis, which inhibits the enzyme topoisomerase II via intercalative binding to DNA.
The Mizoroki−Heck coupling of aryl halides and alkenes to form C(sp2)–C(sp2) bonds has become a staple transformation in organic synthesis, owing to its broad functional group compatibility and varied scope. In stark contrast, the palladium-catalyzed reductive Heck reaction has received considerably less attention, despite the fact that early reports of this reaction date back almost half a century. From the perspective of retrosynthetic logic, this transformation is highly enabling because it can forge alkyl–aryl linkages from widely available alkenes, rather than from the less accessible and/or more expensive alkyl halide or organometallic C(sp3) synthons that are needed in a classical aryl/alkyl cross-coupling.
Ploiarium is a genus of three species of woody plants in the family Bonnetiaceae. It is native to tropical forests and peat swamp forests in Southeast Asia including southern Indochina, Malay Peninsula, Sumatra, and Borneo. Species are generally slow growing with irregular flowering and fruiting cycles. Colonization of plants by arbuscular mycorrhizal fungi is known to improve growth and biomass.
Fascaplysin is a marine alkaloid based on 12H-pyrido[1–2-a:3,4-b′]diindole ring system. It was first isolated as a red pigment from the marine sponge Fascaplysinopsis bergquist collected in the South Pacific near Fiji in 1988. Fascaplysin possesses a broad range of in vitro biological activities including analgesic, antimicrobial, antifungal, antiviral, antimalarial, anti-angiogenic, and antiproliferative activity against numerous cancer cell lines.
Aszonalenin is an alkaloid which is produced by Neosartorya and Aspergillus species. Aszonalenin is a neurotoxin.
Fungerin is an antifungal alkaloid with the molecular formula C13H18N2O2 which is produced by Fusarium species.
Benzaldehyde oxime is an organic compound with the formula C7H7NO. Benzaldehyde oxime can be synthesized from benzaldehyde and hydroxylamine hydrochloride in presence of a base. The reaction at room temperature in methanol gives 9% E-isomer and 82% Z-isomer.