Agelasines are 7,9-dialkylpurinium salts isolated from marine sponges. They are considered secondary metabolites. Their contribution to the sponge is assumed to be some sort of protection against microorganisms. At the present time a total of eleven 9-methyladeninium salts, agelasine A–I, epiagelasine C and agelin B, are known. All compounds carry a diterpenoid side chain in the adenine 7-position. The agelasines are closely related in structure with the agelasimines.
The Kornblum–DeLaMare rearrangement is a rearrangement reaction in organic chemistry in which a primary or secondary organic peroxide is converted to the corresponding ketone and alcohol under acid or base catalysis. The reaction is relevant as a tool in organic synthesis and is a key step in the biosynthesis of prostaglandins.
Cryptophycins are a family of macrolide molecules that are potent cytotoxins and have been studied for potential antiproliferative properties useful in developing chemotherapy. They are members of the depsipeptide family.
Ageliferin is a chemical compound produced by some sponges. It was first isolated from Caribbean and then Okinawan marine sponges in the genus Agelas. It often co-exists with the related compound sceptrin and other similar compounds. It has antibacterial properties and can cause biofilms to dissolve.
Callystatin A is a polyketide natural product from the leptomycin family of secondary metabolites. It was first isolated in 1997 from the marine sponge Callyspongia truncata which was collected from the Goto Islands in the Nagasaki Prefecture of Japan by the Kobayashi group. Since then its absolute configuration has been elucidated and callystatin A was discovered to have anti-fungal and anti-tumor activities with extreme potency against the human epidermoid carcinoma KB cells (IG50 = 10 pg/ml) and the mouse lymphocytic leukemia Ll210 cells (IG50 = 20 pg/ml).
Plakevulin A is a bio-active metabolite of the sea sponge Plakortis.
Callipeltin A and B are depsipeptides isolated from marine invertebrates. Preliminary research shows that they may have antiviral activity.
Suberedamines are chemical compounds that have been isolated from marine sponges in the genus Suberea. The compounds are brominated tyrosine dimer derivatives.
Stevensine is a bromopyrrole alkaloid originally isolated from an unidentified Micronesian marine sponge, as well as the known sponge species, 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.
Oroidin is a bromopyrrole alkaloid, originally isolated from marine sponges in the genus Agelas. It appears to have a wide range of biological activities, which makes Oroidin a potential drug candidate for various diseases. It also serves as chemical defense in marine sponges.
Cycloclavine is an ergot alkaloid. It was first isolated in 1969 from seeds of Ipomoea hildebrandtii vatke. The first total synthesis of (±)-cycloclavine was published in 2008 by Szántay. Further reports came from Wipf and Petronijevic, Cao and Brewer. In 2016, Wipf and McCabe completed an 8-step asymmetric synthesis of (–)-cycloclavine, and in 2018, they expanded this approach toward (+)-cycloclavine and a biological characterization of the binding profile of both enantiomers on 16 brain receptors. Natural (+)- and unnatural (–)-cycloclavine demonstrated significant stereospecificity and unique binding profiles in comparison to LSD, psilocin, and DMT. Differential 5-HT receptor affinities, as well as novel sigma-1 receptor properties, suggest potential future therapeutic opportunities of clavine alkaloid scaffolds.
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).
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. 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.
Onnamide A is a bioactive natural product found in Theonella swinhoei, a species of marine sponge whose genus is well known for yielding a diverse set of biologically active natural products, including the swinholides and polytheonamides. It bears structural similarities to the pederins, a family of compounds known to inhibit protein synthesis in eukaryotic cells. Onnamide A and its analogues have attracted academic interest due to their cytotoxicity and potential for combating the growth and proliferation of cancer cells.
Dysidea arenaria is a species of marine sponge (poriferan) found in the Pacific Ocean. It is a member of the order Dictyoceratida, one of two sponge orders that make up the keratose or "horny" sponges in which a mineral skeleton is absent and a skeleton of organic fibers is present instead.
Swinholides are dimeric 42 carbon-ring polyketides that exhibit a 2-fold axis of symmetry. Found mostly in the marine sponge Theonella, swinholides encompass cytotoxic and antifungal activities via disruption of the actin skeleton. Swinholides were first described in 1985 and the structure and stereochemistry were updated in 1989 and 1990, respectively. Thirteen swinholides have been described in the literature, including close structural compounds such as misakinolides/bistheonellides, ankaraholides, and hurgholide A It is suspected that symbiotic microbes that inhabit the sponges rather than the sponges themselves produce swinholides since the highest concentration of swinholides are found in the unicellular bacterial fraction of sponges and not in the sponge fraction or cyanobacteria fraction that also inhabit the sponges.
Luffariella is a genus of sea sponges in the family Thorectidae.
1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its condensed structural formula is [–(CH
2)3–O–O–].
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 reticulata that was 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.
Plakortis is a genus of marine sponges in the order Homosclerophorida, first described by Franz Eilhard Schulze in 1880.
