Chrysosporide

Last updated
Chrysosporide
Chrysosporide.svg
Chrysosporide 3D ball.png
Names
Other names
Cyclo(D-alanyl-L-leucyl-L-leucyl-D-leucyl-L-valyl)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C26H47N5O5/c1-13(2)10-18-23(33)29-19(11-14(3)4)24(34)30-20(12-15(5)6)25(35)31-21(16(7)8)26(36)27-17(9)22(32)28-18/h13-21H,10-12H2,1-9H3,(H,27,36)(H,28,32)(H,29,33)(H,30,34)(H,31,35)/t17-,18+,19+,20-,21+/m1/s1 Yes check.svgY
    Key: IJSHLVSQYSNTII-IFLJBQAJSA-N Yes check.svgY
  • InChI=1/C26H47N5O5/c1-13(2)10-18-23(33)29-19(11-14(3)4)24(34)30-20(12-15(5)6)25(35)31-21(16(7)8)26(36)27-17(9)22(32)28-18/h13-21H,10-12H2,1-9H3,(H,27,36)(H,28,32)(H,29,33)(H,30,34)(H,31,35)/t17-,18+,19+,20-,21+/m1/s1
    Key: IJSHLVSQYSNTII-IFLJBQAJBN
  • O=C1N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H]1CC(C)C)CC(C)C)C)C(C)C)CC(C)C
Properties
C26H47N5O5
Molar mass 509.692 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Chrysosporide is a cyclic pentapeptide. It is isolated from the mycoparasitic fungus Sepedonium chrysospermum , found in New Zealand. [1]

Related Research Articles

Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides which have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides.

<span class="mw-page-title-main">Hypha</span> Long, filamentous structure in fungi and Actinobacteria

A hypha is a long, branching, filamentous structure of a fungus, oomycete, or actinobacterium. In most fungi, hyphae are the main mode of vegetative growth, and are collectively called a mycelium.

Gordon Herriot Cunningham, CBE, FRS was the first New Zealand-based mycologist and plant pathologist. In 1936 he was appointed the first director of the DSIR Plant Diseases Division. Cunningham established the New Zealand Fungal Herbarium, and he published extensively on taxonomy of many fungal groups. He is regarded as the 'Father' of New Zealand mycology.

Nonribosomal peptides (NRP) are a class of peptide secondary metabolites, usually produced by microorganisms like bacteria and fungi. Nonribosomal peptides are also found in higher organisms, such as nudibranchs, but are thought to be made by bacteria inside these organisms. While there exist a wide range of peptides that are not synthesized by ribosomes, the term nonribosomal peptide typically refers to a very specific set of these as discussed in this article.

<span class="mw-page-title-main">Viomycin</span> Chemical compound

Viomycin is a member of the tuberactinomycin family, a group of nonribosomal peptide antibiotics exhibiting anti-tuberculosis activity. The tuberactinomycin family is an essential component in the drug cocktail currently used to fight infections of Mycobacterium tuberculosis. Viomycin was the first member of the tuberactinomycins to be isolated and identified, and was used to treat TB until it was replaced by the less toxic, but structurally related compound, capreomycin. The tuberactinomycins target bacterial ribosomes, binding RNA and disrupting bacterial protein synthesis and certain forms of RNA splicing. Viomycin is produced by the actinomycete Streptomyces puniceus.

<i>Metarhizium robertsii</i> Species of fungus

Metarhizium robertsii – formerly known as M. anisopliae, and even earlier as Entomophthora anisopliae (basionym) – is a fungus that grows naturally in soils throughout the world and causes disease in various insects by acting as a parasitoid. Ilya I. Mechnikov named it after the insect species from which it was originally isolated – the beetle Anisoplia austriaca. It is a mitosporic fungus with asexual reproduction, which was formerly classified in the form class Hyphomycetes of the phylum Deuteromycota.

<span class="mw-page-title-main">Archeocrypticidae</span> Family of beetles

The family Archeocrypticidae is a small group of beetles with no vernacular common name, though recent authors have coined the name cryptic fungus beetles. Adults and larvae seems to be saprophagous and are often found in plant litter. Worldwide, about 10 genera and 50 species are found, most species are pantropical. Enneboeus caseyi has been recorded from the American South, Central America, and Mexico. About 20 species are found in Australia, in the genera Enneboeus,Australenneboeus and Gondwanenneboeus,Archeocrypticus,Falsoplatydema, Nothenneboeus, Sivacrypticus and Wattianus. They are largely absent from the Palearctic and Nearctic regions.

A tetrapeptide is a peptide, classified as an oligopeptide, since it only consists of four amino acids joined by peptide bonds. Many tetrapeptides are pharmacologically active, often showing affinity and specificity for a variety of receptors in protein-protein signaling. Present in nature are both linear and cyclic tetrapeptides (CTPs), the latter of which mimics protein reverse turns which are often present on the surface of proteins and druggable targets. Tetrapeptides may be cyclized by a fourth peptide bond or other covalent bonds.

<i>Tylopilus felleus</i> Species of fungus

Tylopilus felleus, commonly known as the bitter bolete or the bitter tylopilus, is a fungus of the bolete family. Its distribution includes east Asia, Europe and eastern North America, extending south into Mexico and Central America. A mycorrhizal species, it grows in deciduous and coniferous woodland, often fruiting under beech and oak. Its fruit bodies have convex to flat caps that are some shade of brown, buff or tan and typically measure up to 15 cm (6 in) in diameter. The pore surface is initially white before turning pinkish with age. Like most boletes it lacks a ring and it may be distinguished from Boletus edulis and other similar species by its unusual pink pores and the prominent dark-brown net-like pattern on its stalk.

<i>Psilocybe weraroa</i> Species of fungus

Psilocybe weraroa is a secotioid fungus in the family Hymenogastraceae. It is endemic to New Zealand, where it grows in native forests from rotting wood and woody debris. Despite its pouch-like form this species is closely related to Psilocybe cyanescens and Psilocybe subaeruginosa. As a bluing member of the genus Psilocybe it contains the psychoactive compounds psilocin and psilocybin.

<span class="mw-page-title-main">Ulodidae</span> Family of beetles

The Ulodidae are a family of beetles belonging to Tenebrionoidea. They are native to the Southern Hemisphere, with species found in Australia, New Zealand, New Caledonia and Chile. Larvae and adults are generally found on dead wood or fungus associated with rotting wood, and are mycophagous. There are approximately 40 species in 16 genera.

<span class="mw-page-title-main">BQ-123</span> Chemical compound

BQ-123, also known as cyclo(-D-Trp-D-Asp-Pro-D-Val-Leu-), is a cyclic pentapeptide that was first isolated from a fermentation broth of Streptomyces misakiensis in 1991. NMR studies indicate that the polypeptide backbone consists of a type II beta turn and an inverse gamma turn. The side-chains adopt different orientations depending on the solvent used. The proline carbonyl oxygen atom located at the onset of a beta turn is a sodium ion binding site. It has a high affinity for sodium ions and can coordinate up to three of them. Studies have shown that BQ123 is effective in reversing Ischemia-induced acute renal failure, and it has been suggested that this might be because BQ123 increases reabsorption of sodium ions in the proximal tubule cells.

<span class="mw-page-title-main">Pentapeptide repeat</span>

Pentapeptide repeats are a family of sequence motifs found in multiple tandem copies in protein molecules. Pentapeptide repeat proteins are found in all species, but they are found in many copies in cyanobacterial genomes. The repeats were first identified by Black and colleagues in the hglK protein. The later Bateman et al. showed that a large family of related pentapeptide repeat proteins existed. The function of these repeats is uncertain in most proteins. However, in the MfpA protein a DNA gyrase inhibitor it has been suggested that the pentapeptide repeat structure mimics the structure of DNA. The repeats form a regular right handed four sided beta helix structure known as the Rfr-fold.

<i>Gyroporus cyanescens</i> Species of fungus

Gyroporus cyanescens, commonly known as the bluing bolete or the cornflower bolete, is a species of bolete fungus in the family Gyroporaceae. First described from France in 1788, the species is found in Asia, Australia, Europe, and eastern North America, where it grows on the ground in coniferous and mixed forests.

Mycetophagites is an extinct fungal genus of mycoparasitic in the order Hypocreales. A monotypic genus, it contains the single species Mycetophagites atrebora.

<i>Cyttaria gunnii</i> Species of fungus

Cyttaria gunnii, commonly known as the myrtle orange or beech orange, is an orange-white coloured and edible ascomycete fungus native to Australia and New Zealand. It is a specific parasite of myrtle beech trees.

Fellutanine A, B, C and D are bio-active diketopiperazine alkaloids isolated from the cultures of Penicillium fellutanum, that belongs to a class of naturally occurring 2,5-diketopiperazines. Originally they were thought to be based on the "trans" cyclic dipetide cyclo(L-Trp-D-Trp) but were later shown to be based on the "cis" cyclic dipetide cyclo(L-Trp-L-Trp). This was also confirmed when fellutanine A, B and C were isolated from Penicillium simplicissimum. The fellutanines A−C, are non-annulated analogues of cyclo(L-Trp-L-Trp), but unlike their diannulated analogue fellutanine D are not cytotoxic.

<i>Harrya chromapes</i> Species of fungus

Harrya chromapes, commonly known as the yellowfoot bolete or the chrome-footed bolete, is a species of bolete fungus in the family Boletaceae. The bolete is found in eastern North America, Costa Rica, and eastern Asia, where it grows on the ground, in a mycorrhizal association with deciduous and coniferous trees. Fruit bodies have smooth, rose-pink caps that are initially convex before flattening out. The pores on the cap undersurface are white, aging to a pale pink as the spores mature. The thick stipe has fine pink or reddish dots (scabers), and is white to pinkish but with a bright yellow base. The mushrooms are edible but are popular with insects, and so they are often infested with maggots.

<i>Hypomyces completus</i> Species of fungus

Hypomyces completus is a parasitic ascomycete in the order Hypocreales. The fungus grows on boletes, typically Suillus spraguei in North America, although the type collection was found on growing on Boletinus oxydabilis in Siberia. The color of its subiculum ranges from white initially to yellow-brown to greenish-brown to brown to black; the fruitbodies (perithecia) range from pale brown to dark brown to black. Spores measure 35–40 by 4–6 μm.

<span class="mw-page-title-main">Lolitrem B</span> Chemical compound

Lolitrem B is one of many toxins produced by a fungus called Epichloë festucae var. lolii), which grows in Lolium perenne. The fungus is symbiotic with the ryegrass; it doesn't harm the plant, and the toxins it produces kill insects that feed on ryegrass. Lolitrem B is one of these toxins, but it is also harmful to mammals. The shoots and flowers of infected ryegrass have especially high concentrations of lolitrem B, and when livestock eat too much of them, they get perennial ryegrass staggers. At low doses the animals have tremors, and at higher doses they stagger, and at higher yet doses the animals become paralyzed and die. The blood pressure of the animals also goes up. The effect of the lolitrem B comes on slowly and fades out slowly, as it is stored in fat after the ryegrass is eaten. The condition is especially common in New Zealand and Australia, and plant breeders there have been trying to develop strains of fungus that produce toxins only harmful to pests, and not to mammals.

References

  1. Mitova, Maya I.; Stuart, Blair G.; Cao, Grace H.; Blunt, John W.; Cole, Anthony L. J.; Munro, Murray H. G. (2006). "Chrysosporide, a cyclic pentapeptide from a New Zealand sample of the fungus Sepedonium chrysospermum". Journal of Natural Products. 69 (10): 1481–1484. doi:10.1021/np060137o. PMID   17067166.