Fumiquinazoline

Last updated
Fumiquinazoline
Fumiquinazoline C.png
Fumiquinazoline C
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
KEGG
PubChem CID
  • A:InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13-,18+,23-,24-/m0/s1
    Key: DQQCCKFZJNINST-VCPZKGNQSA-N
  • B:InChI=1S/C24H23N5O4/c1-12-19-27-16-9-5-3-7-14(16)22(32)28(19)18(20(30)25-12)11-24(33)15-8-4-6-10-17(15)29-21(31)13(2)26-23(24)29/h3-10,12-13,18,23,26,33H,11H2,1-2H3,(H,25,30)/t12-,13+,18-,23+,24+/m1/s1
    Key: DQQCCKFZJNINST-ZRCGILORSA-N
  • C:InChI=1S/C24H21N5O4/c1-12-19(31)28-16-10-6-4-8-14(16)24(22(28)25-12)11-17-18(30)27-23(2,33-24)21-26-15-9-5-3-7-13(15)20(32)29(17)21/h3-10,12,17,22,25H,11H2,1-2H3,(H,27,30)/t12-,17+,22-,23-,24-/m0/s1
    Key: POEYRUBMWIOMTB-LTQSKDJASA-N
  • D:InChI=1S/C24H21N5O4/c1-12-19(31)28-16-10-6-4-8-14(16)24(33)11-17-18(30)26-23(2,29(12)22(24)28)21-25-15-9-5-3-7-13(15)20(32)27(17)21/h3-10,12,17,22,33H,11H2,1-2H3,(H,26,30)/t12-,17+,22+,23-,24-/m0/s1
    Key: YYLAARMDRFESOL-CVAYNVNESA-N
  • E:InChI=1S/C25H25N5O5/c1-13-20(32)29-17-11-7-5-9-15(17)25(34,23(29)26-13)12-18-19(31)28-24(2,35-3)22-27-16-10-6-4-8-14(16)21(33)30(18)22/h4-11,13,18,23,26,34H,12H2,1-3H3,(H,28,31)/t13-,18+,23-,24+,25-/m0/s1
    Key: MUUBSMIWCJLEGK-HBLJGDDGSA-N
  • A:C[C@H]1C2=NC3=CC=CC=C3C(=O)N2[C@@H](C(=O)N1)C[C@]4([C@H]5N[C@H](C(=O)N5C6=CC=CC=C64)C)O
  • B:C[C@@H]1C2=NC3=CC=CC=C3C(=O)N2[C@@H](C(=O)N1)C[C@]4([C@H]5N[C@H](C(=O)N5C6=CC=CC=C64)C)O
  • C:C[C@H]1C(=O)N2[C@H](N1)[C@]3(C[C@@H]4C(=O)N[C@@](O3)(C5=NC6=CC=CC=C6C(=O)N45)C)C7=CC=CC=C72
  • D:C[C@H]1C(=O)N2[C@@H]3N1[C@]4(C5=NC6=CC=CC=C6C(=O)N5[C@H](C[C@@]3(C7=CC=CC=C72)O)C(=O)N4)C
  • E:C[C@H]1C(=O)N2[C@H](N1)[C@@](C3=CC=CC=C32)(C[C@@H]4C(=O)N[C@](C5=NC6=CC=CC=C6C(=O)N45)(C)OC)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Fumiquinazolines are bio-active isolates of Aspergillus . [2] [3]

Contents

Related Research Articles

<i>Aspergillus fumigatus</i> Species of fungus

Aspergillus fumigatus is a species of fungus in the genus Aspergillus, and is one of the most common Aspergillus species to cause disease in individuals with an immunodeficiency.

<i>Aspergillus</i> Genus of fungi

Aspergillus is a genus consisting of several hundred mold species found in various climates worldwide.

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

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics. Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite that is one of the most abundantly produced metabolites in human invasive Aspergillosis (IA).

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

Spirotryprostatin B is an indolic alkaloid found in the Aspergillus fumigatus fungus that belongs to a class of naturally occurring 2,5-diketopiperazines. Spirotryprostatin B and several other indolic alkaloids have been found to have anti-mitotic properties, and as such they have become of great interest as anti-cancer drugs. Because of this, the total syntheses of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.

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

Spirotryprostatin A is an indolic alkaloid from the 2,5-Diketopiperazine class of natural products found in the Aspergillus fumigatus fungus. Spirotryprostatin A and several other indolic alkaloids have been found to have anti-mitotic properties, and as such they have become of great interest as anti-cancer drugs. Because of this, the total syntheses of these compounds is a major pursuit of organic chemists, and a number of different syntheses have been published in the chemical literature.

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

Yuremamine is a phytoindole alkaloid which was isolated from the bark of Mimosa tenuiflora in 2005, and erroneously assigned a pyrrolo[1,2-a]indole structure that was thought to represent a new class of indole alkaloids. However, in 2015, the bioinspired total synthesis of yuremamine revealed its structure to be a flavonoid derivative. It was also noted in the original isolation of yuremamine that the alkaloid occurs naturally as a purple solid, but total synthesis revealed that yuremamine as a free base is colorless, and the formation of a trifluoroacetate salt during HPLC purification is what led to the purple appearance.

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

Ergocryptine is an ergopeptine and one of the ergoline alkaloids. It is isolated from ergot or fermentation broth and it serves as starting material for the production of bromocriptine. Two isomers of ergocryptine exist, α-ergocryptine and β-ergocryptine. The beta differs from the alpha form only in the position of a single methyl group, which is a consequence of the biosynthesis in which the proteinogenic amino acid leucine is replaced by isoleucine. β-Ergocryptine was first identified in 1967 by Albert Hofmann. Ergot from different sources have different ratios of the two isomers.

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

Brevianamides are indole alkaloids that belong to a class of naturally occurring 2,5-diketopiperazines produced as secondary metabolites of fungi in the genus Penicillium and Aspergillus. Structurally similar to paraherquamides, they are a small class compounds that contain a bicyclo[2.2.2]diazoctane ring system. One of the major secondary metabolites in Penicillium spores, they are responsible for inflammatory response in lung cells.

Aspergillus sydowii is a pathogenic fungus that causes several diseases in humans. It has been implicated in the death of sea fan corals in the Caribbean Sea.

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

Aspergillic acid is an organic chemical compound with the molecular formula C12H20N2O2. It has a pale yellow crystalline appearance. Aspergillic acid is most commonly known as an antibiotic and antifungal agent that is derived from certain strains of the fungus Aspergillus flavus.

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

Sorbicillactone A is a bio-active isolate of a sponge-derived fungus.

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

Notoamides are bio-active isolates of marine Aspergillus.

<span class="mw-page-title-main">Versicolamide B</span>

(-)-Versicolamide B and (+)-Versicolamide B are spiroindole alkaloids isolated from the fungus Aspergillus that belong to a class of naturally occurring 2,5-diketopiperazines. The versicolamides are structurally complex spiro-cyclized versions of prenylated cyclo(L-Trp-L-Pro) derivatives which possess a unique spiro-fusion to a pyrrolidine at the 3-position of the oxindole core together with the bicyclo[2.2.2]diazaoctane ring system. While (-)-versicolamide B was isolated from the marine fungus Aspergillus sp. the enantiomer (+)-versicolamide B was isolated from the terrestrial fungi Aspergillus versicolor NRRL. The total asymmetric syntheses of both enantiomers have been achieved and the implications of their biosynthesis have been investigated.

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

Pseurotin A is a secondary metabolite of Aspergillus.

<span class="mw-page-title-main">14-Norpseurotin A</span> Chemical compound

14-Norpseurotin A is an alkaloid and a bio-active metabolite of Aspergillus, featuring an oxa-spiro-lactam core.

Fungal isolates have been researched for decades. Because fungi often exist in thin mycelial monolayers, with no protective shell, immune system, and limited mobility, they have developed the ability to synthesize a variety of unusual compounds for survival. Researchers have discovered fungal isolates with anticancer, antimicrobial, immunomodulatory, and other bio-active properties. The first statins, β-Lactam antibiotics, as well as a few important antifungals, were discovered in fungi.

Penicillium vinaceum is an anamorph species of fungus in the genus Penicillium which produces penicillivinacine, vinaxanthone and citromycetin.

Streptomyces chartreusis is a bacterium species from the genus of Streptomyces which has been isolated from soil in Africa. Streptomyces chartreusis produces N-deacyltunicamycin, elsamicin A, aminoacylase and chartreusin.

Aspergillus viridinutans is a species of fungus in the genus Aspergillus. The species was first isolated in Frankston, Victoria, Australia and described in 1954. It is from the Fumigati section of Aspergillus. Several fungi from this section produce heat-resistant ascospores, and the isolates from this section are frequently obtained from locations where natural fires have previously occurred. A. viridinutans has been identified as the cause of chronic aspergillosis. The mycotoxin viriditoxin was first identified in A. viridinutans. A draft genome sequence of the strain derived from the original species description has been generated.

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

Conofoline is an alkaloid of the vinca alkaloid class which is closely related to conophylline. It is found in the leaves of some species in the genus Tabernaemontana, including Tabernaemontana divaricata, and in Ervatamia peduncularis.

References

  1. 1 2 3 4 Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (26 January 2010). Dictionary of Alkaloids with CD-ROM. CRC Press. p. 793. ISBN   978-1-4200-7770-4.
  2. ↑ Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (2010). Dictionary of Alkaloids, Second Edition with CD-ROM. CRC Press. ISBN   9781420077704.
  3. ↑ Walsh, Christopher T.; Tang, Yi (2017). Natural Product Biosynthesis: Chemical Logic and Enzymatic Machinery. Royal Society of Chemistry. ISBN   9781788010764.

Further reading

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