Epolactaene

Last updated
Epolactaene
Epolactaene Structure.svg
Names
IUPAC name
Methyl (2E,3E,5E,9E)-2-ethylidene-11-[(1R,5R)-4-hydroxy-4-methyl-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,10-dimethyl-11-oxoundeca-3,5,9-trienoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C21H27NO6/c1-6-15(17(24)27-5)12-13(2)10-8-7-9-11-14(3)16(23)21-18(28-21)20(4,26)22-19(21)25/h6,8,10-12,18,26H,7,9H2,1-5H3,(H,22,25)/b10-8+,13-12+,14-11+,15-6+/t18-,20?,21-/m0/s1
    Key: GFRNQYUCUNYIEN-ZLXMTJSISA-N
  • C/C=C(\C=C(/C)\C=C\CC/C=C(\C)/C(=O)[C@@]12[C@@H](O1)C(NC2=O)(C)O)/C(=O)OC
Properties
C21H27NO6
Molar mass 389.448 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Epolactaene is a neuritogenic fungal isolate. [1] [2] [3]

Related Research Articles

Antibiotic Antimicrobial substance active against bacteria

An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the common cold or influenza; drugs which inhibit viruses are termed antiviral drugs or antivirals rather than antibiotics.

Lantibiotics are a class of polycyclic peptide antibiotics that contain the characteristic thioether amino acids lanthionine or methyllanthionine, as well as the unsaturated amino acids dehydroalanine, and 2-aminoisobutyric acid. They belong to ribosomally synthesized and post-translationally modified peptides.

<i>beta</i>-Carboline Chemical compound also known as norharmane

β-Carboline (9H-pyrido[3,4-b]indole), also known as norharmane, is a nitrogen containing heterocycle. It is also the prototype of a class of indole alkaloid compounds known as β-carbolines.

Fumagillin

Fumagillin is a complex biomolecule and used as an antimicrobial agent. It was isolated in 1949 from the microbial organism Aspergillus fumigatus.

Topoisomerase inhibitors are chemical compounds that block the action of topoisomerases, which are broken into two broad subtypes: type I topoisomerases (TopI) and type II topoisomerases (TopII). Topoisomerase plays important roles in cellular reproduction and DNA organization, as they mediate the cleavage of single and double stranded DNA to relax supercoils, untangle catenanes, and condense chromosomes in eukaryotic cells. Topoisomerase inhibitors influence these essential cellular processes. Some topoisomerase inhibitors prevent topoisomerases from performing DNA strand breaks while others, deemed topoisomerase poisons, associate with topoisomerase-DNA complexes and prevent the re-ligation step of the topoisomerase mechanism. These topoisomerase-DNA-inhibitor complexes are cytotoxic agents, as the un-repaired single and double stranded DNA breaks that they cause can lead to apoptosis and cell death. Because of this ability to induce apoptosis, topoisomerase inhibitors have gained interest as therapeutics against infectious and cancerous cells.

2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring.

The HL-60 cell line is a human leukemia cell line that has been used for laboratory research on blood cell formation and physiology. HL-60 proliferates continuously in suspension culture in nutrient and antibiotic chemicals. The doubling time is about 36–48 hours. The cell line was derived from a 36-year-old woman who was originally reported to have acute promyelocytic leukemia at the MD Anderson Cancer Center. HL-60 cells predominantly show neutrophilic promyelocytic morphology. Subsequent evaluation, including the karyotype that showed absence of the defining t(15;17) translocation, concluded that HL-60 cells are from a case of AML FAB-M2.

TAL1

T-cell acute lymphocytic leukemia protein 1 is a protein that in humans is encoded by the TAL1 gene.

LIMK2

LIM domain kinase 2 is an enzyme that in humans is encoded by the LIMK2 gene.

ING2

Inhibitor of growth protein 2 is a protein that in humans is encoded by the ING2 gene.

Dipeptidase 1

Dipeptidase 1 (DPEP1), or renal dipeptidase, is a membrane-bound glycoprotein responsible for hydrolyzing dipeptides. It is found in the microsomal fraction of the procine kidney cortex. It exists as a disulfide-linked homodimer that is glygosylphosphatidylinositol (GPI)-anchored to the renal brush border of the kidney. The active site on each homodimer is made up of a barrel subunit with binuclear zinc ions that are bridged by the Gly125 side-chain located at the bottom of the barrel.

ZNF638

Zinc finger protein 638 is a protein that in humans is encoded by the ZNF638 gene.

Collagen, type XXV, alpha 1

Collagen alpha-1(XXV) chain is a protein that in humans is encoded by the COL25A1 gene.

Indolocarbazole

Indolocarbazoles (ICZs) are a class of compounds that are under current study due to their potential as anti-cancer drugs and the prospective number of derivatives and uses found from the basic backbone alone. First isolated in 1977, a wide range of structures and derivatives have been found or developed throughout the world. Due to the extensive number of structures available, this review will focus on the more important groups here while covering their occurrence, biological activity, biosynthesis, and laboratory synthesis.

Enterolactone

Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

Naphthomycins are a group of closely related antimicrobial chemical compounds isolated from Streptomyces. They are considered a subclass of ansamycins.

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.

Sponge isolates

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).

Titanocene Y

Titanocene Y also known as bis[(p-methoxybenzyl)cyclopentadienyl]titanium(IV) dichloride or dichloridobis(η5- cyclopentadienyl)titanium is an organotitanium compound that has been investigated for use as an anticancer drug.

Cytotrienin A

Cytotrienin A is a secondary metabolite isolated from Streptomyces sp. RK95-74 isolated from soil in Japan in 1997. Cyt A is an ansamycin. Cytotrienin A induces apoptosis on HL-60 cells, as well as inhibiting translation in eukaryotes by inhibiting eukaryotic elongation factor 1A (eEF1A), which can act as an oncogene. These functions lead to the potential of the microbial metabolite acting as an anticancer agent, specifically for blood cancers, as it has proved to be more effective with leukemic cell lines. Cyt A is thought to induce apoptosis by activating c-Jun N-terminal Kinase (JNK), p38 mitogen-activated protein kinase (MAPK), and p36 myelin basic protein (MBP) kinase.

References

  1. Kakeya, H; Takahashi, I; Okada, G; Isono, K; Osada, H (1995). "Epolactaene, a novel neuritogenic compound in human neuroblastoma cells, produced by a marine fungus". The Journal of Antibiotics. 48 (7): 733–5. doi: 10.7164/antibiotics.48.733 . PMID   7649877.
  2. Nagumo Y, Kakeya H, Shoji M, Hayashi Y, Dohmae N, Osada H (2005). "Epolactaene binds human Hsp60 Cys442 resulting in the inhibition of chaperone activity". Biochem J. 387 (Pt 3): 835–40. doi:10.1042/BJ20041355. PMC   1135015 . PMID   15603555.
  3. Mizushina Y, Kuramochi K, Ikawa H, Kuriyama I, Shimazaki N, Takemura M, et al. (2005). "Structural analysis of epolactaene derivatives as DNA polymerase inhibitors and anti-inflammatory compounds". Int J Mol Med. 15 (5): 785–93. doi:10.3892/ijmm.15.5.785. PMID   15806299.