Sporidesmin is a mycotoxin produced by the fungus Pithomyces chartarum. It is a potent hepatotoxin that causes facial eczema in sheep and other livestock. Sporidesmin is a complex molecule with a unique structure that includes a disulfide bridge and a cyclopentane ring. Its synthesis has been studied extensively, revealing that it is produced via a complex biosynthetic pathway involving several enzymatic steps. The molecule's effects on animals are significant, with a primary focus on its hepatotoxic properties. Sporidesmin causes liver damage by disrupting cellular processes and inducing oxidative stress. The importance of studying sporidesmin lies in its impact on livestock health and its potential to cause human health problems. Research on sporidesmin focuses on understanding its biosynthetic pathways, toxicity mechanisms, and potential strategies for prevention and treatment. Sporidesmin is also a model compound for studying mycotoxin research.'
sporidesmin: RN given refers to sporidesmin; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
sporidesmin A : An organic heteropentacyclic compound that has formula C18H20ClN3O6S2, produced by the saprophyte fungus Pithomyces chartarum. It is a mycotoxin responsible for the hepatogenous photosensitisation disease facial eczema in ruminants. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 99596 |
| CHEBI ID | 9243 |
| SCHEMBL ID | 1096362 |
| MeSH ID | M0042263 |
| Synonym |
|---|
| sporidesmin a |
| sporidesmin benzene solvate |
| nsc-246152 |
| hydroxysporidesmin b |
| nsc 246152 |
| ccris 5323 |
| 3,11a-epidithio-11ah-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-dione, 9-chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-, (3-alpha,5a-alpha,10b-alpha,11-beta,11a-alpha)- |
| 1456-55-9 |
| sporidesmin |
| h70lc3h0rw , |
| unii-h70lc3h0rw |
| 3,11a-epidithio-11ah-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-dione, 9-chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-, (3.alpha.,5a.alpha.,10b.alpha.,11.beta.,11a.alpha.)- |
| sporidesmin a [mi] |
| SCHEMBL1096362 |
| CHEBI:9243 |
| DTXSID60929900 |
| 9-chloro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-2,3,5a,6,10b,11-hexahydro-3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione |
| 1378-20-7 |
| Q27108332 |
| (1r,2r,3s,11r,14r)-6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione |
| DTXSID001030686 |
Soridesmin is an epidithiopiperazine-2,5-dione (ETP) fungal toxin. It disrupts cellular functions likely via oxidative alteration of cysteine residues on key proteins.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Sporidesmin is an epidithiodioxopiperazine mycotoxin secreted by the saprophytic fungus Pithomyces chartarum. " | ( Zinc protection of HepG2 cells from sporidesmin toxicity does not require de novo gene transcription. Duncan, EJ; Phua, SH; Thompson, MP, 2005) | 2.05 |
| "Sporidesmin is an epidithiopiperazine-2,5-dione (ETP) fungal toxin that disrupts cellular functions likely via oxidative alteration of cysteine residues on key proteins." | ( Selective inactivation of glutaredoxin by sporidesmin and other epidithiopiperazinediones. Bala, A; Jao, SC; Jordan, TW; Mieyal, JJ; Srinivasan, U; Starke, DW, 2006) | 1.32 |
Sporidesmin has previously been shown to generate superoxide radical in vitro. The erythrocytic changes induced by the mycotoxin suggest that it is also capable of generating this radical intracellularly. Sporidesmin toxicity has not previously been reported in this species.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Sporidesmin toxicity has not previously been reported in this species." | ( Putative sporidesmin toxicity in an Eastern Grey kangaroo (Macropus giganteus). Hum, S, 2005) | 1.47 |
| "Sporidesmin has previously been shown to generate superoxide radical in vitro; the erythrocytic changes induced by the mycotoxin, which are characteristically produced by compounds which generate 'active oxygen' species, suggest that it is also capable of generating this radical intracellularly." | ( Studies on the mechanism of toxicity of the mycotoxin sporidesmin. 2--Evidence for intracellular generation of superoxide radical from sporidesmin. Munday, R, 1984) | 1.24 |
The chronic hepatotoxicity was consistent with exposure to sporidesmin, the toxic metabolite in the spores of the fungus Pithomyces chartarum. The hydroxyl radical may be the proximate agent responsible for the toxic effects.
| Excerpt | Reference | Relevance |
|---|---|---|
| " In view of the exceptional reactivity of the hydroxyl radical, this substance may be the proximate agent responsible for the toxic effects of sporidesmin." | ( Studies on the mechanism of toxicity of the mycotoxin, sporidesmin. V. Generation of hydroxyl radical by sporidesmin. Munday, R, 1987) | 0.72 |
| " This chronic hepatotoxicity was consistent with exposure to sporidesmin, the toxic metabolite in the spores of the fungus Pithomyces chartarum." | ( Putative sporidesmin toxicity in an Eastern Grey kangaroo (Macropus giganteus). Hum, S, 2005) | 0.99 |
| Role | Description |
|---|---|
| mycotoxin | Poisonous substance produced by fungi. |
| Wnt signalling activator | A substance that activates any of the Wnt signalling pathway, a group of signal transduction pathways made of proteins that pass signals from outside of a cell through cell surface receptors to the inside of the cell. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| organic heteropentacyclic compound | |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| organochlorine compound | An organochlorine compound is a compound containing at least one carbon-chlorine bond. |
| secondary alcohol | A secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it. |
| tertiary alcohol | A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it. |
| tertiary amino compound | A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups. |
| organic disulfide | Compounds of structure RSSR in which R and R' are organic groups. |
| diketone | A compound that contains two ketone functionalities. |
| cyclic ketone | |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 18 (42.86) | 18.7374 |
| 1990's | 8 (19.05) | 18.2507 |
| 2000's | 7 (16.67) | 29.6817 |
| 2010's | 5 (11.90) | 24.3611 |
| 2020's | 4 (9.52) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (29.13) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (4.76%) | 6.00% |
| Case Studies | 2 (4.76%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 38 (90.48%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||