| Identification | Back Directory | [Name]
(-)-Viriditoxin | [CAS]
1381782-08-6 | [Synonyms]
(?)-Viriditoxin
(-)-Viriditoxin
[6,6'-Bi-1H-naphtho[2,3-c]pyran]-3,3'-diacetic acid, 3,3',4,4'-tetrahydro-9,9',10,10'-tetrahydroxy-7,7'-dimethoxy-1,1'-dioxo-, 3,3'-dimethyl ester, (3S,3'S,6R)- | [Molecular Formula]
C34H30O14 | [MOL File]
1381782-08-6.mol | [Molecular Weight]
662.59 |
| Chemical Properties | Back Directory | [Boiling point ]
904.6±65.0 °C(Predicted) | [density ]
1.477±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: soluble; Ethanol: soluble | [form ]
A solid | [pka]
3.89±0.40(Predicted) |
| Hazard Information | Back Directory | [Description]
(−)-Viriditoxin is a mycotoxin originally isolated from A. viridinutans that has antibacterial and antiproliferative activity.1,2,3,4 It is active against methicillin-sensitive and -resistant S. aureus (MSSA and MRSA, respectively), tetracycline-sensitive and -resistant Staphylococcus, vancomycin-sensitive and -resistant Enterococcus, and penicillin-sensitive and -resistant S. pneumoniae (MICs = 2-32 μg/ml).2 (−)-Viriditoxin is also active against fish pathogens, including S. iniae and S. parauberis (MICs = 0.16-0.21 μg/ml).3 It inhibits polymerization and the GTPase activity of E. coli FtsZ, a tubulin-like GTPase involved in bacterial cell division (IC50s = 8.2 and 7 μg/ml, respectively).2 (−)-Viriditoxin inhibits proliferation of human DU145, LNCaP, and PC3 prostate cancer cells (IC50s = 5.36, 0.63, and 7.6 μM, respectively) .4 It is also toxic to mice (LD50 = 2.8 mg/kg, i.p.).5 | [Definition]
ChEBI: (M)-viriditoxin is a dimethyl 2,2'-(9,9',10,10'-tetrahydroxy-7,7'-dimethoxy-1,1'-dioxo-3,3',4,4'-tetrahydro-[6,6'-binaphtho[2,3-c]pyran]-3,3'-diyl)diacetate in which the the 3 and 3' positions (bearing the 2-methoxy-2-oxoethyl (CH2CO2Me) groups) both have S configuration, while the 6 and 6' positions (where the binaphthopyran units are linked) have Ra configuration (the M atropisomer). It has been isolated from the fungi Aspergillus viridinutans and the fungus Paecilomyces variotii derived from the inner tissues of the giant jellyfish Nemopilema nomurai. It has a role as a mycotoxin, an Aspergillus metabolite and an antibacterial agent. It is functionally related to a semiviriditoxin. | [References]
[1] D. WEISLEDER E. B L. Structure of viriditoxin, a toxic metabolite of Aspergillus viridi-nutans[J]. Tetrahedron Letters, 1971, 12 48: Pages 4705-4706. DOI: 10.1016/s0040-4039(01)97567-7
[2] JUN WANG. Discovery of a small molecule that inhibits cell division by blocking FtsZ, a novel therapeutic target of antibiotics.[J]. The Journal of Biological Chemistry, 2003, 278 45: 44424-44428. DOI: 10.1074/jbc.m307625200
[3] TAE HWAN NOH . Antibacterial activities of viriditoxin congeners and synthetic analogues against fish pathogens[J]. Bioorganic & Medicinal Chemistry Letters, 2017, 27 22: Pages 4970-4974. DOI: 10.1016/j.bmcl.2017.10.015
[4] SOMA KUNDU. Viriditoxin regulates apoptosis and autophagy via mitotic catastrophe and microtubule formation in human prostate cancer cells.[J]. International journal of oncology, 2014, 45 6: 2331-2340. DOI: 10.3892/ijo.2014.2659
[5] DAVID T. WONG Robert L H. Viriditoxin induces swelling and ATPase by activation of calcium transport in liver mitochondria[J]. Biochemical and biophysical research communications, 1976, 71 1: Pages 332-338. DOI: 10.1016/0006-291x(76)90287-4 |
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