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83912-90-7

83912-90-7 Structure

83912-90-7 Structure
IdentificationBack Directory
[Name]

GLIOVIRIN
[CAS]

83912-90-7
[Synonyms]

GLIOVIRIN
(1aS,12aS)-4,4aβ,8,9-Tetrahydro-4β-hydroxy-9β-(2-hydroxy-3,4-dimethoxyphenyl)-12H-8α,11aα-(iminomethano)-1aαH,7H-[1,2,4]dithiazepino[4,3-b]oxireno[e][1,2]benzoxazine-7,13-dione
12H-8,11a-(Iminomethano)-1aH,7H-[1,2,4]dithiazepino[4,3-b]oxireno[e][1,2]benzoxazine-7,13-dione, 4,4a,8,9-tetrahydro-4-hydroxy-9-(2-hydroxy-3,4-dimethoxyphenyl)-, (1aS,4R,4aS,8S,9R,11aR,12aS)-
(1AS-(1AALPHA,4BETA,4ABETA,8ALPHA,9BETA,11AALPHA,12AR*))-4,4A,8,9-TETRAHYDRO-4-HYDROXY-9-(2-HYDROXY-3,4-DIMETHOXYPHENYL)-12H-8,11-(IMINOMETHANO)-1AH,7H-(1,2,4)DITHIAZEPINO(4,3-B)OXIRENO(E)(1,2)BENZOXAZINE-7,13-DIONE
[Molecular Formula]

C20H20N2O8S2
[MDL Number]

MFCD08274579
[MOL File]

83912-90-7.mol
[Molecular Weight]

480.51
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

DMSO: soluble,Ethanol: soluble,Methanol: soluble
[form ]

A solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P271
[HS Code ]

2941900000
Hazard InformationBack Directory
[Description]

Gliovirin is a fungal metabolite that has been found in T. harzianum and has fungicidal, antimicrobial and anti-inflammatory activities. It is active against the plant pathogenic fungus P. ultimum (MIC = 60 ng/ml) and the parasite T. brucei brucei (IC50 = 90 ng/ml), but has no effect on the plant pathogenic fungi R. solani, P. omnivorum, T. basicola, R. arrhizus, and V. dahliae or the bacteria B. thuringiensis, P. fluorescens, and X. malvacearum when used at concentrations up to 1,000 ng/ml. Gliovirin decreases phorbol 12-myristate 13-acetate (TPA)- and ionomycin-induced increased expression of COX-2 (IC50 = 1 μM) and protein levels of IL-2 in Jurkat cells (IC50 = 5.2 μM).
[References]

[1] JAN RETHER. Inhibition of inducible tumor necrosis factor-alpha expression by the fungal epipolythiodiketopiperazine gliovirin.[J]. Biological Chemistry, 2007, 388 6: 627-637. DOI: 10.1515/bc.2007.066
[2] HOWELL C R, STIPANOVIC R. Gliovirin, a new antibiotic from Gliocladium virens, and its role in the biological control of Pythium ultimum[C]//57 1. 1983: 0. DOI: 10.1139/m83-053
[3] MASATO IWATSUKI. In vitro antitrypanosomal activity of 12 low-molecular-weight antibiotics and observations of structure/activity relationships[J]. Journal of Antibiotics, 2010, 63 10: 619-622. DOI: 10.1038/ja.2010.99
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