A fungal metabolite
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Gliovirin

Item No. 28583

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1aS,4R,4aS,8S,9R,11aR,12aS)-4,4a,8,9-tetrahydro-4-hydroxy-9-(2-hydroxy-3,4-dimethoxyphenyl)-12H-8,11a-(iminomethano)-1aH,7H-[1,2,4]dithiazepino[4,3-b]oxireno[e][1,2]benzoxazine-7,13-dione
CAS Number
83912-90-7
Molecular Formula
C20H20N2O8S2
Formula Weight
480.5
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleEthanol: solubleMethanol: soluble
SMILES
[H][C@@]([C@H](SS[C@]12C[C@]34O[C@H]3C=C[C@H]([C@]54[H])O)C6=CC=C(C(OC)=C6O)OC)(C(N2O5)=O)NC1=O
InChi Code
InChI=1S/C20H20N2O8S2/c1-27-10-5-3-8(13(24)14(10)28-2)15-12-17(25)22-20(32-31-15,18(26)21-12)7-19-11(29-19)6-4-9(23)16(19)30-22/h3-6,9,11-12,15-16,23-24H,7H2,1-2H3,(H,21,26)/t9-,11+,12-,15-,16+,19+,20-/m1/s1
InChi Key
VZUFPCHAVLFFAY-GGLVFAGASA-N
Origin
Fungi/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Gliovirin is a fungal metabolite that has been found in T. harzianum and has fungicidal, antimicrobial and anti-inflammatory activities.1 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.2,3 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).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rether, J., Serwe, A., Anke, T., et al. Inhibition of inducible tumor necrosis factor-α expression by the fungal epipolythiodiketopiperazine gliovirin. Biol. Chem. 388(6), 627-637 (2007).

    2. Howell, C.R., and Stipanovic, R.D. Gliovirin, a new antibiotic from Gliocladium virens, and its role in the biological control of Pythium ultimum. Can. J. Microbiol. 29(3), 321-324 (1983).

    3. Iwatsuki, M., Otoguro, K., Ishiyama, A., et al. In vitro antitrypanosomal activity of 12 low-molecular-weight antibiotics and observations of structure/activity relationships. J. Antibiot. (Tokyo) 63(10), 619-622 (2010).