Gunacin

Gunacin

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Gunacin
Category Antibiotics
Catalog number BBF-01300
CAS 73341-70-5
Molecular Weight 348.33
Molecular Formula C17H16O8
Purity 95%

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Description

It is produced by the strain of Ustilago sp. It is a quinone antibiotic. It has strong activity against gram-positive bacteria, negative bacteria and mycoplasma.

Specification

Synonyms 2H-Naphtho(2,3-b)pyran-5,10-dione, 3,4-dihydro-4-(acetyloxy)-3,6-dihydroxy-8-methoxy-2-methyl-
IUPAC Name (3,6-dihydroxy-8-methoxy-2-methyl-5,10-dioxo-3,4-dihydro-2H-benzo[g]chromen-4-yl) acetate
Canonical SMILES CC1C(C(C2=C(O1)C(=O)C3=C(C2=O)C(=CC(=C3)OC)O)OC(=O)C)O
InChI InChI=1S/C17H16O8/c1-6-13(20)16(25-7(2)18)12-15(22)11-9(14(21)17(12)24-6)4-8(23-3)5-10(11)19/h4-6,13,16,19-20H,1-3H3
InChI Key GEQDLVXKRXTSSY-UHFFFAOYSA-N

Properties

Appearance Orange Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Mycoplasma
Boiling Point 595.8 °C at 760 mmHg
Density 1.51 g/cm3
Solubility Soluble in Ethanol

Reference Reading

1. Gunacin, a new quinone antibiotic from Ustilago sp
R G Werner, K R Appel, W M Merk J Antibiot (Tokyo). 1979 Nov;32(11):1104-11. doi: 10.7164/antibiotics.32.1104.
In a screening program for antibiotics which were antagonized by cysteine, a strain, which was characterized as Ustilago sp., was found to produce a new quinone antibiotic, gunacin. The molecular weight M+ = 348.084 determined by mass spectroscopy, corresponds to a molecular formula of C17H16O8. Further spectroscopic data prove that gunacin is a new antibiotic. The antibiotic possesses a good inhibitory effect against mycoplasmas and Gram-positive bacteria including multi-resistant strains. It also possesses a weak activity against Gram-negative bacteria with the exception of Proteus vulgaris, which is more strongly inhibited. The main activity against fungi is found against Trichophyton mentagrophytes. Gunacin shows an inhibition of the DNA synthesis in vivo, is antagonized by mercapto compounds and possesses an acute toxicity of LD50 = 16 mg/kg i.p. and LD50 = 12 mg/kg i.v. in mice. Against HeLa-cell the antibiotic shows an ED50 = 12.11 microgram/ml. Thirty five microgram/ml of gunacin induces 1,063 interferon units.

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