Grahamimycin B

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Grahamimycin B
Category Antibiotics
Catalog number BBF-01276
CAS 75979-94-1
Molecular Weight 300.30
Molecular Formula C14H20O7

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Description

It is produced by the strain of Cytospora sp. W. F. P. L. 13A (ATCC20502). It has weak activity against gram-positive bacteria, negative bacteria, cyanobacteria and green algae.

Specification

Synonyms 1,7-Dioxacyclotetradec-3-ene-2,8,11-trione,9,12-dihydroxy-6,14-dimethyl-, (6R-(3E,6R*,9R*,12R*,14S*))-
IUPAC Name (3Z,6R,9R,12R,14S)-9,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradec-3-ene-2,8,11-trione
Canonical SMILES CC1CC=CC(=O)OC(CC(C(=O)CC(C(=O)O1)O)O)C
InChI InChI=1S/C14H20O7/c1-8-4-3-5-13(18)20-9(2)6-10(15)11(16)7-12(17)14(19)21-8/h3,5,8-10,12,15,17H,4,6-7H2,1-2H3/b5-3-/t8-,9+,10-,12-/m1/s1
InChI Key UPKYFPVASUJJTL-NZRRVRCFSA-N

Properties

Appearance Colorless Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 584.3 °C at 760 mmHg
Melting Point 126-127 °C
Density 1.214 g/cm3
Solubility Soluble in Chloroform

Reference Reading

1. Grahamimycins: antibiotics from Cytospora sp. Ehrenb. W.F.P.L. 13A
S Gurusiddaiah, R C Ronald Antimicrob Agents Chemother. 1981 Jan;19(1):153-65. doi: 10.1128/AAC.19.1.153.
Aerobic fermentation of cultures of Cytospora sp. Ehrenb. W.F.P.L. 13A produces a group of novel, broad-spectrum, dilactone, macrocyclic antibiotics. These compounds, named grahamimycins, were isolated from the culture medium by extraction with organic solvents and separated by chromatography. Three active components have been obtained in crystalline form and have been designated grahamimycins A, A1, and B. The most active of these, grahamimycin A, exhibited activity against 36 species of bacteria, 8 species of blue-green algae (cyanobacteria), and 2 species of green algae, and antifungal activity against 5 fungi. Studies on the growth of the Cytospora with respect to formation of antibiotic activity, and the isolation, characterization, and structure elucidation of the grahamimycins are described. These studies indicate that the grahamimycins are distinct from other known antibiotics and represent a new class of antibiotic structures.

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