Coniosetin

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Category Antibiotics
Catalog number BBF-01052
CAS
Molecular Weight 413.55
Molecular Formula C25H35NO4

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Description

It is produced by the strain of Coniochaeta ellipsoidea DSM 13856. It has activity against gram-positive bacteria, including clinical separation of multidrug resistant staphylococcus aureus and resistant to erythromycin streptococcus pneumoniae (MIC is 0.3-0.6 μg/mL), S. pyogenes, dung enterococcus and excrement enterococcus (MIC is 1.2-2.5 μg/mL). It has certain effect on yeast such as Candida albicans (MIC is 3.1 μg/mL). It has weak activity against gram-negative bacteria and other fungi.

Specification

Synonyms (5S)-5-[(S)-1-Hydroxyethyl]-3-[[1,2,4abeta,5,6,7,8,8aalpha-octahydro-1beta,3,6alpha-trimethyl-2alpha-[(1E,3E)-1,3-pentadienyl]naphthalene-1-yl]hydroxymethylene]pyrrolidine-2,4-dione
IUPAC Name (3E,5S)-3-[[(1S,2R,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dienyl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-hydroxymethylidene]-5-[(1S)-1-hydroxyethyl]pyrrolidine-2,4-dione
Canonical SMILES CC=CC=CC1C(=CC2CC(CCC2C1(C)C(=C3C(=O)C(NC3=O)C(C)O)O)C)C
InChI InChI=1S/C25H35NO4/c1-6-7-8-9-18-15(3)13-17-12-14(2)10-11-19(17)25(18,5)23(29)20-22(28)21(16(4)27)26-24(20)30/h6-9,13-14,16-19,21,27,29H,10-12H2,1-5H3,(H,26,30)/b7-6+,9-8+,23-20+/t14-,16+,17+,18-,19-,21+,25-/m1/s1
InChI Key ISHIUSZGAFLPLK-SPBZZWPFSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Fungi; Yeast
Solubility Soluble in Methanol

Reference Reading

1. Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856
Marian Paul Segeth, Alain Bonnefoy, Mark Brönstrup, Martin Knauf, Dietmar Schummer, Luigi Toti, László Vértesy, Marie-Cécile Wetzel-Raynal, Joachim Wink, Gerhard Seibert J Antibiot (Tokyo). 2003 Feb;56(2):114-22. doi: 10.7164/antibiotics.56.114.
The coprophilic ascomycete Coniochaeta ellipsoidea DSM 13856 forms the new antibiotic coniosetin (1) in surface cultures grown on a medium containing malt extract and oatmeal. The structure of the compound C25H35NO4, MW 413, was determined by 2D-NMR and mass spectrometric studies. Coniosetin belongs to the class of tetramic acids; it consists of a substituted aliphatic bicyclic ring system linked to a tetramic acid subunit through a carbonyl center. The absolute configuration was determined by measuring its circular dichroism spectrum and comparing the data with those of equisetin. Coniosetin has a pronounced antibacterial and antifungal action, inhibiting even multi drug-resistant strains of Staphylococcus aureus at a concentration of 0.3 microg/ml, though it is inactive against Gram-negative bacteria.

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