Flagranone A

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Category Antibiotics
Catalog number BBF-00932
CAS
Molecular Weight 456.53
Molecular Formula C26H32O7

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Description

Flagranone A is a cyclohexenone oxide antibiotic produced by Duddingtonia flagrans. It has anti-gram-positive bacteria activity, and the MIC for both Bacillus subtilis and Staphylococcus aureus is 25 μg/mL.

Specification

IUPAC Name [6-[(2E,4E,6E)-1-acetyloxy-3,7,11-trimethyldodeca-2,4,6,10-tetraenyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate
Canonical SMILES CC(=CCCC(=CC=CC(=CC(C12C(O1)C(=O)C(=CC2=O)COC(=O)C)OC(=O)C)C)C)C
InChI InChI=1S/C26H32O7/c1-16(2)9-7-10-17(3)11-8-12-18(4)13-23(32-20(6)28)26-22(29)14-21(15-31-19(5)27)24(30)25(26)33-26/h8-9,11-14,23,25H,7,10,15H2,1-6H3/b12-8+,17-11+,18-13+
InChI Key PJRVHWMZLRRRMF-ZQEGAJDDSA-N

Properties

Appearance Yellow Oil
Antibiotic Activity Spectrum Gram-positive bacteria

Reference Reading

1. Structures of flagranones A, B and C, cyclohexenoxide antibiotics from the nematode-trapping fungus Duddingtonia flagrans
M G Anderson, R W Rickards, E Lacey J Antibiot (Tokyo). 1999 Nov;52(11):1023-8. doi: 10.7164/antibiotics.52.1023.
Spectroscopic data define the structures of the flagranones A (2), B (3) and C (4) from the nematode-trapping fungus Duddingtonia flagrans. These antibiotics are structurally related to the farnesylated cyclohexenoxides of the oligosporon group recently isolated from the nematode-trapping fungus Arthrobotrys oligospora, and show similar antimicrobial activity.
2. Molecular detection of Campylobacter spp. in drinking, recreational and environmental water supplies
J Moore, P Caldwell, B Millar Int J Hyg Environ Health. 2001 Nov;204(2-3):185-9. doi: 10.1078/1438-4639-00096.
A molecular detection assay was performed on 207 samples of drinking, recreational and environmental waters collected in Northern Ireland. The water sources which were PCR positive for Campylobacter spp. included 2/91 (2.2%) drinking water from domestic household taps, 5/57 (8.8%) swimming pool water, 1/23 (4.3%) lake water and 1/1 water from a jacuzzi. Extracted DNA from all water samples was amplified employing a sequence-specific PCR assay based on a 206 bp conserved region of the flagellin A-flagellin B (flaA/flaB) loci for Campylobacter jejuni, C. coli and C. lari. Given the physiological and cultural fragile nature of these species, no waters were cultured using conventional methods due to concern for reversion to non-culturability from time of collection to laboratory analysis. As this genus has been demonstrated to form a 'viable but non-culturable' (VBNC) form, failure to culture organisms conventionally from water does not necessarily equate to a negative result, hence molecular detection assays, especially those which can demonstrate cell viability, may be useful in helping to elucidate potential epidemiological sources and reservoirs of this organism, especially where water is suspected as being the vehicle of transmission.

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