Cetoniacytone B

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Category Enzyme inhibitors
Catalog number BBF-00523
CAS
Molecular Weight 171.15
Molecular Formula C7H9NO4

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Description

It is produced by the strain of Actinomyces sp. Lu 9419. It can inhibit the growth of HEPG2 and MCF7 human tumor cell lines. GI50 is 4.4 ㎛ol/L.

Specification

Synonyms C21249; (1r,5s,6r)-4-amino-5-hydroxy-1-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
IUPAC Name (1R,5S,6R)-4-amino-5-hydroxy-1-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
Canonical SMILES C1=C(C(C2C(C1=O)(O2)CO)O)N
InChI InChI=1S/C7H9NO4/c8-3-1-4(10)7(2-9)6(12-7)5(3)11/h1,5-6,9,11H,2,8H2/t5-,6+,7-/m0/s1
InChI Key JKNVJVJEQNRUFL-XVMARJQXSA-N

Properties

Appearance Colorless Solid
Antibiotic Activity Spectrum neoplastics (Tumor)
Solubility Soluble in Methanol

Reference Reading

1. Structure and biosynthesis of cetoniacytone A, a cytotoxic aminocarba sugar produced by an endosymbiontic Actinomyces
Oliver Schlörke, Philipp Krastel, Ilka Müller, Isabel Usón, Konrad Dettner, Axel Zeeck J Antibiot (Tokyo). 2002 Jul;55(7):635-42. doi: 10.7164/antibiotics.55.635.
Cetoniacytone A (1) and some related minor components (2, 6, 7) were produced by Actinomyces sp. (strain Lu 9419), which was isolated from the intestines of a rose chafer (Cetonia aureata). The structures of the novel metabolites were established by detailed spectroscopic analysis. The absolute configuration of 1 was determined by X-ray analysis and derivatisation with chiral acids. 1 exhibits a significant cytotoxicity against selected tumor cell lines. The biosynthesis of 1 was studied by feeding 13C labelled precursors. The results suggest that the characteristic p-C7N skeleton of the aminocarba sugar is formed via the pentose phosphate pathway by cyclisation of a heptulose phosphate intermediate.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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