Actiketal

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Category Antibiotics
Catalog number BBF-00024
CAS 133658-47-6
Molecular Weight 289.28
Molecular Formula C15H15NO5

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Description

Actiketal is a glutarimide antibiotic isolated from Streptomyces pulveraceus subsp. epiderstagenes. Actiketal can inhibit the incorporation of [3H] thymidine into Balb/MB cells activated by epidermal growth factor, with IC50 of 14.5 µmol/L, which is stronger than its analog Actiphenol (109.6 µmol/L), but better than epidermal statin (Epiderstatin) 3000 times weaker.

Specification

IUPAC Name 4-(2-hydroxy-5,7-dimethyl-3-oxo-1-benzofuran-2-yl)piperidine-2,6-dione
Canonical SMILES CC1=CC(=C2C(=C1)C(=O)C(O2)(C3CC(=O)NC(=O)C3)O)C
InChI InChI=1S/C15H15NO5/c1-7-3-8(2)13-10(4-7)14(19)15(20,21-13)9-5-11(17)16-12(18)6-9/h3-4,9,20H,5-6H2,1-2H3,(H,16,17,18)
InChI Key JGRHJZLSKWAAPV-UHFFFAOYSA-N

Properties

Appearance White Powder
Boiling Point 584.9°C at 760 mmHg
Melting Point 96-100°C
Density 1.423 g/cm3

Reference Reading

1. Synthesis of naturally derived bioactive compounds of agricultural interest
Hiromasa Kiyota Biosci Biotechnol Biochem. 2006 Feb;70(2):317-24. doi: 10.1271/bbb.70.317.
Synthetic studies on bioactive compounds are described, involving phytotoxins (tobacco wildfire disease toxin tabtoxinine-beta-lactam and rice blast disease toxin pyricuol) a glutarimide antibiotic (actiketal) black vomit toxin (gizzerosine) and marine products (antifeedant pteroenone and serinol compound didemniserinolipid).
2. Actiketal, a new member of the glutarimide antibiotics
T Sonoda, H Osada, J Uzawa, K Isono J Antibiot (Tokyo). 1991 Feb;44(2):160-3. doi: 10.7164/antibiotics.44.160.
A new glutarimide antibiotic named actiketal was isolated from the culture fluid of the epiderstatin-producing streptomycete, Streptomyces pulveraceus subsp. epiderstagenes. The IC50 of the antibiotic for inhibition of the incorporation of [3H]thymidine into epidermal growth factor-stimulated Balb/MK cells was 14.5 microM. The structure of this compound was determined by 1H and 13C NMR spectroscopic analyses using 1H-1H COSY, 13C-1H COSY, heteronuclear multiple-bond correlation spectroscopy, selective 13C-[1H] NOE's techniques.

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