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Epoxyquinomicin D

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Category Others
Catalog number BBF-00859
CAS 200496-86-2
Molecular Weight 325.70
Molecular Formula C14H12ClNO6

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Product Description

Epoxyquinomicin D is the active substanceproduced by Amycolatopsis sp. MK299-95F4.

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IUPAC Name 3-chloro-2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
Canonical SMILES C1=CC(=C(C(=C1)Cl)O)C(=O)NC2=CC(=O)C3(C(C2O)O3)CO
InChI InChI=1S/C14H12ClNO6/c15-7-3-1-2-6(10(7)19)13(21)16-8-4-9(18)14(5-17)12(22-14)11(8)20/h1-4,11-12,17,19-20H,5H2,(H,16,21)/t11-,12+,14-/m0/s1
InChI Key CQWDZNQKJPNNJB-SCRDCRAPSA-N
Appearance White Powder
Melting Point 163-168°C
Solubility Soluble in Methanol, methyl ether, ethyl acetate
1. Epoxyquinomicins A, B, C and D, new antibiotics from Amycolatopsis. II. Effect on type II collagen-induced arthritis in mice
N Matsumoto, H Iinuma, T Sawa, T Takeuchi, S Hirano, T Yoshioka, M Ishizuka J Antibiot (Tokyo). 1997 Nov;50(11):906-11. doi: 10.7164/antibiotics.50.906.
The anti-arthritic effects of epoxyquinomicins on type II collagen-induced arthritis in DBA/1J mice were examined. Prophylactic treatment with epoxyquinomicins A, B, C and D (1-4 mg/kg) had potent inhibitory effects on type II collagen-induced arthritis. In contrast to nonsteroidal anti-inflammatory drugs (NSAIDs), epoxyquinomicin C (1-30 mg/kg) had neither an anti-inflammatory effect on carrageenan-induced paw edema in rats nor an analgesic effect on acetic acid-induced writhing in mice. These results suggest that the mode of action of epoxyquinomicins is different from that of NSAIDs and that epoxyquinomicins may become useful drugs for the treatment of rheumatoid arthritis.
2. Epoxyquinomicins A, B, C and D, new antibiotics from Amycolatopsis. III. Physico-chemical properties and structure determination
N Matsumoto, T Tsuchida, R Sawa, H Iinuma, H Nakamura, H Naganawa, T Sawa, T Takeuchi J Antibiot (Tokyo). 1997 Nov;50(11):912-5. doi: 10.7164/antibiotics.50.912.
The structures of epoxyquinomicins A (1), B (2), C (3) and D (4) were determined by spectroscopic studies. Compound 1 was determined to be (5R,6S)-2-(3-chloro-2-hydroxybenzoylamino)-5-hydroxymethyl-5,6-epo xy- 2-cyclohexene-1,4-dione. Compound 2 was revealed to be the dechlorinated derivative of 1. Compounds 3 and 4 were determined to be the reduced derivative of 2 and 1, respectively.
3. Epoxyquinomicins A, B, C and D, new antibiotics from Amycolatopsis. I. Taxonomy, fermentation, isolation and antimicrobial activities
N Matsumoto, T Tsuchida, M Umekita, N Kinoshita, H Iinuma, T Sawa, M Hamada, T Takeuchi J Antibiot (Tokyo). 1997 Nov;50(11):900-5. doi: 10.7164/antibiotics.50.900.
A new structural class of the antibiotic, epoxyquinomicins A, B, C and D were isolated from the culture broth of the strain MK299-95F4, which was related to Amycolatopsis sulphurea. Antimicrobial activity of epoxyquinomicins A and B were weak against Gram-positive bacteria, and epoxyquinomicins C and D showed almost no antimicrobial activity and no cytotoxicity. All these antibiotics showed improvement of collagen induced arthritis in vivo.

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