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Menoxymycin B

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Menoxymycin B
Category Antibiotics
Catalog number BBF-01923
CAS 160523-76-2
Molecular Weight 489.51
Molecular Formula C25H31NO9

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Menoxymycin B is an antibiotic produced by Str. sp. KB10. It has a cytotoxic effect. It inhibits KB and N18-RE-105 cells with IC50 of 0.22 μmol/L and 0.023 μmol/L. Dithiothreitol (DDT) can reduce A and B cytotoxicity effect.

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IUPAC Name methyl 2-[(1R,3R,4R)-8-[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4,9-dihydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetate
Canonical SMILES CC1C(C(CC(O1)C2=C(C3=C(C=C2)C(=O)C4=C(C3=O)C(OC(C4O)CC(=O)OC)C)O)N(C)C)O
InChI InChI=1S/C25H31NO9/c1-10-18-20(24(31)16(34-10)9-17(27)33-5)23(30)13-7-6-12(22(29)19(13)25(18)32)15-8-14(26(3)4)21(28)11(2)35-15/h6-7,10-11,14-16,21,24,28-29,31H,8-9H2,1-5H3/t10-,11-,14-,15-,16-,21-,24+/m1/s1
InChI Key YPUKEVIVDLXYHG-VUHJHAOPSA-N
Appearance Yellow Powder
Boiling Point 718.4±60.0°C at 760 mmHg
Melting Point 93-97°C (dec.)
Density 1.4±0.1 g/cm3
1. Biomolecular-chemical screening: a novel screening approach for the discovery of biologically active secondary metabolites. III. New DNA-binding metabolites
C Maul, I Sattler, M Zerlin, C Hinze, C Koch, A Maier, S Grabley, R Thiericke J Antibiot (Tokyo). 1999 Dec;52(12):1124-34. doi: 10.7164/antibiotics.52.1124.
Based on the chemical screening technique, biomolecular-chemical screening has been developed which makes use of two-dimensional TLC analysis of microbial extracts and combines thin-layer chromatography (RP-18) with binding studies towards DNA. In the first dimension the metabolites of the crude microbial extract are separated, and in the second dimension binding properties towards DNA are analysed. An initial screening program with 500 microbial extracts prepared by solid-phase extraction with XAD-16 resin resulted in 17 samples which contained metabolites with significant DNA-binding behavior. Fermentation, isolation and structural characterization led to already known metabolites [phenazine-1,6-dicarboxylate (1), phencomycin (2), 11-carboxy-menoxymycin B (3), soyasaponine I (4), and (8S)-3-(2-hydroxypropyl)-cyclohexanone (5)], as well as to new secondary metabolites. Fermentation of the producing organisms of the new DNA-binding metabolites, ent-8,8adihydro-ramulosin (6). (2R,4R)-4-hydroxy-2-(1,3-pentadienyl)-piperidine (7), (5R)-dihydro-5-pentyl-4'-methyl-4'-hydroxy-2(3H)-furanone (8), and seco-4,23-hydroxyoleane-12-en-22-one-3-carboxylic acid (9), as well as isolation, structural characterization, and physico-chemical properties are reported.

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