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Lachnumol A

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Category Antibiotics
Catalog number BBF-02227
CAS 150671-03-7
Molecular Weight 267.11
Molecular Formula C10H12Cl2O4

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Fermentation Lab

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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

It is produced by the strain of Lachnum papyraceum. It has weaker activity against bacteria, yeast and filamentous fungi. It has cytotoxic activity against L1210, HeLa, KB and other cell lines.

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Synonyms La; 1-chloro-6-[(Z)-1-chloroprop-1-enyl]-4-methoxy-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol; 7-Oxabicyclo(4.1.0)hept-3-ene-2,5-diol, 6-chloro-1-(1-chloro-1-propenyl)-3-methoxy-
IUPAC Name 6-chloro-1-[(Z)-1-chloroprop-1-enyl]-3-methoxy-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
Canonical SMILES CC=C(C12C(C(=CC(C1(O2)Cl)O)OC)O)Cl
InChI InChI=1S/C10H12Cl2O4/c1-3-6(11)9-8(14)5(15-2)4-7(13)10(9,12)16-9/h3-4,7-8,13-14H,1-2H3/b6-3-
InChI Key CLAFUBPFUBWURK-UTCJRWHESA-N
Appearance Colorless Oily Matter
Antibiotic Activity Spectrum Neoplastics (Tumor); Fungi; Yeast
Solubility Soluble in Methanol, Chloroform
1. Lachnumon and lachnumol a, new metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. I. Producing organism, fermentation, isolation and biological activities
M Stadler, H Anke, W R Arendholz, F Hansske, U Anders, O Sterner, K E Bergquist J Antibiot (Tokyo). 1993 Jun;46(6):961-7. doi: 10.7164/antibiotics.46.961.
Several chlorinated metabolites with nematicidal, antimicrobial, and cytotoxic activities were isolated from submerged cultures of the ascomycete Lachnum papyraceum. Three compounds were identified as (+)-mycorrhizin A (3), (+)-chloromycorrhizin A (4) and (+)-dechloromycorrhizin A (5). The occurrence of 5 as a natural product is new. Two compounds, lachnumon (1) and lachnumol A (2), were found to be new fungal metabolites with cytotoxic, nematicidal and antimicrobial activities.
2. Lachnumon and lachnumol a, new metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. II. Structural elucidation
M Stadler, H Anke, K E Bergquist, O Sterner J Antibiot (Tokyo). 1993 Jun;46(6):968-71. doi: 10.7164/antibiotics.46.968.
The structures of two new biologically active chlorinated metabolites isolated from submerged cultures of the ascomycete Lachnum papyraceum have been elucidated by NMR and mass spectroscopy. The compounds, lachnumon (1) and lachnumol A (2), which structurally are related with mycorrhizin A that also is produced by the fungus, contain an unusual chlorinated epoxide group.

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