Labilomycin

Labilomycin

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Labilomycin
Category Antibiotics
Catalog number BBF-02223
CAS 11006-66-9
Molecular Weight 839.02
Molecular Formula C47H66O13

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Description

It is produced by the strain of Str. albospoeus var. labilomyceticus A955-y3. It's a sugar antibiotic. It has anti-gram-positive bacteria, mycobacterium activity. It had cytotoxic effect on HeLa cells and Yoshida sarcoma cells. Each rat (Transplantation of airy ascites carcinoma in mice) is given Labilomycin of 250 μg/d, it can inhibit tumor and prolong life. It has a protective effect on mice infected with S. aureus. Serum does not affect its antibacterial activity.

Specification

Synonyms Pulvomycin; Oxacyclodocosa-4,7,9,11,15,17,19-heptaene-2,13-dione, 22-[(1S,2S,3S,5E,7E,9E,11S,12S)-12-[(6-deoxy-2,4-di-O-methyl-β-D-galactopyranosyl)oxy]-2,11-dihydroxy-1,3-dimethyl-4-oxo-5,7,9-tridecatrien-1-yl]-6,14-dihydroxy-5,8,12-trimethyl-, (4E,6R,7E,9E,11E,14S,15E,17E,19E,22S)-; (4E,6R,7E,9E,11E,14S,15E,17E,19E,22S)-22-[(1S,2S,3S,5E,7E,9E,11S,12S)-12-[(6-Deoxy-2,4-di-O-methyl-β-D-galactopyranosyl)oxy]-2,11-dihydroxy-1,3-dimethyl-4-oxo-5,7,9-tridecatrien-1-yl]-6,14-dihydroxy-5,8,12-trimethyloxacyclodocosa-4,7,9,11,15,17,19-heptaene-2,13-dione; (-)-Pulvomycin; Antibiotic 1063Z
IUPAC Name (4E,6R,7E,9E,11E,14S,15E,17E,19E,22S)-22-[(2S,3S,4S,6E,8E,10E,12S,13S)-3,12-dihydroxy-13-[(2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy-4-methyl-5-oxotetradeca-6,8,10-trien-2-yl]-6,14-dihydroxy-5,8,12-trimethyl-1-oxacyclodocosa-4,7,9,11,15,17,19-heptaene-2,13-dione
Canonical SMILES CC1C(C(C(C(O1)OC(C)C(C=CC=CC=CC(=O)C(C)C(C(C)C2CC=CC=CC=CC(C(=O)C(=CC=CC(=CC(C(=CCC(=O)O2)C)O)C)C)O)O)O)OC)O)OC
InChI InChI=1S/C47H66O13/c1-29-20-19-21-31(3)42(53)38(50)24-17-11-10-12-18-25-40(60-41(52)27-26-30(2)39(51)28-29)33(5)43(54)32(4)36(48)22-15-13-14-16-23-37(49)34(6)58-47-46(57-9)44(55)45(56-8)35(7)59-47/h10-24,26,28,32-35,37-40,43-47,49-51,54-55H,25,27H2,1-9H3/b11-10+,14-13+,18-12+,20-19+,22-15+,23-16+,24-17+,29-28+,30-26+,31-21+/t32-,33-,34+,35-,37+,38+,39-,40+,43-,44+,45+,46-,47-/m1/s1
InChI Key FXSFWUNCIOIMAC-VXILMCRLSA-N

Properties

Appearance Pale Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor); Mycobacteria
Boiling Point 990.7±65.0°C (Predicted)
Melting Point 94-97°C
Density 1.19±0.1 g/cm3 (Predicted)
Solubility Soluble in Methanol, Chloroform

Reference Reading

1. Identification of pulvomycin as an inhibitor of the futalosine pathway
Yasushi Ogasawara, Shuhei Umetsu, Yuki Inahashi, Kenichi Nonaka, Tohru Dairi J Antibiot (Tokyo). 2021 Nov;74(11):825-829. doi: 10.1038/s41429-021-00465-8. Epub 2021 Aug 20.
Menaquinone is an essential cofactor in the electron-transfer pathway for bacteria. Menaquinone is biosynthesized from chorismate using either the well-known canonical pathway established by pioneering studies in model microorganisms or the futalosine pathway, which we discovered in Streptomyces. Because Helicobacter pylori, which causes stomach cancer, uses the futalosine pathway and most beneficial intestinal bacteria including lactobacilli use the canonical pathway, the futalosine pathway will be a great target to develop antibiotics specific for H. pylori. Here, we searched for such compounds from metabolites produced by actinomycetes and identified pulvomycin from culture broth of Streptomyces sp. K18-0194 as a specific inhibitor of the futalosine pathway.
2. Total Synthesis of Pulvomycin D
Lukas Fritz, Sebastian Wienhold, Sabrina Hackl, Thorsten Bach Chemistry. 2022 Jan 13;28(3):e202104064. doi: 10.1002/chem.202104064. Epub 2021 Dec 7.
A synthetic route to the pulvomycin class of natural products is presented, which culminated in the first synthesis of a pulvomycin, pulvomycin D. Key elements of the strategy include a pivotal aldol reaction which led to bond formation between the C24-C40 and the C8-C23 fragment. The remaining C1-C7 fragment was attached by a Yamaguchi esterification completing the assembly of the 40 carbon atoms within the main skeleton. Ring closure to the 22-membered lactone ring was achieved in the final stages of the synthesis by a Heck reaction. The completion of the synthesis required the removal of six silyl protecting groups in combination with olefin formation at C26-C27 by a Peterson elimination.
3. Detection of antimicrobial resistance genes in urban air
Ágnes Becsei, Norbert Solymosi, István Csabai, Donát Magyar Microbiologyopen. 2021 Nov;10(6):e1248. doi: 10.1002/mbo3.1248.
To understand antibiotic resistance in pathogenic bacteria, we need to monitor environmental microbes as reservoirs of antimicrobial resistance genes (ARGs). These bacteria are present in the air and can be investigated with the whole metagenome shotgun sequencing approach. This study aimed to investigate the feasibility of a method for metagenomic analysis of microbial composition and ARGs in the outdoor air. Air samples were collected with a Harvard impactor in the PM10 range at 50 m from a hospital in Budapest. From the DNA yielded from samples of PM10 fraction single-end reads were generated with an Ion Torrent sequencer. During the metagenomic analysis, reads were classified taxonomically. The core bacteriome was defined. Reads were assembled to contigs and the ARG content was analyzed. The dominant genera in the core bacteriome were Bacillus, Acinetobacter, Leclercia and Paenibacillus. Among the identified ARGs best hits were vanRA, Bla1, mphL, Escherichia coli EF-Tu mutants conferring resistance to pulvomycin; BcI, FosB, and mphM. Despite the low DNA content of the samples of PM10 fraction, the number of detected airborne ARGs was surprisingly high.

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