Lagunamycin

Lagunamycin

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Lagunamycin
Category Antibiotics
Catalog number BBF-02231
CAS 150693-65-5
Molecular Weight 355.39
Molecular Formula C19H21N3O4
Purity 95%

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Description

It is produced by the strain of Str. sp. AA0310. It can inhibit 5-fat oxygenase with IC50 of 6.08 μmol/L, but dose not inhibit lipid peroxidation. It has the activity of anti-gram-positive bacteria, not anti-gram-negative bacteria.

Specification

Synonyms (E)-(-)-6-Diazo-3-methyl-4-(1,3,5-trimethyl-1-hexenyl)-2,5,7,8(1H,6H)-quinolinetetrone; 6-diazonio-4-[(E)-4,6-dimethylhept-2-en-2-yl]-3-methyl-2,7,8-trioxo-1H-quinolin-5-olate
IUPAC Name 6-diazo-4-[(E)-4,6-dimethylhept-2-en-2-yl]-3-methyl-1H-quinoline-2,5,7,8-tetrone
Canonical SMILES CC1=C(C2=C(C(=O)C(=O)C(=[N+]=[N-])C2=O)NC1=O)C(=CC(C)CC(C)C)C
InChI InChI=1S/C19H21N3O4/c1-8(2)6-9(3)7-10(4)12-11(5)19(26)21-14-13(12)16(23)15(22-20)18(25)17(14)24/h7-9H,6H2,1-5H3,(H,21,26)/b10-7+
InChI Key PJKDXVRDJPKOHU-JXMROGBWSA-N

Properties

Appearance Yellow Acicular Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 134-136°C
Solubility Soluble in Methanol, Methanol-Hydrochloric acid, Methanol-Sodium hydroxide

Reference Reading

1. Microbial diversity of saline environments: searching for cytotoxic activities
Carolina Díaz-Cárdenas, Angela Cantillo, Laura Yinneth Rojas, Tito Sandoval, Susana Fiorentino, Jorge Robles, Freddy A Ramos, María Mercedes Zambrano, Sandra Baena AMB Express. 2017 Dec 22;7(1):223. doi: 10.1186/s13568-017-0527-6.
In order to select halophilic microorganisms as a source of compounds with cytotoxic activities, a total of 135 bacterial strains were isolated from water and sediment samples collected from the Zipaquirá salt mine in the Colombian Andes. We determined the cytotoxic effects of 100 crude extracts from 54 selected organisms on the adherent murine mammary cell carcinoma 4T1 and human mammary adenocarcinoma MCF-7 cell lines. These extracts were obtained from strains of Isoptericola, Ornithinimicrobium, Janibacter, Nesterenkonia, Alkalibacterium, Bacillus, Halomonas, Chromohalobacter, Shewanella, Salipiger, Martellela, Oceanibaculum, Caenispirillum and Labrenzia. The extracts of 23 strains showed an IC50 of less than 100 μg mL-1. They were subsequently analyzed by LC/MS allowing dereplication of 20 compounds. The cytotoxic effect was related to a complex mixture of diketopiperazines present in many of the extracts analyzed. The greatest cytotoxic activity against both of the evaluated cell lines was obtained from the chloroform extract of Labrenzia aggregata USBA 371 which had an IC50 < 6 μg mL-1. Other extracts with high levels of cytotoxic activity were obtained from Bacillus sp. (IC50 < 50 μg mL-1) which contained several compounds such as macrolactin L and A, 7-O-succinoylmacrolactin F and iturin. Shewanella chilikensis USBA 344 also showed high levels of cytotoxic activity against both cell lines in the crude extract: an IC50 < 15 μg mL-1 against the 4T1 cell line and an IC50 < 68 μg mL-1 against the MCF-7 cell line. Nesterenkonia sandarakina CG 35, which has an IC50 of 118 µg mL-1 against 4T1, is a producer of diketopiperazines and 1-acetyl-β-carboline. Also, Ornithinimicrobium kibberense CG 24, which has IC50 < 50 μg mL-1, was a producer of diketopiperazines and lagunamycin. Our study demonstrates that these saline environments are habitats of halophilic and halotolerant bacteria that have previously unreported cytotoxic activity.
2. Total syntheses of polyketide-derived bioactive natural products
Kuniaki Tatsuta, Seijiro Hosokawa Chem Rec. 2006;6(4):217-33. doi: 10.1002/tcr.20084.
Recent progress of total syntheses in our laboratory has been described along with our background and methodologies. The target bioactive polyketides are classified into three categories according to their structures: (i) lactone-fused polycyclic compounds [(+)-cochleamycin A, (+)-tubelactomicin A, and (-)-tetrodecamycin], (ii) aromatic compounds [(-)-tetracycline, (-)-BE-54238B, lymphostin, and (-)-lagunamycin], and (iii) acyclic polyketides [xanthocillin X dimethylether, (+)-trichostatin D, and (+)-actinopyrone A]. Features of the total syntheses are described. Original methodologies have been developed and applied to construct the inherent structures of the target molecules. Most syntheses cited herein are the first total syntheses, and the absolute structures of the target molecules have been determined.
3. Lagunamycin, a novel 5-lipoxygenase inhibitor. I. Taxonomy, fermentation, physico-chemical properties and biological characteristics
Y Nihei, M Hasegawa, K Suzuki, S Yamamoto, M Hanada, T Furumai, Y Fukagawa, T Oki J Antibiot (Tokyo). 1993 Jun;46(6):900-7. doi: 10.7164/antibiotics.46.900.
Lagunamycin, a novel 5-lipoxygenase inhibitor, was isolated from the culture broth of Streptomyces sp. AA0310. This compound showed potent rat 5-lipoxygenase inhibitory activity (IC50 6.08 microM) without lipid peroxidation.

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