Albofungin

Albofungin

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Albofungin
Category Antibiotics
Catalog number BBF-00660
CAS 37895-35-5
Molecular Weight 520.49
Molecular Formula C27H24N2O9
Purity 95%

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Description

It is produced by the strain of Actinomyces albus var fungatus. It is mainly resistant to gram-positive bacteria and yeast, but not to gram-negative bacteria and filamentous fungi.

Specification

Synonyms 2H-Xantheno(1',2',3':4:5)(1,3)benzodioxino(7,6-g)isoquinoline-5,14(1H,9H)-dione, 13-amino-3,4,8a,13-tetrahydro-4,15,16-trihydroxy-1-methoxy-12-methyl-, (1R-(1-alpha,4-alpha,8a-beta))-; Antibiotic P 42-I; Antibiotic P42-C; (1S,4R,8aR)-13-amino-1,15,16-trihydroxy-4-methoxy-12-methyl-1,2,3,4,8a,13-hexahydro-17H-chromeno[2',3':6,7][1,3]dioxino[4',5',6':4,5]naphtho[2,1-g]isoquinoline-14,17(9H)-dione
Storage Store at 2-8°C
IUPAC Name (13R,21S,24R)-6-amino-3,21,28-trihydroxy-24-methoxy-7-methyl-14,16,26-trioxa-6-azaheptacyclo[15.11.1.02,11.04,9.013,29.018,27.020,25]nonacosa-1(28),2(11),3,7,9,17(29),18(27),20(25)-octaene-5,19-dione
Canonical SMILES CC1=CC2=CC3=C(C4=C(C5=C(C6=C4C(C3)OCO6)C(=O)C7=C(O5)C(CCC7O)OC)O)C(=C2C(=O)N1N)O
InChI InChI=1S/C27H24N2O9/c1-9-5-10-6-11-7-14-18-19(15(11)21(31)16(10)27(34)29(9)28)23(33)26-20(25(18)37-8-36-14)22(32)17-12(30)3-4-13(35-2)24(17)38-26/h5-6,12-14,30-31,33H,3-4,7-8,28H2,1-2H3/t12-,13+,14+/m0/s1
InChI Key LYKFTVCDYGGLGW-BFHYXJOUSA-N
Source Streptomyces sp.

Properties

Appearance Yellow Crystal
Antibiotic Activity Spectrum Gram-positive bacteria; Yeast
Boiling Point 869.4°C at 760 mmHg
Melting Point 304-307°C
Density 1.71 g/cm3
Solubility Soluble in Ethanol

Reference Reading

1. [Albofungin formation by a strain isolated as a result of fusion of protoplasts of organisms producing aminoglycoside antibiotics]
Iu V Dudnik, I A Malanicheva, L I Koz'mian, M Iu Novozhenov, A V Laĭko, N P Potapova Antibiot Khimioter . 1991 May;36(5):5-8.
Strain 344 synthesizing an antibiotic complex was isolated after fusion of the protoplasts of Streptomyces monomycini producing monomycin and Streptomyces kanamyceticus producing kanamycin. The major component of the complex was identified with albofungin and the minor one was suggested to be chloralbofungin. In the cultures of strain 344 variants forming monomycin were detected. After regeneration of the protoplasts of the parent strains there were isolated no stable clones synthesizing antibiotics differing from monomycin and kanamycin.
2. Discovery, Yield Improvement, and Application in Marine Coatings of Potent Antifouling Compounds Albofungins Targeting Multiple Fouling Organisms
Yujing Yuan, Yanhong Lu, Aifang Cheng, Wenkang Ye, Xuan Liu, Wei Ye, Ruojun Wang, Feng Chen, Weiyi She, Chunfeng Ma, Pei-Yuan Qian, Jinping Cheng, Sin Yu Chik, Jessie James Limlingan Malit Front Microbiol . 2022 Jul 7;13:906345. doi: 10.3389/fmicb.2022.906345.
Marine biofouling caused huge economic losses of maritime industries. We aim to develop high-efficient, less-toxic, and cost-effective antifoulants to solve the problems of biofouling. In this study, we described the antifouling compounds albofungin and its derivatives (albofungin A, chrestoxanthone A, and chloroalbofungin) isolated from the metabolites of bacteriumStreptomyces chrestomyceticusBCC 24770, the construction of high-yield strains for albofungin production, and application of albofungin-based antifouling coatings. Results showed that these albofungins have potent antibiofilm activities against Gram-positive and Gram-negative bacteria and anti-macrofouling activities against larval settlement of major fouling organisms with low cytotoxicity. With the best antifouling activity and highest yield in bacterial culture, albofungin was subsequently incorporated with hydrolyzable and degradable copolymer to form antifouling coatings, which altered biofilm structures and prevented the settlement of macrofouling organisms in marine environments. Our results suggested that albofungins were promising antifouling compounds with potential application in marine environments.
3. Proteomining-Based Elucidation of Natural Product Biosynthetic Pathways in Streptomyces
Qian Zhang, Darwin Linardi, Weiyi She, Pei-Yuan Qian, Yi Yu, Henry Lam Front Microbiol . 2022 Jul 11;13:913756. doi: 10.3389/fmicb.2022.913756.
The genusStreptomycesis known to harbor numerous biosynthetic gene clusters (BGCs) of potential utility in synthetic biology applications. However, it is often difficult to link uncharacterized BGCs with the secondary metabolites they produce. Proteomining refers to the strategy of identifying active BGCs by correlating changes in protein expression with the production of secondary metabolites of interest. In this study, we devised a shotgun proteomics-based workflow to identify active BGCs during fermentation when a variety of compounds are being produced. Mycelia harvested during the non-producing growth phase served as the background. Proteins that were differentially expressed were clustered based on the proximity of the genes in the genome to highlight active BGCs systematically from label-free quantitative proteomics data. Our software tool is easy-to-use and requires only 1 point of comparison where natural product biosynthesis was significantly different. We tested our proteomining clustering method on threeStreptomycesspecies producing different compounds. InStreptomyces coelicolorA3(2), we detected the BGCs of calcium-dependent antibiotic, actinorhodin, undecylprodigiosin, and coelimycin P1. InStreptomyces chrestomyceticusBCC24770, 7 BGCs were identified. Among them, we independently re-discovered the type II PKS for albofungin production previously identified by genome mining and tedious heterologous expression experiments. InStreptomyces tenebrarius, 5 BGCs were detected, including the known apramycin and tobramycin BGC as well as a newly discovered caerulomycin A BGC in this species. The production of caerulomycin A was confirmed by LC-MS and the inactivation of the caerulomycin A BGC surprisingly had a significant impact on the secondary metabolite regulation ofS. tenebrarius. In conclusion, we developed an unbiased, high throughput proteomics-based method to complement genome mining methods for the identification of biosynthetic pathways inStreptomycessp.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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