Difficidin
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| Category | Bioactive by-products |
| Catalog number | BBF-01395 |
| CAS | 95152-88-8 |
| Molecular Weight | 544.66 |
| Molecular Formula | C31H45O6P |
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Description
Difficidin is produced by the strain of Bacillus subtilis. It has broad spectrum of aerobic and anaerobic bacterial activity.
Specification
| IUPAC Name | [(4E,6E,12Z,14Z,16E)-7,19-dimethyl-2-[(3E)-3-methylhexa-3,5-dienyl]-20-methylidene-22-oxo-1-oxacyclodocosa-4,6,12,14,16-pentaen-8-yl] dihydrogen phosphate |
| Canonical SMILES | CC1CC=CC=CC=CCCCC(C(=CC=CCC(OC(=O)CC1=C)CCC(=CC=C)C)C)OP(=O)(O)O |
| InChI | InChI=1S/C31H45O6P/c1-6-17-25(2)22-23-29-20-16-15-19-27(4)30(37-38(33,34)35)21-14-12-10-8-7-9-11-13-18-26(3)28(5)24-31(32)36-29/h6-11,13,15-17,19,26,29-30H,1,5,12,14,18,20-24H2,2-4H3,(H2,33,34,35)/b9-7-,10-8-,13-11+,16-15+,25-17+,27-19+ |
| InChI Key | ZUWUQYGHRURWCL-XUIVTPDHSA-N |
Properties
| Density | 1.09 g/cm3 |
Reference Reading
1. Bacillus velezensis: A Valuable Member of Bioactive Molecules within Plant Microbiomes
Muhammad Fazle Rabbee, Md Sarafat Ali, Jinhee Choi, Buyng Su Hwang, Sang Chul Jeong, Kwang-Hyun Baek Molecules. 2019 Mar 16;24(6):1046. doi: 10.3390/molecules24061046.
Bacillus velezensis is an aerobic, gram-positive, endospore-forming bacterium that promotes plant growth. Numerous strains of this species have been reported to suppress the growth of microbial pathogens, including bacteria, fungi, and nematodes. Based on recent phylogenetic analysis, several Bacillus species have been reclassified as B. velezensis. However, this information has yet to be integrated into a well-organized resource. Genomic analysis has revealed that B. velezensis possesses strain-specific clusters of genes related to the biosynthesis of secondary metabolites, which play significant roles in both pathogen suppression and plant growth promotion. More specifically, B. velezensis exhibits a high genetic capacity for synthesizing cyclic lipopeptides (i.e., surfactin, bacillomycin-D, fengycin, and bacillibactin) and polyketides (i.e., macrolactin, bacillaene, and difficidin). Secondary metabolites produced by B. velezensis can also trigger induced systemic resistance in plants, a process by which plants defend themselves against recurrent attacks by virulent microorganisms. This is the first study to integrate previously published information about the Bacillus species, newly reclassified as B. velezensis, and their beneficial metabolites (i.e., siderophore, bacteriocins, and volatile organic compounds).
2. Biological control of tomato bacterial wilt by oxydifficidin and difficidin-producing Bacillus methylotrophicus DR-08
Seong Mi Im, Nan Hee Yu, Hee Won Joen, Soon Ok Kim, Hae Woong Park, Ae Ran Park, Jin-Cheol Kim Pestic Biochem Physiol. 2020 Feb;163:130-137. doi: 10.1016/j.pestbp.2019.11.007. Epub 2019 Nov 9.
Bacillus methylotrophicus DR-08 exhibited strong antibacterial activity against Ralstonia solanacearum, a causal agent of tomato bacterial wilt. This study aimed to identify the antibacterial metabolites and evaluate the efficacy of the strain as a biocontrol agent for tomato bacterial wilt. A butanol extract of the DR-08 broth culture completely inhibited the growth of 14 phytopathogenic bacteria with minimum inhibitory concentration (MIC) values of 1.95-500 μg/mL. R. solanacearum was highly sensitive to the DR-08 extract, with an MIC value of 12.62 μg/mL. Two antibacterial metabolites were isolated and identified as difficidin and oxydifficidin derivatives through bioassay-guided fractionation and instrumental analyses. Both metabolite derivatives inhibited the growth of most of the phytopathogenic bacteria tested and the oxydifficidin derivatives generally presented a stronger antibacterial activity than the difficidin derivatives. A 30% suspension concentrate of DR-08, at a 500-fold dilution, effectively suppressed the development of tomato bacterial wilt in pot and field experiments. It also effectively reduced the development of bacterial leaf spot symptoms on peach and red pepper. The results of this study suggests that B. methylotrophicus DR-08 can be utilized as a biocontrol agent for various bacterial plant diseases including tomato bacterial wilt.
3. Difficidin class of polyketide antibiotics from marine macroalga-associated Bacillus as promising antibacterial agents
Kajal Chakraborty, Vinaya Kizhakkepatt Kizhakkekalam, Minju Joy, Shubhajit Dhara Appl Microbiol Biotechnol. 2021 Aug;105(16-17):6395-6408. doi: 10.1007/s00253-021-11390-z. Epub 2021 Aug 20.
A heterotrophoic Bacillus amyloliquefaciens MTCC12713 isolated from an intertidal macroalga Kappaphycus alverezii displayed promising antibacterial activities against multidrug-resistant bacteria. Genome mining of the bacterium predicted biosynthetic gene clusters coding for antibacterial secondary metabolites. Twenty-one membered macrocyclic lactones, identified as difficidin analogues bearing 6-hydroxy-8-propyl carboxylate, 9-methyl-19-propyl dicarboxylate, 6-methyl-9-propyl dicarboxylate-19-propanone, and (20-acetyl)-6-methyl-9-isopentyl dicarboxylate (compounds 1 through 4) functionalities were purified through bioassay-guided fractionation. The difficidin analogues exhibited bactericidal activities against vancomycin-resistant Enterococcus faecalis, methicillin-resistant Staphylococcus aureus, and other drug-resistant strains, such of Klebsiella pneumonia and Pseudomonas aeruginosa with the minimum inhibitory concentration of about 2-9 × 10-3 μM. A plausible enzyme-catalyzed biosynthetic pathway that is generated through addition of acrylyl initiator unit by repetitive decarboxylative Claisen condensation modules with malonate units was recognized, and their structures were corroborated with gene organization of the dif operon, which could comprehend dif A-O (~ 70 kb). Drug-likeness score for 5-ethoxy-28-methyl-(9-methyl-19-propyl dicarboxylate) difficidin (compound 2, 0.35) was greater than those of other difficidin analogues, which corroborated the potential in vitro antibacterial properties of the former. The present study demonstrated the potential of difficidin analogues for pharmaceutical and biotechnological uses against the bottleneck of emergent drug-resistant pathogens. KEY POINTS: · Difficidins were isolated from marine alga associated Bacillus amyloliquefaciens. · Whole-genome mining of bacterial genome predicted biosynthetic gene clusters. · Greater drug-likeness for difficidin 2 confirmed its potent antibacterial activity.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
