Granaticin B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01278 |
| CAS | 19879-03-9 |
| Molecular Weight | 558.53 |
| Molecular Formula | C28H30O12 |
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Description
It is produced by the strain of Streptomyces olvaceus var. ETH 7437, Str. violaceoruber. It inhibits the initial stage of RNA biosynthesis, has anti-gram-positive bacteria, Mycobacterium (weak) and vaginal trichomonas activity, but also can inhibit tumor cells.
Specification
| IUPAC Name | (1R,7S,11S,13S,19S,20R,23R)-3,17,19-trihydroxy-23-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.02,18.04,16.06,14.07,11]tricosa-2(18),3,6(14),16-tetraene-5,9,15-trione |
| Canonical SMILES | CC1C(CCC(O1)OC2CC3C4=C(C2(C(O3)C)O)C(=C5C(=C4O)C(=O)C6=C(C5=O)C(OC7C6OC(=O)C7)C)O)O |
| InChI | InChI=1S/C28H30O12/c1-8-11(29)4-5-16(37-8)39-14-6-12-18-22(28(14,35)10(3)38-12)26(34)20-19(24(18)32)25(33)21-17(23(20)31)9(2)36-13-7-15(30)40-27(13)21/h8-14,16,27,29,32,34-35H,4-7H2,1-3H3/t8-,9-,10+,11-,12+,13-,14+,16-,27+,28-/m0/s1 |
| InChI Key | HLNZYALGGXMQQC-VHAJSWNUSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor); Mycobacteria; Parasites |
| Melting Point | 117-119 °C |
Reference Reading
1. Discovery of Mycothiogranaticins from Streptomyces vietnamensis GIMV4.0001 and the Regulatory Effect of Mycothiol on the Granaticin Biosynthesis
Ming-Rong Deng, Yan Li, Xiao Luo, Xiang-Ling Zheng, Yuchan Chen, Yu-Lian Zhang, Weimin Zhang, Hao Zhou, Honghui Zhu Front Chem. 2021 Dec 23;9:802279. doi: 10.3389/fchem.2021.802279. eCollection 2021.
Granaticins are benzoisochromanequinone polyketides with remarkable antibacterial and anticancer activities. Three sulfur-containing granaticin congeners, mycothiogranaticins A (1), B (2) and granaticin MA (3) were discovered from a granaticin-producing strain of Streptomyces vietnamensis GIMV4.0001. Two of them were structurally determined with mycothiol or N-acetylcysteine moieties and found to be bio-actively reluctant. Disruption of the mshA gene (SVTN_RS20640) that encodes the D-inositol-3-phosphate glycosyltransferase crucial for mycothiol biosynthesis, fully abolished the production of mycothiogranaticins. The result substantiated that the newly discovered mycothiogranaticins are consequences of the combination of the granaticin and mycothiol biosynthetic pathways. The overall granaticin production of the ΔmshA mutant strain was unexpectedly decreased by at least more than 50%, while similar production level of granaticins to that of the wild type strain was observed in an mycothiol-S transferase gene (SVTN_RS22215) disruptant Δmst. These results indicated that the mycothiol deficiency was responsible for the decreased production of granaticins. Mycothiol may positively regulate the biosynthesis of granaticin possibly by maintaining the cellular redox balance. To the best of our knowledge, this is the first report that mycothiol can not only be a direct building block of polyketides but also play a regulatory role in the polyketide biosynthesis.
2. Effective Antibiofilm Polyketides against Staphylococcus aureus from the Pyranonaphthoquinone Biosynthetic Pathways of Streptomyces Species
Terhi Oja, Paola San Martin Galindo, Takaaki Taguchi, Suvi Manner, Pia M Vuorela, Koji Ichinose, Mikko Metsä-Ketelä, Adyary Fallarero Antimicrob Agents Chemother. 2015 Oct;59(10):6046-52. doi: 10.1128/AAC.00991-15. Epub 2015 Jul 20.
Streptomyces bacteria are renowned for their ability to produce bioactive secondary metabolites. Recently, synthetic biology has enabled the production of intermediates and shunt products, which may have altered biological activities compared to the end products of the pathways. Here, we have evaluated the potential of recently isolated alnumycins and other closely related pyranonaphthoquinone (PNQ) polyketides against Staphylococcus aureus biofilms. The antimicrobial potency of the compounds against planktonic cells and biofilms was determined by redox dye-based viability staining, and the antibiofilm efficacy of the compounds was confirmed by viable counting. A novel antistaphylococcal polyketide, alnumycin D, was identified. Unexpectedly, the C-ribosylated pathway shunt product alnumycin D was more active against planktonic and biofilm cells than the pathway end product alnumycin A, where a ribose unit has been converted into a dioxane moiety. The evaluation of the antibiofilm potential of other alnumycins revealed that the presence of the ribose moiety in pyranose form is essential for high activity against preformed biofilms. Furthermore, the antibiofilm potential of other closely related PNQ polyketides was examined. Based on their previously reported activity against planktonic S. aureus cells, granaticin B, kalafungin, and medermycin were also selected for testing, and among them, granaticin B was found to be the most potent against preformed biofilms. The most active antibiofilm PNQs, alnumycin D and granaticin B, share several structural features that may be important for their antibiofilm activity. They are uncharged, glycosylated, and also contain a similar oxygenation pattern of the lateral naphthoquinone ring. These findings highlight the potential of antibiotic biosynthetic pathways as a source of effective antibiofilm compounds.
3. Sekgranaticin, a SEK34b-Granaticin Hybrid Polyketide from Streptomyces sp. 166
Qianqian Lv, Yaqin Fan, Ganzheng Tao, Peng Fu, Jingxin Zhai, Boping Ye, Weiming Zhu J Org Chem. 2019 Jul 19;84(14):9087-9092. doi: 10.1021/acs.joc.9b01022. Epub 2019 Jul 5.
Sekgranaticin (1), a novel hybrid polyketide with a complex 6/6/6/6/6/6/6 7-ring system, was isolated together with granaticins A (2) and B (3) and methyl granaticinate (4) from the culture broth of Streptomyces sp. 166#. Its structure was elucidated by spectroscopic analysis. The absolute configuration was determined on the basis of the calculated 13C NMR and electronic circular dichroism data. Compounds 1-4 exhibited potent cytotoxicity against cancer cell lines MCF-7, A549, P6C, and HCT-116 with IC50 values of 0.02-6.77 μM. The biosynthetic pathway of sekgranaticin (1) was proposed.
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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 ╳
