Dihydrogranaticin B
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| Category | Bioactive by-products |
| Catalog number | BBF-01402 |
| CAS | |
| Molecular Weight | 560.55 |
| Molecular Formula | C28H32O12 |
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Description
Produced by the strain of Streptomyces thermoviolaceus subsp. pigenes var. WR-141. It is a red pigment with activity against Bacillus cereus.
Specification
| IUPAC Name | 2-[(1R,7S,9R,16R,18R,19R)-1,3,14-trihydroxy-19-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.02,15.04,13.06,11]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid |
| Canonical SMILES | CC1C(CCC(O1)OC2CC3C4=C(C2(C(O3)C)O)C(=C5C(=C4O)C(=O)C6=C(C5=O)C(OC(C6)CC(=O)O)C)O)O |
| InChI | InChI=1S/C28H32O12/c1-9-14(29)4-5-18(38-9)40-16-8-15-20-23(28(16,36)11(3)39-15)27(35)22-21(26(20)34)24(32)13-6-12(7-17(30)31)37-10(2)19(13)25(22)33/h9-12,14-16,18,29,34-36H,4-8H2,1-3H3,(H,30,31)/t9-,10-,11+,12+,14-,15+,16+,18-,28+/m0/s1 |
| InChI Key | HLHVOERZDIDBHJ-SMQDJOASSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Upregulation and Identification of Antibiotic Activity of a Marine-Derived Streptomyces sp. via Co-Cultures with Human Pathogens
Anne A Sung, Samantha M Gromek, Marcy J Balunas Mar Drugs. 2017 Aug 11;15(8):250. doi: 10.3390/md15080250.
Marine natural product drug discovery has begun to play an important role in the treatment of disease, with several recently approved drugs. In addition, numerous microbial natural products have been discovered from members of the order Actinomycetales, particularly in the genus Streptomyces, due to their metabolic diversity for production of biologically active secondary metabolites. However, many secondary metabolites cannot be produced under laboratory conditions because growth conditions in flask culture differ from conditions in the natural environment. Various experimental conditions (e.g., mixed fermentation) have been attempted to increase yields of previously described metabolites, cause production of previously undetected metabolites, and increase antibiotic activity. Adult ascidians-also known as tunicates-are sessile marine invertebrates, making them vulnerable to predation and therefore are hypothesized to use host-associated bacteria that produce biologically active secondary metabolites for chemical defense. A marine-derived Streptomyces sp. strain PTY087I2 was isolated from a Panamanian tunicate and subsequently co-cultured with human pathogens including Bacillus subtilis, methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), and Pseudomonas aeruginosa, followed by extraction. Co-culture of Streptomyces sp. PTY087I2 with each of these human pathogens resulted in increased production of three antibiotics: granaticin, granatomycin D, and dihydrogranaticin B, as well as several analogues seen via molecular networking. In addition, co-cultures resulted in strongly enhanced biological activity against the Gram positive human pathogens used in these experiments. Expanded utilization of co-culture experiments to allow for competitive interactions may enhance metabolite production and further our understanding of these microbial interactions.
2. The granaticin biosynthetic gene cluster of Streptomyces violaceoruber Tü22: sequence analysis and expression in a heterologous host
K Ichinose, D J Bedford, D Tornus, A Bechthold, M J Bibb, W P Revill, H G Floss, D A Hopwood Chem Biol. 1998 Nov;5(11):647-59. doi: 10.1016/s1074-5521(98)90292-7.
Background: The granaticins are members of the benzoisochromanequinone class of aromatic polyketides, the best known member of which is actinorhodin made by Streptomyces coelicolor A3(2). Genetic analysis of this class of compounds has played a major role in the development of hypotheses about the way in which aromatic polyketide synthases (PKSs) control product structure. Although the granaticin nascent polyketide is identical to that of actinorhodin, post-PKS steps involve different pyran-ring stereochemistry and glycosylation. Comparison of the complete gene clusters for the two metabolites is therefore of great interest. Results: The entire granaticin gene cluster (the gra cluster) from Streptomyces violaceoruber T-22 was cloned on either of two overlapping cosmids and expressed in the heterologous host, Streptomyces coelicolor A3(2), strain CH999. Chemical analysis of the recombinant strains demonstrated production of granaticin, granaticin B, dihydrogranaticin and dihydrogranaticin B, which are the four known metabolites of S. violaceoruber. Analysis of the complete 39,250 base pair sequence of the insert of one of the cosmids, pOJ466-22-24, revealed 37 complete open reading frames (ORFs), 15 of which resemble ORFs from the act (actinorhodin) gene cluster of S. coelicolor A3(2). Among the rest, nine resemble ORFs potentially involved in deoxysugar metabolism from Streptomyces spp. and other bacteria, and six resemble regulatory ORFs. Conclusions: On the basis of these resemblances, putative functional assignments of the products of most of the newly discovered ORFs were made, including those of genes involved in the PKS and tailoring steps in the biosynthesis of the granaticin aglycone, steps in the deoxy sugar pathway, and putative regulatory and export functions.
3. 6-Deoxy-13-hydroxy-8,11-dione-dihydrogranaticin B, an intermediate in granaticin biosynthesis, from Streptomyces sp. CPCC 200532
Bingya Jiang, Shufen Li, Wei Zhao, Ting Li, Lijie Zuo, Yanni Nan, Linzhuan Wu, Hongyu Liu, Liyan Yu, Guangzhi Shan, Limin Zuo J Nat Prod. 2014 Sep 26;77(9):2130-3. doi: 10.1021/np500138k. Epub 2014 Aug 25.
A new granaticin analogue and its hydrolysis product were isolated from Streptomyces sp. CPCC 200532. Their structures were determined to be 6-deoxy-13-hydroxy-8,11-dione-dihydrogranaticins B (1) and A (2), respectively, by detailed analysis of spectroscopic data. Compound 1 was regarded as an intermediate in granaticin biosynthesis, as it was bioconvertable to granaticin B. Compared to granaticin B, 1 showed similar cytotoxicity against cancer cell line HCT116, but decreased cytotoxicity against cancer cell lines A549, HeLa, and HepG2. Compound 2 displayed lower cytotoxicity than 1 against all four cancer cell lines tested.
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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 ╳
