BE-54238B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Mycotoxins |
| Catalog number | BBF-03244 |
| CAS | 205433-27-8 |
| Molecular Weight | 395.40 |
| Molecular Formula | C22H21NO6 |
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Description
BE-54238B is a cytotoxic agent produced by Streptomyces sp. A54238. It has anti-proliferative effects on tumor cells such as P388, DLD4, PC-13, MKN-45, colon 26, etc., with IC50 of (μg/mL) 58.2, 10.1, 53.2, 45.6, 20.5.
Specification
| Synonyms | BE-54238 B |
| IUPAC Name | 11-hydroxy-20-(1-hydroxyethyl)-9-methyl-4,8-dioxa-21-azahexacyclo[10.9.1.02,10.03,7.016,22.017,21]docosa-1,10,12(22),14,16-pentaene-5,13-dione |
| Canonical SMILES | CC1C2=C(C3=C4C(=C5CCC(N5C4=C2C6C(O1)CC(=O)O6)C(C)O)C=CC3=O)O |
| InChI | InChI=1S/C22H21NO6/c1-8(24)11-4-5-12-10-3-6-13(25)18-17(10)20(23(11)12)19-16(21(18)27)9(2)28-14-7-15(26)29-22(14)19/h3,6,8-9,11,14,22,24,27H,4-5,7H2,1-2H3 |
| InChI Key | GROPDRMIDADBEP-UHFFFAOYSA-N |
Properties
| Appearance | Orange Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
Reference Reading
1. Discovery of C-Glycosylpyranonaphthoquinones in Streptomyces sp. MBT76 by a Combined NMR-Based Metabolomics and Bioinformatics Workflow
Changsheng Wu, Chao Du, Koji Ichinose, Young Hae Choi, Gilles P van Wezel J Nat Prod. 2017 Feb 24;80(2):269-277. doi: 10.1021/acs.jnatprod.6b00478. Epub 2017 Jan 27.
Mining of microbial genomes has revealed that actinomycetes harbor far more biosynthetic potential for bioactive natural products than anticipated. Activation of (cryptic) biosynthetic gene clusters and identification of the corresponding metabolites has become a focal point for drug discovery. Here, we applied NMR-based metabolomics combined with bioinformatics to identify novel C-glycosylpyranonaphthoquinones in Streptomyces sp. MBT76 and to elucidate the biosynthetic pathway. Following activation of the cryptic qin gene cluster for a type II polyketide synthase (PKS) by constitutive expression of its pathway-specific activator, bioinformatics coupled to NMR profiling facilitated the chromatographic isolation and structural elucidation of qinimycins A-C (1-3). The intriguing structural features of the qinimycins, including 8-C-glycosylation, 5,14-epoxidation, and 13-hydroxylation, distinguished these molecules from the model pyranonaphthoquinones actinorhodin, medermycin, and granaticin. Another novelty lies in the unusual fusion of a deoxyaminosugar to the pyranonaphthoquinone backbone during biosynthesis of the antibiotics BE-54238 A and B (4, 5). Qinimycins showed weak antimicrobial activity against Gram-positive bacteria. Our work shows the utility of combining bioinformatics, targeted activation of cryptic gene clusters, and NMR-based metabolic profiling as an effective pipeline for the discovery of microbial natural products with distinctive skeletons.
2. Glenthenamines A-F: Enamine Pyranonaphthoquinones from the Australian Pasture Plant Derived Streptomyces sp. CMB-PB042
Taizong Wu, Angela A Salim, Hui Cui, Zeinab G Khalil, Paul V Bernhardt, Robert J Capon J Nat Prod. 2022 Feb 25;85(2):337-344. doi: 10.1021/acs.jnatprod.1c00821. Epub 2022 Jan 24.
Chemical investigations into solid phase cultivations of an Australian sheep station pasture plant derived Streptomyces sp. CMB-PB042 yielded the rare enamine naphthopyranoquinones BE-54238A (1) and BE-54238B (2), together with four new analogues, glenthenamines B-D (4-6) and F (8), and two handling artifacts, glenthenamines A (3) and E (7). Single-crystal X-ray analyses of 1 and 2 resolved configurational ambiguities in the scientific literature, while detailed spectroscopic analysis and biosynthetic considerations assigned structures inclusive of absolute configuration to 3-8. We propose a plausible sequence of biosynthetic transformations linking structural and configurational features of 1-8 and apply a novel Schiff base "fishing" approach to detect a key deoxyaminosugar precursor. These enamine naphthopyranoquinones disclose a new P-gp inhibitory pharmacophore capable of reversing doxorubicin resistance in P-gp overexpressing colon carcinoma cells.
3. 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.
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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 ╳
