Dehydrorabelomycin
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| Category | Others |
| Catalog number | BBF-05129 |
| CAS | 30954-70-2 |
| Molecular Weight | 320.3 |
| Molecular Formula | C19H12O5 |
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Specification
| Synonyms | 1,6,8-Trihydroxy-3-methylbenz[a]anthracene-7,12-dione; 6-Hydroxytetrangulol |
| IUPAC Name | 1,6,8-trihydroxy-3-methylbenzo[a]anthracene-7,12-dione |
| Canonical SMILES | CC1=CC2=CC(=C3C(=C2C(=C1)O)C(=O)C4=C(C3=O)C(=CC=C4)O)O |
| InChI | InChI=1S/C19H12O5/c1-8-5-9-7-13(22)16-17(14(9)12(21)6-8)18(23)10-3-2-4-11(20)15(10)19(16)24/h2-7,20-22H,1H3 |
| InChI Key | PQVIKROZFPIERS-UHFFFAOYSA-N |
Properties
| Boiling Point | 609.8±50.0°C at 760 mmHg |
| Density | 1.6±0.1 g/cm3 |
Reference Reading
1. Biochemical and structural insights of multifunctional flavin-dependent monooxygenase FlsO1-catalyzed unexpected xanthone formation
Chunfang Yang, Liping Zhang, Wenjun Zhang, Chunshuai Huang, Yiguang Zhu, Xiaodong Jiang, Wei Liu, Mengran Zhao, Bidhan Chandra De, Changsheng Zhang Nat Commun. 2022 Sep 14;13(1):5386. doi: 10.1038/s41467-022-33131-0.
Xanthone-containing natural products display diverse pharmacological properties. The biosynthetic mechanisms of the xanthone formation have not been well documented. Here we show that the flavoprotein monooxygenase FlsO1 in the biosynthesis of fluostatins not only functionally compensates for the monooxygenase FlsO2 in converting prejadomycin to dehydrorabelomycin, but also unexpectedly converts prejadomycin to xanthone-containing products by catalyzing three successive oxidations including hydroxylation, epoxidation and Baeyer-Villiger oxidation. We also provide biochemical evidence to support the physiological role of FlsO1 as the benzo[b]-fluorene C5-hydrolase by using nenestatin C as a substrate mimic. Finally, we resolve the crystal structure of FlsO1 in complex with the cofactor flavin adenine dinucleotide close to the "in" conformation to enable the construction of reactive substrate-docking models to understand the basis of a single enzyme-catalyzed multiple oxidations. This study highlights a mechanistic perspective for the enzymatic xanthone formation in actinomycetes and sets an example for the versatile functions of flavoproteins.
2. Offloading Role of a Discrete Thioesterase in Type II Polyketide Biosynthesis
Kangmin Hua, Xiangyang Liu, Yuchun Zhao, Yaojie Gao, Lifeng Pan, Haoran Zhang, Zixin Deng, Ming Jiang mBio. 2020 Sep 15;11(5):e01334-20. doi: 10.1128/mBio.01334-20.
Type II polyketides are a group of secondary metabolites with various biological activities. In nature, biosynthesis of type II polyketides involves multiple enzymatic steps whereby key enzymes, including ketoacyl-synthase (KSα), chain length factor (KSβ), and acyl carrier protein (ACP), are utilized to elongate the polyketide chain through a repetitive condensation reaction. During each condensation, the biosynthesis intermediates are covalently attached to KSα or ACP via a thioester bond and are then cleaved to release an elongated polyketide chain for successive postmodification. Despite its critical role in type II polyketide biosynthesis, the enzyme and its corresponding mechanism for type II polyketide chain release through thioester bond breakage have yet to be determined. Here, kinamycin was used as a model compound to investigate the chain release step of type II polyketide biosynthesis. Using a genetic knockout strategy, we confirmed that AlpS is required for the complete biosynthesis of kinamycins. Further in vitro biochemical assays revealed high hydrolytic activity of AlpS toward a thioester bond in an aromatic polyketide-ACP analog, suggesting its distinct role in offloading the polyketide chain from ACP during the kinamycin biosynthesis. Finally, we successfully utilized AlpS to enhance the heterologous production of dehydrorabelomycin in Escherichia coli by nearly 25-fold, which resulted in 0.50 g/liter dehydrorabelomycin in a simple batch-mode shake flask culture. Taken together, our results provide critical knowledge to gain an insightful understanding of the chain-releasing process during type II polyketide synthesis, which, in turn, lays a solid foundation for future new applications in type II polyketide bioproduction.
3. Purification and characterization of anti-phytopathogenic fungi angucyclinone from soil-derived Streptomyces cellulosae
Xindong Xu, Yang Zhao, Kang Bao, Cuiping Miao, Lixing Zhao, Youwei Chen, Shaohua Wu, Yiqing Li Folia Microbiol (Praha). 2022 Jun;67(3):517-522. doi: 10.1007/s12223-022-00957-6. Epub 2022 Feb 22.
Actinomycete strain YIM PH20352, isolated from the rhizosphere soil sample of Panax notoginseng collected in WenShang, Yunnan Province, China, exhibited antifungal activity against some phytopathogenic fungi. The structures of bioactive molecules, isolated from the ethyl acetate extract of the fermentation broth of the strain, were identified as rabelomycin (1) and dehydrorabelomycin (2) based on extensive spectroscopic analyses. Compound 1 exhibited antifungal activity against four tested root-rot pathogens of the Panax notoginseng including Plectosphaerella cucumerina, Alternaria panax, Fusarium oxysporum, and Fusarium solani with the MIC values at 32, 64, 128, and 128 μg/mL, respectively. Compound 2 exhibited antifungal activity against F. oxysporum, P. cucumerina, F. solani, and A. panax with the MIC values at 64, 64, 128, and 128 μg/mL, respectively. Based on the phylogenetic analyses, the closest phylogenetic relative of strain YIM PH20352 is Streptomyces cellulosae NBRC 13027 T (AB184265) (99.88%), so strain YIM PH20352 was identified as Streptomyces cellulosae. To the best of our knowledge, this is the first report of rabelomycin and rabelomycin-type antibiotics from Streptomyces cellulosae and their antifungal activity against root-rot pathogens of the Panax notoginseng.
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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 ╳
