Balanol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00627 |
| CAS | 63590-19-2 |
| Molecular Weight | 550.53 |
| Molecular Formula | C28H26N2O10 |
| Purity | >95% |
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Description
It is produced by the strain of Streptomyces sp. Tu 4128. Balanol, a fungal metabolite, is a potent ATP-competitive inhibitor of Protein Kinase C (PKC) and Protein Kinase A (PKA). It is an important target in oncology.
Specification
| Synonyms | 4-(2-Carboxy-6-hydroxybenzoyl)-3,5-dihydroxybenzoic Acid (3R,4R)-Hexahydro-3-[(4-hydroxybenzoyl)amino]-1H-azepin-4-yl Ester; (3R-trans)-Balanol; (-)-Balanol; Azepinostatin; Ophiocordin |
| IUPAC Name | 2-[2,6-dihydroxy-4-[(3R,4R)-3-[(4-hydroxybenzoyl)amino]azepan-4-yl]oxycarbonylbenzoyl]-3-hydroxybenzoic acid |
| Canonical SMILES | C1CC(C(CNC1)NC(=O)C2=CC=C(C=C2)O)OC(=O)C3=CC(=C(C(=C3)O)C(=O)C4=C(C=CC=C4O)C(=O)O)O |
| InChI | InChI=1S/C28H26N2O10/c31-16-8-6-14(7-9-16)26(36)30-18-13-29-10-2-5-22(18)40-28(39)15-11-20(33)24(21(34)12-15)25(35)23-17(27(37)38)3-1-4-19(23)32/h1,3-4,6-9,11-12,18,22,29,31-34H,2,5,10,13H2,(H,30,36)(H,37,38)/t18-,22-/m1/s1 |
| InChI Key | XYUFCXJZFZPEJD-XMSQKQJNSA-N |
Properties
| Appearance | Yellow Powder |
Reference Reading
1. Gram-Level Production of Balanol through Regulatory Pathway and Medium Optimization in Herb Fungus Tolypocladium ophioglossoides
Rui-Qi Li, Xiang Liu, Min Zhang, Wei-Qun Xu, Yong-Quan Li, Xin-Ai Chen J Fungi (Basel). 2022 May 16;8(5):510. doi: 10.3390/jof8050510.
As a potential protein kinase C inhibitor, the fungus metabolite balanol has become more attractive in recent decades. In our previous work, we revealed its biosynthetic pathway through overexpression of the cluster-situated regulator gene blnR in Chinese herb fungus Tolypocladium ophioglossoides. However, information on the regulation of blnR is still largely unknown. In this study, we further investigated the regulation of balanol biosynthesis by BlnR through the analysis of affinity binding using EMSA and RNA-seq analysis. The results showed that BlnR positively regulates balanol biosynthesis through binding to all promoters of bln gene members, including its own promoter. Microscopic observation revealed blnR overexpression also affected spore development and hypha growth. Furthermore, RNA-seq analysis suggested that BlnR can regulate other genes outside of the balanol biosynthetic gene cluster, including those involved in conidiospore development. Finally, balanol production was further improved to 2187.39 mg/L using the optimized medium through statistical optimization based on response surface methodology.
2. Revelation of the Balanol Biosynthetic Pathway in Tolypocladium ophioglossoides
Xian He, Min Zhang, Yuan-Yang Guo, Xu-Ming Mao, Xin-Ai Chen, Yong-Quan Li Org Lett. 2018 Oct 19;20(20):6323-6326. doi: 10.1021/acs.orglett.8b01543. Epub 2018 Oct 2.
A cryptic gene cluster, bln, was activated by genome mining in Tolypocladium ophioglossoides. This activation led to the production of balanol and eight other metabolites. Gene disruption and metabolite profile analysis showed that the biosynthesis of balanol involved the convergence of independent PKS and NRPS pathways, and a biosynthetic pathway for balanol was proposed.
3. Comprehensive Account on the Synthesis of (-)-Balanol and its Analogues
Sajjad Ahmad, Rabia Akhtar, Ameer Fawad Zahoor Curr Org Synth. 2022;19(1):56-85. doi: 10.2174/1570179418666210809131917.
Background: A variety of diseases have been associated with hyperactivation of protein kinase C (PKC) enzymes such as cancer, diabetes, asthma, cardiovascular and central nervous system disorders. There is a dire need to selectively inhibit these enzymes by synthesizing new potent inhibitors. Balanol, a fungal metabolite belonging to the PKC inhibitor family, is especially included in this aspect. Tremendous effort has been put towards the synthesis of balanol by different research groups. Objectives: The aim of this review is to provide a detailed description of synthetic approaches adopted for the synthesis of key fragments of balanol (azepane and benzophenone). All the factors that resulted in excellent yield and high enantioselectivity have also been mentioned. Conclusion: It has been shown throughout this review that the synthesis of hexahydroazepine and benzophenone cores of balanol was achieved by employing a variety of important key steps with commercially available starting precursors, which make this total synthesis more valuable. Moreover, this article provides ideas to the synthetic as well as pharmaceutical chemists for the synthesis of (-)-balanol and its analogues.
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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 ╳
