Dibefurin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-01386 |
| CAS | |
| Molecular Weight | 360.31 |
| Molecular Formula | C18H16O8 |
Online Inquiry
Description
Dibefurin is produced by the strain of AB16501-759. The inhibition of neurocalcitonin phosphatase was 16μg/mL, the inhibition of mixed lymphocyte reaction was 2.5 μg/mL, and the bioassay of lymphocytotoxicity was 33.0 μg/mL.
Specification
| IUPAC Name | 2,10-dihydroxy-4,12-dimethyl-7,15-dioxapentacyclo[8.6.1.12,9.01,13.05,9]octadeca-4,12-diene-3,11,17,18-tetrone |
| Canonical SMILES | CC1=C2COCC23C(=O)C(C1=O)(C45COCC4=C(C(=O)C3(C5=O)O)C)O |
| InChI | InChI=1S/C18H16O8/c1-7-9-3-25-5-15(9)13(21)17(23,11(7)19)16-6-26-4-10(16)8(2)12(20)18(15,24)14(16)22/h23-24H,3-6H2,1-2H3 |
| InChI Key | QMHFCPLGUKRQDC-UHFFFAOYSA-N |
Reference Reading
1. Complex Natural Products Derived from Pyrogallols
Alexander J E Novak, Dirk Trauner Prog Chem Org Nat Prod. 2022;118:1-46. doi: 10.1007/978-3-030-92030-2_1.
Pyrogallols (1,2,3-trihydroxybenzenes) are abundant in Nature, easily oxidized, and are central precursors to important natural products. The rich chemistry of their oxidized derivatives, the hydroxy-o-quinones, has been studied for over a century and still attracts the interest of the scientific community. Only in the last ten years have critical insights of pyrogallol chemistry from the mid-twentieth century been applied to modern natural product synthesis. Historical studies of pyrogallol chemistry, including [5+2], [4+2], and formal [5+5] cycloadditions are discussed here and reactivity guidelines established. The application and remarkable selectivity of these cycloadditions is then showcased in the recent syntheses of several fungal natural products, including dibefurin, epicolactone, the merocytochalasans, and preuisolactone A. The authors hope that this contribution will spark further interest in the fascinating chemistry of pyrogallols and natural products derived from them.
2. Biomimetic synthesis of the calcineurin phosphatase inhibitor dibefurin
Pascal Ellerbrock, Nicolas Armanino, Dirk Trauner Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13414-8. doi: 10.1002/anie.201407088. Epub 2014 Nov 4.
Dibefurin is a Ci -symmetric natural product that acts as an inhibitor of calcineurin phosphatase. A six-step synthesis of this compound is reported, which features an oxidative dimerization of the aromatic polyketide epicoccine as the key step. Dibefurin is proposed to be related to epicolactone, a complex yet racemic fungal metabolite that has recently been discovered. Attempts to access epicolactone from epicoccine and epicoccone B resulted in an unusual dimer that is formed through a hetero-Diels-Alder reaction of a para-quinone methide with an ortho-quinone.
3. Secondary Metabolites with α-Glucosidase Inhibitory Activity from the Mangrove Fungus Mycosphaerella sp. SYSU-DZG01
Pei Qiu, Zhaoming Liu, Yan Chen, Runlin Cai, Guangying Chen, Zhigang She Mar Drugs. 2019 Aug 20;17(8):483. doi: 10.3390/md17080483.
Four new metabolites, asperchalasine I (1), dibefurin B (2) and two epicoccine derivatives (3 and 4), together with seven known compounds (5-11) were isolated from a mangrove fungus Mycosphaerella sp. SYSU-DZG01. The structures of compounds 1-4 were established from extensive spectroscopic data and HRESIMS analysis. The absolute configuration of 1 was deduced by comparison of ECD data with that of a known structure. The stereostructures of 2-4 were further confirmed by single-crystal X-ray diffraction. Compounds 1, 8 and 9 exhibited significant α-glucosidase inhibitory activity with IC50 values of 17.1, 26.7 and 15.7 μM, respectively. Compounds 1, 4, 6 and 8 showed antioxidant activity by scavenging DPPH· with EC50 values ranging from 16.3 to 85.8 μM.
Recommended Products
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03754 | Castanospermine | Inquiry |
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 ╳
