Alphitonin
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| Category | Others |
| Catalog number | BBF-04666 |
| CAS | 493-36-7 |
| Molecular Weight | 304.25 |
| Molecular Formula | C15H12O7 |
| Purity | >95% by HPLC |
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Description
Alphitonin is a metabolite related to flavonoids, which is isolated from the heartwood of Australian red ash. Alphitonin has anti-diabetic and anti-oxidant effects.
Specification
| Storage | Store at -20°C |
| IUPAC Name | 2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-1-benzofuran-3-one |
| Canonical SMILES | C1=CC(=C(C=C1CC2(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O |
| InChI | InChI=1S/C15H12O7/c16-8-4-11(19)13-12(5-8)22-15(21,14(13)20)6-7-1-2-9(17)10(18)3-7/h1-5,16-19,21H,6H2 |
| InChI Key | VCLACNNZBMRRES-UHFFFAOYSA-N |
Properties
| Boiling Point | 678.0±55.0°C at 760 mmHg |
| Density | 1.8±0.1 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. The in vitro and in vivo anti-inflammatory activities of alphitonin-4-O-β-D-glucopyranoside
Nguyen Quoc Vuong, Vu Van Chien, Do Thi Thao, Nguyen Thi Nga, Do Thi Phuong, Pham Van Cuong, Nguyen Tien Dat Nat Prod Res. 2018 Nov;32(22):2717-2719. doi: 10.1080/14786419.2017.1374272. Epub 2017 Sep 13.
The anti-inflammatory compound, alphitonin-4-O-β-D-glucopyranoside (1), has previously been isolated in the leaves of Artokapus tonkinensis and synthesised from taxifolin. This study aimed to investigate the inhibitory effect of this compound on inflammatory cytokines, including tumour necrosis factor-alpha (TNF-α), interleukin (IL)-1, IL-6 and IL-10, in RAW264.7 macrophages and in an arthritis animal model. Compound 1 dose-dependently decreased the production of TNF-α, IL-1 and IL-6 in lipopolysaccharide-stimulated RAW264.7 cells. In contrast, the level of anti-inflammatory IL-10 increased. In a collagen antibody-induced arthritis BALB/c mouse model, compound 1 at a dose of 125 and 250 mg/kg body weight significantly decreased arthritis incidence in comparison with dexamethasone.
2. Structural Basis for (2 R,3 R)-Taxifolin Binding and Reaction Products to the Bacterial Chalcone Isomerase of Eubacterium ramulus
Gottfried J Palm, Maren Thomsen, Leona Berndt, Winfried Hinrichs Molecules. 2022 Nov 16;27(22):7909. doi: 10.3390/molecules27227909.
The bacterial chalcone isomerase (CHI) from Eubacterium ramulus catalyses the first step in a flavanone-degradation pathway by a reverse Michael addition. The overall fold and the constitution of the active site of the enzyme completely differ from the well-characterised chalcone isomerase of plants. For (+)-taxifolin, CHI catalyses the intramolecular ring contraction to alphitonin. In this study, Fwe perform crystal structure analyses of CHI and its active site mutant His33Ala in the presence of the substrate taxifolin at 2.15 and 2.8 Å resolution, respectively. The inactive enzyme binds the substrate (+)-taxifolin as well defined, whereas the electron density maps of the native CHI show a superposition of substrate, product alphitonin, and most probably also the reaction intermediate taxifolin chalcone. Evidently, His33 mediates the stereospecific acid-base reaction by abstracting a proton from the flavonoid scaffold. The stereospecificity of the product is discussed.
3. Novel Catabolic Pathway of Quercetin-3- O-Rutinose-7- O-α-L-Rhamnoside by Lactobacillus plantarum GDMCC 1.140: The Direct Fission of C-Ring
Guitao Huang, Mingwen Lai, Canhua Xu, Shan He, Lihong Dong, Fei Huang, Ruifen Zhang, David James Young, Hesheng Liu, Dongxiao Su Front Nutr. 2022 Mar 16;9:849439. doi: 10.3389/fnut.2022.849439. eCollection 2022.
Lychee pulp phenolics (LPP) is mainly catabolized in the host colon, increasing the abundances of Bacteroides and Lactobacillus. Herein, five selected gut microbial strains (Bacteroides uniformis, B. thetaiotaomicron, Lactobacillus rhamnosus, L. plantarum, and L. acidophilus) were separately incubated with LPP to ascertain the specific strains participating in phenolic metabolism and the corresponding metabolites. The results indicated that B. uniformis, L. rhamnosus, and L. plantarum were involved in LPP utilization, contributing to 52.37, 28.33, and 45.11% of LPP degradation after 48 h fermentation, respectively. Unprecedentedly, the metabolic pathway of the major phenolic compound quercetin-3-O-rutinose-7-O-α-L-rhamnoside by L. plantarum, appeared to be the direct fission of C-ring at C2-O1 and C3-C4 bonds, which was proved from the occurrence of two substances with the deprotonated molecule [M-H]- ion at m/z 299 and 459, respectively. Meanwhile, it was fully confirmed that B. uniformis participated in the catabolism of isorhamnetin glycoside and procyanidin B2. In the B. uniformis culture, kaempferol was synthesized through dehydroxylation of quercetin which could be catabolized into alphitonin by L. rhamnosus. Furthermore, LPP metabolites exerted higher antioxidant activity than their precursors and gave clues to understand the interindividual differences for phenolic metabolism by gut microbiota.
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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 ╳
