- Enantioselective Synthesis of 2′- and 3′-Substituted Natural Flavans by Domino Asymmetric Transfer Hydrogenation/Deoxygenation
-
A concise and highly enantioselective synthesis of the natural flavans kazinol U and (2S)-7,3′-dihydroxy-4′-methoxyflavan is reported for the first time. The key transformation is a single-step conversion of a racemic flavanone to a flavan by means of an asymmetric transfer hydrogenation/deoxygenation cascade with kinetic resolution.
- Ke?berg, Anton,Metz, Peter
-
-
Read Online
- Application of flavan compounds in preparation of anti-tumor drugs
-
The invention discloses application of a flavan compound in preparation of an anti-tumor drug.
- -
-
Paragraph 0110-0112
(2021/10/20)
-
- Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) in Vitro
-
Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 μM to 100 μM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 20,4,40,60-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 μM and 100 μM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.
- Hans, Joachim,Ley, Jakob P.,Pfeiffer, Stefanie,Schueller, Katharina,Somoza, Veronika,Walker, Jessica
-
-
- USE OF HYDROXYFLAVAN DERIVATIVES FOR TASTE MODIFICATION
-
The present invention primarily relates to the use of specific compounds of formula (I) or of specific salts of a compound of formula (I) or mixtures thereof for synergistically enhancing the sweet taste of a sweet-tasting substance.
- -
-
-
- Studies on flavans. III. The total synthesis of (±)-7,4′ -dihydroxy-3′-methoxyflavan, (±)-7,3′-dihydroxy-4′ -methoxyflavan, and (±)-7,4′-dihdroxyflavan
-
The first total synthesis of (±)-7,3′-dihydroxy-4′ -methoxyflavan (1) and (±)-7,4′-dihydroxy-3′-methoxyflavan (2), along with the synthesis of (±)-7,4′-dihydroxyflavan (3), three naturally occurring flavans, were described. The key step is the cyclization of 1,3-diaryl-1-propanol by BF3·Et2O.
- Xue, Jijun,Zhang, Xianshu,Chen, Xuesong,Zhang, Yingpeng,Li, Ying
-
p. 3527 - 3536
(2007/10/03)
-
