Urolithin is a metabolite of a class of compounds known as polyphenols which are found in various fruits, including pomegranates, nuts and strawberries. Urolithin is a biologically-active compound which has anti-inflammatory, antioxidant and anticancer properties. Our laboratory has focused on the use of a palladium-catalyzed intramolecular biaryl coupling reaction to yield urolithin C 3-glucuronide (uro-C 3-glur).The total synthesis of uro-C 3-glur has been accomplished in 11 steps starting from the commercially-available 3,4-dimethoxybenzaldehyde. We now report full details of the total synthesis of urolithin C 3-glucuronide (1).Over recent years, it has been reported that gastrointestinal microbiota metabolize xenobiotics, which are produced from natural products, 1 i.e., urolithins, which are hydroxylated dibenzo [b,d]pyran-6-one derivatives, contain urolithin A (uro-A), urolithin B (uro-B), urolithin C (uro-C) and urolithin D (uro-D) derivatives which are produced in vivo by the gastrointestinal microbiota of humans and different animals upon intaking ellagitannins (ETs), which are high molecular weight polyphenols and ellagic acids (EAs) [2][3][4][5][6][7]. There are many different phenolic antioxidants, such as ETs and EAs, in walnuts and pomegranates, which have been linked to potential preventive effects against chronic diseases like Figure. Structures of urolithins A-D
We present a total synthesis of hyalodendriol C, a fungal natural product. We have focused on the use of palladium-catalyzed intramolecular biaryl coupling reaction of phenyl benzoate derivatives to synthesize hyalodendriol C. Keeping in view, the indispensable biological values of this compound, we took the advantage of our established strategy to chemically synthesize hyalodendriol C. The total synthesis of hyalodendriol C got accomplished in 10 steps beginning with the preparation of phenol derivative from the commercially available 5-methylbenzene-1,3-diol and synthesis of the corresponding benzoic acid derivative.Hyalodendriol C 1 as indicated in Figure 1, chemically named as (2-chloro-7,9-dihydroxy-3-methoxy-1methyl-6H-dibenzo [b,d]pyran-6-one), is a naturally occurring dibenzo--pyrones 2 and possesses a fused tricyclic nucleus. In 2016, Zhou and co-workers reported the isolation and structural elucidation of hyalodendriols A-C from endophytic fungus associated with the hybrid 'Neva of Populus deltoides' x P. nigra L. 1 A variety of biological activities have been stated for hyalodendriols A-C, but only hyalodendriol C has shown strong antibacterial, larvicidal, and antifungal properties as mentioned previously in the literature. 1 Particularly, it has shown strong antifungal effects with a value of IC50 of 11.6 µg mL −1 in opposition to the spore germination of Magnaporthe oryzae. It has also exhibited strong larvicidal activities in the case of the yellow fever mosquito that is known to spread severe diseases like Zika fever, dengue fever, chikungunya, and many other health problems. Conversely, hyalodendriols A and B which do not possess chloro substituents, exhibited weaker activities. Several natural products that possess 6H-dibenzo [b,d]pyran-6-one moiety are found to exhibit numerous biological activities. 3 Among the varied biological activities of these compounds, the most exciting bioactivity is anti-cancer activity against the SW1116 cell lines. The interesting structural feature of this compound is the aromatic ring
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