90729-87-6Relevant articles and documents
Aaph or peroxynitrite‐induced biorelevant oxidation of methyl caffeate yields a potent antitumor metabolite
Fási, Laura,Latif, Ahmed Dhahir,Zupkó, István,Lévai, Sándor,Dékány, Miklós,Béni, Zoltán,K?ncz?l, árpád,Balogh, Gy?rgy Tibor,Hunyadi, Attila
, p. 1 - 13 (2020)
Hydroxycinnamic acids represent a versatile group of dietary plant antioxidants. Oxidation of methyl‐p‐coumarate (pcm) and methyl caffeate (cm) was previously found to yield potent antitumor metabolites. Here, we report the formation of potentially bioactive products of pcm and cm oxidized with peroxynitrite (ONOOˉ), a biologically relevant reactive nitrogen species (RNS), or with α,α′‐azodiisobutyramidine dihydrochloride (AAPH) as a chemical model for reactive oxygen species (ROS). A continuous flow system was developed to achieve reproducible in situ ONOOˉ formation. Reaction mixtures were tested for their cytotoxic effect on HeLa, SiHa, MCF‐7 and MDA‐MB‐231 cells. The reaction of pcm with ONOOˉ produced two fragments, an o‐ nitrophenol derivative, and a new chlorinated compound. Bioactivity‐guided isolation from the reaction mixture of cm with AAPH produced two dimerization products, including a dihydrobenzofuran lignan that exerted strong antitumor activity in vitro, and has potent in vivo antimetastatic activity which was previously reported. This compound was also detected from the reaction between cm and ONOOˉ. Our results demonstrate the ROS/RNS dependent formation of chemically stable metabolites, including a potent antitumor agent (5), from hydroxycinnamic acids. This suggests that diversity‐oriented synthesis using ROS/RNS to obtain oxidized antioxidant metabolite mixtures may serve as a valid natural product‐based drug discovery strategy.
Total synthesis of Carpatamides A–D
Madala, Nagaraju,Ghanta, Venkata Rao,Vinnakota, Srilalitha,Mendu, Narender,Ingle, Arun B.,Ethiraj, Krishna,Sharma, Vishal
supporting information, p. 2708 - 2710 (2018/06/20)
A synthetic strategy was developed for the synthesis of the common core structure of Carpatamides A–D. The total synthesis of Carpatamides A and C was completed in 6 steps and of Carpatamides B and D in 7 steps, by employing the Wittig olefination, olefin