title: Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity.
abstract: A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cells. From this we have shown that all properties can be modulated independently by varying ring size and by moving the ester out of conjugation with the biaryl ring system. Increasing ring size increased redox activity and cytotoxicity, leading to the identification of a compound (10) which was significantly more cytotoxic. In addition compounds identified with a redox active scaffold and low cytotoxicity may be employed as a new class of redox probes.
authors.affiliation: Institute of Pesticide Science, Northwest A&F University, 22 Xinong Road, Yangling, Shaanxi 712100, China.
authors.forename: Shaojun
authors.initials: S
authors.lastname: Zheng
authors.forename: Luca
authors.initials: L
authors.lastname: Laraia
authors.forename: Cornelius J
authors.initials: CJ
authors.lastname: O' Connor
authors.forename: David
authors.initials: D
authors.lastname: Sorrell
authors.forename: Yaw Sing
authors.initials: YS
authors.lastname: Tan
authors.forename: Zhaochao
authors.initials: Z
authors.lastname: Xu
authors.forename: Ashok R
authors.initials: AR
authors.lastname: Venkitaraman
authors.forename: Wenjun
authors.initials: W
authors.lastname: Wu
authors.forename: David R
authors.initials: DR
authors.lastname: Spring
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D010641:Phenotype; D013329:Structure-Activity Relationship
chemical_list: D005960:Glucosides; D005707:Gallic Acid; C087926:tellimagrandin I