In Vitro and in Vivo Evidence for RNA Adduction Resulting from Metabolic Activation of Methyleugenol

Xiaojing Yang, Yukun Feng, Zhengyu Zhang, Hui Wang, Weiwei Li, Dan Ohtan Wang, Ying Peng, Jiang Zheng

Research output: Contribution to journalArticlepeer-review


Methyleugenol (ME) is a ubiquitous component in spices and other culinary herbal products. A prevailing theory in ME toxicity is its ability to be metabolically activated by P450 enzymes and sulfotransferases, which initiates sequential reactions of the resulting metabolites with functional biomolecules. The present study aimed at a potential interaction between the reactive metabolites of ME and RNA. Cultured mouse primary hepatocytes were incubated with ME followed by RNA extraction and NaOH and alkaline phosphatase-based RNA hydrolysis. Three adenosine adducts were detected in the hydrolytic mixture by LC-MS/MS. The same adenosine adducts were also detected in hepatic tissues harvested from ME-treated mice. These three adducts were chemically synthesized and structurally characterized by 1H NMR. Additionally, two guanosine adducts and one cytidine adduct were detected in the in vivo samples. These results provided solid evidence that the reactive metabolites of ME attacked RNA, resulting in RNA adduction.

Original languageEnglish (US)
Pages (from-to)15134-15141
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Issue number51
StatePublished - Dec 23 2020


  • LC-MS/MS
  • metabolic activation
  • methyleugenol
  • RNA adduction

ASJC Scopus subject areas

  • General Chemistry
  • General Agricultural and Biological Sciences


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