Cytotoxic dehydromonacolins from red yeast rice

Lin Zhu, Lee Fong Yau, Jing Guang Lu, Guo Yuan Zhu, Jing Rong Wang, Simon Q B HAN, Wendy W L HSIAO, Zhi Hong JIANG*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

Two new dehydromonacolins (1 and 3), together with nine known monacolins (4-12), were isolated from red yeast rice. Compounds 4-6 were isolated from a natural resource for the first time. Their structures were elucidated by means of NMR and mass spectroscopic analyses. The structure of dehydromonacolin N (1) was further confirmed by its semisynthesis from monacolin K (lovastatin) (11). Dehydromonacolin J (2), an intermediate in the semisynthesis of 1, was obtained as a new dehydromonacolin. The structure of dehydromonacolin L (3) was also confirmed by an elimination reaction of monacolin L (12). Compound 1, possessing a C2 side chain, is unprecedented in the natural monacolin family and exhibited moderate cytotoxic activity against Hep G2, Caco-2, and MCF-7 cancer cell lines. Dehydromonacolin K (8) demonstrated the most potent cytotoxicity to all three of these cell lines. The structure-activity relationship of natural and synthesized monacolins was discussed. This is the first report on the cytotoxic effects of dehydromonacolins.

Original languageEnglish
Pages (from-to)934-939
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume60
Issue number4
DOIs
Publication statusPublished - 1 Feb 2012

Scopus Subject Areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

User-Defined Keywords

  • cytotoxicity
  • monacolins
  • Monascus
  • red yeast rice

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