Neolignans and Diarylheptanoids with Anti-Inflammatory Activity from the Rhizomes of Alpinia zerumbet

Yan Zhang, Yuan Yuan Yu, Fei Peng, Wen Tao Duan, Chuan Hai Wu, Hao Tian Li, Xu Fu Zhang*, Yu Sheng Shi*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

9 Citations (Scopus)

Abstract

The dried leaves and rhizomes of Alpinia zerumbet have been traditionally used as food and medicine. Anti-inflammatory activity-guided phytochemical investigation into the rhizomes of A. zerumbet led to the isolation of 17 compounds including 10 neolignans (1-10, 1a, 1b, 2a, 2b, 3a, 3b, 4, and 5 are new compounds) and seven diarylheptanoids (11-17) in which 1-3 were three pairs of enantiomers. 4 was only one enantiomer and 5 was a racemic mixture. Compounds 1a, 1b, 2a, and 2b incorporated an 8′,9′-dinorneolignan skeleton, which was rare in the lignan family. The planar structures of these compounds were elucidated by extensive analyses of spectroscopic data. The relative and absolute configurations were determined by the time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculation method. The 95% ethanol extract and ethyl acetate extract of A. zerumbet were found to show anti-inflammatory activity against croton oil-induced ear edema in mice with inhibition rates of 20.0 and 47.6% at a dose of 80 mg/kg, respectively. Bioassays showed that compounds 1a, 1b, 2a, 2b, and 12 moderately inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC50 values of 3.62, 7.63, 6.51, 5.60, and 8.33 μM, respectively.

Original languageEnglish
Pages (from-to)9229–9237
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume69
Issue number32
DOIs
Publication statusPublished - 18 Aug 2021

Scopus Subject Areas

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

User-Defined Keywords

  • Alpinia zerumbet
  • anti-inflammatory activity
  • diarylheptanoids
  • neolignans

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