Aromatic and Aliphatic Apiuronides from the Bark of Cinnamomum cassia

J Nat Prod. 2021 Mar 26;84(3):553-561. doi: 10.1021/acs.jnatprod.0c01062. Epub 2021 Mar 8.

Abstract

Cinnamomum cassia Presl (Cinnamon) has been widely cultivated in the tropical or subtropical areas, such as Yunnan, Fujian, Guandong, and Hainan in China, as well as India, Vietnam, Thailand, and Malaysia. Four new glycosides bearing apiuronic acid (1, 4, 6, and 7) and their sodium or potassium salts (2, 3, and 5), together with 31 known compounds, were isolated from a hot water extract of the bark of C. cassia via repeated chromatography. The structures of the new compounds (1-7) were determined by NMR, IR, MS, and ICP-AES data and by acid hydrolysis and sugar analysis. This is the first report of the presence of apiuronic acid glycosides. Some of the isolates were evaluated for their analgesic effects on a neuropathic pain animal model induced by paclitaxel. Cinnzeylanol (8), cinnacaside (9), kelampayoside A (10), and syringaresinol (11) showed analgesic effects against paclitaxel-induced cold allodynia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Analgesics / isolation & purification
  • Analgesics / pharmacology*
  • Animals
  • Cinnamomum aromaticum / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Molecular Structure
  • Neuralgia / drug therapy*
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Plant Bark / chemistry
  • Republic of Korea

Substances

  • Analgesics
  • Glycosides
  • Phytochemicals