Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia

J Nat Prod. 2014 Aug 22;77(8):1948-54. doi: 10.1021/np500465g.

Abstract

Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-D-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5-10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1-4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cinnamomum aromaticum / chemistry*
  • Concanavalin A / pharmacology
  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / immunology*
  • Diterpenes / isolation & purification*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / immunology*
  • Immunosuppressive Agents / isolation & purification*
  • Mice
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • T-Lymphocytes / drug effects

Substances

  • 16-O-beta-D-glucopyranosyl-19-deoxycinncassiol G
  • 18-hydroxyperseanol
  • Diterpenes
  • Drugs, Chinese Herbal
  • Immunosuppressive Agents
  • cinncassiol F
  • cinncassiol G
  • Concanavalin A