Dihydrochalcones and homoisoflavanes from the red resin of Dracaena cochinchinensis (Chinese dragon's blood)

Fitoterapia. 2014 Dec:99:64-71. doi: 10.1016/j.fitote.2014.09.006. Epub 2014 Sep 16.

Abstract

Two new dihydrochalcones, 4-hydroxy-2,4'-dimethoxydihydrochalcone (1) and 3,4'-dihydroxy-2,4,6-trimethoxydihydrochalcone (2), and a new homoisoflavane, 7,3'-dihydroxy-8,4'-dimethoxyhomoisoflavane (3), along with 12 known compounds (4-15), were isolated from the red resin of Dracaena cochinchinensis (Chinese dragon's blood). Their structures were assigned by a variety of spectroscopic techniques. Diversity of cleavage pathways were proposed for dihydrochalcones and homoisoflavanes based on the mass spectroscopic behaviors of those identified compounds using hybrid ion trap-time of flight mass spectrometry. All the compounds were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages, and compound 9 exhibited mild inhibition of NO production in this assay with IC₅₀ value of 50.3 μM.

Keywords: 2,4,4′-trihydroxydihydrochalcone (PubChem CID: 10801179); Chinese dragon's blood; Dihydrochalcone; Dracaena cochinchinensis; Homoisoflavane; Loureirin A (PubChem CID: 5319081); Loureirin B (PubChem CID: 189670); Loureirin C (PubChem CID: 14157896); Loureirin D (PubChem CID: 13939318); Mass fragmentation pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Cell Line
  • Chalcones / chemistry*
  • Chalcones / isolation & purification
  • Dracaena / chemistry*
  • Isoflavones / chemistry*
  • Isoflavones / isolation & purification
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / metabolism
  • Resins, Plant / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Chalcones
  • Isoflavones
  • Resins, Plant
  • Nitric Oxide
  • dihydrochalcone