Cytotoxicity of labdane-type diterpenoids from Hedychium forrestii

Chem Pharm Bull (Tokyo). 2008 Feb;56(2):210-2. doi: 10.1248/cpb.56.210.

Abstract

Two new labdane-type diterpenoids, hedyforrestin D (1) and 15-ethoxy-hedyforrestin D (2), and three known compounds, yunnancoronarin A (4), B (3) and C (5) were isolated from the rhizomes of Hedychium forrestii. The structure of the new diterpenoids was established as 6beta,15xi-dihydroxylabda-8(17),11,13-trien-15,16-olide (1), and 6beta-hydroxy-15xi-ethoxylabda-8(17),11,13-trien-15,16-olide (2) on the basis of spectroscopic analyses. In addition, the isolated compounds were evaluated for their cytotoxicity against the lung adenocarcinoma cells A549 and leukemia cells K562 through 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assays. Of these, compounds 3 and 4 exhibited the most activity with IC(50) values of 0.92 and 2.20 microM, respectively, whereas 5 was inactive against A549 cells and 1 was inactive against both cell lines up to a concentration of 300.81 microM. This shows that both the hydroxy substitution and orientation of unsaturated lactone group in the five-membered ring of C-13 to C-16 seem to play an important role in the anti-tumor activities of human lung adenocarcinoma and leukemia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • K562 Cells
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship
  • Tetrazolium Salts
  • Thiazoles
  • Zingiberaceae / chemistry*

Substances

  • 15-ethoxy-hedyforrestin D
  • Antineoplastic Agents, Phytogenic
  • Diterpenes
  • Tetrazolium Salts
  • Thiazoles
  • hedyforrestin D
  • labdane
  • thiazolyl blue