Two new diterpenoids from kencur (Kaempferia galanga): Structure elucidation and chemosystematic significance

Abdelsamed I. Elshamy, Tarik A. Mohamed, Ningombam Swapana, Rania F. Ahmed, Tatsuro Yoneyama, Paul W. Paré, Masaaki Noji, Mohamed Elamir F. Hegazy, Akemi Umeyama

Research output: Contribution to journalArticlepeer-review

Abstract

Aromatic ginger or kencur (Kaempferia galanga L.) rhizomes are ground as a spice or pickled for consumption in south-east Asian cuisines; although widely used, until recently it has been less studied chemically than white and red ginger. Hydro-distillate extracts have identified several compounds that exhibit anticancer activity against select tumor cell lines in vitro, and most recently chemical analyses have focused on rhizome metabolites present in organic extracts. Here we report on two new diterpenoids including Δ8(14),15 polyhydroxlated isopimardienes, 1α-hydroperoxy-2α,6,7-trihydroxy-isopimara-6(7),8(14),15-triene (kaemgalangol E; 1) and 1α,7β-hydroxy-isopimara-8(14),15-diene (kaemgalangol F; 2), along with the known compound, marginaol A (3) from a CH2Cl2/MeOH extract of the rhizome. Structural elucidation was based on spectroscopic analysis including HRMS, FTIR, as well as 1D and 2D NMR. A proposed biosynthetic pathway for compounds 1–3 is presented and chemo-systematic analysis indicates that K. galanga has the enzymatic machinery to synthesize an array of Δ8(14),15 isopimardienes as well as methoxylated cinnamates.

Original languageEnglish
Pages (from-to)185-189
Number of pages5
JournalPhytochemistry Letters
Volume44
DOIs
StatePublished - Aug 2021

Keywords

  • Chemo-systematic evaluation
  • Diterpenes
  • Kencur
  • Polyhydroxlated isopimardiene
  • Zingiberaceae

Fingerprint

Dive into the research topics of 'Two new diterpenoids from kencur (Kaempferia galanga): Structure elucidation and chemosystematic significance'. Together they form a unique fingerprint.

Cite this