New Pinane Derivatives Found in Essential Oils of Calocedrus decurrens

Molecules. 2017 Jun 2;22(6):921. doi: 10.3390/molecules22060921.

Abstract

The main objective of this study was to determine the chemical composition of essential oils (EOs) obtained from leaf, old branches, and young branches of a coniferous species Calocedrus decurrens acclimated to Corsica. The analytical investigation was conducted by GC(RI), GC-MS, pc-GC, and NMR. C. decurrens leaf, old branches, and young branches EOs contained α-pinene (11.2; 56.6; 22.3%), myrcene (13.4; 8.4; 9.7%), Δ-3-carene (31.3; 5.2; 11.1%), limonene (6.4; 5.1; 5.5%), terpinolene (6.9; 1.5; 3.2%), and pin-2-en-8-ol (4.2; 4.5; 10.4%) as major components, respectively. Special attention was paid to purifying and identifying four unusual pinane derivatives: pin-2-en-8-ol, pin-2-en-8-yl Acetate, pin-2-en-8-al, and methyl pin-2-en-8-oate. The last two are reported for the first time.

Keywords: 2D-NMR; Calocedrus decurrens; methyl pin-2-en-8-oate; pin-2-en-8-al; pin-2-en-8-ol; pin-2-en-8-yl Acetate; structural elucidation.

MeSH terms

  • Bicyclic Monoterpenes
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cupressaceae / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Oils, Volatile / chemistry*
  • Plant Leaves / chemistry
  • Plant Oils / chemistry*
  • Terpenes / chemistry*

Substances

  • Bicyclic Monoterpenes
  • Oils, Volatile
  • Plant Oils
  • Terpenes
  • pinane