Bornyl-diphosphate synthase from Lavandula angustifolia: A major monoterpene synthase involved in essential oil quality

Phytochemistry. 2017 May:137:24-33. doi: 10.1016/j.phytochem.2017.01.015. Epub 2017 Feb 9.

Abstract

Lavender essential oils (EOs) of higher quality are produced by a few Lavandula angustifolia cultivars and mainly used in the perfume industry. Undesirable compounds such as camphor and borneol are also synthesized by lavender leading to a depreciated EO. Here, we report the cloning of bornyl diphosphate synthase of lavender (LaBPPS), an enzyme that catalyzes the production of bornyl diphosphate (BPP) and then by-products such as borneol or camphor, from an EST library. Compared to the BPPS of Salvia officinalis, the functional characterization of LaBPPS showed several differences in amino acid sequence, and the distribution of catalyzed products. Molecular modeling of the enzyme's active site suggests that the carbocation intermediates are more stable in LaBPPS than in SoBPPS leading probably to a lower efficiency of LaBPPS to convert GPP into BPP. Quantitative RT-PCR performed from leaves and flowers at different development stages of L. angustifolia samples show a clear correlation between transcript level of LaBPPS and accumulation of borneol/camphor, suggesting that LaBPPS is mainly responsible of in vivo biosynthesis of borneol/camphor in fine lavender. A phylogenetic analysis of terpene synthases (TPS) pointed out the basal position of LaBPPS in the TPSb clade, suggesting that LaBPPS could be an ancestor of others lavender TPSb. Finally, borneol could be one of the first monoterpenes to be synthesized in the Lavandula subgenus. Knowledge gained from these experiments will facilitate future studies to improve the lavender oils through metabolic engineering or plant breeding. Accession numbers: LaBPPS: KM015221.

Keywords: Camphor; Lavandula angustifolia (Lamiaceae); Terpene synthase; Transcript regulation.

MeSH terms

  • Alkyl and Aryl Transferases / genetics
  • Alkyl and Aryl Transferases / metabolism
  • Amino Acid Sequence
  • Camphanes / chemistry
  • Camphor / chemistry
  • Catalytic Domain
  • Cloning, Molecular
  • Flowers / enzymology
  • Intramolecular Lyases / genetics
  • Intramolecular Lyases / metabolism*
  • Lavandula / enzymology*
  • Models, Molecular
  • Oils, Volatile / chemistry*
  • Phylogeny
  • Plant Leaves / enzymology
  • Plant Oils / chemistry*
  • Plant Proteins / genetics
  • Plant Proteins / metabolism*
  • Salvia officinalis / enzymology
  • Structure-Activity Relationship

Substances

  • Camphanes
  • Oils, Volatile
  • Plant Oils
  • Plant Proteins
  • Camphor
  • Alkyl and Aryl Transferases
  • terpene synthase
  • Intramolecular Lyases
  • pinene cyclase I
  • geranyl-diphosphate cyclase
  • lavender oil