Biochemistry of lactone formation in yeast and fungi and its utilisation for the production of flavour and fragrance compounds

Abstract

The consumers' demand for natural flavour and fragrances rises. To be natural, compounds have to result from the extraction of natural materials and/or to be transformed by natural means such as the use of enzymes or whole cells. Fungi are able to transform some fatty acids into lactones that can thus be natural. Although some parts of this subject have been reviewed several times, the present article proposes to review the different pathways utilised, the metabolic engineering strategies and some current concerns on the reactor application of the transformation including scaling up data. The main enzymatic steps are hydroxylation and β-oxidation in the traditional way, and lactone desaturation or Baeyer-Villiger oxidation. Although the pathway to produce γ-decalactone is rather well known, metabolic engineering strategies may result in significant improvements in the productivity. For the production of other lactones, a key step is the hydroxylation of fatty acids. Beside the biotransformation, increasing the production of the various lactones requires from biotechnologists to solve two main problems which are the toxicity of lactones toward the producing cell and the aeration of the emulsified reactor as the biochemical pathway is very sensitive to the level of available oxygen. The strategies employed to resolve these problems will be presented.

Amphiphilic block copolymers from a renewable ε-decalactone monomer: prediction and characterization of micellar core effects on drug encapsulation and release

“…Here we show that ε-decalactone (ε-DL, see Figure 1) is a good alternative to ε-caprolactone as a biomedical monomer because; (a) the (ε-DL) monomer is derived from a sustainable source, i.e. castor oil, (b) it has already been commercially adopted in the flavouring and fragrance industries, 34,35 and (c) the pendent butyl groups are predicted to disrupt the chain packing of PεDL chains, so promoting the desired amorphous character within the poly(ε-decalactone) (PεDL) core structures to enhance drug loading. 36 We thus describe the synthesis of novel mPEG-b-PεDL block copolymers and determine the efficiency of drug loading and the release profiles of drugs from mPEG-b-PεDL micelles.…”

New Biotransformation Process for Production of the Fragrant Compound γ-Dodecalactone from 10-Hydroxystearate by Permeabilized Waltomyces lipofer Cells

“…␥-Lactones are industrially important flavor compounds that are widely distributed in foods, fruits, and beverages and are used in many fruity aromatic foods and cosmetics (1,2). ␥-Dodecalactone is a flavor compound that exists in apricot, peach, strawberry (3), pineapple (4), mango (5), plum (6), acerola (7), and milk (8).…”

Production of flavor compounds from olive mill waste by Rhizopus oryzae and Candida tropicalis

“…ricinoleic acid) by yeast and mold. It was also known that several fungi produced most of the terpene by the Mevalonate pathway as found in higher plant and biotransformation reactions 45, 46, 47, 48, 49. Therefore, it was concluded that 2-pentanone, d -limonene and 2-phenylethanol from OMW were produced by R. oryzae and C. tropicalis through aforementioned reactions.…”