Several lines of evidence indicate that important fruit aroma volatiles are derived from the degradation of carotenoid pigments. One such compound, lycopene, the major pigment in the red varieties of tomato and watermelon, gives rise, to a number of aroma volatiles including geranial, a lemon-scented monoterpene aldehyde. Various tomato and watermelon varieties and transgenic and near-isogenic tomato lines that range in color from yellow through orange to pink and red differ markedly in their carotenoid profiles. These variations are accompanied by differences in the compositions of terpenoid volatiles and hence in their taste.

Not just colors : carotenoid degradation as a link between pigmentation and aroma in tomato and watermelon fruit

The terpenes are secondary metabolites of plants that are produced, in part, as a defense against microorganisms and insects in addition to their pollinator-attractive properties.1 In mammals, terpenes contribute to stabilizing cell membranes, participate in metabolic pathways, and act as regulators in some enzymatic reactions.2 Members of this class of chemicals have carbon structures which can be decomposed into isoprene (C5H8) residues and are classified, based on the number of carbons in the molecule, as monoterpenes (ten carbons), sesquiterpenes (fifteen carbons), diterpenes (twenty carbons), triterpenes (thirty carbons), and tetraterpenes or carotenes (forty carbons).3 The simpler terpenes (monoand sesquiterpenes) are the major constituents of essential oils and are widely used in the perfumery industry, while diand triterpenes are less volatile and are obtained from plant gums and resins.4 Carotenes are synthesized by bacteria, algae, fungi, and green plants and comprise more than 600 known structures.5 The most important terpenes and their oxygenated derivates (terpenoids) cited in this study may be seen in Figures 1-3. Terpenes are a good starting material for the synthesis of many fine chemicals due to their similar carbon skeleton. R-(+)-Limonene (2), for example, is the most abundant monocyclic monoterpene in nature, and it represents more than 90% of the orange peel oil; thus, it is an inexpensive precursor.6,7 The oxygenated derivatives of limonene, e.g. carveol (24), carvone (25), perillyl alcohol (26), menthol (39), and R-terpineol (29), are recognized for their pleasant fragrances,8 and some of them also present bioactivity against certain types of tumor cells, not only preventing the formation or progression of cancer but also regressing existing malignant tumors.9,10 R-(6) and -pinene (7), in turn, are found in high concentrations in turpentine, a paper and pulp industry residue, and they are, therefore, also available in bulk at a low price. These bicyclic monoterpenes are used as a fragrance substance that is used to improve the odor of industrial products and are also precursors of important flavor compounds, such as terpineols, borneol (45), camphor (46), citronellol (11), geraniol (14), menthol (39), verbenol (48), and verbenone (49).6,7 The tetraterpene -carotene (62), an orange pigment found mainly in tropical vegetables, is a precursor of norisoprenoid ionones, molecules responsible for desirable fruity and floral flavors.7,11 Volatile carotenoid breakdown products have been long known as important flavor compounds.12

Bio-oxidation of terpenes: an approach for the flavor industry.

Carotenoids are important precursors of a variety of compounds: the C(20)-retinoids, the C(15)-phytohormones, and the C(9)- to C(13)-aromas. Among the last type, C(13)-carotenoid-derived compounds (norterpenoids/norisoprenoids) such as ionones and damascones, constitute an essential aroma note in tea, grapes, roses, tobacco, and wine. Extraction of carotenoid-derived aroma compounds from plant sources is not economically realistic or considerably expensive. The biotechnological production of aroma compounds represents a feasible alternative and offers the production of enantiomerically pure molecules which can be labeled as "natural." To date, research in the production of ionones or the C(10)-compound, safranal, has mainly been focused on plant dioxygenases that cleave carotenoids in the positions between carbons 9 and 10 (9'-10') or 7 and 8 (7'-8'), respectively. Although relatively little is known about the microbial conversion of carotenoids into compounds with aroma due to the well known advantages of manipulating microorganisms, the aim of this work is to review the current state of the research in microbial production of norisoprenoids and other aroma compounds derived from carotenoid cleavage.

Microbial Production of C13-Norisoprenoids and Other Aroma Compounds via Carotenoid Cleavage

Various applications of biotechnological methods for the production of volatile compounds useful to the food and pharmaceutical industries are discussed. The yields obtained from intact or genetically modified plants are compared to those achieved by microbial methods. Plant yields are too low for the products to compete commercially to those synthesized chemically. Still lower yields are obtained with in vitro-cultured plant tissues. Trangenic plants with altered methylerythritol path gave 50% more essential oil in the best case. The 100-fold increases in shikimate-derived volatiles, obtained with overexpressed alcohol dehydrogenase and five-fold more C6 volatle aldehydes and 2-phenylethanol, were produced with overexpressed lipoxygenase and 2-phenylethanol dehydrogenase, respectively. However, the most spectacular yields were observed with biotransformations catalysed by microorganisms. Kluyveromyces marxianus, produces over 26 g/l 2-phenylethanol from phenyalanine, whereas Candida sorbophila, Mucor circillenoides or Yarrowia lipolytica can produce 5–40 g/l γ-decalactone from ricinoleic acid. Vanillin production from ferulic acid is in the range 12–60 g/l with Amycolatopsis and Streptomyces species. Vanillin can be produced at 5 g/l by Escherichia coli and amorphadiene yields of 37 g/l have been observed with Saccharomyces cerevisiae, both with the genetically overexpressed methyl–erythritol path. Genetically engineered β-oxidation genes result in yields of 10 g/l γ-decalactone by Yarrowia lipolytica and up to 80 g/l dicaboxylic acids by various yeasts. These results far exceed the theoretical limit of about 1 g/l required for consideration of a procedure as a commercially interesting process, alternative to chemical sythesis. Copyright © 2010 John Wiley & Sons, Ltd.

Biotechnology for the production of essential oils, flavours and volatile isolates. A review.†‡

The main objective of this work was to investigate the application of supercritical carbon dioxide as anti-solvent for the encapsulation of β-carotene in poly(hydroxybutirate-co-hydroxyvalerate) (PHBV) with dichloromethane as organic solvent using the Solution Enhanced Dispersion by Supercritical fluids (SEDS) technique. For the precipitation experiments with pure compounds the parameters investigated were the concentration of β-carotene (4 and 8 mg mL−1) and PHBV (30 mg mL−1) in the organic solution, pressure (from 80 to 200 bar), solution flow rate fixed at 1 mL min−1, anti-solvent flow rate at 40 mL min−1 and constant temperature of 313 K. Pure β-carotene precipitation indicates that an increase in pressure led in most cases to particles with larger sizes, while the opposite trend was verified for pure PHBV precipitation. The morphology of precipitated PHBV particles was spherical and was not influenced by increasing pressure. The morphology of β-carotene microparticles changed from plate-like to leaf-like particles when raising operational pressure, but was not influenced by its concentration in the organic solution as verified by micrographs of scanning electronic microscopy (SEM). For the co-precipitation experiments it was evaluated the effect of β-carotene concentration (2–30 mg mL−1) in the organic solution, at fixed parameters: PHBV concentration (30 mg mL−1) in organic solution, temperature at 313 K, pressure at 80 bar, solution flow rate at 1 mL min−1 and anti-solvent flow rate at 40 mL min−1. The encapsulation data showed that increasing the concentration of β-carotene, keeping fixed the PHBV content, results in higher percentage of solute encapsulated, increasing the encapsulation efficiency.

Precipitation and encapsulation of β-carotene in PHBV using carbon dioxide as anti-solvent

A residual mud sample from the marigold flower dehydration process was screened and 19 putative colonies were isolated for their ability to degrade lutein in a chemically defined medium supplemented with marigold flower flour as a carbon source. Among the colonies isolated, two generated volatile compounds in fermentation and one was chosen for further study for its ability to produce a strong tobacco smell. This colony contained two microorganisms, identified as Geotrichum sp. and Bacillus sp. The aroma production requires the presence of both microorganisms and lutein. Using gas chromatography coupled to mass spectrometry (GC/MS), four compounds were identified: 7,8-dihydro- β-ionol, β-ionone, 7,8-dihydro-β-ionone, and 3-hydroxy-β-ionone, in proportions of 84.2%, 9.4%, 3.5%, and 2.9%, respectively.

Bioconversion of lutein to products with aroma.

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Bioconversion of lutein to products with aroma.