One-pot process for the biotransformation of vegetable oils into natural deca- and dodecalactones.

Deca- and dodecalactones are highly desired natural compounds that are essential for creating flavor formulations with fruity, peachy, creamy, and floral notes. Although natural ingredients are preferred by consumers, these lactones cannot be extracted from natural sources. Therefore, the biotechnological processes that produce these compounds in their natural form are crucial for the flavor industry. Here, we report a study on the biotransformation of vegetable oils into natural deca- and dodecalactones. The proposed process is performed one-pot, through the sequential use of three different biotransformation steps, namely the lipase-mediated hydrolysis of the triglycerides, the use of probiotic bacteria for the hydration of the unsaturated fatty acids and the transformation of the obtained hydroxy-fatty acids into lactones derivatives employing Yarrowia lipolytica. By using a specific vegetable oil in combination with a selected bacterial strain, it is possible to obtain a preferred lactone derivative such as γ-dodecalactone, dairy lactone, tuberose lactone, or δ-decalactone in a concentration ranging from 0.9 to 1.5 g/L. Overall, our method is suitable for the industrial production of these lactones as it is easily scalable, it can be performed in only one bioreactor and it makes use of generally recognized as safe (GRAS) microorganisms.

Actinomycetes: A Never-Ending Source of Bioactive Compounds-An Overview on Antibiotics Production.

The discovery of penicillin by Sir Alexander Fleming in 1928 provided us with access to a new class of compounds useful at fighting bacterial infections: antibiotics. Ever since, a number of studies were carried out to find new molecules with the same activity. Microorganisms belonging to Actinobacteria phylum, the Actinomycetes, were the most important sources of antibiotics. Bioactive compounds isolated from this order were also an important inspiration reservoir for pharmaceutical chemists who realized the synthesis of new molecules with antibiotic activity. According to the World Health Organization (WHO), antibiotic resistance is currently one of the biggest threats to global health, food security, and development. The world urgently needs to adopt measures to reduce this risk by finding new antibiotics and changing the way they are used. In this review, we describe the primary role of Actinomycetes in the history of antibiotics. Antibiotics produced by these microorganisms, their bioactivities, and how their chemical structures have inspired generations of scientists working in the synthesis of new drugs are described thoroughly.

Bacterial Biotransformation of Oleic Acid: New Findings on the Formation of γ-Dodecalactone and 10-Ketostearic Acid in the Culture of Micrococcus luteus.

Microbial conversion of oleic acid (1) to form value-added industrial products has gained increasing scientific and economic interest. So far, the production of natural lactones with flavor and fragrance properties from fatty acids by non-genetically modified organisms (non-GMO) involves whole cells of bacteria catalyzing the hydration of unsaturated fatty acids as well as yeast strains responsible for further ß-oxidation processes. Development of a non-GMO process, involving a sole strain possessing both enzymatic activities, significantly lowers the costs of the process and constitutes a better method from the customers' point of view regarding biosafety issues. Twenty bacteria from the genus of Bacillus, Comamonas, Dietzia, Gordonia, Micrococcus, Pseudomonas, Rhodococcus and Streptomyces were screened for oxidative functionalization of oleic acid (1). Micrococcus luteus PCM525 was selected as the sole strain catalyzing the one-pot transformation of oleic acid (1) into natural valuable peach and strawberry-flavored γ-dodecalactone (6) used in the food, beverage, cosmetics and pharmaceutical industries. Based on the identified products formed during the process of biotransformation, we clearly established a pathway showing that oleic acid (1) is hydrated to 10-hydroxystearic acid (2), then oxidized to 10-ketostearic acid (3), giving 4-ketolauric acid (4) after three cycles of ß-oxidation, which is subsequently reduced and cyclized to γ-dodecalactone (6) (Scheme 1). Moreover, three other strains (Rhodococcus erythropolis DSM44534, Rhodococcus ruber PCM2166, Dietzia sp. DSM44016), with high concomitant activities of oleate hydratase and alcohol dehydrogenase, were identified as efficient producers of 10-ketostearic acid (3), which can be used in lubricant and detergent formulations. Considering the prevalence of γ-dodecalactone (6) and 10-ketostearic acid (3) applications and the economic benefits of sustainable management, microbial bioconversion of oleic acid (1) is an undeniably attractive approach.

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane.

In this work, we describe a study on the biotransformation of seven natural occurring apocarotenoids by means of eleven selected fungal species. The substrates, namely ionone (α-, ß- and γ-isomers), 3,4-dehydroionone, damascone (α- and ß-isomers) and theaspirane are relevant flavour and fragrances components. We found that most of the investigated biotransformation reactions afforded oxidized products such as hydroxy- keto- or epoxy-derivatives. On the contrary, the reduction of the keto groups or the reduction of the double bond functional groups were observed only for few substrates, where the reduced products are however formed in minor amount. When starting apocarotenoids are isomers of the same chemical compound (e.g., ionone isomers) their biotransformation can give products very different from each other, depending both on the starting substrate and on the fungal species used. Since the majority of the starting apocarotenoids are often available in natural form and the described products are natural compounds, identified in flavours or fragrances, our biotransformation procedures can be regarded as prospective processes for the preparation of high value olfactory active compounds.

A Study on the Lipase-catalysed Acylation of 6,7-Dihydroxy-linalool.

We here describe a study of the enzyme-mediated acylation reaction of 6,7-dihydroxy-linalool stereoisomers, which are natural triols occurring in different vegetal species. We found that only few lipases are able to catalyze the acylation of the secondary hydroxy group present in these isomers and only lipase from Candida rugosa and novozyme 435 provide either (3R,6R)-6-acetoxy-7-hydroxylinalool or (3R,6S)-6-acetoxy-7-hydroxylinalool in moderate and very good isomeric purity, respectively. Even for these favorable cases the reaction proceeds very sluggishly. Our finding can give a sensible interpretation to the fact that 6-acyl-7-hydroxy-linalool derivatives do not occur in nature, whereas the corresponding glycosides, whose formation is catalyzed by glycosidase, are very common.