Limonene: a versatile chemical of the bioeconomy

Ciriminna, Rosaria; Lomelí-Rodríguez, Mónica; Carà, Piera Demma; López-Sánchez, José Antonio; Pagliaro, Mario

doi:10.1039/c4cc06147k

Cited by 406 publications

(327 citation statements)

References 39 publications

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“…Its antimicrobial properties make it a popular component of disinfectants and food preservatives and an environmentally friendly solvent used at the industrial scale (1)(2)(3)(4). More recently, limonene or its hydrogenated forms have been identified to be potential jet fuel components (5-7).…”

mentioning

confidence: 99%

Acute Limonene Toxicity in Escherichia coli Is Caused by Limonene Hydroperoxide and Alleviated by a Point Mutation in Alkyl Hydroperoxidase AhpC

Chubukov

Mingardon

Schackwitz

et al. 2015

Appl Environ Microbiol

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f Limonene, a major component of citrus peel oil, has a number of applications related to microbiology. The antimicrobial properties of limonene make it a popular disinfectant and food preservative, while its potential as a biofuel component has made it the target of renewable production efforts through microbial metabolic engineering. For both applications, an understanding of microbial sensitivity or tolerance to limonene is crucial, but the mechanism of limonene toxicity remains enigmatic. In this study, we characterized a limonene-tolerant strain of Escherichia coli and found a mutation in ahpC, encoding alkyl hydroperoxidase, which alleviated limonene toxicity. We show that the acute toxicity previously attributed to limonene is largely due to the common oxidation product limonene hydroperoxide, which forms spontaneously in aerobic environments. The mutant AhpC protein with an L-to-Q change at position 177 (AhpC L177Q ) was able to alleviate this toxicity by reducing the hydroperoxide to a more benign compound. We show that the degree of limonene toxicity is a function of its oxidation level and that nonoxidized limonene has relatively little toxicity to wild-type E. coli cells. Our results have implications for both the renewable production of limonene and the applications of limonene as an antimicrobial. L imonene, the major component of citrus peel oil, has a variety of industrial and microbiological applications. Its antimicrobial properties make it a popular component of disinfectants and food preservatives and an environmentally friendly solvent used at the industrial scale (1-4). More recently, limonene or its hydrogenated forms have been identified to be potential jet fuel components (5-7). As such, the anticipation of a greater global demand for limonene has provided significant motivation for the renewable production of this compound from plant biomass through a microbial process (8-10), and recent efforts to optimize production have resulted in titers of over 400 mg/liter at the bench scale (11). In this context, the toxicity of limonene to the microbial host presents a major challenge, as the accumulation of toxic products limits growth and metabolic activity.Curiously, the toxicity of limonene has been reported to be significantly higher than that of other monoterpenes or solvents with similar hydrophobicities (12, 13), suggesting that this acute toxicity is due to something other than its solvent-like properties. However, molecular-level studies of limonene toxicity in microbes are limited. While several studies in Escherichia coli have noted an impact of limonene on lipid composition (14) and suggested a role for reactive oxygen species (ROS) (15), no specific hypothesis for how limonene causes these cellular perturbations has been proposed.In this work, we investigated the basis of limonene toxicity in the model Gram-negative bacterium E. coli. We identified a mutant with significantly enhanced tolerance to limonene and show that the majority of the toxicity in wild-type (WT) cells is due no...

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confidence: 99%

Acute Limonene Toxicity in Escherichia coli Is Caused by Limonene Hydroperoxide and Alleviated by a Point Mutation in Alkyl Hydroperoxidase AhpC

Chubukov

Mingardon

Schackwitz

et al. 2015

Appl Environ Microbiol

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“…The limonene (boiling point = 178 °C) removal occurred at 120 °C to 160 °C, which was followed by a rapid decompression (Ciriminna et al 2014). Leaching of the limonene from the CW by a solvent, such as hexane, under mild conditions was first proposed by Wikandari et al (2015) as a pretreatment method for improving biogas production.…”

Section: Enzymatic Hydrolysis Of the Treated Cwmentioning

confidence: 99%

Process Optimization for Citrus Waste Biorefinery via Simultaneous Pectin Extraction and Pretreatment

Satari¹,

Palhed²,

Karimi³

et al. 2017

BioResources

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In a novel valorization approach for simultaneous pectin extraction and pretreatment (SPEP) of citrus waste (CW) by dilute nitric acid and ethanol, almost all of the CW was converted to bio-derived chemicals in a singlestep process at a low/moderate temperature. The SPEP was performed at different temperatures (70 °C and 80 °C), pH (1.8, 3.0, and 4.3), and extraction times (2 h and 3 h) with a full factorial design. The maximum pectin yield of 45.5% was obtained at pH 1.8, 80 °C, and 2 h. The pectin yields at pH 1.8 were much higher than at pH 4.3 and 3. Also, the degree of methyl-esterification at pH 1.8 was higher than 50%, whereas at the higher pH, low methoxyl pectins were extracted. The treated CW obtained after the SPEP, free from limonene, was subjected to separate cellulolytic enzymatic hydrolysis and ethanolic fermentation. The glucose yields in the enzymatic hydrolysates were higher for the CW treated at pH 1.8. The fermentation of the enzymatic hydrolysates by Mucor indicus resulted in fungal biomass yields in the range of 355 to 687 mg per g of consumed sugars. The optimum conditions for obtaining the maximum SPEP yield (glucose + pectin (g) / raw material (g))*100) were pH 1.8, 80 °C, and 2 h, which resulted in a yield of 58.7% (g/g CW).

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“…Limonene is widely used in food and cosmetic industries, and also in production of refrigerant fluids, paints, agrochemicals and cleaning agents. [8][9][10][11][12][13] R-(+)-limonene is the major component (about 97%) of the orange oil obtained from orange and lemon peels (biomass) which are the waste product of the citrus fruit industry. The main methods of obtaining orange oil from the orange peels are: cold pressing and distillation.…”

Section: Introductionmentioning

confidence: 99%

Fragrant starch-based films with limonene

Antosik¹,

Wilpiszewska²,

Wróblewska³

et al. 2017

10.5267/j.ccl

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Novel fragrant starch-based films with limonene were successfully prepared. Biodegradable materials of natural origin were used and the process was relatively simple and inexpensive. The effect of limonene on physicochemical properties of starch-based films (moisture absorption, solubility in water, wettability, mechanical properties) were compared to glycerol plasticized system. Taking into consideration that the obtained materials could also exhibit bactericidal and fungicidal properties, the studies with Escherichia coli, Candida albicans and Aspergillus niger were performed. Such a material could potentially find application in food packaging (e.g. masking unpleasant odors, hydrophilic starch film would prevent food drying), or in agriculture (e.g. for seed encapsulated tapes).

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Limonene: a versatile chemical of the bioeconomy

Cited by 406 publications

References 39 publications

Acute Limonene Toxicity in Escherichia coli Is Caused by Limonene Hydroperoxide and Alleviated by a Point Mutation in Alkyl Hydroperoxidase AhpC

Acute Limonene Toxicity in Escherichia coli Is Caused by Limonene Hydroperoxide and Alleviated by a Point Mutation in Alkyl Hydroperoxidase AhpC

Process Optimization for Citrus Waste Biorefinery via Simultaneous Pectin Extraction and Pretreatment

Fragrant starch-based films with limonene

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