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Variation of terpenes in milk and cultured cream from Norwegian alpine rangeland-fed and in-door fed cows
Abstract
The terpene content of milk and cream made from milk obtained from cows fed indoors, and by early or late grazing, in alpine rangeland farms in Norway, were analysed for three consecutive years. The main terpenes identified and semi-quantified were the monoterpenes β-pinene, α-pinene, α-thujene, camphene, sabinene, δ-3-carene, d-limonene, γ-terpinene, camphor, β-citronellene, and the sesquiterpene β-caryophyllene. The average total terpene content increased five times during the alpine rangeland feeding period. The terpenes α-thujene, sabinene, γ-terpinene and β-citronellene were only detected in milk and cultured cream from the alpine rangeland feeding period and not in samples from the indoors feeding period. These four terpenes could be used, as indicators, to show that milk and cultured cream originate from the alpine rangeland feeding period. The terpenes did not influence the sensorial quality of the milk or the cultured cream.
... From all the identified families of compounds terpenes have been proposed as indicators of the diet mainly when animals were grazing different pastures and their content may by five times higher when in pasture as compared to in-door feeding [57]. In fact, they have been proposed as indicators of mountain pasture milk [58], some others reported that even in semi-pasture combined with in-door feeding terpenes do not allow the differentiation with in-door feeding [59]. ...
... Terpenes may suffer further transformations, they may be directly transferred from the diet (on inhaled) to milk or may be further modified in the rumen (biohydrogenated and isomerized) [62]. Even during milk fermentation terpenes may undergo further modifications [57]. ...
Large amount of vegetal by-products are generated during production and processing steps. Introducing silage from vegetable by-products into dairy goat feed would be of great interest from the point of view of reducing costs and supporting the circular economy. The aim of this research was to study the effect of 40% inclusion of silage broccoli by-products and artichoke plant by-products in the diet of Murciano-Granadina goats throughout the lactation to establish milk suitability for fermented milks production. The novelty of this study is the use of milk from goats fed for a long term with a high inclusion of silages from artichoke plant and broccoli by-products, being the first one on broccoli inclusion. Two starter cultures thermophilic (YO-MIXTM300), and, mesophilic (MA400) were used and fermented milks were analyzed at two storage times after fermentation. Fermentation enhances antioxidant properties of fermented milks from all diets (p < 0.05), especially when mesophilic starter cultures are used. The main findings are that long term inclusion of 40% silage from broccoli and artichoke plant by-products in balanced diets of dairy goats yields milk suitable for fermentation by yogurt and cheese cultures, the inclusion of broccoli silage enhances antioxidant properties (p < 0.05), and, the inclusion of plant artichoke enhances fatty acids health indexes (p < 0.05).
... The constant "arms race" between plants and herbivores has resulted in an extraordinary diversity of phytochemicals produced by plants (Burkepile and Parker, 2017). In turn, many of these plant phytochemicals are concentrated in the meat and milk of livestock grazing these plants (Børge et al., 2016;Delgadillo-Puga et al., 2019;Prache et al., 2020); their presence may act synergistically to enhance human health (Barabási et al., 2020). Importantly, the presence of these phytochemicals in pasture-raised animal products remains largely underappreciated in discussions of nutritional differences between grain-fed and pasture-raised (grass-fed) meat and dairy, which have predominantly been centered around the ω-3 fatty acids and CLA (Provenza et al., 2019). ...
... Similarly, Agabriel et al. (2007) found that terpenes-such as α-copaene (anti-oxidant), β-bourbonene (anti-tumor, apoptosis inducer), β-pinene (anti-inflammatory, anti-oxidant, anti-tumor), β-Elemene (anti-inflammatory, antitumor), and sabinene (anti-inflammatory, anti-oxidant)-were higher in milk from pasture-raised animals with access to more forage diversity compared to animals fed grain-based diets. Likewise, Børge et al. (2016) found that δ-3 Carene, α + βpinene, α-thujene, ß-citronellene, and sabinene concentrations (anti-inflammatory, anti-bacterial, anti-oxidant, and/or anticarcinogenic) were collectively 5-fold higher in cream produced from animals raised on diversified pasture compared to cream from animals fed concentrates. ...
While commission reports and nutritional guidelines raise concerns about the effects of consuming red meat on human health, the impacts of how livestock are raised and finished on consumer health are generally ignored. Meat and milk, irrespective of rearing practices, provide many essential nutrients including bioavailable protein, zinc, iron, selenium, calcium, and/or B12. Emerging data indicate that when livestock are eating a diverse array of plants on pasture, additional health-promoting phytonutrients—terpenoids, phenols, carotenoids, and anti-oxidants—become concentrated in their meat and milk. Several phytochemicals found in grass-fed meat and milk are in quantities comparable to those found in plant foods known to have anti-inflammatory, anti-carcinogenic, and cardioprotective effects. As meat and milk are often not considered as sources of phytochemicals, their presence has remained largely underappreciated in discussions of nutritional differences between feedlot-fed (grain-fed) and pasture-finished (grass-fed) meat and dairy, which have predominantly centered around the ω-3 fatty acids and conjugated linoleic acid. Grazing livestock on plant-species diverse pastures concentrates a wider variety and higher amounts of phytochemicals in meat and milk compared to grazing monoculture pastures, while phytochemicals are further reduced or absent in meat and milk of grain-fed animals. The co-evolution of plants and herbivores has led to plants/crops being more productive when grazed in accordance with agroecological principles. The increased phytochemical richness of productive vegetation has potential to improve the health of animals and upscale these nutrients to also benefit human health. Several studies have found increased anti-oxidant activity in meat and milk of grass-fed vs. grain-fed animals. Only a handful of studies have investigated the effects of grass-fed meat and dairy consumption on human health and show potential for anti-inflammatory effects and improved lipoprotein profiles. However, current knowledge does not allow for direct linking of livestock production practices to human health. Future research should systematically assess linkages between the phytochemical richness of livestock diets, the nutrient density of animal foods, and subsequent effects on human metabolic health. This is important given current societal concerns about red meat consumption and human health. Addressing this research gap will require greater collaborative efforts from the fields of agriculture and medicine.
... Interestingly, α-pinene can also be found at high concentrations in milk, which is reported in certain populations of cows fed on alpine rangeland diets. Therefore, it is not recommended for cows to eat plants that contain high concentrations of pinene such as juniper or pine needles, as it was found to induce abortion particularly in the last trimester [59][60][61] . Murine studies have shown that α-pinene inhalation exposure to 400 ppm led to a decreased body mass, liver and kidney defects, especially in female rats 62 . ...
... In order to avoid this danger, and the efforts made to reduce the addiction to nicotine have led to the development of ENNDS, which simulates the physical action of conventional cigarettes, but without using any of the nicotine 64,65 . Their main selling point is simply the overwhelming variety of flavours and the overall social experience of vaping, partly dependent on the types of solvent (or bases) in which these 59,110,118,133,134 0.10-97~1-1.7 3-12 640-4800 *Present in cinnamon oil;not identified. If more than one value were identified (from different products of the same category), the concentration values are given as a range. ...
Food flavour ingredients are required by law to obtain prior approval from regulatory bodies, such as the U.S. Food and Drug Administration (FDA) or the European Food Safety Authority (EFSA) in terms of toxicological data and intended use levels. However, there are no regulations for labelling the type and concentration of flavour additives on the product, primarily due to their low concentration in food and generally recognised as safe (GRAS) status determined by the flavour and extract manufacturers' association (FEMA). Their status for use in e-cigarettes and other vaping products challenges these fundamental assumptions, because their concentration can be over ten-thousand times higher than in food, and the method of administration is through inhalation, which is currently not evaluated by the FEMA expert panel. This work provides a review of some common flavour ingredients used in food and vaping products, their product concentrations, inhalation toxicity and aroma interactions reported with different biological substrates. We have identified several studies, which suggest that the high concentrations of flavour through inhalation may pose a serious health threat, especially in terms of their cytotoxicity. As a result of the wide range of possible protein-aroma interactions reported in our diet and metabolism, including links to several non-communicable diseases, we suggest that it is instrumental to update current flavour- labelling regulations, and support new strategies of understanding the effects of flavour uptake on the digestive and respiratory systems, in order to prevent the onset of future non-communicable diseases.
... The milk VOC are derived from animal metabolism and interaction with the surrounding environment, namely diet and rearing conditions (Mariaca et al., 1997;Viallon et al., 1999;Bergamaschi & Bittante, 2018). There is high evidence that the VOC profile of milk from grazing cattle is different from that of cows fed indoor (Villeneuve et al., 2013;Borge et al., 2016). The most part of the information in the literature regards the comparison between intensive and non-intensive farming systems in mountain areas. ...
... In such environment, milk from grazing cows is characterised by high presence of terpenes: these isoprenoid molecules are rapidly transferred from feed to milk, in particular when cattle graze on pastures rich in spontaneous dicotyledonous plant (Fedele et al., 2005;De Noni & Battelli, 2008;Chion et al., 2010). Despite of their importance as molecular markers of grazing ruminants, the contribution of terpenes to the aroma of milk and cheese is highly questioned due to the high odour threshold and the low concentration at which they are present (Coulon et al., 2004;Borge et al., 2016). General consensus exists that the cheese aroma mostly originates from a series of chemical and biochemical events connected to the processing technology and microbiota activity during ripening (Mc Sweeney & Sousa, 2000). ...
The volatile organic compounds (VOC) and sensory characteristics of milk and mozzarella from farms with different rearing systems were compared. Milk samples were taken from 9 intensive (INT) and 13 semi‐extensive farms (EXT) in the grazing period. VOC were analysed by SPME‐GC‐MS, and sensory evaluation was carried out by paired comparison. The volatile profiles of milks were significantly different: acetone and isopropyl alcohol characterised INT milk, pentanoic and decanoic acids, hexanal, ethylacetate, toluene, dimethyl sulphide characterised milk from EXT farms. Also mozzarella was discriminated by VOC, but only a few compounds derived from milk. Based on sensory evaluation, milk from the two sources can be distinguished by odour and colour, mozzarella only by colour. It was hypothesised that heating during the stretching phase caused volatilisation of many milk volatile compounds and formation new aroma active molecules that overcame the ‘primary odours’ of milk.
... These differences are likely due to the source of milk. Minor constituents of milk can vary depending on the diet of the cattle and geographic location (Turbes et al., 2016;Borge et al., 2016). Terpenes and terpenoids are organic compounds found widely in plants, and cattle feed is a significant source of these compounds in milk and milk products (Lejonklev et al., 2013). ...
... Terpenes and terpenoids are organic compounds found widely in plants, and cattle feed is a significant source of these compounds in milk and milk products (Lejonklev et al., 2013). Microbial activity is also known to alter terpene and terpenoid content in many food products, and fermentation may also alter the content in the whey (Borge et al., 2016). d-Limonene and geraniol can imbue distillates with citrus, floral, and fruit aromas, whereas farnesol and α-farnesene may negatively affect the distillates' organoleptic qualities due to their oil and boiled vegetable aromas (Flavor and Extract Manufacturers Association, 2017). ...
Lactose within whey can be fermented and distilled to produce a potable distilled spirit. The aim of this study was to determine if acid and sweet whey types can be fermented and distilled using similar processes and to investigate differences in volatile aroma compounds for the 2 distillates. Fermentation and distillation of the 2 whey types progressed in a similar manner, using Kluyveromyces marxianus for the initial fermentation and a glass still fitted with a Vigreux column for the subsequent distillation. Ethanol content of the wash (fermented whey) varied considerably following each fermentation and ranged from 1.2 and 2.0% (wt/wt) with no clear trend between acid and sweet whey samples. Volatile aroma compounds were extracted using headspace solid-phase microextraction and identified via gas chromatography-mass spectrometry. Acid and sweet whey distillates contained unique volatile aromatic compounds, and significant differences in compound peak areas were observed. These differences may have an effect upon the organoleptic qualities of spirits produced from whey; therefore, whey source may be an important factor when fermenting and distilling whey.
... These differences are likely due to the source of milk. Minor constituents of milk can vary depending on the diet of the cattle and geographic location 76,77 . Terpenes and terpenoids, are organic compounds found widely in plants and the cattle feed is a significant source of these compounds in milk and milk products 78 . ...
... The presence of most of the identified components has already been reported in the case of milk or cheeses (Dumont and Adda, 1978;Guichard et al. 1987;Buchin et al. 1999;Viallon et al. 1999Viallon et al. , 2000Fernandez et al. 2003). Borge et al. (2016) compared the terpene content of creams made from the milk of grazed and barn-fed cows. Samples from barn-fed and grazed cows also showed α-pinene and limonene; however, the amount of α-pinene was significantly higher in the samples of grazed individuals, while the amount of limonene was significantly higher in the samples of individuals fed in the barn. ...
This study presented the development of such a HS-SPME-GC-MS technique, with the use of which, directly from the raw milk sample matrix, both qualitatively and quantitatively; the volatile terpenoids (α-pinene, sabinene, β-pinene, p-cymene, limonene, linalool, α-thujene, camphor, menthol, methyl chavicol, caryophyllene E, α-humulene) can be determined, derived from herbs eaten by the dairy animals by different feeding methods. Repeatability was less than 10% in the case of milk fat samples. The estimated limits of quantitation were between 2 and 16 ng/g. The lowest values were 2 ng/g for p-cymene and methyl chavicol; the highest value was 16 ng/g for caryophyllene. In the case of goat milk, the repeatability was better than 8% except for α-thujene. The estimated limits of quantitation were between 1 and 8 ng/g. The lowest values were 1 ng/g for β-pinene, p-cymene and limonene, and the highest value was 8 ng/g for linalool. In milk fat, the highest concentration was identified in caryophyllene E (470 ng/g) and α-humulene (430 ng/g), while the lowest concentration was in p-cymene (2 ng/g) and camphor (2 ng/g). In goat milk, limonene was present in all samples, but its amount varied depending on the type of consumed herb. Methyl chavicol and caryophyllene E were detected in goat's milk only in one case. The former was detected in sage milk at 2.09 ng/g and the latter in tarragon milk at 2.28 ng/g. We have also successfully demonstrated that the feed consumed by dairy animals also affects the quality of dairy products.
... valerian (Valeriana officinalis), wild sage (Salvia verbenaca), rosemary (Rosmarinus officinalis) (0.1-8.3%) and basil (Ocimum basilicum), as an essential oil [88]. Depending on the forage quality, BCP can also accumulate in cow's milk in higher or lower concentrations [89]. The safety of the molecule has been approved by the Food and Drug Administration and the European Food Safety Authority, who have approved its use as an additive in cosmetics and foodstuff production [90]. ...
Neurodegenerative disorders are a widespread cause of morbidity and mortality worldwide, characterized by neuroinflammation, oxidative stress and neuronal depletion. The broad-spectrum neuroprotective activity of the Mediterranean diet is widely documented, but it is not yet known whether its nutritional and caloric balance can induce a modulation of the endocannabinoid system. In recent decades, many studies have shown how endocannabinoid tone enhancement may be a promising new therapeutic strategy to counteract the main hallmarks of neurodegeneration. From a phylogenetic point of view, the human co-evolution between the endocannabinoid system and dietary habits could play a key role in the pro-homeostatic activity of the Mediterranean lifestyle: this adaptive balance among our ancestors has been compromised by the modern Western diet, resulting in a “clinical endocannabinoid deficiency syndrome”. This review aims to evaluate the evidence accumulated in the literature on the neuroprotective, immunomodulatory and antioxidant properties of the Mediterranean diet related to the modulation of the endocannabinoid system, suggesting new prospects for research and clinical interventions against neurodegenerative diseases in light of a nutraceutical paradigm.
... effect on terpene abundance but not on the diversity. Terpenes, lipophilic volatile compounds (Borge et al., 2016), were slightly higher in GS cheese with the high fat content. ...
The objective of this study was to determine volatile compounds, color parameters and sensory characteristics in raw sheep milk cheeses ripened up to 270 days using different packaging materials such as goat’s skin bag or plastic barrel. Volatile compounds extracted by solid-phase microextraction were separated, identified and quantified using a gas chromatography (GC)-mass spectrometry detector (MS). Butanoic acid, hexanoic acid, octanoic acid, ethanol, ethyl acetate, ethyl butanoate, ethyl hexanoate, 2-butanol, 2-butanone and 2-heptanone were the predominant compounds in the volatile fraction of the cheeses. Among these, ethanol was the most abundant at the first 180 days of cheese ripening but there were 2-butanol and 2-butanone for cheese in plastic barrel (PB) and 2-heptanone for cheese in goat’s skin bag (GS) at the 270 days. To best acknowledge, m-cimene, alpha-cubebene, trans-caryophylene, delta-cadinene and 16-oxasalutaridine were identified for the first time in sheep milk and its cheese. Discriminant analysis based on volatile compounds classified the cheeses according to their ripening times and also packaging materials. At the end of the ripening the differentiation between GS and PB cheeses was more evident. The results showed that GS cheese was more preferred by panelists. Cheeses ripened for more 180 days, in particular PB cheese, were much less acceptable to panelists. Therefore, in terms of optimum overall acceptability, 90 and 180 days ripening periods could be advised for the producers for PB and GS cheeses, respectively.
... The composition of the volatile aroma compounds within milk and other dairy products can vary depending upon the source of the milk [62]. The milk producer's diet and geographic location can be attributed to the presence volatile compounds such as terpenes and terpenoids [63,64]. The cheese production process can also influence volatile compound composition of whey, particularly the application of heat and exposure to microorganisms. ...
... accumulates with a BCP rich diet (Borge et al., 2016). Attempts to establish structure-activity relationships with BCP at the CB 2 receptor have failed (Chicca et al., 2014) as this simple bicyclic hydrocarbon scaffold offers limited possibilities. ...
The endocannabinoid system (ECS) is a major lipid signalling network that plays important pro-homeostatic (allostatic) roles not only in the nervous system but also in peripheral organs. There is increasing evidence that there is a dietary component in the modulation of the ECS. Cannabinoid receptors in hominids co-evolved with diet, and the ECS constitutes a feedback loop for food selection and energy metabolism. Here, it is postulated that the mismatch of ancient lipid genes of hunter-gatherers and pastoralists with the high-carbohydrate diet introduced by agriculture could be compensated for via dietary modulation of the ECS. In addition to the fatty acid precursors of endocannabinoids, the potential role of dietary cannabimimetic phytochemicals in agriculturist nutrition is discussed. Dietary secondary metabolites from vegetables and spices able to enhance the activity of cannabinoid-type 2 (CB2 ) receptors may provide adaptive metabolic advantages and counteract inflammation. In contrast, chronic CB1 receptor activation in hedonic obese individuals may enhance pathophysiological processes related to hyperlipidaemia, diabetes, hepatorenal inflammation and cardiometabolic risk. Food able to modulate the CB1 /CB2 receptor activation ratio may thus play a role in the nutrition transition of Western high-calorie diets. In this review, the interplay between diet and the ECS is highlighted from an evolutionary perspective. The emerging potential of cannabimimetic food as a nutraceutical strategy is critically discussed.
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This article is part of a themed section on Principles of Pharmacological Research of Nutraceuticals. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.v174.11/issuetoc.
... Also, high variability in the terpenoid composition of grazing milk and cheese occurs mostly due to pasture plant diversity, geographical grassland altitude and location, seasonal feeding variations linked to lactation stage and pasture availability, and type of management systems (Cornu et al., 2001;Fernández et al., 2003;Tornambé et al., 2006;Agabriel et al., 2007;De Noni and Batelli, 2008;Revello Chion et al., 2010;Abilleira et al., 2011). Despite the variability, some specific terpenoids such as β-caryophyllene, α-copaene, α-pinene, and β-pinene are often found in milks and cheeses from animals grazing in humid pastures of grasslands in Europe (Tornambé et al., 2006;Revello Chion et al., 2010;Borge et al., 2016;Valdivielso et al., 2016b), and even β-caryophyllene has been proposed as a potential pasture-diet marker because of its ubiquity in fresh pasture plants (Mariaca et al., 1997;Favaro et al., 2005;Abilleira et al., 2011;Valdivielso et al., 2016b). On the other hand, terpenoids can contribute floral and vegetal odor to the flavor of cheese made with milk from grazing animals (Bugaud et al., 2001;Carpino et al., 2004). ...
Changes in the terpenoid content of milk and cheese from commercial sheep flocks monitored throughout lactation in the Cantabrian area of northern Spain were investigated. The flocks followed the same seasonal feeding strategy during lactation: indoor feeding in winter (early lactation) based on concentrate and forage; part-time grazing in the valley in early spring (mid lactation); and from mid spring on (late lactation), flocks were managed under extensive mountain grazing. In the present study design, seasonal feeding and lactation stage were intrinsically linked and could not be considered in isolation, and a holistic approach was necessary to consider the whole production management of the commercial flocks studied. Furthermore, the study focused on the identification of sesquiterpenoid ratios to differentiate milks and cheeses produced under extensive mountain grazing from those produced under other seasonal feeding regimens. Total abundance of mono- and sesquiterpenoids and that of individual compounds such as α-pinene, β-caryophyllene, α-humulene, α-amorphene, and γ-cadinene significantly increased in milk and cheese from indoor feeding to mountain extensive grazing. Sesquiterpenoid ratios such as γ-cadinene/α-muurolene, γ-cadinene/δ-cadinene, β-caryophyllene/α-muurolene, and (β-caryophyllene + γ-cadinene)/α-muurolene were used to differentiate mountain milks and cheeses from those from indoor feeding and part-time grazing in the valley. Multivariate discriminant analysis applied to individual terpenoids and sesquiterpenoid ratios showed milk and cheese samples classified into 2 groups: samples from indoor feeding and part-time grazing in the valley were classified together, and clearly separated from mountain milks and cheeses. The results of the present study showed that the sesquiterpenoid ratios approach could help to differentiate mountain dairy products from others obtained under other specific feeding regimens in a local environment.
... The level of terpenes fluctuated with a decrease on d 1 followed by elevated levels until the end of ripening. Terpenes are lipophilic volatile compounds (Borge et al., 2016) and derive from milk fat (Viallon et al., 2000) of which the concentration also increases as a result of water loss during ripening. Several other studies showed that terpenes may also be formed by microorganisms such as yeasts and especially Kluyveromyces lactis (Martin et al., 2001) and fungal cultures (Agrawal and Joseph, 2000) in the milk and milk products and they might be changed as a result of microbial activity. ...
The formation of volatile compounds in Turkish Divle Cave cheese produced in 3 different dairy farms was determined during production and ripening, revealing 110 compounds including acids, alcohols, ketones, esters, and terpenes. The presence and concentration of these volatile compounds varied between specific phases of the production and the 120-d ripening process. Smaller differences were also detected between cheeses produced at different farms. Carboxylic acids were established as a major class at the end of ripening. The relative amounts of acids and ketones increased until d 90 of ripening, whereas alcohols increased for the first 30 d and tailed off during the remaining part of the ripening process. The level of esters increased gradually until the end of ripening. Butanoic, acetic, and valeric acids, 2-butanol, 2-butanone, 2-heptanone, ethyl butanoate, α-pinene, and toluene were the most abundant compounds, likely contributing to the characteristic aroma of this traditional cheese.
The aim of this work was to verify the suitability of terpenoids and fatty acid composition to authenticate the altitude of milk production. Milk originating from lowland (L1), mountain (M1) and alpine pasture (H1 and H2) in the Aosta Valley (Northwest Italy), during the month of June, was collected at a cheese factory. The M1, H1, and H2 milk is characterised by a high content of α-linolenic, vaccenic acid and conjugated linoleic fatty acids, compared with milk from lowland pastures. Terpenoid profiles changed with altitude of grazing. The leave-one-out cross-validation, using altitude of grazing as a grouping, and C14:0iso, anteisoC17:0, C18:1trans-11, C18:2trans-9,trans-12 and cis-ocimene as discriminant variables, gave a correct classification rates of 98% of milk samples to origin of production.
The endocannabinoid system (ECS), a conserved physiological system emerged as a novel pharmacological target for its significant role and potential therapeutic benefits ranging from neurological diseases to cancer. Among both, CB1 and CB2R types, CB2R have received attention for its pharmacological effects as antioxidant, anti-inflammatory, immunomodulatory and antiapoptotic that can be achieved without causing psychotropic adverse effects through CB1R. The ligands activate CB2R are of endogenous, synthetic and plant origin. In recent years, β-caryophyllene (BCP), a natural bicyclic sesquiterpene in cannabis as well as non-cannabis plants, has received attention due to its selective agonist property on CB2R. BCP has been well studied in a variety of pathological conditions mediating CB2R selective agonist property. The focus of the present manuscript is to represent the CB2R selective agonist mediated pharmacological mechanisms and therapeutic potential of BCP. The present narrative review summarizes insights into the CB2R-selective pharmacological properties and therapeutic potential of BCP such as cardioprotective, hepatoprotective, neuroprotective, nephroprotective, gastroprotective, chemopreventive, antioxidant, anti-inflammatory, and immunomodulator. The available evidences suggest that BCP, can be an important candidate of plant origin endowed with CB2R selective properties that may provide a pharmacological rationale for its pharmacotherapeutic application and pharmaceutical development like a drug. Additionally, given the wide availability in edible plants and dietary use, with safety, and no toxicity, BCP can be promoted as a nutraceutical and functional food for general health and well-being. Further, studies are needed to explore pharmacological and pharmaceutical opportunities for therapeutic and preventive applications of use of BCP in human diseases.
Few researchers in the phytochemical sciences regard milk as a bioactive natural product. However, milk emanates entirely from living mammals and every carbon atom in milk stems directly or indirectly from plants, fungi, and bacteria with the exception of anthropogenic contaminants. In addition to the usual constituents of milk, lactogenesis or milk synthesis drags with it a substantial number of adventitious organic compounds, healthy, and appetizing or downright harmful and repulsive, acquired through diet, breath, and skin absorption. Animals and people alike are exposed to a large number of organic pollutants, pharmaceutical drugs, substances from wood combustion for cooking and heating, and many other sources related to human activities. These nonnatural products can reach pristine remote pastures carried by long range air circulation, posing new challenges to dairy cattle husbandry. Many of these compounds are carried over to milk passing through the animal in proportion to the lipid-to-water partition coefficients and to physicochemical features well defined by their molecular structure. Several compounds uptaken in blood get across the plasma–milk barrier by way of passive diffusion or aided by specific transmembrane transporters. Milk chemistry is also a complex biochemical subject. As a most nutritious medium, milk harbors numerous bacteria, fungi, and yeasts that modify deeply its natural chemistry through catabolism of existing compounds or introducing new ones. If pathogen infestation of milk continues to be a major problem, in part due to the formation of obnoxious exo and endotoxins and other products of their metabolism, the complex microcosm thriving in milk is also a source of opportunities for the dairy industry. Proper management and deep knowledge of the natural organic chemistry of milk and downstream dairy products can not only prevent product spoilage but also enhance its nutritional, nutraceutical, and taste qualities. This latter property is extensively being exploited to manufacture cultured creams, yogurts, spreads, and cheeses of ever growing sophistication, as are methods of analytical organic chemistry and quality control of milk feedstocks. In reviewing the literature of the past 25 years and up to mid-2016, this chapter emphasizes the natural product essence of milk as a biochemically living stuff of exceedingly complex and dynamic organic chemistry, subject to great variability considering the number of inputs from the outside of the mammal, internal processing of the ingested organic materials, microbial intervention in the digestive tract in healthy and diseased livestock, and the multifarious ripening of fermented dairy products that make them favorite foods for millions of people across the world.
The objective of this study was to characterise the sensory profile of goat milk and cheese evaluated in three different seasons on the basis of alcohols, ketones, esters and terpenes content and profile. For this purpose, a trained panel of eight people was used, which sniffed the pure compounds corresponding to those found in all the products.One group of 15 lactating goats grazed a local pasture from March to July. Daily grazing time was approximately 8h/day. During winter, spring and summer, herbage intake and the contribution of each species to the grazing diet were estimated by difference of herbage mass weight. Volatile organic compounds (VOC) content in herbage diet, milk and cheeses was determined by a multiple dynamic headspace extraction and GC–MS. The “fragrance” profile was described using the single pure compounds found in milk and cheese. The results showed that from winter to spring especially ketones content increased in milk, while no variation was observed for the other compounds. Summer milk was characterised mostly by terpenes.Also, the “fragrance” profile changed with grazing season. Winter milk was characterised by wood pulp-hay, green-herbaceous and blue-cheese notes, while in the spring by wood pulp-hay, blue-cheese, hot milk and musty. In the summer, the profile totally changed. In this season resinous, citrus, mint and fruity were the dominant notes.In comparison to herbage and milk, cheeses were less rich in volatile compounds. Not significant variation was observed in cheeses from a season to another, but their sensory profile was dominated by sweet odour.
The objective of this study was to evaluate the effect of the diet of grazing goats on the concentration and the profile of terpenes in their milk. This was tested during three seasons of the year using the two most preferred plant species in each season. Fifteen non-supplemented lactating goats grazed the pastures during the different seasons for 8 hours/day to measure their preference of specific plant species. The terpene concentration of the milk of six grazing lactating goats fitted with rumen cannulae were determined. For six consecutive days, 500 g/day of fresh herbage were introduced through the cannulae into their rumens, Lolium perenne and Dactylis glomerata in winter, Geranium molle and Asperula odorosa in spring and Cichorium intybus and Galium verum in summer. The results showed that each plant species modified the profile and the concentration of mono and sesquiterpenes of milk. In every season sesquiterpenes appeared the most abundant compounds. In summer the sesquiterpenes reached the highest levels, enriching goat milk most pronouncedly.
Antioxidants prevent oxidation of fatty acids in milk and meat. In the present study, the content of tocopherol antioxidants (vitamin E) in vegetative and reproductive parts of 22 grazing plants was estimated in two alpine areas used for summer farming. The overall mean content of α-tocopherol was 135 ± 34 μg g(-1) DW, and grasses had much lower content (28 ± 11 μg g(-1) DW) than herbs (215 ± 94 μg g(-1) DW), sedges (186 ± 78 μg g(-1) DW), and woody species (178 ± 52 μg g(-1) DW). Highest and lowest species-specific levels were 649 ± 91 and 2 ± 1 μg g(-1) DW, respectively. Plants from light and shady habitats did not differ in their α-tocopherol content, which was idiosyncratic as indicated by significant interactions between species, sampling occasion, site, and tissue type. Our results show that alpine ranges provide fodder with high levels of α-tocopherol.
L'étude des relations entres les compositions botaniques et en composés volatils de 10 végétations de montagne (situées entre 850 et 1800 m d'altitude) a permis de mettre en évidence plusieurs types de profils en composés volatils. Ces profils se distinguent par la richesse et la nature des composés volatils, notamment en terpènes. Ils ont pu être associés à des profils botaniques, en considérant les abondances respectives dans la végétation des graminées et des différentes familles de dicotylédones. Les végétations riches en graminées sont pauvres en composés volatils. Par contre, les végétations les plus riches en ombellifères sont les plus riches en terpènes.
The transfer of monoterpenes and sesquiterpenes from forages into milk fat was studied in a group of cows fed successively with forages containing high and low amounts of these substances. In a first 24-d period the cows received 11 kg of a cocksfoot hay containing low quantities of monoterpenes and sesquiterpenes. In a second 36-d period, 3 kg of the cocksfoot were replaced by 3 kg of yarrow, a plant rich in terpenoids. In a third 24-d period the cows returned to the cocksfoot-based diet they were fed in the first period. The quantities of monoterpenes and sesquiterpenes desorbed from the milk fat were measured by dynamic headspace - gas chromatography - mass spectrometry. Results showed that the quantities of monoterpenes had increased by the first milking carried out 8 h after ingestion of yarrow, whereas the increase in the quantities of sesquiterpenes was observed only after the third milking, 32 h after the diet change. The maximal quantities of monoterpenes and sesquiterpenes were measured after 4 d of the yarrow-enriched diet, after which the total quantities decreased, despite the constant supply of yarrow. Four days after discontinuing yarrow the amounts of monoterpenes and sesquiterpenes desorbed from the milk fat reverted to those measured during the first period.
This paper deals with the effects of farming systems linked to feeding aspects on the composition and quality of ewe and goat milk. When systems based on grazing and indoor systems are compared, the milk components (fat, protein, lactose) appear to be rather less influenced by type of farming system than by level of milk production. Significant differences are observed when ingested energy varies between pasture and indoor systems. Milk production depends on level of intake, and fat content on the indirect effect of dilution, while protein content varies generally like milk production. Goat milk production and its fat content can rise when grass is at an early growth stage. As in cows, fresh grass strongly influences the fatty acid contents of milk by increasing PUFA and CLA percentages. On cultivated pasture, the kind of fodder species, vegetation stage, season, and stocking rate can modify milk composition and quality. Natural pasture based farming systems produce milk rich in fat and in micro-components, which are beneficial to human health (fatty acids, vitamins), and in volatile components (flavour, terpenes). When three feeding systems based on natural pasture in the plain, on hills and on mountains are compared for goats, milk yield is slightly lower on mountain pasture but fat and protein contents and percentages of PUFA are higher, and the terpenes are more numerous in goat milk. Grass of natural pasture at an early stage produces milk richer in CLA. Supply of concentrates up to 0.6kg/day/goat grazing natural pasture does not seem to modify the contents of volatile compounds, terpenes and flavour in milk, but it should reduce retinol content. In intensive indoor systems, a high level of intake due to fodders of good nutritive value or to high supplies of concentrates enables production of milk rich in protein and relatively low in fat. The ratio of fat to protein percentages can be reversed particularly in mid-lactation, when goats are fed diets short of fibre or fat. Consequently, the quality of cheese (granular paste, lack of nice goat taste) is lowered. When supply of concentrates in diets increases to 60% of total dry matter intake, fat content may decrease slowly and linearly, but if concentrate intake reaches 60–80%, fat content may decrease rapidly due to an increasing shortage of fibrosity in the ration. Studies confirm that the milk fat content influences cheese fat content as well as rheological and sensorial qualities. Thus, this is an important factor, which has direct repercussion on cheese quality such as is appreciated by consumers. In the future, the farmer must select farming or feeding systems in accordance with trade conditions, consumers’ demand and socio-economic conditions. If commercialisation of high quality cheeses is possible, farmers will have to define systems, that allow to optimise parameters of quality, even by limiting milk production. In the future, the farmers have to find a balance between the level of intensification and the quality of dairy products.
Sixty Alpine crossbred goats were pastured on 14ha of shrub land and 14 Zebu cattle on 16ha of a tropical Legume forest with grasses, both groups supplemented with a slow-intake urea mixture (SIUS). Milk production was sustained by the SIUS supplement, when forage growth was reduced, thus avoiding over-grazing of the rangeland, and production of cheese by the farmer was assured. Artisan cheese was made from the non-pasteurized raw milk. During the spring and summer of 2004, cheese quality parameters of fatty acid contents and nutroceutical components in cheese made from the milk of grazing Zebu cattle or Alpine crossbred goats was studied, and compared with cheeses manufactured of milk from indoor fed animals. Monoterpene and sesquiterpene contents in spring in grazed Zebu cheese were 460 and 520ng/kg cheese, respectively, while indoor fed Zebu cattle had 126 and 210ng/kg. Goat cheese monoterpenes were 480ng/kg in the spring and 440ng/kg in the summer on grazed animals. Sesquiterpenes content in goat cheese were 1200ng/kg in the summer and 500ng/kg in the spring on pasture goats. Fat content was lower in grazed Zebu cattle cheese at 13.6g/100g cheese and cholesterol was 70.5mg/100g cheese, compared to 17.5g fat/100g cheese and 79.1mg/100g cheese for indoor fed Zebu cattle. Grazing caused higher tocopherol contents in cheese from grazing Zebu at 127mg/100g DM, compared to 77mg/100g DM in cheese from indoor fed cattle. Grazing also increased the linoleic acid content in Zebu cattle cheese (173mg/kg versus 140mg/kg/cheese) but especially in goat grazing up to 183mg/100g cheese. Differences between spring and summer were similar. Cheese fat and cholesterol contents were lower for grazing goats at 12.3g/100g cheese and 63.2mg/100g cheese, compared to 16.9g/100g cheese and 80.4mg/100g cheese for indoor fed goats, respectively. Grazing caused higher tocopherol contents in cheese from goats at 211mg/100g cheese, compared to 87mg/100g cheese, respectively, in indoor fed goat cheese. The presence of omega 3 and 6 distribution, were mostly better in GG and GC. Values of the series omega 3 fatty acids were higher in GG. Alfa linolenic-ALA and oleic acids had the highest concentration in GG cheese. The omega 6 fatty acids (total linolenic, eicosatrienoic and archiodenic) were higher in GG as compared to the other cheeses. Finally for cis-4,7,10,13,16,19-docosahexaenoico acid (DHA) in both indoor made cheeses presented higher concentrations compared with grazed made cheeses. FAME total concentration subdivided in saturated and monounsaturated, were significantly higher for IG and IC from GG and GC (P
Cattle diets that are low in lipids produce a hard milk fat high in the cheesy-flavored endogenous fatty acids and the precursors of the blue-cheese-flavored methyl ketones and of the coconut-peachy-flavored δ-lactones. The reverse is true for high lipid diets. Diets that induce a propionate metabolism in the rumen cause the formation of the sweet, raspberry - flavored γ - dodecanolactone from dietary oleic acid and of the sweet, raspberry-flavored γ-dodec-cis-6-enolactone from dietary linoleic acid. Lush pastures produce a richly colored milk fat and introduce phytol, dihydrophytol, phytenes, and phytadienes, and probably their lower homologues, into the milk fat. A protein-free synthetic diet lowers the animal-flavored indole and skatole, eliminates 2-enals (C3 to C12), and increases branched-chain and odd carbon-numbered δ-lactones and branched-chain and odd carbon-numbered fatty acids in the milk fat. Milk from pasture-fed cows is less susceptible to oxidation than milk pro-cows on dry feed. Most cows will produce spontaneously lipolyzing milk if their plane of nutrition is sufficiently low; milk from well-fed herds is seldom susceptible to spontaneous lipolysis. Poor quality silage and various weeds produce off-flavors in the milk due to direct transfer of off-flavors, to the breakdown products of weed components, or to the effect of components of the weeds on the biochemistry of the cow.
The objective of this study was to investigate the transfer of volatile terpenes from caraway seed and oregano plant essential oils into cow's milk through respiratory and gastrointestinal exposure. Essential oils have potential applications as feed additives because of their antimicrobial properties, but very little work exists on the transfer of their volatile compounds into milk. Lactating Danish Holstein cows with duodenum cannula were used. Gastrointestinal exposure was facilitated by infusing the essential oils, mixed with deodorized sesame oil, into the duodenum cannula. Two levels were tested for each essential oil. Respiratory exposure was facilitated by placing the animal in a chamber together with a sponge soaked in the essential oils. All exposures were spread over 9 h. Milk samples were collected immediately before and after exposure, as well as the next morning. Twelve monoterpenes and 2 sesquiterpenes were analyzed in essential oils and in milk samples using dynamic headspace sampling and gas chromatography-mass spectrometry. In the essential oils, almost all of the terpenes were detected in both essential oils at various levels. For caraway, the monoterpenes limonene, carvone, and carvacrol were most abundant; in oregano, the monoterpenes carvacrol and ρ-cymene were most abundant. For almost all treatments, an immediate effect was detected in milk, whereas little or no effect was detected in milk the following day. This suggests that the transfer into milk of these volatile terpenes is fast, and that the milk will not be influenced when treatment is discontinued. Principal component analysis was used to elucidate the effect of the treatments on the terpene profile of the milk. Terpene content for treatment milk samples was characterized by the same terpenes found in the treatment essential oil used for that animal, regardless of pathway of exposure. The terpenes appear to be transferred unaltered into the milk, regardless of the pathway of exposure. Volatile terpenes in essential oils, which could influence milk flavor, are transferred into milk via both gastrointestinal and respiratory exposure.
The composition and sensory characteristics of matured cheeses are controlled by
a number of factors, among which the type of feed is important. The influence of
feeding can be reflected by the presence in cheeses of terpenes and sesquiterpenes,
compounds typically indicating their vegetable origin (Mariaca et
al. 1997). Indeed,
several investigators have already established that these compounds could
characterize the forage even to a specific geographical location. Dumont & Adda
(1978), Dumont et
al. (1981), Guichard et
al. (1987),
Bosset et
al. (1994) and Moio et
al. (1996) were thus able to distinguish cheeses from lowland and upland regions. In
most of these studies, the conditions under which milk was produced and processed
were not completely controlled. Furthermore, all these studies analysed only the
volatile fraction of cheeses and did not examine the volatile compounds in the forages
used. Recently Bosset et
al. (1994), in one part of the project described by Jeangros
et
al. (1997), showed that highland grass with a highly diversified botanical
composition produces milk and cheeses with significantly different chemical
compositions from those from lowland grass. To improve our understanding of the
relationship between animal feed and cheese composition, we have investigated
under controlled experimental conditions both the composition of the terpene and
sesquiterpene fractions of four forages with different botanical diversities and the
influence of those forages on the terpene fraction of cheeses.
This paper examines the distribution of mono- and sesquiterpene secondary metabolites in 47 plants present in grazing areas from which cheeses are produced. In total, 54 terpenoid volatiles, derived from both highland and lowland plants, were obtained by a gaseous purge-and-trap system without the use of organic solvents and then identified by automated GC/MSD-FID analysis using mass spectral libraries, retention indices, and data acquired by the authors with authentic substances. Single ion monitoring proved valuable in identifying overlapping compounds with similar spectra for the subsequent semiquantitative determination of compositions. These are displayed as radar plots. It is suggested that flavor/aroma differences in cheeses produced from animals grazing in different areas and seasons arise from species (n = 38), phenological stages (n = 8), locations (n = 4), and seasonal variation in terpenoids present (the most common were trans-β-ocimene, limonene, and trans-β-caryophyllene). This hypothesis is supported by the fact that distinct variations in terpenoids with differing odor descriptors and abundances were found. It is also possible that terpenes with a higher polarity are less efficiently recovered by the purge-and-trap method than compounds of lower polarity. As the radar plots display relative concentrations based on detection limits, the relative efficiency of detection for different classes of compounds needs to be taken into consideration. Keywords: GC/MS; flavor; volatile; monoterpene; sesquiterpene; plant; highland; lowland; pasture; retention index
This review summarises the last 10 years' knowledge established on the relationships between the management of animals (genetics, physiology and feeding) and the sensory quality of cheese. In the production of full-fat raw milk cheese, the cow's breed can modify the texture of cheeses because of differences in fat in dry matter content due to variations in the fat/protein ratio in milk. Within the same breed, large differences in texture and taste were observed between cheeses issued from milk differing by the genetic variant of -casein (in dairy cows) or s1- casein (in goats). Except in very early or late lactation, the physiological stage had no significant effect on cheese sensory characteristics. In contrast, mastitis has a well-known negative impact on cheese sensory properties. Feeding dairy cows or goats with corn silage by comparison with hay or grass silage leads to whiter cheeses and sometimes to differences in flavour. Conserving grass as silage, by comparison with hay, has no important effect on cheese sensory characteristics, except on colour, which is yellower with grass silage. Conversely, major differences in sensory characteristics were observed between cheeses made with milk produced by cows fed winter diets (based on hay and grass silage) or turned to pasture in the spring. Several recent experiments showed a significant effect of grass' botanical composition on cheese texture and flavour. Those effects are due to the presence in milk of specific molecules or structures directly induced by feeding (carotenes and terpenes) or produced by the animals (plasmin, fatty acids and casein micellar structures) according to their genetic or physiological characteristics or under the effect of specific diets.
Thirty-five representative samples of milk from either a highland area of France (Auvergne region) or a lowland area of France (Brittany region) were collected in spring and summer (grazing periods), and in winter (stabling period). The monoterpenes and sesquiterpenes extracted from the milk fat were semi-quantified by dynamic headspace–gas chromatography–mass spectrometry (DHS-GC-MS). Milk samples were classified by factorial discriminant analysis. Milk collected in the Auvergne highland area was richer in sesquiterpenes than that collected in the Brittany lowland area. All the samples were correctly classified according to their geographical origin irrespective of seasonal herd management pattern. These findings show that the assay of terpene compounds can provide useful fingerprints for the characterization of dairy produce according to geographical area and production conditions.
The production of volatile aroma compounds from the cheese associated fungus Penicillium caseifulvum has been compared to the aroma production by P. camemberti when grown on a liquid cream based medium in Petri dishes. Volatiles were collected by diffusive sampling between day 5 and 10 and between day 10 and 15 and analysed by gas chromatography coupled to mass spectrometry. During both sampling periods similar qualitative aroma profiles could be observed for the two species. In the beginning volatiles like ethanol, acetone, 2-methylpropan-1-ol, 2-pentanone, 3-methylbutan-1-ol, 2-heptanone, 2-nonanone and 2-undecanone were dominant, whereas the metabolism changed later in the growth phase. At this stage unsaturated hydrocarbons like styrene, limonene, β-caryophyllene and other terpenoids, including some possible diterpenes, were major volatiles. The results indicate the potential of P. caseifulvum as a new starter culture for the dairy industry or as a fermentation organism for production of natural cheese flavours by submerge fermentation.
HS-SPME analysis of terpenes does usually have inherent quantification problems when working with complex samples, especially due to the matrix effect of the substrate or the calibration solution. Three different terpene carrier matrices were compared: methanol, synthetic oil and milk fat obtained by centrifugation from milk cream. Considerable differences in calibration sensitivity parameters were observed depending on the matrix used and on the type of terpene standard analysed. For milk sample quantification purposes internal standard method was preferred using milk fat as calibration matrix. Linearity range, repeatability, recovery and limits of detection and quantification were determined. Validation parameters were different depending on the concentration and molecular structure of each terpene analysed, particularly between mono- and sesquiterpenes. The method was useful to determine in an accurate manner the terpene content in milk samples from pasture fed animals, and it will help to establish objective terpene levels to differentiate milks from specific production systems.
Headspace sorptive extraction (HSSE) combined with thermal desorption (TD), gas chromatography (GC) and mass spectrometric detection (MSD) was applied to determine the volatile compounds of an Italian mountain cheese (Bitto) with protected designation of origin. Samples were taken from local dairy farms in Valtellina (Northern Italy), in which goats and cows were grazing on pastures during summer.A total of 84 compounds that belong to the following chemical families were detected and identified: aldehydes (17), ketones (10), esters (15), fatty acids (12), alcohols (11), terpenes (11) and hydrocarbons (8).The impact of each volatile compound on the flavour profile of Bitto cheese was discussed. The flavour profile of this cheese is important for the producer who wants to claim the right of naming cheese manufactured in a specified restricted area. Actually, this approach might become mainly useful for products, like Bitto cheese, with a PDO registration.HSSE coupled with thermal desorption and GC–MS analysis provided a versatile tool for the analysis of volatiles in cheese.
The influence of seasonal variation of diets (conserved forage and pasture) on fatty acid (FA) and terpenoid profiles of bovine milk and “Toma piemontese” cheese was studied in a Piedmont mountain farm, under the usual conditions of farming and management of herds in the highlands. The dairy products obtained in summer from pasture-based diets presented a more favourable FA profile. Compared with winter, summer milk had lower contents of saturated FA (SFA) (−15.8%) and higher contents of monounsaturated FA (MUFA) (+33.0%), polyunsaturated FA (PUFA) (+68.2%), conjugated linoleic acid (CLA) (+161%) and vaccenic acid (+148%). The milk from pasture-based diets presented higher contents of terpenes than did that from winter diets based on hay. Processing milk into ripened cheese had no effect on the FA composition and terpene profile of dairy products. These molecules can confer specific organoleptic and nutritional properties to the dairy products that provide an added value to the product and justify its higher price.
Minas cheese is a food product of significant economic importance to the Brazilian dairy industry. With the intent of providing product identity for legal, economic and manufacturing purposes, several studies have been conducted to define the proximate composition, starter and ripening microflora and manufacturing protocol for Minas cheese. However, studies have yet to characterize the flavor character of Minas cheese, namely the volatile profile. For this purpose, volatiles were investigated using dynamic headspace sampling and GC-MS analysis. Quantitation was based on the recovery of authentic compounds where available. A total of 54 compounds were positively identified and 51 quantified, including fatty acids (11), alcohols (14), aldehydes (5), ketones (6), esters (7), terpenes (8) and lactones (2). The impact of individual volatile compounds on the flavor profile of Minas cheese is discussed. Some of major metabolic pathways for their biosynthesis are reviewed to indicate the possible origin of the compounds identified.
Resting cells of a locally isolated strain of Aspergillus niger caused the bioconversion of alpha pinene to verbenone. The formation of verbenone was raised from trace amounts (under screening conditions) to 3.28 mg/100 ml (equivalent to a molar yield of 16.5% conversion of the substrate) by amending the cultivation medium for the fungus. The optimal conditions were: 6 g/100 ml for the glucose concentration, a pH of 7.0, an alpha pinene concentration of 20 mg/100 ml, and a 6-h incubation period for the reaction.
The volatile components from nine plants growing on natural grasslands in Auvergne, central France, selected for the broad qualitative and quantitative diversity of their terpenoid fractions, were analyzed by high-resolution gas-phase chromatography and mass spectrometry (HRGC-MS) after static headspace solid-phase microextraction (SHS-SPME). SHS-SPME allowed all the plant material to be analyzed under the same conditions despite its wide-ranging composition. This is not always possible with other extraction methods. Using an apolar poly(dimethylsiloxane) (PDMS) phase, numerous terpenoid hydrocarbons, together with alcohols, cyclic ethers, and esters, were extracted. Its ease of use and the high resolution of the chromatographic profiles obtained make SHS-SPME well suited to the rapid characterization of the main components of the volatile fraction of plants. Of the nine plants studied, four (Meum athamanticum, Pimpinella saxifraga, Achillea millefolium, and Thymus pulegioides) exhaled more than 60 different volatile components. Certain terpenes present in large amounts in these plants might help link dairy products to grazing pasture, thus improving food traceability.
The microorganisms involved in cheese ripening produce various volatile compounds and induce typical flavors that contribute to cheese variety. To investigate aroma compound generation of cheese microflora, we used a dynamic headspace-gas chromatography-mass spectrometry analysis. To obtain good sensitivity and repeatability of quantification, dynamic headspace conditions and sample preparation were first optimized and led to an extraction set up in which samples were heated at 60 degrees C and diluted with water without pH adjustment. Then three different yeasts and three Geotrichum candidum commonly used in mold surface ripened cheeses were studied in pure culture in a cheese model medium. Thirty-nine cocultures of these three yeasts, the three G. candidum, and five bacteria were studied in the same medium to assess the interaction between microorganisms on aroma compound production. Twenty-four volatile compounds belonging to different chemical classes (alcohols, aldehydes, esters, sulfides, terpenes) were identified and quantified. Yeasts and especially Kluyveromyces lactis produced large amounts of alcohols, aldehydes, esters, and terpenes when cultured alone or in association. Geotrichum candidum and especially G. candidum strain G3 generated the largest amount of sulfides when cultured alone or in association. Finally, bacteria also produced aroma compounds but, except for Brevibacterium linens strain B5, which produced dimethyl trisulfide and ketones, no specific trend in the production of particular aroma compounds could be evidenced.
An automatic purge and trap apparatus, coupled to a GC-MS was used to study the seasonal variability of the volatile fraction of raw milk Manchego cheese. Both season and dairy significantly affected abundance of most volatile compounds. Most aldehydes, methyl ketones, n-alcohols, and secondary alcohols reached significantly higher concentrations in spring cheeses. Branched chain alcohols showed significantly higher concentrations in autumn and winter cheeses, while significantly higher amounts of diketones were found in summer cheeses. Most ethyl esters reached higher concentrations in spring and winter cheeses and lower in autumn cheeses. Lower concentrations of alpha-pinene were found in spring cheeses, and higher amounts of limonene were observed in winter cheeses. Heptane and octane were significantly more abundant in summer cheeses. No significant seasonal differences were found either for quality or intensity scores.
In vitro studies have demonstrated antibacterial activity of essential oils (EOs) against Listeria monocytogenes, Salmonella typhimurium, Escherichia coli O157:H7, Shigella dysenteria, Bacillus cereus and Staphylococcus aureus at levels between 0.2 and 10 microl ml(-1). Gram-negative organisms are slightly less susceptible than gram-positive bacteria. A number of EO components has been identified as effective antibacterials, e.g. carvacrol, thymol, eugenol, perillaldehyde, cinnamaldehyde and cinnamic acid, having minimum inhibitory concentrations (MICs) of 0.05-5 microl ml(-1) in vitro. A higher concentration is needed to achieve the same effect in foods. Studies with fresh meat, meat products, fish, milk, dairy products, vegetables, fruit and cooked rice have shown that the concentration needed to achieve a significant antibacterial effect is around 0.5-20 microl g(-1) in foods and about 0.1-10 microl ml(-1) in solutions for washing fruit and vegetables. EOs comprise a large number of components and it is likely that their mode of action involves several targets in the bacterial cell. The hydrophobicity of EOs enables them to partition in the lipids of the cell membrane and mitochondria, rendering them permeable and leading to leakage of cell contents. Physical conditions that improve the action of EOs are low pH, low temperature and low oxygen levels. Synergism has been observed between carvacrol and its precursor p-cymene and between cinnamaldehyde and eugenol. Synergy between EO components and mild preservation methods has also been observed. Some EO components are legally registered flavourings in the EU and the USA. Undesirable organoleptic effects can be limited by careful selection of EOs according to the type of food.
The traceability of Asiago mountain cheese was established by analyzing samples of herbaceous species, milk, and cheese of mountain origin using the head-space solid-phase microextraction sampling procedure coupled with gas chromatography-mass spectrometry. As preliminary work had highlighted the characteristic presence of sesquiterpenes in Asiago mountain cheese, these species were considered effective markers of mountain origin. Systematic qualitative analysis, carried out using a carboxen/polydimethylsiloxane fiber, revealed several sesquiterpenes in mountain herbage and milk, in particular beta-caryophyllene and alpha-humulene, in Asiago mountain cheese, confirming sesquiterpenes as markers of cheese produced from animals grazing on mountain pastures. Analysis was performed on 19 samples of herbage, 8 of milk, and 8 of cheese, collected in summer from 4 mountain farms on the Asiago plateau. For quantitative analysis of caryophyllene in cheese, polydimethylsiloxane fiber sampling, coupled with the standard addition method to eliminate matrix effect, was preferred. The amount of beta-caryophyllene found ranged from 21 to 65 microg/kg.
Changes of terpene content in milk from cows grazing natural diversified upland pasture were examined in this observational trial. A homogeneous plot divided into 2 subplots was used from May 31 to July 1, 2003 (first growth) and again from October 1 to October 7, 2003 (vegetative regrowth). Each subplot was grazed by 6 dairy cows in 2 ways: strip grazing (SG), with new allocations of pasture strips at 2-d intervals, and paddock grazing (PG). The PG subplot was divided into 3 paddocks and the cows were moved to a new paddock on June 13 and June 24, 2003. Milk from the 6 cows was collected twice a week, pooled, and used for terpene analyses by dynamic headspace gas chromatography-mass spectrometry system. Twenty mono- and 23 sesquiterpenes desorbing from the milk fat were separated. The most abundant monoterpenes were beta-pinene, alpha-pinene, gamma-terpinene, limonene, alpha-tujene, terpinolene, and alpha-phellandrene. The most abundant sesquiterpenes were beta-caryophyllene, alpha-copaene, beta-cedrene, transmuurola-4-(14)-5-diene, beta-bisabolene, and delta-cadinene. Both mono- and sesquiterpenes in SG milk increased across time with an 8-fold increase in total terpenes in milk from the beginning to the end of June. In parallel, dicotyledons, including the main terpene-rich plants, increased from 17 to 31% of total biomass of the vegetation and the development of Dactylis glomerata progressed from boot to ripening stage. The terpenes in PG milk were equivalent to those in SG milk for the first paddock at the beginning of June and remained constant or doubled for the sum of mono- and sesquiterpenes, respectively. The lower variability of the PG milk terpene content could be related to the opportunity that PG cows had to choose ingested herbage, whereas the SG cows had limited choice within the smaller allocated pasture strips. Milk from cows grazing regrowth pastures in October contained low levels of terpenes, and values were similar for PG and SG milks. Change in the sum of monoterpenes is representative of changes for most monoterpenes (except for limonene) and, conversely, the change in the sum of sesquiterpenes mainly reflected changes in beta-caryophyllene and alpha-copaene. In addition to effects of botanical composition of pasture, it appears that terpene content in milk may vary according to factors linked to grazing management that need more intensive study. Nevertheless, current results raise questions about the precision of terpenes as feed tracers.
Four Italian cheeses (Casciotta di Urbino, Barricato San Martino, Vento d'Estate, and Ubriaco di Raboso) nonconventionally ripened under different plant materials (walnut leaves, herbs, hay, and wine by-products, respectively) were compared for compositional, microbiological, biochemical, and volatile profile characteristics. Mean values for gross composition were rather similar. Because primary starters were not used for manufacture, the endogenous lactic acid bacteria were mainly present (7.0 to 9.0 log10 cfu/g). Except for Lactobacillus paracasei and Leuconostoc mesenteroides, which were commonly identified in 3 cheeses, Lactococcus lactis, Enterococcus sanguinicola, Lactobacillus brevis, Enterococcus durans/Enterococcus faecium, Lactobacillus plantarum, and Weissella cibaria/Weissella confusa were variously found in the 4 cheeses. Random amplification of polymorphic DNA-PCR analysis showed the biodiversity among the strains, and the species of lactobacilli were in part grouped according to their origin. As shown by the principal component analysis of reverse-phase fast protein liquid chromatography data for the pH 4.6-soluble fractions and by the determination of free AA, the secondary proteolysis of Barricato San Martino and Vento d'Estate mainly differed from the other 2 cheeses. Purge-and-trap and solid-phase microextraction were coupled with gas chromatography-mass spectrometry to determine volatile compounds. Vento d'Estate showed the highest levels of almost all chemical classes, and Casciotta di Urbino was characterized by a very low level of volatile components. Esters, ketones, and terpenes were the chemical classes that mainly differentiated the cheeses. Several volatile compounds seemed to be released directly from the plant materials used for ripening, especially terpenes for Vento d'Estate cheese. The lowest level of volatile free fatty acids was found in Casciotta d'Urbino, in which rennet paste was not used during manufacture. The highest concentration of free fatty acids, especially butyric and caproic acids, was found in Vento d'Estate cheese.
The aim of this experiment was to study the effect of the addition, to milk, of an essential oil (EO) obtained from the hydrodistillation of plants collected from a mountain natural pasture on the milk and cheese sensory properties. The EO was mainly composed of terpenoid compounds (67 of the 95 compounds identified) as well as ketones, aldehydes, alcohols, esters, alkanes, and benzenic compounds. In milk, the addition of this EO at the concentration of 0.1 microL/L did not influence its sensory properties, whereas at 1.0 microL/L, sensory properties were modified. In cheeses, the effect of adding EO into milk was studied in an experimental dairy plant allowing the production of small Cantal-type cheeses (10 kg) in 3 vats processed in parallel. The control (C) vat contained 110 L of raw milk; in the other 2 vats, 0.1 microL/L (EO1) or 3.0 microL/L (EO30) of EO were added to 110 L of the same milk. Six replicates were performed. After 5 mo of ripening, chemical and sensory analyses were carried out on the cheeses, including determination of the volatile compounds by dynamic headspace combined with gas chromatography-mass spectrometry. The EO did not influence the sensory properties of the cheeses at the lower concentration (EO1). However, the EO30 cheeses had a more intense odor and aroma, both characterized as "mint/chlorophyll" and "thyme/oregano." These unusual odors and aromas originated directly from the EO added. In total, 152 compounds desorbing from cheese were found, of which 41 had been added with the EO; in contrast, 54 compounds of the EO were not recovered in the cheese. Few volatile compounds desorbing from cheeses, other than the added compounds, were affected by EO addition. Among them, 2-butanol, propanol, and 3-heptanone suggested a slight effect of the EO on lipid catabolism. The antimicrobial activity of terpenes is not or is only marginally involved in the explanation of the influence of the botanical composition of the meadows on the pressed cheeses sensory properties.