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L-Theanine As a Functional Food Additive: Its Role in Disease Prevention and Health Promotion

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L-Theanine As a Functional Food Additive: Its Role in Disease Prevention and Health Promotion beverages Review L-Theanine as a Functional Food Additive: Its Role in Disease Prevention and Health Promotion Jackson Williams 1, Jane Kellett 1, Paul Daniel Roach 1,2, Andrew McKune 1,3, Duane Mellor 1, Jackson Thomas 1 and Nenad Naumovski 1,2,* 1 Faculty of Health, University of Canberra, Canberra, ACT 2601, Australia; [email protected] (J.W.); [email protected] (J.K.); [email protected] (P.D.R.); [email protected] (A.M.); [email protected] (D.M.); [email protected] (J.T.) 2 School of Environmental and Life Sciences, University of Newcastle, Ourimbah, NSW 2258, Australia 3 Research Institute for Sport and Exercise (UCRISE), University of Canberra, Canberra, ACT 2601, Australia * Correspondence: [email protected]; Tel.: +61-2-6206-8719 Academic Editor: Quan V. Vuong Received: 23 April 2016; Accepted: 23 May 2016; Published: 30 May 2016 Abstract: Tea has been consumed for thousands of years and is an integral part of people’s daily routine, as an everyday drink and a therapeutic aid for health promotion. Consumption of tea has been linked to a sense of relaxation commonly associated with the content of the non-proteinogenic amino acid theanine, which is found within the tea leaves. The aim of this review article is to outline the current methods for synthesis, extraction and purification of theanine, as well as to examine its potential benefits related to human health. These include improvements in cognitive and immune function, cancer prevention, reduced cardiovascular risk and its potential usefulness as a functional food product. Keywords: theanine; green tea; alpha wave production; relaxation; functional food, bioactives 1. Introduction Tea is a one of the most widely consumed beverages in the world, second only to water [1]. Derived from the Theaceae family, the Camellia sinensis species is commonly used for the production of green tea (GT) [2]; it accounts for up to 22% of tea produced and consumed worldwide [3,4] and it is predominantly grown in Asian countries. Historically, tea consumption has been associated with relaxing effects [5]. More recently, numerous other health benefits, including but not limited to antioxidant, antimutagenic, and anticarcinogenic effects have been identified for its constituents such as the polyphenols (catechins), caffeine and other flavonoids. These compounds may account for up to 30% of the dry weight [1]. Twenty-six different amino acids have been reported and identified in GT plants [6], with the most abundant being N-ethyl-L-glutamine, glutamic acid and aspartic acid [7]. N-ethyl-L-glutamine, commonly referred to as L-Theanine (L-THE) [8], is most commonly found in GT leaves, although it has also been identified in the basidiomycete mushroom (Xerocomus badius), at much lower concentrations [8]. In the late 1940s, L-THE was isolated as an extract from an aqueous solution of dried tea leaves [9]; however, L-THE was first chemically synthesised from pyrrolidonecarboxylic acid and aqueous ethylamine [10]. Currently, there is substantial interest in L-THE and several potential health benefits have been attributed to it. This narrative review will focus on the chemical and physical properties of L-THE, and its impact on human health in general, including but not limited to its usefulness as a functional food additive. Beverages 2016, 2, 13; doi:10.3390/beverages2020013 www.mdpi.com/journal/beverages Beverages 2016, 2, 13 2. L‐THE in Nature Beverages 2016, 2, 13 2 of 16 The relative concentration of L‐THE in the Camellia sinensis plant varies between the plant’s structures, over maturation and through the growth period. Recent studies have indicated that 2.L‐THEL-THE is distributed in Nature across the entirety of the plant with concentrations ranging between 1.2 and 6.2 mg/gThe relativefresh weight, concentration with higher of Lconcentrations-THE in the Camellia being expressed sinensis plant in the varies roots between(6.2–13.7 themg/g). plant’s The structures,biosynthesis over of maturationL‐THE is proposed and through to occur the growth in the period. roots Recentof the studiesplant and have it indicatedis then transported that L-THE istowards distributed the leaves across the[11]. entirety The shading of the plant treatment with concentrations and nitrogen rangingfertilisation between have 1.2 been and shown 6.2 mg/g to freshinfluence weight, the with L‐THE higher levels concentrations and the total being free expressedamino acid in thecontent roots in (6.2–13.7 the Camellia mg/g). sinensis The biosynthesis plant [12]. ofAlthoughL-THE is most proposed often to related occur into theGT, roots L‐THE of the is present plant and at it similar is then levels transported in other towards types the of leavesteas made [11]. Thefrom shading the plant, treatment including and black, nitrogen white fertilisation and oolong have teas been [13]. shown to influence the L-THE levels and the total free amino acid content in the Camellia sinensis plant [12]. Although most often related to GT, 3. Chemical, Physical and Flavour Properties L-THE is present at similar levels in other types of teas made from the plant, including black, white and oolongL‐THE teasis a [13water]. soluble non‐proteinous amino acid [14] containing a glutamine backbone within the core of L‐THE as well as existing as an ethylamide derivate of glutamate [15]. It is stable in 3. Chemical, Physical and Flavour Properties acidic conditions but yields glutamic acid and ethylamine during base hydrolysis [8,16]. L‐THE is insolubleL-THE in is organic a water solvents soluble such non-proteinous as chloroform amino and acid methanol, [14] containing which facilitates a glutamine the backbone easy separation within theof L‐ coreTHE of from L-THE caffeine, as well catechins as existing and other as an lipophilic ethylamide tea derivateconstituents of glutamate [8]. Aqueous [15 ].L‐THE It is solutions stable in acidic(1% (w/v)) conditions stabilised but yieldsat pH glutamic5–6, were acid found and to ethylamine be stable during(>1 year) base under hydrolysis normal [ 8environmental,16]. L-THE is insolubleconditions in [8,16,17] organic solventsand have such a boiling as chloroform point higher and methanol, than that which of water facilitates (range the 214 easy–216 separation °C) [8]. ofFurthermore,L-THE from caffeine,its systematic catechins nomenclature and other lipophilic is described tea constituents as (2 [S8].)‐2 Aqueous‐amino‐5L‐(ethylamino)-THE solutions‐5‐ (1%oxopentanoic (w/v)) stabilised acid (C7 atH14 pHN2O 5–6,3, M.W.= were found174.2 tog/mol) be stable [18]. (>1Gamma year)‐glutamylethylamide under normal environmental [18] and conditionsL‐glutamic [acid8,16‐,gamma17] and‐ethylamide have a boiling have pointalso been higher used than to thatdenote of waterL‐THE (rangeand it 214–216is also available˝C) [8]. Furthermore,under the proprietary its systematic name nomenclature Suntheanine® is [5,19]. described Similar as (2toS other)-2-amino-5-(ethylamino)-5-oxopentanoic amino acids in nature, theanine is a acidchiral (C species7H14N 2andO3, occurs M.W. predominantly = 174.2 g/mol) as [18 the]. L Gamma-glutamylethylamide‐(S) enantiomer (Figure 1), whereas [18] and a syntheticallyL-glutamic acid-gamma-ethylamidederived theanine is typically have a racemic also been mix used of L‐ toand denote D‐enantiomers.L-THE and As it such, is also the available use of synthetically under the proprietaryderived theanine name Suntheaninemay not necessarily® [5,19]. Similarexhibit tothe other same amino physiological acids in nature,effects theanineas theanine is a found chiral species“naturally” and occursoccurring predominantly in foods [8]. as the L-(S) enantiomer (Figure1), whereas a synthetically derived theanineL‐THE is typically is reported a racemic to induce mix sweetness of L- and alongD-enantiomers. with a unique As such, “umami the” use taste of on synthetically the palate [5]. derived This theanineis attributed may to not its capacity necessarily to bind exhibit with the the same T1R1 physiological + T1R3 umami effects taste asreceptors theanine and found giving “naturally” a similar occurringtaste sensation in foods to that [8]. of monosodium glutamate [5,20,21]. Figure 1. Chemical structure of L-THE. Adapted from [5]. Figure 1. Chemical structure of L‐THE. Adapted from [5]. L-THE is reported to induce sweetness along with a unique “umami” taste on the palate [5]. This is 4. Extraction and Synthesis of L‐THE attributed to its capacity to bind with the T1R1 + T1R3 umami taste receptors and giving a similar taste sensationL‐THE to thatcan ofbe monosodium obtained in glutamatethree ways: [5,20 extraction,21]. from tea leaves, chemical synthesis or biosynthesis. 4. Extraction and Synthesis of L-THE L 4.1. IsolationL-THE of can ‐THE be obtainedfrom Tea in three ways: extraction from tea leaves, chemical synthesis or biosynthesis.Isolating L‐THE from tea leaves has been proposed as an alternative method for industrial scale L‐THE production compared to chemical and enzymatic synthesis. This includes, extraction of GT 4.1. Isolation of L-THE from Tea leaves using ethyl acetate followed by isolation of L‐THE using preparative high performance liquid chromatographyIsolating L-THE (HPLC), from yielding tea leaves an extract has been containing proposed around as an 500 alternative g/kg L‐THE method [8]. However, for industrial even scale L-THE production compared to chemical and enzymatic synthesis. This includes, extraction of GT leaves using ethyl acetate followed by isolation of L-THE using preparative high performance liquid chromatography (HPLC), yielding an extract2 containing around 500 g/kg L-THE [8]. However, Beverages 2016, 2, 13 3 of 16 even though this procedure provides a final L-THE product with relatively high purity, excessive production cost and lower overall yield makes this methodology less appealing to the industry [22].
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