Enzymatic Acylation of Isoorientin and Isovitexin from Bamboo-Leaf Extracts with Fatty Acids and Antiradical Activity of the Acylated Derivatives

Ma, Xiang; Yan, Rian; Yu, Shuqi; Lu, Yuyun; Li, Zhuo; Lu, Haohao

doi:10.1021/jf303595e

Cited by 44 publications

(53 citation statements)

References 37 publications

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“…activated molecular sieves (30-150 g/l) were also employed for water removal in order to drive the reaction toward biosynthesis. Reactions were incubated at 60 °C with agitation (210 rpm) for 48 h [9,12,14]. Reaction bioconversion was monitored by HPlC to confirm production, with bioconversion (%) calculated following HPlC analysis as the area of the ester product divided by the total isoorientin and its ester area, multiplied by 100.…”

Section: Isolation Of Isoorientinmentioning

confidence: 99%

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Enzymatic acylation of isoorientin isolated from antioxidant of bamboo leaves with palmitic acid and antiradical activity of the acylated derivatives

Qian

2014

Eur Food Res Technol

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to a wide range of health benefits. In fact, anti-allergenic, anti-microbial, anti-inflammatory, anti-fungal, anti-tumoral properties [1][2][3][4] have all documented for flavonoids, yet it is their anti-oxidative related properties [5,6] which have really generated the most interest to date.The use of flavonoids in numerous cosmetic and pharmaceutic formulations seems very attractive. Unfortunately, the development of such products is seriously limited due to their poor solubility in lipophilic media thus limiting their use in oil-based foods and cosmetics. a solution to improve the hydrophobic nature of flavonoids consists in the esterification of the hydroxyl functions by fatty acids. Studies [7][8][9][10][11][12] have been investigated chemical and enzymatic acylation to improve flavonoid properties.The increasing concern of the consumers for food safety has pushed industries to the elimination of synthetic additives and their replacement by natural additives. The antioxidant of bamboo leaves (aOB), which is the trade name of bamboo-leaf extracts, has been approved as a natural food additive for food, edible oils, fried food and vegetable juices by Chinese Ministry of Health. The functional components of aOB include flavonoids, lactones and phenolic acids, and the highest content compound is isoorientin [13]. However, its use is also limited by weak solubility in lipidic matrices. To our knowledge, enzymatic acylation of flavonoids from aOB has seldom been studied.In order to evaluate and exploit the potential of the esters of aOB fully, it is extremely important to establish a simple, effective and relatively cheap method for preparation of esters for such testing. as such, this paper focuses on the optimization of enzymatic acylation of isoorientin from aOB by different lipases in different conditions with palmitic acids as acyl donor. AbstractThe utilization of bamboo-leaf extracts is limited by their weak solubility in lipidic media. as such, this study established an effective and relatively cheap method for preparation of ester of isoorientin isolated from bamboo-leaf extracts. acylation of isoorientin with palmitic acid was efficient in a system containing dried tert-amyl alcohol and molecular sieves, yielding from 22 to 90 % bioconversion with different conditions; in detail, several factors (the origin and the amount of the lipase, temperature and water content of the system) were investigated in depth with the effect on the performance of the acylation reaction in this paper. Thereafter high purity ester (95 %) was obtained following a two-step solvent purification procedure and a chromatographic separation. With 1 H and 13 C nuclear magnetic resonance spectroscopy analysis, single product was detected to be 6″-O-palmitate isoorientin ester. Introducing an acyl group into isoorientin significantly improved its lipophilicity yet slightly reduced their antioxidant activity.

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Section: Isolation Of Isoorientinmentioning

confidence: 99%

“…The injection volume was 20 μl, while the column temperature was maintained at 30 °C. Different compounds were quantified at 330 nm with the UV detector [14].…”

Section: Purification Of Ester Productsmentioning

confidence: 99%

Enzymatic acylation of isoorientin isolated from antioxidant of bamboo leaves with palmitic acid and antiradical activity of the acylated derivatives

Qian

2014

Eur Food Res Technol

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“…在黄酮类化合物改性中, 常用的方法有生物催化 [11,12] 和化学催化 [13,14] . 相比于化学方法修饰, 酶催化改性的方法具有反应条件温和、选择性高、操作简单等特点, 特别是对于多官能团的黄酮类天然产物改性而言, 酶催化因具有高的区域选择性和立体选择性而具有明显优势 [15] .…”

Section: 强的抑制活性unclassified

Synthesis of Novel Fatty Amide Analogues of Troxerutin Catalyzed by Lipase in Organic Medium

王宏雁¹,

杨亮茹²,

肖咏梅³

et al. 2014

Chin. J. Org. Chem.

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In nonaqueous medium, a series of troxerutin amidation analogues were synthesized by the reaction of vinyl-troxerutin esters with fatty amines. The influence parameters including enzyme source, the amount of the enzyme, reactive medium, water content of solvents and reaction time were investigated. The results showed that the amidation occurred regioselectively at vinyl-ester bond. Using pyridine as solvent (water content ＜1%), the amidation reaction catalyzed by lipase LS-10 (20 mg/mL) reached plateau after 21 h at 50 ℃.

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“…"Patriot," we used this compound A c c e p t e d M a n u s c r i p t 6 as the reaction subject. Maused lauric and tetradecanoic acids to acylate bamboo leaf flavonoid and found that lauric acid showed better effects on glucoside in an acylation reaction [29] . Thus, we selected lauric acid as the acylating agent.…”

Section: Introductionmentioning

confidence: 99%

Direct Acylation of Cyanidin-3-Glucoside with Lauric Acid in Blueberry and Its Stability Analysis

Zhao

Chen

Wang

et al. 2015

International Journal of Food Properties

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dong Sun (2015): Direct acylation of cyanidin-3-glucoside with lauric acid in blueberry and its stability analysis, International Journal of Food Properties, ABSTRACTCyanidin-3-glucoside (C3G) is an anthocyanin that is abundant in blueberry. Lauric acid was used as the acyl donor in the acylation of C3G. Preparative high performance liquid chromatography was used to separate and purify the acylated C3G, the acylated rate was 30.78%. Fourier transform infrared spectroscopy and liquid chromatography mass spectrometry were used to confirm the basic structure of C3G. Lauric acid was combined with C3G. Lauric acid reacted with the glucoside's primary hydroxyl group and removed a molecule of water, thereby resulting in the obtained structure. The compositions of the unacylated C3G and acylated C3G were compared Downloaded by [New York University] at 00:42 22 June 2015 A c c e p t e d M a n u s c r i p t 2 under different temperatures and under illumination. The effects of different concentrations of additive compounds on the stability of acylated C3G were compared. Stability of acylated C3Gwas obviously higher than that of the unacylated C3G because of the higher stability of the ester group than the hydroxyl group. The primary hydroxyl esterification of glucoside improved C3G.

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Enzymatic Acylation of Isoorientin and Isovitexin from Bamboo-Leaf Extracts with Fatty Acids and Antiradical Activity of the Acylated Derivatives

Cited by 44 publications

References 37 publications

Enzymatic acylation of isoorientin isolated from antioxidant of bamboo leaves with palmitic acid and antiradical activity of the acylated derivatives

Enzymatic acylation of isoorientin isolated from antioxidant of bamboo leaves with palmitic acid and antiradical activity of the acylated derivatives

Synthesis of Novel Fatty Amide Analogues of Troxerutin Catalyzed by Lipase in Organic Medium

Direct Acylation of Cyanidin-3-Glucoside with Lauric Acid in Blueberry and Its Stability Analysis

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