An on-line analysis method determining chemical reaction process based on an HPLC automatic sampling system was developed to study the products and reaction rates of 6′,7′-epoxybergamottin (6′,7′-EB) acid-induced reaction in simulated citrus juices with different acidity. The automatic pretreatment of imitated juice was programmed to ensure complete reaction at 25 ℃ and pH 2.0, 3.5 and 5.0, respectively; chromatographic conditions were optimized to separate the reactant and main products fully. Therefore, periodic sampling and analysis of these compounds in the reaction system was realized. Qualitative and quantitative detection of each substance was carried out by a diode array detector using the external standard method. At 25 ℃ by acid catalysis, 6′,7′-EB mainly involved in side-chain epoxide ring-opening and hydration reactions to generate 6′,7′-dihydroxybergamottin, with a few amounts of isoimperatorin produced too; both reactions followed the first-order kinetics. At pH 2.0 and 3.5, 6′,7′-EB showed a half-life of 9.71 and 119.7 min, respectively, whereas at pH 5.0 it was almost stable. This developed method achieved the automatic on-line analysis of 6′,7′-EB reaction rate, exhibiting the characteristics of both high precision and time/effort saving. The obtained reaction rate constant at pH 3.5 could be used to accurately predict the concentration of 6′,7′-EB and its products in real grapefruit juice.
LI Guijie
,
CHENG Yujiao
,
ZHANG Qunlin
,
ZHOU Qi
,
TAN Anqun
,
ZHANG Tenghui
,
WU Houjiu
,
ZHAO Xiaochun
,
RUSSELL L ROUSEFF
,
LIANG Guolu
. The effect of pH on epoxybergamottin hydration in citrus juices analyzed by online reaction-high performance liquid chromatography[J]. Food and Fermentation Industries, 2020
, 46(3)
: 242
-249
.
DOI: 10.13995/j.cnki.11-1802/ts.021807
[1] FREROT E, DECORZANT E. Quantification of total furocoumarins in citrus oils by HPLC coupled with UV, fluorescence, and mass detection[J]. Journal of Agricultural and Food Chemistry, 2004, 52(23): 6 879-6 886.
[2] PEROUTKA R, SCHULZOVA V, BOTEK P, et al. Analysis of furanocoumarins in vegetables (Apiaceae) and citrus fruits (Rutaceae)[J]. Journal of the Science of Food and Agriculture, 2010, 87(11): 2 152-2 163.
[3] DUGRAND-JUDEK A, OLRY A, HEHN A, et al. The distribution of coumarins and furanocoumarins in Citrus species closely matches Citrus phylogeny and reflects the organization of biosynthetic pathways[J]. PLoS ONE, 2015, 10(11)e0142757.
[4] WU T S, WU P L, TSANG Z J, et al. New constituents and antiplatelet aggregation and anti-HIV principles of Artemisia capillaris[J]. Bioorganic and Medicinal Chemistry, 2001, 9(1): 77-83.
[5] 敖平. 什姆干栓翅芹中具有抗免疫缺陷病毒活性的香豆素及呋喃香豆素衍生物[J]. 国外医学(中医中药分册), 2002(4): 231-232.
[6] ADAMS M, ETTL S, KUNERT O, et al. Antimycobacteria activity of geranylated furocoumarins from Tetradium daniellii[J]. Planta Medica, 2006, 72(12): 1 132-1 135.
[7] LIN H C, TSAI S H, CHEN C S, et al. Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities[J]. Biochemical Pharmacology, 2008, 75(6): 1 416-1 425.
[8] APPENDINO G, BIANCHI F, BADER A, et al. Coumarins from Opopanax chironium. New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin[J]. Journal of Natural Products, 2004, 67(4): 532-536.
[9] SRIKRISHNA D, GODUGU C, DUBEY P K. A Review on pharmacological properties of coumarins[J]. Mini-Reviews in Medicinal Chemistry, 2018, 18(2): 113-141.
[10] GIRENNAVAR B, POULOSE S M, JAYAPRAKASHA G K, et al. Furocoumarins from grapefruit juice and their effect on human CYP 3A4 and CYP 1B1 isoenzymes[J]. Bioorganic and Medicinal Chemistry, 2006, 14(8): 2 606-2 612.
[11] STRAUGHAN J L. Grapefruit-drug interactions[J]. Cardiovascular Journal of South Africa: Official Journal for Southern Africa Cardiac Society and South African Society of Cardiac Practitioners, 2007, 18(1): 39-40.
[12] DE CASTRO W V, MERTENS-TALCOTT S, RUBNER A, et al. Variation of flavonoids and furanocoumarins in grapefruit juices: A potential source of variability in grapefruit juice? drug interaction studies[J]. Journal of Agricultural and Food Chemistry, 2006, 54(1): 249-255.
[13] BAILEY D G, ARNOLD J M O, MUNOZ C, et al. Grapefruit juice-felodipine interaction: mechanism, predictability, and effect of naringin[J]. Clinical Pharmacology and Therapeutics, 1993, 53(6): 637-642.
[14] UESAWA Y, MOHRI K. Quantitative structure-activity relationship (QSAR) analysis of the inhibitory effects of furanocoumarin derivatives on cytochrome P450 3A activities[J]. Pharmazie, 2010, 65(1): 41-46.
[15] ROW E C, BROWN S A, STACHULSKI A V, et al. Design, synthesis and evaluation of furanocoumarin monomers as inhibitors of CYP3A4[J]. Organic and Biomolecular Chemistry, 2006, 4(8): 1 604-1 610.
[16] XU J, MA L L, JIANG D, et al. Content evaluation of 4 furanocoumarin monomers in various citrus germplasms[J]. Food Chemistry, 2015, 187: 75-81.
[17] CANCALON P F, BARROS S M, HAUN C, et al. Effect of maturity, processing, and storage on the furanocoumarin composition of grapefruit and grapefruit juice[J]. Journal of Food Science, 2011, 76(4): C543-C548.
[18] MANTHEY J A, BUSLIG B S. Distribution of furanocoumarins in grapefruit juice fractions[J]. Journal of Agricultural and Food Chemistry, 2005, 53(13): 5 158-5 163.
[19] LI G J, WU H J, WANG Y, et al. Determination of citrus juice coumarins, furanocoumarins and methoxylated flavones using solid phase extraction and HPLC with photodiode array and fluorescence detection[J]. Food Chemistry, 2019, 271(1): 29-38.
[20] 周婵,许家喜. 非对称环氧乙烷的区域选择性亲核开环反应[J]. 化学进展, 2011, 23(1): 165-180.
[21] 郭庆启,张娜,何娇,等. 蓝靛果汁花色苷热降解动力学的研究[J]. 食品与发酵工业, 2011, 37(9): 74-78.
[22] 尚远,卢立新,许文才. 橙汁饮料中维生素C的无氧分解动力学[J]. 食品工业科技, 2008(10): 120-122.
[23] 蒋海萍,廖丹葵,孙建华,等. 抗氧化肽HDHPVC和HEKVC的反应动力学及抗氧化能力评价方法[J]. 食品科学, 2014, 35(17): 109-113.
[24] 胡静,李巨秀. 采用牛血清白蛋白/果糖体系研究荧光性AGEs生成的动力学[J]. 食品科学, 2017, 38(1): 7-12.
[25] 卢永翎,肖留榜,夏秋琴,等. 精氨酸——还原糖体系中1,2-二羰基化合物的形成和抑制研究[J]. 食品与机械, 2018, 34(10): 1-7.
[26] 周梦舟,丁城,关亚飞,等. 原花青素抑制丙烯酰胺的动力学[J]. 食品科学, 2018, 39(3): 123-128.
[27] 常瑞,何江,罗先锟,等. 羟自由基与Neu5Gc抽氢反应的理论动力学研究[J]. 现代食品科技,2019,35(10):66-75.
[28] PELEG H, NAIM M, ZEHAVI U, et al. Pathways of 4-vinylguaiacol formation from ferulic acid in model solutions of orange juice[J]. Journal of Agricultural and Food Chemistry, 1992, 40(5): 764-767.
[29] 周琦,谈安群,易鑫,等. 基于柑橘汁多甲氧基黄酮特征成分鉴别橙汁中宽皮桔汁的方法[J]. 食品与发酵工业:,2019,45(17):227-233.
