油橄榄羟基酪醇的生物合成及其衍生物研究进展

doi:10.3969/j.issn.0253-2417.2015.02.024

Abstract

Abstract: Chemical syntheses of hydroxytyrosol from different materials were investigated. Its disadvantages included long route, the low yield of product, and expensive catalyst as well as toxic reactants,etc.. This paper emphatically summarized biological synthetic routes for hydroxytyrosol with oleuropein and tyrosol. Furthermore, the syntheses and biological activities of hydroxytyrosol alkyl ether, lipophilic fatty acid ester, and glucoside derivatives, and structure-activity relationship were introduced. It is important to further study the syntheses of hydroxytyrosol and derivatives, and exploit new medicine of anti-tumor, anticancer, cardiovascular and cerebrovascular diseases.

Key words: hydroxytyrosol, alkyl ether, lipophilic fatty acid ester, glucosylated derivatives, biological transformation

CLC Number:

TQ35

YUAN Jiao-jiao, YE Jian-zhong, WANG Cheng-zhang, LU Li. Advance in Biosyntheses and Biological Activities of Olive Hydroxytyrosol and Its Derivatives[J]. Chemistry and Industry of Forest Products, 2015, 35(2): 154-162.

References

[1] GRANADOS-PRINCIPAL S, QUILES J L, RAMIREZ-TORTOSA C L, et al.Hydroxytyrosol:from Laboratory investigations to future clinical trials[J].Nutrition Reviews, 2010, 68(4):191-206.
[2] ROMERO C, BRENES M.Analysis of total contents of hydroxytyrosol and tyrosol in olive oils[J].Journal of Agricultural and Food Chemistry, 2012, 60(36):9017-9022.
[3] VISIOLI F, CARUSO D, PLASMATI E, et al.Hydroxytyrosol, as a component of olive mill waste water, is dose-dependently absorbed and increases the antioxidant capacity of rat plasma[J].Free Radical Research, 2001, 34(3):301-305.
[4] BISIGNANO G, TOMAINO A, CASCIO R L, et al.On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol[J].Journal of Pharmacy and Pharmacology, 1999, 51(8):971-974.
[5] KILLEEN M J, PONTONIERE P, CREA R.Hydroxytyrosol:An examination of its potential role in cardiovascular disease, inflammation, and longevity[J].Agricultural Food Industry High Technology, 2011, 22(5):16-19.
[6] OWEN R W, GIACOSA A, HULL W E, et al.The antioxidant/anticancer potential of phenolic compounds isolated from olive oil[J].European Journal of Cancer, 2000, 36(10):1235-1247.
[7] 刘威振, 张兴, 陈新建, 等.羟基酪醇药理作用研究进展[J].广东药学院学报, 2012, 28(6):684-688. LIU Wei-zhen, ZHANG Xing, CHEN Xin-jian, et al.Research progress on pharmacological actions of hydroxytyrosol[J].Journal of Guangdong Pharmaceutical University, 2012, 28(6):684-688.
[8] FABIANI R, DE BARTOLOMEO A, ROSIGNOLI P, et al.Virgin olive oil phenols inhibit proliferation of human promyelocytic leukemia cells (HL60) by inducing apoptosis and differentiation[J].The Journal of Nutrition, 2006, 136(3):614-619.
[9] BERNINI R, CRISANTE F, MERENDINO N, et al.Synthesis of a novel ester of hydroxytyrosol and α-lipoic acid exhibiting an antiproliferative effect on human colon cancer HT-29 cells[J].European Journal of Medicinal Chemistry, 2011, 46(1):439-446.
[10] BOUALLAGUI Z, HAN J, ISODA H, et al.Hydroxytyrosol rich extract from olive leaves modulates cell cycle progression in MCF-7 human breast cancer cells[J].Food and Chemical Toxicology, 2011, 49(1):179-184.
[11] 王成章, 高彩霞, 叶建中, 等.HPLC研究油橄榄叶中橄榄苦苷的含量变化规律[J].林产化学与工业, 2008, 28(6):39-43. WANG Cheng-zhang, GAO Cai-xia, YE Jian-zhong, et al.Study on seasonal variation of oleuropein content in olive leaves by HPLC[J].Chemistry and Industry of Forest Products, 2008, 28(6):39-43.
[12] 叶建中, 王成章, 陈虹霞, 等.油橄榄叶中羟基酪醇含量及提取工艺研究[J].林产化学与工业, 2011, 31(1):63-67. YE Jian-zhong, WANG Cheng-zhang, CHEN Hong-xia, et al.Content determination and extraction technology of hydroxytyrosol from olive leaves[J].Chemistry and Industry of Forest Products, 2011, 31(1):63-67.
[13] 金元宝, 党建章, 代建国, 等.羟基酪醇分离纯化方法研究进展[J].食品科技, 2011, 36(7):174-177. JIN Yuan-bao, DANG Jian-zhang, DAI Jian-guo, et al.Progress of extraction and purification of the hydroxytyrosol[J].Food Science and Technology, 2011, 36(7):174-177.
[14] 叶建中, 王成章, 陈虹霞, 等.油橄榄叶中羟基酪醇的含量变化规律研究[J].林产化学与工业, 2011, 31(2):70-74. YE Jian-zhong, WANG Cheng-zhang, CHEN Hong-xia, et al.Variation rule of hydroxytyrosol content in olive leaves[J].Chemistry and Industry of Forest Products, 2011, 31(2):70-74.
[15] ANTONIO P, GIOVANNI S, NICOLA C, et al.Chemical-catalytic method for the peracylation of oleuropein and its products of hydrolysis:EP, WO2008136037[P].2008-11-13.
[16] CUOMO J, RABOVSKIY A B.Antioxidant compositions extracted from a wastewater from olive oil production:US, US6361803[P].2002-03-26.
[17] VILLANOVA L, FASIELLO G, MERENDINO A, et al.Process for the recovery of tyrosol and hydroxytyrosol from oil mill wastewaters and catalytic oxidation method in order to convert tyrosol in hydroxytyrosol:EP, 1623960[P].2009-12-23.
[18] FELIZÓN B, FERNÁNDEZ-BOLAÑOS J, HEREDIA A, et al.Steam-explosion pretreatment of olive cake[J].Journal of the American Oil Chemists' Society, 2000, 77(1):15-22.
[19] LEONARDIS A D, ARETINI A, ALFANO G, et al.Isolation of a hydroxytyrosol-rich extract from olive leaves(Olea europaea L.) and evaluation of its antioxidant properties and bioactivity[J].European Food Research and Technology, 2008, 226(4):653-659.
[20] RIGANE G, BOUAZIZ M, BACCAR N, et al.Recovery of hydroxytyrosol rich extract from two-phase chemlali olive pomace by chemical treatment[J].Journal of Food Science, 2012, 77(10):1077-1083.
[21] LUCIA M D, PANZELLA L, PEZZELLA A, et al.Oxidative chemistry of the natural antioxidant hydroxytyrosol:Hydrogen peroxide-dependent hydroxylation and hydroxyquinone/o-quinone coupling pathways[J].Tetrahedron, 2006, 62(6):1273-1278.
[22] BOVICELLI P, ANTONIOLETTI R, MANCINI S, et al.Expedient synthesis of hydroxytyrosol and its esters[J].Synthetic Communications, 2007, 37(23):4245-4252.
[23] AZABOU S, NAJJAR W, GHORBEL A, et al.Mild photochemical synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol[J].Journal of Agricultural and Food Chemistry, 2007, 55(12):4877-4882.
[24] BARALDI P G, SIMONI D, MANFREDINI S, et al.Preparation of 3, 4-dihydroxy-1-benzeneethanol:A reinvestigation[J].Liebigs Annalen der Chemie, 1983, 1983(4):684-686.
[25] BAI Chen, YAN Xiao-jun, TAKENAKA M, et al.Determination of synthetic hydroxytyrosol in rat plasma by GC-MS[J].Journal of Agricultural and Food Chemistry, 1998, 46(10):3998-4001.
[26] TUCK K L, TAN Hai-wei, HAYBALL P J.Synthesis of tritium-labeled hydroxytyrosol, a phenolic compound found in olive oil[J].Journal of Agricultural and Food Chemistry, 2000, 48(9):4087-4090.
[27] 延永, 郭媛, 彭梦姣, 等.羟基酪醇的合成[J].精细化工, 2012, 29(10):985-988. YAN Yong, GUO Yuan, PENG Meng-jiao, et al.Synthesis of hydroxytyrosol[J].Fine Chemicals, 2012, 29(10):985-988.
[28] 许超, 高俊超, 张坚, 等.羟基酪醇合成工艺研究[J].精细化工, 2012, 27(12):1209-1212. XU Chao, GAO Jun-chao, ZHANG Jian, et al.Process research of hydroxytyrosol synthesis[J].Fine Chemicals, 2012, 27(12):1209-1212.
[29] ZHANG Zhao-li, CHEN Jing-lei, XU Qiong-ming, et al.Effcient synthesis of hydroxytyrosol from 3, 4-dihydroxybenzaldehyde[J].Synthetic Communications, 2012, 42(6):794-798.
[30] BRIANTE R, CARA F L, TONZIELLO M P, et al.Antioxidant activity of the main bioactive derivatives from oleuropein hydrolysis by hyperthermophilic β-glycosidase[J].Journal of Agricultural and Food Chemistry, 2001, 49(7):3198-3203.
[31] BRIANTE R, PATUMI M, FEBBRAIO F, et al.Production of highly purified hydroxytyrosol from Olea europaea leaf extract biotransformed by hyperthermophilic β-glycosidase[J].Journal of Biotechnology, 2004, 111(1):67-77.
[32] ESPIN J C, SOLAR-RIVAS C, CANTOS E, et al.Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst[J].Journal of Agricultural and Food Chemistry, 2001, 49(3):1187-1193.
[33] SANTOS M M, PICCIRILLO C, CASTRO P M L, et al.Bioconversion of oleuropein to hydroxytyrosol by lactic acid bacteria[J].World Journal of Microbiology & Biotechnology, 2012, 28(6):2435-2440.
[34] ALLOUCHE N, DAMAK M, ELLOUZ R, et al.Use of Whole cells of Pseudomonas aeruginosa for synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol[J].Applied and Environmental Microbiology, 2004, 70(4):2105-2109.
[35] ALLOUCHE N, SAYADI S.Synthesis of hydroxytyrosol, 2-hydroxyphenylacetic acid, and 3-hydroxyphenylacetic acid by differential conversion of tyrosol isomers using Serratia marcescens strain[J].Journal of Agricultural and Food Chemistry, 2005, 53(16):6525-6530.
[36] BOUALLAGUI Z, SAYADI S.Production of high hydroxytyrosol yields via tyrosol conversion by Pseudomonas aeruginosa immobilized resting cells[J].Journal of Agricultural and Food Chemistry, 2006, 54(26):9906-9911.
[37] BROOKS S J, DOYLE E M, O'CONNOR K E.Tyrosol to hydroxytyrosol biotransformation by immobilized cell extracts of Pseudomonas putida F6[J].Enzyme and Microbial Technology, 2006, 39(2):191-196.
[38] SATOH Y, TAJIMA K, MUNEKATA M, et al.Engineering of L-tyrosine oxidation in Escherichia coli and microbial production of hydroxytyrosol[J].Metabolic Engineering, 2012, 14(6):603-610.
[39] ORENES-PIÑERO E, GARCÍA-CARMONA F, SÁNCHEZ-FERRER Á.A new process for obtaining hydroxytyrosol using transformed Escherichia coli whole cells with phenol hydroxylase gene from Geobacillus thermoglucosidasius[J].Food Chemistry, 2013, 139 (1/2/3/4):377-383.
[40] BROUK M, FISHMAN A.Protein engineering of toluene monooxygenases for synthesis of hydroxytyrosol[J].Food Chemistry, 2009, 116(1):114-121.
[41] HALAOULI S, ASTHER M, KRUUS K, et al.Characterization of a new tyrosinase from Pycnoporus species with high potential for food technological applications[J].Journal of Applied Microbiology, 2005, 98(2):332-343.
[42] BOUZID O, NAVARRO D, ROCHE M, et al.Fungal enzymes as a powerful tool to release simple phenolic compounds from olive oil by-product[J].Process Biochemistry, 2005, 40(5):1855-1862.
[43] KHOUFI S, HAMZA M, SAYADI S.Enzymatic hydrolysis of olive wastewater for hydroxytyrosol enrichment[J].Bioresource Technology, 2011, 102(19):9050-9058.
[44] PEREIRA-CARO G, MADRONA A, BRAVO L, et al.Antioxidant activity evaluation of alkyl hydroxytyrosyl ethers, a new class of hydroxytyrosol derivatives[J].Food Chemistry, 2009, 115(1):86-91.
[45] MADRONA A, PEREIRA-CARO G, MATEOS R, et al.Synthesis of hydroxytyrosyl alkyl ethers from olive oil waste waters[J].Molecules, 2009, 14(5):1762-1772.
[46] PEREIRA-CARO G, SARRIA B, MADRONA A, et al.Alkyl hydroxytyrosyl ethers show protective effects against oxidative stress in HepG2 cells[J].Journal of Agricultural and Food Chemistry, 2011, 59(11):5964-5976.
[47] PEREIRA-CARO G, MATEOS R, TRAKA M H, et al.Hydroxytyrosyl ethyl ether exhibits stronger intestinal anticarcinogenic potency and effects on transcript profiles compared to hydroxytyrosol[J].Food Chemistry, 2013, 138(2/3):1172-1182.
[48] MATEOS R, PEREIRA-CARO G, BACON J R, et al.Anticancer activity of olive oil hydroxytyrosyl acetate in human adenocarcinoma Caco-2 cells[J].Journal of Agricultural and Food Chemistry, 2013, 61(13):3264-3269.
[49] PROCOPIO A, CELIA C, NARDI M, et al.Lipophilic hydroxytyrosol esters:Fatty acid conjugates for potential topical administration[J].Journal of Natural Products, 2011, 74(11):2377-2381.
[50] BOUALLAGUI Z, BOUAZIZ M, LASSOUED S, et al.Hydroxytyrosol acyl esters:Biosynthesis and activities[J].Applied Biochemistry and Biotechnology, 2011, 163(5):592-599.
[51] BERNINI R, MINCIONE E, BARONTINI M, et al.Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol[J].Journal of Agricultural and Food Chemistry, 2008, 56(19):8897-8904.
[52] BERNINI R, CRISANTE F, BARONTINI M, et al.Synthesis and structure/antioxidant activity relationship of novel catecholic antioxidant structural analogues to hydroxytyrosol and its lipophilic esters[J].Journal of Agricultural and Food Chemistry, 2012, 60(30):7408-7416.
[53] REZAEI-SADABADY R, ZARGHAMI N, BARZEGAR A, et al.Studies of the relationship between structure and antioxidant activity in interesting systems, including tyrosol, hydroxytyrosol derivatives indicated by quantum chemical calculations[J].Soft, 2013, 2(3):13-18.
[54] TRINCONE A, PAGNOTTA E, TRAMICE A.Enzymatic routes for the production of mono- and di-glucosylated derivatives of hydroxytyrosol[J].Bioresource Technology, 2012, 115:79-83.

Advance in Biosyntheses and Biological Activities of Olive Hydroxytyrosol and Its Derivatives

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[3]	YE Jian-zhong;WANG Cheng-zhang;CHEN Hong-xia;ZHOU Hao. Variation Rule of Hydroxytyrosol Content in Olive Leaves [J]. , 2011, 31(2): 69-74.
[4]	YE Jian-zhong;WANG Cheng-zhang;CHEN Hong-xia;DONG Yan-he. Content Determination and Extraction Technology of Hydroxytyrosol from Olive Leaves [J]. , 2011, 31(1): 63-67.