手性萜类香料化合物制备的研究进展Research Progress on the Preparation of Chiral Terpene Spice Compounds
毛悦,汪薇,白卫东,王靖宇,李湘銮,姜浩,赵文红
摘要(Abstract):
手性萜类香料化合物具有柠檬、柏油、留兰香等香气,广泛应用于食品、日用品行业中。由于手性萜类香料对映体具有不同的香气特征,加上消费者对高品质天然香料的青睐,手性萜类香料化合物的生物制备法备受关注。文章介绍了柠檬烯、乙酸香茅酯、α-松油醇、香芹酮等萜类香料化合物的制备方法,分析了手性萜类香料生物法制备中面临的问题,旨在为更经济高效的生物法转化手性萜类香料提供借鉴。
关键词(KeyWords): 手性;萜类香料化合物;制备方法
基金项目(Foundation): 广东省重点研发项目(2022B020205003);; 广东省岭南特色食品科学与技术重点实验室(2021B1212040013);; 广州市科技计划项目(202103000062)
作者(Author): 毛悦,汪薇,白卫东,王靖宇,李湘銮,姜浩,赵文红
参考文献(References):
- [1]刘楠.徐闻普哥滨珊瑚共附生真菌的活性及其代谢产物的研究[D].湛江:广东海洋大学,2014.
- [2]TAOFIQ O,MARTINS A,BARREIRO M F,et al.Anti-inflammatory potential of mushroom extracts and isolated metabolites[J].Trends in Food Science & Technology,2016,50:193-210.
- [3]BAUNACH M,FRANKE J,HERTWECK C.Cheminform abstract:terpenoid biosynthesis off the beaten track:unconventional cyclases and their impact on biomimetic synthesis[J].Angewandte Chemie,2015,46(18):18288.
- [4]李兆坤,王凤寰,陈彬,等.大型真菌萜类化合物活性研究进展[J].天然产物研究与开发,2017,29(2):357-369.
- [5]樊超,谢建华,周其林.手性香料的不对称催化合成研究进展[J].应用技术学报,2018,18(3):189-219.
- [6]张媛媛,李涛.微生物法生产香料化合物的研究[J].中国调味品,2018,43(6):180-182.
- [7]王有娣,姚小丽,肖青林,等.迷迭香精油和马郁兰精油化学成分及抗氧化活性研究[J].中国调味品,2021,46(1):135-141.
- [8]王莹,曾祥辉,邓慧,等.迷迭香脂溶性抗氧化剂活性及抑制食用植物油脂氧化作用研究[J].中国调味品,2022,47(8):80-84.
- [7]庄以彬,吴凤礼,殷华,等.芳香族香料化合物生物合成研究进展[J].生物工程学报,2021,37(6):1998-2009.
- [8]张璐璐,范刚,何进,等.柠檬烯微生物转化及其相关酶的研究进展[J].食品工业科技,2019,40(12):317-325,330.
- [10]蔡庭秀,乔杨波,吴森.“小油料”精油抑菌活性研究及其在食品保藏中的应用[J].中国调味品,2021,46(8):197-200.
- [11]胡静,徐若夷,邓维钧.食用精油提取技术研究及应用进展[J].中国调味品,2022,47(9):209-213,220.
- [12]崔丽佼,于有伟,张小敏,等.离子液体辅助水蒸气蒸馏法提取柠檬精油的研究[J].中国调味品,2021,46(3):150-153.
- [13]NEJDET G.Protective effect of D-limonene derived from orange peel essential oil against Yersinia ruckeri in rainbow trout[J].Aquaculture Reports,2020,18:100417.
- [14]JOKI S,MOLNAR M,CIKO A M,et al.Separation of selected bioactive compounds from orange peel using the sequence of supercritical CO2 extraction and ultrasound solvent extraction:optimization of limonene and hesperidin content[J].Separation Science and Technology,2020,55(15):2799-2811.
- [15]JAVAD S,SEYEDEH H,MAJID S,et al.Phytochemical compositions and biological activities of essential oil from Xanthium strumarium L.[J].Molecules,2015,20(4):7034-7047.
- [16]MANN A P,VERMA A,SETHI G,et al.Overexpression of tissue transglutaminase leads to constitutive activation of nuclear factor-kappaB in cancer cells:delineation of a novel pathway[J].Cancer Research,2006,66(17):8788-8795.
- [17]冯堃,秦昭,王文蜀,等.5种柚皮精油成分及油脂抗氧化和抑菌活性[J].食品科技,2018,43(11):255-261.
- [18]张芳,姜媛媛,杨洋,等.柚提取物含量测定及其抗氧化、抑菌活性研究[J].食品工业科技,2015,36(3):65-69,73.
- [19]JONGEDIJK E,CANKAR K,RANZIJN J,et al.Capturing of the monoterpene olefin limonene produced in Saccharomyces cerevisiae[J].Yeast,2015,32(1):159-171.
- [20]丁洁,沙芮,王爱霞,等.柑橘皮挥发油提取及HPLC测定柑橘皮挥发油中的柠檬烯含量[J].湖北农业科学,2017,56(17):3326-3330.
- [21]赵优萍,张沙沙,张婷,等.不同提取方法对牡丹籽油品质与抗氧化性的影响[J].食品工业科技,2019,40(1):11-16,22.
- [22]王芳,岳朝敏,ANDREEA D,等.结合 GC-MS 的分子蒸馏富集柚皮精油抗氧化成分的研究[J].中国粮油学报,2018,33(7):65-71.
- [23]DEL VALLE M,CALDERON J,NUNEZ D,et al.Pressure drop may negatively impact supercritical CO2 extraction of citrus peel essential oils in an industrial-size extraction vessel[J].Journal of Supercritical Fluids,2019,144:108-121.
- [24]马云建.酶级联催化柠檬烯环氧化与脂肪酸脱羧的研究[D].广州:华南理工大学,2019:50-68.
- [25]CAO X,LYU Y B,CHEN J,et al.Metabolic engineering of oleaginous yeast Yarrowia lipolytica for limonene overproduction[J].Biotechnology for Biofuels,2016,9(1):214.
- [26]吴计划.工程大肠杆菌合成柠檬烯[D].天津:天津大学,2019.
- [27]DHAKE K P,DESHMUKH K M,PATIL Y P,et al.Improved activity and stability of Rhizopus oryzae lipase via immobilization for citronellol ester synthesis in supercritical carbon dioxide[J].Journal of Biotechnology,2011,156(1):46-51.
- [28]MELO L,PASTOREASTORE G M,MACEDO G A.Optimized synthesis of citronelly flavour esters using free and immboilized lipase from Phizopus sp.[J].Process Biochemistay,2005,40(10):3181-3185.
- [29]江云兵,熊兴泉.乙酸香茅酯的绿色合成与结构表征[J].华侨大学学报(自然科学版),2014,35(1):47-51.
- [30]单天宇,王栋,徐岩,等.华根霉菌丝体结合脂肪酶催化酯合成动力学拆分2-辛醇[J].催化学报,2008(4):403-408.
- [31]MACEDO G A,LOZANO M,PASTORE G M.Enzymatic synthesis of short chain citronellyl esters by a new lipase from Rhizopus sp.[J].Electronic Journal of Biotechnology,2003,6(1):3-4.
- [32]XIONG J,HUANG Y J.Lipase-catalyzed transesterification synthesis of geranyl acetate in organic solvents and its kinetics[J].Food Science and Technology Research,2014,20(2):207-216.
- [33]王楠,王栋,徐岩,等.华根霉脂肪酶催化合成乙酸香茅酯的研究[J].食品工业科技,2010,31(2):307-310.
- [34]张蒙,丛方地,任德忠,等.静置的固定化荧光假单胞菌脂肪酶(PFL)生物反应器中催化合成乙酸香茅酯[J].生物加工过程,2020,18(5):572-576.
- [35]BHATIA S P,MCGINTY D,FOXENBERG R J,et al.Fragrance material review on terpineol[J].Food & Chemical Toxicology,2008,46(11):275-279.
- [36]JUNIOR M,SILVA T,FRANCHI G C,et al.Antioxidant potential of aroma compounds obtained by limonene biotransformation of orange essential oil[J].Food Chemistry,2009,116(1):8-12.
- [37]RA J M,SIK J W,TANG H C.Health promoting properties of natural flavor substances[J].Food Science & Biotechnology,2006,15(3):329-338.
- [38]尹礼国,凌跃,杜永华,等.宜宾油樟营养器官精油主成分分析[J].江苏农业科学,2014(11):348-350,355.
- [39]曹松,安兰芝,卢祥,等.D型大孔磺酸树脂催化松节油水合一步合成松油醇[J].离子交换与吸附,2015,31(5):455-463.
- [40]邹志平,孟中磊,刘六军,等.二步法松油醇生产工艺的问题与改进[J].广西林业科学,2020,49(3):458-461.
- [41]TAI Y N,XU M,REN J N,et al.Optimisation of α-terpineol production by limonene biotransformation using Penicillium digitatum DSM 62840[J].Journal of the Science of Food and Agriculture,2016,96:954-961.
- [42]ROTTAVA I,TONIAZZO G,CORTINA P F,et al.Screening of microorganisms for bioconversion of (-) β-pinene and R-(+)-limonene to α-terpineol[J].LWT-Food Science and Technology,2010,43:1128-1131.
- [43]BICAS J L,FONTANILLE P,PASTORE G M,et al.A bioprocess for the production of high concentrations of R-(+)-α-terpineol from R-(+)-limonene[J].Process Biochemistry,2010,45:481-486.
- [44]廉长盛,付冬梅,张俊鹏,等.酒花内生菌Pseudomonas oryzihabitans F0-1转化柠檬烯生成α-萜品醇的研究[J].保鲜与加工,2021,21(12):38-45.
- [45]黄金凤,王鑫,梁玉娟,等.油樟内生细菌分离及α-松油醇高产菌株的筛选与诱变[J].食品与发酵工业,2020,46(1):75-81.
- [46]何坚,孙宝国.香料化学与工艺学[M].北京:化学工业出版社,1995:77-78.
- [47]秦斌,郭继阳,张瑞,等.香芹醇与二氢香芹醇的立体多向性生物催化合成[C]//第十二届中国酶工程学术研讨会论文摘要集,2019:126.
- [48]黄庭刚.留兰香油的精制及其香芹酮含量的测定[J].河南化工,1995(11):20-21.
- [49]陈连官.留兰香精镏精油的加工工艺与设备[J].香料香精化妆品,1987(3):60-61.
- [50]罗运华,刘以红.超临界CO2从留兰香油中萃取香芹酮[J].精细化工,2004(2):119-120,128.
- [51]LINDER S M,GREENSPAN F P.Reactions of limonene monoxide.The synthesis of carvone[J].Journal of Organic Chemistry,2002,22(8):243-251.
- [52]谢海英,徐丽红,应登宇,等.一种香芹酮的合成方法:中国,201010232407.9[P].2010-11-24.
- [53]马晨,刘兴利,赵志刚,等.香芹酮香料合成方法的改进[J].西南民族大学学报(自然科学版),2003(3):308-309,340.
- [54]姜志洁,来争争,许清清,等.电化学催化制备香芹酮[J].山东化工,2022,51(3):22-24.
- [55]LI J J,LI Z Q,ZI G L,et al.Synthesis,characterizations and catalytic allylic oxidation of limonene to carvone of cobalt doped mesoporous silica templated by reed leaves[J].Catalysis Communications,2015,59:233-237.
- [56]MOLINA G,PINHEIRO D M,PIMENTEL M R,et al.Monoterpene bioconversion for the production of aroma compounds by fungi isolated from Brazilian fruits[J].Food Science and Biotechnology,2013,22:999-1006.
- [57]BIER M,MEDEIROS A,SOCCOL C R.Biotransformation of limonene by an endophytic fungus using synthetic and orange residue-based media[J].Fungal Biology,2016,121(2):137-144.
- [58]TRYTEK M,FIEDUREK J,SKOWRONEK M.Biotransformation of (R)-(+)-limonene by the psychrotrophic fungus Mortierella minutissima in H2O2-oxygenated culture[J].Food Technology and Biotechnology,2009,47:131-136.
- [59]ERDTMAN H,HIROSE Y.The chemistry of the natural order cupressales:the structure of nootkatone[J].Acta Chemica Scandinavica,1962,16:1311-1314.
- [60]FRAATZ M A,RIEMER S J L,STOBER R,et al.A novel oxygenase from Pleurotus sapidus transforms valencene to nootkatone[J].Journal of Molecular Catalysis B:Enzymatic,2009,61(3):202-207.
- [61]YAMAGUCHI T.Antibacterial properties of nootkatone against gram-positive bacteria[J].Natural Product Communications,2019,14(6):1-5.
- [62]DANTAS L B R,SILVA A L M,JUNIOR C P S,et al.Nootkatone inhibits acute and chronic inflammatory responses in mice[J].Molecules,2020,25(9):2181.
- [63]BEHLE R W,FLOR-WEILER L B,ANUJA B,et al.A formulation to encapsulate nootkatone for tick control[J].Journal of Medical Entomology,2011,48(6):1120-1127.
- [64]樊猛,谢建春,孙宝国.同时蒸馏萃取制备富含圆柚酮的柚皮油研究[J].食品科学,2006(12):490-492.
- [65]PALMERíN-CARREO D M,RUTIAGA-QUIONES O M,VERDE-CALVO J R,et al.Biconversion of (+)-nootkatone by Botryodiplodia theobromae using a membrane aerated biofilm reactor[J].Revista Mexicana de Ingeniería Química,2014,13(3):757-764.
- [66]SALVADOR J,CLARK J H.The allylic oxidation of unsaturated steroids by tert-butyl hydroperoxide using homogeneous and heterogeneous cobalt acetate[J].Chemical Communications,2001(1):33-34.
- [67]DRAWERT F,BERGER R G,GODELMANN R.Regioselective biotransformation of valencene in cell suspension cultures of Citrus sp.[J].Plant Cell Reports,1984,3(1):37-40.
- [68]RíO A D,ORTUO A,PUIG D G,et al.Accumulation of the sesquiterpenes nootkatone and valencene by callus cultures of Citrus paradisi,Citrus limonia and Citrus aurantium[J].Plant Cell Reports,1991,10(8):410-413.
- [69]SOWDEN R J,YASMIN S,REES N H,et al.Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3[J].Organic & Biomolecular Chemistry,2005,3(1):57.
- [70]KASPERA R,KRINGS U,NANZAD T,et al.Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum[J].Applied Microbiology and Biotechnology,2005,67(4):477-483.
- [71]MAI F,HASHIMOTO T,NOMA Y,et al.Highly efficient production of nootkatone,the grapefruit aroma from valencene,by biotransformation[J].Chemical & Pharmaceutical Bulletin,2010,37(17):17185.
- [72]RAATZ M A,RIEMER S,ST?BER R,et al.A novel oxygenase from Pleurotus sapidus transforms valencene to nootkatone[J].Journal of Molecular Catalysis B:Enzymatic,2009,61(3-4):202-207.