迷迭香酸生物学作用研究进展
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摘要
迷迭香酸(RA)是一种天然存在的羟基化合物,常见于多种植物中,如迷迭香和紫苏。它是一些中草药的主要活性成分,有抗炎、抗氧化、抗抑郁的能力,并且同时还具有抗菌作用、抗病毒活性,这些属性增加了对RA及其衍生物的需求,使其广泛应用于食品、药品和化妆品领域。本文对其生产方法、药理作用的研究情况进行了综述,旨在为其后续研究提供帮助。
Rosmarinic acid(RA)is a naturally occurring hydroxylated compound commonly found in many plants,such as rosemary and Perilla frutescens.It is the main active ingredient of some Chinese herbal medicines which has anti-inflammatory,anti-oxidant,anti-depressant activities,anti-bacterial and anti-viral activities.These attributes increased the demand for RA and its derivatives making it widely used in food,medicine and cosmetics industries.This paper reviews the research methods of its production methods and pharmacological effects,and aims to provide assistance for its follow-up research.
Rosmarinic acid(RA)is a naturally occurring hydroxylated compound commonly found in many plants,such as rosemary and Perilla frutescens.It is the main active ingredient of some Chinese herbal medicines which has anti-inflammatory,anti-oxidant,anti-depressant activities,anti-bacterial and anti-viral activities.These attributes increased the demand for RA and its derivatives making it widely used in food,medicine and cosmetics industries.This paper reviews the research methods of its production methods and pharmacological effects,and aims to provide assistance for its follow-up research.
引文
[1] PETERSEN M,ABDULLAH Y,BENNER J,et al.Evolution of rosmarinic acid biosynthesis[J].Phytochemistry,2009,70(15/16):1663-1679.
[2]吴建章,郁建平,赵东亮.迷迭香酸的研究进展[J].天然产物研究与开发,2005,17(3):383-388.
[3] EICHER T,OTT M,SPEICHER A.Bryophyte constituents;7:new synthesis of(+)-Rosmarinic acid and related compounds[J].Synthesis(Mass),1996(6):755-762.
[4] BOGUCKI D E,CHARLTON J L.ChemInform abstract:a Non-Enzymatic synthesis of(S)-(-)-Rosmarinic acid and a study of a biomimetic route to(+)-Rabdosiin[J].Cheminform,2010,29(26):1783-1794.
[5]吕晓玲,周平,姚秀玲.大孔吸附树脂分离纯化迷迭香酸的制备工艺:CN200610015599.1[P].2008-03-12.
[6] KIM G D,PARK Y S,JIN Y H,et al.Production and applications of rosmarinic acid and structurally related compounds[J].Appl Microbiol Biotechnol,2015,99(5):2083-2092.
[7] ELLIS B E,TOWERS G H.Biogenesis of rosmarinic acid in Mentha[J].Biochemical Journal,1970,118:291-294.
[8]孙峋,汪靖超,李洪涛,等.迷迭香酸的抗菌机理研究[J].青岛大学学报(自然科学版),2005,18(4):41-45.
[9] SURIYARAK S,GIBIS M,SCHMIDT H,et al.Antimicrobial mechanism and activity of dodecyl rosmarinate against staphylococcus carnosus LTH1502as influenced by addition of salt and change in pH[J].J Food Prot,2014,77(3):444-452.
[10]WIDMER T L,LAURENT N.Plant extracts containing caffeic acid and rosmarinic acid inhibit zoospore germination of Phytophthora spp.pathogenic to Theobroma cacao[J].Eur J Plant Pathol,2006,115(4):377-388.
[11]郭道森,杜桂彩,李丽,等.迷迭香酸对几种植物病原真菌的抗菌活性[J].微生物学通报,2004,31(4):71-76.
[12]YAMASAKI K,NAKANO M,KAWAHATAT T.AntiHIV-1activity of herbs in Labiatae[J].Biol Pharm Bull,1998,21:829-833.
[13]KAGEYAMA S,KUROKAWA M,SHIRAKI K.Extract of prunella vulgaris spikes inhibits HIV replication at reverse transcription in vitro and can be absorbed from intestine in vivo[J].Antivir Chem Chemother,2000,11(2):157-164.
[14]DUBOIS M,BAILLY F,MBEMBA G,et al.Reaction of rosmarinic acid with nitrite ions in acidic conditions:Discovery of nitro-and dinitrorosmarinic acids as new antiHIV-1agents[J].J Med Chem,2008,51(8):2575-2579.
[15]SWARUP V,GHOSH J,GHOSH S,et al.Antiviral and anti-inflammatory effects of rosmarinic acid in an experimental murine model of Japanese encephalitis[J].Antimicrob Agents Chemother,2007,51(9):3367-3370.
[16]TSUKAMOTO Y,IKEDA S,UWAI K,et al.Rosmarinic acid is a novel inhibitor for Hepatitis B virus replication targeting viral epsilon RNA-polymerase interaction[J].PLoS One,2018,13(5):e0197664.
[17]QIAO S,LI W,TSUBOUCHI R.Rosmarinic acid inhibits the formation of reactive oxygen and nitrogen species in RAW264.7 macrophages[J].Free Radic Res,2005,39(9):995-1003.
[18]NAKAMURA Y,OHTO Y,MURAKAMI A,et al.Superoxide scavenging activity of rosmarinic acid from Perilla frutescens Britton var.acuta f.viridis[J].J Agric Food Chem,1998,46(11):4545-4550.
[19]OSAKABE N,YASUDA A M,KATO Y,et al.Rosmarinic acid,a major polyphenolic component of Perilla frutescens,reduces lipopolysaccharide(LPS)-induced liver injury in D-galactosamine(D-GalN)-sensitized mice[J].Free Radic Biol Med,2015,33(6):798-826.
[20]MOON D O,KIM M O,LEE J D,et al.Rosmarinic acid sensitizes cell death through suppression of TNF-alphainduced NF-kappaB activation and ROS Generation in human leukemia U937cells[J].Cancer Lett,2010,288(2):183-191.
[21]SCHECKEL K A,DEGNER S C,ROMAGNOLO D F.Rosmarinic acid antagonizes activator protein-1-Dependent activation of cyclooxygenase-2expression in human cancer and nonmalignant cell lines[J].J Nutr,2008,138(11):2098-2105.
[22] MILELLA M,FALCONE I,CONCIATORI F,et al.PTEN:multiple functions in human malignant tumors[J].Front Oncol,2015,5(5):24.
[23]OCANA A,VERA-BADILLO F,AL-MUBARAK M A,et al.Activation of the PI3K/mTOR/AKT pathway and survival in solid tumors:systematic review and Meta-Analysis[J].PLoS One,2014,9(4):e95219.
[24]娄诤,赵肖涯,杜丽君.迷迭香酸抑制人多发性骨髓瘤ARH-77细胞增殖的作用机制[J].中国药理学通报,2018,(8).
[25]JELIC D,MILDNER B,KOSTRUN S.Homology modeling of human Fyn kinase structure:discovery of rosmarinic acid as a new Fyn kinase inhibitor and in silico study of its possible binding modes[J].J Med Chem,2007,50(6):1090-1100.
[26]HOOKER C W,LOTT W B,HARRICH D.Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription[J].J Virol,2001,75(7):3095-3104.
[27]尤茹,马雪倩,吴炳火,等.迷迭香酸药理作用研究进展[J].四川生理科学杂志,2015,37(2):93-96.
[28]尚雁君,黄才国,蒋三好,等.迷迭香酸对黄嘌呤氧化酶的抑制作用[J].第二军医大学学报,2006,27(2):189-191.
[2]吴建章,郁建平,赵东亮.迷迭香酸的研究进展[J].天然产物研究与开发,2005,17(3):383-388.
[3] EICHER T,OTT M,SPEICHER A.Bryophyte constituents;7:new synthesis of(+)-Rosmarinic acid and related compounds[J].Synthesis(Mass),1996(6):755-762.
[4] BOGUCKI D E,CHARLTON J L.ChemInform abstract:a Non-Enzymatic synthesis of(S)-(-)-Rosmarinic acid and a study of a biomimetic route to(+)-Rabdosiin[J].Cheminform,2010,29(26):1783-1794.
[5]吕晓玲,周平,姚秀玲.大孔吸附树脂分离纯化迷迭香酸的制备工艺:CN200610015599.1[P].2008-03-12.
[6] KIM G D,PARK Y S,JIN Y H,et al.Production and applications of rosmarinic acid and structurally related compounds[J].Appl Microbiol Biotechnol,2015,99(5):2083-2092.
[7] ELLIS B E,TOWERS G H.Biogenesis of rosmarinic acid in Mentha[J].Biochemical Journal,1970,118:291-294.
[8]孙峋,汪靖超,李洪涛,等.迷迭香酸的抗菌机理研究[J].青岛大学学报(自然科学版),2005,18(4):41-45.
[9] SURIYARAK S,GIBIS M,SCHMIDT H,et al.Antimicrobial mechanism and activity of dodecyl rosmarinate against staphylococcus carnosus LTH1502as influenced by addition of salt and change in pH[J].J Food Prot,2014,77(3):444-452.
[10]WIDMER T L,LAURENT N.Plant extracts containing caffeic acid and rosmarinic acid inhibit zoospore germination of Phytophthora spp.pathogenic to Theobroma cacao[J].Eur J Plant Pathol,2006,115(4):377-388.
[11]郭道森,杜桂彩,李丽,等.迷迭香酸对几种植物病原真菌的抗菌活性[J].微生物学通报,2004,31(4):71-76.
[12]YAMASAKI K,NAKANO M,KAWAHATAT T.AntiHIV-1activity of herbs in Labiatae[J].Biol Pharm Bull,1998,21:829-833.
[13]KAGEYAMA S,KUROKAWA M,SHIRAKI K.Extract of prunella vulgaris spikes inhibits HIV replication at reverse transcription in vitro and can be absorbed from intestine in vivo[J].Antivir Chem Chemother,2000,11(2):157-164.
[14]DUBOIS M,BAILLY F,MBEMBA G,et al.Reaction of rosmarinic acid with nitrite ions in acidic conditions:Discovery of nitro-and dinitrorosmarinic acids as new antiHIV-1agents[J].J Med Chem,2008,51(8):2575-2579.
[15]SWARUP V,GHOSH J,GHOSH S,et al.Antiviral and anti-inflammatory effects of rosmarinic acid in an experimental murine model of Japanese encephalitis[J].Antimicrob Agents Chemother,2007,51(9):3367-3370.
[16]TSUKAMOTO Y,IKEDA S,UWAI K,et al.Rosmarinic acid is a novel inhibitor for Hepatitis B virus replication targeting viral epsilon RNA-polymerase interaction[J].PLoS One,2018,13(5):e0197664.
[17]QIAO S,LI W,TSUBOUCHI R.Rosmarinic acid inhibits the formation of reactive oxygen and nitrogen species in RAW264.7 macrophages[J].Free Radic Res,2005,39(9):995-1003.
[18]NAKAMURA Y,OHTO Y,MURAKAMI A,et al.Superoxide scavenging activity of rosmarinic acid from Perilla frutescens Britton var.acuta f.viridis[J].J Agric Food Chem,1998,46(11):4545-4550.
[19]OSAKABE N,YASUDA A M,KATO Y,et al.Rosmarinic acid,a major polyphenolic component of Perilla frutescens,reduces lipopolysaccharide(LPS)-induced liver injury in D-galactosamine(D-GalN)-sensitized mice[J].Free Radic Biol Med,2015,33(6):798-826.
[20]MOON D O,KIM M O,LEE J D,et al.Rosmarinic acid sensitizes cell death through suppression of TNF-alphainduced NF-kappaB activation and ROS Generation in human leukemia U937cells[J].Cancer Lett,2010,288(2):183-191.
[21]SCHECKEL K A,DEGNER S C,ROMAGNOLO D F.Rosmarinic acid antagonizes activator protein-1-Dependent activation of cyclooxygenase-2expression in human cancer and nonmalignant cell lines[J].J Nutr,2008,138(11):2098-2105.
[22] MILELLA M,FALCONE I,CONCIATORI F,et al.PTEN:multiple functions in human malignant tumors[J].Front Oncol,2015,5(5):24.
[23]OCANA A,VERA-BADILLO F,AL-MUBARAK M A,et al.Activation of the PI3K/mTOR/AKT pathway and survival in solid tumors:systematic review and Meta-Analysis[J].PLoS One,2014,9(4):e95219.
[24]娄诤,赵肖涯,杜丽君.迷迭香酸抑制人多发性骨髓瘤ARH-77细胞增殖的作用机制[J].中国药理学通报,2018,(8).
[25]JELIC D,MILDNER B,KOSTRUN S.Homology modeling of human Fyn kinase structure:discovery of rosmarinic acid as a new Fyn kinase inhibitor and in silico study of its possible binding modes[J].J Med Chem,2007,50(6):1090-1100.
[26]HOOKER C W,LOTT W B,HARRICH D.Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription[J].J Virol,2001,75(7):3095-3104.
[27]尤茹,马雪倩,吴炳火,等.迷迭香酸药理作用研究进展[J].四川生理科学杂志,2015,37(2):93-96.
[28]尚雁君,黄才国,蒋三好,等.迷迭香酸对黄嘌呤氧化酶的抑制作用[J].第二军医大学学报,2006,27(2):189-191.