1.上海中医药大学中药学院(上海 201203)
2.上海上药杏灵科技药业股份有限公司(上海 201703)
李玲,女,在读硕士生,主要从事中药创新及其产业化发展研究
高崎,教授,硕士生导师;E-mail:gaoqi@ xingling.com.cn
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李玲,江美芳,王丹丹等.银杏叶双黄酮化学成分及药理学研究进展[J].上海中医药大学学报,2022,36(02):101-108.
LI Ling,JIANG Meifang,WANG Dandan,et al.Research progress of chemical components and pharmacology of biflavones from Ginkgo Folium[J].Academic Journal of Shanghai University of Traditional Chinese Medicine,2022,36(02):101-108.
李玲,江美芳,王丹丹等.银杏叶双黄酮化学成分及药理学研究进展[J].上海中医药大学学报,2022,36(02):101-108. DOI: 10.16306/j.1008-861x.2022.02.016.
LI Ling,JIANG Meifang,WANG Dandan,et al.Research progress of chemical components and pharmacology of biflavones from Ginkgo Folium[J].Academic Journal of Shanghai University of Traditional Chinese Medicine,2022,36(02):101-108. DOI: 10.16306/j.1008-861x.2022.02.016.
银杏树是古老的稀有树种,其叶、果、花等已广泛用于临床治疗各种疾病。双黄酮作为黄酮的亚类,是银杏叶的主要药效成分之一,在银杏叶中含量丰富且种类较多,是一类具有抗炎、抗氧化、神经保护和心血管保护等多种生物活性的天然多酚类化合物,目前国内外的相关研究已取得一定进展。通过综述银杏叶中双黄酮的化学成分、药效学与药动学内容,以期为银杏叶双黄酮的药效物质基础及活性成分的开发和利用提供科学依据。
Ginkgo biloba L. is an ancient and rare tree specie, and its leaves, fruits and flowers have been widely used in clinical treatment of various diseases. Biflavones, as a subclass of flavonoids, are one of the main medicinal components of Ginkgo Folium, which are abundant in Ginkgo Folium with diverse types. Biflavones are a class of natural polyphenolic compounds with various biological activities such as anti-inflammatory, antioxidant, neuroprotective and cardiovascular protective activities. At present, some progress has been made in relevant studies at home and abroad. The chemical constituents, pharmacodynamics and pharmacokinetics were reviewed in order to provide scientific basis for the pharmacodynamic material basis and the development and utilization of active ingredients of biflavones in Ginkgo Folium.
银杏叶双黄酮化学成分药效学药动学综述
Ginkgo Foliumbiflavoneschemical componentspharmacodynamicspharmacokineticsreview
张中朋,刘秀芬. 银杏叶提取物发展概述[J]. 中药研究与信息,2005, 7(2): 38-40.
涂清波,孙云,许婷,等. 银杏双黄酮药理作用的研究进展[J]. 山东医药,2018, 58(19): 112-114.
JIA X,CHEN J,LIN H,et al.Disposition of flavonoids via enteric recycling:enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates[J].J Pharmacol Exp Ther,2004,310(3):1103-1113.
张尊听,高润莉,庄素凯.双黄酮的合成及其与DNA的作用[J].药学学报,2009, 44(8): 873-878.
SAGRERA G, BERTUCCI A,VAZQUEZ A, et al.Synthesis and antifungal activities of natural and synthetic biflavonoids[J].Bioorg Med Chem, 2011, 19(10): 3060-3073.
JOYEUX M, LOBSTEIN A, ANTON R,et al.Comparative antilipoperoxidant,antinecrotic and scavenging properties of terpenes and biflavones from Ginkgo and some flavonoids[J].Planta Med, 1995, 61(2): 126-129.
QIAO Y, LIU X, LI X, et al.Biflavonoids from Juniperus oblonga inhibit organic anion transporter 3[J].Biochem Biophys Res Commun, 2019, 509(4): 931-936.
LI X,OUYANG X, CAI R, et al.3',8 ″-Dimerization Enhances the Antioxidant Capacity of Flavonoids:Evidence from Acacetin and Isoginkgetin[J]. Molecules, 2019, 24(11): 2039.
THAPA A,WOO E,CHI E,et al.Biflavonoids are superior to monoflavonoids in inhibiting amyloid-β toxicity and fibrillogenesis via accumulation of nontoxic oligomer-like structures[J].Biochemistry, 2011, 50(13): 2445-2455.
MORIMOTO M,TANIMOTO K, NAKANO S,et al.Insect antifeedant activity of flavones and chromones against Spodoptera litura[J]. J Agric Food Chem, 2003, 51(2): 389-393.
杨慧萍,高睿.银杏药用成分及药理作用研究进展[J].动物医学进展,2017, 38(8): 96-99.
薛颖,袁金伟,屈凌波.双黄酮的合成与反应机理[C]//.中国化学会,中国科学院长春应用化学研究所.中国化学会第十二届全国应用化学年会论文集.郑州:中国化学会,中国科学院长春应用化学研究所,2011: 186-187.
李冰,胡高升,胡玲玲,等.银杏叶中双黄酮成分的提取与测定[J].中草药,2014, 45(17): 2552-2555.
马小芳,杨世龙,唐颖,等.银杏双黄酮类化合物研究进展[J].山东化工,2018, 47(23): 72-74,76.
齐之尧,李家玉.银杏叶的双黄酮[J].世界林业研究,2000, 13(4): 56.
GONTIJO V,DOS SANTOS M,VIEGAS C.Biological and Chemical Aspects of Natural Biflavonoids from Plants:A Brief Review[J]. Mini Rev Med Chem, 2017, 17(10): 834-862.
简悦.银杏叶渣中双黄酮成分提取分离工艺研究[D].北京:北京林业大学,2019.
靳冉,郗砚彬.银杏叶中的双黄酮苷[J].国际中医中药杂志,2006, 28(3): 172.
李敏.银杏花的化学成分及生物活性研究[D].北京:军事科学院,2019.
郁丹红,姜玮,姚鑫,等.基于UPLC-TQ-MS考察不同树龄银杏叶双黄酮含量变化规律[J].中国实验方剂学杂志,2019, 25(18): 145-149.
罗珂,张佳丽,雷家珩,等.银杏双黄酮高效液相色谱定量分析方法研究[J].化学试剂,2020, 42(1): 58-61.
徐江,沈亮,汪耀,等.基于GMPGIS银杏全球生态适宜产区分析[J].世界中医药,2017, 12(5): 969-973.
杜少严,尹硕,王意浓,等.银杏叶的药用与保健价值及其应用[J].中国食物与营养,2020, 26(6): 59-62.
吕金丽,杨彪,李孟璇,等.高效液相法同时测定银杏叶中11种成分的含量[J].中国中药杂志,2017, 42(5): 931-935.
池静端,何秀峰,刘爱茹.HPLC法测定银杏叶中6种黄酮成分的含量[J].药学学报,1997, 32(8): 625-628.
陈再兴,朱旭,王琳,等.不同季节银杏叶中总黄酮、总黄酮醇苷及萜类内酯的含量变化[J].中国医院药学杂志,2010, 30(12): 1067-1069.
杜安全,王先荣,周正华,等.不同生长季节及生长年限银杏叶总黄酮甙含量的相关性研究[J].天然产物研究与开发,2000, 12(2): 49-51.
钱大玮,鞠建明,朱玲英,等.不同树龄银杏叶在不同季节中总黄酮和总内酯的含量变化[J].中草药,2002, 33(11): 1025-1027.
仲英,唐文照,丁杏苞,等.不同树龄的银杏叶在不同生长季节中银杏总黄酮和总内酯的含量变化[J].中草药,1999, 30(12): 909-910.
LOBSTEIN A,RIETSCH-JAKO L,HAAG-BERRURIER M,et al.Seasonal Variations of the Flavonoid Content from Ginkgo biloba Leaves[J]. Planta Med, 1991, 57(5): 430-433.
姚鑫.不同来源银杏叶资源化学研究[D].南京:南京中医药大学,2013.
王霞霞,薛瑞婷,郝旺林.季节和光照对银杏叶双黄酮含量的影响[J].中国园艺文摘,2017, 33(12): 39-49.
管汉亮,钱大玮,段金廒,等.银杏叶干燥方法的优化及其机制探讨[J].中国中药杂志,2013, 38(13): 2140-2146.
陶铸.银杏中抗气道炎症活性成分及其作用机制研究[D].武汉:华中科技大学,2019.
郭丽,路青瑜,张启云,等.银杏双黄酮对高糖致微血管内皮细胞炎症反应的保护作用及机制研究[J].中国药理学通报,2020, 36(10): 1463-1469.
SON J,SON M,LEE E,et al.Ginkgetin,a Biflavone from Ginko biloba leaves,inhibits cyclooxygenases-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells[J]. Biol Pharm Bull, 2005, 28(12): 2181-2184.
严双凤,徐志波.穗花杉双黄酮对脂多糖致大鼠急性肺损伤的保护作用及机制研究[J].浙江中西医结合杂志,2020, 30(7): 530-534, 609.
王聪.7-去甲基银杏双黄酮对体外培养的人皮脂腺细胞胰岛素样生长因子1诱导皮脂生成的抑制作用[D].长春:吉林大学,2019.
KIM S.Effect of biflavones of Ginkgo biloba against UVB-induced cytotoxicity in vitro[J]. J Dermatol, 2001, 28(4): 193-199.
蒋永梅.超声辅助离子液体提取卷柏和银杏叶中双黄酮及其抗氧化活性研究[D].遵义:遵义医科大学,2020.
王力.穗花双黄酮对DNA氧化损伤的体外保护作用及其机理研究[D].广州:广州中医药大学,2013.
张佳丽,李玲,雷家珩,等.银杏叶单组分双黄酮分离制备及抗氧化活性研究[J].天然产物研究与开发,2019,31(6):952-956.
刘水.穗花杉双黄酮对产气荚膜梭菌坏死性肠炎及气性坏疽的治疗作用机制[D].长春:吉林大学,2020.
LI F,SONG X,SU G,et al.Amentoflavone Inhibits HSV-1 and ACV-Resistant Strain Infection by Suppressing Viral Early Infection[J]. Viruses, 2019, 11(5): 466.
MIKI K,NAGAI T,SUZUKI K,et al.Anti-influenza virus activity of biflavonoids[J].Bioorg Med Chem Lett, 2007, 17(3): 772-775.
WENIGER B,VONTHRON-SéNéCHEAU C,KAISER M,et al.Comparative antiplasmodial,leishmanicidal and antitrypanosomal activities of several biflavonoids[J]. Phytomedicine, 2006, 13(3): 176-180.
缪刘萍,王鑫杰,周海凤,等.双黄酮类化合物药理作用研究[J].世界临床药物,2012, 33(6): 369-374.
ADNAN M,RASUL A,HUSSAIN G,et al.Ginkgetin:A natural biflavone with versatile pharmacological activities[J].Food Chem Toxicol, 2020, 145: 111642.
秦肖菲.银杏双黄酮Ginkgetin对胃癌细胞糖代谢、生物学行为的影响及其机制研究[D].新乡:新乡医学院,2020.
张金丽,秦胜男,王鹏珍,等.穗花杉双黄酮通过促进E-cadherin/β-catenin复合体表达抑制卵巢癌细胞迁移[J].肿瘤药学,2021, 11(2): 165-169.
赵学梅,张宏莲,孔寰宇,等.金松双黄酮联合紫杉醇对肺癌A549细胞生长及凋亡的影响[J].现代生物医学进展,2015, 15(33): 6432-6434.
LEE S,KIM H,KANG J,et al.The biflavonoid amentoflavone induces apoptosis via suppressing E7 expression,cell cycle arrest at sub-G₁ phase,and mitochondria-emanated intrinsic pathways in human cervical cancer cells[J].J Med Food,2011,14(7-8):808-816.
LIU B,YU S.Amentoflavone suppresses hepatocellular carcinoma by repressing hexokinase 2 expression through inhibiting JAK2/STAT3 signaling[J].Biomed Pharmacother, 2020, 130: 110635.
冯雪.穗花杉双黄酮和异银杏双黄酮的体内外代谢研究及其纳米胶束的制备与评价[D].石家庄:河北医科大学,2020.
CÁRDENAS M,MARDER M,BLANK V,et al.Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines[J]. Bioorg Med Chem, 2006, 14(9): 2966-2971.
LÓPEZ-POSADAS R,BALLESTER I,ABADÍA-MOLINA A,et al.Effect of flavonoids on rat splenocytes,a structure-activity relationship study[J].Biochem Pharmacol, 2008,76(4):495-506.
NABATI F,MORADI M,MOHABATKAR H.In silico analyzing the molecular interactions of plant-derived inhibitors against E6AP,p53,and c-Myc binding sites of HPV type 16 E6 oncoprotein[J]. Mol Biol Res Commun, 2020, 9(2): 71-82.
CHEN J,CHEN W,LIU Y.Amentoflavone Induces Anti-angiogenic and Anti-metastatic Effects Through Suppression of NF-κB Activation in MCF-7 cells[J]. Anticancer Res, 2015, 35(12): 6685-6693.
SUN L, SHARMA A, HAN B,et al.Amentoflavone:A Bifunctional Metal Chelator that Controls the Formation of Neurotoxic Soluble Aβ Oligomers[J].ACS Chem Neurosci, 2020, 11(17): 2741-2752.
GU Q, LI Y, CHEN Y,et al.Sciadopitysin:active component from Taxus chinensis for anti-Alzheimer’s disease[J]. Nat Prod Res, 2013, 27(22): 2157-2160.
KANG S,LEE J,CHOI Y,et al.Neuroprotective effects of naturally occurring biflavonoids[J].Bioorganic Med Chem Lett,2005, 15(15): 3588-3591.
张鹏,王峰,荣诗阔,等.阿曼托双黄酮在癫痫模型大鼠多囊卵巢发生中的保护作用[J].宁夏医科大学学报,2019, 41(11): 1081-1085.
李亚娟.异银杏双黄酮在帕金森病体外和体内模型中的神经保护作用探究[D].湛江:广东海洋大学,2019.
陈天然.银杏叶提取物主要成分对人凝血酶作用机制研究[D].郑州:郑州大学,2019.
贺光东.卷柏活性成分研究[D].郑州:河南大学,2009.
DELL'AGLI M,GALLI G,BOSISIO E.Inhibition of cGMP-phosphodiesterase-5 by biflavones of Ginkgo biloba[J].Planta Med, 2006, 72(5): 468-470.
CAI Y,LI Y.Protective Effect of Sciadopitysin against Isoproternol-Induced Myocardial Infarction in Rats[J].Pharmacology, 2020, 105(5-6): 272-280.
ALHARBI M,DUTTA B,GOSWAMI R,et al.Identification and functional analysis of a biflavone as a novel inhibitor of transient receptor potential vanilloid 4-dependent atherogenic processes[J].Sci Rep, 2021, 11(1): 8173.
LIU P,WENG Z,GE G,et al.Biflavones from Ginkgo biloba as novel pancreatic lipase inhibitors:Inhibition potentials and mechanism[J].Int J Biol Macromol,2018, 118(Pt B):2216-2223.
伍先明,李爱琼,周丽丽,等.银杏异双黄酮改善糖尿病大鼠足溃疡创面愈合的机制研究[J].湘南学院学报,2019, 21(4): 6-10.
CHOI E,SUH K,RHEE S,et al.Sciadopitysin alleviates methylglyoxal-mediated glycation in osteoblastic MC3T3-E1 cells by enhancing glyoxalase system and mitochondrial biogenesis[J].Free Radic Res, 2014, 48(7): 729-739.
QU X,LI Q,ZHANG X,et al.Amentoflavone protects the hematopoietic system of mice against γ-irradiation[J].Arch Pharm Res, 2019, 42(11): 1021-1029.
李利,赵远胜,杜飞飞,等.标准银杏叶提取物GBE50中多种活性成分的肠道吸收和系统前处置研究[C]//.中国药学会中药和天然药专业委员会.中药与天然药高峰论坛暨第十二届全国中药和天然药物学术研讨会论文集.海口:中国海口出版社,2012: 458.
孙旭.黄酮类化合物生物利用度影响因素研究进展[J].中华中医药杂志,2015, 30(9): 3231-3233.
王彦志,张萌,刘阳,等.穗花杉双黄酮在大鼠体内的药动学研究[J].中成药,2015,37(11):2397-2401.
YANG S,QU R,ZHU Z,et al.Validated LC-MS/MS method for the quantification of sciadopitysin in rat plasma and its application to pharmacokinetic and bioavailability studies in vivo[J].Biomed Chromatogr, 2019, 33(2): e4429.
LIAO S,REN Q,YANG C,et al.Liquid chromatography-tandem mass spectrometry determination and pharmacokinetic analysis of amentoflavone and its conjugated metabolites in rats[J].J Agric Food Chem, 2015, 63(7): 1957-1966.
任秋霞,王亚男,曲新艳,等.穗花杉双黄酮自微乳化给药系统的制备及体外评价[J].中国实验方剂学杂志,2013, 19(24): 5-9.
任秋霞,周喆,王升启.基于反溶剂冻干技术穗花杉双黄酮的制备和分析表征[J].国际药学研究杂志,2013, 40(2): 237-241.
乔雪,果德安,叶敏.中药体内代谢研究的思路与方法[J].世界科学技术-中医药现代化,2014, 16(3): 532-537.
王彦志,张萌,刘阳,等.穗花杉双黄酮在大鼠体内的组织分布研究[J].世界科学技术-中医药现代化,2015, 17(3): 536-543.
GUTMANN H,BRUGGISSER R,SCHAFFNER W,et al.Transport of amentoflavone across the blood-brain barrier in vitro[J].Planta Med, 2002, 68(9): 804-807.
韦丹丹,陈骁,赵建娟,等.穗花杉双黄酮大鼠在体肠吸收动力学的研究[J].药学与临床研究,2017, 25(4): 282-285.
COLOVIC M,FRACASSO C,CACCIA S.Brain-to-plasma distribution ratio of the biflavone amentoflavone in the mouse[J].Drug Metab Lett, 2008, 2(2): 90-94.
FENG X,CHEN Y,LI L,et al.Preparation,evaluation and metabolites study in rats of novel amentoflavone-loaded TPGS/soluplus mixed nanomicelles[J].Drug Deliv,2020,27(1):137-150.
FENG X,ZHANG X,CHEN Y,et al.Identification of bilobetin metabolites,in vivo and in vitro,based on an efficient ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry strategy[J]. J Sep Sci, 2020, 43(17): 3408-3420.
QIAN Y,JIANG S,ZHU Z,et al.Simultaneous quantification and semi-quantification of amentoflavone and its metabolites in human intestinal bacteria by liquid chromatography Orbitrap high-resolution mass spectrometry[J]. Biomed Chromatogr, 2017, 31(11): e3990.
WANG B,LU Y,HU X,et al.In VivoSystematic Strategy for Metabolites of Amentoflavone and Based on UHPLC-Q-TOF-MS/MS Analysis[J].J Agric Food Chem, 2020, 68(50): 14808-14823.
SON H,KANG W.Quantitative determination of bilobetin in rat plasma by HPLC-MS/MS and its application to a pharmacokinetic study[J]. Biomed Chromatogr, 2020, 34(4): e4784.
ZHAO C,HAN S,YANG S,et al.Validation and application of a novel LC/MS/MS method for the determination of isoginkgetin in rat plasma[J]. Biomed Chromatogr, 2019, 33(11): e4667.
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