Volume 35 Issue 3
May  2019
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CHEN Cheng, CHEN Li, SUN Jian-bo. Research Progress on Sources， Structural Modification and New Dosage Forms of Ginkgolides[J]. Journal of Nanjing University of traditional Chinese Medicine, 2019, 35(3): 344-350.
Citation: CHEN Cheng, CHEN Li, SUN Jian-bo. Research Progress on Sources， Structural Modification and New Dosage Forms of Ginkgolides[J]. Journal of Nanjing University of traditional Chinese Medicine, 2019, 35(3): 344-350.
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Research Progress on Sources， Structural Modification and New Dosage Forms of Ginkgolides

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    • Abstract
  • Ginkgolide is a kind of azlactone compound isolated from Ginkgo biloba leaves and roots. It acts as a potent platelet activating factor (PAF) antagonist and non-specific Glycine receptor (GlyR) and γ- Γ-Amino-Bu-Tyric acid (GABA) receptor antagonists are widely used in cardiovascular and cerebrovascular diseases. Since the discovery of PAF antagonistic activity of lactone components in Ginkgo biloba extract， many scientists have conducted extensive research on the structure-activity relationship， structural modification， and pharmacological effects of such compounds. As a natural drug， ginkgolides have the advantages of good curative effect and small side effects， and have a good development trend. The research and development of ginkgolides， ginkgolides and their preparations will bring better economic and social benefits. For the benefit of mankind. This article reviews the research and recent progress of ginkgolides， and reviews its development process and related research， with a view to bringing new thinking to the development of natural medicines.
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  • [1]
    国家药典委员会.中华人民共和国药典：一部[S]. 北京：中国医药科技出版社，2015：316.
    [2]
    BRUNO C， CUPPINI R， SARTINI S， et al. Regeneration of mator nerves in bilobalide-treated rats[J]. Planta Med， 1993， 59(4):302-307.
    [3]
    BRAQUET P. The ginkgolides: potent platelet-activating factor antagonists isolated from Ginkgo biloba leaves: chemistry， pharmacology and clinical applications[J]. Drug Future， 1987， 12:643-699.
    [4]
    LIDIJA I， TRISTAN JS， NATHAN F， et al. Terpene Trilactones from Ginkgo biloba Are Antagonists of Cortical Glycine and GABAA Receptors[J]. J Biol Chem，2003，278(49):49279-49285.
    [5]
    MARUYAMA M， TERAHARA A， NAKADAIRA， Y， et al. The ginkgolides Ⅵ. Stereochemistry of the ginkgolides[J]. Tetrahedron Lett， 1967， 4: 315-319.
    [6]
    NAKANISHI K. The ginkgolides[J]. Pure Appl Chem， 1967， 14: 89-113.
    [7]
    OKABE K， YAMADA K， YAMAMURA S， et al. Ginkgolides[J]. J Chem Soc C， 1967， 7（7）：2201-2206.
    [8]
    SAKABE N， TAKADA S， OKABE K． The structure of ginkgolide A，a novel diterpenoid trilactone[J]. Chem Comm， 1967， 6(6):259.
    [9]
    WEINGES K， HEPP M， JAGGY H. Chemie der Ginkgolide， II. Isolierung und Strukturaufklrung eines neuen Ginkgolids[J]. Eur J Org Chem， 1987， 1987(6):521-526.
    [10]
    NAKANISHI K， HABAGUCHI K， NAKADAIRA Y. Structure of bilobalide， a rare tert-butyl containing seuqiterpenoid related to the C20-ginkgolides[J]. J Am Chem Soc，1971， 93:3544-3546.
    [11]
    王颖，盛龙生，楼凤昌．银杏内酯提取物中微量成分的 LCDAD-ESI-MS分析及结构鉴定[J]. 药学学报， 2001， 36(8): 606.
    [12]
    ZHANG XT， LI Y， ZHANG LH， et al. A new ginkgolide from Ginkgo biloba[J]. J China Pharm， 2009， 40(4): 306.
    [13]
    LIAO HJ， ZHENG YF， LI HY， et al. Two new ginkgolides from the leaves of Ginkgo biloba[J]. Planta Med， 2011， 77(16): 1818.
    [14]
    BRAQUET P， TOUQUI L， SHEN TY， et al. Perspectives in platelet-activating factor research[J]. Pharmacol Rev， 1987， 39(2):97-145.
    [15]
    王奎龙， 李卓琼， 曹泽彧. 银杏二萜内酯 A， B， K 抗血小板聚集作用机制研究[J]. 中国中药杂志， 2017， 42(24):4722-4726.
    [16]
    LIU XQ， YAN Y， BAO L， et al. Ginkgolide B inhibits platelet release by blocking Syk and p38 MAPK phosphorylation in thrombin-stimulated platelets[J]. Throm Res， 2014， 134(5):1066-1073.
    [17]
    ZHANG W， SONG JK， YAN R， et al. Diterpene ginkgolides protect against cerebral ischemia/reperfusion damage in rats by activating Nrf2 and CREB through PI3K/Akt signaling[J]. Acta Pharmacol Sin， 2018， 39:1259-1272.
    [18]
    HU YY， HUANG M， DONG XQ， et al. Ginkgolide B reduces neuronal cell apoptosis in the hemorrhagic rat brain: Possible involvement of Toll-like receptor 4/nuclear factor-kappa B pathway[J]. J Ethnopharmacol， 2011， 137(3):1462-1468.
    [19]
    WANG X， JIANG CM， WAN HY， et al. Neuroprotection against permanent focal cerebral ischemia by ginkgolides A and B is associated with obstruction of the mitochondrial apoptotic pathway via inhibition of c-Jun N-terminal kinase in rats[J]. J Neurosci Res， 2014， 92(2):232-242.
    [20]
    MA SW， LIU XY， XUN QR， et al. Neuroprotective effect of ginkgolide K against H2O2-induced PC12 cell cytotoxicity by ameliorating mitochondrial dysfunction and oxidative stress[J]. Biol Pharm Bull， 2014， 37(2):217-225.
    [21]
    ZHOU JM， GU SS， MEI WH， et al. Ginkgolides and bilobalide protect BV2 microglia cells against OGD/reoxygenation injury by inhibiting TLR2/4 signaling pathways[J]. Cell Stress Chaperon， 2016， 21(6):1037-1053.
    [22]
    HU Q， SHEN P， BAI S， et al. Metabolite-related antidepressant action of diterpene ginkgolides in the prefrontal cortex[J]. Neuropsychiatr Dis Treat， 2018， 14:999-1011.
    [23]
    WANG L， SHI QH， LI K， et al. Oral administration of Ginkgolide B alleviates hypoxia-induced neuronal damage in rat hippocampus by inhibiting oxidative stress and apoptosis[J]. Iranian J Basic Med Sci， 2019， 22:1-6.
    [24]
    CHU X， CI XX， HE JK， et al. A Novel Anti-Inflammatory Role for Ginkgolide B in Asthma via Inhibition of the ERK/MAPK Signaling Pathway[J]. Molecules， 2011， 16(9):7634-7648.
    [25]
    JEONG HS， KIM KH， LEE IS， et al. Ginkgolide A ameliorates non-alcoholic fatty liver diseases on high fat diet mice[J]. Biomed Pharmacother， 2017， 88:625-634.
    [26]
    李文东，高乾善，杨鹏，等. 银杏叶中银杏内酯提取工艺研[J].山东科学， 2016， 29(5):29-35.
    [27]
    陆敏强， 黄辉庆， 李瑞明. 银杏叶中银杏总内酯提取工艺研究[J]. 中国医药导报， 2010， 8(23):72-73.
    [28]
    张晴晴， 喻明军， 曹帅. 银杏叶中银杏内酯的提取工艺优化[J]. 工艺与设备， 2017， 43(4):115-116.
    [29]
    ZU YG， WANG LL， ZHAO XH， et al. Purification of Ginkgo biloba Extract by Antisolvent Recrystallization[J]. Chem Eng Tech， 2016， 39(7):1301-1308.
    [30]
    李玉梅. 一种银杏内酯化合物制备方法:200810219837.X[P]. 2010-06-23.
    [31]
    肖志勇， 吕署一， 李玉杰， 等， 一种从银杏叶中提取的银杏内酯化合物及其制备方法: 201711419251.3[P]. 2017-12-25.
    [32]
    于垂亮， 肖志勇， 徐继红， 等.银杏内酯的提取和精制方法:201310368411.1[P]. 2013-08-21.
    [33]
    孙莉莉， 罗增桂， 唐江明， 等. 从银杏叶中提取分离白果内酯的方法:200710050244.0[P]. 2009-07-01.
    [34]
    COREY EJ， KANG MC， DESAI MC， et al. Total synthesis of (±)-ginkgolides B[J]. J Am Chem Soc， 1988， 110:649-651.
    [35]
    COREY EJ， GHOSH AK. Total synthesis of ginkgolide A[J]. Tetrahedron Letters， 1988， 29 (26):3205-3206.
    [36]
    COREY EJ， SU WG. Enantioselective total synthesis of bilobalide， A C15 ginkgolide[J]. Tetrahedron Lett， 1988， 29(28):3423-3426.
    [37]
    COREY EJ， RAO KS. Enantioselective total synthesis of ginkgolide derivatives lacking the tert-butyl group， an essential structural subunit for antagonism of platelet activating factor[J]. Tetrahedron Lett， 1991， 32(36): 4623-4626.
    [38]
    TENG BP. Preparation process of ginkgolide B from ginkgolide C: US5599950A[P]. 1997-02-04.
    [39]
    ZENG ZH， ZHU JH， CHEN LL， et al. Biosynthesis pathways of ginkgolides[J]. Pharmacogn Rev， 2013， 7(13): 47-52.
    [40]
    LIAO YL， XU F， HUANG XH， et al. Characterization and Transcriptional Profiling of Ginkgo biloba Mevalonate Diphosphate Decarboxylase Gene (GbMVD) Promoter Towards Light and Exogenous Hormone Treatments[J]. Plant Mol Biol Rep， 2016， 34(3):566-581.
    [41]
    CHEN L， TONG H， WANG M， et al. Effect of enzyme inhibitors on terpene trilactones biosynthesis and gene expression profiling in Ginkgo biloba Cultured Cells[J]. Nat Prod Commun， 2015， 10(12):2033-2035.
    [42]
    CARTAYRADE A， NWAU E， SOHIER C， et al. Sites of synthesis， translocation and accumulation of ginkgolides and bilobalide[J]. Plant Physiol Biochem， 1997， 35(11): 859-868.
    [43]
    SUKITO A， TACHIBANA S. Effect of methyl jasmonate and salycilic acid synergism on enhancement of bilobalide and ginkgolide production by immobilized cell cultures of Ginkgo biloba[J]. Bioresources Bioprocess， 2016， 3:24.
    [44]
    JARACZ S， NAKANISHI K， JENSEN AA， et al. Ginkgolides and glycine receptors: A structure-activity relationship study[J]. Chem Eur J， 2004， 10(6):1507-1518.
    [45]
    BRAQUET P， ESANU A. Ginkgolide derivatives:GB 2211841A[P].1989-07-12.
    [46]
    HU LH， CHEN ZL， XIE YY， et al. Alkyl and alkoxycarbonyl derivatives of ginkgolide B: Synthesis and biological evaluation of PAF inhibitory activity[J]. Bioorg Med Chem， 2000， 8(6):1515-1521.
    [47]
    GUO CJ， REN Y， QIN YL，et al. The synthesis and biological evaluation of 10-O-dialkylaminoethyl ginkgolide B as platelet-activating factor antagonist[J]. J Asian Nat Prod Res， 2008， 10:989-992.
    [48]
    秦引林.甲磺酸10-O-(二甲基胺基乙基)银杏内酯B半水结晶及其制备方法：200710024748.5[P].2008-05-28.
    [49]
    VOGENSEN SB， STROMGAARD K， SHINDOU H， et al. Preparation of 7-substituted ginkgolide derivatives:potent platelet activating factor (PAF) receptor antagonists[J]. Med Chem， 2003， 46 (4):601-608.
    [50]
    ZEKRI O， BOUDEVILLE P， GENAY P， et al. Ionization constants of ginkgolide B in aqueous solution[J]. Anal Chem， 1996， 68(15):2598-2604.
    [51]
    HU LH， CHEN ZL， CHEN XF， et al. Chemistry of ginkgolides: structure-activity relationship as PAF antagonists[J]. Pure Appl Chem，1999， 71（6）： 1153-1156.
    [52]
    COREY EJ， GAVAI AV. Simple analogues of ginkgolide B which are highly active antagonists of platelet activating factor[J]. Tetrahedron Lett， 1989， 30:6959-6962.
    [53]
    HU LH， CHEN ZL， XIE YY. Synthesis and biological activity of amide derivatives of ginkgolide A[J]. Asian Nat Prod Res， 2001， 3(3): 219-227.
    [54]
    HU LH， CHEN ZL， XIE YY， et al. New products from alkali fusion of Ginkgolides A and B[J]. Asian Nat Prod Res， 2000， 2(2): 103-110.
    [55]
    杨振强，徐明. 银杏内酯B的水溶性氨基酸酯衍生物：200910136605.2[P].2010-11-10.
    [56]
    ZHU WL， CHEN G， HU LH， et al. QSAR analyses on ginkgolides and their analogues using CoMFA， CoMSIA， and HQSAR[J]. Bioorg Med Chem， 2005， 13(2):313-322.
    [57]
    PIETRI S， LIEBGOTT T， FINET JP， et al. Synthesis and biological studies of a new ginkgolide C derivative: Evidence that the cardioprotective effect of ginkgolides is unrelated to PAF inhibition[J]. Drug Develop Res， 2001， 54:191-201.
    [58]
    GUTMAN TL. Targeted drug delivery for brain cancer treatment[J]. Control Release， 2000， 65(1/2): 31.
    [59]
    周小健，惠爱玲， 王园. 银杏内酯B的1，4-二氢吡啶酸酯衍生物的合成研究[J]. 安徽化工， 2013， 39(1):48-49.
    [60]
    萧伟，胡玉梅，孟兆青， 等. 银杏内酯K制剂及其制备方法:201610685356.2[P]. 2016-08-18.
    [61]
    萧伟，刘文君，陈益航，等.一种银杏内酯K滴丸及其制备方法:201610692242.0[P]. 2016-08-18.
    [62]
    萧伟，唐星，王振中，等.热熔挤出法制备银杏内酯B无定形固体分散体:201510884418.8[P]. 2015-12-06.
    [63]
    孙毅.一种含有银杏内酯B和Xa因子抑制剂的药物组合物及其制备方法和用途:201510726733.8[P]. 2015-10-30.
    [64]
    杨贤龙，何勇，吴宗好. 一种银杏内酯双层控释片及其制备方法:201711469101.3[P]. 2017-12-29.
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