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(-)-来自 Ginkgo biloba 叶的 Bilobalide, 5-HT 3A 通道阻滞剂;5-HT 3AB 通道阻滞剂;甘氨酸受体 α1 亚基拮抗剂;甘氨酸受体 α2 亚基拮抗剂;甘氨酸受体 β 亚基拮抗剂

3篇引用文献 COA COA
  • CAS编号: 33570-04-6
  • 分子式: C15H18O8
  • 分子量: 326.3
  • PubChem编号: 73581
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货号 (SKU) 包装规格 是否现货 价格 数量
B432637-10mg
 10mg 期货 Stock Image
B432637-25mg
 25mg 期货 Stock Image
B432637-100mg
 100mg 期货 Stock Image
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5-HT3A Channel blocker (4) 5-HT3AB Channel blocker (2) Apoptosis (7108) Autophagy (2848) Glycine Receptor (All subtypes) Subunit-specific (18) glycine receptor α1 subunit Antagonist (8) glycine receptor α2 subunit Antagonist (8) glycine receptor β subunit Antagonist (5) 代谢物 (8911)
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基本描述

英文别名 (-)-Bilobalide | HY-N0076 | AS-17551 | BILOBALIDE [WHO-DD] | 2,5 Dibromotoluene | 2,5-Dichloro-p-quinone | MFCD00238547 | Q418459 | CCG-208160 | DTXSID10873207 | SMR000232342 | Bilobalide | SCHEMBL285824 | CHEBI:3103 | 5-Methyl-2-chlorophenol | 2-Chlor-4-
规格或纯度 Moligand™, ≥93%(HPLC)
英文名称 (−)-Bilobalide from Ginkgo biloba leaves
生化机理 比洛巴利特是细胞色素 P450 酶 CYP3A1 和 CYP1A2 的诱导剂。它具有神经保护、抗炎、抗氧化和抗细胞凋亡的特性。Bilobalide是一种γ-氨基丁酸（GABA）A A-rho、5-羟色胺3型（5-HT（3））受体拮抗剂，可用于研究这些受体在认知和记忆等大脑过程中的功能。它是一种特异性血小板活化因子受体拮抗剂，有助于治疗心血管疾病（老年痴呆症）和脑血管疾病。银杏叶中的生物活性萜类化合物。
储存温度 -20°C储存
运输条件 超低温冰袋运输
作用类型 拮抗剂
作用机制 5-HT 3A 通道阻滞剂;5-HT 3AB 通道阻滞剂;甘氨酸受体 α1 亚基拮抗剂;甘氨酸受体 α2 亚基拮抗剂;甘氨酸受体 β 亚基拮抗剂
产品介绍


General Description

Bilobalide is a biologically active terpenic trilactone (terpenoid) extracted from Ginkgo biloba . It is synthesized from geranylgeranyl pyrophosphate (GGPP).


Application

(-)-Bilobalide from Ginkgo biloba leaves has been used as a reference substance to study the antimicrobial activity of different fractions of G.biloba leaves against a number of Gram-positive and negative bacteria and yeasts.
纯度 ≥93%(HPLC)

关联靶点（人）

GLRA2 Tchem 甘氨酸受体亚基 α-2(Glycine receptor subunit alpha-2) (1 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
HTR3B Tchem 5-羟色胺受体 3B(5-hydroxytryptamine receptor 3B) (0 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
HTR3A Tclin 5-羟色胺受体 3A(5-hydroxytryptamine receptor 3A) (1 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
GLRA1 Tclin 甘氨酸受体亚基 α-1(Glycine receptor subunit alpha-1) (1 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
GLRB Tclin 甘氨酸受体亚基β(Glycine receptor subunit beta) (2 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
THRB Tclin Thyroid hormone receptor beta-1 (7926 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
NR1I2 Tchem Pregnane X receptor (6667 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HepG2 (196354 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
NR1I3 Tchem Nuclear receptor subfamily 1 group I member 3 (655 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SMN1 Tchem Survival motor neuron protein (34246 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GMNN Tbio Geminin (128009 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

关联靶点（其它种属）

PC-12 (7051 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

分子类型 小分子
IIUPAC Name (1S,4R,7R,8S,9R,11S)-9-tert-butyl-7,9-dihydroxy-3,5,12-trioxatetracyclo[6.6.0.01,11.04,8]tetradecane-2,6,13-trione
INCHI 1S/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8-,11-,13-,14+,15+/m0/s1
InChi Key MOLPUWBMSBJXER-YDGSQGCISA-N
Smiles CC(C)(C)C1(CC2C3(C14C(C(=O)OC4OC3=O)O)CC(=O)O2)O
Isomeric SMILES CC(C)(C)[C@@]1(C[C@H]2[C@@]3([C@]14[C@H](C(=O)O[C@H]4OC3=O)O)CC(=O)O2)O
分子量 326.3
Reaxy-Rn 9144268
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9144268&ln=

化学和物理性质

比旋光度 -60° (C=1,Acetone)
分子量 326.300 g/mol
XLogP3 -0.300
氢键供体数Hydrogen Bond Donor Count 2
氢键受体数Hydrogen Bond Acceptor Count 8
可旋转键计数Rotatable Bond Count 1
精确质量Exact Mass 326.1 Da
单同位素质量Monoisotopic Mass 326.1 Da
拓扑极表面积Topological Polar Surface Area 119.000 Ų
重原子数Heavy Atom Count 23
形式电荷Formal Charge 0
复杂度Complexity 650.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 6
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 0
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 0
共价键合单元计数Covalently-Bonded Unit Count 1

安全和危险性（GHS）

WGK Germany 3
RTECS LV1665000
Merck Index 1220
个人防护装备 Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

质检证书（CoA,COO,BSE/TSE 和分析图谱)

C of A & Other Certificates(BSE/TSE, COO):
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此产品的引用文献

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引用文献

1. Thompson AJ, Jarvis GE, Duke RK, Johnston GA, Lummis SC.  (2011)  Ginkgolide B and bilobalide block the pore of the 5-HT(3) receptor at a location that overlaps the picrotoxin binding site..  Neuropharmacology,  60  (2-3): (488-95).  [PMID:21059362]
2. Thompson AJ, Duke RK, Lummis SC.  (2011)  Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor..  Mol Pharmacol,  80  (1): (183-90).  [PMID:21505038]
3. Francis V Defeudis.  (2002-11-30)  Bilobalide and neuroprotection..  Pharmacological research,  46  ((6)): (565-568).  [PMID:12457632]
4. Teris A van Beek.  (2005-07-05)  Ginkgolides and bilobalide: their physical, chromatographic and spectroscopic properties..  Bioorganic & medicinal chemistry,  13  ((17)): (5001-5012).  [PMID:15993092]
5. Marishka K Brown,Yuan Luo.  (2009-06-24)  Bilobalide modulates serotonin-controlled behaviors in the nematode Caenorhabditis elegans..  BMC neuroscience,  10  (62-62).  [PMID:19545409]
6. Pushpinder Kaur,Abha Chaudhary,Bikram Singh,Gopichand.  (2009-07-21)  Optimization of extraction technique and validation of developed RP-HPLC-ELSD method for determination of terpene trilactones in Ginkgo biloba leaves..  Journal of pharmaceutical and biomedical analysis,  50  ((5)): (1060-1064).  [PMID:19616398]
7. Li Zhang,Ji-Qu Xu,Shuang Rong,Bi-Jun Xie,Zhi-Da Sun,Yun-Jian Zhang,Lie-Gang Liu.  (2009-07-28)  The mixture of procyanidins extracted from the lotus seed pod and bilobalide ameliorates scopolamine-induced memory impairment in mice..  Neuroscience bulletin,  25  ((4)): (203-208).  [PMID:19633702]
8. Karin Woelkart,Elisabeth Feizlmayr,Peter Dittrich,Eckhard Beubler,Fritz Pinl,Andy Suter,Rudolf Bauer.  (2009-12-31)  Pharmacokinetics of bilobalide, ginkgolide A and B after administration of three different Ginkgo biloba L. preparations in humans..  Phytotherapy research : PTR,  24  ((3)): (445-450).  [PMID:20041430]
9. Dorothee Lang,Christian Ude,Mario Wurglics,Manfred Schubert-Zsilavecz,Jochen Klein.  (2010-01-01)  Brain permeability of bilobalide as probed by microdialysis before and after middle cerebral artery occlusion in mice..  Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques,  13  ((4)): (607-614).  [PMID:21486534]
10. Chun Shi,Fengming Wu,Jie Xu,Juntao Zou.  (2011-06-18)  Bilobalide regulates soluble amyloid precursor protein release via phosphatidyl inositol 3 kinase-dependent pathway..  Neurochemistry international,  59  ((1)): (59-64).  [PMID:21679734]
11. Alice C Rodrigues,Xin Li,Laura Radecki,Yu-Zhuo Pan,Jerrold C Winter,Min Huang,Ai-Ming Yu.  (2011-07-29)  MicroRNA expression is differentially altered by xenobiotic drugs in different human cell lines..  Biopharmaceutics & drug disposition,  32  ((6)): (355-367).  [PMID:21796641]
12. Maciej A Pszczolkowski,Kevin Durden,Samantha Sellars,Brian Cowell,John J Brown.  (2011-09-13)  Effects of Ginkgo biloba constituents on fruit-infesting behavior of codling moth (Cydia pomonella) in apples..  Journal of agricultural and food chemistry,  59  ((20)): (10879-10886).  [PMID:21905729]
13. Menghao Huang,Yisong Qian,Teng Guan,Longfei Huang,Xuzhen Tang,Yunman Li.  (2011-12-27)  Different neuroprotective responses of Ginkgolide B and bilobalide, the two Ginkgo components, in ischemic rats with hyperglycemia..  European journal of pharmacology,  677  ((1-3)): (71-76).  [PMID:22197649]
14. Limei Han,Yan Fu,Adam J Cole,Jie Liu,Jianxin Wang.  (2012-03-15)  Co-encapsulation and sustained-release of four components in ginkgo terpenes from injectable PELGE nanoparticles..  Fitoterapia,  83  ((4)): (721-731).  [PMID:22414318]
15. José G Napolitano,David C Lankin,Shao-Nong Chen,Guido F Pauli.  (2012-06-26)  Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba..  Magnetic resonance in chemistry : MRC,  50  ((8)): (569-575).  [PMID:22730238]
16. Leige Ma,Shiyan Wang,Fadao Tai,Gang Yuan,Ruiyong Wu,Xiao Liu,Bin Wei,Xiangping Yang.  (2012-10-23)  Effects of bilobalide on anxiety, spatial learning, memory and levels of hippocampal glucocorticoid receptors in male Kunming mice..  Phytomedicine : international journal of phytotherapy and phytopharmacology,  20  ((1)): (89-96).  [PMID:23083816]
17. T M Schwarzkopf,S Hagl,G P Eckert,J Klein.  (2013-08-09)  Neuroprotection by bilobalide in ischemia: improvement of mitochondrial function..  Die Pharmazie,  68  ((7)): (584-589).  [PMID:23923641]
18. Haixia Lin,Xiaoqing Guo,Suhui Zhang,Stacey L Dial,Lei Guo,Mugimane G Manjanatha,Martha M Moore,Nan Mei.  (2014-03-07)  Mechanistic evaluation of Ginkgo biloba leaf extract-induced genotoxicity in L5178Y cells..  Toxicological sciences : an official journal of the Society of Toxicology,  139  ((2)): (338-349).  [PMID:24595819]
19. A Priyanka,V M Nisha,S S Anusree,K G Raghu.  (2014-07-22)  Bilobalide attenuates hypoxia induced oxidative stress, inflammation, and mitochondrial dysfunctions in 3T3-L1 adipocytes via its antioxidant potential..  Free radical research,  48  ((10)): (1206-1217).  [PMID:25039303]
20. Bin Zheng,Lirong Teng,Gaoyang Xing,Ye Bi,Shuang Yang,Fei Hao,Guodong Yan,Xinmei Wang,Robert J Lee,Lesheng Teng,Jing Xie.  (2015-06-28)  Proliposomes containing a bile salt for oral delivery of Ginkgo biloba extract: Formulation optimization, characterization, oral bioavailability and tissue distribution in rats..  European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences,  77  (254-264).  [PMID:26116277]
21. A F Sviridov.  (1991-10-01)  [Gingkolides and bilobalide: structure, pharmacology, and synthesis]..  Bioorganicheskaia khimiia,  17  ((10)): (1301-1312).  [PMID:1804115]
22. Shelley H Huang,Rujee K Duke,Mary Chebib,Keiko Sasaki,Keiji Wada,Graham A R Johnston.  (2003-02-26)  Bilobalide, a sesquiterpene trilactone from Ginkgo biloba, is an antagonist at recombinant alpha1beta2gamma2L GABA(A) receptors..  European journal of pharmacology,  464  ((1)): (1-8).  [PMID:12600688]
23. Vamsi L M Madgula,Bharathi Avula,Young-Beob Yu,Yan-Hong Wang,Flaubert Tchantchou,Scott Fisher,Yuan Luo,Ikhlas A Khan,Shabana I Khan.  (2009-11-26)  Intestinal and blood-brain barrier permeability of ginkgolides and bilobalide: in vitro and in vivo approaches..  Planta medica,  76  ((6)): (599-606).  [PMID:19937548]
24. T Yoshitake,S Yoshitake,J Kehr.  (2010-01-29)  The Ginkgo biloba extract EGb 761(R) and its main constituent flavonoids and ginkgolides increase extracellular dopamine levels in the rat prefrontal cortex..  British journal of pharmacology,  159  ((3)): (659-668).  [PMID:20105177]
25. Chun Shi,Fengming Wu,David T Yew,Jie Xu,Yonghong Zhu.  (2010-03-25)  Bilobalide prevents apoptosis through activation of the PI3K/Akt pathway in SH-SY5Y cells..  Apoptosis : an international journal on programmed cell death,  15  ((6)): (715-727).  [PMID:20333467]
26. Chun Shi,Juntao Zou,Guoying Li,Zhenying Ge,Zhibin Yao,Jie Xu.  (2010-05-22)  Bilobalide protects mitochondrial function in ovariectomized rats by up-regulation of mRNA and protein expression of cytochrome c oxidase subunit I..  Journal of molecular neuroscience : MN,  45  ((2)): (69-75).  [PMID:20490713]
27. Soo Lim,Ji Won Yoon,Seon Mee Kang,Sung Hee Choi,Bong Jun Cho,Min Kim,Ho Seon Park,Hyun Ju Cho,Hayley Shin,Young-Bum Kim,Hyo Soo Kim,Hak Chul Jang,Kyong Soo Park.  (2011-06-10)  EGb761, a Ginkgo biloba extract, is effective against atherosclerosis in vitro, and in a rat model of type 2 diabetes..  PloS one,  6  ((6)): (e20301-e20301).  [PMID:21655098]
28. Etsuko Suzuki,Makiko Sato,Ryota Takezawa,Toyonobu Usuki,Takashi Okada.  (2011-06-29)  The facilitative effects of bilobalide, a unique constituent of Ginkgo biloba, on synaptic transmission and plasticity in hippocampal subfields..  The journal of physiological sciences : JPS,  61  ((5)): (421-427).  [PMID:21710296]
29. Yuko Taki,Kaori Yokotani,Shizuo Yamada,Kazumasa Shinozuka,Yoko Kubota,Yasuo Watanabe,Keizo Umegaki.  (2011-08-02)  Ginkgo biloba extract attenuates warfarin-mediated anticoagulation through induction of hepatic cytochrome P450 enzymes by bilobalide in mice..  Phytomedicine : international journal of phytotherapy and phytopharmacology,  19  ((2)): (177-182).  [PMID:21802929]
30. Chun Shi,Dong-dan Zheng,Feng-ming Wu,Jun Liu,Jie Xu.  (2011-09-29)  The phosphatidyl inositol 3 kinase-glycogen synthase kinase 3β pathway mediates bilobalide-induced reduction in amyloid β-peptide..  Neurochemical research,  37  ((2)): (298-306).  [PMID:21952928]
31. Aik Jiang Lau,Guixiang Yang,Ganesh Rajaraman,Christie C Baucom,Thomas K H Chang.  (2011-10-25)  Species-dependent and receptor-selective action of bilobalide on the function of constitutive androstane receptor and pregnane X receptor..  Drug metabolism and disposition: the biological fate of chemicals,  40  ((1)): (178-186).  [PMID:22019630]
32. Dorothee Lang,Cornelia Kiewert,Alexander Mdzinarishvili,Tina Maria Schwarzkopf,Rachita Sumbria,Joachim Hartmann,Jochen Klein.  (2011-10-29)  Neuroprotective effects of bilobalide are accompanied by a reduction of ischemia-induced glutamate release in vivo..  Brain research,  1425  (155-163).  [PMID:22032877]
33. Lingling Wang, Xiuhua Zhao, Fengjian Yang, Weiwei Wu, Yanjie Liu, Li Wang, Lu Wang, Zijian Wang.  (2019)  Enhanced bioaccessibility in vitro and bioavailability of Ginkgo biloba extract nanoparticles prepared by liquid anti-solvent precipitation.  INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY,  54  (6): (2266-2276).  [10.1111/ijfs.14141]
34. Lingling Wang, Xiuhua Zhao, Yuangang Zu, Weiwei Wu, Yuanyuan Li, Chang Zu, Yin Zhang.  (2016)  Enhanced dissolution rate and oral bioavailability of ginkgo biloba extract by preparing nanoparticles via emulsion solvent evaporation combined with freeze drying (ESE-FR).  RSC Advances,  6  (81): (77346-77357).  [10.1039/C6RA14771B]
35. Yuan Gang Zu, Lingling Wang, Xiuhua Zhao, Yuanyuan Li, Weiwei Wu, Chang Zu, Yannian Huang, Mingfang Wu, Ziqi Feng.  (2016)  Purification of Ginkgo biloba Extract by Antisolvent Recrystallization.  CHEMICAL ENGINEERING & TECHNOLOGY,  39  (7): (1301-1308).  [10.1002/ceat.201500691]

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