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(−)-Bilobalide from Ginkgo biloba leaves - ≥93% (HPLC), high purity , CAS No.33570-04-6, Channel blocker of 5-HT 3A;Channel blocker of 5-HT 3AB;Antagonist of glycine receptor α1 subunit;Antagonist of glycine receptor α2 subunit;Antagonist of glycine receptor β subunit

  • Moligand™
  • ≥93%(HPLC)
Item Number
B432637
Grouped product items
SKUSizeAvailabilityPrice Qty
B432637-10mg
10mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$481.90
B432637-25mg
25mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,101.90
B432637-100mg
100mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$3,694.90

Basic Description

SynonymsBilobalide|33570-04-6|Bilobalid|(-)-Bilobalide|Bilobalide A|UNII-M81D2O8H7U|CHEBI:3103|M81D2O8H7U|DTXSID10873207|4H,5aH,9H-Furo(2,3-b)furo(3',2':2,3)cyclopenta(1,2-c)furan-2,4,7(3H,8H)-trione, 9-(1,1-dimethylethyl)-10,10a-dihydro-8,9-dihydroxy-, (5aR-(3aS
Specifications & PurityMoligand™, ≥93%(HPLC)
Biochemical and Physiological MechanismsBilobalide is an inducer of cytochrome P450 enzymes CYP3A1 and CYP1A2. It exhibits neuroprotective, anti-inflammatory, anti-oxidative and anti-apoptotic properties. Bilobalide, a γ-aminobutyric acid (GABA) A A -rho, 5-hydroxytryptamine type 3 (5-HT(3))
Storage TempStore at -20°C
Shipped InIce chest + Ice pads
GradeMoligand™
Action TypeANTAGONIST, CHANNEL BLOCKER
Mechanism of actionChannel blocker of 5-HT 3A;Channel blocker of 5-HT 3AB;Antagonist of glycine receptor α1 subunit;Antagonist of glycine receptor α2 subunit;Antagonist of glycine receptor β subunit
Product Description

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.

Associated Targets

CBX1 Tbio Chromobox protein homolog 1 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

GMNN Tbio Geminin 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

RUNX1 Tbio Runt-related transcription factor 1 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

KMT2A Tchem Histone-lysine N-methyltransferase 2A 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

GLRA2 Tchem Glycine receptor subunit alpha-2 1 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

SMN1 Tchem Survival motor neuron protein 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

ALOX15 Tchem Arachidonate 15-lipoxygenase 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

NR1I2 Tchem Nuclear receptor subfamily 1 group I member 2 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

NR1I3 Tchem Nuclear receptor subfamily 1 group I member 3 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

GNAS Tbio Protein ALEX 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

HTR3B Tchem 5-hydroxytryptamine receptor 3B 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

HTR3A Tclin 5-hydroxytryptamine receptor 3A 1 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

THRB Tclin Thyroid hormone receptor beta 0 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

GLRA1 Tclin Glycine receptor subunit alpha-1 1 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

GLRB Tclin Glycine receptor subunit beta 2 Activities

Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

Names and Identifiers

IUPAC 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 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
Canonical 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
WGK Germany 3
RTECS LV1665000
PubChem CID 73581
Molecular Weight 326.3

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Specific Rotation[α]-60° (C=1,Acetone)

Safety and Hazards(GHS)

WGK Germany 3
RTECS LV1665000
Merck Index 1220

Related Documents

References

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)): (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]

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