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MedKoo Cat#: 573969 | Name: Bilobetin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bilobetin is a biflavonoid that has been found in G. biloba and has diverse biological activities. It is cytotoxic to HeLa, NCI-H460, Daudi, K562, SKOV3, MIA PaCa-2, and MCF-7 cells in vitro.

Chemical Structure

Bilobetin
Bilobetin
CAS#521-32-4

Theoretical Analysis

MedKoo Cat#: 573969

Name: Bilobetin

CAS#: 521-32-4

Chemical Formula: C31H20O10

Exact Mass: 552.1056

Molecular Weight: 552.49

Elemental Analysis: C, 67.39; H, 3.65; O, 28.96

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 800.00 2 Weeks
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Related CAS #
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Synonym
Bilobetin
IUPAC/Chemical Name
8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
InChi Key
IWEIJEPIYMAGTH-UHFFFAOYSA-N
InChi Code
InChI=1S/C31H20O10/c1-39-24-7-4-15(26-12-22(37)29-19(34)9-17(33)10-27(29)40-26)8-18(24)28-20(35)11-21(36)30-23(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3
SMILES Code
OC1=CC(O)=C2C(OC(C3=CC=C(O)C=C3)=CC2=O)=C1C4=CC(C(OC5=C6C(O)=CC(O)=C5)=CC6=O)=CC=C4OC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Origin: Plant/Ginkgo biloba L.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bilobetin, an active component of Ginkgo biloba, can reduce blood lipids and improve the effects of insulin.
In vitro activity:
IGF-1 treatment increased lipid production, and pretreatment with bilobetin resulted in significant inhibition of IGF-1–induced lipid production (Fig. 2B). Result showed that bilobetin markedly inhibited IGF-1–induced lipid production, including squalene and wax ester. In addition, bilobetin also blocked significantly the production of triglyceride and cholesterol (Fig. 2C). Reference: Ann Dermatol. 2019 Jun; 31(3): 294–299. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7992725/
In vivo activity:
In this study, rats were injected with 50 mg/kg of bilobetin, a biflavone isolated from Gb, for 7 days and aristolochic acid was used as positive controls. The results showed that the body weight and urine output of the rats were dramatically decreased, and urinary protein increased after the intraperitoneal injection of bilobetin compared with the control group. Bilobetin treatment showed vacuolar degeneration in the renal tubular epithelium, glomerular atrophy by histostaining, and podocyte fusion by electron microscopy. Reference: Phytomedicine. 2019 Nov;64:153073. https://pubmed.ncbi.nlm.nih.gov/31542661/
Solvent mg/mL mM comments
Solubility
DMSO 137.5 248.87
DMSO:PBS (pH 7.2) (1:6) 0.1 0.25
DMF 10.0 18.10
Ethanol 2.5 4.52
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 552.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wang Q, Wu ZL, Yuan X, Dong HY, Xu X, Xin H, Wang YH, Zhang JB, Chen L, Li HL, Zhang XM, Zhang WD. Bilobetin induces kidney injury by influencing cGMP-mediated AQP-2 trafficking and podocyte cell cycle arrest. Phytomedicine. 2019 Nov;64:153073. doi: 10.1016/j.phymed.2019.153073. Epub 2019 Aug 23. PMID: 31542661. 2. Wang C, Hwang YL, Li XM, Kim SJ, Zhu MJ, Lee JH, Jiang RH, Kim CD. Inhibition of Insulin-Like Growth Factor-1-Induced Sebum Production by Bilobetin in Cultured Human Sebocytes. Ann Dermatol. 2019 Jun;31(3):294-299. doi: 10.5021/ad.2019.31.3.294. Epub 2019 May 1. PMID: 33911594; PMCID: PMC7992725. 3. Kou XH, Zhu MF, Chen D, Lu Y, Song HZ, Ye JL, Yue LF. Bilobetin ameliorates insulin resistance by PKA-mediated phosphorylation of PPARα in rats fed a high-fat diet. Br J Pharmacol. 2012 Apr;165(8):2692-706. doi: 10.1111/j.1476-5381.2011.01727.x. PMID: 22091731; PMCID: PMC3423259.
In vitro protocol:
1. Wang Q, Wu ZL, Yuan X, Dong HY, Xu X, Xin H, Wang YH, Zhang JB, Chen L, Li HL, Zhang XM, Zhang WD. Bilobetin induces kidney injury by influencing cGMP-mediated AQP-2 trafficking and podocyte cell cycle arrest. Phytomedicine. 2019 Nov;64:153073. doi: 10.1016/j.phymed.2019.153073. Epub 2019 Aug 23. PMID: 31542661. 2. Wang C, Hwang YL, Li XM, Kim SJ, Zhu MJ, Lee JH, Jiang RH, Kim CD. Inhibition of Insulin-Like Growth Factor-1-Induced Sebum Production by Bilobetin in Cultured Human Sebocytes. Ann Dermatol. 2019 Jun;31(3):294-299. doi: 10.5021/ad.2019.31.3.294. Epub 2019 May 1. PMID: 33911594; PMCID: PMC7992725.
In vivo protocol:
1. Wang Q, Wu ZL, Yuan X, Dong HY, Xu X, Xin H, Wang YH, Zhang JB, Chen L, Li HL, Zhang XM, Zhang WD. Bilobetin induces kidney injury by influencing cGMP-mediated AQP-2 trafficking and podocyte cell cycle arrest. Phytomedicine. 2019 Nov;64:153073. doi: 10.1016/j.phymed.2019.153073. Epub 2019 Aug 23. PMID: 31542661. 2. Kou XH, Zhu MF, Chen D, Lu Y, Song HZ, Ye JL, Yue LF. Bilobetin ameliorates insulin resistance by PKA-mediated phosphorylation of PPARα in rats fed a high-fat diet. Br J Pharmacol. 2012 Apr;165(8):2692-706. doi: 10.1111/j.1476-5381.2011.01727.x. PMID: 22091731; PMCID: PMC3423259.
1: Zhang J, Wang Y. Bilobetin, a novel small molecule inhibitor targeting influenza virus polymerase acidic (PA) endonuclease was screened from plant extracts. Nat Prod Res. 2021 Dec;35(24):5968-5971. doi: 10.1080/14786419.2020.1808636. Epub 2020 Aug 21. PMID: 32820654. 2: Son H, Kang W. Quantitative determination of bilobetin in rat plasma by HPLC- MS/MS and its application to a pharmacokinetic study. Biomed Chromatogr. 2020 Apr;34(4):e4784. doi: 10.1002/bmc.4784. Epub 2020 Jan 20. PMID: 31853982. 3: Negm WA, El-Kadem AH, Hussein IA, Alqahtani MJ. The Mechanistic Perspective of Bilobetin Protective Effects against Cisplatin-Induced Testicular Toxicity: Role of Nrf-2/Keap-1 Signaling, Inflammation, and Apoptosis. Biomedicines. 2022 May 13;10(5):1134. doi: 10.3390/biomedicines10051134. PMID: 35625871; PMCID: PMC9138600. 4: Wang Q, Wu ZL, Yuan X, Dong HY, Xu X, Xin H, Wang YH, Zhang JB, Chen L, Li HL, Zhang XM, Zhang WD. Bilobetin induces kidney injury by influencing cGMP- mediated AQP-2 trafficking and podocyte cell cycle arrest. Phytomedicine. 2019 Nov;64:153073. doi: 10.1016/j.phymed.2019.153073. Epub 2019 Aug 23. PMID: 31542661. 5: Patel DK. Biological Importance of a Biflavonoid 'Bilobetin' in the Medicine: Medicinal Importance, Pharmacological Activities and Analytical Aspects. Infect Disord Drug Targets. 2022;22(5):22-30. doi: 10.2174/1871526522666220321152036. PMID: 35319397. 6: Kou XH, Zhu MF, Chen D, Lu Y, Song HZ, Ye JL, Yue LF. Bilobetin ameliorates insulin resistance by PKA-mediated phosphorylation of PPARα in rats fed a high- fat diet. Br J Pharmacol. 2012 Apr;165(8):2692-706. doi: 10.1111/j.1476-5381.2011.01727.x. PMID: 22091731; PMCID: PMC3423259. 7: Feng X, Zhang X, Chen Y, Li L, Sun Q, Zhang L. 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 Sep Sci. 2020 Sep;43(17):3408-3420. doi: 10.1002/jssc.202000313. Epub 2020 Jul 8. PMID: 32573953. 8: Menezes JCJMDS, Diederich MF. Bioactivity of natural biflavonoids in metabolism-related disease and cancer therapies. Pharmacol Res. 2021 May;167:105525. doi: 10.1016/j.phrs.2021.105525. Epub 2021 Mar 3. PMID: 33667686. 9: Wang C, Hwang YL, Li XM, Kim SJ, Zhu MJ, Lee JH, Jiang RH, Kim CD. Inhibition of Insulin-Like Growth Factor-1-Induced Sebum Production by Bilobetin in Cultured Human Sebocytes. Ann Dermatol. 2019 Jun;31(3):294-299. doi: 10.5021/ad.2019.31.3.294. Epub 2019 May 1. PMID: 33911594; PMCID: PMC7992725. 10: Šamec D, Karalija E, Dahija S, Hassan STS. Biflavonoids: Important Contributions to the Health Benefits of Ginkgo (Ginkgo biloba L.). Plants (Basel). 2022 May 23;11(10):1381. doi: 10.3390/plants11101381. PMID: 35631806; PMCID: PMC9143338. 11: Krauze-Baranowska M, Wiwart M. Antifungal activity of biflavones from Taxus baccata and Ginkgo biloba. Z Naturforsch C J Biosci. 2003 Jan-Feb;58(1-2):65-9. doi: 10.1515/znc-2003-1-212. PMID: 12622229. 12: Menezes JCJMDS, Campos VR. Natural biflavonoids as potential therapeutic agents against microbial diseases. Sci Total Environ. 2021 May 15;769:145168. doi: 10.1016/j.scitotenv.2021.145168. Epub 2021 Jan 16. PMID: 33493916. 13: Bai J, Zhang C. Metabolic interaction between biflavonoids in Ginkgo biloba leaves and tacrolimus. Biopharm Drug Dispos. 2023 Apr;44(2):157-164. doi: 10.1002/bdd.2350. Epub 2023 Mar 11. PMID: 36840704. 14: Li M, Li B, Xia ZM, Tian Y, Zhang D, Rui WJ, Dong JX, Xiao FJ. Anticancer Effects of Five Biflavonoids from Ginkgo Biloba L. Male Flowers In Vitro. Molecules. 2019 Apr 16;24(8):1496. doi: 10.3390/molecules24081496. PMID: 30995808; PMCID: PMC6514578. 15: Kovač Tomas M, Jurčević I, Šamec D. Tissue-Specific Profiling of Biflavonoids in Ginkgo (Ginkgo biloba L.). Plants (Basel). 2022 Dec 28;12(1):147. doi: 10.3390/plants12010147. PMID: 36616276; PMCID: PMC9824678. 16: Li YY, Lu XY, Sun JL, Wang QQ, Zhang YD, Zhang JB, Fan XH. Potential hepatic and renal toxicity induced by the biflavonoids from Ginkgo biloba. Chin J Nat Med. 2019 Sep;17(9):672-681. doi: 10.1016/S1875-5364(19)30081-0. PMID: 31526502. 17: Li M, Li B, Hou Y, Tian Y, Chen L, Liu S, Zhang N, Dong J. Anti-inflammatory effects of chemical components from Ginkgo biloba L. male flowers on lipopolysaccharide-stimulated RAW264.7 macrophages. Phytother Res. 2019 Apr;33(4):989-997. doi: 10.1002/ptr.6292. Epub 2019 Jan 29. PMID: 30693991. 18: Liu PK, Weng ZM, Ge GB, Li HL, Ding LL, Dai ZR, Hou XD, Leng YH, Yu Y, Hou J. Biflavones from Ginkgo biloba as novel pancreatic lipase inhibitors: Inhibition potentials and mechanism. Int J Biol Macromol. 2018 Oct 15;118(Pt B):2216-2223. doi: 10.1016/j.ijbiomac.2018.07.085. Epub 2018 Jul 21. PMID: 30009906. 19: Ghosh R, Chakraborty A, Biswas A, Chowdhuri S. Computer aided identification of potential SARS CoV-2 main protease inhibitors from diterpenoids and biflavonoids of Torreya nucifera leaves. J Biomol Struct Dyn. 2022 Apr;40(6):2647-2662. doi: 10.1080/07391102.2020.1841680. Epub 2020 Nov 3. PMID: 33140695; PMCID: PMC7663460. 20: Pathak RK, Baunthiyal M, Taj G, Kumar A. Virtual screening of natural inhibitors to the predicted HBx protein structure of Hepatitis B Virus using molecular docking for identification of potential lead molecules for liver cancer. Bioinformation. 2014 Jul 22;10(7):428-35. doi: 10.6026/97320630010428. PMID: 25187683; PMCID: PMC4135291.

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