Betulin - CAS 473-98-3
Catalog number:
473-98-3
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C30H50O2
Molecular Weight:
442.7
COA:
Inquire
Targets:
pro-inflammatory cytokines
Description:
Betulin can be found in the barks of Betula alba L. Its nanoparticles powder show an excellent hypoglycemic effect compared with raw Betulin. Betulin alleviated LPS-induced acute lung injury. Besides, Betulin inhibited pro-inflammatory cytokines expression and NF-κB signaling activation through STAT3 signaling.
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Purity:
≥98%
Appearance:
Solid powder
Synonyms:
BETULINOL;BETULOL;LUP-20(29)-ENE-3,28-DIOL,(3B);LUP-20[29]-ENE3B,28-DIOL;LUP-20(29)-ENE-3BETA,28-DIOL;LUP-20(29)-EN-3,28-DIOL;TROCHOL
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
Antineoplastic/anti-HIV
Quality Standard:
Enterprise standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Quantity:
Milligrams-Grams
Melting Point:
251-255 ºC
InChIKey:
XQHSXWXRLYHKSF-VFXNRHIGSA-N
InChI:
1S/C28H46O2/c1-18(2)21-10-13-28(17-29)15-14-26(4)22(24(21)28)6-7-23-25(3)11-9-20(30)16-19(25)8-12-27(23,26)5/h19-24,29-30H,1,6-17H2,2-5H3/t19-,20-,21-,22+,23+,24+,25-,26+,27+,28+/m0/s1
Canonical SMILES:
O[C@H]1CC[C@@]2(C)[C@](CC[C@]3(C)[C@]2([H])CC[C@@]4([H])[C@]3(CC[C@]5(CO)[C@]4([H])[C@H](C(C)=C)CC5)C)([H])C1(C)C
1.Assessment of cytochrome P450 inhibition and induction potential of lupeol and betulin in rat liver microsomes.
Seervi M, Lotankar S, Barbar S, Sathaye S. Drug Metabol Personal Ther. 2016 Mar 9. pii: /j/dmdi.ahead-of-print/dmpt-2015-0043/dmpt-2015-0043.xml. doi: 10.1515/dmpt-2015-0043. [Epub ahead of print]
BACKGROUND: Lupeol and betulin are triterpenoids that are majorly found in dietary substances. The aim of present study was to investigate the inhibition and induction potential of lupeol and betulin on cytochrome P450 (CYP)1A2, CYP2C11, CYP2D6, and CYP3A2 activities in rat liver microsomes.
2.Betulin Derivatives Effectively Suppress Inflammation in Vitro and in Vivo.
Laavola M1, Haavikko R2, Hämäläinen M1, Leppänen T1, Nieminen R1, Alakurtti S3, Moreira VM2, Yli-Kauhaluoma J2, Moilanen E1. J Nat Prod. 2016 Feb 26;79(2):274-80. doi: 10.1021/acs.jnatprod.5b00709. Epub 2016 Jan 14.
Betulin is a pharmacologically active triterpenoid found in the bark of the birch tree (Betula sp. L.). Betulin and betulinic acid are structurally related to anti-inflammatory steroids, but little is known about their potential anti-inflammatory properties. In the present study, the inflammatory gene expression and the anti-inflammatory properties of betulin, betulinic acid, and 16 semisynthetic betulin derivatives were investigated. Betulin derivatives 3, 4, and 5 selectively inhibited the expression of the inducible nitric oxide synthase (iNOS) in a post-transcriptional manner. They also inhibited nitric oxide (NO) production but had no effect on the other inflammatory factors studied. More interestingly, a new anti-inflammatory betulin derivative 9 with a wide-spectrum anti-inflammatory activity was discovered. Compound 9 was found to suppress the expression of cytokines interleukin-6 (IL-6) and monocyte chemotactic protein-1 (MCP-1), as well as that of prostaglandin synthase-2 (COX-2) in addition to iNOS.
3.Pharmacological research on natural substances in Latvia: Focus on lunasin, betulin, polyprenol and phlorizin.
Muceniece R1, Namniece J2, Nakurte I3, Jekabsons K2, Riekstina U2, Jansone B4. Pharmacol Res. 2016 Apr 21. pii: S1043-6618(16)30007-X. doi: 10.1016/j.phrs.2016.03.040. [Epub ahead of print]
In this concise review the current research in plant bioactive compound studies in Latvia is described. The paper summarizes recent studies on substances from edible plants (e.g., cereals and apples) or their synthetic analogues, such as peptide lunasin, as well as substances isolated from inedible plants (e.g., birch and conifer), such as pentacyclic triterpenes (e.g., betulin, betulinic acid, and lupeol) and polyprenols. Latvian researchers have been first to demonstrate the presence of lunasin in triticale and oats. Additionally, the impact of genotype on the levels of lunasin in cereals was shown. Pharmacological studies have revealed effects of lunasin and synthetic triterpenes on the central nervous system in rodents. We were first to show that synthetic lunasin causes a marked neuroleptic/cataleptic effect and that betulin antagonizes bicuculline-induced seizures (a GABA A receptor antagonist). Studies on the mechanisms of action showed that lunasin binds to dopamine D1 receptors and betulin binds to melanocortin and gamma-aminobutyric acid A receptors therefore we suggest that these receptors play an essential role in lunasin's and betulin's central effects.
4.Isostructurality Among 5 Solvatomorphs of Betulin: X-Ray Structure and Characterization.
Yang D1, Gong N1, Zhang L1, Lu Y2. J Pharm Sci. 2016 Apr 26. pii: S0022-3549(16)00443-3. doi: 10.1016/j.xphs.2016.03.015. [Epub ahead of print]
Betulin (BE), a triterpene found in many plant species, has recently attracted the attention of researchers because of its important physiological and pharmacological properties, such as anti-HIV and anticancer activities. Studies have revealed the solvatomorphism of BE (I with dimethyl sulfoxide and III with ethanol, named by author), which means more solvatomorphs may be obtained when different solvents are used during crystallization. After solid-form screening tests, 3 new solvatomorphs of BE with methanol (II), n-propanol (IV), and isopropanol (V) were obtained. In this work, 5 BE solvatomorphs were characterized by X-ray powder diffractometric, thermogravimetric, and Fourier transform infrared spectroscopic analyses. Single-crystal X-ray diffraction was used to analyze the X-ray structures of the compounds, and all 5 solvatomorphs were proven to be isostructral. Change in the crystal symmetry, intermolecular arrangements, stoichiometry, and hydrogen bonding interactions of the solvatomorphs resulted from solvent incorporation to the solvates.
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CAS 473-98-3 Betulin

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