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Betulin

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-B3007

  • Specification : 98%

  • CAS number : 473-98-3

  • Formula : C30H50O2

  • Molecular Weight : 442.72

  • PUBCHEM ID : 72326

  • Volume : 25mg

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Catalogue Number

BF-B3007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

442.72

Appearance

White crystalline powder

Botanical Source

Xanthoceras sorbifolium,Ligustrum lucidum,Paeonia suffruticosa,Trigonella foenum-graecum,Ziziphus jujuba var. spinosa

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)CO

Synonyms

Betuline/Lup-20(30)-ene-3b,28-diol/TROCHOL/3b-Lup-20(29)-ene-3,28-diol/Betulin/BETULOL/(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(1-propen-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol/(3β)-Lup-20(29)-ene-3,28-diol/Lup-20(29)-ene-3b,28-diol/betula camphor/BETULINOL/(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-ol/Lup-20(29)-ene-3,28-diol, (3β)-/Lup-20(30)-ene-3β,28-diol

IUPAC Name

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol

Density

1.0±0.1 g/cm3

Solubility

Methanol; Petroleum ether

Flash Point

210.9±17.2 °C

Boiling Point

522.3±23.0 °C at 760 mmHg

Melting Point

256-257 °C(lit.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:473-98-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

28518138

Abstract

Continued oxidative stress can lead to chronic inflammation, which in turn could mediate most chronic diseases including cancer. Nuclear factor erythroid 2-related factor (Nrf2), a critical transcriptional activator for antioxidative responses, has envolved to be an attractive drug target for the treatment or prevention of human diseases. In the present study, we investigated the effects and mechanisms of betulin on Nrf2 activation and its involvement in the lipopolysaccharide (LPS)-triggered inflammatory system. In macrophages, betulin activated the Nrf2 signaling pathway and increased Nrf2-targeted antioxidant and detoxifying enzymes, including NADPH, quinine oxidoreductase 1 (NQO1), heme oxygenase-1 (HO-1), γ-glutamyl cysteine synthetase catalytic subunit (GCLC) and modifier subunit (GCLM) in a dose and time dependent manner. Importantly, we found betulin-induced activation of Nrf2 is AMPK/AKT/GSK3β dependent, as pharmacologically inactivating AMPK blocked the activating effect of betulin on AKT, GSK3β and Nrf2. Furthermore, betulin attenuated LPS-induced inflammatory mediators (iNOS and COX-2) and MAPK inflammatory signaling pathway. The effect of betulin on HO-1 and NQO1 upregulation, iNOS and COX-2 the downregulation, and survival time extension was largely weakened when Nrf2 was depleted in vitro and in vivo. Our results demonstrate that the AMPK/AKT/Nrf2 pathways are essential for the anti-inflammatory effects of betulin in LPS-stimulated macrophages and endotoxin-shocked mice.

Title

Betulin Exhibits Anti-Inflammatory Activity in LPS-stimulated Macrophages and Endotoxin-Shocked Mice Through an AMPK/AKT/Nrf2-dependent Mechanism

Author

Xinxin Ci 1 , Junfeng Zhou 2 , Hongming Lv 1 , Qinlei Yu 1 , Liping Peng 1 , Shucheng Hua 1

Publish date

2017 May 18

PMID

30119266

Abstract

Betulin is a phenolic flavonoid which has been reported to possess a mass of pharmacological properties, especially anti-inflammatory activity. The purpose of this study was to explore the protective effects and possible mechanism of betulin against lipopolysaccharide/D-galactosamine (LPS/D-Gal)-induced acute liver injury. D-Gal and LPS were intraperitoneally injected to develop acute liver injury animal model. Betulin (2, 4 or 8 mg/kg) were given 1 h before LPS/D-Gal instillation. Liver tissues and plasma samples were collected 9 h after LPS/D-Gal were given. The results indicated that betulin dramatically decreased liver pathologic changes, myeloperoxidase (MPO) activity, serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels. Simultaneously, the levels of interleukin (IL-1β) and tumor necrosis factor (TNF-α) in serum and liver tissues were both attenuated by betulin. Besides, betulin suppressed NF-κB pathway activation in a dose-dependently manner. Betulin increased the expression of PPAR-γ in a dose-dependent manner. In conclusion, all these results revealed that betulin could possess potential therapeutic effect for LPS/D-Gal-induced acute liver injury.

KEYWORDS

Acute liver injury; Betulin; D-galactosamine; Lipopolysaccharide; NF-κB.

Title

Betulin Inhibits lipopolysaccharide/D-galactosamine-induced Acute Liver Injury in Mice Through Activating PPAR-γ

Author

Guang-Meng Xu 1 , Tao Zan 2 , Hong-Yan Li 2 , Jin-Feng Han 2 , Zhong-Min Liu 2 , Ju Huang 2 , Li-Hua Dong 3 , Hai-Na Zhang 4

Publish date

2018 Oct

PMID

29022515

Abstract

This review highlights the multiple properties of the birch bark-derived pentacyclic triterpene betulin with special focus on its pharmacological activity in cancer and inflammation. While less well characterized compared to its hydrophilic derivative, betulinic acid, it exhibits potent anticancer activity described in many publications. Indeed, underinvestigated are its immunomodulatory functions in inflammatory diseases that appeared to enhance innate immune cell activities in an adjuvant-like fashion towards an interleukin-12 driven antitumor immunity. Herein, we like to emphasize the simultaneous and dual function of betulin on the basis of recent investigations of the tumor microenvironment and enlighten the potential use of betulin in the control of inflammation-associated carcinogenesis.

KEYWORDS

Pentacyclic triterpene; betulin; cytostatic; dendritic cell; immunomodulation; inflammation-associated carcinogenesis..

Title

Immunopharmacological Activity of Betulin in Inflammation-associated Carcinogenesis

Author

Anja Schwiebs 1 , Heinfried H Radeke 1

Publish date

2018


Description :

Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.