545-47-1 Usage
Description
Lupeol is a kind of novel anti-inflammatory and anti-cancer dietary triterpene that can be found in white cabbage, green pepper, strawberry, olive, mangoes and grapes. In recent years, much progress has been made on the application of this molecule for clinical treatment of various kind of disorders. On the one hand, it has been extensively studied that it is capable of inhibiting inflammation under both in vitro and in animal models. Studies have shown that Lupeol is a multi-target agent during its anti-inflammation effect, targeting on many key molecular pathways involving nuclear factor kappa B (NFκB), cFLIP, Fas, Kras, phosphatidylinositol-3-kinase (PI3K)/Akt and Wnt/β-catenin. On the other hand, Lupeol has strong anti-tumor effect during treatment of various cancer types such as prostate, skin, pancreatic and breast cancer. The anti-tumor effect might be related to its potential to modulate important signaling pathways such as nuclear factor kappa B (NFκB) and the phosphatidylinositol 3-kinase [PI3K] /Akt (protein kinase B pathway), which are crucial during tumorigenesis.
References
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2764818/
https://en.wikipedia.org/wiki/Lupeol
Chemical Properties
White powder
Uses
Different sources of media describe the Uses of 545-47-1 differently. You can refer to the following data:
1. antineoplastic
2. Abundant plant triterpene. Occurs in the skin of lupin seeds, in circle, in the latex of fig trees and of rubber plants. It was detected in cocoons of Bombyx mori.
3. Lupeol was used as reference standard in method development and validation of lupeol from Vernonia Cinerea using HPLC method. It has been used as a standard for the identification and quantification of triterpenoids in blueberry cuticular wax by GC.
Definition
ChEBI: A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in m
ny edible fruits and vegetables.
General Description
Lupeol is a novel anti-cancer and anti-inflammatory dietary triterpene. They help in stabilizing phospholipid bilayers in plant cell membranes. In general, this group contains 28-29 carbons along with carbon-carbon double bonds, usually one in the sterol nucleus and at times a second in the alkyl side chain.
Check Digit Verification of cas no
The CAS Registry Mumber 545-47-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 5 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 545-47:
(5*5)+(4*4)+(3*5)+(2*4)+(1*7)=71
71 % 10 = 1
So 545-47-1 is a valid CAS Registry Number.
InChI:InChI=1/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
545-47-1Relevant articles and documents
Pentacyclic triterpenes and naphthoquinones from Euclea divinorum
Mebe, Paul P.,Cordell, Geoffrey A.,Pezzuto, John M.
, p. 311 - 313 (1998)
Phytochemical studies on Euclea divinorum have resulted in the isolation of lupeol, lupene, betulin, 7-methyljuglone, isodiospyrin, shinalone, catechin and 3β-(5-hydroxyferuloyl)lup-20(30)-ene. The structures were assigned on the basis spectral and chemical studies and the compounds were evaluated for their cytotoxic activity.
Antibacterial activity of naphthoquinones and triterpenoids from Euclea natalensis root bark
Weigenand, Oliver,Hussein, Ahmed A.,Lall, Namrita,Meyer, Jacobus J. M.
, p. 1936 - 1938 (2004)
Phytochemical studies of an ethanolic extract of Euclea natalensis root bark afforded two new compounds, octahydroeuclein (1) and 20(29)-lupene-3β- isoferulate (2), in addition to three known compounds, shinanolone (3), lupeol, and betulin. The chemical structures of 1 and 2 were determined by spectroscopic means. Shinanolone (3) showed inhibitory activity against Gram-positive bacterial strains and a drug-sensitive strain of Mycobacterium tuberculosis at a concentration of 0.1 mg/mL.
Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase
Chen, Dongyin,Xu, Fengguo,Zhang, Pu,Deng, Jie,Sun, Hongbin,Wen, Xiaoan,Liu, Jun
, (2017/10/20)
A practical synthesis of α-amyrin (1), β-amyrin (2), and lupeol (3) was accomplished in total yields of 32, 42, and 40% starting from easily available ursolic acid (4), oleanolic acid (5), and betulin (6), respectively. Remarkably, these three natural pentacyclic triterpenes exhibited potential inhibitory activity against human oxidosqualene cyclase.
Lupeol-3-O-decanoate, a new triterpene ester from Cadaba farinosa Forssk. growing in Saudi Arabia
Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.
, p. 5297 - 5302 (2013/12/04)
A new triterpene ester (1) together with eight known compounds (2-9) were isolated from the leaves of Cadaba farinosa Forssk. Their chemical structures were established on the basis of physical, chemical, and spectroscopic methods (IR, 1D and 2D NMR, and mass spectral analyses) to be: lupeol-3-O-decanoate (1), lupeol (2), β-sitosterol (3), ursolic acid (4), 12-aminododecanoic (5), dillenetin-3-O-β-d-glucopyranoside (6), stachydrine (7), 3-hydroxy-stachydrine (8), and quercetin-3-O-β-d-glucopyranoside (9). That is the first report for the isolation of compound 5 from a plant source. Compounds 5, 6, and 9 were evaluated for their antioxidant activity.
