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Documenti fondamentali

L9647

Sigma-Aldrich

Limonin

from citrus seeds, >90% (HPLC)

Sinonimo/i:

Citrolimonin, Dictamnolactone, Evodin, Limonoic acid 3,19:16,17 dilactone, Obaculactone

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5 MG
219,00 €

About This Item

Formula empirica (notazione di Hill):
C26H30O8
Numero CAS:
Peso molecolare:
470.51
Numero MDL:
Codice UNSPSC:
12352205
ID PubChem:
NACRES:
NA.25

219,00 €


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Origine biologica

citrus seeds

Livello qualitativo

Saggio

>90% (HPLC)

Stato

powder

applicazioni

metabolomics
vitamins, nutraceuticals, and natural products

Temperatura di conservazione

2-8°C

Stringa SMILE

CC1(C)O[C@H]2CC(=O)OC[C@]23[C@H]4CC[C@@]5(C)[C@@H](OC(=O)[C@H]6O[C@@]56[C@]4(C)C(=O)C[C@@H]13)c7ccoc7

InChI

1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1
KBDSLGBFQAGHBE-MSGMIQHVSA-N

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Descrizione generale

Limonin also known as citrolimonin and evodin, is a secondary plant metabolite present in citrus seeds at high concentrations.[1] It is a derivative of limonoids.[2]
Limonin may be used in assays to quantify limonin in citrus products. It may also be used in other assays as a control, standard, or competitor or in studies on the physiology, metabolism, and biosynthesis of limonin.

Applicazioni

Limonin has been used:
  • to treat human peripheral blood mononuclear cells (PBMCs) to test its effect on human immunodeficiency virus (HIV) replication[3]
  • to test its effects as an anti-osteoporosis agent in osteoblastogenesis activity in MC3T3-E1 cells and ovariectomized (OVX) rat model[4]
  • as a reference standard in high-performance liquid chromatography (HPLC) system[5]

Azioni biochim/fisiol

Limonin exerts its anti-inflammatory activity by downregulating signal transducer and activator of transcription 3/ microRNA-214 (STAT3/miR-214) signaling pathway in Ulcerative colitis (UC) condition.[6] It is an anti-carcinogenic agent, involved in the down-regulation Wingless-related integration site (Wnt) signaling pathway component in in vitro studies.[2]
Limonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. It has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. It also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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Lilibeth Dagulo et al.
Journal of food science, 75(2), C199-C207 (2010-05-25)
The effects due to Candidatus Liberibacter infection, commonly called citrus greening or Huanglongbing (HLB), on volatile and nonvolatile components of orange juices, OJ, were examined using GC-MS and high-performance liquid chromatography (HPLC). HLB symptomatic, asymptomatic, and control "Hamlin" and "Valencia"
Yong-Long Han et al.
Toxicology in vitro : an international journal published in association with BIBRA, 25(8), 1828-1833 (2011-10-18)
Among the various possible causes for drug interactions, pharmacokinetic factors such as inhibition of drug-metabolizing enzymes and transporters, especially cytochrome P450 (CYP) isoenzymes and P-glycoprotein (P-gp), are regarded as the most frequent and clinically important. Limonin is a widely used
Wooki Kim et al.
The Journal of nutrition, 139(5), 1042-1048 (2009-03-27)
Phytochemicals may reduce chronic inflammation and cancer risk in part by modulating T-cell nuclear factor-kappaB (NF-kappaB) activation. Therefore, we examined the effects of curcumin (Cur) and limonin (Lim) feeding on NF-kappaB-dependent CD4(+) T-cell proliferation. DO11.10 transgenic mice (n = 5-7)
Anne M Slisz et al.
Journal of proteome research, 11(8), 4223-4230 (2012-06-16)
Huanglongbing (HLB), considered the most serious citrus disease in the world, is associated with the nonculturable bacterium 'Candidatus Liberibacter asiaticus' (Las). Infection of citrus by this pathogen leads to reduced plant vigor and productivity, ultimately resulting in death of the
Shunming Fan et al.
Molecules (Basel, Switzerland), 24(20) (2019-10-17)
Limonin is a natural tetracyclic triterpenoid compound, which widely exists in Euodiarutaecarpa (Juss.) Benth., Phellodendronchinense Schneid., and Coptischinensis Franch. Its extensive pharmacological effects have attracted considerable attention in recent years. However, there is no systematic review focusing on the pharmacology

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