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L9647

Sigma-Aldrich

Limonin

from citrus seeds, >90% (HPLC)

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Synonym(s):
Citrolimonin, Dictamnolactone, Evodin, Limonoic acid 3,19:16,17 dilactone, Obaculactone
Empirical Formula (Hill Notation):
C26H30O8
CAS Number:
Molecular Weight:
470.51
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

citrus seeds

Quality Level

assay

>90% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

InChI key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

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1 of 4

This Item
W504505PHL89379SML1787
vibrant-m

L9647

Limonin

vibrant-m

W504505

(S)-(−)-Limonene

vibrant-m

PHL89379

Limonin

vibrant-m

SML1787

Sinensetin

Quality Level

200

Quality Level

400

Quality Level

-

Quality Level

100

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

flavors and fragrances

application(s)

food and beverages

application(s)

-

biological source

citrus seeds

biological source

synthetic

biological source

-

biological source

-

assay

>90% (HPLC)

assay

≥95%

assay

≥95.0% (HPLC)

assay

≥98% (HPLC)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-8°C

General description

Limonin also known as citrolimonin and evodin, is a secondary plant metabolite present in citrus seeds at high concentrations. It is a derivative of limonoids.
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.

Application

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

Biochem/physiol Actions

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. It is an anti-carcinogenic agent, involved in the down-regulation Wingless-related integration site (Wnt) signaling pathway component in in vitro studies.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
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"
Fangyuan Gong et al.
Biochemical pharmacology, 80(2), 218-225 (2010-04-07)
Allograft rejection is a predominantly Th1 immune response. In this study, we showed that obaculactone, a natural compound derived from citrus fruit, prolonged skin graft survival in mice when treated after but not before transplantation. Furthermore, obaculactone inhibited alloantigen-specific production
Juanjuan Zhao et al.
Analytical and bioanalytical chemistry, 401(1), 289-296 (2011-05-17)
A liquid chromatographic-mass spectrometric (LC-MS) method has been developed and validated for simultaneous determination of dehydroevodiamine and limonin from Evodia rutaecarpa in rat plasma. After addition of the internal standard, domperidone, plasma samples were extracted by liquid-liquid extraction with ethyl
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)

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