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L9647

Sigma-Aldrich

Limonin

from citrus seeds, >90% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C26H30O8
Numéro CAS:
1180-71-8
Poids moléculaire :
470.51
Numéro MDL:
MFCD00075922
Code UNSPSC :
12352205
ID de substance PubChem :
24896458
Nomenclature NACRES :
NA.25

Source biologique

citrus seeds

Niveau de qualité

200

Essai

>90% (HPLC)

Forme

powder

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

KBDSLGBFQAGHBE-MSGMIQHVSA-N

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Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
079M4897V
016M4769V
062M4829
021M4804
109K4773

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Consulter la Bibliothèque de documents

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
Yang Zhao et al.
Journal of pharmaceutical and biomedical analysis, 48(4), 1230-1236 (2008-10-22)
A simple, sensitive and accurate HPLC-DAD method was developed for simultaneous determination of wuchuyuamide-I, quercetin, limonin, evodiamine and rutaecarpine in Evodia rutaecarpa that has been widely used as one of the traditional Chinese medicines (TCMs). Chromatographic separations were performed on
Raju Lal Bhardwaj et al.
Critical reviews in food science and nutrition, 51(6), 563-570 (2011-09-21)
The post-harvest shelf life of maximum of fruits and vegetables is very limited due to their perishable nature. In India more then 20-25 percent of fruits and vegetables are spoiled before utilization. Despite being the world's second largest producer of
Kotamballi N Chidambara Murthy et al.
Journal of agricultural and food chemistry, 59(6), 2314-2323 (2011-02-23)
The current study was an attempt to elucidate the mechanism of human colon cancer cell proliferation inhibition by limonin and limonin glucoside (LG) isolated from seeds of Citrus reticulata. The structures of purified compounds were confirmed by NMR and quantified
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