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L9647

Limonin

from citrus seeds, >90% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H30O8
CAS Number:
1180-71-8
Molecular Weight:
470.51
NACRES:
NA.25
PubChem Substance ID:
24896458
UNSPSC Code:
12352205
MDL number:
MFCD00075922
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biological source

citrus seeds

Quality Segment

200

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

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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