L9647

Limonin

from citrus seeds, >90% (HPLC)

• Synonym(s): Citrolimonin, Dictamnolactone, Evodin, Limonoic acid 3,19:16,17 dilactone, Obaculactone
• 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

Properties

• 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

Description

General description

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.

Application

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
• as a reference standard in high-performance liquid chromatography (HPLC) system[4]

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.[5] 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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable