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Limonin(Evodin)

$45

  • Brand : BIOFRON

  • Catalogue Number : AV-P10079

  • Specification : 98%

  • CAS number : 1180-71-8

  • Formula : C26H30O8

  • Molecular Weight : 470.51

  • PUBCHEM ID : 179651

  • Volume : 1000mg

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Catalogue Number

AV-P10079

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

470.51

Appearance

Off-white crystalline powder

Botanical Source

Citrus limon/oranges and other citrus fruits (Citrus spp.). Also from other Rutaceae spp., e.g. Evodia, Phellodendron, Dictamnus and Luvunga spp.

Structure Type

Triterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(C2CC(=O)C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)C

Synonyms

Limonoic acid di-δ-lactone/8-(3-Furyl)decahydro-2,2,4a,8a-tetramethyl-11H,13H-oxireno[d]pyrano[4',3':3,3a]isobenzofuro[5,4-f][2]benzopyran-4,6,13(2H,5aH)-trione/(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydrooxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(1H,6H,8aH)-trione/Limonoic acid 3,19:16,17 dilactone/1H,3H-Oxireno[c]pyrano[4'',3'':2',3']furo[3',4':5,6]naphtho[1,2-d]pyran-3,8,10(6H,9aH)-trione, 12-(3-furanyl)decahydro-6,6,8a,12a-tetramethyl-, (4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)/LiMone/DICTAMNOLACTONE/CITROLIMONIN/Limonin/Evodine/Limonoic Acid Di-d-lactone/LIMONINE/(4aS,6aR,8aR,8bR,9aS,12R,12aS,14aR,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione/EVODIN/OBACULACTONE/(4aS,6aR,8aR,8bR,9aS,12S,12aS,14aR,14bR)-12-(3-Furyl)-6,6,8a,12a-tetramethyldecahydro-3H-oxireno[d]pyrano[4',3':3,3a][2]benzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione

IUPAC Name

(1R,2R,7S,10R,13R,14R,16S,19S,20S)-19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,12,17-trione

Density

1.4±0.1 g/cm3

Solubility

Methanol; Acetontrile; Chloroform; DMSO; DMF

Flash Point

358.0±31.5 °C

Boiling Point

668.4±55.0 °C at 760 mmHg

Melting Point

298ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:1180-71-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

9619117

Abstract

Antinociceptive and anti-inflammatory effects of limonin isolated from the dried fruits of Evodia rutaecarpa var. bodinieri were investigated. Oral administration of 30 or 100 mg/kg limonin significantly decreased the frequency of licking and biting behavior within a unit of time at the late phase without affecting that of the early phase in the formalin test. Limonin inhibited the rise of vascular permeability induced by acetic acid and the increase of paw edema induced by carrageenin. Limonin also showed inhibitory effects on bradykinin-induced paw edema and arachidonic acid-induced ear swelling. These results suggest that limonin possesses an antinociceptive effect and the effect may be accompanied by an anti-inflammatory action, and that the antinociceptive activity in Evodiae Fructus is partially attributable to limonin.

Title

Antinociceptive and Anti-Inflammatory Activities of Limonin Isolated From the Fruits of Evodia Rutaecarpa Var. Bodinieri

Author

H Matsuda 1 , M Yoshikawa, M Iinuma, M Kubo

Publish date

1998 May

PMID

32197606

Abstract

Background: Ovarian cancer therapy generally involves systemic chemotherapy with anticancer drugs; however, chemotherapy with a platinum-based drug has often been shown to cause adverse reactions and drug resistance in ovarian cancer patients. Evodia rutaecarpa (ER) reportedly shows anticancer activity against various types of cancer cells. However, the effects of ER have not yet been fully uncovered in ovarian cancer.
Methods: In the present study, we investigated the anticancer effects of an ER extract and its components against the ovarian cancer cell lines SKOV-33, A2780, RMUG-S and a cisplatin-resistant SKOV-3 cell line (CisR SKOV-3). Cell viability and colony formation assays along with subcellular fractionation analysis, immunoblotting, and immunofluorescence staining were performed.
Results: ER treatment led to a significant reduction in the viability of SKOV-3 cells. Moreover, limonin, a compound found in ER, reduced the viability of both serous-type (SKOV-3 and A2780) and mucinous-type (RMUG-S) ovarian cancer cells by inducing apoptosis via activation of the p53 signaling pathway. Furthermore, limonin reversed the drug resistance through activation of apoptosis in CisR SKOV-3.
Conclusion: Taken together, our findings suggest that limonin contributes to the anti-ovarian cancer effects of ER by inducing apoptosis via activation of the p53 signaling pathway.

KEYWORDS

Apoptosis; Cisplatin resistance; Evodia rutaecarpa; Limonin; p53.

Title

Role of Limonin in Anticancer Effects of Evodia Rutaecarpa on Ovarian Cancer Cells

Author

Jae Ryul Bae 1 , Wook Ha Park 1 , Dong Hoon Suh 1 , Jae Hong No 1 , Yong Beom Kim 1 , Kidong Kim 2

Publish date

2020 Mar 20

PMID

21573727

Abstract

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 acetate and separated on an Apollo C(18) column (250 mm × 4.6 mm, 5 μm), with methanol-0.01% formic acid water (60:40, v/v) as mobile phase, within a runtime of 12.0 min. The analytes were detected without interference in the selected ion monitoring (SIM) mode with positive electrospray ionization. The linear range was 1.0-500 ng mL(-1) for dehydroevodiamine and 2.0-1,000 ng mL(-1) for limonin, with lower limits of quantitation of 1.0 and 2.0 ng mL(-1), respectively. Intra-day and inter-day precision were within 6.0% and 10.9%, respectively, for both analytes, and the accuracy (relative error, RE, %) was less than 4.8% and 6.5%, respectively. The validated method was successfully applied to a comparative pharmacokinetic study of dehydroevodiamine and limonin in rat plasma after oral administration of dehydroevodiamine, limonin, and an aqueous extract of Evodiae fructus. The results indicated there were obvious differences between the pharmacokinetic behavior after oral administration of an aqueous extract of Evodiae fructus compared with single substances.

Title

A Sensitive Liquid Chromatographic-Mass Spectrometric Method for Simultaneous Determination of Dehydroevodiamine and Limonin From Evodia Rutaecarpa in Rat Plasma

Author

Juanjuan Zhao 1 , Xiao Han, Xu Zhao, Chao Wang, Qing Li, Xiaohui Chen, Kaishun Bi

Publish date

2011 Jul


Description :

Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.IC50 Value: Target: HIV; anticancerLimonin is a triterpenoid aglycone that is a bitter principle of citrus fruits. Limonin is chemically induced carcinogenesis inhibitor and HIV-1 replication inhibitor. Limonin has anti-proliferative, proapoptotic activity on several cancer cell lines and inhibits azoxymethane-induced colon cancer in rats. Limonin also inhibits HIV-1 replication in culturedf monocytes, macrophages, and mononuclear cells, perhaps by inhibition of HIV-1 protease activity.