Limonin

Alias: Citro; Evodin; Limonine; Dictamnolactone; NSC36508; Limonin; NSC-36508; NSC 36508; Obaculactone;

Cat No.:V0734 Purity: ≥98%

COA Product Data Instructions for use SDS

Limonin Chemical Structure CAS No.: 1180-71-8
Product category: HIV Protease

This product is for research use only, not for human use. We do not sell to patients.

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1g
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Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Limonin (also known as NSC-36508; Obaculactone; limonoate D-ring-lactone and limonoic acid di-delta-lactone), a naturally occurring limonoid, is a hexacyclic triterpenoid isolated in citrus fruits and other plants, which has antivirus and antitumor ability. It is a crystalline, white, bitter substance. It belongs to the chemical class of substances called furanolactones. According to reports, extracts from citrus seeds possess antiviral qualities that prevent retroviruses such as HIV-1 and HTLV-I from replicating. Limonin has also been shown to have neuroprotective properties.

Biological Activity I Assay Protocols (From Reference)

Targets

Human Endogenous Metabolite

ln Vitro

Limonin is a citrus fruit-enriched furanolactone with antitumor and antivirus properties. With an EC50 of 60 μM, limonin prevents human immunodeficiency virus-1 (HIV-1) from replicating in human peripheral blood mononuclear cells (PBMC). (Source: ) In vivo, limonin also demonstrates antinociceptive and anti-inflammatory properties. [/2] Limonin regulates apoptosis and Wnt signaling to effectively inhibit the growth of human hepatoma HepG2 cells.[3]

ln Vivo

Limonin demonstrated a 60% decrease in the tumor burden in female Syrian hamsters treated with DMBA, a drug that can cause tumors. It reduced 50% of the tumor mass and 20% of the tumor count. 0.05% limonin in the diet dramatically decreased (65%-92% inhibition) the incidence of colonic adenocarcinoma in male F344 rats treated with azoxymethane (AOM). Limonin therefore has chemopreventive effects on carcinogenesis that is chemically induced.

Cell Assay

Limonin inhibits HIV-1 replication in all cellular systems when it is cultivated in human peripheral blood mononuclear cells (PBMC) and monocytes/macrophages (M/M). In PBMC cells, this inhibition is dose-dependent and has an EC50 value of 60u μM. Limonin has the ability to induce apoptosis in human hepatoma HepG2 cells, as demonstrated by WB analysis of several apoptosis factors.

Animal Protocol

0.05% limonin in diet

Female Syrian hamsters and rats

References

[1]. Planta Med . 2003 Oct;69(10):910-3.

[2]. Planta Med . 1998 May;64(4):339-42.

[3]. J Nat Sci Biol Med . 2013 Jan;4(1):126-33.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C26H30O8

Molecular Weight

470.51

Exact Mass

470.19

Elemental Analysis

C, 66.37; H, 6.43; O, 27.20

CAS #

1180-71-8

Related CAS #

1180-71-8

Appearance

Solid powder

SMILES

C[C@@]12CC[C@H]3[C@]([C@@]14[C@H](O4)C(=O)O[C@H]2C5=COC=C5)(C(=O)C[C@@H]6[C@@]37COC(=O)C[C@@H]7OC6(C)C)C

InChi Key

KBDSLGBFQAGHBE-MSGMIQHVSA-N

InChi Code

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

Chemical 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

Synonyms

Citro; Evodin; Limonine; Dictamnolactone; NSC36508; Limonin; NSC-36508; NSC 36508; Obaculactone;

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: ~44 mg/mL (~93.5 mM)

Water: <1 mg/mL

Ethanol: <1 mg/mL

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.1254 mL	10.6268 mL	21.2535 mL
	5 mM	0.4251 mL	2.1254 mL	4.2507 mL
	10 mM	0.2125 mL	1.0627 mL	2.1254 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Calculate Reset

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT02011789	Completed	Dietary Supplement: Citrus Limonoid Beverage Dietary Supplement: Placebo beverage	Hypercholesterolemia	USDA, Western Human Nutrition Research Center	April 2007	Not Applicable

Biological Data

Effect of Limonin on HepG2 cells viability - MTT assay Each Bar represents mean ±SD of six observations, a -Control Vs DMSO, 20, 40, 60, 80 and 100 μM 24 h, b -Control Vs DMSO, 20, 40, 60, 80 and 100 μM for 48 h. J Nat Sci Biol Med . 2013 Jan;4(1):126-33.

Levels of GSH in control and limonin treated HepG2 cells, Each bar represents mean SD of six observations, a -Group I Vs Group II & Group III, b -Group II Vs Group III. J Nat Sci Biol Med . 2013 Jan;4(1):126-33.

Microscopic image of control and limonin treated HepG2 cells. J Nat Sci Biol Med . 2013 Jan;4(1):126-33.
Western blotting analysis of Caspase-9 and Cyclin D1protein expression in control and limonin treated HepG2 cells. J Nat Sci Biol Med . 2013 Jan;4(1):126-33.