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MedKoo Cat#: 540268 | Name: Limonin glucoside
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Limonin glucoside is found in citrus fruits. It induces apoptosis in colon adenocarcinoma cells, inhibits expression of HIV-1 and HTLV-1 in infected cells, and exhibits larvicidal activity against species of Aedes.

Chemical Structure

Limonin glucoside
Limonin glucoside
CAS#123564-61-4

Theoretical Analysis

MedKoo Cat#: 540268

Name: Limonin glucoside

CAS#: 123564-61-4

Chemical Formula: C32H42O14

Exact Mass: 650.2575

Molecular Weight: 650.67

Elemental Analysis: C, 59.07; H, 6.51; O, 34.42

Price and Availability

Size Price Availability Quantity
5mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
CCRIS 6986; CCRIS6986; CCRIS-6986; Limonin glucoside
IUPAC/Chemical Name
(3'S,4aR,6aS,8aS,9S,10S,12aS,12bR)-10-((S)-furan-3-yl(((2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-6,6,8a,10-tetramethyl-3,8-dioxodecahydro-1H,3H,6H-spiro[naphtho[1',2':3,4]furo[3,2-c]pyran-9,2'-oxirane]-3'-carboxylic acid
InChi Key
FYIKIBQJAJRKQM-BPHZWCSFSA-N
InChi Code
InChI=1S/C32H42O14/c1-28(2)17-9-18(34)30(4)16(31(17)13-42-20(35)10-19(31)45-28)5-7-29(3,32(30)25(46-32)26(39)40)24(14-6-8-41-12-14)44-27-23(38)22(37)21(36)15(11-33)43-27/h6,8,12,15-17,19,21-25,27,33,36-38H,5,7,9-11,13H2,1-4H3,(H,39,40)/t15-,16+,17+,19+,21+,22+,23+,24-,25+,27-,29-,30+,31+,32-/m0/s1
SMILES Code
OC[C@@H]1O[C@@H](O[C@H]([C@]2([C@]3([C@]4(C(C[C@@H]5C(C)(O[C@@H]6CC(OC[C@@]56[C@@H]4CC2)=O)C)=O)C)[C@H](O3)C(O)=O)C)c7ccoc7)[C@H](O)[C@H](O)[C@@H]1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Limonin glucoside is found in citrus fruits.
In vitro activity:
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 IC50 value of 54.74 and 37.39 μM was observed for limonin and LG, respectively at 72 h. Following confirmation of proliferation inhibition, pattern of DNA fragmentation and activation of caspase-3 of the cells treated with limonoids suggest involvement of apoptosis. Reference: J Agric Food Chem. 2011 Mar 23;59(6):2314-23. https://pubmed.ncbi.nlm.nih.gov/21338095/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 650.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Chidambara Murthy KN, Jayaprakasha GK, Kumar V, Rathore KS, Patil BS. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. J Agric Food Chem. 2011 Mar 23;59(6):2314-23. doi: 10.1021/jf104498p. Epub 2011 Feb 21. PMID: 21338095.
In vitro protocol:
1. Chidambara Murthy KN, Jayaprakasha GK, Kumar V, Rathore KS, Patil BS. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. J Agric Food Chem. 2011 Mar 23;59(6):2314-23. doi: 10.1021/jf104498p. Epub 2011 Feb 21. PMID: 21338095.
In vivo protocol:
TBD
1: Chidambara Murthy KN, Jayaprakasha GK, Kumar V, Rathore KS, Patil BS. Citrus limonin and its glucoside inhibit colon adenocarcinoma cell proliferation through apoptosis. J Agric Food Chem. 2011 Mar 23;59(6):2314-23. doi: 10.1021/jf104498p. Epub 2011 Feb 21. PubMed PMID: 21338095. 2: Somasundaram S, Price J, Pearce K, Shuck R, Jayaprakasha GK, Patil B. Citrus limonin lacks the antichemotherapeutic effect in human models of breast cancer. J Nutrigenet Nutrigenomics. 2012;5(2):106-14. Epub 2012 Aug 17. PubMed PMID: 22907263. 3: Breksa AP 3rd, Manners GD. Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside. J Agric Food Chem. 2006 May 31;54(11):3827-31. PubMed PMID: 16719503. 4: Zunino SJ, Storms DH, Freytag TL, Adkins YC, Bonnel EL, Woodhouse LR, Breksa AP 3rd, Manners GD, Mackey BE, Kelley DS. Dietary supplementation with purified citrus limonin glucoside does not alter ex vivo functions of circulating T lymphocytes or monocytes in overweight/obese human adults. Nutr Res. 2016 Jan;36(1):24-30. doi: 10.1016/j.nutres.2015.10.011. Epub 2015 Oct 31. PubMed PMID: 26773778. 5: Breksa AP 3rd, Dragull K, Wong RY. Isolation and identification of the first C-17 limonin epimer, epilimonin. J Agric Food Chem. 2008 Jul 23;56(14):5595-8. doi: 10.1021/jf800473z. Epub 2008 Jun 20. PubMed PMID: 18564847. 6: Perez JL, Jayaprakasha GK, Valdivia V, Munoz D, Dandekar DV, Ahmad H, Patil BS. Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase. J Agric Food Chem. 2009 Jun 24;57(12):5279-86. doi: 10.1021/jf803712a. PubMed PMID: 19480426; PubMed Central PMCID: PMC2730739. 7: Breksa AP 3rd, Ibarra P Jr. Colorimetric method for the estimation of total limonoid aglycones and glucoside contents in citrus juices. J Agric Food Chem. 2007 Jun 27;55(13):5013-7. Epub 2007 Jun 2. PubMed PMID: 17542603. 8: Tian Q, Kent KD, Bomser JA, Schwartz SJ. Characterization of limonin glucoside metabolites from human prostate cell culture medium using high-performance liquid chromatography/electrospray ionization mass spectrometry and tandem mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(24):3099-104. PubMed PMID: 15565733. 9: Braddock RJ, Bryan CR. Extraction parameters and capillary electrophoresis analysis of limonin glucoside and phlorin in citrus byproducts. J Agric Food Chem. 2001 Dec;49(12):5982-8. PubMed PMID: 11743796. 10: Miller EG, Gonzales-Sanders AP, Couvillon AM, Wright JM, Hasegawa S, Lam LK. Inhibition of hamster buccal pouch carcinogenesis by limonin 17-beta-D-glucopyranoside. Nutr Cancer. 1992;17(1):1-7. PubMed PMID: 1574440. 11: Kim J, Jayaprakasha GK, Patil BS. Limonoids and their anti-proliferative and anti-aromatase properties in human breast cancer cells. Food Funct. 2013 Feb;4(2):258-65. doi: 10.1039/c2fo30209h. PubMed PMID: 23117440. 12: El-Readi MZ, Hamdan D, Farrag N, El-Shazly A, Wink M. Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines. Eur J Pharmacol. 2010 Jan 25;626(2-3):139-45. doi: 10.1016/j.ejphar.2009.09.040. Epub 2009 Sep 24. PubMed PMID: 19782062. 13: Jayaprakasha GK, Dandekar DV, Tichy SE, Patil BS. Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra. J Sep Sci. 2011 Jan;34(1):2-10. doi: 10.1002/jssc.201000644. Epub 2010 Nov 26. PubMed PMID: 21171170. 14: Raithore S, Bai J, Plotto A, Manthey J, Irey M, Baldwin E. Electronic Tongue Response to Chemicals in Orange Juice that Change Concentration in Relation to Harvest Maturity and Citrus Greening or Huanglongbing (HLB) Disease. Sensors (Basel). 2015 Dec 2;15(12):30062-75. doi: 10.3390/s151229787. PubMed PMID: 26633411; PubMed Central PMCID: PMC4721708. 15: Ren W, Xin SK, Han LY, Zuo R, Li Y, Gong MX, Wei XL, Zhou YY, He J, Wang HJ, Si N, Zhao HY, Yang J, Bian BL. Comparative metabolism of four limonoids in human liver microsomes using ultra-high-performance liquid chromatography coupled with high-resolution LTQ-Orbitrap mass spectrometry. Rapid Commun Mass Spectrom. 2015 Nov 15;29(21):2045-56. doi: 10.1002/rcm.7365. PubMed PMID: 26443405. 16: Manners GD, Jacob RA, Breksa AP 3rd, Schoch TK, Hasegawa S. Bioavailability of citrus limonoids in humans. J Agric Food Chem. 2003 Jul 2;51(14):4156-61. PubMed PMID: 12822961. 17: Yin T, Yang G, Ma Y, Xu B, Hu M, You M, Gao S. Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B). J Ethnopharmacol. 2015 Aug 22;172:195-201. doi: 10.1016/j.jep.2015.06.019. Epub 2015 Jun 20. PubMed PMID: 26099633; PubMed Central PMCID: PMC4541799. 18: Yu J, Dandekar DV, Toledo RT, Singh RK, Patil BS. Supercritical fluid extraction of limonoid glucosides from grapefruit molasses. J Agric Food Chem. 2006 Aug 9;54(16):6041-5. PubMed PMID: 16881714. 19: Dandekar DV, Jayaprakasha GK, Patil BS. Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy. Z Naturforsch C. 2008 Mar-Apr;63(3-4):176-80. PubMed PMID: 18533458. 20: Vikram A, Jayaprakasha GK, Patil BS. Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography. Anal Chim Acta. 2007 May 8;590(2):180-6. Epub 2007 Mar 18. PubMed PMID: 17448343.