Isolimonic acidCAS# 74729-97-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 74729-97-8 | SDF | Download SDF |
| PubChem ID | 102059881 | Appearance | Powder |
| Formula | C26H32O9 | M.Wt | 488.5 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 3-[(1R,2R,4S,7S,8S,11R,16R)-7-(furan-3-yl)-1,8,15,15-tetramethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.02,4.02,8.012,16]octadecan-12-yl]-3-hydroxypropanoic acid | ||
| SMILES | CC1(C2CC(=O)C3(C(C2(CO1)C(CC(=O)O)O)CCC4(C35C(O5)C(=O)OC4C6=COC=C6)C)C)C | ||
| Standard InChIKey | SZSLZBYOLTYIOE-NQUDZKMVSA-N | ||
| Standard InChI | InChI=1S/C26H32O9/c1-22(2)15-9-16(27)24(4)14(25(15,12-33-22)17(28)10-18(29)30)5-7-23(3)19(13-6-8-32-11-13)34-21(31)20-26(23,24)35-20/h6,8,11,14-15,17,19-20,28H,5,7,9-10,12H2,1-4H3,(H,29,30)/t14-,15-,17?,19-,20+,23-,24-,25?,26+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Isolimonic acid Dilution Calculator
Isolimonic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0471 mL | 10.2354 mL | 20.4708 mL | 40.9417 mL | 51.1771 mL |
| 5 mM | 0.4094 mL | 2.0471 mL | 4.0942 mL | 8.1883 mL | 10.2354 mL |
| 10 mM | 0.2047 mL | 1.0235 mL | 2.0471 mL | 4.0942 mL | 5.1177 mL |
| 50 mM | 0.0409 mL | 0.2047 mL | 0.4094 mL | 0.8188 mL | 1.0235 mL |
| 100 mM | 0.0205 mL | 0.1024 mL | 0.2047 mL | 0.4094 mL | 0.5118 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- (2Z,6E)-Farnesyl acetate
Catalog No.:BCX0433
CAS No.:40266-29-3
- Carbendazim
Catalog No.:BCX0432
CAS No.:10605-21-7
- Anisyl alcohol
Catalog No.:BCX0431
CAS No.:105-13-5
- Deacetylnomilinic acid
Catalog No.:BCX0430
CAS No.:35930-21-3
- Ichangin
Catalog No.:BCX0429
CAS No.:10171-61-6
- Obacunone 17-O-glucoside
Catalog No.:BCX0428
CAS No.:123564-64-7
- 3-epi-Actinidic acid
Catalog No.:BCX0427
CAS No.:143839-01-4
- (±)-Dihydrodehydrodiconiferyl alcohol
Catalog No.:BCX0426
CAS No.:85165-02-2
- (-)-Isolariciresinol
Catalog No.:BCX0425
CAS No.:110268-37-6
- 21,23-Dihydro-21-hydroxy-23-oxonomilin
Catalog No.:BCX0424
CAS No.:2243600-32-8
- Procymidone
Catalog No.:BCX0423
CAS No.:32809-16-8
- Azoxystrobin
Catalog No.:BCX0422
CAS No.:131860-33-8
- Anibadimer A
Catalog No.:BCX0435
CAS No.:23768-65-2
- 5-Deoxyisorhoifolin
Catalog No.:BCX0436
CAS No.:2055239-29-5
- 1(10)Z,4Z-Furanodienone
Catalog No.:BCX0437
CAS No.:88010-63-3
- Thalifaronine
Catalog No.:BCX0438
CAS No.:105458-70-6
- Huazhongilexol
Catalog No.:BCX0439
CAS No.:161407-80-3
- Thalifaramine
Catalog No.:BCX0440
CAS No.:105437-16-9
- (12Z)-Labda-8(17),12-diene-14,15,16-triol
Catalog No.:BCX0441
CAS No.:1630864-26-4
- Citrusin
Catalog No.:BCX0442
CAS No.:108943-57-3
- 7-O-Galloyl-D-sedoheptulose
Catalog No.:BCX0443
CAS No.:233690-85-2
- 1,7-Di-O-Galloyl-D-sedoheptulose
Catalog No.:BCX0444
CAS No.:126622-78-4
- Durianol A
Catalog No.:BCX0445
CAS No.:1941203-91-3
- Morofficinaloside
Catalog No.:BCX0446
CAS No.:78964-45-1
Oenothera rosea L Her. ex Ait attenuates acute colonic inflammation in TNBS-induced colitis model in rats: in vivo and in silico myeloperoxidase role.[Pubmed:30372897]
Biomed Pharmacother. 2018 Dec;108:852-864.
Oenothera rosea L Her. ex Ait is a species traditionally used in the treatment of inflammation, headache, stomach pain, infections, among others. The aim of this study was evaluating the acute anti-inflammatory activity of the aqueous extract of O. rosea by 2,4,6-trinitrobenzene sulfonic acid (TNBS)-induced colitis. Rats were randomized into six groups: (I) Sham; (II) EtOH; (III) TNBS; and (IV-VI) 250, 500 and 750 mg/Kg, respectively. The colonic injury was induced (groups III-VI) by intrarectal instillation of 0.25 mL of TNBS (10 mg) in 50% ethanol. Groups I and II received an enema (0.25 mL) of physiological saline solution or 50% ethanol, respectively. Treatments were administered by oral gavage 48, 24 and 1 h prior, and 24 h after the induction. The inflammatory response was assessed considering the macroscopic and microscopic damage, the serum nitric oxide (NO), the colonic IL-1beta levels, and the myeloperoxidase (MPO) activity. Moreover, we performed an LC-MS-based metabolite profiling, and a docking on the MPO. Doses of 500 and 750 mg/Kg showed a protective effect in the TNBS-induced colonic damage. This activity was related to the downregulation of evaluated parameters. Also, considering previous reports, 29 metabolites of 91 detected were selected for the docking, of which Isolimonic acid (29) and Kaempferol 3-(2'',4''-diacetylrhamnoside) (10) showed the highest affinity to MPO. The aqueous extract of O. rosea protected the TNBS-induced colonic damage in rats, an effect that could be associated with the presence of polyphenolic compounds, alkaloids, and terpenes; as well as their ability to down-regulate MPO activity.
Isolimonic acid interferes with Escherichia coli O157:H7 biofilm and TTSS in QseBC and QseA dependent fashion.[Pubmed:23153211]
BMC Microbiol. 2012 Nov 15;12:261.
BACKGROUND: E. coli O157:H7 (EHEC) is an important human pathogen. The antibiotic treatment of EHEC reportedly results in release of Shiga toxin and is therefore discouraged. Consequently, alternative preventive or therapeutic strategies for EHEC are required. The objective of the current study was to investigate the effect of citrus limonoids on cell-cell signaling, biofilm formation and type III secretion system in EHEC. RESULTS: Isolimonic acid and ichangin were the most potent inhibitors of EHEC biofilm (IC25=19.7 and 28.3 muM, respectively) and adhesion to Caco-2 cells. The qPCR analysis revealed that Isolimonic acid and ichangin repressed LEE encoded genes by approximately 3 to 12 fold. In addition, flhDC was repressed by the two limonoids ( approximately 3 to 7 fold). Further studies suggested that Isolimonic acid interferes with AI-3/epinephrine activated cell-cell signaling pathway. Loss of biofilm inhibitory activity of Isolimonic acid in DeltaqseBC mutant, which could be restored upon complementation, suggested a dependence on functional QseBC. Additionally, overexpression of qseBC in wild type EHEC abated the inhibitory effect of Isolimonic acid. Furthermore, the Isolimonic acid failed to differentially regulate ler in DeltaqseA mutant, while plasmid borne expression of qseA in DeltaqseA background restored the repressive effect of Isolimonic acid. CONCLUSIONS: Altogether, results of study seem to suggest that Isolimonic acid and ichangin are potent inhibitors of EHEC biofilm and TTSS. Furthermore, Isolimonic acid appears to interfere with AI-3/epinephrine pathway in QseBC and QseA dependent fashion.
Citrus limonoids interfere with Vibrio harveyi cell-cell signalling and biofilm formation by modulating the response regulator LuxO.[Pubmed:20864476]
Microbiology (Reading). 2011 Jan;157(Pt 1):99-110.
Citrus limonoids are unique secondary metabolites, characterized by a triterpenoid skeleton with a furan ring. Studies have demonstrated beneficial health properties of limonoids. In addition, certain citrus limonoids play a role in plant defence against insect pests. In the present study, five limonoids were purified from sour orange and evaluated for their ability to inhibit cell-cell signalling. The purified limonoids were tested for their ability to interfere with cell-cell signalling and biofilm formation in Vibrio harveyi. Isolimonic acid, deacetylnomilinic acid glucoside and ichangin demonstrated significant inhibition of autoinducer-mediated cell-cell signalling and biofilm formation. Furthermore, Isolimonic acid and ichangin treatment resulted in induced expression of the response regulator gene luxO. In addition, luxR promoter activity was not affected by Isolimonic acid or ichangin. Therefore, the ability of Isolimonic acid and ichangin to interfere with cell-cell signalling and biofilm formation seems to stem from the modulation of luxO expression. The results suggest that Isolimonic acid and ichangin are potent modulators of bacterial cell-cell signalling.
Novel triterpenoid from Citrus aurantium L. possesses chemopreventive properties against human colon cancer cells.[Pubmed:18490169]
Bioorg Med Chem. 2008 Jun 1;16(11):5939-51.
Potential cancer preventive constituents of sour orange (Citrus aurantium L.) were isolated and identified from EtOAc extract of sour orange. Crude EtOAc extract was purified using silica gel column chromatography to isolate two putative bioactive compounds. The purity of the isolated compounds was analyzed by TLC and HPLC. The structures of the two compounds were identified by one-dimensional ((1)H, (13)C) and two-dimensional ((1)H-H and (1)H-(13)C) NMR experiments as Isolimonic acid and a novel compound named as ichanexic acid. Stereochemical assignment of the protons for both the compounds was made using one-dimensional nuclear Overhauser enhancement (nOe) experiments. The identified compounds were tested for the inhibition of human colon cancer cells (HT-29) proliferation, apoptosis, and on non-cancerous (COS-1 fibroblast) cells. Cell proliferation, arrest of cell growth, and induction of apoptosis were determined by MTT assay, flow cytometry, and nuclear staining methods, respectively. The MTT assay indicated that both the compounds exhibited differential inhibition at various concentrations. Significant arrest of cell growth by isolimonoic acid was noticed within 24h of treatment on the HT-29 colon cancer cells at a concentration as low as 5.0microM (P=0.005) and by ichanexic acid at 10.0microM (P=0.011). None of the compounds exerted any apparent cytostatic effects on the non-cancerous COS-1 fibroblast cells. Both the compounds exerted nearly 4- to 5-fold increase in the counts of G2/M stage cells at 5microM indicating a potential role in the cell cycle arrest as well as possible lead structures for the development of cancer chemopreventive and therapeutic agents. To the best of our knowledge, this is the first report on isolation, identification of Isolimonic acid in its native form, and compound 2 was found to a novel and identified as ichanexic acid.
Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography.[Pubmed:17448343]
Anal Chim Acta. 2007 May 8;590(2):180-6.
High performance liquid chromatography (HPLC) method has been developed for simultaneous quantification of limonoid aglycones and glucosides on a reversed phase C18 column using a binary solvent system, coupled with diode array detector. Seven limonoids such as limonin, nomilin, Isolimonic acid, ichangin, isoobacunoic acid, limonin 17-beta-D glucopyranoside and deacetyl nomilinic acid 17-beta-D glucopyranoside were separated and detected at 210 nm. Furthermore, limonoids were separated, identified and quantified in four varieties of citrus fruits and seeds using developed method. Limonin and limonin glucoside were found to be the predominant limonoid aglycone and glucoside, respectively, in all tested samples. The sensitivity of the method was found to be 0.25-0.50 microg for tested limonoids.
