Physicochemical Properties
| Molecular Formula | C19H14O9 |
| Molecular Weight | 386.31 |
| Exact Mass | 386.064 |
| Elemental Analysis | C, 59.07; H, 3.65; O, 37.27 |
| CAS # | 549-06-4 |
| PubChem CID | 73677 |
| Appearance | White to off-white solid powder |
| Density | 1.591g/cm3 |
| Boiling Point | 744.1ºC at 760mmHg |
| Flash Point | 273.2ºC |
| Index of Refraction | 1.692 |
| LogP | 2.316 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 28 |
| Complexity | 666 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | SKCUFZLDTAYNBZ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C19H14O9/c1-6-4-9(25-3)8(5-20)15-10(6)17(22)27-14-7(2)13(21)11-12(16(14)26-15)19(24)28-18(11)23/h4-5,19,21,24H,1-3H3 |
| Chemical Name | 13,17-dihydroxy-5-methoxy-7,12-dimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-4-carbaldehyde |
| Synonyms | STICTIC ACID; 549-06-4; NSC-87511; NSC87511; NSC 87511; NZR6AX77LP; 1,3-Dihydro-1,4-dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo-7H-isobenzofuro(4,5-b)(1,4)benzodioxepin-11-carboxaldehyde; 13,17-Dihydroxy-5-methoxy-7,12-dimethyl-9,15-dioxo-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-4-carbaldehyde; |
| 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) |
Biological Activity
| Targets | Natural product; secondary metabolite |
| ln Vitro | The growth inhibition of Stictic acid, a secondary metabolite isolated from the lichen Lobaria pulmonaria (L.) Hoffm. (Lobariaceae), was evaluated in vitro on three human cell lines for the first time. The cell lines HT-29 and MCF-7 were utilized for measuring the activity of stictic acid against cancer cells, while the cell line MRC-5 was selected for estimation of its effect on normal cells. The results suggest a moderate anticancer activity (IC50 value for the cell line HT-29 was 29.29 μg/ml) and a low growth inhibition on nonmalignant cells (IC50 value for the cell line MRC-5 was 2478.40 μg/ml) of stictic acid. This natural product can be considered as a promising lead compound for the design of novel human colon adenocarcinoma drugs [1]. |
| Cell Assay |
MTT assay [1] Growth inhibition was evaluated by tetrazolium colorimetric MTT assay. Cells were plated into 96-well microtiter plates in a volume of 90 μl per well, in the complete medium at an optimal seeding density of 5 × 103 cells per well to assure a logarithmic growth rate throughout the assay period. Tested substance (Stictic acid) at a concentration ranging from 10−8 μg to 10−4 M was added to all wells except to the control ones. Plates were incubated at 37 °C for 48 h. Three hours before the end of incubation period 10 μl of MTT solution (5 mg/ml) was added to all wells and plates were incubated for 3 h at 37 °C, after which medium and MTT were removed by suction. The formazan product was then solubilized in 100 μl of 0.04 M HCl of iso-PropOH. After a few minutes at room temperature, the plates were read on a spectrophotometer plate reader at 540/690 nm. The wells without cells containing complete medium and MTT only acted as blank. Growth inhibition was expressed as a percent and calculated according to the formula: % C = 1 − (ODtest/ODcontrol) × 100. |
| References |
[1]. Stictic acid inhibits cell growth of human colon adenocarcinoma HT-29 cells. Arabian Journal of Chemistry. Volume 10, Supplement 1, February 2017, Pages S1240-S1242. |
| Additional Infomation |
LSM-4387 is an aromatic ether. Stictic acid has been reported in Dimelaena oreina, Ramalina hierrensis, and other organisms with data available. In comparison, the lichen substances such as atranorin, gyrophoric acid, parietin and usnic acid were less active toward the cell line HT-29 (IC50 values >200,>200,>200 and 99.70 ± 8.40 μg/ml, respectively) after 72 h exposition (Bačkorová et al., 2011). Furthermore, through investigation of the mechanisms of cytotoxicity of these four secondary metabolites, the same research group found that usnic acid and atranorin were more effective anticancer compounds on HT-29 cells compared to parietin and gyrophoric acid (Bačkorová et al., 2012). However, our results indicate that stictic acid, a widely distributed depsidone among lichens, can be considered as a more promising lead compound for the design of novel human colon adenocarcinoma drugs in relation to usnic acid and atranorin. Hence, structure–activity relationship (SAR) of stictic acid and its derivatives is worthy of investigation.[1] In summary, it may be concluded that stictic acid is more effective anticancer compound on the malignant HT-29 cell line than usnic acid, the most extensively studied lichen metabolite till date (Mitrović et al., 2011). Among the rest, further work should be focused on the molecular mechanism by which this depsidone induces the aforementioned growth inhibition. Taken together, it seems reasonable to assume that stictic acid may inspire new drugs for the treatment of colorectal tumors which are still among the most common and lethal types of cancer worldwide (Botteri et al., 2008).[1] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5886 mL | 12.9430 mL | 25.8859 mL | |
| 5 mM | 0.5177 mL | 2.5886 mL | 5.1772 mL | |
| 10 mM | 0.2589 mL | 1.2943 mL | 2.5886 mL |