Physicochemical Properties
| Molecular Formula | C20H28O8 |
| Molecular Weight | 396.4315 |
| Exact Mass | 396.178 |
| CAS # | 137359-82-1 |
| PubChem CID | 10883790 |
| Appearance | Typically exists as solid at room temperature |
| LogP | -1 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 28 |
| Complexity | 778 |
| Defined Atom Stereocenter Count | 11 |
| SMILES | O1C([C@@]([H])([C@]2([C@@]([H])(C([H])([H])[H])[C@]([H])([C@@]([H])([C@]3([H])[C@@]4(C([H])([H])[H])[C@@]([H])(C(C([H])=C(C([H])([H])[H])[C@]4([H])C([H])([H])[C@]1([H])[C@]32C([H])([H])[H])=O)O[H])O[H])O[H])O[H])O[H])=O |
| InChi Key | NWNMAVFXIRDAPM-RELKVJPISA-N |
| InChi Code | InChI=1S/C20H28O8/c1-7-5-10(21)15(24)18(3)9(7)6-11-19(4)14(18)13(23)12(22)8(2)20(19,27)16(25)17(26)28-11/h5,8-9,11-16,22-25,27H,6H2,1-4H3/t8-,9-,11+,12+,13-,14+,15+,16-,18-,19+,20-/m0/s1 |
| Chemical Name | (1R,2S,3S,7S,9R,12R,13R,14S,15R,16R,17S)-3,12,13,15,16-pentahydroxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.02,7.013,17]heptadec-5-ene-4,11-dione |
| 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
| ln Vitro |
14,15 β-Dihydroxyklaineanone exhibited potent antiproliferative activity against seven human cancer cell lines at a concentration of 25 µM for 48 hours, as determined by MTT assay. It showed the strongest inhibitory effects among the nine tested quassinoids. Notably, it demonstrated selective and potent activity against leukemia cell lines: cell viability was reduced to 5.1% in HL-60 cells and 9.2% in Jurkat cells. It also showed activity against other cancer cell lines: HCT-15 (colon, 36.7% viability), Colo205 (colon, 35.0% viability), PC-3 (prostate, 42.0% viability), HepG2 (liver, 65.7% viability), and KATO III (stomach, 75.1% viability). Importantly, 14,15 β-Dihydroxyklaineanone showed very low toxicity on the normal human skin fibroblast cell line (NB1RGB), with cell viability remaining at 84.4%.[1] |
| Cell Assay |
The antiproliferative activity was evaluated using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Human cancer cell lines (KATO III, HCT-15, Colo205, HepG2, PC-3, Jurkat, HL-60) and a normal skin fibroblast cell line (NB1RGB) were used. Suspension cells were seeded at 1×10⁴ cells/well and adherent cells at 0.5×10⁴ cells/well in 96-well plates. After 24 hours of incubation, cells were treated with 14,15 β-Dihydroxyklaineanone at specified concentrations for 48 hours. At the end of treatment, MTT solution was added to each well, and the cells were incubated for another 4 hours. The formed formazan precipitate was dissolved using 0.04 N HCl in isopropanol. The absorbance was measured at 595 nm using a microplate reader. Cell viability was calculated as a percentage relative to the control culture treated with an equal amount of vehicle (DMSO, not exceeding 0.2% v/v).[1] |
| Toxicity/Toxicokinetics |
In vitro toxicity assessment on the normal human skin fibroblast cell line (NB1RGB) showed low toxicity, with 84.4% cell viability remaining after treatment with 25 µM 14,15 β-Dihydroxyklaineanone for 48 hours.[1] |
| References |
[1]. Quassinoids from the Root of Eurycoma longifolia and Their Antiproliferative Activity on Human Cancer Cell Lines. Pharmacogn Mag. 2017 Jul-Sep;13(51):459-462. |
| Additional Infomation |
14,15beta-Dihydroxyklaineanone has been reported in Eurycoma longifolia with data available. 14,15 β-Dihydroxyklaineanone is a known quassinoid compound isolated from the roots of Eurycoma longifolia Jack. In this study, it was isolated from the ethyl acetate-soluble fraction of the ethanol extract of the plant roots using a combination of silica gel and reversed-phase column chromatography. The study concludes that 14,15 β-Dihydroxyklaineanone is a potent antiproliferative agent with preferential activity against leukemia cells and low toxicity on normal cells, suggesting its potential as a therapeutic candidate for leukemia treatment. However, its mechanism of action is not explained in terms of its structure in this article.[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 | 2.5225 mL | 12.6126 mL | 25.2251 mL | |
| 5 mM | 0.5045 mL | 2.5225 mL | 5.0450 mL | |
| 10 mM | 0.2523 mL | 1.2613 mL | 2.5225 mL |