Isolated from Maackia amurensis Rupr.et Maxim, Maackiain is a novel and potent larvicidal agent against Aedes aegypti mosquito.xp Parasitol (LD50 = 21.95 µg/mL). Maackiain (DL-Maackiain) is an inducer of fragmentations of DNA to oligonucleosomal-sized fragments that like a characteristic of apoptosis in the HL-60 cells.
Physicochemical Properties
| Molecular Formula | C16H12O5 |
| Molecular Weight | 284.26348 |
| Exact Mass | 284.068 |
| Elemental Analysis | C, 67.60; H, 4.26; O, 28.14 |
| CAS # | 19908-48-6 |
| PubChem CID | 91510 |
| Appearance | White to off-white solid powder |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 436.2±45.0 °C at 760 mmHg |
| Flash Point | 217.6±28.7 °C |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.677 |
| LogP | 2.79 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 21 |
| Complexity | 416 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C1=CC2=C(C=C1O)OC[C@H]3C4=CC5=C(C=C4O[C@@H]23)OCO5 |
| InChi Key | HUKSJTUUSUGIDC-BDJLRTHQSA-N |
| InChi Code | InChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m1/s1 |
| Chemical Name | 6H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,12a-dihydro-, cis-(+-)- |
| Synonyms | Inermin |
| 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | Aedes aegypti mosquito.xp Parasitol(LD50= 21.95 µg/mL) |
| ADME/Pharmacokinetics |
Metabolism / Metabolites Maackiain has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-2-carboxylic acid. |
| References |
[1]. Extract of Bowdichia virgilioides and maackiain as larvicidal agent against Aedes aegypti mosquito.xp Parasitol. 2015 Jun;153:160-4. [2]. Induction of apoptosis by maackiain and trifolirhizin (maackiain glycoside) isolated from sanzukon (Sophora Subprostrate Chen et T. Chen) in human promyelotic leukemia HL-60 cells.Oncol Rep. 2004 Dec;12(6):1183-8. |
| Additional Infomation |
(-)-maackiain is the (-)-enantiomer of maackiain. It is an enantiomer of a (+)-maackiain. Maackiain has been reported in Pongamia pinnata var. pinnata, Caragana frutex, and other organisms with data available. See also: (+)-Maackiain (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~250 mg/mL (~879.48 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.08 mg/mL (7.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5179 mL | 17.5895 mL | 35.1791 mL | |
| 5 mM | 0.7036 mL | 3.5179 mL | 7.0358 mL | |
| 10 mM | 0.3518 mL | 1.7590 mL | 3.5179 mL |