Physicochemical Properties
| Molecular Formula | C22H20O11 |
| Molecular Weight | 460.391 |
| Exact Mass | 460.1 |
| CAS # | 51059-44-0 |
| PubChem CID | 3084961 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 869.0±65.0 °C at 760 mmHg |
| Melting Point | 226-227ºC |
| Flash Point | 304.0±27.8 °C |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.685 |
| LogP | 1.42 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 33 |
| Complexity | 763 |
| Defined Atom Stereocenter Count | 5 |
| SMILES | O1[C@]([H])(C(=O)O[H])[C@]([H])([C@@]([H])([C@]([H])([C@]1([H])OC1C([H])=C(C2C(C([H])=C(C3C([H])=C([H])C([H])=C([H])C=3[H])OC=2C=1OC([H])([H])[H])=O)O[H])O[H])O[H])O[H] |
| InChi Key | LNOHXHDWGCMVCO-NTKSAMNMSA-N |
| InChi Code | InChI=1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1 |
| Chemical Name | (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid |
| Synonyms | Oroxindin Wogonoside |
| 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
| ln Vitro | In RAW264.7 cells, wogonin (0-50 μM, 24 hours) suppresses the production of pro-inflammatory cytokines (IL-6 and TNF-α) and central mediators (NO, PGE2) generated by LPS [1]. Wogonin at 100 μM for 24 hours causes MDA-MB-231 and MCF-7 to proliferate [2]. Wogonin (100 μM, 9–24 hours) causes MDA-MB-231 cells to proliferate [2]. μM, 48-96 hours) can cause G1 phase induction and secretion, as well as suppress the growth of U937 and HL-60 cells [5]. |
| ln Vivo | In the MDA-MB-231 orthotopic model, wogonin (80 mg/kg, gavaged once every other day) inhibits the growth and metastasis of tumors [3]. In A549 cell xenograft models, wogonin (40 or 80 mg/kg, intraperitoneal injection, every three days) inhibits tumor growth and decreases Bcl-2/Bax distribution [4]. Wogonin can also inhibit the U937 xenograft model when administered intraperitoneally once daily for 14 days at a dose of 80 mg/kg. |
| Cell Assay |
Western Blot Analysis[2] Cell Types: MDA-MB-231 cells Tested Concentrations: 100 μM Incubation Duration: 9-24 hrs (hours) Experimental Results: Increased expression of LC3-II and Beclin-1. Inhibits the phosphorylation levels of mTOR Ser2448 and p70S6K Ser-389. |
| Animal Protocol |
Animal/Disease Models: MDA-MB-231 orthotopic model [3] Doses: 80 mg/kg administered Method: po (oral gavage), once every other day. Experimental Results: Inhibited tumor growth (46%) and metastasis in the brain, lungs, liver and bones. Increase the expression of E-cadherin at the original site and decrease the expression of MMP-9, vimentin and Twist1. |
| References |
[1]. Wogonoside displays anti-inflammatory effects through modulating inflammatory mediator expression using RAW264.7 cells. J Ethnopharmacol. 2013 Jun 21;148(1):271-6. [2]. Wogonoside induces autophagy in MDA-MB-231 cells by regulating MAPK-mTOR pathway. Food Chem Toxicol. 2013 Jan;51:53-60. [3]. Wogonoside inhibits invasion and migration through suppressing TRAF2/4 expression in breast cancer. J Exp Clin Cancer Res. 2017 Aug 3;36(1):103. [4]. Wogonoside induces apoptosis in human non-small cell lung cancer A549 cells by promoting mitochondria dysfunction. Biomed Pharmacother. 2018 Oct;106:593-598. [5]. Wogonoside induces cell cycle arrest and differentiation by affecting expression and subcellular localization of PLSCR1 in AML cells. Blood. 2013 May 2;121(18):3682-91. |
| Additional Infomation |
Wogonin 7-O-beta-D-glucuronide is the glycosyloxyflavone which is the 7-O-glucuronide of wogonin. It is a glycosyloxyflavone, a monomethoxyflavone, a monohydroxyflavone, a monosaccharide derivative and a beta-D-glucosiduronic acid. It is functionally related to a wogonin. It is a conjugate acid of a wogonin 7-O-beta-D-glucuronate. Oroxindin has been reported in Scutellaria indica, Scutellaria prostrata, and other organisms with data available. See also: Glycyrrhiza Glabra (part of). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~271.51 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1721 mL | 10.8604 mL | 21.7207 mL | |
| 5 mM | 0.4344 mL | 2.1721 mL | 4.3441 mL | |
| 10 mM | 0.2172 mL | 1.0860 mL | 2.1721 mL |