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3'-O-Acetylhamaudol is a natural product extracted from Angelica japonica roots, exhibiting potent anti-tumor activity through dual actions such as anti-angiogenesis and intestinal intraepithelial lymphocyte activation.
| ln Vitro |
3'-O-Acetylhamaudol inhibits the proliferation, migration, and tube formation of human umbilical vein endothelial cells (HUVECs) in a concentration-dependent manner (1-20 μM); at 20 μM, it reduces HUVEC proliferation by 65%, migration by 70%, and tube formation by 80% compared to the control group[1]
3'-O-Acetylhamaudol activates intestinal intraepithelial lymphocytes (IELs) isolated from C57BL/6 mice, increasing the proportion of CD4+ and CD8+ T cells expressing IFN-γ and IL-2; at 10 μM, it enhances IFN-γ secretion by 2.3-fold and IL-2 secretion by 1.8-fold in IEL cultures[1] 3'-O-Acetylhamaudol shows no direct cytotoxicity against murine colon cancer cells (CT26) or human colon cancer cells (HT-29) at concentrations up to 20 μM[1] |
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| ln Vivo |
3'-O-Acetylhamaudol inhibits tumor growth in a CT26 colon cancer xenograft mouse model; oral administration at 50 mg/kg and 100 mg/kg once daily for 21 days reduces tumor volume by 42% and 68%, respectively, and tumor weight by 38% and 63% compared to the vehicle control[1]
3'-O-Acetylhamaudol suppresses tumor angiogenesis in vivo, as indicated by a 55% reduction in microvessel density (MVD) in tumor tissues of mice treated with 100 mg/kg dose (assessed via CD31 immunohistochemical staining)[1] 3'-O-Acetylhamaudol enhances the number and activation status of intestinal IELs in tumor-bearing mice; the 100 mg/kg dose increases the percentage of CD4+IFN-γ+ and CD8+IFN-γ+ IELs by 1.9-fold and 2.2-fold, respectively[1] |
| Cell Assay |
For HUVEC functional assays: Culture HUVECs in EBM-2 medium supplemented with growth factors; seed cells in 96-well plates (proliferation assay), 24-well plates with transwell inserts (migration assay), or Matrigel-coated 96-well plates (tube formation assay); treat cells with 3'-O-Acetylhamaudol (1-20 μM) for 24-48 hours; assess proliferation via MTT assay, migration via crystal violet staining of migrated cells, and tube formation via counting the number of complete capillary-like structures[1]
For IEL activation assay: Isolate IELs from the small intestines of C57BL/6 mice via mechanical disruption and Percoll gradient centrifugation; culture IELs in RPMI 1640 medium with 10% fetal bovine serum; treat with 3'-O-Acetylhamaudol (1-20 μM) for 48 hours; analyze CD4+ and CD8+ T cell subsets via flow cytometry, and measure IFN-γ and IL-2 levels in culture supernatants via ELISA[1] For direct cytotoxicity assay: Culture CT26 and HT-29 cells in RPMI 1640 medium; treat with 3'-O-Acetylhamaudol (1-20 μM) for 72 hours; evaluate cell viability via MTT assay[1] |
| Animal Protocol |
For colon cancer xenograft model: Use female BALB/c mice (6-8 weeks old); inoculate 5×10⁶ CT26 cells subcutaneously into the right flank; when tumors reach 100 mm³, randomly divide mice into three groups (vehicle control, 50 mg/kg, 100 mg/kg 3'-O-Acetylhamaudol); dissolve the compound in 0.5% carboxymethylcellulose sodium (CMC-Na) and administer via oral gavage once daily for 21 days; measure tumor volume every 3 days using calipers, and weigh tumors after sacrifice; collect tumor tissues for CD31 immunohistochemical staining to assess MVD, and isolate intestinal IELs for flow cytometry analysis[1]
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| References | |
| Additional Infomation |
[(3S)-5-hydroxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl]acetate has been reported in Angelica sinensis and Saposhnikovia divaricata, and relevant data are available. 3'-O-acetylhamool is the main bioactive component isolated from the root of Angelica sinensis [1]. Its antitumor mechanism involves a dual action: inhibiting tumor angiogenesis by suppressing endothelial cell function, and enhancing antitumor immunity by activating intestinal intraepithelial lymphocytes (IELs) to secrete pro-inflammatory cytokines (IFN-γ, IL-2) [1]. 3'-O-acetylhamool exerts its antitumor effect not directly against cancer cells, but rather relies on anti-angiogenic and immunomodulatory effects. Pathway [1]
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| Molecular Formula |
C17H18O6
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|---|---|
| Molecular Weight |
318.321
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| Exact Mass |
318.11
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| CAS # |
30358-88-4
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| PubChem CID |
5315865
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| Appearance |
White to off-white solid powder
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| LogP |
2.7
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
23
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| Complexity |
551
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| Defined Atom Stereocenter Count |
1
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| SMILES |
c12C([H])([H])C(OC(=O)C([H])([H])[H])([H])C(C([H])([H])[H])(C([H])([H])[H])Oc1c(c1c(c2O[H])C(=O)C([H])=C(C([H])([H])[H])O1)[H]
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| InChi Key |
ZHMBJOBSCRAOAO-AWEZNQCLSA-N
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| InChi Code |
InChI=1S/C17H18O6/c1-8-5-11(19)15-13(21-8)7-12-10(16(15)20)6-14(22-9(2)18)17(3,4)23-12/h5,7,14,20H,6H2,1-4H3/t14-/m0/s1
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| Chemical Name |
[(3S)-5-hydroxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] acetate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~20 mg/mL (~62.83 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2 mg/mL (6.28 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 20.0 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 mg/mL (6.28 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 20.0 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. View More
Solubility in Formulation 3: ≥ 2 mg/mL (6.28 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1415 mL | 15.7075 mL | 31.4149 mL | |
| 5 mM | 0.6283 mL | 3.1415 mL | 6.2830 mL | |
| 10 mM | 0.3141 mL | 1.5707 mL | 3.1415 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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