| Field | Specification |
|---|---|
| Target | |
| CAS no. | |
| Applications | |
| Source | Plant — Phytolaccaceae Phytolacca americana L. |
| Molecular weight | |
| Molecular formula | C18H16O6 |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Americanin A is a neolignan that can be isolated from the seeds of Phytolacca americana. It activates ATM and ATR, triggering downstream signaling cascades that include Chk1, Chk2 and the tumor suppressor p53, and it selectively targets Skp2 for degradation, thereby stabilizing p27. The compound also suppresses Cyclin B1 and its partner cdc2 to block entry into mitosis and induces apoptosis through excess ROS production, giving it anti-cancer activity against colorectal cancer[1]. It has the molecular formula C18H16O6 and a molecular weight of 328.32 g/mol.
Physical & Chemical Properties
| CAS Number | 69506-79-2 |
|---|---|
| Molecular Formula | C18H16O6 |
| Molecular Weight | 328.32 g/mol |
| Structure Classification | Phenols Monophenols |
| SMILES | OC[C@H]1[C@H](C2=CC(O)=C(C=C2)O)OC3=CC=C(/C=C/C=O)C=C3O1 |
| Target | Chk1, Chk2, ATM, ATR |
| Signaling Pathway | Cell Cycle/DNA Damage; PI3K/Akt/mTOR; Apoptosis; Metabolic Enzyme/Protease; NF-κB; Immunology/Inflammation |
| Initial Source | Plant — Phytolaccaceae Phytolacca americana L. |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
Over 24–72 h, Americanin A selectively suppresses the proliferation of human cancer cells (IC50 9.0–66.4 μM) without a significant effect on MRC-5 normal cells, and suppresses HCT116 cells in a concentration- and time-dependent manner[1]. In HCT116 cells, Americanin A at 7.5-30 μM for 24 h induces G2/M cell-cycle arrest, and 30 μM raises the proportion of G2/M phase cells to 38.9%[1]. DNA damage in HCT116 cells is induced by Americanin A (7.5–30 μM; 24 h), shown by a rise in phosphorylated H2A.X and a fall in acetylated H3[1]. Americanin A (7.5–30 μM; 48 h) triggers apoptosis in HCT116 cells by the end of the 48 h treatment, and 30 μM raises the proportion of sub-G1 cells to 52.0%[1].
Cell Proliferation Assay[1]
| Cell Line | A549, Caki-1, K562, HCT116, SW480, HCT-15, RKO, MRC-5 |
|---|---|
| Concentration | IC₅₀ values (9.0–66.4 μM for cancer cells; >100 μM for MRC-5) |
| Incubation Time | 24 h, 48 h, 72 h |
| Result | Inhibited proliferation of A549 (IC50 39.1 μM), Caki-1 (IC50 66.4 μM), K562 (IC50 12.9 μM), HCT116 (IC50 9.0 μM), SW480 (IC50 27.4 μM), HCT-15 (IC50 12.5 μM), RKO (IC50 24.4 μM) cells; measured HCT116 IC50 values of 24.1 μM (24 h), 9.6 μM (48 h), 8.7 μM (72 h); showed no significant inhibition of MRC-5 cells (IC50 > 100 μM). |
Cell Cycle Analysis[1]
| Cell Line | HCT116 |
|---|---|
| Concentration | 7.5, 15, 30 μM |
| Incubation Time | 24 h |
| Result | Increased the proportion of G₂/M phase cells from 20.6% (untreated) to 38.9% at 30 μM; increased sub-G₁ cell proportion (apoptosis indicator) concentration-dependently, but the increase was not significant at 24 h. |
Western Blot Analysis[1]
| Cell Line | HCT116 |
|---|---|
| Concentration | 7.5, 15, 30 μM |
| Incubation Time | 24 h |
| Result | Suppressed expression of cyclin A, cyclin B1, phosphorylated cyclin B1 (Ser147), CDK2, and cdc2 in a concentration-dependent manner.\nIncreased phosphorylation of histone H2A.X (Ser139) and decreased acetylation of histone H3 (Lys9) concentration-dependently. |
Apoptosis Analysis[1]
| Cell Line | HCT116 |
|---|---|
| Concentration | 7.5, 15, 30 μM |
| Incubation Time | 48 h |
| Result | Increased sub-G₁ cell proportion from 6.5% (untreated) to 52.0% at 30 μM; showed increased early and late apoptotic cells concentration-dependently via annexin V/FITC staining. |
In Vivo
In nude mice, Americanin A (5-10 mg/kg, i.p., three times weekly) inhibits HCT116 tumor xenograft growth, reducing tumor volume by 45.0% at 5 mg/kg and 55.7% at 10 mg/kg through Skp2-dependent p27 stabilization[1].
| Animal Model | BALB/c-nu (female, 4-6 weeks old, HCT116 tumor xenograft)[1] |
|---|---|
| Dosage | 5 mg/kg; 10 mg/kg |
| Administration | i.p.; three times a week |
| Result | Reduced tumor volumes by 45.0% (5 mg/kg) and 55.7% (10 mg/kg) compared to vehicle; Increased expressions of p21 and p27, and decreased Skp2 expression in excised tumors; Showed pronounced p27 staining and diminished Skp2 and Ki-67 staining via immunohistochemistry; Observed no overt toxicity or body weight changes. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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