Molecular Formula | C11H8O3 |
Molar Mass | 188.18 |
Density | 1.354 |
Melting Point | 76-78 °C(lit.) |
Boling Point | 283.17°C (rough estimate) |
Solubility | Soluble in methanol and chloroform |
Appearance | faint orange to dark orange(powder) |
Storage Condition | -20℃ |
Refractive Index | 1.6310 (estimate) |
MDL | MFCD00001682 |
Physical and Chemical Properties | Bioactive Plumbagin (2-Methyljuglone) is a naphthoquinone substance obtained from Plumbago zeylanica L, which has anti-tumor and anti-proliferation activities. |
Use | Uses as dye intermediates for the production of 26 purple, 28 purple, dicyanide, etc |
Hazard Symbols | T - Toxic |
Risk Codes | R25 - Toxic if swallowed R34 - Causes burns R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S37/39 - Wear suitable gloves and eye/face protection S28A - |
UN IDs | UN 2923 8/PG 2 |
Reference Show more | 1. Zhu Yuan, Gao Suping, Luo Liangxu, etc. Adventitious root induction and effect of light quality on the accumulation of baidanin in leaves of Baihua Dan [J]. Journal of Sichuan Agricultural University, 2018, 036(003):337-343 2. Zhou, Rui, et al. "Bioinformatic and experimental." Environmental ecology and pharmacology 70 (2019): 103200.https://doi.org/10.1016/j.etap.2019.10320 3. [IF = 2.711] Hu Ju et al."An aseptic rapid propagation system for obtaining plumbagin of Ceratostigma willmottianum Stapf."Plant Cell Tiss Org. 2019 May;137(2):369-377 4. [IF=4.86] Rui Zhou et al."Bioinformatic and experimental data decipher the pharmacological targets and mechanisms of plumbagin against hepatocellular carcinoma."Environ Toxicol Phar. 2019 Aug;70:103200 5. [IF=4.432] Yujia Liang et al."Pharmacological targets and molecular mechanisms of plumbagin to treat colorectal cancer: A systematic pharmacology study."Eur J Pharmacol. 2020 Aug;881:173227 6. [IF=4.003] Xiuli Chen et al."Synergistic Effect and Mechanism of Plumbagin with Gentamicin Against Carbapenem-Resistant Klebsiella pneumoniae."Infect Drug Resist. 2020; 13: 2751-2759 |
storage conditions | -20°C |
morphology | Crystals or Crystalline Powder |
acidity coefficient (pKa) | 6.70±0.20(Predicted) |
color | Orange |
Merck | 7538 |
EPA chemical information | 1,4-Naphthalenedione, 5-hydroxy-2-methyl- (481-42-5) |
in vitro study
Plumbagin (0, 5, 10, and 15 μM) induces apoptosis of prostate cancer cell lines, such as DU145, CWR22rv1 and LNCaP, in a dose-dependent manner.
Plumbagin (5, 20 μM) obviously inhibits the invasion of PC3, DU145, and CWR22rv1 cells.
Apoptosis Analysis
Cell Line: DU145, CWR22rv1, LNCaP and RWPE-1 cells
Concentration: 0, 5, 10, and 15 μM
Incubation Time: 24 hours
Result: Dose-dependently induced apoptosis of DU145, CWR22rv1 and LNCaP, but showed no effect on RWPE-1 cells at up to 20 μM.
in vivo studies
Plumbagin (2 mg/kg, I .p., five days a week for 11 weeks) inhibits the growth of tumor in male athymic nude mice.
Plumbagin (2 mg/kg, I .p., five days a week for 11 weeks) inhibits expression of PKCε, suppresses JAK-2 and Stat3 phosphorylation, and activates Stat3, PCNA, VEGF and MMP-9 in mice.
Animal Model: Male athymic nude mice bearing DU145 cells
Dosage: 2 mg/kg
Administration: I .P. after 3 days post cell implantation, five days a week.
Result: Delayed tumor growth by 3 weeks, and reduced tumor weight and volume in mice.