| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H21NO4 |
| Molecular Weight | 327.3743 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(O)C=C2C[C@@H]3N(C)CCC4=CC(O)=C(OC)C(C2=C1)=C34
InChI
InChIKey=LZJRNLRASBVRRX-ZDUSSCGKSA-N
InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1
Boldine, an aporphine alkaloid, found abundantly in the leaves/bark of boldo (Peumus boldus Molina) widely consumed in the folk medicine of some regions. Boldine possesses various pharmacological properties including, anticancer activity. It exhibits a significant improvement of learning and memory through inhibition of brain acetylcholinesterase activity and alleviation of brain oxidative stress, which was shown on animal models. Boldine is a potentially useful agent for the treatment of leishmaniosis. In addition, it suppresses osteoclastogenesis, improves bone destruction and may be a potential therapeutic agent for rheumatoid arthritis. Besides, was shown, that boldine inhibits telomerase in cells treated with sub-cytotoxic concentrations. Telomerase inhibition occurs via down-regulation of human telomerase reverse transcriptase (hTERT), the catalytic subunit of the enzyme.
CNS Activity
Approval Year
PubMed
Sample Use Guides
in mice: boldine (1.5, 3 and 6mg/kg, po) for 7 successive days exhibited significant improvement of learning and memory of young and aged mice
anticonvulsant effects in mice: boldine (once in a day for 8 days, ip.)
in mice: repeated i. p. injections of 30, 60, or 90 mg boldine/kg slowed tumor growth
Route of Administration:
Other
It was shown that boldine is a potentially useful agent for the treatment of leishmaniasis. The in vitro system consisted of murine macrophage infection with amastigotes of L. amazonensis treated with different concentrations from 50 to 600 μg/ml of boldine for 24 hr. Intracellular parasite destruction was assessed by morphological examination and boldine cytotoxicity to macrophages was tested by the MTT viability assay. When cells were treated with 100 μg/ml of boldine the reduction of parasite infection was 81% compared with untreated cultures cells.
SUBSTANCE RECORD
