palmatine

palmatine
Compound Structure:
Synonyms: Palmatine ;3486-67-7 ;Berbericinine ;Palmatin ;O,O-Dimethyldemethyleneberberine
Compound ID: NMPC-1374
PubChem ID:

19009

Molecular Formula: C21H22NO4+
Canonical SMILES: COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
InChIKey: QUCQEUCGKKTEBI-UHFFFAOYSA-N
About the compound:

Palmatine is a protoberberine alkaloid present in various plants, including Phellodendronamurense, CoptisChinensis (Rhizomacoptidis or Chinese goldthread), Corydalis yanhusuo, Tinosporacordifolia (gurjo or heart-leaved moonseed), Tinosporasagittata, Stephaniayunnanensis, and is a major component of the protoberberine extract from Enantiachlorantha. It has garnered interest for potential therapeutic applications in treating jaundice, dysentery, hypertension, inflammation, and liver-related diseases. Palmatine also exhibits weak in vitro activity against flaviviruses. Neuroprotective Activity:Palmatine shows promise in treating Alzheimer’s disease, mainly through the inhibition of acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and neuraminidase-1 (NA-1). Its antidepressant effects have been linked to the regulation of brain catalase levels, monoamine oxidase-A (MAO-A) activity, lipid peroxidation, plasma nitrite, and corticosterone levels. Regulating Blood Lipid Activity:Palmatine has demonstrated hypoglycemic effects by inducing insulin release and mimicking insulin activity. It inhibits the activity of lens aldose reductase, sucrase, and maltase. In vivo studies showed that it reduces serum total cholesterol and triglycerides while increasing high-density lipoprotein cholesterol. Anticancer Activity:Palmatine has shown broad anti-cancer activity against various human cancer cell lines, inducing apoptosis in human skin epithelial carcinoma cells through DNA damage and inhibition of the Bcl-2 protein. It also inhibits the proliferation and infiltration of cancer cells. Antibacterial and Antiviral Activity:Palmatine is more effective against Gram-positive bacteria than Gram-negative bacteria, with 9-O-substituted palmatine derivatives exhibiting stronger antibacterial activity. Anti-inflammatory Activity: It can decrease the production of pro-inflammatory factors and increase the production of anti-inflammatory factors. Other Pharmacological Activities:Palmatine has antioxidant activity and a protective effect on gastric ulcers. Its derivatives are effective against ulcerative colitis and show low cytotoxicity to intestinal epithelial cells. It might also have antiarrhythmic effects and provide protection from myocardial ischemia-reperfusion injury. Overall, palmatine's diverse pharmacological properties make it a compound of interest for various medical applications, although more research is needed to fully understand its efficacy and safety in humans.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

352.4 g/mol

XLogP3-AA

3.7

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

4

Rotatable Bond Count

4

Exact Mass

352.15488318 g/mol

Monoisotopic Mass

352.15488318 g/mol

Topological Polar Surface Area

40.8Ų

Heavy Atom Count

26

Formal Charge

1

Complexity

475

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem            

Source Species: Enantia chlorantha
Phaulopsis falcisepala
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