Palmatine

Palmatine is a protoberberine alkaloid found in several plants including Phellodendron amurense, Coptis Chinensis[1] (Rhizoma coptidis, chinese goldthread) and Corydalis yanhusuo,[2] Tinospora cordifolia[3] (gurjo, heart-leaved moonseed), Tinospora sagittata,[4] Phellodendron amurense[5] (amur cork tree), Stephania yunnanensis.[6]

palmatine
Names
IUPAC name
2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
Other names
Berbericinine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3
    Key: AEQDJSLRWYMAQI-UHFFFAOYAT
  • O(c1c4c(ccc1OC)CC3c2c(cc(OC)c(OC)c2)CCN3C4)C
Properties
C21H22NO4+
Molar mass 352.4083 g/mol
Density 1.23 g/cm3
Boiling point 482.9 °C (901.2 °F; 756.0 K) at 760 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is the major component of the protoberberine extract from Enantia chlorantha.[7]

It has been studied for its potential use in the treatment of jaundice, dysentery, hypertension, inflammation, and liver-related diseases.[8] This compound also has weak in vitro activity against flavivirus.[9]

Pharmacology

Neuroprotective activity

Palmatine can be used to treat Alzheimer’s disease, mainly by inhibiting the activity of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and neuraminidase-1 (NA-1). It was found, that the positively charged nitrogen on palmatine binds in the gorge of active sire of AChE.[10]

Research show that palmatine had antidepressant effect. It was achieved by regulating brain catalase levels, monoamine oxidase-A (MAO-A) activity, lipid peroxidation, plasma nitrite and corticosterone levels.[11]

Regulating blood lipid activity

Palmatine achieved hypoglycemic effects by inducing insulin release and insulin-mimicking activity.[12][13] In addition, studies found that palmatine also inhibited the activity of lens aldose reductase,[14] sucrase and maltase.[15] In vivo research showed that palmatine reduced serum total cholesterol (TC) and triglycerides (TG) and increased serum high-density lipoprotein cholesterol.[16]

Anticancer activity

Research showed that palmatine had broad anti-cancer activity. Palmatine had significant growth inhibitory effects on seven human cancer cell lines: 7701QGY, SMMC7721, HepG2, CEM, CEM/VCR, K III and Lewis.[17] In addition, palmatine also had anti-cancer activity on MCF-7, U251, KB,[18] CHOK-1, HT-29 and SiHacell lines.[19] Palmatine induced apoptosis in human skin epithelial carcinoma cells (A431) in a concentration- and time-dependent manner via damaging severely to DNA and inhibiting the activity of Bcl-2 protein.[20][21][22] In addition, palmatine can inhibit the proliferation and infiltration of cancer cells.

Antibacterial and antiviral activity

Palmitine has inhibitory effect on Gram-positive bacteria which is significantly stronger than that on Gram-negative bacteria,[23] and 9-O-substituted palmatine derivatives exhibited stronger antibacterial activity.[24][25]

Anti-inflammatory activity

Study showed, that palmatine can decrease the production of pro-inflammatory factors and increase the production of anti-inflammatory factors.[26]

Other pharmacological activity

Studies showed that palmatine had antioxidant activity,[27][28] had a protective effect on gastric ulcer,[29] derivatives of palmatine were more effective against ulcerative colitis, including low cytotoxicity tointestinal epithelial cells.[30] In addition, palmatine might have the antiarrhythmic effect,[31] and provideprotection from myocardial ischemia-reperfusion injury.[32]

Toxicity

A large number of studies have shown that palmatine has a complex effect on the metabolism of enzymes in the liver, and that palmatine has significant DNA toxicity.[33] However, some 9-O-substituted palmatine derivatives exhibited less toxic than palmatine.[34] In addition, palmatine had higher affinity to nucleic acids than serum proteins, which make them suitable candidates for delivery by serum proteins.[35]

See also

References
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