Names | |
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IUPAC name 2,3,9,10-Tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium | |
Other names Berbericinine | |
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3D model (JSmol) | |
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PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C21H21NO4+ | |
Molar mass | 351.401 g·mol−1 |
Density | 1.23 g/cm3 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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]
It is the major component of the protoberberine extract from Enantia chlorantha . [7] [ better source needed ]
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]
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]
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]
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.
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]
Studies have shown that palmatine can decrease the production of pro-inflammatory factors and increase the production of anti-inflammatory factors. [26]
Studies have shown that palmatine chave antioxidant activity, [27] [28] had a protective effect on gastric ulcer, [29] derivatives of palmatine were more effective against ulcerative colitis, including low cytotoxicity to intestinal epithelial cells. [30] In addition, palmatine might have the antiarrhythmic effect, [31] and provideprotection from myocardial ischemia-reperfusion injury. [32]
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]
The epithelial–mesenchymal transition (EMT) is a process by which epithelial cells lose their cell polarity and cell–cell adhesion, and gain migratory and invasive properties to become mesenchymal stem cells; these are multipotent stromal cells that can differentiate into a variety of cell types. EMT is essential for numerous developmental processes including mesoderm formation and neural tube formation. EMT has also been shown to occur in wound healing, in organ fibrosis and in the initiation of metastasis in cancer progression.
Chelerythrine is a benzophenanthridine alkaloid present in the plant Chelidonium majus. It is a potent, selective, and cell-permeable protein kinase C inhibitor in vitro. And an efficacious antagonist of G-protein-coupled CB1 receptors. This molecule also exhibits anticancer qualities and it has served as a base for many potential novel drugs against cancer. Structurally, this molecule has two distinct conformations, one being a positively charged iminium form, and the other being an uncharged form, a pseudo-base.
Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants including species of Berberis, from which its name is derived.
Coptisine is an alkaloid found in Chinese goldthread, greater celandine, and opium. Famous for the bitter taste that it produces, it is used in Chinese herbal medicine along with the related compound berberine for digestive disorders caused by bacterial infections.
Phytoecdysteroids are plant-derived ecdysteroids. Phytoecdysteroids are a class of chemicals that plants synthesize for defense against phytophagous insects. These compounds are mimics of hormones used by arthropods in the molting process known as ecdysis. When insects eat the plants with these chemicals they may prematurely molt, lose weight, or suffer other metabolic damage and die.
PIN2/TERF1-interacting telomerase inhibitor 1, also known as PINX1, is a human gene. PINX1 is also known as PIN2 interacting protein 1. PINX1 is a telomerase inhibitor and a possible tumor suppressor.
Metastasis-associated protein MTA3 is a protein that in humans is encoded by the MTA3 gene. MTA3 protein localizes in the nucleus as well as in other cellular compartments MTA3 is a component of the nucleosome remodeling and deacetylate (NuRD) complex and participates in gene expression. The expression pattern of MTA3 is opposite to that of MTA1 and MTA2 during mammary gland tumorigenesis. However, MTA3 is also overexpressed in a variety of human cancers.
Granzyme K (GrK) is a protein that is encoded by the GZMK gene on chromosome 5 in humans. Granzymes are a family of serine proteases which have various intracellular and extracellular roles. GrK is found in granules of natural killer (NK) cells and cytotoxic T lymphocytes (CTLs), and is traditionally described as being cytotoxic towards targeted foreign, infected, or cancerous cells. NK cells and CTLs can induce apoptosis through the granule secretory pathway, which involves the secretion of granzymes along with perforin at immunological synapses.
Glaucine(1,2,9,10-TetraMethoxyAporphine, Bromcholitin, Glauvent, Tusidil, Tussiglaucin) is an aporphine alkaloid found in several different plant species in the family Papaveraceae such as Glaucium flavum, Glaucium oxylobum and Corydalis yanhusuo, and in other plants like Croton lechleri in the family Euphorbiaceae.
Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.
Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid. It has been isolated from the Asian vine Menispermum dauricum, commonly known as Asian moonseed, and the North American vine Menispermum canadense, commonly known as Canadian moonseed. Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so. Dauricine has been studied in vitro for its potential to inhibit cancer cell growth and to block cardiac transmembrane Na+, K+, and Ca2+ ion currents.
(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.
Solasonine is a glycoalkaloid that is found in Solanum plants of the family Solanaceae. Solasonine is a poisonous chemical compound when used at high levels. It is a glycoside of solasodine. Glycoalkaloids such as solasonine have various applications including pharmacology, cancer treatments and even a role as a pesticide.
Huáng bǎi, huáng bó or huáng bò is one of the fifty fundamental herbs of traditional Chinese medicine. Known also as Cortex Phellodendri, it is the bark of one of two species of Phellodendron tree: Phellodendron amurense or Phellodendron chinense.
Cāng zhú, also known as black atractylodes rhizome or Rhizoma Atractylodes, is a Chinese herbal medicine. It is the dried rhizome of Atractylodes lancea (Thunb.) DC., synonyms Atractylodes chinensis (DC.) Koidz, and Atractylodes japonica Koidz. The medicine is distinguished from bái zhú, which is typically cultivated, whereas cāng zhú more often tends to be collected from the wild. It is believed that the distinction between cāng zhú and bái zhú emerged in relatively modern times; a single drug "zhú" described in the Shen nong ben cao jing probably included many Atractylodes species.
Jatrorrhizine is a protoberberine alkaloid found in some plant species, such as Enantia chlorantha (Annonaceae). Synonyms that may be encountered include jateorrhizine, neprotin, jatrochizine, jatrorhizine, and yatrorizine.
Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a sterol. Originally described in the 1930s from the yeast Saccharomyces cerevisiae, it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some in vitro bioactive properties, including cytotoxicity to some mammalian cell lines.
Corydaline is an acetylcholinesterase inhibitor isolated from Corydalis yanhusuo.
(S)-Magnoflorine is a quaternary benzylisoquinoline alkaloid (BIA) of the aporphine structural subgroup which has been isolated from various species of the family Menispermaceae, such as Pachygone ovata,Sinomenium acutum, and Cissampelos pareira.
Corydalis yanhusuo is a plant species in the genus Corydalis. The Chinese name for Corydalis yanhusuo is yan hu suo. The Japanese common name is engosaku (エンゴサク) and the Korean common name is hyeonhosaek (현호색). English common names include yanhusuo, corydalis, and Asian corydalis. The tuber of this plant, frequently mislabeled as the root, is an important therapeutic agent in traditional Chinese medicine. It is native to high-altitude grasslands across China including in the provinces of Anhui, Henan, Hubei, Hunan, Jiangsu, and Zhejiang, but is more widely cultivated.
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