Abstract:Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids-dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-f… Show more
“…The furquinolone alkaloids isolated from T. crispa comprise tyramine (44) , higenamine (45) (Praman et al, 2012 ), N-cis- feruloyltyramine (46) , N - trans- feruloyltyramine (47) , paprazine (48) , and N - trans- caffeoyltyramine (49) (Naomichi et al, 1983 ; Chung, 2011 ). The protoberberine alkaloids include 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (50) , columbamine (51) , dihydrodiscretamin (52) (Yusoff et al, 2014 ), palmatine (53) , jatrorrhizine (54) (Sumimoto Chemicals Co Ltd, 1982 ), and berberine (55) (Bisset and Nwaiwu, 1983 ). Salsolinol (56) (a tetrahydroisoquinoline) and (−)-Litcubinine (57) (a dibenzopyrrocoline type alkaloid) were identified from n-butanol fraction of T. crispa stem (Praman et al, 2012 ).…”
Tinospora crispa (L.) Hook. f. & Thomson (Menispermaceae), found in the rainforests or mixed deciduous forests in Asia and Africa, is used in traditional medicines to treat numerous health conditions. This review summarizes the up-to-date reports about the ethnobotany, phytochemistry, pharmacological activities, toxicology, and clinical trials of the plant. It also provides critical assessment about the present knowledge of the plant which could contribute toward improving its prospect as a source of lead molecules for drug discovery. The plant has been used traditionally in the treatment of jaundice, rheumatism, urinary disorders, fever, malaria, diabetes, internal inflammation, fracture, scabies, hypertension, reducing thirst, increasing appetite, cooling down the body temperature, and maintaining good health. Phytochemical analyses of T. crispa revealed the presence of alkaloids, flavonoids, and flavone glycosides, triterpenes, diterpenes and diterpene glycosides, cis clerodane-type furanoditerpenoids, lactones, sterols, lignans, and nucleosides. Studies showed that the crude extracts and isolated compounds of T. crispa possessed a broad range of pharmacological activities such as anti-inflammatory, antioxidant, immunomodulatory, cytotoxic, antimalarial, cardioprotective, and anti-diabetic activities. Most pharmacological studies were based on crude extracts of the plant and the bioactive compounds responsible for the bioactivities have not been well identified. Further investigations are required to transform the experience-based claims on the use of T. crispa in traditional medicine practices into evidence-based information. The plant extract used in pharmacological and biological studies should be qualitatively and quantitatively analyzed based on its biomarkers. There should be detail in vitro and in vivo studies on the mechanisms of action of the pure bioactive compounds and more elaborate toxicity study to ensure safety of the plant for human use. More clinical trials are encouraged to be carried out if there are sufficient preclinical and safety data.
“…The furquinolone alkaloids isolated from T. crispa comprise tyramine (44) , higenamine (45) (Praman et al, 2012 ), N-cis- feruloyltyramine (46) , N - trans- feruloyltyramine (47) , paprazine (48) , and N - trans- caffeoyltyramine (49) (Naomichi et al, 1983 ; Chung, 2011 ). The protoberberine alkaloids include 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (50) , columbamine (51) , dihydrodiscretamin (52) (Yusoff et al, 2014 ), palmatine (53) , jatrorrhizine (54) (Sumimoto Chemicals Co Ltd, 1982 ), and berberine (55) (Bisset and Nwaiwu, 1983 ). Salsolinol (56) (a tetrahydroisoquinoline) and (−)-Litcubinine (57) (a dibenzopyrrocoline type alkaloid) were identified from n-butanol fraction of T. crispa stem (Praman et al, 2012 ).…”
Tinospora crispa (L.) Hook. f. & Thomson (Menispermaceae), found in the rainforests or mixed deciduous forests in Asia and Africa, is used in traditional medicines to treat numerous health conditions. This review summarizes the up-to-date reports about the ethnobotany, phytochemistry, pharmacological activities, toxicology, and clinical trials of the plant. It also provides critical assessment about the present knowledge of the plant which could contribute toward improving its prospect as a source of lead molecules for drug discovery. The plant has been used traditionally in the treatment of jaundice, rheumatism, urinary disorders, fever, malaria, diabetes, internal inflammation, fracture, scabies, hypertension, reducing thirst, increasing appetite, cooling down the body temperature, and maintaining good health. Phytochemical analyses of T. crispa revealed the presence of alkaloids, flavonoids, and flavone glycosides, triterpenes, diterpenes and diterpene glycosides, cis clerodane-type furanoditerpenoids, lactones, sterols, lignans, and nucleosides. Studies showed that the crude extracts and isolated compounds of T. crispa possessed a broad range of pharmacological activities such as anti-inflammatory, antioxidant, immunomodulatory, cytotoxic, antimalarial, cardioprotective, and anti-diabetic activities. Most pharmacological studies were based on crude extracts of the plant and the bioactive compounds responsible for the bioactivities have not been well identified. Further investigations are required to transform the experience-based claims on the use of T. crispa in traditional medicine practices into evidence-based information. The plant extract used in pharmacological and biological studies should be qualitatively and quantitatively analyzed based on its biomarkers. There should be detail in vitro and in vivo studies on the mechanisms of action of the pure bioactive compounds and more elaborate toxicity study to ensure safety of the plant for human use. More clinical trials are encouraged to be carried out if there are sufficient preclinical and safety data.
“…Clinical trials have indicated that berberine has been effective in improving the cardiac performance in patients with heart failure. It exerts direct depressive action on myocardial vasculature and smooth musculature [22] and may have anti-cholesterolase activity [23]. Recent clinical trials have shown that berberine has potential as a safe oral hypoglycemic agent to treat type II diabetes in patients with dyslipidemia [24].…”
Molecular damage of DNA plays an important role in the cell killing and several anti-neoplastic agents exert their cytotoxic effects by inducing DNA damage in the cancer cells. DNA damaging effect of various concentrations of berberine chloride (BCL), an isoquinoline alkaloid was studied in HeLa cells by alkaline comet assay. The DNA damage has been expressed as olive tail moment (OTM). Incubation of HeLa cells with BCL for 4 h showed greater amount of DNA damage (OTM) than 2 h treatment. BCL treatment caused a concentration dependent rise in the DNA damage in HeLa cells and exposure of HeLa cells with 1 µg/ml BCL caused a10 fold rise in baseline DNA damage, whereasa maximum rise in DNA damage was observed in HeLa cells exposed to 8 µg/ml BCL. The study of DNA repair kinetics at different BCL post-treatment times revealed a constant rise in the DNA damage in BCL treated cells up to 24 h except for 1 -4 µg/ml BCL, where the highest DNA damage was observed at 12 h post-BCL treatment. The clonogenic assay showed that BCL treatment resulted in a concentration dependent rise in its cell killing effect. The cell survival and molecular DNA damage in HeLa cells treated with BCL has an inverse correlation indicating that with increased DNA damage cell survival declined. Our study demonstrates that anti-neoplastic effect of BCL is mainly due to its ability to cause damage to the cellular genome.
A rapid hydrostatic counter-current chromatography–thin-layer chromatography–electrospray-ionization time-of-flight mass spectrometry (CCC–TLC–ESI-TOF-MS) technique was established for use in seeking potent anti-Alzheimer’s drugs among the acethylcholinesterase inhibitors in Argemone mexicana L. underground parts, with no need to isolate components in pure form. The dichloromethane extract from the roots of Mexican prickly poppy that was most rich in secondary metabolites was subjected to hydrostatic-CCC-based fractionation in descending mode, using a biphasic system composed of petroleum ether–ethyl acetate–methanol–water at the ratio of 1.5:3:2.1:2 (v/v). The obtained fractions were analyzed in a TLC-based AChE-inhibition “Fast Blue B” test. All active components in the fractions, including berberine, protopine, chelerithrine, sanguinarine, coptisine, palmatine, magnoflorine, and galanthamine, were identified in a direct TLC–HPLC–ESI-TOF-MS assay with high accuracy. This is the first time galanthamine has been reported in the extract of Mexican prickly poppy and the first time it has been identified in any member of the Papaveraceae family, in the significant quantity of 0.77 %.Graphical AbstractScreening platform of anti-AChE alkaloids
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