Diterpenoids as potential anti-malarial compounds from Andrographis paniculata (original) (raw)
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Future Journal of Pharmaceutical Sciences, 2021
Andrographis paniculata is a well-known medicinal plant that contains various classes of bioactive secondary metabolites. It is widely used by the traditional medicinal healers for treatment of malaria and other diseases. There is an urgent need for screening of potent novel compounds from the methanol extract of A. paniculata. Earlier, we obtained appreciable in vitro anti-malarial activity (IC50-10.75 μg/ml) in the same plant. In current study, we developed novel analytical methods for rapid identification and characterization of diterpenes and flavones using chromatographic and spectroscopic techniques and identified major compounds that might possess anti-malarial activities. Based on the chromatographic and mass spectrometric features, we have identified a total of 74 compounds (25 compounds from positive ion mode; 49 compounds from negative ion mode). The mass spectrum data predicted andrographolide (15%) presence in the highest amount in both positive and negative ion modes. ...
Diterpenoids and Flavonoids from Andrographis paniculata
Chemical and Pharmaceutical Bulletin, 2020
Chemical investigation of the aerial parts of Andrographis paniculata resulted in isolation of nine compounds, including a new ent-labdane diterpenoid, andrographic acid methyl ester (1), a new chalcone glucoside, pashanone glucoside (5), and seven known metabolites, andrograpanin (2), andrographolide (3), andropanolide (4), andrographidine A (6), andrographidine F (7), 6-epi-8-O-acetyl-harpagide (8), and curvifloruside F (9). Their chemical structures were elucidated based on comprehensive analyses of the spectroscopic data, including NMR and MS. Among the isolated compounds, andropanolide exerted cytotoxicity toward LNCaP, HepG2, KB, MCF7, and SK-Mel2 carcinoma cells, with IC 50 values ranging from 31.8 to 45.9 µM. In addition, andropanolide significantly inhibited the overproduction of nitric oxide (NO) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with an IC 50 value of 13.4 µM.
Since the emergence of drug resistant strains of malaria parasites, the rate of resistance has been increasing and limiting adequate treatment of malaria. Consequently, there is an urgent global need to isolate new classes of antimalarial compounds from natural sources. The aim of this study was to test Andrographis paniculata extract for the ability to treat malaria. The Andrographis paniculata powder from commercial capsule was freshly dissolved in DMSO and diluted with normal saline. The four-day suppressive, curative effects against established infection and prophylactic models of the extract were carried out in P. berghei ANKA infected ICR mice, using pyrimethamine as a positive control. Parasitemia was then monitored at day 4 after treatment with the extracts (suppressive and curative tests) or after infection (prophylactic test), and percent inhibition was subsequently calculated and compared with pyrimethamine treated group. It was found that the extract (2, 20, and 100 mg.k...
In vivo Antimalarial Activity of Andrographis Paniculata Tablets
Procedia Chemistry, 2014
The formulation of three phytopharmaceutical products of Andrographispaniculata fractions (AP fraction A and B) containing diterpene lactones as an active substance were developed and their antimalarial activities against Plasmodium bergheihas been examined. In vivo antimalarial assay on P. berghei infected mice was carried out by oral administration,twice a dayfor four consecutive days of the AP fractions product, which were Tablet I : wet granulated formula of AP fraction A; Tablet II : wet granulated formula of AP fraction B; Tablet III : solid dispersion formula of AP fraction B.. The results revealed that three phytopharmaceutical products of A.paniculata were inhibited parasite's growth with inhibition range of 70.15% to 80.35%. There was no significant difference of antimalarial activities between Tablet II and III, meanwhile there was significant difference among Tablet I with Tablet II and Tablet III.It was concluded that antimalarial activity depending on raw material form of A. paniculata active substance.
2011
The main objective of the investigation was to optimize a suitable extraction method and to isolate and characterize the compound obtained from the leaves of Andrographis paniculata (Burm. F.) Nees (Acanthaceae). Preliminary phytochemical screening of the various extracts of the leaves revealed the presence of flavones and terpenoids in them. The active compound was isolated and identified by its melting point (227°C) and TLC analysis. Rf values of test sample was found to be 0.64 and that of standard was 0.65 in solvent system chloroform : methanol (7:1). The maximum absorbance (λmax) of the active compound was found to be 224 nm. From the FTIR graph the compound was found to possess an asymmetric -CH stretch of -CH3 at 2977.89, an asymmetric -CH at 2848.78, an asymmetric =CH2 stretch at 2927, a free OH group attached to the lactone ring demonstrating a peak at 3398.34, a C=C bond of the diterpene ring demonstrating a peak at 1456.16, a O-C=O group in the lactone ring at 1356.12, w...
Isolation and identification of bioactive compounds in Andrographis paniculata (Chuanxinlian)
Chinese Medicine, 2010
Andrographis paniculata (Burm. f.) Nees (Acanthaceae) is a medicinal plant used in many countries. Its major constituents are diterpenoids, flavonoids and polyphenols. Among the single compounds extracted from A. paniculata, andrographolide is the major one in terms of bioactive properties and abundance. Among the andrographolide analogues, 14-deoxy-11,12-didehydroandrographolide is immunostimulatory, anti-infective and anti-atherosclerotic; neoandrographolide is anti-inflammatory, anti-infective and anti-hepatotoxic; 14-deoxyandrographolide is immunomodulatory and anti-atherosclerotic. Among the less abundant compounds from A. paniculata, andrograpanin is both anti-inflammatory and anti-infective; 14-deoxy-14,15-dehydroandrographolide is antiinflammatory; isoandrographolide, 3,19-isopropylideneandrographolide and 14-acetylandrographolide are tumor suppressive; arabinogalactan proteins are anti-hepatotoxic. The four flavonoids from A. paniculata, namely 7-Omethylwogonin, apigenin, onysilin and 3,4-dicaffeoylquinic acid are anti-atherosclerotic. Background Andrographis paniculata (Burm. f.) Nees (Acanthaceae) (A. paniculata, Chuanxinlian), native to Taiwan, Mainland China and India, is a medicinal herb with an extremely bitter taste used to treat liver disorders, bowel complaints of children, colic pain, common cold and upper respiratory tract infection [1-3]. The aerial part of A. paniculata is commonly used in Chinese medicine. According to Chinese medicine theory, A. paniculata 'cools' and relieves internal heat, inflammation and pain and is used for detoxication [4-6]. The herb contains diterpenoids, flavonoids and polyphenols as the major bioactive components [7,8]. This article reviews the constituents and pharmacological properties of A. paniculata, including its chemical components, biological activities and possible mechanisms. The literature search was conducted in Pubmed database (1984-2010), focused on language literature in English. The keywords used were selected from andrographolide, A. paniculata and its compounds with bioactivities. In comparison with other Chinese medicinal herbs, this well studied herb not only shows a wide variety of health benefits, but many bioactive compounds are also being identified. Furthermore, several derivatives have been semisynthesized to enhance their bioactivity than original compounds, suggesting a potential for drug development. The authors read more than 200 full articles and a total of 124 peer-reviewed papers focused on anti-inflammation, anti-cancer, immunomodulation, anti-infection, antihepatotoxicity, anti-atherosclerosis, anti-diabetes and anti-oxidation were selected for this review. Bioactive constituents Active compounds extracted with ethanol or methanol from the whole plant, leaf and stem [9-11] include over 20 diterpenoids and over ten flavonoids have been reported from A. paniculata [12,13]. Andrographolide (C 20 H 30 O 5) is the major diterpenoid in A. paniculata, making up about 4%, 0.8~1.2% and 0.5~6% in dried whole plant, stem and leaf extracts respectively [9,11,14]. The other main diterpenoids are deoxyandrographolide, neoandrographolide, 14-deoxy-11,12-didehydroandrographide and isoandrographolide [9,15] (Table 1, Figure 1). From ethyl acetate (EtOA C)-soluble fraction of the ethanol or methanol extract, 5-hydroxy-7,8-dimethoxyflavone, 5
Identification of Medicinal Organic Components of Andrographis paniculata Leaf Extracts
Pakistan journal of scientific and industrial research, 2020
Active metabolites of methanol, ethanol, ethyl acetate and aqueous extracts of the leaves of Andrographis paniculata were identified using thin layer chromatography and gas chromatography-mass spectrometry (GC-MS). Results from this study identified some of active metabolites as andrographolide, 14-deoxyandrographolide, neoandrographolide, 14-deoxy-11,12-di-dehydroandrographolide, andrographanin, isoandrographolide, 14-acetylandrographolide, 19-O-andrographolide, beta-sitosterol and 14-deoxy-14,15dihydroandrographolide. Ethanol was a more effective solvent for the extraction as most of the phytochemicals were identified in this extract. Research had shown that extracts from the leaves of the plant possess a lot of therapeutic properties such as anti-microbial, anti-inflammatory, anti-diabetic, immune modulatory and antimalarial activities which are of immense benefit to man.
Background: Many medicinal plants have wide range of applications from food and aesthetic materials to pharmacological effect on various disease conditions. Traditionally, these plants have been used to treat many diseases including diabetes, inflammation, upper respiratory tract infections and diarrhoea either in single or combined form with other plant parts or materials. Objective: This study investigated the isolation and characterisation of andrographolide from Andrographis paniculata (Burm. f) Wall. ex Nees. Methodology: The isolation of the constituents was done using column total flavonoid conducted while the analysis was done using ultraviolet, infrared spectrum analysis (UV, IR), melting point and elemental analysis. Also, proton and carbon nuclear magnetic resonance (1 H and 13 C NMR) of the isolated compound was performed using different equipment. Results: Although, the total flavonoid content was low, ethyl acetate extract indicated the highest total flavonoids content and it's statistically different from methanol, ethanol: water (1:1 v/v) and aqueous extracts. The compound obtained is colorless solid with melting point range of 228 o C-238 o C. This was further supported by 13 C NMR spectral analysis, which displayed 20 signals for all carbon atoms and is like standard compound Andrographolide. Also, the ultraviolet analysis suggesting α, β-unsaturated lactone ring similar andrographolide while the elemental analysis shows the different elements present. Conclusion: Different extracts of A. paniculata exhibit multiple pharmacological effects. However, due to the much similarities with the isolated compound and Andrographolide the compound is suggested to be Andrographolide.
Nowadays, research on medicinal plants has attracted a lot of attention globally. A number of evidence has been accumulated to demonstrate promising potential of medicinal plants used in various traditional, complementary, and alternative systems. In recent years, a medicinal plant, Andrographis paniculata, and its major active phytochemicals have been extensively studied for several pharmacological activities. To understand the mechanism of action, researches have to be carried out at molecular levels. The present review aims at compiling consequential compendium of pharmacological benefits of health on this plant and its major diterpenoid constituent andrographolide that have been tested in various experimental models using modern scientific methodologies.
Asian Pacific Journal of Health Sciences
Antimalarial effect of some medicinal plants found in Uttarakhand (India) is least explored by the scientific community locally. Advent of resistance to various antimalarial drugs by plasmodium made malaria more fatal and life-threatening disease. Therefore, present need is to invest more effort and interest in research for antimalarials from medicinal plants. Plasmodium yoelii nigeriensis (PYn) is multi drug resistance malaria parasite known for resistance to chloroquine (CQ), quinine, quinidine, amodiaquine, halofantrine, mepacrine, and mefloquine. The P. yoelii produces 100% infections in animals. Researchers in this study tried to understand the behavior of CQ -resistant plasmodium PYn with CQ, whole plant extracts of Andrographis paniculata (AP) with possibility of their resistance reversal. Wherever, 3–4 times CQ doses are not able to produce sufficient antimalarial effect in resistant PYn. Most of the pure plant extracts are also not able to produce minimal therapeutic respon...