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PubMed2005

Isolation and identification of seven glucuronide conjugates of andrographolide in human urine.

Andrographolide is one of the principal components of a famous traditional Chinese herbal medicine, Andrographis paniculate (Burm) Nees, and has been widely used in the clinic for the treatment of infectious diseases. In this paper, metabolites of andrographolide in the urine of eight healthy volunteers after oral administration were further investigated. Building on previous findings, an additional seven phase II metabolites were isolated by liquid-liquid extraction, open-column chromatography, medium-pressure liquid chromatography, and, finally, preparative high-performance liquid chromatography. Structural elucidation was carried out by mass spectra and NMR spectroscopy including 1H NMR, 13C NMR and two-dimensional NMR (distortionless enhancement by polarization transfer, heteronuclear multiple-quantum correlation, heteronuclear multiple-bond correlation, 1H-1H correlated spectroscopy, and nuclear Overhauser enhancement spectroscopy). All of the metabolites were characterized as glucuronide conjugates, and the structures were determined to be andrographolide-19-O-beta-D-glucuronide (M-1), isoandrographolide-19-O-beta-D-glucuronide (M-2), 14-deoxy-12-hydroxy-andrographolide-19-O-beta-D-glucuronide (M-3), andrographolide-19-O-[6'-methyl-beta-D-glucuronide] (M-4), 14-deoxy-12(13)-en-andrographolide-19-O-beta-D-glucuronide (M-5), 14-deoxyandrographolide-19-O-beta-D-glucuronide (M-6), and 3-oxoandrographolide-19-O-beta-D-glucuronide (M-7), respectively.

Adult↗

PubMed2004

Andrographolide interferes with T cell activation and reduces experimental autoimmune encephalomyelitis in the mouse.

Andrographolide is a bicyclic diterpenoid lactone derived from extracts of Andrographis paniculata, a plant indigenous to South Asian countries that shows anti-inflammatory properties. The molecular and cellular bases for this immunomodulatory capacity remain unknown. Here, we show that andrographolide is able to down-modulate both humoral and cellular adaptive immune responses. In vitro, this molecule was able to interfere with T cell proliferation and cytokine release in response to allogenic stimulation. These results were consistent with the observation that T cell activation by dendritic cells (DCs) was completely abolished by exposing DCs to andrographolide during antigen pulse. This molecule was able to interfere with maturation of DCs and with their ability to present antigens to T cells. Furthermore, in vivo immune responses such as antibody response to a thymus-dependent antigen and delayed-type hypersensitivity were drastically diminished in mice by andrographolide treatment. Finally, the ability of andrographolide to inhibit T cell activation was applied to interfere with the onset of experimental autoimmune encephalomyelitis (EAE), an inflammatory demyelinating disease of the central nervous system that is primarily mediated by CD4(+) T cells and serves as an animal model for human multiple sclerosis. Treatment with andrographolide was able to significantly reduce EAE symptoms in mice by inhibiting T cell and antibody responses directed to myelin antigens. Our data suggest that andrographolide is able to efficiently block T cell activation in vitro, as well as in vivo, a feature that could be useful for interfering with detrimental T cell responses.

Animals↗

PubMed1989

Structure-activity correlation of flavonoids for inhibition of bovine lens aldose reductase.

To clarify the structure-activity correlation of flavonoids for inhibition of aldose reductase, about fifty flavonoid compounds were screened. The presence of hydrophobic substituents on the A ring and hydrophilic substituents on the B ring of the flavonoid skeleton was suggested to improve the potency of inhibitory activity. The activities of extracts of Scutellaria baicalensis, Andrographis paniculata and Gutierrezia microcephala are also described.

Aldehyde Reductase↗

PubMed2003

Heat-accelerated degradation of solid-state andrographolide.

The stability of andrographolide, the major active diterpene lactone from Andrographis paniculata (BURM. f.) WALL. ex NEES., was determined to show that, while crystalline andrographolide was highly stable even at 70 degrees C (75% relative humidity) over a period of 3 months, its amorphous phase degraded promptly. Heat-accelerated conditions revealed second-order kinetics of the decomposition with the rate constant at 25 degrees C (k(25 degrees C)) predicted from the Arrhenius plot of 3.8 x 10(-6) x d(-1). The major decomposed product under elevated temperature (70 degrees C, 75% relative humidity) is 14-deoxy-11,12-didehydroandrographolide.

Diterpenes↗

PubMed2004

Four new andrographolide metabolites in human urine.

Andrographolide is one of principal components of a famous traditional Chinese herbal medicine Andrographis paniculate (BURM) NEES. Four new metabolites of andrographolide were isolated from human urine. All of them were characterized as sulfate and one of them also as a cysteine S-conjugate. The structures were determined to be andrographolide-3-O-sulfate (M-1), isoandrographolide-3-O-sulfate (M-2), 14-deoxyandrographolide-3-O-sulfate (M-3), 14-deoxy-12-(cysteine-S-yl)-andrographolide-3-O-sulfate (M-4), respectively, based on chemical evidence and spectroscopic analyses.

Adult↗

PubMed2006

Complementary and alternative medicine for upper-respiratory-tract infection in children.

PURPOSE: Evidence on the efficacy and safety of complementary and alternative medicine (CAM) for the prevention and treatment of upper-respiratory-tract infection (URTI) in children is reviewed. SUMMARY: A search of the literature to June 2005 identified six clinical trials examining the use of herbal medicines and nine trials of other CAM therapies. All articles were critically evaluated for adherence to standards of efficacy and safety research. Echinacea did not reduce the duration and severity of URTI. Andrographis paniculata or echinacea decreased nasal secretions (p < 0.01) but not URTI symptoms. A combination of echinacea, propolis, and ascorbic acid decreased the number of URTI episodes, the duration of symptoms, and the number of days of illness (p < 0.001). Echinacea was associated with a higher frequency of rash compared with placebo (p = 0.008). Neither ascorbic acid nor homeopathy was effective. The efficacy of zinc was not clear, and zinc may be associated with adverse effects in children. Osteopathic manipulation decreased episodes of acute otitis media (p = 0.04) and the need for tympanostomy tube insertion (p = 0.03) in children with recurrent acute otitis media. Stress-management therapy reduced the duration of URTI compared with relaxation therapy with guided imagery or standard care (p < 0.05). CONCLUSION: Current data are generally inadequate to support CAM for the prevention or treatment of URTI in children.

Child↗

PubMed1991

Dehydroandrographolide succinic acid monoester as an inhibitor against the human immunodeficiency virus.

Dehydroandrographolide succinic acid monoester (DASM) is the dehydroandrographolyl ester of succinic acid; and andrographolide, from which DASM is made, is the major diterpenoid lactone found in the Chinese medicinal herb, Andrographis paniculata. DASM has been found to be an inhibitor against the human immunodeficiency virus (HIV) in vitro. It was nontoxic to the H9 cell at the concentrations of 50-200 (average, 108) micrograms/ml and was inhibitory to the HIV-1 (IIIB) at the minimal concentration of 1.6-3.1 (average 2.0) micrograms/ml. It was also inhibitory to two other strains of HIV-1 and a strain of HIV-2. This inhibitory effect could also be demonstrated in cultures of activated human blood mononuclear cells; the 50% toxic dose and the 50% HIV inhibitory dose were about 200-greater than or equal to 400 and 0.8-2 micrograms/ml, respectively. At the subtoxic concentration, DASM partially interfered with HIV-induced cell fusion and with the binding of HIV to the H9 cell. Presumably, it also interfered with HIV replication at another unidentified step(s).

Antiviral Agents↗

PubMed2004

Andrographolide attenuates inflammation by inhibition of NF-kappa B activation through covalent modification of reduced cysteine 62 of p50.

NF-kappaB is a central transcriptional factor and a pleiotropic regulator of many genes involved in immunological responses. During the screening of a plant extract library of traditional Chinese herbal medicines, we found that NF-kappaB activity was potently inhibited by andrographolide (Andro), an abundant component of the plant Andrographis that has been commonly used as a folk remedy for alleviation of inflammatory disorders in Asia for millennia. Mechanistically, it formed a covalent adduct with reduced cysteine (62) of p50, thus blocking the binding of NF-kappaB oligonucleotide to nuclear proteins. Andro suppressed the activation of NF-kappaB in stimulated endothelial cells, which reduced the expression of cell adhesion molecule E-selectin and prevented E-selectin-mediated leukocyte adhesion under flow. It also abrogated the cytokine- and endotoxin-induced peritoneal deposition of neutrophils, attenuated septic shock, and prevented allergic lung inflammation in vivo. Notably, it had no suppressive effect on IkappaBalpha degradation, p50 and p65 nuclear translocation, or cell growth rates. Our results thus reveal a unique pharmacological mechanism of Andro's protective anti-inflammatory actions.

Active Transport, Cell Nucleus↗

PubMed2006

Medicinal plant extracts as anti-Escherichia coli O157:H7 agents and their effects on bacterial cell aggregation.

Ethanolic extracts of eight Thai medicinal plants (representing five families) that are used as traditional remedies for treating diarrhea were examined with a salt aggregation test for their ability to modulate cell surface hydrophobicity of enterohemorrhagic Escherichia coli strains, including E. coli O157:H7. Four of these medicinal plants, Acacia catechu, Peltophorum pterocarpum, Punica granatum, and Quercus infectoria, have high bacteriostatic and bactericidal activities. The ethanolic extract of Q. infectoria was the most effective against all strains of E. coli, with MICs of 0.12 to 0.98 mg/ml and MBCs of 0.98 to 3.91 mg/ml. The ethanolic extract of P. granatum had MICs of 0.49 to 1.95 mg/ml and MBCs of 1.95 to 3.91 mg/ml. Ethanolic extracts of Q. infectoria, P. pterocarpum, and P. granatum were among the most effective extracts against the two strains of E. coli O157:H7. The other four plants, Andrographis paniculata, Pluchia indica, Tamarindus indica, and Walsura robusta, did not have high bacteriostatic and bactericidal activities but were able to affect hydrophobicity characteristics on their outermost surface. All plants except Q. infectoria had some ability to increase cell surface hydrophobicity. There appears to be no correlation between antibacterial activity and cell aggregative properties.

Acacia↗

PubMedDate not supplied

In vitro evaluation of inhibitory nature of extracts of 18-plant species of Chhindwara against 3-keratinophilic fungi.

Effect of extract of 18 plant species, viz., Acorus calamus, Adhatoda vasica, Amomum subulatum, Andrographis paniculata, Boerhaavia diffusa, Cassia occidentalis, Centella asiatica, Cymbopogon citratus, Hemidesmus indicus, Hyptis suaveolens, Malvestrum sp., Passiflora edulis, Pergularia daemia, Peristrophe bicalyculata, Shuteria hirsuta, Solanum nigrum, Tecoma stans, and Verbascum chinense on the growth of Microsporum gypseum, Chrysosporium tropicum and Trichophyton terrestre was evaluated and discussed. The sensitivity of the keratinophilic fungi was evaluated by dry-weight method. The maximum inhibition of mycelial growth was shown by M. gypseum (86.62%) followed by T. terrestre (81.86%) and C. tropicum (74.06%) when treated with S. hirsuta whereas the minimum inhibition was exhibited by M. gypseum (0.29%), C. tropicum (0.16%) and T. terrestre (1.76%) when tested with the extract of P. edulis, A. vasica and B. diffusa respectively.

Antifungal Agents↗

PubMedDate not supplied

Screening of indigenous plants for anthelmintic action against human Ascaris lumbricoides: Part--II.

Alcoholic extracts of the rhizomes of Alpinia galanga, Andrographis paniculata, bark of Cinnamomum zeylanicum, rind of Citrus decumana, Desmodium triflorum, seeds of Hydnocarpus wightiana, rhizomes of Kaempfaria galanga, Lippia nodiflora, tender leaves of Morinda citrifolia, rhizomes of Pollia serzogonian, Tephrosia purpuria and rhizomes of Zingiber zerumbeth showed good in vitro anthelmintic activity against human Ascaris lumbricoides. While, the alcoholic extracts of the bark of Alibzzia lebbek, the bulb of Allium sativum, rhizomes of Alpinia calcaratta, rind of Citrus acida, rind of Citrus aromatium, rind of Citrus medica, rhizomes of Curcuma aromatica and rind of Punica granatum showed moderate invitro activity.

Animals↗

PubMed2001

An experimental study of some indigenous drugs with special reference to hydraulic permeability.

The effect of commonly used indigenous drugs for hepatic disorders i.e. Tinospora cordifolia, (Guduchi/Amrita), Andrographis paniculata (Kalmegha), Picrorhiza kurroa (Kutki), Phyllantnus niruri (Bhoomyamalaki) and Berberis aristata (Daruharidra) was tested on the hydraulic permeability of water in the presence of bile salt through a transport cell model. The data on hydraulic permeability were calculated as t (time). JV = Lp x AP, where Lp = hydraulic conductivity and AP is the pressure difference. It was observed that the value of controlled hydraulic permeability (0.49 x 10(-8) M3 S(-1) N(-1)) decreased in the presence of indigenous drugs and bile salt. The results suggest that these drugs might have the cell membrane stabilizing property which may lead to prevention of the toxic effect of bile salts in various hepatic disorders.

Humans↗

PubMed2001

Herbal preparations as a source of hepatoprotective agents.

Mono- and polyherbal preparations with potent antihepatotoxic activity in various liver disorders, made from traditionally used herbs with proven efficacy, have been described. More than 700 mono- and polyherbal preparations in the form of decoction, tincture, tablets and capsules from more than 100 plants are in clinical use. Some of the herbs--such as Silybum marianum, Picrorhiza kurroa, Andrographis paniculata and Glycyrrhizae radix--are very common in most of the polyherbal preparations. This review covers the preparations of widely used herbs such as S. marianum, Schisandra chinensis, Phyllanthus amarus, P. kurroa, A. paniculata, G. radix, Lycium chinense and Cochlospermum tinctorium as hepatoprotectants and includes the mode of action of these preparations. Some polyherbal preparations such as Livex, HD-03, Hepatomed and Hepatoguard with proven efficacy are also described in this review.

Journal Article↗

PubMed2003

A randomized, controlled study of Kan Jang versus amantadine in the treatment of influenza in Volgograd.

Two randomized, parallel-group clinical studies with a verum and a control group were performed to investigate the effect of a standardized extract (SHA-10) of Andrographis panaiculata (N.) fixed combination Kan Jang in the treatment of diagnosed influenza viral infection. The pilot study was performed on 540 patients with 71 Kan Jang-treated patients with the second phase conducted enrolling 66 patients. The differences in the duration of sick leave and frequency of post-influenza complications indicate that the Kan Jang phytopreparation not only contributes to quicker recovery, but also reduces the risk of post-influenza complications. Kan Jang was well tolerated by patients.

Clinical Trial↗

PubMedDate not supplied

Morphological and biochemical changes of andrographolide-induced cell death in human prostatic adenocarcinoma PC-3 cells.

Andrographolide was extracted and purified from Andrographis panicula using hexane and water partitioning followed by ethyl acetate extraction and chromatography. It showed selective cytotoxicity to prostate cancer PC-3 cells in vitro. The morphological and biochemical changes induced by the extract in carcinoma PC-3 cell death were studied. In andrographolide-treated cells, evidence of apoptosis such as cell shrinkage and surface microvilli loss after 4-hour treatment and chromatin condensation and fragmentation in H&E-stained cells between 4 to 8 hours after treatment were observed. Under electron microscopy, membrane blebbing and apoptotic bodies formation were seen after 8-hour treatment. Using immunocytochemistry staining and cellular caspase-3 activity assay, andrographolide-treated cells showed considerable caspase-3 activation and caspase-8 in PC-3 cells at 4 and 2 hours after treatment, respectively. This suggests andrographolide-induced cell death was achieved through the apoptotic pathway, via the activation of an extrinsic caspase cascade.

Adenocarcinoma↗

PubMed2005

In vitro screening of five local medicinal plants for antibacterial activity using disc diffusion method.

Medicinal plants have many traditional claims including the treatment of ailments of infectious origin. In the evaluation of traditional claims, scientific research is important. The objective of the study was to determine the presence of antibacterial activity in the crude extracts of some of the commonly used medicinal plants in Malaysia, Andrographis paniculata, Vitex negundo, Morinda citrifolia, Piper sarmentosum, and Centella asiatica. In this preliminary investigation, the leaves were used and the crude extracts were subjected to screening against five strains of bacteria species, Methicillin Resistant Staphylococcus aureus (MRSA), Staphylococcus aureus, Klebsiella pneumoniae, Pseudomonas aeruginosa and Escherichia coli, using standard protocol of Disc Diffusion Method (DDM). The antibacterial activities were assessed by the presence or absence of inhibition zones and MIC values. M. citrifolia, P. sarmentosum and C. asiatica methanol extract and A. paniculata (water extract) have potential antibacterial activities to both gram positive S. aureus and Methicillin Resistant S. aureus (MRSA). None of the five plant extracts tested showed antibacterial activities to gram negative E. coli and K. pneumoniae, except for A. paniculata and P. sarmentosum which showed activity towards P. aeruginosa. A. paniculata being the most potent at MIC of 2 g/disc. This finding forms a basis for further studies on screening of local medicinal plant extracts for antibacteria properties.

Anti-Bacterial Agents↗

PubMed1990

Hepatoprotective activity of andrographolide against galactosamine & paracetamol intoxication in rats.

Hepatoprotective effect of andrographolide (the major active diterpenoid lactone of the plant Andrographis paniculata) was studied on acute hepatitis induced in rats by single dose of galactosamine (800 mg/kg, ip)/paracetamol (3g/kg, po). Hepatoprotective activity was monitored by estimating the serum transaminases (GOT and GPT), alkaline phosphatase and bilirubin in serum, hepatic triglycerides, and by histopathological changes in the livers of experimental rats. Pre-treatment and/or post-treatment of rats at different time intervals with different doses of andrographolide in the two experimental models of hepatotoxicity showed that treatment of rats with 400 mg/kg, ip or 800 mg/kg, po, 48, 24 and 2 h before galactosamine administration or with 200 mg/kg, ip, 1, 4 and 7 h after paracetamol challenge leads to complete normalisation of toxin-induced increase in the levels of all the five biochemical parameters, and significantly ameliorates toxin-induced histopathological changes in the livers of experimental rats. The results confirmed the in vivo hepatoprotective effect of andrographolide against galactosamine or paracetamol-induced hepatotoxicity in rats. Since the protective effect of andrographolide was observed in two types of intoxication, which are very different in their primary mechanism of inducing hepatotoxicity, it is suggested that protective mechanisms of andrographolide which are not specific to galactosamine or paracetamol toxicity may be responsible for the hepatoprotective activity of the compound.

Acetaminophen↗

PubMed1990

In vitro studies on the effect of certain natural products against hepatitis B virus.

Picroliv (active principle from Picrorrhiza kurroa), its major components picroside I, catalpol, kutkoside I, kutkoside, andrographolide (active constituent of Andrographis paniculata), silymarin and Phyllanthus niruri extract were tested for the presence of anti hepatitis B virus surface antigen (anti HBs) like activity. HBsAg positive serum samples obtained from hepatitis B virus (HBV) associated acute and chronic liver diseases and healthy HBsAg carriers were used to evaluate the anti-HBs like activity of compounds/extract. The latter were mixed with serum samples and incubated at 37 degrees C overnight followed by HBsAg screening in the Elisa system. A promising anti-HBsAg like activity was noted in picroliv (and its major components) catalpol, P. niruri which differed from the classical viral neutralization. Picroliv also inhibited purified HBV antigens (HBsAg and HBsAg) prepared from healthy HBsAg carriers. The in vitro testing system appears to be a suitable model to identify an agent active against HBV, prior to undertaking detailed studies.

Adult↗