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PubMed2001

Antileishmanial activity of hydrolyzable tannins and their modulatory effects on nitric oxide and tumour necrosis factor-alpha release in macrophages in vitro.

A series of 27 hydrolyzable tannins and related compounds was tested for antiparasitic effects against both extracellular promastigote and intracellular amastigote Leishmania donovani organisms. In parallel, the compounds were evaluated for their immunomodulatory effects on macrophage functions, including release of nitric oxide (NO), tumour necrosis factor-alpha (TNF-alpha) and interferon (IFN)-like properties using several functional assays. Of the series of polyphenols tested, only gallic acid (54 microM NO) and its methyl ester (32 microM NO) induced murine macrophage-like RAW 264.7 cells to release NO in appreciable amounts (IFN-gamma/LPS 119 microM NO). The in vitro TNF-inducing potential of the polyphenols examined increased in the order of oligomeric ellagitannins (EC(50) > 25 microg/ml) < monomeric ellagitannins, gallotannins (EC(50) 8.5 to > 25 microg/ml) < C-glucosidic ellagitannins, dehydroellagitannins (EC(50) 0.6 - 2.8 microg/ml) at the host cell subtoxic concentration of 50 microg/ml. Furthermore, promastigotes of Leishmania donovani were assayed in the presence of these polyphenols and the results showed that none of the compounds was significantly toxic (EC(50) > 25 microg/ml) to the extracellular forms. In contrast, all polyphenols showed pronounced antileishmanial activities (EC(50) < 0.4 - 12.5 versus 7.9 microg/ml for Pentostam) against intracellular amastigotes of L. donovani residing within RAW cells. Noteworthy, most compounds exhibited low cytotoxicity against the murine host cells (EC(50) >25 microg/ml). Furthermore, some ellagitannins and the majority of dehydroellagitannins induced potent interferon-like activities as reflected by inhibition of the cytopathic effect of encephalomyocarditis virus on fibroblast L929 cells. This is the first report on hydrolyzable tannins as a new class of natural products with leishmanicidal activity including their potential for inducing the release of NO, TNF and IFN-like activity in macrophage-like RAW cells.

Animals↗
PubMed2002

Pharmacologically active ellagitannins from Terminalia myriocarpa.

A new ellagitannin, methyl (S)-flavogallonate (14) along with fourteen known compounds, gallic acid, methyl gallate, ethyl gallate, 2,3-di-O-[( S)-4,5,6,4',5',6'-hexahydroxybiphenyl-2,2'-diyldicarbonyl]-(alpha/beta)-D-glucopyranose (4), vitexin, isovitexin, orientin, iso-orientin, kaempferol 3-O-beta-D-rutinoside, rutin, neosaponarin, ellagic acid, flavogallonic acid (13), and (alpha/beta)-punicalagin (15) have been isolated from the leaves of Terminalia myriocarpa Heurck. Protective effect of the major and structurally related compounds 4, 13, 15 and the new compound 14 against CCl 4 -induced hepatotoxicity has been evaluated and compared, using adult male rats weighing 200-250 g. Serum levels of glutamic oxaloacetic transaminase (GOT), glutamic pyruvic transaminase (GPT), lipid peroxide and nitric oxide production were significantly increased by administration of CCl 4 to rats and then reduced significantly only by treatment with compounds 4, 14 and 15 in a dose-dependent manner. Comparison of the protective properties of these compounds showed that compound 14 is more potent than compound 15 than 4 and that compound 13 has a non-significant effect at the used two dose levels.

Alanine Transaminase↗
PubMed2002

Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells.

The methanol extract of heartwood of Cercidiphyllum japonicum (Cercidiphyllaceae) stimulated proliferation of mouse hair epithelial cells, similar to minoxidil and procyanidin B-2. (+)-Taxifolin ( 2), quercetin ( 3), myricetin ( 4), (+)-dihydromyricetin ( 5) and gallic acid ( 6) were isolated from C. japonicum and showed significant proliferative activities on the hair epithelial cells.

Animals↗
PubMed2006

Antiplasmodial activity of compounds from Sloanea rhodantha (Baker) Capuron var. rhodantha from the Madagascar rain forest.

Bioassay-directed separation of the butanol-soluble portion of an extract of Sloanea rhodantha (Baker) Capuron var. Rhodantha (Elaeocarpaceae) active against the drug-sensitive HB3 strain of Plasmodium falciparum led to the isolation of seven phenolic compounds, gallic acid (1), 3,5-di-O-galloylquinic acid (2), 1,6-di-O-galloyl glucopyranoside (3), 3,4,5-tri-O-galloylquinic acid (4), 1-O-eudesmoylquinic acid (5), 1,2,3,6-tetra-O-galloyl glucopyranoside (6), and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-b-D-glucopyranoside (7). The structure of the new compound 5 was established on the basis of interpretation of its 1D and 2D NMR spectroscopic data. Compounds 2, 3, 4, 6, and 7 showed weak inhibitory activity against the drug-sensitive HB3 and the drug-resistant FCM29 strains of P. falciparum, with IC (50) values ranging from 8.0 - 43.0 and 16.1 - 93.0 microg/mL, respectively.

Animals↗
PubMed1997

Antibacterial activity of extracts and constituents of Pelargonium sidoides and Pelargonium reniforme.

The antibacterial activity of extracts and isolated constituents (scopoletin, umckalin, 5,6,7-trimethoxycoumarin, 6,8-dihydroxy-5,7-dimethoxycoumarin, (+)-catechin, gallic acid and its methyl ester) of Pelargonium sidoides and Pelargonium reniforme (Geraniaceae), plant species used in folk medicine by the Southern African native population, was evaluated against 8 microorganisms, including 3 Gram-positive (Staphylococcus aureus, Streptococcus pneumoniae, and beta-hemolytic Streptococcus 1451) and 5 Gram-negative bacteria (Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Haemophilus influenzae). Minimum inhibitory concentrations (MICs) varied with the preparation of the extracts and microorganisms tested, from about 0.6 mg/ml for aqueous phases to over 10 mg/ml for crude Pelargonium extracts. With the exception of the ineffective (+)-catechin, all the potentially active compounds exhibited antibacterial activities with MICs of 200-1000 micrograms/ml. The results provide for a rational basis of the traditional use of the titled Pelargonium species.

Anti-Bacterial Agents↗
PubMed1992

Procyanidin Production by Fagopyrum esculentum Callus Culture.

FAGOPYRUM ESCULENTUM CALLUS cultures grown on B5 medium synthesize procyanidins B2 (0.6-1.8 mg/g dry wt) and B2-3'- O-gallate (3.5-6.0 mg/g dry wt). Sucrose is a better source than other carbohydrates and moderate concentrations (3-4%) stimulate both growth and procyanidin synthesis. While darkness was not a limiting factor, light induced faster growth and increased procyanidin contents. Treatment with gallic acid strongly stimulated the procyanidin B2-3'- O-gallate production, but drastically inhibited growth, leading to a two-step-culture experiment combining convenient growth and increased galloylated dimer synthesis (up to 45 mg/g dry wt).

Journal Article↗
PubMed1992

Antihepatotoxic C-glycosylflavones from the leaves of Allophyllus edulis var. edulis and gracilis.

From the leaves of Allophyllus edulis var. edulis and Allophyllus edulis var. gracilis nine C-glycosylflavones have been isolated and identified as schaftoside (8), vicenin-2 (9), lucenin-2 (10), isovitexin 2"-O-rhamnoside (11), cerarvensin 2"-O-rhamnoside (12), vitexin 2"-O-rhamnoside (13), isoorientin 2"-O-rhamnoside (15), orientin 2"-O-rhamnoside (16) and saponarin (17). In addition, gallic acid (2), the phenol C-glycosides bergenin (3) and 11-O-galloylbergenin (4), three flavonol 3-O-rhamnosides and a new C-glycosylflavone identified as mollupentin 2"-O-rhamnoside (14) were obtained from the leaves of Allophyllus edulis var. edulis. Their structures were elucidated on the basis of chemical and spectral data. For the first time the C-glycosylflavones were found to have remarkable anti-hepatotoxic activities against CCl4 and galactosamine cytotoxicity in primary cultured rat hepatocytes. Structure-activity relationships are discussed.

Animals↗
PubMed2001

Human hepatitis C virus NS5A protein alters intracellular calcium levels, induces oxidative stress, and activates STAT-3 and NF-kappa B.

The nonstructural protein 5A (NS5A) encoded by the human hepatitis C virus RNA genome is shown here to induce the activation of NF-kappaB and STAT-3 transcription factors from its cytoplasmic residence via oxidative stress. NS5A causes the disturbance of intracellular calcium. Ca2+ signaling triggers the elevation of reactive oxygen species in mitochondria, leading to the translocation of NF-kappaB and STAT-3 into the nucleus. Evidence is presented for the constitutive activation of STAT-3 by NS5A. In the presence of antioxidants [pyrrolidine dithiocarbamate (PDTC), N-acetyl l-cysteine (NAC)] or Ca2+ chelators (EGTA-AM, TMB-8), NS5A-induced activation of NF-kappaB and STAT-3 was eliminated. These results provide an insight into the mechanism by which NS5A can alter intracellular events relevant to liver pathogenesis associated with the viral infection.

Acetylcysteine↗
PubMed2003

Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical.

A 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-generating system was used to evaluate the antioxidant properties of Korean medicinal plants that have been used widely as folk medicines for several disorders, as well as compounds isolated from them. Among the Rosaceae, Rosa rugosa and Rosa davurica showed strong DPPH radical-scavenging activity. The most effective medicinal plant from families other than Rosaceae was Cedrela sinensis, followed in order by Nelumbo nucifera, Eucommia ulmoides, Zanthoxylum piperitum, Cudrania tricuspidata and Houttuynia cordata. These results serve as a good index of the free radical-scavenging activities of Korean medicinal plants. Furthermore, the polyphenols isolated from these plants, procyanidin B-3, (+)-catechin, gallic acid, methyl gallate, quercetin, quercetin-3-O-beta-D-glucoside, quercetin-3-O-beta-galactoside, quercetin-3-O-rutinose and kaempferol, exerted strong DPPH radical-scavenging activity. These results suggest that the Korean medicinal plants and the polyphenols isolated from them that exhibited effective radical-scavenging activity may be promising agents for scavenging free radicals and treating diseases associated with excess free radicals.

Biflavonoids↗
PubMed2003

Pharmacological profile of extracts of Pelargonium sidoides and their constituents.

In areas of southern Africa, aqueous extracts from the roots of Pelargonium sidoides are employed to cure various disorders. Nowadays, a modern formulation (EPs 7630), elaborated from the traditional herbal medicine, is successfully used for the treatment of respiratory tract diseases. We previously observed that root extracts of P. sidoides and their representative constituents exhibit moderate antibacterial and significant immunomodulatory capabilities. The present study was performed to further assess the efficacy and mode of action for these pharmacological activities. The results indicate that P. sidoides extracts may well possess antimycobacterial activity as claimed in traditional uses. Furthermore, significant antibacterial properties against multi-resistant Staphylococcus aureus strains as well as TNF-inducing potencies and prominent interferon-like activities in supernatants of sample-activated bone marrow-derived macrophages were observed using several functional assays. In addition, EPs 7630 stimulated the synthesis of IFN-beta in MG 63 cells as demonstrated by a specific enzyme immunoassay. For gallic acid, a characteristic constituent, evidence for the expression of iNOS and TNF-alpha transcripts in stimulated RAW 264.7 cells and, hence, activation at the transcriptional level was revealed by RT-PCR. The present results, when taken together with the recently reported pharmacological activities, provide for a rationale basis of the utilization of EPs 7630 in the treatment of respiratory tract infections.

Anti-Bacterial Agents↗
PubMed2004

Antioxidant properties of raw and processed cabbages.

To study the effect of polyphenolics on antioxidant activities of cabbages, the amounts of total phenolics, total flavonoids, antioxidant capacity and individual phenolic compounds in raw and processed cabbages were determined. Fresh and pickled red cabbages exhibited the highest total phenolic contents (393.1+/-10.8 mg and 366.3+/-3.6 mg gallic acid equivalents/100 g fresh sample, respectively). Fresh and pickled red cabbages were also highest in flavonoids (108.1+/-9.3 mg and 72.4+/-4.4 mg catechin equivalents/100 g fresh sample, respectively). The antioxidant capacity (expressed as vitamin C equivalent antioxidant capacity) ranged from 57.1 to 695.6 mg vitamin C equivalents/100 g fresh sample, where raw and pickled red cabbages exhibited the highest antioxidant capacity. There was a good linear relationship between the total phenolics and antioxidant capacity (r2=0.9743), and between the total flavonoids and antioxidant capacity (r2=0.9557); however, the relationship between the ascorbic acid content and antioxidant capacity was very low (r2=0.1442). The antioxidant capacity of raw and processed cabbages was highly correlated with their contents of polyphenolics. Kaempferol, quercetin, and apigenin were the major flavonoids existing in cabbages except for raw and pickled red cabbages, where cyanidin was the predominant flavonoid (73.6-117.7 mg/kg). In the red cabbages, cyanidin was the major contributor to the antioxidant capacity as well as the content of total phenolics and flavonoids.

Antioxidants↗
PubMed2005

Phenolic contents and antioxidant activity of some food and medicinal plants.

To identify promising sources of antioxidants, some food and medicinal plants were studied for total phenolic contents and antioxidant activity. The leaves, bark and fruits of Terminalia arjuna, Terminalia bellerica, Terminalia chebula and Terminalia muelleri, the leaves and fruits of Phyllanthus emblica, and the seeds of Syzygium cumini were found to have high total phenolic contents (72.0-167.2 mg/g) and high antioxidant activity (69.6-90.6%). Leaves of Eucalyptusglobulus were a rich source of rutin, Moringa oleifera for kaempferol, aerial parts of Centella asiatica for quercetin, fruits of T. bellerica and T. chebula for gallic acid, and bark of T. arjuna, leaves and fruits of T. bellerica and bark, leaves and fruits of T. muelleri for ellagic acid.

Antioxidants↗
PubMed2000

Hydrolyzable tannins and related polyphenols from Eucalyptus globulus.

Eucaglobulin (1), a new complex of gallotannin and monoterpene, was isolated from the leaves of Eucaloptus globulus. Its structure was elucidated on the basis of spectral data. Four known hydrolyzable tannins [tellimagrandin I (2), eucalbanin C (3), 2-O-digalloyl-1,3,4-tri-O-galloyl-beta-D-glucose (4), 6-O-digalloyl-1,2,3-tri-O-galloyl-beta-D-glucose (5)], as well as gallic acid (6) and (+)-catechin (7), were also isolated. The antibacterial effects of some of these compounds were examined.

Anti-Bacterial Agents↗
PubMed2002

Polyphenolic compounds from the leaves of Koelreuteria paniculata Laxm.

From the fresh leaves of Koelreuteria paniculata Laxm (Sapindaceae), four new compounds, named ethyl p-trigallate (1), 3''-O-galloyl-4'-O-galloyl-4-O-galloyl-gallic acid (2), ethyl p-heptagallate (3) and 3''-galloylquercitrin (4), together with 12 known compounds namely catechin (5), galloylepicatechin (6), isorhamnetin (7), kaempferol-3-O-arabinopyranoside (8), quercetin-3'-O-beta-D-arabinopyranoside (9), quercitrin (10), methyl p-digallate (11), methyl m-digallate (12), p-digalloyl acid (13), m-digalloyl acid (14), hyperin (15) and kaempferol-3-O-alpha-L-rhamnoside (16) were isolated by extensive column chromatographic separation. Their structures were elucidated on the basis of chemical and spectroscopic methods. Compound 9 was not reported previously with pyranoside of arabinose at C-3'. Compounds 4 and 9 possessed the activity for PTK inhibition.

Chromatography↗
PubMed2002

Phenolic glucosides from Alangium plantanifolium.

A novel phenolic glucoside alangitanifoliside A (1) together with two known phenolic glucosides 4',6'-O-(S)-hexahydroxydiphenylsalicin (2) and salicin (3), and gallic acid were isolated from stem barks of Alangium plantanifolium. Their structures were determined by spectroscopic and chemical methods. The structure of 1 was elucidated to be 1-O-[2-(1-hydroxy-6-oxocyclohex-2-ene-1-carboxymethyl)-phenyl]-4,6-O-[(S)-,4,4',5,5' 6,6'-hexahydroxydiphenoyl]-beta-D-glucopyranose.

Cornaceae↗
PubMed2006

A new tannin-related compound from the rhizome of Polygonum bistorta L.

A new tannin-related compound named bistortaside A (1) and a known compound have been isolated from the rhizome of Polygonum bistorta L. A new compound was elucidated as 3-methyl-gallic acid 4-O-beta-d-(6'-O-3''-methyl-galloyl)-glucopyranoside and a known compound was quercetin-3'-O-beta-d-glucopyranoside (2) on the basis of spectroscopic analysis.

Molecular Structure↗
PubMed2006

Isolation and identification of a novel flavonoid from Penthorum chinense P.

A novel flavonoid, pinocembrin-7-O-[3''-O-galloyl-4'',6''-hexahydroxydiphenoyl]-beta-glucose (1) was isolated from the whole plant of Penthorum chinense P., along with four known compounds, pinocembrin-7-O-beta-glucoside, quercitrin, quercetin-3-O-rhamnoside and gallic acid. The structures were established by spectroscopic analysis.

China↗
PubMed2006

Antioxidant galloylated flavonol glycosides from Calliandra haematocephala.

Three new acylated quercetin rhamnosides have been isolated from the leaves and stem of Calliandra haematocephala Hassk. (Fabaceae) and their structures were established as quercitrin 2''-O-caffeate (1), quercitrin 3''-O-gallate (2) and quercitrin 2'',3''-di-O-gallate (3). Also, 17 known compounds were identified as gallic acid (4), methyl gallate (5), caffeic acid (6), myricitrin (7), quercitrin (8), myricetin 3-O-beta-D-4C1-glucopyranoside (9), afzelin (10), isoquercitrin (11), myricetin 3-O-(6''-O-galloyl)-beta-D-glucopyranoside (12), myricitrin 2''-O-gallate (13), quercitrin 2''-O-gallate (14), afzelin 2''-O-gallate (15), myricitrin 3''-O-gallate (16), afzelin 3''-O-gallate (17), 1,2,3,4,6-penta-O-galloyl-beta-D-4C1-glucopyranose (18), myricitrin 2'',3''-di-O-gallate (19), quercetin 3-O-methyl ether (20), for the first time from the genus Calliandra except for 6. Compounds 7, 8, 13, 14, 16 and 19 exhibited moderate to strong radical scavenging properties on lipid peroxidation, hydroxyl radical, superoxide anion generation and DPPH radical in comparison with that of quercetin as a positive control in vitro. Compounds 7 and 8 exhibited lethal effect towards brine shrimp Artemia salina.

Animals↗