Iridoid Derivatives with Cytotoxic Activity from Pedicularis uliginosa Bunge.

Three new iridoids, rel-(4aR,7S,7aS)-7-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carbaldehyde (1), 1-methoxy-7-methyl-1,3,5,6-tetrahydrocyclopenta[c]pyran-4-carbaldehyde (2), and rel-(1R,4S,4aS,7R,7aR)-7-methylhexahydro-1,4-(epoxymethano)cyclopenta[c]pyran-3(1H)-one (3), together with seven known analogues, were isolated from the 95 % EtOH extract of the whole plants of Pedicularis uliginosa Bunge. Their structures were elucidated via extensive NMR spectroscopy and mass spectral data. In terms of inhibitory effects on human tumor cells, compounds 1, 2, 6, 7, and 8 exhibited better inhibitory activities against ACHN cells than the positive control (vinblastine).

Iridoids from Pedicularis verticillata and Their Anti-Complementary Activity.

Three new iridoids named as pediverticilatasin A - C (1 - 3, resp.), together with five known iridoids (4 - 8, resp.) were isolated from the whole plants of Pedicularis verticillata. The structures of three new compounds were identified as (1S,7R)-1-ethoxy-1,5,6,7-tetrahydro-7-hydroxy-7-methylcyclopenta[c]pyran-4(3H)-one (1), (1S,4aS,7R,7aS)-1-ethoxy-1,4a,5,6,7,7a-hexahydro-7-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid (2), (1S,4aS,7R,7aS)-1-ethoxy-1,4a,5,6,7,7a-hexahydro-7-hydroxy-7-methylcyclopenta[c]pyran-4-carbaldehyde (3). Their structures were elucidated on the basis of spectroscopic methods and compared with the NMR spectra data in the literature. All compounds were evaluated for their anti-complementary activity on the classical pathway of the complement system in vitro. Among which, compounds 1, 3, and 6 exhibited anti-complementary effects with CH50 values ranging from 0.43 to 1.72 mm, which are plausible candidates for developing potent anti-complementary agents.

[Determining of the content of determination of elements of Pedicularis from different places by ICP-MS after micriware-assisted digestion].

The content of elements in Pedicularis was determined by ICP-MS aftermicriware-assisted digestion. Recovery and RSD of the method is 95%-102% and 1.24%-2.18% respectively, and the method is rapid and precise. There is different Element content in Pedicularis from different places. There are some relations between altitude and content in different places. The result of Pedicularis can provide theoretical basis for medicine research.

[Flavonoids and nor-sesquiterpenes of Pedicularis densispica].

OBJECTIVE: To study the chemical constituents of the whole plants of Pedicularis densispica. METHOD: The chemical constituents were isolated by various chromatographic methods and their structures were determined by chemical evidences and spectral data. RESULT: Ten compounds were isolated and identified as acacetin (1), apigenin-7-0-beta-glucopyranoside (2), kaempferol-3,7-O-alpha-dirhamnopyranoside (3), scutellarein-7-0-beta-glucopyranoside (4), chrysoeriol-7-O-beta-glucopyranoside (5), pedicutricone A (6), dearabinosyl pneumonanthoside (7), salidroside (8), darendoside B (9), and maltol-beta-D-glucopyranoside (10). CONCLUSION: These compounds were isolated from the titled plant for the first time. Except compounds 6 and 8, the others were obtained for the first time from the genus Pedicularis.

A new monoterpene glycoside from Pedicularis verticillata and anticomplementary activity of its compounds.

A new monoterpene glycoside named as pedivertoside D (1), together with 13 known compounds (2-14, resp.) were isolated from the whole plant of Pedicularis verticillata L. The new compound was identified as (2E,6E,5R)-5,8-dihydrooxy-2,6-dimethyl-3,7-octadienyl-ß-D-glucopyranoside by spectroscopic methods including 2 D-NMR techniques. The known compounds were determined spectroscopically and compared with previously reported spectral data. Compounds 6 and 9 exhibited anticomplementary effects against the classical pathway (CP) with CH50 values of 0.07 mM and 0.23 mM, respectively, which are plausible candidates for developing potent anti-complementary agents from this plant.

Anti-sports anaemia effects of verbascoside and martynoside in mice.

This paper aims to investigate the effects of verbascoside and martynoside isolated from PEDICULARIS DOLICHOCYMBA on sports anaemia. Forty mice were divided into four groups: Group R (control group, nonsupplemented and maintained at rest), Group E (nonsupplemented and undergoing exercise), Group VE (supplemented with verbascoside 10 mg/kg per day and undergoing exercise), and Group ME (supplemented with martynoside 10 mg/kg per day and undergoing exercise). After 5 weeks intensive swimming exercises, we measured the RBC count, the hemoglobin concentration, the hematocrit (Hct), the mean corpuscular hemoglobin concentration (MCHC) and the mean corpuscular hemoglobin (MCH). We studied the shapes of RBC and measured the plasma malonyldialdehyde (MDA). We found Group E showed lower RBC, hemoglobin and Hct levels, higher MCHC, MCH, plasma MDA levels and the abnormally shaped RBCs percentage than Groups R, VE and ME. Group ME showed lower RBC and Hct levels, higher MCH, plasma MDA levels and the abnormally shaped RBCs percentage than Group VE. The results indicated that verbascoside and martynoside have the potential of antagonizing sports anaemia, the mechanism of this effect might be related to preventing RBC from free radical damage. Moreover, verbascoside was found to be more active than martynoside.

Antioxidant activity and potential ameliorating effective ingredients for high altitude-induced fatigue from Gansu Maxianhao (Pedicularis Kansuensis Maxim.).

OBJECTIVE: To investigate the antioxidant property and potential ameliorating effective ingredients for high altitude-induced fatigue from Gansu Maxianhao (Pedicularis Kansuensis Maxim.). METHODS: Macroporous adsorptive resin combined with polyamide chromatographic column was used to obtain water extract (P1), high polar part (P2), iridoid glycosides part (P3) and phenylethanoid glycosides part (P4) of Gansu Maxianhao (Pedicularis Kansuensis Maxim.). Antioxidant activity of each part was investigated employing a series of in vitro models. Hematoxylin-eosin staining, analysis of blood biochemical parameters, along with molecular analyses examining oxidative stress makers, metabolite, metabolic enzyme and energy substance in liver, skeletal muscle and/or serum were further measured. RESULTS: The results showed phenylethanoid glycosides (PhGs) exhibited more effective with 1,1-diphenyl-2-picrylhydrazyl radical scavenging ability, 2-2-Azinbis (3-ehtylbenzothiazolin-6-sulfnicAcid) Diammonium Salt+ scavenging activity, hydroxyl radical scavenging activity, reducing ability and antioxidant activity to varying extents. Under a hypobaric hypoxia attack in a hypobaric chamber (8000 m, 7 consecutive days), PhGs was administered to BALB/C mice at doses of 50, 200, 400 mg/kg and antifatigue property was evaluated using a swimming test at an altitude of 4000 m. The results showed that PhGs of Gansu Maxianhao (Pedicularis Kansuensis Maxim.) could significantly prolong the burden swimming time of mice, reduce the hypoxia-induced oxidative stress, remove the accumulated products of metabolism, improve the energy metabolism as well as improve preservation of endogenous glycogen stores. CONCLUSION: The ameliorating effect against altitude-induced fatigue of PhGs from Gansu Maxianhao (Pedicularis Kansuensis Maxim.) might come from the alleviation of oxidative stress, reduction of the adverse metabolic products, normalizing energy metabolism and increasing energy substances reserves. PhGs is a potential antioxidant and novel remedy for fatigue due to high-altitude hypoxia.

[Progress in research on Pedicularis plants].

Pedicularis comprises about 300 species in China and hemiparasite is its most important characteristic. Many compounds have been isolated from the genus, including phenylpropanoids, iridoids, flavonoids and so on. Among them, some showed antioxidative, antitumor, antifatigue, repairing DNA and antidiabetic activities. This review summarized hemiparasite, chemical constituents and pharmacological activities on Pedicularis plants. The aim was to provide information for the further study of Pedicularis.

A new iridoid and other chemical constituents from Pedicularis kansuensis forma albiflora Li.

A new iridoid (1) and thirteen known compounds 2-14 were isolated from Pedicularis kansuensis forma albiflora Li., and their structures were elucidated by spectroscopic methods including 2D-NMR techniques.

Beneficial health applications and medicinal values of Pedicularis plants: A review.

Pedicularis plants (Orobanchaceae), popularly known as lousewort, are found in Asia, Europe, and North America, and have been used in Sowa-Rigpa, the Himalayan art of healing and a traditional system of medicine for treating various ailments in humans. A comprehensive compilation on this valuable medicinal plant is not available, however. The present extensive review provides insight into the salient medicinal properties of Pedicularis plants with respect to various health issues and diseases. Our previous studies on Pedicularis plants from the Changthang region of Ladakh (India) and research advances leading to new developments in this field have prompted this review. The information presented here has been compiled and analyzed from authenticated published resources available on Medline, Pubmed, Pubmed Central, Science Direct, and other scientific databases. The Pedicularis genus consists of approximately 600 species (83 of which are found in India), with commonly reported species being Pedicularis longiflora Rudolph, P. bicornuta Klotzsch, P. oederi Vahl, P. cheilanthifolia, and P. pectinata. The major phytoconstituents of the Pedicularis sp. are phenols, phenylethanoids, phenylpropanoids, flavonoids, iridoids, lignans, and alkaloids, among others. The existing literature highlights that these compounds possess antioxidant, immunomodulatory, anti-inflammatory, antidiabetic, antibacterial, antifungal, analgesic, antitumor, hepatoprotective, neuroprotective, muscle-relaxing, antifatigue, diuretic, antipyretic, antithrombus, antihemolysis, and DNA-repairing properties. This medicinal herb is used in the treatment of leucorrhoea, fevers, sterility, rheumatism, general debility, collapse, and urinary problems, and for revitalizing the blood circulation, improving digestion, and maintaining vitality. This review emphasizes the various medicinal aspects of Pedicularis sp. plants containing a variety of phytoconstituents. Besides phenols, terpenoids, flavonoids, lignans, tannins, iridoid, and phenylpropanoid glycosides are among the active constituents responsible for multiple health effects. However, further extensive research is required to characterize the various phytoconstituents of Pedicularis to explore their modes of action at a molecular level and identify other beneficial applications that can exploit the tremendous medicinal potential of this important herb.

Secoiridoids and other chemotaxonomically relevant compounds in Pedicularis: phytochemical analysis and comparison of Pedicularis rostratocapitata Crantz and Pedicularis verticillata L. from Dolomites.

We compared the respective metabolite patterns of two Pedicularis species from Dolomites. Seven phenylethanoid glycosides, i.e., verbascoside (1), echinacoside (2), angoroside A (3), cistantubuloside B1 (4), wiedemannioside C (5), campneoside II (11) and cistantubuloside C1 (12), together with several iridoid glucosides as aucubin (6), euphroside (7), monomelittoside (8), mussaenosidic acid (9) and 8-epiloganic acid (13) were identified. Pedicularis verticillata showed also the presence of greatly unexpected secoiridoids, ligustroside (14) and excelside B (15), very rare compounds in Lamiales. Both PhGs and iridoids are considered of taxonomical relevance in the Asteridae and their occurrence in Pedicularis was discussed. In particular, the exclusive presence of several compounds such as 8-epiloganic acid (13), campneoside II (11), cistantubuloside C1 (12), ligustroside (14) and excelside B (15) in Pedicularis rostratocapitata, and angoroside A (3), cistantubuloside B1 (4) and wiedemannioside C (5) in P. verticillata could be considered specific markers for the two botanical entities.

Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in Dolomites, Italy.

In this study, we report the first phytochemical analysis of polar fraction of Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Several iridoid glucosides were isolated, namely aucubin (1), monomelittoside (2), plantarenaloside (3), euphroside (4), mussaenosidic acid (5) and 8-epiloganic acid (6), showing a composition in accordance with previous study on this genus. The studied samples, collected from Dolomites, presented a chemotype already recognised in species from North America, characterised by euphroside (4) and aucubin (1) as main components, but the main character was the presence of monomelittoside (2) never reported in this genus. The identification of verbascoside (7), leucosceptoside A (9) and echinacoside (10) complete the systematic framing of this species since is ascertained the co-occurrence of phenylethanoid glycosides with iridoids in Lamiales species.

Phenylethanoid glycosides of Pedicularis muscicola Maxim ameliorate high altitude-induced memory impairment.

Exposure to hypobaric hypoxia causes oxidative stress, neuronal degeneration and apoptosis that leads to memory impairment. Though oxidative stress contributes to neuronal degeneration and apoptosis in hypobaric hypoxia, the ability for phenylethanoid glycosides of Pedicularis muscicola Maxim (PhGs) to reverse high altitude memory impairment has not been studied. Rats were supplemented with PhGs orally for a week. After the fourth day of drug administration, rats were exposed to a 7500 m altitude simulation in a specially designed animal decompression chamber for 3 days. Spatial memory was assessed by the 8-arm radial maze test before and after exposure to hypobaric hypoxia. Histological assessment of neuronal degeneration was performed by hematoxylin-eosin (HE) staining. Changes in oxidative stress markers and changes in the expression of the apoptotic marker, caspase-3, were assessed in the hippocampus. Our results demonstrated that after exposure to hypobaric hypoxia, PhGs ameliorated high altitude memory impairment, as shown by the decreased values obtained for reference memory error (RME), working memory error (WME), and total error (TE). Meanwhile, administration of PhGs decreased hippocampal reactive oxygen species levels and consequent lipid peroxidation by elevating reduced glutathione levels and enhancing the free radical scavenging enzyme system. There was also a decrease in the number of pyknotic neurons and a reduction in caspase-3 expression in the hippocampus. These findings suggest that PhGs may be used therapeutically to ameliorate high altitude memory impairment.

Separation of Four Phenylpropanoid Glycosides from a Chinese Herb by HSCCC.

Four phenylpropanoid glycosides (PPGs), such as echinacoside, wiedemannioside C, forsythoside B and verbascoside, were isolated and purified from the Tibetan medicinal herb Pedicularis longiflora Rudolph. var. tubiformis (Klotz) Tsoong by high-speed counter-current chromatography (HSCCC) combined with macroporous resin (MR) column separation for the first time. In the present study, the two-phase solvent system composed of ethyl acetate-n-butanol-water (10 : 6:15, v/v/v) was used for HSCCC separation. A total of 3.5 mg of echinacoside, 12.6 mg of wiedemannioside C, 22.7 mg of forsythoside B and 48.7 mg of verbascoside with the purity of 93.6, 97.9, 97.8 and 98.1%, respectively, were obtained from 120 mg of crude sample. The HSCCC fractions were analyzed by HPLC, and the chemical structures were identified by (1)H NMR and (13)C NMR. The results demonstrate that MR coupled with HSCCC is a powerful technique for separation of PPGs from natural products.

Separation and determination of phenylpropanoid glycosides from Pedicularis species by capillary electrophoresis.

Capillary zone electrophoresis, using 30 mM borate buffer (pH 9.00) with 10% (v/v) methanol, was established for the identification and determination of four phenylpropanoid glycosides (PPGs)--echinocoside (ECH), verbascoside (VER), pedicularioside M (PED-M) and pedicularioside A (PED-A)--in extracts of Pedicularis longiflora var tubiformis, Pedicularis longiflora and Pedicularis Kansuensis. Regression equations revealed linear relationships (correlation coefficients: 0.9993-0.9999) between the peak area of each compound (ECH, VER, PED-M and PED-A) and its concentration. The relative standard deviations of the migration times and peak areas were <1.93 and 4.54%, respectively. The recoveries of four PPGs ranged between 95.6 and 108.4%. The effects of several CE parameters on the resolutions were studied systematically.

Docking study of cistanoside C to telomeric DNA fragment.

Experiments show that the natural products phenyl propanoid glycosides (PPGs) extracted from the plant Pedicularis spicata are capable of repairing DNA damaged by oxygen radicals. Based on kinetic measurements and experiments on tumor cells, a theoretical study of the interaction between PPG molecule Cistanoside C and telomeric DNA fragment has been carried out. The docking calculations performed using JUMNA software showed that the Cistanoside C could be docked into the minor groove of telomeric DNA and form complexes with the geometry suitable for an electron transfer between guanine radical and the ligand. Such complexes can be formed without major distortions of DNA structure and are further stabilized by the interaction with the saccharide side-groups.

Fast repair of the poly G hydroxyl radical adduct by two phenylpropanoid glycosides.

The repair activities and the reaction mechanisms of two phenylpropanoid glycosides (PPGs), isolated from a herb used in Chinese folk medicine, towards the oxidizing hydroxyl radical adduct of poly G were studied with a pulse radiolytic technique. On pulse irradiation of a nitrous oxide saturated 4 mM aqueous solution of poly G containing one of the tested compounds, the transient absorption spectrum of the hydroxyl radical adduct of poly G decays with the formation of that of the phenoxyl radical of the tested compound within several tens microseconds after the electron pulse irradiation. The results indicated that there was a repair reaction between the hydroxyl radical adduct of poly G and the compounds tested. The rate constants for the repair reactions of poly G hydroxyl radical adducts by verbasicoside and cistanoside C were determined to be 1.4 and 1.0 x 10(9) M(-1) x s(-1), respectively.

Iridoids from Pedicularis kansuensis forma albiflora.

A new iridoid glycoside kansuenoside (1) and a new iridoid kansuenin (2), along with eight known compounds (3-10) were isolated from the whole plant of Pedicularis kansuensis forma albiflora Li. Their structures were elucidated by spectroscopic methods. Nine of them were assayed against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus.

[Iridoid glycosides from Pedicula dicora Franch].

OBJECTIVE: To study the components in the root of Pedicula dicora. METHODS: Column chromatography with silica gel and polyamide was employed for the isolation and purification of ingredients. The structures were elucidated by spectral method. RESULT: Three iridoid glycosides were obtained and elucidated as mussaenoside, shanzhiside methyl ester and lamalbid. CONCLUSION: All the three compounds were separated from P. dicora for the first time.

[Effects of Pedicularis decora extract on anti-oxidation injury in mice].

OBJECTIVE: To study the protection effects of Pedicalaris decorm extract on oxidation lesion in mice and the effective components of Pedicalaris decorm. METHODS: The total extract, BuOH soluble components and water soluble components of Pedicalaris decorm were administered (ig) 15 g.kg-1.d-1 to mice, and the oxidation injury model in mice was induced by i.p. alloxan 180 mg.kg-1. SOD, GSH-Px and LPO in red blood cell and liver, ALT, AST, AKP and r-globulin in serum, LPO and MAO.B in brain, liver index and spleen index were measured. RESULTS: All the three Pedicalaris decorm extracts can obviously lower abnormal contents of SOD, GSH-Px, LPO, ALT, AST, AKP, MAO.B and r-globulin induced by alloxa, and obviously improve abnormal decrease of liver index and spleen index. CONCLUSION: Pedicalaris decorm extract can inhibit oxidation lesion in mice. The effects of total extract and BuOH soluble components were better than water soluble components.