Glycosides Acteoside Research Articles

Comparative Study of Plantago media Extracts in the Treatment of Acanthamoeba sp. Trophozoites

(1) Background: The aim of the study was to compare the potency of Plantago media L. (Plantaginaceae) extracts on Acanthamoeba sp. trophozoites, which are opportunistic protozoan parasites leading to several dangerous diseases; (2) Methods: The chromatographically (TLC, HPLC-DAD) characterized water fractions of the extracts from biomass from in vitro cultures (shoots and roots), leaves, and inflorescences from field cultivation were used for the study of the acanthamoebic activity in a Thoma haemocytometer chamber; (3) Results: The anti-amoebic effect at the lowest concentration (1.0 mg/mL) was demonstrated only by the extract of the leaves from the cultivation (50.50% inhibition). The remaining samples inhibited the growth of parasites from a concentration of 5.0 mg/mL in the range of 41.36% inflorescences to 63.89% shoots in vitro. Quantitative determinations of phenolic compounds in the tested extracts indicate a tendency to increase the potency of the anti-amoebic effect with the content of a phenylethanoid glycoside—acteoside. The maximum content of this compound was determined in leaves from field cultivation (6.64%) and the minimum in inflorescences (0.65%). This is confirmed by the range of the lowest IC50 values (the strongest biological activity) for the tested samples, 0.95–1.80 mg/mL for leaves from cultivation, and the high values, 9.70–5.30 mg/mL for inflorescences and in-vitro-derived roots. The strength of the biological activity of the extracts correlated with the content of acteoside, which constituted 84–93% of the sum of phenolic compounds determined; (4) Conclusions: The performed investigations proved the anti-acanthamoebic efficacy of Plantago media organs, including those obtainable by biotechnological methods, and indicated phenylethanoid glycosides, their main phenolic constituents, to be responsible for the activity. To our knowledge, this is the first report on the amoebicidal activity of Plantago media extracts from biomass produced by biotechnological methods and organs of an intact plant.

Anti-infammatory and antioxidant activities of acteoside isolated from Acanthus ilicifolius var. xiamenensis

Acanthus ilicifolius var. xiamenensis (Acanthaceae), a mangrove found in southeastern China, is an herb with strong antiinflammatory property. Phytochemical study of the mangrove showed that the plant has a high content of phenylethanol glycoside acteoside (AC). In this research, the anti-inflammatory activity of acteoside on dextran sodium sulphate (DSS)-mediated mouse ulcerative colitis model were studied. For DSS- mediated colitis in mice, AC can reduce weight loss and DAI score in UC mice, suppress colon shortening and alleviate colon pathological injury. Moreover, AC treatment notably up-regulates IL-10, down-regulates the levels of IL-1β and TNF-α, and inhibits the protein expression of JAK2/STAT3, NF-κB p65, IKKα/β and IKB of colon. In addition, after AC treatment, the level of MDA and NO in colonic tissue were remarkably decreased, while the levels of GSH, SOD, and Nrf2 and HO-1 protein expression levels were significantly increased. These results indicate that AC can activate the Nrf2 signaling pathway by inhibiting the JAK/STAT, iNOS/eNOS and NF-κB signaling cascades, enhance the intestinal barrier function, and effectively reduce DSS-induced UC in mice.

Enzyme inhibitory assessment of the isolated constituents from Plantago holosteum Scop.

Plants of the Plantago genus are widely used in Turkish folk medicine especially for the treatment of wound, abscess, and inflammation. The aqueous extract and five phenylethanoid glycosides acteoside (1), arenarioside (2), echinacoside (3), isoacteoside (4), and leucosceptoside A (5) isolated from the aerial parts and roots of Plantago holosteum Scop. (Plantaginaceae) were tested for their possible inhibitory activity against hyaluronidase, elastase, and collagenase, related to wound pathogenesis. Even though the aqueous extract prepared from the aerial parts (36.26%) and roots (47.01%) and the isolated compounds acteoside (29.13%), echinacoside (28.73%), and isoacteoside (31.69%) exerted a notable inhibition, arenarioside and leucosceptoside A were found inactive in the hyaluronidase enzyme inhibition test. Similar results were obtained from the collagenase enzyme inhibition test. The aqueous extract prepared from the aerial parts (31.09%) and roots (35.17%), echinacoside (25.13%), and isoacteoside (23.85%) exerted a notable inhibition in this test. However, none of the extracts and isolated compounds displayed elastase enzyme inhibitory activity. The experimental data demonstrated that P. holosteum displayed a remarkable enzyme inhibitory activity against hyaluronidase and collagenase. This paper is the first report regarding the in vitro enzyme inhibitory activity of P. holosteum.

Anti-Respiratory Syncytial Virus Activity of Plantago asiatica and Clerodendrum trichotomum Extracts In Vitro and In Vivo.

The herbs Plantago asiatica and Clerodendrum trichotomum have been commonly used for centuries in indigenous and folk medicine in tropical and subtropical regions of the world. In this study, we show that extracts from these herbs have antiviral effects against the respiratory syncytial virus (RSV) in vitro cell cultures and an in vivo mouse model. Treatment of HEp2 cells and A549 cells with a non-cytotoxic concentration of Plantago asiatica or Clerodendrum trichotomum extract significantly reduced RSV replication, RSV-induced cell death, RSV gene transcription, RSV protein synthesis, and also blocked syncytia formation. Interestingly, oral inoculation with each herb extract significantly improved viral clearance in the lungs of BALB/c mice. Based on reported information and a high-performance liquid chromatography (HPLC) analysis, the phenolic glycoside acteoside was identified as an active chemical component of both herb extracts. An effective dose of acteoside exhibited similar antiviral effects as each herb extract against RSV in vitro and in vivo. Collectively, these results suggest that extracts of Plantago asiatica and Clerodendrum trichotomum could provide a potent natural source of an antiviral drug candidate against RSV infection.

GLYCOSIDES ISOLATED FROM THE AERIAL PARTS OF Premna integrifolia L. GROWING IN THAI BINH

From the aerial parts of Premna integrifolia L., three glycosides acteoside (1), premnaodoroside A (2), and premnaodoroside B (3) were isolated. Their chemical structures were elucidated by means of ESI-MS, 1H-NMR, 13C-NMR, HSQC, HMBC spectra and in comparison with the previous literature. To our best knowledge, this is the first report of 1 and 3 from P. integrifolia.

Alpha-pyrone glycosides fromScutellaria salviifoliaBenth

Scutellaria salviifolia Benth. is an endemic species growing in Turkey that belongs to the family Lamiaceae. As a result of a phytochemical study on the aerial parts of S. salviifolia Benth., two new and 10 known compounds were isolated from the aqueous fraction of methanolic extract. The new compounds are methyl-$\alpha $-pyrone glucosides, 3,4-dihydroxy-6-methylpyran-2-one 3-$O$-$\beta $-glucopyranoside (=scusalvioside A, 1), and 3,4-dihydroxy-6-methylpyran-2-one 3-$O$-$\beta $-(6$'$-$O$-$E$-caffeoyl) glucopyranoside (=scusalvioside B, 2) with new skeletal structures. Along with them, 3 phloroglucinol glucosides [phlorin (3), tadehaginoside (4), and 6$^{\prime \prime} $-$O$-$Z$-$p$-coumaroyl phloroglucinol-1-$O$-$\beta $-glucopyranoside (5)], 6 flavonoids [apigenin (6), apigenin 5-$O$-$\beta $-glucopyranoside (7), isoschaftoside (8), luteolin 7-$O$-$\beta $-glucuronide (9), luteolin 4$'$-$O$-$\beta $-glucopyranoside (10), and hispidulin (11)], and one phenylethanoid glycoside [martynoside (12)] were also isolated as known compounds. Compounds 2 and 8 were isolated as a mixture. Structure elucidations of the isolated compounds were carried out using UV, $^{1}$H NMR, $^{13}$C NMR, 2D NMR, and HR-ESI-MS analyses. Moreover, the phenylethanoid glycosides acteoside (13) and leucosceptoside A (14) were also detected in the plant by HPLC-DAD study. Tadehaginoside, 6$^{\prime \prime} $-$O$-$Z$-$p$-coumaroyl phloroglucinol-1-$O$-$\beta $-glucopyranoside, and luteolin 4$'$-$O$-$\beta $-glucopyranoside were reported for the first time from a Scutellaria species with this study.

Determination of phenylethanoid glycosides and iridoid glycosides from therapeutically used Plantago species by CE‐MEKC

CE methods are valuable tools for medicinal plant quality management, screening, and analysis. Therefore, the aim of the current study was to optimize and validate a CE-MEKC method for simultaneous quantification of four chief bioactive metabolites from Plantago species. The two most important secondary metabolite groups were aimed to be separated. Different electrolyte and surfactant types were tested. Surfactant concentration, BGE pH, electrolyte concentration, and buffering capacity were optimized. The final BGE consisted of 15 mM sodium tetraborate, 20 mM TAPS, and 250 mM DOC at pH 8.50. Acceptable precision, good stability, and accuracy were achieved, with high resolution for phenylethanoid glycosides. Analytes were separated within 20 min. The method was shown to be suitable for the quantification of the iridoid glycosides aucubin and catalpol, and the phenylethanoid glycosides acteoside (verbascoside) and plantamajoside from water extracts of different samples. The method was shown to be applicable to leaf extracts of Plantago lanceolata, Plantago major, and Plantago asiatica, the main species with therapeutic applications, and a biotechnological product, plant tissue cultures (calli) of P. lanceolata. Baseline separation of the main constituents from minor peaks was achieved, regardless of the matrix type.

Comparative study of some polyphenols in Plantago species

Abstract The identification and determination of major flavonoids in endemic species Plantago schwarzenbergiana and Plantago reniformis is reported for the first time. Flavonoids and phenylpropanoid glycoside acteoside were also determined in four other Plantago species, namely Plantago atrata, Plantago coronopus, Plantago holosteum and Plantago lanceolata, using LC–MS/MS and HPTLC analysis, respectively. Apigenin was found to be the major flavonoid in P. schwarzenbergiana, while luteolin and luteolin-7-O-glucoside were dominant compounds in P. atrata, P. coronopus, P. holosteum and P. lanceolata. Luteolin and apigenin were present in P. reniformis in lowest amounts, and corresponding glucosides were detected in traces only. The acteoside concentration was the highest in P. lanceolata (21.71 mg/g dry weight). The extracts were also evaluated regarding the contents of total phenolics, phenylpropanoid glycosides (PPGs), and iridoids. P. lanceolata contained the highest concentrations of total phenolics and PPGs, while P. holosteum was the richest in iridoids. Moreover, xanthone-C-glucoside mangiferin was not reported in Plantago species before.

CHANGES IN THE LEVEL OF BIOACTIVE COMPOUNDS IN PAULOWNIA TOMENTOSA FRUITS

The flavonoid and phenylpropanoid glycoside contents of Paulownia tomentosa Steud. fruits have been investigated in EtOH extracts obtained during the growing season. Using an HPLC-DAD system, we identified and quantified six C-geranyl flavanones: 3′-O-methyl-5′-hydroxydiplacone (1), 3′-O-methyl-5′-O-methyldiplacone (2), 3′-O-methyldiplacol (3), 3′-O-methyldiplacone (4), mimulone (5) and diplacone (6), and two phenylpropanoid glycosides acteoside (7) and isoacteoside (8). The levels of the flavonoids varied from minimums of 0.002–0.027% to maximums of 0.064–0.313% depending upon the individual flavonoid. The concentrations of the flavonoids increased during the 6-month period of the experiment in contrast to a decrease in the concentrations of the phenylpropanoid glycosides. The concentration of 8 was relatively low, fluctuating between 0.003 and 0.189%, whereas the concentration of 7 was the highest of all of the compounds investigated at 1.4%. The quantity of phenylpropanoid glycosides declined until June and then scarcely changed. Our data suggested that early summer was the appropriate time for harvesting P. tomentosa fruits if one is interested in the phenylpropanoid glycosides and autumn the best for the flavonoids. Our findings can be useful for obtaining the highest concentration of bioactive compounds of P. tomentosa fruits that can ensure a more effective study of the medicinal properties of these compounds and eventually a preparation of more efficient synthetic derivates. We have also examined the influence of the climatological condition on the total content of phenolic compounds.

Bioguided isolation of angiotensin‐converting enzyme inhibitors from the seeds of Plantago asiatica L.

Ethanolic extract of the seeds of Plantago asiatica L. showed significant inhibitory activity of angiotensin-converting enzyme (ACE) determined by monitoring the transformation from a substrate hippuryl-histidyl-leucine (HHL) to the product hippuric acid (HA) in vitro using an UPLC-MS method. The bioguided fractionation of the extract resulted in the isolation of four ACE inhibitory active phenylpropanoid glycosides acteoside, isoacteoside, plantainoside D, and plantamajoside with IC(50) values of 2.69 mM, 2.46 mM, 2.17 mM, and 2.47 mM, respectively. Their structures were elucidated through the analysis of NMR, UV, IR and MS data. Our study is the first demonstration that Plantago asiatica L. and its major constituents have ACE inhibitory activity in vitro. It is assumed that the identified compounds contribute to the angiotensin-converting enzyme-inhibitory activity of the extract.

Hypouricemic Effects of Phenylpropanoid Glycosides Acteoside ofScrophularia ningpoensison Serum Uric Acid Levels in Potassium Oxonate-Pretreated Mice

Phenylpropanoid glycoside acteoside was extracted from the traditional Chinese medicine Scrophularia ningpoenis Hemsl. In the present study, we investigated the effects of acteoside administration on serum uric acid levels in mice rendered hyperuricemic with the uricase inhibitor potassium oxonate. When administered orally for 3 days at doses of 50, 100 and 150 mg/kg, acteoside reduced serum uric acid levels by 15.2, 23.8 and 33.1%, respectively, relative to vehicle-treated hyperuricemic mice. Importantly, in non-hyperuricemic mice, the serum uric acid levels were not affected by acetoside treatment. Acteoside also inhibited mouse liver xanthine dehydrogenase XDH and xanthine oxidase XO activity at all three doses. These results suggest that the hypouricemic action of acteoside may be attributable to its inhibition of XDH/XO activity.

Ipolamiide and fulvoipolamiide from Stachytarpheta glabra (Verbenaceae): A structural and spectroscopic characterization

The phenylethanoid glycoside acteoside and the iridoids ipolamiide and 4-methoxycarbonyl-7-methylcyclopenta[ c]pyran (fulvoipolamiide) were isolated from the leaves of Stachytarpheta glabra. The solid state structure of fulvoipolamiide was confirmed by X-ray diffraction studies. The molecules of fulvoipolamiide are displayed in layers parallel to the crystallographic axis a . This molecule is planar with electron delocalization in the fused ring system and the pyran rings of adjacent layers in the solid state structure are involved in a π–π stacking interaction. Raman spectroscopy has also been used to characterize the most important bands present in the spectra of fulvoipolamiide and ipolamiide, and comparison made with literature allows the assignment of some key markers, specially the bands in the 1600–1700 cm −1 range.

Carnivorous plant chemistry

Phytochemical data are contrasted with phylogenetic relationships of carnivorous plants. Naphthoquinone profiles of a representative set of Nepenthes species are evaluated in comparison with previously published chemical data for Nepenthales (containing four distinct carnivorous plant families). The iridoids sarracenin and aucubin are identified as valuable chemical markers of Sarraceniaceae and Scrophulariales, respectively. The latter order (that contains the carnivorous Lentibulariaceae and Byblidaceae) is also characterized by the common occurrence of the phenylethanoid caffeic acid glycoside acteoside. No taxonomically relevant metabolite is known from Cephalotaceae so far.

Phytochemical investigation and antioxidant activity ofDuranta repens

The ethylacetate fraction of the methanol extract of Duranta repens L. (Verbenaceae) showed radicalscavenging activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Three compounds were isolated from this fraction, i.e. the phenylethanoid glycoside acteoside, the iridoid lamiide and the saponin pseudo-ginsenoside-RT1. Acteoside showed an IC50 of 3.05 +/- 0.09 microg/mL in the DPPH assay, while lamiide and pseudo-ginsenoside-RT1 were not active.

Iridoid and phenylethanoid glycosides from Phlomis tuberosa L.

A new iridoid glucoside, 8-O-acetylshanzhiside (1), was isolated from the aerial parts of Phlomis tuberosa, together with two known iridoid glucosides, shanzhiside methyl ester and lamalbide. The known phenylethanoid glycosides acteoside and forsythoside B were also obtained and characterized. The structure of 1 was determined by means of 1D- and 2D-NMR spectroscopic evidence.

Iridoid and megastigmane glycosides from Phlomis aurea

From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin ( 1 ) and phlomurin ( 2 ), a new megastigmane glucoside phlomuroside ( 3 ) and a new benzyl alcohol glycoside having the structure benzyl alcohol- O-β-xylopyranosyl-(1→2)-β-glucopyranoside ( 4 ) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl- O-β-xylopyranosyl-(1→2)-β-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7- O-β-glucopyranoside, acacetin-7- O-β-glucopyranoside and luteolin-7- O-β-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.

Antiinflammatory and antinociceptive activities of extracts and isolated compounds from Stachytarpheta cayennensis

The alcoholic and n-butanolic extracts of dried leaves of Stachytarpheta cayennensis (L.C. Rich) Vahl (Verbenaceae) was assessed in antiinflammatory and antinociceptive models. Intraperitoneal pretreatment with the dried extracts at doses ranging from 100 to 200 mg/kg, significantly inhibited carrageenin inducing edema formation. The active extracts were then fractionated and monitored with the same bioassay. The iridoid ipolamiide and the phenylethanoid glycoside acteoside were isolated from the active fraction and showed inhibitory effect on histamine and bradykinin induced contractions of guinea-pig ileum. The compounds also showed in vivo antiinflammatory activity when administered orally to rats mainly in the fourth hour after the administration of the phlogistic agent (70.22% and 93.99%, respectively). These results indicate that S. cayennensis shows antiinflammatory properties which seems to be due, at least partly, to the inhibition of bradyknin and histamine. The extracts also exhibited antinociceptive activity measured by the hot-plate test both i.p. and p.o. in doses ranging from 100 to 300 mg/kg

Induction of cytokines by a phenylpropanoid glycoside acteoside.

A phenylpropanoid glycoside acteoside was found to induce interleukin (IL)-1, IL-6, and tumor necrosis factor-alpha (TNF-alpha) in macrophage-like cell line J774.A1 at 1-100 ng/ml. In addition, when the stimulatory action of acteoside was studied using the bovine glomerular endothelial cell line GEN-T, it stimulated IL-6 production. These stimulatory activities were not abolished by treatment with polymixin B, which inactivates lipopolysaccharide (LPS), indicating that the action was not a contamination of LPS.

The distribution of acteoside among angiosperms

The distribution of the phenylpropanoid glycoside acteoside is restricted to a constellation of families which may constitute a natural ordinal grouping. This distribution of acteoside contains many families traditionally clustered in a Scrophulariales-Lamiales complex. It includes Retziaceae, Oleaceae, Stilbaceae, and Hippuridaceae, but excludes Hydrostachyaceae.

Distribution and taxonomic implications of some phenolics in the family gesneriaceae determined by EPR spectroscopy

The dihydric phenolics from the leaves of 590 specimens of 91 genera of Gesneriaceae have been examined as semiquinone radicals by EPR spectroscopy. The glycosides acteoside and/or conandroside were found widespread in the family, but were not observed in the tribes Klugieae and Napeantheae and in the genera Agalmyla and Saintpaulia. The absence of the glycosides in several specimens seemed compensated for by the presence of either protocatechuic acid or an ester of homogentisic acid. Actually, the ester was found to be ubiquitous in Agalmyla, but absent in the related Aeschynanthus. A dihydrocaffeic acid ester was found restricted to the European gesneriads, distinguishing them from similar Asian genera. Chlorogenic acid was not observed in the family, at variance with older reports. Hydroquinone was recorded from three specimens.