acteoside and aucubin

Herein, two iridoid glucosides aucubin (1) and ajugol (2), and two phenyl ethanoids, verbascoside (3) and poliumoside (4) were isolated from the methanol extract of the aerial parts of Verbascum speciosum and used to study about their anticancer activity for the first time. The structures of all compounds were elucidated using spectroscopic data (IR, 1D and 2D NMR, LC-TOF/MS). Antiproliferative activities of Aucubun (1) and Verbascoside (3) were tested against A-549 (human colon cancer), MDA-MD-453 (human breast cancer) and 3T3-L1 (mouse fibroblast)cell lines by XTT assay. In addition, the anticarcer mechanism of action of aucubin (1) was investigated on MDA-MB-453 cells for the first time. XTT result showed that both applied compounds exhibited antiproliferative effect at different dose ranges depending on the cancer type, as well as selectivity between cancer and healty cell lines. Flow cytometry analyzes revealed that aucubin (1) exerts its cytotoxic effect in MDA-MB-453 cells by directing cells to early apoptosis and inhibiting the P13K/AKT signaling pathway.

Topics: Animals; Glucosides; Humans; Mice; Plant Extracts; Verbascum

SA and H

Topics: Antioxidants; Hydrogen Peroxide; Iridoids; Orobanchaceae; Phenols; Salicylic Acid

The fruit pulp decoction of Crescentia cujete, commonly known as calabash, is traditionally used for the treatment of several respiratory diseases and is available as syrup formulations. Unfortunately, there is no detailed investigation on the analytical methods for warranting the quality of these products.. To develop and validate an appropriate analytical method for the simultaneous quantification of trans-cinnamic acid, 4-hydroxybenzoic acid, verbascoside and 6- epi-aucubin in the decoction and commercial cough syrups of Crescentia cujete fruit.. A reversed-phase ultra-high-performance liquid chromatographic method coupled to a diode array detector (UPLC-DAD) was validated following the ICH guidelines. The chromatographic analysis was performed using a C18 column, the mobile phase system consisted of water and acetonitrile containing 0.1% formic acid, and UV chromatograms were recorded from 200 to 400 nm.. A new UPLC-DAD method was validated for the simultaneous quantification of transcinnamic acid, 4-hydroxybenzoic acid, verbascoside and 6-epi-aucubin in calabash-derived products. After successful validation, this method was applied for the quantification of the selected chemical markers in an in-house decoction and three commercial cough syrups. Among the selected chemical markers, 6-epi-aucubin was the main compound in the calabash decoction, while trans-cinnamic acid and 4-hydroxybenzoic acid were the major compounds in the commercial products. Verbascoside and 6-epi-aucubin were below the limit of quantification in all syrup samples.. The proposed method was successfully applied for the analysis of three commercial syrup formulations and can be useful for standardization and quality control of raw and pharmaceutical calabash preparations.

Topics: Chromatography, High Pressure Liquid; Cough; Fruit; Glucosides; Iridoid Glucosides; Phenols

From two species of Sutera (S. foetida and S. cordata) (Scrophulariaceae tribe Limoselleae) were isolated three known secoiridoid glucosides (12-14) as well as four iridoid congeners (8-11), all biosynthetically derived from iridodial glucoside (and/or deoxyloganic acid). In addition, two previously unknown compounds were found, namely a terpenoid glucoside lactone (suterolide, 21) and the phenylethanoid glycoside 2''''-O-acetyl-angoroside A (19) as well as verbascoside, echinacoside and tubuloside A(15-17, respectively). Two other species, Jamesbrittenia dissecta and Lyperia antirrhinoides, previously considered to belong to the same genus (Sutera) were shown to be members of two different genera, respectively. Significantly, these two species contained iridoids derived from 8-epi-iridodial (and 8-epideoxyloganic acid), namely aucubin (2), melittoside (3) and acetylharpagide (4). In addition we investigated Melanospermum transvaalense, Lyperia tristis and Microdon dubius likewise from Limoselleae and all of these contained iridoid glucosides from the 8-epi-pathway. Thus, secoiridoid distribution confirms the DNA-based circumscription of Sutera and its sister-group relationship with Manulea. In addition, the results show that the clade including these two genera has a biosynthetic pathway to iridoids fundamentally different from the rest of the tribe and from the whole family Scrophulariaceae.

Topics: Glucosides; Glycosides; Iridoid Glucosides; Magnetic Resonance Spectroscopy; Molecular Structure; Phenols; Phylogeny; Pyrans; Scrophulariaceae; Spectrometry, Mass, Electrospray Ionization

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.

Topics: Glucosides; Glycosides; Iridoid Glucosides; Iridoids; Italy; Molecular Structure; Pedicularis; Phenols; Plant Extracts

In this study, we report the isolation and identification of several compounds present in the polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, collected in the protected area of Majella National Park. In particular, we have isolated and identified harpagide, 7-β-hydroxy-harpagide, ajugol, 5-allosyloxy-aucubin, verbascoside and, for the first time in this genus, arbutin.

Topics: Arbutin; Glucosides; Glycosides; Iridoid Glucosides; Iridoid Glycosides; Italy; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Phenols; Plant Components, Aerial; Plant Extracts; Pyrans; Stachys

In this study, we report the isolation and identification of several compounds from Plantago sempervirens Crantz, collected in the protected area of Majella National Park. We examined the polar fraction, in particular the iridoidic one. Aucubin, caryoptoside, plantarenaloside and gardoside were isolated and identified. For the first time, in this species, 8-epiloganic acid was recognised. Also, verbascoside, a phenylethanoid glycoside, was recognised in this plant.

Topics: Glucosides; Iridoid Glucosides; Iridoids; Italy; Magnetic Resonance Spectroscopy; Phenols; Plantago; Spectrometry, Mass, Electrospray Ionization

The monoterpenoid composition of Verbascum conocarpum and Scrophularia trifoliata, both endemic plants of Sardinia, was examined. The main chemotaxonomic markers of Scrophulariaceae, the iridoids aucubin, verbascoside and catalpol, were isolated.

Topics: Antineoplastic Agents, Phytogenic; Biomarkers; Classification; Glucosides; Humans; Iridoid Glucosides; Iridoids; Italy; Phenols; Phytotherapy; Plant Extracts; Quaternary Ammonium Compounds; Scrophularia; Verbascum

The aim of this study was to evaluate the in vitro antioxidant activity of the methanol extract of Plantago bellardii All. aerial parts. This was assessed by two different tests, scavenging of 1,1-diphenyl-2-picrylhydrazil (DPPH) radical, and inhibition of lipid peroxidation on liposomes prepared from bovine brain extract. In both tests the extract showed a potent antioxidant effect. The characterization of the major compounds in the extract as rutin, geniposide and verbascoside was performed by isolation and HPLC comparison with authentic samples. They were quantified by HPLC for the flavonoids and colorimetry for iridoids. The compounds that contribute most to the antioxidant activity were shown to be verbascoside and rutin.

Topics: Antioxidants; Glucosides; Iridoid Glucosides; Iridoids; Molecular Structure; Phenols; Plant Extracts; Plantago; Pyrans; Rutin

The plantain is used in herbal medicines and for pasturage. Two cultivars of plantain (Plantago lanceolata L.), Grasslands Lancelot and Ceres Tonic, were sown in spring. Changes in catalpol, aucubin, and acteoside concentrations in the leaves during the growing season and by drying after harvesting were quantitatively determined by high-performance liquid chromatography. The concentration of catalpol was relatively low, fluctuating between 1 and 2% of dry matter during the growing season, and there was no clear-cut seasonal change. From spring to midfall, the aucubin concentration increased from 2.1 to 4.8% in Grasslands Lancelot and from 1.0 to 2.7% in Ceres Tonic. These increases were gradual over the season, except for during midsummer, when aucubin concentrations were relatively constant. The acteoside concentration increased from 3.4 to 7.1% in Grasslands Lancelot and from 1.5 to 4.1% in Ceres Tonic over the course of the growing season, although in the summer it declined steadily to lows of 2.5% in Grasslands Lancelot and 1.9% in Ceres Tonic. Our data suggested that midfall was the appropriate time for harvesting plantain for medicinal use. The concentrations of the bioactive compounds steadily decreased in the initial stages of drying both under natural climatic conditions and at 60 degrees C. The development of processing methods to minimize the loss of bioactive compounds is imperative.

Topics: Chromatography, High Pressure Liquid; Climate; Desiccation; Glucosides; Iridoid Glucosides; Iridoids; Phenols; Plant Leaves; Plantago; Pyrans; Seasons