Monoterpene Glucoside Research Articles

The effect of paeoniflorin against lipopolysaccharide-induced oxidative stress and lipid metabolism

Paeoniflorin (PF), a monoterpene glucoside, is one of the main bioactive components extracted from paeony root. Lipopolysaccharide (LPS) is a bacterial endotoxin capable of inducing extensive damage to organs, including the liver, because it stimulates increased production of free radicals and boosts lipid peroxidation. LPS induces the synthesis of several inflammatory cytokines and chemokines, as well as NO and inflammation in the liver of rats. The purpose of this study was to investigate the preventive effects of PF in lipid metabolism. PF of 2.5, 5, and 10 mg/kg concentration was intraperitoneally administered in rats at a dose of 1.5 mL/kg for 20 days. On day 21, 1.5 mL/kg of LPS was injected 4 hours prior to anesthetization. We examined lipid related functions by measurement of the levels of triglyceride (TG), total cholesterol (TC), total lipid (TL), and high-density lipoprotein cholesterol (HDL-C) in serum and malondialdehyde (MDA) in liver tissue. Results showed that LPS treatment increased the values of TG, TC, TL, and MDA, and decreased that of HDL-C. However, as a result of PF pretreatment, high values of TG, TC, TL, and MDA were decreased to low values and a low value of HDL-C was increased to a high value. These results suggested that PF might have potential for use as a natural supplement for improvement of lipid metabolism.

The unusual canangafruticosides A–E: Five monoterpene glucosides, two monoterpenes and a monoterpene glucoside diester of the aryldihydronaphthalene lignan dicarboxylic acid from leaves of Cananga odorata var. fruticosa

From the leaves of Cananga odorata var. fruticosa, five unusual monoterpene glucosides, named canangafruticosides A–E ( 1– 5), along with two unusual non-glucosidic monoterpenes ( 6, 7) were isolated. An aryldihydronaphthalene-type lignan dicarboxylate ( 8) was also isolated, with two moles of canangafruticoside A ( 1) on its ester moiety. This lignan also showed strong blue fluorescence emission under basic conditions. The structures of these compounds were elucidated by means of spectroscopic methods, with their absolute configurations determined by application of the modified Mosher’s method to a compound chemically derived from canangafruticoside E.

The effects of paeoniflorin on LPS-induced liver inflammatory reactions

Paeoniflorin (PF), a monoterpene glucoside, is a primary bioactive component of paeony, the root extract of Paeonia lactiflora. We tested the antioxidant effects of PF and its ability to prevent lipopolysaccharide (LPS)-induced oxidative stress. We intraperitoneally administered PF (2.5, 5, or 10 mg/kg) to rats for 20 days. On day 21, we injected the rats with LPS 4 h before sacrifice and measured serum levels of glutamate oxaloacetate transaminase, glutamate pyruvate transaminase, lactate dehydrogenase as well as the levels of malondialdehyde, superoxide dismutase, catalase, and glutathione peroxidase in liver whole-cell homogenates and mitochondrial fractions. LPS treatment increased levels of glutamate oxaloacetate transaminase, glutamate pyruvate transaminase, lactate dehydrogenase, and malondialdehyde, but PF treatment blocked these increases. LPS treatment also decreased antioxidant levels of superoxide dismutase, catalase, and glutathione peroxidase, but PF blocked these decreases. PF also protected liver tissue, as shown by histopathology. These results suggest that PF can protect against LPS-induced liver inflammation.

Improvement of the agitation granulation method to prepare granules containing a high content of a very hygroscopic drug

This study describes a new approach to the preparation of a granulate with a high content of a very hygroscopic powder or drug, using the agitation granulation method, and the development of a tablet formulation using these granulates. A Chinese medicine extract, Hatimi-zio-gan, was used as the model of a very hygroscopic drug. Among the several excipients tested, only porous calcium silicate could be used to prepare granules, with a mixing ratio (extract to porous calcium silicate) from 2:1 to 20:1. With other excipients, very large lumps were formed during the granulation process. The best mixing ratio of extract to porous calcium silicate was 6:1. For preparation of the granules, water could be added to the mixed powder within a range of 1- to 4-times the amount of porous calcium silicate. From these results, it was concluded that the ability of porous calcium silicate to hold large amounts of water in its numerous pores may allow for the preparation of granulates with a high content of very hygroscopic drugs. Starch with partial alpha-links, carboxymethyl starch sodium salt and crospovidone were used for selection of the disintegration agent. When crospovidone was used as a disintegration agent, tablets containing about 70% of the Chinese medicine extract disintegrated in less than 7 min, with good dissolution rates. The same process was applied to extracts of Hotyu-ekki-to, Syo-seiryu-to, Boi-ogi-to and Bohu-tusyo-san. The absorption of paeoniflorin, a characteristic monoterpene glucoside contained in Hatimi-zio-gan extract, was evaluated in beagle dogs after oral administration of the Hatimi-zio-gan tablets prepared in this study. The values of C(max) and AUC obtained after administration of the tablets prepared in this study were significantly greater than those obtained for commercial tablets.

Artemisioside, a new monoterpene glucoside from the aerial parts of Artemisia ordosica (Asteraceae)

A new monoterpene glucoside, artemisioside, was isolated from the aerial parts of Artemisia ordosica Krasch. (Asteraceae). The chemical structure was elucidated from physicochemical data and by the application of Klyne's rule.

Pharmacokinetic comparisons of typical constituents in white peony root and sulfur fumigated white peony root after oral administration to mice

Aim White peony root and sulfur fumigated white peony root are produced by different processing methods from the root of Paeonia lactiflora Pall, but the two traditional Chinese medicines are used under the same common name white peony root. In order to clarify the influence of sulfur fumigation on pharmacokinetics of the main monoterpene glucoside components in white peony root, an investigation was carried out to compare the pharmacokinetics of sodium paeoniflorin sulfonate ( 1) and paeoniflorin ( 2), benzoylpaeoniflorin sulfonate ( 3) and benzoylpaeoniflorin ( 4), as well as 1 in sulfur fumigated white peony root extract (SWPE) and 2 in white peony root extract (WPE). Materials and methods A high-performance liquid chromatographic (HPLC) assay was developed to determine the plasma concentrations of the four analytes. Kunming species of mice were orally administered the four compounds and the two extracts with approximately the same dose. Results It was found that C max and AUC of 1 and 3 were increased ( P < 0.05), and the T max and t 1/2 were prolonged ( P < 0.05) by comparison with that of 2. Similar results were also observed for the pharmacokinetics parameters of 1 in SWPE and 2 in WPE. However, benzoylpaeoniflorin ( 4) was not detected in plasma collected at certain intervals after administered orally to mice. Conclusions These results indicate that sulfonation of the monoterpene components could improve the bioavailability and delay the absorption of them in mice.

Three New Monoterpene Glucosides from Lamium amplexicaule

AbstractThree new monoterpene glucosides, lamiuamplexosides A–C (1–3), along with thirteen known glucosides, were isolated from the whole plant of Lamium amplexicaule L. The structures of 1–3 were elucidated on the basis of spectroscopic, chemical, and physicochemical evidence.

Two new monoterpenes from Sibiraea angustata

Two novel monoterpenes, sibiscolacton (1) and sibiraic acid (2), were isolated from the aerial part of Sibiraea angustata RCHD: . along with seven known compounds, namely three phenylpropanoids (3-5), two flavonoids (6,7), one glucityl ferulate (8, sibirate), and a monoterpene glucoside (9, sibiskoside). The structures of 1 and 2 were established on the basis of spectroscopic and chemical data.

Two new terpene glucosides and antitumor agents from Centipeda minima

One new monoterpene glucoside minimaoside A (1) and one new sesquiterpene glucoside minimaoside B (2), together with four known terpenoids, were isolated from the whole plants of Centipeda minima (L.) A. Braun et Ashers. Their structures were determined by spectroscopic methods. Compounds 5 and 6 showed weak or moderate cytotoxic activity toward several tumor cell lines.

Two new monoterpene glucosides from Paeonia lactiflora Pall.

Two new monoterpene glucosides, 4′-O-benzoylpaeoniflorin (1) and 4-O-galloylalbiflorin (2), were isolated from the 60% ethanol extract of the dried roots of Paeonia lactiflora Pall. Their structures were established on the basis of spectroscopic data.

Monoterpene Glucosides from Paeonia lactiflora

Four new "cage-like" monoterpene glucosides (1-4) were isolated from Paeonia lactiflora. The structures of these compounds were established by spectroscopic methods, mainly 1D and 2D NMR, and mass spectrometric analysis. Compound 4 exhibited moderate cell-protective activity against hydrogen peroxide-induced PC12 cell damage.

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides

Sixteen compounds were isolated from the MeOH extract of leaves of Myoporum bontioides. The five compounds hitherto unknown, were elucidated to be a chlorine-containing iridoid, named myopochlorin, and an iridoid glucoside, an acylated iridoid glucoside, a linear acetogenin glucoside, and an acyclic monoterpene glucoside, named myobontiosides A-D, respectively, by means of spectroscopic analyses.

Monoterpene glycosides from Paeonia hybrida

Monoterpene glycosides ( 1– 5, and 7), together with 14 known compounds, were isolated from the methanol extract of the roots of Paeonia hybrida. These compounds included a paeoniflorin-related glycoside with a hybrid structure of paeoniflorin and paeonovicinoside ( 1), a monoterpene glucoside biogenetically related to lactiflorin ( 2), a paeoniflorin-related monoterpene ( 3), arbiflorin-related monoterpenes ( 4 and 5), and a tymol-related monoterpene glycoside ( 7). Their structures were elucidated by extensive spectroscopic examinations.

A New Monoterpene Glucoside from the Roots of Paeonia lactiflora

AbstractA new monoterpene glucoside, 1‐O‐β‐D‐glucopyranosyl‐8‐O‐benzoylpaeonisuffrone (1), was isolated from the roots of Paeonia lactiflora cultivated in Korea, together with two known compounds 1‐O‐β‐D‐glucopyranosylpaeonisuffrone and paeonidanin (2). Their structures were established on the basis of chemical and spectroscopic methods.

Paeoniflorin induced immune tolerance of mesenteric lymph node lymphocytes via enhancing beta 2-adrenergic receptor desensitization in rats with adjuvant arthritis

Paeoniflorin (Pae), a monoterpene glucoside, is one of the main bioactive components of total glucosides of paeony (TGP) extracted from the root of Paeonia lactiflora. TGP has anti-inflammatory and immunoregulatory effects. In this study, we investigated the effects of Pae on inflammatory and immune responses to the mesenteric lymph node (MLN) lymphocytes and the mechanisms by which Pae regulates beta 2-adrenergic receptor (beta 2-AR) signal transduction in adjuvant arthritis (AA) rats. The onset of secondary arthritis in rats appeared around day 14 after injection of Freund's complete adjuvant (FCA). Remarkable secondary inflammatory response and lymphocytes proliferation were observed in AA rats, along with the decrease of anti-inflammatory cytokines interleukin (IL)-4 and transforming growth factor-beta 1 (TGF-beta 1) of MLN lymphocytes, and the increase of pro-inflammatory cytokine IL-2. The administration of Pae (50, 100 mg kg −1, days 17–24) significantly diminished the secondary hind paw swelling and arthritis scores, reversed the changes of cytokines as discussed above, and further decreased the lowered proliferation of MLN lymphocytes in AA rats. In vitro, Pae restored the previously increased level of cAMP of MLN lymphocytes at the concentrations of 12.5, 62.5 and 312.5 mg l −1. Meanwhile, Pae increased protein expressions of beta 2-AR and GRK2, and decreased that of beta-arrestin 1, 2 of MLN lymphocytes in AA rats. These results suggested that Pae might induce the Th1 cells immune tolerance, which then shift to Th2, Th3 cells mediated activities to take effect the anti-inflammatory and immunoregulatory effects. The mechanisms of Pae on beta 2-AR desensitization and beta 2-AR-AC-cAMP transmembrane signal transduction of MLN lymphocytes play crucial roles in pathogenesis of this disease.

Tricalysiosides P-U: Ent-kaurane Glucosides and a Labdane Glucoside from Leaves of Tricalysia dubia OHWI

Further extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of Tricalysia dubia afforded five new ent-kaurane glucosides (4-8) and one new labdane glucoside (9), together with a known megastigmane glucoside, sammangaoside B (1), and monoterpene glucosides (2, 3). The structures of the new compounds were elucidated by analyses of one- and two-dimensional NMR spectroscopic data. The absolute configuration of the 9-position of sammangaoside B was revised to S and its total stereochemistry was established by the modified Mosher's method.

Androstane and Monoterpene Glucoside Sinapoyl Ester from Cynanchum amplexicaule SIEB. et ZUCC.

A new androstane, 17beta-hydroxy-androsta-4,6,15-trien-3-one (1) and a new monoterpene glucoside sinapoyl ester, (3R)-8-hydroxylinalool 3,8-di-O-beta-D-(6'-O-E-sinapoyl)glucopyranoside (2) were isolated from the roots of Cynanchum amplexicaule SIEB. et ZUCC. (Asclepiadaceae), along with two known monoterpenes, (3R)-8-hydroxylinalool (3) and (6R)-menthiafolic acid (4). Their structures were elucidated on the basis of analyses of physical, chemical, and spectral data.

Polar Constituents from the Aerial Parts of Origanum vulgare L. Ssp. hirtum Growing Wild in Greece

From the polar extracts of Origanum vulgare L. ssp. hirtum 19 compounds have been isolated. The structures and relative stereochemistry have been elucidated by spectroscopic analysis and determined as apigenin, luteolin, chrysoeriol, diosmetin, quercetin, eriodictyol, cosmoside, vicenin-2, caffeic acid, p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside, thymoquinol 2-O-beta-glucopyranoside, thymoquinol 5-O-beta-glucopyranoside, thymoquinol 2,5-O-beta-diglucopyranoside, 12-hydroxyjasmonic acid, 12-hydroxyjasmonic acid 12-O-beta-glucopyranoside, lithospermic acid B, rosmarinic acid, 10-epi-lithospermic acid, and epi-lithospermic acid B. The three latter products display unusual stereochemistry of the 3,4-hydroxyphenyllactic acid unit(s), which to the authors' best knowledge has never been reported before in similar compounds. Moreover, lithospermic acid B (and its stereoisomers), p-menth-3-ene-1,2-diol 1-O-beta-glucopyranoside, 12-hydroxyjasmonic acid, and 12-hydroxyjasmonic acid 12-O-beta-glucopyranoside were isolated for the first time from Origanum species.

Camptothecins and Two New Monoterpene Glucosides from Ophiorrhiza liukiuensis.

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A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa.

AbstractFor Abstract see ChemInform Abstract in Full Text.