Two new secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora

From the roots ofPicrorhiza scrophulariiflora, two new secoifidoid glycosides, named picrosecosides Ⅰ and Ⅱ （1, 2） have been isolated. Their structures were elucidated on the basis of chemical and spectropic evidences.

Minor secoiridoid aglycones from the low-polarity part of the traditional Chinese herb: Swertia mileensis

Eleven new secoiridoid aglycones involving unusual C9-skeleton:swerimilegenins A-F(1-6);bis-C9-skeleton:swerimilegenin G(7);and C_(10)-skeleton:swerimilegenins H−K(8−11),as well as six known ones,were isolated from the low-polarity part of the traditional Chinese herb medicine Swertia mileensis.Their structures were determined by extensive spectroscopic data and X-ray diffraction.Biogenetically,swerimilegenin A(1)belonged to 10-nor-secoiridoid,and swerimilegenins B-F(2-6)were 1-nor-secoiridoids.Erythrocentaurin(12)and gentiogenal(15)showed moderate anti-HBV activity on HepG 2.2.15 cell line in vitro.

A Fragmentation Study on Four Unusual Secoiridoid Trimers,Swerilactones H–K,by Electrospray Tandem Mass Spectrometry

Swerilactones H–K(1–4)as four unprecedented secoiridoid trimers represent a new type of natural product,which has attracted much interest of natural chemists due to their novel skeletons and promising bioactivity.In order to well understand their MS fragmentation behaviors,they were investigated by electrospray ionization ion-trap time-of-flight multistage product ion mass spectrometry(ESI-IT-TOF-MSn)for the first time.The protonated molecules([M?H]?)of swerilactones J and K,and deprotonated molecules([M-H]-)of swerilactones H,J and K were readily observed in the conventional single-stage mass spectra(MS);however only the[M?Cl]-ion for swerilactone I was obtained in negative mode.Based on the MSn study,the fragmentation pathways of swerilactones H and I in negative mode,and swerilactones J and K in both positive and negative modes were proposed.The neutral losses of H_(2)O,CO,CO_(2)and C_(2)H_(4)O moieties are the particular elimination from the precursor ions due to the presence of hydroxyl,d-lactone and 1-O-ethyl moieties in their structures,of which the retro-Diels–Alder cleavage was the most particular dissociation.The fragment ions at m/z 341 and 291 in negative mode can be considered as the diagnostic ions for secoiridoid trimers.This investigation will provide valuable information for their fast characterization from complicated natural mixtures and extensive understanding their structural architectures.

Five new sucrose esters from the whole plants of Phyllanthus cochinchinensis

Chemical investigation of the whole plants of Phyllanthus cochinchinensis(Euphorbiaceae)led to the isolation of five new sucrose benzoyl esters,3,6'-di-O-benzoylsucrose(1),3,6'-di-O-benzoyl-2'-O-acetylsucrose(2),3,6'-di-O-benzoyl-4'-O-acetylsucrose(3),3,6'-di-O-benzoyl-3'-O-acetylsucrose(4)and 3-O-benzoyl-6'-O-(E)-cinnamoylsucrose(5),together with two known secoiridoid glycosides,jasminoside(6)and jaslanceoside B(7).Their structures were established on the basis of detailed spectroscopic analysis and chemical method.

The Distribution,Uses,and Characteristic Components of Gentianaceae Plants in China

Extracts of Gentianaceae herbs have been widely used as food additives,teas,or medicinal remedies for various human diseases and disorders.Iridoids,secoiridoids,and analogs glycosides,mainly include gentiopicroside,sweroside,swertiamarin,and loganic acid,are the characteristic compounds found in the Gentianaceae plants.The uses of the medicinal herbs containing these secoiridoids have been described in Chinese Materia Medica.Herbal extracts containing iridoids,secoiridoids,and analogs could exert protective effects in multiple human tissues and cells.Some of these medicinal herbs have been studied using modern pharmacological means.The results indicate that they have analgesic,liver protective,anti-inflammatory,antiallergic,anti-pathogeny,and anti-bacterial functions.This review was aimed to summarize the use of Gentianaceae herbs for disease treatments and pharmacokinetic characteristics of the active compounds.In so doing,we hope to demonstrate that Gentianaceae herbs and bioactive compounds in them may have abilities to affect inflammation,hepatic metabolism and cell signaling.In addition,we would like to bring this to the attention of the field about the use and study of compounds derived from Gentianaceae herbs.

HPLC Fingerprint and LC-TOF-MS Analysis on Extract from Roots of Gentiana macrophylla

Objective Establishing a fingerprint method to identify the characteristic chemicals in the roots of Gentiana macrophylla and evaluate their quality. Methods RP-HPLC was developed for fingerprint analysis and determination of four ingredients in G. macrophylla roots from different sources. LC-ESI-TOF-MS was employed to identify the chromatographic peaks of the fingerprint. Results Five common peaks were identified by comparing their retention time with reference secoiridoid glucosides. Eight major peaks in chromatographic fingerprint were analyzed by on-line LC-ESI-TOF-MS. Four secoiridoid glucosides were identified based on their MS data. Conclusion The method is specific and could be served for the quality identification and comprehensive evaluation of G. macrophylla.

A New Secoiridoid Glycoside from Roots of Picrorhiza scrophulariiflora

Objective To study the chemical constituents in the roots of Picrorhiza scrophulariiflora.Methods The chemical constituents in the roots of P.scrophulariiflora were separated and purified with chromatographic methods.The structures were elucidated by spectroscopic methods and chemical analyses.Results A new secoiridoid glycoside,picrogentioside II(1) was successfully isolated from the roots of P.scrophulariiflora.Conclusion Compound 1 is a new secoiridoid glycoside.

Three new secoiridoid glycosides from the flower buds of Lonicera japonica

Three new secoiridoid glycosides,named lonijapoglycol A(1),aldosecolohanin C(2)and aldosecolohanin B(3),together with three known ones(4–6),have been isolated from the flower the buds of Lonicera japonica.All the structures were identified by spectroscopic analyses.Lonijapoglycol A(1)expressed significant anti-inflammatory activity to inhibit the release ofβ-glucuronidase induced by platelet-activating factor in rat polymorphonuclear leukocytes with an IC50 value of 3.76μmol·L^-1.

A New Secoiridoid Glycoside from Swertia cincta

Objective To study the chemical constituents of Swertia cincta. Methods Preparative liquid chromatography was employed. The structures of the compounds were elucidated by spectroscopic analysis. isolated from S. cincta and identified as Results Three secoiridoid glycosides were 8-methoxyl-eustomorusside （1）, secoiridoids eustomorusside （2）, and eustomoside （3）. Conclusion Compound 1 is a new secoiridoid glycoside. Compounds 2 and 3 are isolated from this plant for the first time.

Pharmacokinetic and Relative Bioavailability of Three Secoiridoid Glycosides in Beagle Dog Plasma After Oral Administration of Conventional and Enteric-Coated Capsules of Gentianella acuta Extract

Objective:To simultaneously investigate the pharmacokinetics of gentiopicroside,sweroside,and swertiamarin,which are constituents of Gentianella acuta,by developing and validating a simple,sensitive,and fast ultra-high-performance liquid chromatography–tandem mass spectrometry method.Materials and Methods:Blood samples were collected from the forward limb veins of six beagle dogs following oral gavage with G.acuta,the whole plant extract(39.90 mg/kg).Plasma samples were processed using liquid–liquid extraction.The analytes and paeoniflorin(internal standard[IS])were separated using an Acquity?UPLC ethylene bridged hybrid amide column(2.1 mm×100 mm,1.7μm)with isocratic elution using a mobile phase consisting of acetonitrile and 0.1%formic acid in water(80:20,v/v)at a flow rate of 0.4 mL/min.Quantification was performed using multiple reaction monitoring of the fragmentation transitions at m/z 401.1→179.0,403.1→195.0,419.1→179.0,and 525.2→449.1 for gentiopicroside,sweroside,swertiamarin,and the IS,respectively.Results:The linearity of the analytical response was good and the calibration curves were linear over concentration ranges of 1.20–192.0,0.40–159.0,and 0.20–209.3 ng/mL for gentiopicroside,sweroside,and swertiamarin,respectively.The extraction recovery was in the range of 84.72%–91.34%,84.58%–93.43%,and 82.75%–91.37%for gentiopicroside,sweroside,and swertiamarin,respectively.Conclusions:The method was successfully used to evaluate the pharmacokinetic parameters of gentiopicroside,sweroside,and swertiamarin in beagle dogs.