Iridoid glycosides kutkin, picroside i, and kutkoside from picrorrhiza kurroa benth inhibits the invasion and migration of mcf7 breast cancer cells through the down regulation of matrix metalloproteinases dharmender rathee a, madhavi thanki a, satish bhuva b, sheetal anandjiwala a, reena agrawal c. Loganic acid is an iridoid substrate converted to strictosidine which reacts with tryptamine, eventually leading to the indole alkaloids which include many biologically active compounds such as strychnine, yohimbine, vinca alkaloids, and ellipticine. Iridoid glycosides from gmelina philippensis request pdf. Bioactive iridoid glycosides from the whole plants of rehmannia. The ms spectra showed that the adduct ions of iridoid glycosides and the formate anion were diagnostic ions to distinguish iridoid glycosides with a carboxyl group at the c. The electrolyte was changed to borax to facilitate manual integration of analyte. Iridoid glycosides have laxative and antimicrobal properties. Iridoid and phenylethanoid glycosides from phlomis nissolii and p. On the basis of the spectroscopic data and a comparison with the published data in the literature, compound 1 was identi ed as aucubin5. Office of regulatory science, center for food safety and applied nutrition, u. Assignment of 1h and c nmr data for iridoid glycoside. Yun chen and ping li, structural characterization and identification of iridoid glycosides, saponins, phenolic acids and flavonoids in flos lonicerae japonicae by a fast liquid chromatography method with diode. Introduction the following iridoid glycosides have been isolated from the herb galium verum l asperuloside 14, 6, monotropein 46, scandoside, deacetylasperulosidic acid, geniposidic acid and asperulosidic acid 6.
Verbenalin is a chemical compound, classified as an iridoid glucoside, that is found in verbena officinalis. Protects against acetaminopheninduced liver injury in mice shancaitan,1,2 qiuxialu,1,2 yueyueshu,1,2 yiransun,1,2 fangchen,1,2 andlintang1,2. Iridoid glycoside concentrations are known to be genetically controlled in p. One new iridoid glycoside from hedyotis tenelliflora. The structure of 1 was established by interpretation and full assignments of nmr spectroscopic data. First isolated in 1962, catalpol was named for plants in the genus catalpa in which it was discovered. The structures were elucidated by 1d and 2dnmr spectroscopy, mass spectrometry, and chemical. Although iridoid glycosides have primarily been studied as antiherbivore defenses in leaves, these results indicate that they can also function to reduce the growth of. The species has become endangered to near extinction due to the unregulated collection from the wild, slower plant growth and ecological destruction of natural habitats. Morinda officinalis is a famous traditional chinese medicine containing iridoid glycoside compounds, such as monotropein and deacetylasperulosidic acid. Plant tissue is damaged both are put in contact and. Assefa e, alemayhu i, endale m, mammo f 2016 iridoid glycosides from the root of acanthus sennii.
The activity of the iridoid glycosides reptoside and 6deoxyharpagide as well as clerodane diterpenes and withaferin a may thus be responsible in part for the anti. Iridoid glycosides an overview sciencedirect topics. The group includes constituents such as limonene, phellandrene, cedrene etc. This indicated the potential of iridoid glycosides to affect the inflammatory process through the inhibition of ros production andor providing a radical scavenging effect during oxidative stress. Plant glycosides pdf the cyanogenic glycosides belong to the products of secondary metabolism, to the natural products of plants.
Pdf from the ethanolic extract of the aerial parts of globularia davisiana, a new iridoid glycoside, davisioside 1, was isolated. Iridoid glycosides from galium verum hungarian consortium. Methods and materials study system linaria dalmatica is a perennial species native to eurasia that escaped cultivation in north america during the early 1900s and since has become a. Extraction of iridoid glycosides from motherwort grass using. These bitter principles stimulates the release of gastrin in the digestive system, which in turn stimulates the secretions of bile and other digestive chemicals. Iridoid glycosides harvard catalyst profiles harvard catalyst. Total iridoid glycoside concentrations in extracts were not good predictors of variation in fungal growth, but several individual compounds had significant negative effects. Iridoid glycosides are a group of compounds that have a structure related to iridodial figure 11. Fifteen new and rare iridoid glucoside dimers, cornusides ao 115, and 10 known iridoid glucosides 1625 were isolated from the fruit of cornus officinalis. The presence of cyanogenic glycosides was determined in 70 plant species from the. Separation of five iridoid glycosides from lonicerae japonicae flos using highspeed countercurrent chromatography and their antiinflammatory and antibacterial activities.
Pdf the potential role of iridoid glycosides as feeding stimulants foreuphydryas chalcedona larvae was examined in three laboratory experiments. Two herbivoredeterrent iridoid glycosides reduce the in. Uses, benefits, properties, and effects of iridoid glycosides. Chemical investigation of the methanol extract of the aerial parts of buddleja asiatica resulted in the isolation of a new iridoid glycoside. A,b the phosphorylation at different sits of tau protein in hek293t cells transfected with wild type gsk3.
Extraction of iridoid glycosides from motherwort grass using various solvents. A new iridoid glucoside 1, named citrifolinoside a, was isolated from the leaves of morinda citrifolia along with the known iridoids asperuloside and asperulosidic acid. Bioactive iridoid glycosides from the whole plants of. Pdf iridoid and bisiridoid glycosides from globularia.
Iridoid glycosides from fruits reduce the growth of fungi associated with fruit rot article pdf available in journal of plant ecology 93. Proceedings of the 2nd annual international iridoid research. Copies of ir, ms, 1d and 2d nmr, and cd spectra for compounds 1 9 pdf. Iridoid glycosides fraction isolated from veronica ciliata. Iridoid glycosides and cucurbitacin glycoside from. The molecule from which the nonsugar moiety of a glycoside is derived is called the aglycones or genin. Iridoid glycosides from fruits reduce the growth of fungi. Iridoid and phenylethanoid glycosides from phlomis nissolii. Iridoid glycosides from the twigs of sambucus williamsii var. Pdf iridoid glycosides from globularia davisiana researchgate. Five new iridoid glucosides, 15, including two cistrans isomers, together with six known compounds were isolated from the whole plant of c. Food and drug administration, college park, md, usa. The genus globulariaglobulariaceae is represented by eight species in the.
Iridoid glycosides is a descriptor in the national library of medicines controlled vocabulary thesaurus, mesh medical subject headings. Researcharticle iridoid glycosides fraction isolated from veronica ciliata fisch. Hydrophilic iridoid glycosides and oligosaccharides are the major active ingredients of radix rehmanniae. Iridoid glycosides from the twigs of sambucus williamsii. The plant is the principle source of iridoid glycosides, picrosides i, ii and kutkoside used in various herbal drug formulations mainly as strong hepatoprotective and immune. A glycoside is an organic compound, usually of plant origin, and comprising a sugar portion linked to a nonsugar moiety in a particular manner. Iridoid glycoside constituents of stachys lanata toshihiro murata, yuka endo, toshio miyase, and fumihiko yoshizaki department of pharmacognosy, tohoku pharmaceutical university, 41 komatsushima 4chome aobaku, sendai 9818558, japan and school of pharmaceutical sciences. Analysis of oligosaccharides is a challenging task because they are highly. Hacettepe university, faculty of pharmacy, department of pharmacognosy, tr06100, ankaraturkey ali a.
Agnusoside 1 represents an unusual type of iridoid glycoside with its 6keto c4 nonsubstituted aglycone. In this paper, one new iridoid glycoside from the whole plant of h. Iridoid glycosides from the leaves of sambucus ebulus journal of natural products six new iridoid glycosides 1. Cornusides ao, bioactive iridoid glucoside dimers from. Iridoid glycosides and phenolic glycosides from buddleja asiatica. John wadsworth, president of tahitian noni international, inc. Pedersen a 1 chrysoula gousiadou a tetsuo kokubun b dirk albach c rilka taskova d phil j. Their structures were elucidated by extensive spectroscopic techniques. Iridoid glycosideskutkin, picroside i, and kutkoside from.
Comparative estimation of major iridoid glucosides from. Studies of iridoid glycosides using liquid chromatography. Comparison of anthraquinones, iridoid glycosides and. Loganin is an iridoid glycoside of interest as both an intermediate in the biosynthesis of indole alkaloids in plants and as a bioactive compound itself. The new iridoid glucoside, 7,8epiantirrinoside, found in l.
Pdf iridoid glucosides from viburnum tinus sebastiano. Saponins are plant glycosides with a triterpene or steroid aglycone. Prediction the contents of fructose, glucose, sucrose, fructooligosaccharides and iridoid glycosides in morinda officinalis radix using nearinfrared spectroscopy author links open overlay panel qingxiu hao a jie zhou b li zhou a liping kang a tiegui nan a yi yu c lanping guo a. Phenylethanoid glycosides and iridoid glycosides protect the plantago genus against pathogens and herbivores and also function as allelopathic signals to mediate plantplant interactions pankoke. New iridoid glucosides from caryopteris incana thunb. These four species differed in their feeding strategy, ranging from generalist to monophagous specialist. Iridoid and phenylethanoid glycosides from euphrasia pectinata. The adults of checkspot butterflies, euphydrias spp. Glycosides play numerous important roles in living organisms.
These new chemical structures were established through spectroscopic analysis uv, ir, hresims, 1d and 2d nmr. Fruit iridoid glycosides reduce fungal growth page 3 of 10 similar numbers of ripe fruits were collected from the same individuals in early august. Boschnaloside has been isolated from several other species including euphasia pectinata and pedicularis verticillata. Iridoid and bisiridoid glycosides from globularia cordifolia article pdf available in zeitschrift fur naturforschung c 5856.
Iridoids1 free download as powerpoint presentation. It is one of the sleeppromoting soporific components in verbena officinalis. A compilation of new naturally occurring iridoid glycosides, iridoid aglycones, iridoid derivatives and bisiridoids reported during 19942005 is provided with available physical and spectral data. Phytochemical studies for quantitative estimation of iridoid.
The iridoids produced by plants act primarily as a defense against herbivores or against infection by microorganisms. Separation of five iridoid glycosides from lonicerae japonicae flos using highspeed countercurrent chromatography and. Bot stud phytochemical studies for quantitative estimation of iridoid glycosides in picrorhiza kurroa royle phalisteen sultan 0 arif jan 0 qazi pervaiz 0 0 csirplant biotechnology division, indian institute of integrative medicine, sanatnagar, srinagar, kashmir, india background. Iridoid glycosides from lonicera quinquelocularis pdf free. Glycoside purvi kakrani, glycosides, lbriper 2 glycoside is an organic compound, usually of plant origin, that is composed of a sugar portion linked to a nonsugar moiety. Many plants store chemicals in the form of inactive glycosides. We analyzed the chemical composition of the iridoid glycosides fraction igf isolated from v. Copies of ir, ms, 1d and 2d nmr, and cd spectra for compounds 19 pdf.
Iridoid glycosides from the leaves of sambucus ebulus. Iridoid glycoside concentration also varies with the developmental state of. Iridoid and flavone glycosides from asystasia gangetica subsp. The discovery of these compounds further expands our knowledge of the structural diversity of the glycosides produced by the plant. Introduction terpenoid terpenes constitute one of the most important groups of essential oils. They are biosynthetically derived from 8oxogeranial. Three phenylethanoid glycosides 1, 2, 3 and one iridoid glycoside 4 were isolated from aerial parts of veronica chamaedrys l. Prediction the contents of fructose, glucose, sucrose. On the basis of spectral analysis, the structures of these compounds were.
Pages in category iridoid glycosides the following 11 pages are in this category, out of 11 total. Bioactive iridoid glycosides from the whole plants of rehmannia chingii yanfei liu, guoru shi, xin wang, chunlei zhang, yan wang, ruoyun chen, and dequan yu state key laboratory of bioactive substance and function of natural medicines, institute of materia medica, chinese academy of medical sciences and peking union. Iridoid glucosides in the genus veronica plantaginaceae. Iridoid and flavone glycosides from asystasia gangetica. Two new iridoid glycosides, scalbidoside and albidoside were isolated from the methanolic extract of the aerial parts of scutellaria albida subsp. Separation of five iridoid glycosides from lonicerae. Iridoids are typically found in plants as glycosides, most often bound to glucose.
Antiinflammatory iridoids of botanical origin ncbi. Pdf iridoid glycosides from fruits reduce the growth of. Structural characterization of iridoid glucosides by ultra. The linkage between the sugar and the aglycones is a hemiacetal linkage. The aim of the study was to develop a novel and sensitive liquid chromatographytandem mass spectrometry lcmsms method for the simultaneous determination of the two isomeric iridoid. Many secondary plant compounds are involved in defense against both insect herbivores and pathogens.
Two secondary plant compounds of plantago lanceolata, the iridoid glycosides catalpol and its precursor aucubin, are well known for their deterrent effects on generalist. Incarvillea emodi bignoniaceae is a rich source of bioactive iridoid glucosides. Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. Proceedings of the 2nd annual international iridoid research symposium sponsored by tahitian noni international, inc.
Jan 17, 2007 read iridoid glycosides and cucurbitacin glycoside from neopicrorhiza scrophulariiflora. Article information, pdf download for iridoid glycosides and phenolic glycosides from. Supporting information for iridoid glycoside constituents. Abstractfoaming glycosides, traditionally known for their detergent. Hacettepe university, faculty of science, department of biology, tr06532, ankaraturkey received 01. Iridoid, phenylethanoid and monoterpene glycosides from phlomis sieheana tayfun ers oz. This natural product falls in the class of iridoid glycosides, which are simply monoterpenes with a glucose molecule attached. Picrorhiza kurroa royle commonly known as kutki or kutaki is an important medicinal plant in.
Here, in this study we have developed a simple and fast hplcdad method for the total comparative estimation of these two major iridoids from different parts of. Their growth rates were assessed in vitro in the presence of varying concentrations of pure loganin, one of the most abundant iridoid glycosides in fruits, as well as fruit extracts containing a mix of at least seven different iridoid glycosides. Phytochemical studies for quantitative estimation of. Four new bis iridoid glycosides, saungmaygaosides ad 14, and six known iridoid glycosides 510 were isolated from the nbutanol extract of the stems of picrorhiza kurroa collected in myanmar. Among these, 25 compounds presented in both plants. Plant ecology iridoid glycosides from fruits pages 110. Iridoid glycosides from the leaves of morinda citrifolia. In this study saponin was isolated from moringa oleifera pods. In addition, japaneseturkish research groups have also reported some iridoid and phenylethanoid glycosides from p. Pdf the role of iridoid glycosides in hostplant specificity of. The plant is the principle source of iridoid glycosides, picrosides i, ii and kutkoside used in various herbal drug formulations mainly as strong hepatoprotective and immunemodulatory compound. The iridoid glycoside, syringopicroside 48, is the main active constituent and has been shown to possess antiinflammatory, broadspectrum antimicrobial, antiviral, and.
Descriptors are arranged in a hierarchical structure, which enables searching at various levels of specificity. Chemotaxonomy of plantago using iridoid glucosides and caffeoyl phenylethanoid glycosides has been carried out by ronsted, gobel, franzyk, et al. To humans and other mammals, iridoids are often characterized by a deterrent bitter taste. Iridoid, phenylethanoid and monoterpene glycosides from. Loganic acid methyltransferase catalyzes the methylation of a monoterpenoid glycoside precursor to produce loganin and demonstrates stereospecificity for the 6 s. The iridoid glycosides c1 are polyhydroxyl linked and polyglycoside formed, and most of them are. Picrorhiza kurroa royle commonly known as kutki or kutaki is an important medicinal plant in ayurvedic system of medicine and has traditionally been used to treat disorders of the liver and upper respiratory tract. Iridoid glycosides from galium verum sciencedirect. Pdf a new iridoid glycoside from linaria genestifolia.
Read iridoid glycosides and insect feeding preferences. All of the isolates were assayed for antivpr activity, using trexhelavpr cells. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. From the mother liquor obtained on recrystallizatio. Iridoid glycosides from lonicera quinquelocularis pdf. Iridoid glycosides from the root of acanthus sennii journal. Fruits were collected from multiple branches throughout the shrub to obtain a representative. There were 26 anthraquinones, 15 triterpenes, and 8 iridoid glycosides identified in the root extracts of m. From the mother liquor obtained on recrystallization of asperuloside, v3 iridoid and daphylloside were also obtained. Fate of ingested iridoid glycosides in lepidopteran herbivores.