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Triterpenoids

Distribution by Scientific Domains
Chemistry73%
Medical Sciences16%
Life Sciences8%

Kinds of Triterpenoids

  • new triterpenoid
    		•

    Terms modified by Triterpenoids

  • triterpenoid glycoside
    		•
  • triterpenoid isolated
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  • triterpenoid saponin
    		•

    Selected Abstracts

    A New Ketone and a Known Anticancer Triterpenoid from the Leaves of Onosma limitaneum

    HELVETICA CHIMICA ACTA, Issue 2 2005
    Uddin Ahmad, Viqar
    A new ketone, onosmone (1), and a known anticancer triterpenoid, bauerenone, besides , -sitosterol glycoside were isolated for the first time from the CHCl3 extract of the leaves of Onosma limitaneum. The structures of these compounds were established on the basis of spectral and chemical evidence. [source]

    ChemInform Abstract: Schisanlactone G (I), a New 3,4-seco-Lanostane Triterpenoid from Schisandra sphenanthera.

    CHEMINFORM, Issue 38 2009
    Rong Ren
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

    ChemInform Abstract: A New 3,4-seco-Ursane Triterpenoid from Glyptopetalum sclerocarpum.

    CHEMINFORM, Issue 5 2001
    Uthai Sotanaphun
    Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

    Chemical Constituents of Polyalthia nemoralis

    HELVETICA CHIMICA ACTA, Issue 4 2007
    Xiu-Feng He
    Abstract Three new natural products, the taraxastane-type triterpenoid 1, the azafluorene-based constituent 2-hydroxyonychine (2), and the diterpenoid nemoralisin (3) were isolated from the EtOH extract of Polyalthia nemoralis, along with five known compounds. The structures of the new compounds were established by in-depth spectroscopic and mass-spectrometric analyses, as well as by chemical transformation. [source]

    A New Ketone and a Known Anticancer Triterpenoid from the Leaves of Onosma limitaneum

    HELVETICA CHIMICA ACTA, Issue 2 2005
    Uddin Ahmad, Viqar
    A new ketone, onosmone (1), and a known anticancer triterpenoid, bauerenone, besides , -sitosterol glycoside were isolated for the first time from the CHCl3 extract of the leaves of Onosma limitaneum. The structures of these compounds were established on the basis of spectral and chemical evidence. [source]

    The sacred lotus (Nelumbo nucifera), phytochemical and therapeutic profile

    JOURNAL OF PHARMACY AND PHARMACOLOGY: AN INTERNATI ONAL JOURNAL OF PHARMACEUTICAL SCIENCE, Issue 4 2009
    Dr Pulok K. Mukherjee
    Abstract ObjectivesNelumbo nucifera Gaertn. (Nymphaeaceae), also known as sacred lotus, is a well known medicinal plant. This article reviews the traditional uses, phytochemistry and therapeutic reports on different parts of N. nucifera viz. the seeds, rhizomes, leaves and flowers. This review also describes various compounds isolated from different parts of this plant and the therapeutic benefits derived from those phytoconstituents. Key findings There are several therapeutic benefits of this plant for which different parts are used. The extracts of rhizomes, seeds, flowers and leaves have been reported to have varied therapeutic potential. Several bioactive compounds have been derived from these plant parts belonging to different chemical groups, including alkaloids, flavonoids, glycosides, triterpenoid, vitamins etc., which all have their own therapeutic impact. Thus, the pharmacological effects and various active ingredients of different parts of N. nucifera are well understood. Summary In this review we explore the current pharmaceutical, phytochemical and pharmacological knowledge about this well known plant species as well as several emerging aspects for research on N. nucifera. [source]

    Polyporenic acid C induces caspase-8-mediated apoptosis in human lung cancer A549 cells

    MOLECULAR CARCINOGENESIS, Issue 6 2009
    Hui Ling
    Abstract Lung cancer continues to be the leading cause of cancer-related mortality worldwide. This warrants the search for new and effective agents against lung cancer. We and others have recently shown that lanostane-type triterpenoids isolated from the fungal species Poria cocos (P. cocos) can inhibit cancer growth. However, the mechanisms responsible for the anticancer effects of these triterpenoids remain unclear. In this study, we investigated the effect of polyporenic acid C (PPAC), a lanostane-type triterpenoid from P. cocos, on the growth of A549 nonsmall cell lung cancer cells (NSCLC). The results demonstrate that PPAC significantly reduced cell proliferation via induction of apoptosis as evidenced by sub-G1 analysis, annexin V-FITC staining, and increase in cleavage of procaspase-8, -3, and poly(ADP-ribose)-polymerase (PARP). However, unlike our previously reported lanostane-type triterpenoid, pachymic acid, treatment of cells with PPAC was not accompanied by disruption of mitochondrial membrane potential and increase in cleavage of procaspase-9. Further, PPC-induced apoptosis was inhibited by caspase-8 and pan caspase inhibitors but not by a caspase-9 inhibitor. Taken together, the results suggest that PPAC induces apoptosis through the death receptor-mediated apoptotic pathway where the activation of caspase-8 leads to the direct cleavage of execution caspases without the involvement of the mitochondria. Furthermore, suppressed PI3-kinase/Akt signal pathway and enhanced p53 activation after PPAC treatment suggests this to be an additional mechanism for apoptosis induction. Together, these results encourage further studies of PPAC as a promising candidate for lung cancer therapy. © 2008 Wiley-Liss, Inc. [source]

    Erythrodiol, a natural triterpenoid from olives, has antiproliferative and apoptotic activity in HT-29 human adenocarcinoma cells

    MOLECULAR NUTRITION & FOOD RESEARCH (FORMERLY NAHRUNG/FOOD), Issue 5 2008
    M. Emília Juan
    Abstract Erythrodiol is the precursor of pentacyclic triterpenic acids present in Olea Europaea. Although olive oil and some of its constituents are reported to have anticarcinogenic activities, erythrodiol has not been assessed in its cell biological functions in detail. We therefore determined its effects on cell growth and apoptosis in human colorectal carcinoma HT-29 cells. Proliferation, cytotoxicity, and apoptosis were measured by fluorescence-based techniques. Erythrodiol inhibited cell growth with an EC50 value of 48.8 ± 3.7 ,M without any cytotoxic effects in a concentration range up to 100 ,M. However, exposure of cells for 24 h to 50, 100, and 150 ,M erythrodiol increased caspase-3-like activity by 3.2-, 4.8-, and 5.2-fold over that in control cells. We here demonstrate for the first time that, in colon adenocarcinoma cells, erythrodiol exerts antiproliferative and proapoptotic activity. [source]

    Antioxidant diterpenoids from the roots of Salvia barrelieri

    PHYTOCHEMICAL ANALYSIS, Issue 4 2009
    Ufuk Kolak
    Abstract Introduction The phytochemical and biological studies carried out on Salvia species showed that their extracts and constituents have various biological activities. Objective The aim of this study was the isolation of diterpenoids from the roots of Salvia barrelieri Ettling and the determination of the antioxidant activity. Methodology Chromatographic methods were used for fractionation and isolation, respectively. Structure elucidation was established by spectroscopic methods. Five antioxidant assays were performed. Results Three new abietane diterpenoids barreliol, royleanone 12-methyl ether and 7-epi-salviviridinol, and six known diterpenoids, with a known dammarane triterpenoid, pyxinol were isolated. The absolute stereochemistry of pyxinol was confirmed by X-ray analysis. Conclusion Taxodione exhibited the highest antioxidant activity among the tested compounds. Copyright © 2009 John Wiley & Sons, Ltd. [source]

    The role of triterpenoid on reactive oxygen scavenging system: Approach from the new chemiluminescence system (XYZ system)

    BIOFACTORS, Issue 1-4 2000
    Kazuyoshi Okubo
    Abstract We propose that the reactive oxygen species/hydrogen donor/mediator system (XYZ system) is a new chemiluminescence system for the measurement of reactive oxygen scavenging activity. By using this method, we demonstrated the role of triterpenoid on a reactive oxygen scavenging system. DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) conjugated saponin from soybean, produced a low level light emission in the presence of H_2O_2 (X) and gallic acid (Y). The soybean saponin acted as a mediator (Z) on the reactive oxygen scavenging system. When comparing the data of photon emission properties of saponin with that of cholic acids, it concludes that DDMP moiety of soybean saponin plays an important role rather than the aglycon moiety in the radical scavenging system. [source]

    Vinyl Sulfoxides as Stereochemical Controllers in Intermolecular Pauson,Khand Reactions: Applications to the Enantioselective Synthesis of Natural Cyclopentanoids

    CHEMISTRY - A EUROPEAN JOURNAL, Issue 21 2004
    Marta Rodríguez Rivero
    Abstract The use of sulfoxides as chiral auxiliaries in asymmetric intermolecular Pauson,Khand reactions is described. After screening a wide variety of substituents on the sulfur atom in ,,,-unsaturated sulfoxides, the readily available o -(N,N -dimethylamino)phenyl vinyl sulfoxide (1,i) has proved to be highly reactive with substituted terminal alkynes under N -oxide-promoted conditions (CH3CN, 0,°C). In addition, these Pauson,Khand reactions occurred with complete regioselectivity and very high diastereoselectivity (de=86,>96,%, (S,RS) diastereomer). Experimental studies suggest that the high reactivity exhibited by the vinyl sulfoxide 1,i relies on the ability of the amine group to act as a soft ligand on the alkyne dicobalt complex prior to the generation of the cobaltacycle intermediate. On the other hand, both theoretical and experimental studies show that the high stereoselectivity of the process is due to the easy thermodynamic epimerization at the C5 center in the resulting 5-sulfinyl-2-cyclopentenone adducts. When it is taken into account that the known asymmetric intermolecular Pauson,Khand reactions are limited to the use of highly reactive bicyclic alkenes, mainly norbornene and norbornadiene, this novel procedure constitutes the first asymmetric version with unstrained acyclic alkenes. As a demonstration of the synthetic interest of this sulfoxide-based methodology in the enantioselective preparation of stereochemically complex cyclopentanoids, we have developed very short and efficient syntheses of the antibiotic (,)-pentenomycin I and the (,)-aminocyclopentitol moiety of a hopane triterpenoid. Se ha estudiado la utilización de sulfóxidos como auxiliares quirales en reacciones de Pauson,Khand intermoleculares. Tras considerar una amplia variedad de vinil sulfóxidos diferentemente sustituidos en el átomo de azufre, se ha encontrado que el o -(N,N -dimetilamino)fenil sulfóxido (1,i) presenta una elevada reactividad frente a alquinos terminales en reacciones de Pauson,Khand. Además, estas reacciones transcurren con regioselectividades completas y diastereoselectividades muy elevadas (ed=86,>96,%). Estudios teóricos y experimentales sugieren que la gran reactividad mostrada por el vinil sulfóxido 1,i se debe a la capacidad del grupo amino para coordinarse al complejo de dicobalto del alquino, favoreciendo así la posterior formación del cobaltaciclo intermedio. Por otro lado, estudios tanto teóricos como experimentales han demostrado que la elevada diastereoselectividad del proceso es consecuencia de la fácil epimerización termodinámica en la posición C-5 de las 5-sulfinil-2-ciclopentenonas finales. Teniendo en cuenta que hasta el momento la reacción de Pauson,Khand intermolecular estaba limitada al empleo de alquenos bicíclicos muy reactivos, principalmente norborneno y norbornadieno, este nuevo procedimiento constituye la primera versión asimétrica con alquenos acíclicos no tensionados. Como demostración de la utilidad sintética de esta nueva metodología en la preparación enantioselectiva de sistemas ciclopentánicos complejos, se han desarrollado síntesis muy eficaces del antibiótico (,)-pentenomicina I y de la unidad de aminociclopentitol de un triperpenoide. [source]

    Hydroxylation of the Triterpenoid Nigranoic Acid by the Fungus Gliocladium roseum YMF1.00133

    CHEMISTRY & BIODIVERSITY, Issue 2 2007
    Jin-Yan Dong
    Abstract The ability of the fungus Gliocladium roseum YMF1.00133 to transform the bioactive nigranoic acid (=(24Z)-9,19-cyclo-3,4-secolanosta-4(28),24-diene-3,26-dioic acid) was investigated. Three new products from the co-cultures of nigranoic acid and G.,roseum YMF1.00133 were obtained by employing a combination of Sephadex LH-20 and silica-gel column chromatography. The major metabolite was identified as 15, -hydroxynigranoic acid, and the minor metabolites as 6,,15, -dihydroxynigranoic acid and 7,,15, -dihydroxynigranoic acid by mass spectrometry and NMR spectroscopy. This is the first report of the biotransformation of the A-ring-secocycloartene triterpenoid, nigranoic acid. [source]

    Hypotheses for the origin and early evolution of triterpenoid cyclases

    GEOBIOLOGY, Issue 1 2007
    W. W. FISCHER
    ABSTRACT Hopanes and steranes are found almost universally in the sedimentary rock record where they often are used as proxies for aerobic organisms, metabolisms, and environments. In order to interpret ancient lipid signatures confidently we require a complementary understanding of how these modern biochemical pathways evolved since their conception. For example, generally it has been assumed that hopanoid biosynthesis was an evolutionary predecessor to steroid biosynthesis. Here we re-evaluate this assumption. Using a combined phylogenetic and biochemical perspective, we address the evolution of polycyclic triterpenoid biosynthesis and suggest several constraints on using these molecules as aerobic biomarkers. Amino acid sequence data show that the enzymes responsible for polycyclic triterpenoid biosynthesis (i.e. squalene and 2,3-oxidosqualene cyclases) are homologous. Numerous conserved domains correspond to active sites in the enzymes that are required to complete the complex cyclization reaction. From these sites we develop an evolutionary analysis of three independent characters to explain the evolution of the major classes of polycyclic triterpenoids. These characters are: (i) the number of unfavourable anti-Markovnikov ring closures, (ii) all-chair (CCC) or chair-boat-chair (CBC) substrate conformation, and (iii) the choice between squalene and 2,3-oxidosqualene as the substrate. We use these characters to construct four competing phylogenies to describe the evolution of polycyclic triterpenoid biosynthesis. The analysis suggests that malabaricanoids would be the most ancient polycyclic triterpenoids. The two most parsimonious evolutionary trees are the ones in which hopanoid and steroid cyclases diverged from a common ancestor. The transition from a CCC- to CBC-fold marks the major divergence in the evolution of these pathways, and it is diagnosable in the geological record. However, this transition does not require the simultaneous adoption of the aerobic substrate, 2,3-oxidosqualene, because these characters are controlled by independent parts of the enzyme. [source]

    Study on the Constituents of Roots of Aceriphyllum rossii

    HELVETICA CHIMICA ACTA, Issue 9 2010
    Le Thi Kim Van
    Abstract A new stereoisomer of a tetrahydrofuranoid lignan, acerifuranoid A (1), and two new oleanane-type triterpenoids, aceriphyllic acids J and K (2 and 3), were isolated from the roots of Aceriphyllum rossii. Their structures were elucidated on the basis of spectroscopic analyses and chemical evidence. These isolated compounds exhibited weak cytotoxic activity against various cancer cell lines with IC50>150,,M. [source]

    New Acylated Secoiridoid Glucosides from Gentiana straminea (Gentianaceae)

    HELVETICA CHIMICA ACTA, Issue 2 2009
    Min Xu
    Abstract Two new acylated secoiridoid glucosides, 4,-acetyl-6,-{[2-hydroxy-3-(1- , - D -glucopyranosyloxy)]benzoyloxy}sweroside and 3,,4,-diacetyl-6,-{[2-hydroxy-3-(1- , - D -glucopyranosyloxy)]benzoyloxy}swertiamarin, named gentistraminosides A (1) and B (2), were isolated from the MeOH extract of Gentiana stramineaMaxim (Gentianaceae), together with twelve known ones, including eight iridoid and secoiridoid glucosides, macrophylloside A (3), loganic acid (4), secologanic acid (5), swertiamarin (6), gentiopicroside (7), loganic acid methyl ester (8), 6,- O - , - D -glucopyranosyl gentiopicroside (9), and loganic acid 11- O - , - D -glucopyranosyl ester (10), one flavone C -glucoside, isovitexin (11), one chromenecarboxylic acid glycosyl ester, macrophylloside D (12), and two triterpenoids, 1,,2,,3,,24-tetrahydroxyolean-12-en-28-oic acid (13), and 3,,6,,24-trihydroxyolean-12-en-28-oic acid (14). Their structures were determined by means of detailed spectroscopic (NMR and MS) analysis. [source]

    Highly Oxygenated Triterpenoids from the Marine Red Alga Laurencia mariannensis (Rhodomelaceae)

    HELVETICA CHIMICA ACTA, Issue 10 2008
    Nai-Yun Ji
    Abstract Two new and one known squalenoid-derived triterpenoids, namely, laurenmariannol (1) and (21,)-21-hydroxythyrsiferol (2), and the known thyrsiferol (3) were isolated and identified from the marine red alga Laurencia mariannensis, which was collected off the coast of Hainan and Weizhou Islands of China. The structures of these compounds were established by means of spectroscopic analyses, as well as by comparison with literature data. Compounds 1 and 2 displayed significant cytotoxic activity against P-388 tumor cells with IC50 values of 0.6 and 6.6,,g/ml, respectively. [source]

    Triumfettamide and Triumfettoside Ic, Two Ceramides and Other Secondary Metabolites from the Stems of Wild Triumfetta cordifoliaA.

    HELVETICA CHIMICA ACTA, Issue 7 2008
    Rich. (Tiliaceae)
    Abstract Two new ceramides, triumfettamide (1) and triumfettoside Ic (2), characterized as (2R,6Z)-2-hydroxy- N -[(2S,3S,4R)-1,3,4-trihydroxyhexacosan-2-yl]heptadec-6-enamide and (2R)- N -{(1S,2R,3E,6Z, 9Z,12Z,15Z)-1-[(, - D -glucopyranosyloxy)methyl]-2-hydroxyheneicosa-3,6,9,12,15-pentaen-1-yl}-2-hydroxytetradecanamide, respectively, were isolated from the stems of Triumfetta cordifoliaA. Rich. besides eight known secondary metabolites identified as heptadecanoic acid, , -sitosterol glucopyranoside, friedelin, lupeol, betulin, maslinic acid, 2-hydroxyoleanolic acid and the mixture of stigmasterol and , -sitosterol. Their structures were determined on the basis of spectroscopic methods as well as HR-MALDI-FT-ICR-MS analysis, chemical transformation, and by comparison of their physical and spectral data with those reported in the literature and with authentic specimens for some known compounds. Five pentacyclic triterpenoids, friedelin, lupeol, betulin, maslinic acid, and 2-hydroxyoleanolic acid, have been isolated from Triumfetta genus for the first time. [source]

    Three New Triterpenoids from Dracocephalum forrestii

    HELVETICA CHIMICA ACTA, Issue 12 2006
    Gan-Peng Li
    Abstract From the whole plant of Dracocephalum forrestii (Labiatae), three new and nine known triterpenoids were isolated. The new compounds were identified as (3,,18,)-20,28-epoxy-3-hydroxyurs-21-en-28-one (1), (3,,18,)-urs-21-ene-3,20,28-triol (2), and (3,,18,,19,)-ursane-3,20,28-triol (3) by means of in-depth spectroscopic analysis. [source]

    Uncommon Sesquiterpenoids and New Triterpenoids from Jatropha neopauciflora (Euphorbiaceae)

    HELVETICA CHIMICA ACTA, Issue 1 2006
    Abraham García
    Abstract Eight new terpenoids (1,8) were isolated from the bark of Jatropha neopauciflora, together with eight known compounds. The new isolates include the sesquiterpenoids (1R,2R)-diacetoxycycloax-4(15)-ene (1); (1R,2R)-dihydroxycycloax-4(15)-ene (2), (2R)- , -cadin-4-ene-2,10-diol (3), (2R)- , -cadina-4,9-dien-2-ol (4), (1R,2R)-dihydroxyisodauc-4-en-14-ol (5) and its acetonide 6 (artifact), as well as the two triterpenoids (3,,16,)-16-hydroxylup-20(29)-en-3-yl (E)-3-(4-hydroxyphenyl)prop-2-enoate (7) and (3,,16,)-16-hydroxyolean-18-en-3-yl (E)-3-(4-hydroxyphenyl)prop-2-enoate (8). The structures of these compounds were established by extensive 1D- and 2D-NMR spectroscopic methods, and their absolute configurations were determined by circular-dichroism (CD) experiments, and by X-ray crystallographic analysis (compound 7; Fig.,3). A plausible biosynthesis of the sesquiterpenoids 1,5 is proposed (Scheme), starting from (,)-germacrene D as the common biogenetic precursor. [source]

    Insect antifeedant and growth regulating activities of neem seed oil , the role of major tetranortriterpenoids

    JOURNAL OF APPLIED ENTOMOLOGY, Issue 7-8 2000
    T. R. Govindachari
    Selective elimination of triterpenoids by preparative high-performance liquid chromatography, incorporation of the eliminated compounds in defined concentrations and bioassaying the resultant fractions against Spodoptera litura indicated the necessity to quantify major triterpenoids for correlation of bioactivity of neem oil. [source]

    Molluscicides from some common medicinal plants of eastern Uttar Pradesh, India

    JOURNAL OF APPLIED TOXICOLOGY, Issue 1 2010
    Sunil Kumar Singh
    Abstract Many aquatic snails act as intermediate hosts for the larvae of trematodes, Fasciola hepatica and Fasciola gigantica, which cause the diseases fascioliasis and schistosomiasis. The WHO has tested several thousands of synthetic compounds for the control of the snail host. Although effective, these molluscicides have so far not proved themselves to be entirely satisfactory. With a growing awareness of environmental pollution, efforts are being made to discover molluscicidal products of plant origin. Being products of biosynthesis, these are potentially biodegradable in nature. Several groups of compounds present in various plants have been found to be toxic to target organisms at acceptable doses ranging from <1 to 100,ppm. Common medicinal plants, i.e. Thevetia peruviana, Alstonia scholaris (Family; Apocynaceae), Euphorbia pulcherima and Euphorbia hirta (Family; Euphorbiaceae), have potent molluscicidal activity against freshwater snails. The toxicological actions of Thevetia peruviana may be due to the presence of apigenin-5-methyl ether (flavonoid) and triterpenoid glycosides, while a number of alkaloids (pseudo-akuammigine in addition to betulin, ursolic acid and ,-sitosterol), steroids and triterpenoids are present in Alstonia scholaris and the diterpenoids, pulcherrol, ,-sitosterol, hentriacontane, ellagic acid and ,-amyrin are present in Euphorbia hirta and in Euphorbia pulcherima. Although, at present very little literature is available on the control of vector snails through plant origin pesticides, an attempt has been made in this review to assemble all the known information on molluscicidal properties of common medicinal plants of eastern Uttar Pradesh, India, which might be useful for the control of harmful snails. Copyright © 2009 John Wiley & Sons, Ltd. [source]

    Hepatoprotective activity of Terminalia catappa L. leaves and its two triterpenoids

    JOURNAL OF PHARMACY AND PHARMACOLOGY: AN INTERNATI ONAL JOURNAL OF PHARMACEUTICAL SCIENCE, Issue 11 2004
    Jing Gao
    The aim of this study was to evaluate the effect of the chloroform extract of Terminalia catappa L. leaves (TCCE) on carbon tetrachloride (CCI4)-induced acute liver damage and D-galactosamine (D-GaIN)-induced hepatocyte injury. Moreover, the effects of ursolic acid and asiatic acid, two isolated components of TCCE, on mitochondria and free radicals were investigated to determine the mechanism underlying the action of TCCE on hepatotoxicity. In the acute hepatic damage test, remarkable rises in the activity of serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) (5.7- and 2.0-fold) induced by CCI4 were reversed and significant morphological changes were lessened with pre-treatment with 50 and 100 mg kg,1 TCCE. In the hepatocyte injury experiment, the increases in ALT and AST levels (1.9- and 2.1-fold) in the medium of primary cultured hepatocytes induced by D-GaIN were blocked by pre-treatment with 0.05, 0.1, 0.5 gL,1 TCCE. In addition, Ca2+ -induced mitochondrial swelling was dose-dependently inhibited by 50,500 ,m ursolic acid and asiatic acid. Both ursolic acid and asiatic acid, at concentrations ranging from 50 to 500 ,m, showed dose-dependent superoxide anion and hydroxyl radical scavenging activity. It can be concluded that TCCE has hepatoprotective activity and the mechanism is related to protection of liver mitochondria and the scavenging action on free radicals. [source]

    Simultaneous qualification and quantification of eight triterpenoids in Radix Achyranthis Bidentatae by high-performance liquid chromatography with evaporative light scattering detection and mass spectrometric detection

    JOURNAL OF SEPARATION SCIENCE, JSS, Issue 6 2007
    Juan Li
    Abstract An HPLC with evaporative light scattering detection (ELSD) and ESI-MS was established for the simultaneous determination of eight triterpenoids in Radix Achyranthis Bidentatae. The optimal chromatographic conditions were achieved on a Zorbax C18 column by linear gradient elution with 0.08% v/v aqueous formic acid and ACN as the mobile phase at the flow rate of 0.8 mL/min. Temperature for the detector drift tube was set at 101°C and the nitrogen flow rate was 2.8 L/min. The identities of the analytes were accomplished by comparing retention times and mass data with those of reference compounds. The validation of the method included tests of linearity, sensitivity, repeatability, recovery, and stability. All the calibration curves of the eight triterpenoids showed good linear regression (R2 >0.997) within the test ranges. The method provides desirable repeatability with overall intra- and interday variations of less than 4.9%. The obtained recoveries varied between 93.6 and 98.1% while the RSDs were below 3.9% (n = 3). The analysis results indicate that the content of investigated triterpenoids in Radix Achyranthis Bidentatae from different locations was greatly diverse, and the triterpenoids could be used as chemical markers for the discrimination of genuine and ungenuine crude drugs. [source]

    Structural determination of two new triterpenoids biotransformed from glycyrrhetinic acid by Mucor polymorphosporus

    MAGNETIC RESONANCE IN CHEMISTRY, Issue 2 2010
    Xiu Lan Xin
    Abstract Five hydroxylated derivatives of glycyrrhetinic acid by Mucor polymorphosporus were isolated. Among them, 6,, 7,-dihydroxyglycyrrhentic acid (2) and 27-hydroxyglycyrrhentic acid (3) are new compounds. Their chemical structures were identified by spectral methods including 2D-NMR. Copyright © 2009 John Wiley & Sons, Ltd. [source]

    Cucurbitane triterpenoids from Momordica charantia

    MAGNETIC RESONANCE IN CHEMISTRY, Issue 6 2007
    Qing-Yan Li
    Abstract Three new cucurbitane-type triterpenoid saponins, 23- O -,- D -allopyranosyl-5,,19-epoxycucurbita-6,24-diene-3,,22(S),23(S)-triol-3- O -,- D -glucopyranoside (1), 23- O -,- D -allopyranosyl-5,,19-epoxycucurbita-6,24-diene-3,,22(S),23(S)-triol-3- O -,- D -allopyranoside (2), and 23- O -,- D -allopyranosyl-5,,19-epoxycucurbita-6,24-diene-3,,19(R), 22(S),23(S)-tetraol-3- O -,- D -allopyranoside (3), named momordicoside M, N, and O, respectively, along with one known saponin momordicoside L (4), were isolated from the fresh fruits of Momordica charantia. The structures of these saponins were elucidated on the basis of chemical properties and spectral data. Copyright © 2007 John Wiley & Sons, Ltd. [source]

    Structural determination of seven new triterpenoids from Kadsura heteroclita by NMR techniques

    MAGNETIC RESONANCE IN CHEMISTRY, Issue 6 2007
    Wei Wang
    Abstract Seven new triterpenoids, namely heteroclitalactones G,M (1,7), were isolated from the ethanol extract of the stems of Kadsura heteroclita. Structures of these compounds were characterized by extensive 1D and 2D NMR spectroscopic analyses. Copyright © 2007 John Wiley & Sons, Ltd. [source]

    Polyporenic acid C induces caspase-8-mediated apoptosis in human lung cancer A549 cells

    MOLECULAR CARCINOGENESIS, Issue 6 2009
    Hui Ling
    Abstract Lung cancer continues to be the leading cause of cancer-related mortality worldwide. This warrants the search for new and effective agents against lung cancer. We and others have recently shown that lanostane-type triterpenoids isolated from the fungal species Poria cocos (P. cocos) can inhibit cancer growth. However, the mechanisms responsible for the anticancer effects of these triterpenoids remain unclear. In this study, we investigated the effect of polyporenic acid C (PPAC), a lanostane-type triterpenoid from P. cocos, on the growth of A549 nonsmall cell lung cancer cells (NSCLC). The results demonstrate that PPAC significantly reduced cell proliferation via induction of apoptosis as evidenced by sub-G1 analysis, annexin V-FITC staining, and increase in cleavage of procaspase-8, -3, and poly(ADP-ribose)-polymerase (PARP). However, unlike our previously reported lanostane-type triterpenoid, pachymic acid, treatment of cells with PPAC was not accompanied by disruption of mitochondrial membrane potential and increase in cleavage of procaspase-9. Further, PPC-induced apoptosis was inhibited by caspase-8 and pan caspase inhibitors but not by a caspase-9 inhibitor. Taken together, the results suggest that PPAC induces apoptosis through the death receptor-mediated apoptotic pathway where the activation of caspase-8 leads to the direct cleavage of execution caspases without the involvement of the mitochondria. Furthermore, suppressed PI3-kinase/Akt signal pathway and enhanced p53 activation after PPAC treatment suggests this to be an additional mechanism for apoptosis induction. Together, these results encourage further studies of PPAC as a promising candidate for lung cancer therapy. © 2008 Wiley-Liss, Inc. [source]

    Simultaneous quantification of three major triterpenoids in radix asteris by high-performance liquid chromatography with evaporative light scattering detection

    PHYTOCHEMICAL ANALYSIS, Issue 3 2009
    Yaping Tian
    Abstract Introduction Radix asteris, with triterpenoids as its main pharmacological effective compounds, has been widely used for moistening the lung, dispersing phlegm and relieving cough. Quantification of the triterpenoids is important for the quality control of Radix asteris. Objective To establish a high-performance liquid chromatography method with evaporative light scattering detection for simultaneous determination of three major triterpenoids, shionone, friedelin and epi-friedelinol, in Radix asteris. Methodology The optimal chromatographic conditions were achieved on an RP18 column with gradient elution by acetonitrile and 0.05% acetic acid in 22 min with ELSD set at an evaporating temperature of 40°C. Validation of the method included tests of linearity, sensitivity, precision, repeatability, stability and accuracy. Results All calibration curves showed good linear regression (r2 > 0.9991) within test ranges. The established method showed good precision and accuracy with overall intra-day and inter-day variations of 1.61,2.97 and 1.74,2.42%, respectively, and overall recoveries of 97.35,101.13% for the three compounds analysed. Conclusion The method developed was successfully applied to quantify the main triterpenoids in 14 Radix asteris samples. Copyright © 2009 John Wiley & Sons, Ltd. [source]

    Selective ultrasound-assisted extractions of lipophilic constituents from Betula alleghaniensis and B. papyrifera wood at low temperatures

    PHYTOCHEMICAL ANALYSIS, Issue 4 2007
    J.-M. Lavoie
    Abstract Betula alleghaniensis and B. papyrifera are widely distributed in the province of Québec (Canada) and, since these trees are valuable exports for the local lumber industry, large amounts of their residual ligneous biomass are available for further exploitation. Betula species are well known for their significant concentrations of triterpenes, some of which were recently discovered to present promising bioactivity. The secondary transformation of birch biomass could therefore become important for many industries, particularly the pharmaceutical industry. In the present study, extracts from birch sawdust were obtained using an optimised ultrasound-assisted extraction in which the careful choice of temperature permitted a selective extraction of the targeted triterpenes. Moreover, compared with the classical Soxhlet method, higher extraction yields were obtained in a shorter time. The lipophilic extracts obtained using dichloromethane as a solvent were analysed by GC-MS and the major compounds identified as lupane-type cyclic triterpenoids accompanied by the non-cyclic triterpene squalene. Numerous aliphatic long-chain fatty acids were also found in the extracts together with phytosterols. Betulonic acid and squalene, the major extract constituents for both B. alleghaniensis and B. papyrifera, are both bioactive molecules. Copyright © 2007 John Wiley & Sons, Ltd. [source]

    Quantitative determination of cytotoxic­Friedo-nor -oleanane derivatives from five morphological types of Maytenus ilicifolia (celastraceae) by reverse-phase high-performance liquid chromatography

    PHYTOCHEMICAL ANALYSIS, Issue 2 2002
    Waldemar Buffa Filho
    Abstract Five different morphological types of Maytenus ilicifolia of the same age and harvested under the same conditions showed distinct accumulations of some friedo-nor -oleananes. A rapid, sensitive and reliable reverse-phase HPLC method (employing an external standard) was used for the determination of the cytotoxic triterpenoids, 20,-hydroxymaytenin, 22,-hydroxymaytenin, maytenin, celastrol and pristimerin in each of the five types. Well resolved peaks with good detection response and linearity in the range­1.0,100,µg/mL were obtained. Copyright © 2002 John Wiley & Sons, Ltd. [source]