Rational and Efficient Preparative Isolation of Natural Products by MPLC-UV-ELSD based on HPLC to MPLC Gradient Transfer.

Abstract:

:In natural product research, the isolation of biomarkers or bioactive compounds from complex natural extracts represents an essential step for de novo identification and bioactivity assessment. When pure natural products have to be obtained in milligram quantities, the chromatographic steps are generally labourious and time-consuming. In this respect, an efficient method has been developed for the reversed-phase gradient transfer from high-performance liquid chromatography to medium-performance liquid chromatography for the isolation of pure natural products at the level of tens of milligrams from complex crude natural extracts. The proposed method provides a rational way to predict retention behaviour and resolution at the analytical scale prior to medium-performance liquid chromatography, and guarantees similar performances at both analytical and preparative scales. The optimisation of the high-performance liquid chromatography separation and system characterisation allows for the prediction of the gradient at the medium-performance liquid chromatography scale by using identical stationary phase chemistries. The samples were introduced in medium-performance liquid chromatography using a pressure-resistant aluminium dry load cell especially designed for this study to allow high sample loading while maintaining a maximum achievable flow rate for the separation. The method has been validated with a mixture of eight natural product standards. Ultraviolet and evaporative light scattering detections were used in parallel for a comprehensive monitoring. In addition, post-chromatographic mass spectrometry detection was provided by high-throughput ultrahigh-performance liquid chromatography time-of-flight mass spectrometry analyses of all fractions. The processing of all liquid chromatography-mass spectrometry data in the form of an medium-performance liquid chromatography x ultra high-performance liquid chromatography time-of-flight mass spectrometry matrix enabled an efficient localisation of the compounds of interest in the generated fractions. The methodology was successfully applied for the separation of three different plant extracts that contain many diverse secondary metabolites. The advantages and limitations of this approach and the theoretical chromatographic background that rules such as liquid chromatography gradient transfer are presented from a practical viewpoint.

journal_name

Planta Med

journal_title

Planta medica

authors

Challal S,Queiroz EF,Debrus B,Kloeti W,Guillarme D,Gupta MP,Wolfender JL

doi

10.1055/s-0035-1545912

subject

Has Abstract

pub_date

2015-11-01 00:00:00

pages

1636-43

issue

17

eissn

0032-0943

issn

1439-0221

journal_volume

81

pub_type

杂志文章
  • Bioactive compounds from the buds of Platanus orientalis and isolation of a new kaempferol glycoside.

    abstract::A new compound kaempferol 3-O-alpha-L-(2"-E-p-coumaroyl)-rhamnopyranoside, as well as the known flavonoids, kaempferol 3-O-beta-D-(6"-E-p-coumaroyl)-glucopyranoside, kaempferol 3-O-alpha-L-(2",3"-di-E-p-coumaroyl)-rhamnopyranoside, and caffeic acid were obtained from the methanolic extract of Platanus orientalis L. bu...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-959751

    authors: Mitrokotsa D,Mitaku S,Demetzos C,Harvala C,Mentis A,Perez S,Kokkinopoulos D

    更新日期:1993-12-01 00:00:00

  • Geraniol dehydrogenase: a determinant of essential oil quality in lemongrass1.

    abstract::Geraniol dehydrogenase, the specific enzyme involved in geraniol to citral TRANS (geranial) transformation, activity was monitored in various lemongrass cultivars differing in amounts and relative percentages of citral and geraniol in their essential oils. The enzyme activity had a positive and significant association...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-959636

    authors: Singh-Sangwan N,Sangwan RS,Luthra R,Thakur RS

    更新日期:1993-04-01 00:00:00

  • Cryopreservation of Digitalis obscura selected genotypes by encapsulation-dehydration.

    abstract::Shoot-tips from several genotypes of the cardenolide-producing perennial shrub Digitalis obscura L. were successfully cryopreserved using the encapsulation-dehydration technique. Precultivation on MS medium containing 0.5 M sucrose, followed by 2.5 h dehydration (final weight 30 %) induced shoot regrowth in 42 % of cr...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2001-18861

    authors: Sales E,Nebauer SG,Arrillaga I,Segura J

    更新日期:2001-12-01 00:00:00

  • Novel experimental model using free radical-induced emesis for surveying anti-emetic compounds from natural sources.

    abstract::A novel experimental model of free radical-induced emesis for screening anti-emetic compounds from natural sources was established. 2,2'-Azobis(2-amidinopropane) dihydrochloride (AAPH) dissolved in liposome induced emesis in young chickens, and the emesis was prevented by antioxidants including N-(2-mercaptopropionyl)...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2006-960829

    authors: Yang Y,Kinoshita K,Koyama K,Takahashi K,Tai T,Nunoura Y,Watanabe K

    更新日期:1999-08-01 00:00:00

  • LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity.

    abstract::Targeted isolation based on a combination of NMR and HPLC-PDA-MS of a dichloromethane extract of Thymus vulgaris Varico 3 aerial parts afforded one new p-cymene dimer, 6,3',4'-trihydroxy-5,5'-diisopropyl-2,2'-dimethylbiphenyl (1: ), together with two known p-cymene derivatives (2: and 3: ), as well as five known compo...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/a-0927-7041

    authors: Stefanis I,Hadjipavlou-Litina D,Bilia AR,Karioti A

    更新日期:2019-08-01 00:00:00

  • Pyrrolizidine alkaloids from Eupatorium portoricense.

    abstract::Three pyrrolizidine alkaloids were isolated from Eupatorium portoricense and their structures elucidated by spectroscopic methods as (-)-viridifloryl-supinidine (amabiline), (-)-viridifloryl-heliotridine (echinatine), and C12- O-acetyl-(-)-viridifloryl-heliotridine (O(12)-acetylechinatine). ...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2006-958112

    authors: Wiedenfeld H,Guerrero R,Roeder E

    更新日期:1995-08-01 00:00:00

  • Sarothrin from Alkanna orientalis is an antimicrobial agent and efflux pump inhibitor.

    abstract::An Alkanna orientalis leaf and flower extract inhibited the growth of Staphylococcus aureus, a pathogen that causes an estimated 478 000 hospitalizations in the US annually. Bioassay-guided fractionation of A. orientalis resulted in isolation of the flavonoid sarothrin (5,7,4'-trihydroxy-3,6,8-trimethoxyflavone), whic...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0032-1328259

    authors: Bame JR,Graf TN,Junio HA,Bussey RO 3rd,Jarmusch SA,El-Elimat T,Falkinham JO 3rd,Oberlies NH,Cech RA,Cech NB

    更新日期:2013-03-01 00:00:00

  • Two new 8-oxotetrahydroprotoberberine alkaloids, gusanlung A and B, from Acangelisia gusanlung.

    abstract::Two new 8-oxotetrahydroprotoberberine alkaloids, gusanlung A(1) and B(2), together with known isoquinoline alkaloids, berberine and jatrorrhizine, were isolated from the Chinese medicinal plant Acangelisia gusanlung H. S. Lo (Menispermaceae). Their structures were elucidated mainly by spectroscopic analysis. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-960150

    authors: Zhang JS,Chen ZL

    更新日期:1991-10-01 00:00:00

  • Stimulation of Indole Alkaloid Production in Cell Suspension Cultures of Catharanthus roseus by Abscisic Acid.

    abstract::When added to suspension cultures of CATHARANTHUS ROSEUS, abscisic acid (ABA) stimulated intracellular accumulation of the indole alkaloids catharanthine and ajmalicine in both flask and 30 litre fermenter-scale systems. The response varied, and depended upon the cell line, the concentration and source of the ABA, and...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-962775

    authors: Smith JI,Smart NJ,Kurz WG,Misawa M

    更新日期:1987-10-01 00:00:00

  • Modulation of apoptosis by natural products for cancer therapy.

    abstract::Natural products can exhibit many beneficial effects on human health. As far as cancer is concerned, naturally occurring compounds have been reported to prevent tumorigenesis and also to suppress the growth of established tumors. As cancer cells have evolved multiple mechanisms to resist the induction of programmed ce...

    journal_title:Planta medica

    pub_type: 杂志文章,评审

    doi:10.1055/s-0030-1249961

    authors: Fulda S

    更新日期:2010-08-01 00:00:00

  • Intestinal immune system modulating polysaccharides from rhizomes of Atractylodes lancea.

    abstract::Hot water extract (ALR-0) of rhizomes of Atractylodes lanceo DC. was fractionated into MeOH-soluble fraction (ALR-1), supernatant fraction of EtOH precipitation (ALR-3 + 4), and crude polysaccharide fraction (ALR-5). Among these fractions, only ALR-5 showed potent stimulating activity for proliferation of bone marrow ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957564

    authors: Yu KW,Kiyohara H,Matsumoto T,Yang HC,Yamada H

    更新日期:1998-12-01 00:00:00

  • Bisbenzylisoquinoline alkaloids from the roots of cyclea tonkinensis.

    abstract::Cissampentine A (1), an enantiomer of cissampentin, three new cycleatjehenine-type bisbenzylisoquinoline alkaloids, cissampentine B-D (2-4), and five known alkaloids were isolated from the roots of Cyclea tonkinensis. Their structures were established by interpretation of NMR, high-resolution ESI-MS data, and CD spect...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0035-1545882

    authors: Wang JZ,Liao J,Xu WL,Chen XB

    更新日期:2015-05-01 00:00:00

  • New oxypregnane glycosides from Caralluma penicillata.

    abstract::The ether fraction of the defatted ethanol extract of the aerial parts of Caralluma penicillata (defl) M. E. Br. (Asclepiadaceae) yielded four new oxypregnane glycosides, penicillosides D-G. The structures of the isolated compounds were established by different spectroscopic methods. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2002-32078

    authors: Abdel-Sattar E,Meselhy MR,Al-Yahya MA

    更新日期:2002-05-01 00:00:00

  • Assessment of the anti-HIV activity of a pine cone isolate.

    abstract::Characterization of an alkali-soluble isolate from Pinus nigra Arnold (Pinaceae) seed cones by thioacidolysis revealed a significant phenylpropanoid (i.c. lignin) component which may provide the observed anti-HIV-1 activity for this substance. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957801

    authors: Eberhardt TL,Young RA

    更新日期:1996-02-01 00:00:00

  • Compounds from Arnebia euchroma and their related anti-HCV and antibacterial activities.

    abstract::Three new hydroquinone terpenoids with benzogeijerene skeletons, euchroquinols A-C (1- 3), and a new monoterpenylbenzenoid, 9,17-epoxyarnebinol (4), along with five known compounds were isolated from the stem bark of ARNEBIA EUCHROMA. Shikonin (6) exhibited potent anti-HCV activity with a selective index of 43.56, and...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0031-1280266

    authors: Li HM,Tang YL,Zhang ZH,Liu CJ,Li HZ,Li RT,Xia XS

    更新日期:2012-01-01 00:00:00

  • Interactions of viscotoxins with vesicles of genuine plant membranes.

    abstract::Extracts of Viscum album L. produced by a specific homogenization procedure contain viscotoxins (VT) and liposome-like membrane vesicles, formed from cellular membranes. Interactions between these membrane structures and viscotoxins are characterized in this work. Binding properties of viscotoxins with mistletoe extra...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2008-1034282

    authors: Winkler K,Jäger S,Leneweit G,Schubert R

    更新日期:2008-02-01 00:00:00

  • LC-MS-Based Quality Assessment of a Traditional Chinese Medicine YANG XIN Formulation.

    abstract::YANG XIN is a traditional Chinese medicine formulation used for nervous fatigue and consists of a proprietary blend of concentrated extracts from 18 plant ingredients. The 18 constituent plant ingredients, YANG XIN capsules, and formulations 2014-005_1 A and 1B were extracted by consecutive 24-hour macerations with di...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0042-106170

    authors: Almalki AJ,Zaher A,Simithy J,Keller WJ,Tripp M,Calderón AI

    更新日期:2016-08-01 00:00:00

  • Plants: a source for new antimycobacterial drugs.

    abstract::Tuberculosis, also called TB, is currently a major health hazard due to multidrug-resistant forms of bacilli. Global efforts are underway to eradicate TB using new drugs with new modes of action, higher activity, and fewer side effects in combination with vaccines. For this reason, unexplored new sources and previousl...

    journal_title:Planta medica

    pub_type: 杂志文章,评审

    doi:10.1055/s-0033-1350978

    authors: Santhosh RS,Suriyanarayanan B

    更新日期:2014-01-01 00:00:00

  • Antimalarial compounds containing an alpha,beta-unsaturated carbonyl moiety from Tanzanian medicinal plants.

    abstract::Pure compounds were isolated from plant extracts with antimalarial activity. The extracts were obtained from the tubers of Cyperus rotundus L. (Cyperaceae), the rootbark of Zanthoxylum gilletii (De Wild) Waterm. (Rutaceae), and the rootbark of Margaritaria discoidea (Baill.) Webster (Euphorbiaceae). The most active co...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-960985

    authors: Weenen H,Nkunya MH,Bray DH,Mwasumbi LB,Kinabo LS,Kilimali VA,Wijnberg JB

    更新日期:1990-08-01 00:00:00

  • A New Linalool Derivative and Other Constituents from Piper ribesoides.

    abstract::Extraction of PIPER RIBESOIDES Wall, furnished the new linalool derivative (+)-3,7-dimethyl-3-hydroxy-4-( P-coumaryloxy)-1,6-octadiene, the lignans (-)-hinokinin and (-)-cubebin, N-isobutyl-2 E,4 E-deca-2,4-dienamide, methyl piperate, methyl 2 E,4 E,6 E-7-phenyl-2,4,6-heptatrienoate, palmitic acid, stearic acid, and b...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-961923

    authors: Kijjoa A,Pinto MM,Tantisewie B,Herz W

    更新日期:1989-04-01 00:00:00

  • Inhibition of HIV-1 reverse transcriptase and HIV-1 replication by Calophyllum coumarins and xanthones.

    abstract::As part of our continuing study on the Calophyllum species, a number of coumarins, xanthones and chromene acids from different Calophyllum species of Sri Lanka were tested for inhibitory activity against the HIV-1 and its virally-encoded reverse transcriptase (RT). These compounds were found to be inactive in both the...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2002-20058

    authors: Dharmaratne HR,Tan GT,Marasinghe GP,Pezzuto JM

    更新日期:2002-01-01 00:00:00

  • Three new xanthones from the resin of Garcinia hanburyi.

    abstract::Three new xanthones, 22,23-dihydroxydihydrogambogenic acid (1), 12-hydroxygambogefic acid A (2), and hanburixanthone (3), along with thirteen known compounds were isolated from the resin of Garcinia hanburyi. The structures of the new compounds were determined by detailed analysis of 1D and 2D NMR spectra and by compa...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0032-1328537

    authors: Deng YX,Guo T,Shao ZY,Xie H,Pan SL

    更新日期:2013-06-01 00:00:00

  • New Pseudoguaianolides from Ambrosia maritima.

    abstract::The investigation of the aerial parts of two collections of AMBROSIA MARITIMA afforded in addition to known pseudoguaianolides nine new ones including two nor-sesquiterpene lactones and two dimeric lactones. The structures were elucidated by highfield (1)H-NMR spectroscopy. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-962617

    authors: Jakupovic J,Sun H,Geerts S,Bohlmann F

    更新日期:1987-02-01 00:00:00

  • Proteome analysis reveals a distinct molecular profile of cellular stress following incubation of DDT1-MF2 smooth muscle cells in the presence of a high concentration of hyperforin.

    abstract::The acylphloroglucinol derivative hyperforin is a major constituent of St. John's wort extracts ( Hypericum perforatum L.), which has been demonstrated to contribute to the antidepressant action of this herbal drug. In previous investigations we observed that hyperforin causes a rapid stimulation of intracellular calc...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2004-818946

    authors: Schrattenholz A,Schroer K,Chatterjee SS,Koch E

    更新日期:2004-04-01 00:00:00

  • Chemical composition, acute toxicity, and antinociceptive activity of the essential oil of a plant breeding cultivar of basil (Ocimum basilicum L.).

    abstract::Ocimum basilicum L. is an aromatic herb used in Brazil to treat illnesses such as respiratory and rheumatic problems, vomiting, and pain. In the present study, the chemical composition, acute toxicity, and antinociceptive effects of the essential oil (EO) of the cultivar "Maria Bonita" obtained from O. basilicum L. PI...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0030-1250607

    authors: Venâncio AM,Onofre AS,Lira AF,Alves PB,Blank AF,Antoniolli AR,Marchioro M,Estevam Cdos S,de Araujo BS

    更新日期:2011-05-01 00:00:00

  • Antimicrobial activity of polyacetylenes from Bellis perennis and their synthetic derivatives.

    abstract::The chemical investigation of the essential oils from the aerial organs of Bellis perennis L., the common daisy, showed that polyacetylenes were one of the dominant class of compounds. The major constituents, methyl deca-4,6-diynoate and deca-4,6-diynoic acid, and their structural analogues, deca-4,6-diyne, dimethyl o...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957751

    authors: Avato P,Vitali C,Mongelli P,Tava A

    更新日期:1997-12-01 00:00:00

  • Flavonol glycosides from Calendula officinalis flowers.

    abstract::Seven flavonol 3- O-glycosides were isolated from the flowers of CALENDULA OFFICINALIS L. Their structures were elucidated as isorhamnetin 3- O-glucoside, rutinoside, neohesperidoside, 2 (G)-rhamnosylrutinoside, quercetin glucoside, neohesperidoside, and 2 (G)-rhamnosylrutinoside by paper and thin layer chromatography...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-961831

    authors: Vidal-Ollivier E,Elias R,Faure F,Babadjamian A,Crespin F,Balansard G,Boudon G

    更新日期:1989-02-01 00:00:00

  • Further beta-Cyperone Derivatives from Haplopappus freemontii.

    abstract::The roots of HAPLOPAPPUS FREEMONTII afforded in addition to the known 8-oxo-beta-cyperone two further derivatives. The structures were elucidated by highfield (1)H-NMR spectroscopy. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-969205

    authors: Jakupovic J,Boeker R,King RM

    更新日期:1986-10-01 00:00:00

  • Prevention of galactosamine-induced hepatic damage by picroliv: study on bile flow and isolated hepatocytes (ex vivo).

    abstract::Picroliv, a standardized extract from the plant Picrorhiza kurrooa containing active constituents, showed a significant dose dependent (3-12 mg/kg p.o. x 7) protective activity against galactosamine-induced hepatic damage in rat as evaluated on the isolated hepatocytes (ex vivo) preparation. It markedly increased the ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-959600

    authors: Visen PK,Shukla B,Patnaik GK,Dhawan BN

    更新日期:1993-02-01 00:00:00

  • The structure and the stereochemistry of atractyliretin.

    abstract::The nor-kaurane diterpene Atractyliretin was obtained by acid hydrolysis of Atractyloside, a toxic substance isolated from ATRACTYLIS GUMMIFERA L (Compositae). On the basis of spectral (IR, (1)H-NMR, (13)C-NMR and MS) analysis and chemical degradation its structure and stereochemistry was identified as 4. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-969185

    authors: Camarda L,Ceraulo L,Ferrugia M,Pascual C,Sprio V

    更新日期:1986-10-01 00:00:00