Accelerated dereplication of crude extracts using HPLC-PDA-MS-SPE-NMR: quinolinone alkaloids of Haplophyllum acutifolium.

Abstract:

:Direct hyphenation of analytical-scale high-performance liquid chromatography, photo-diode array detection, mass spectrometry, solid-phase extraction and nuclear magnetic resonance spectroscopy (HPLC-PDA-MS-SPE-NMR) has been used for accelerated dereplication of crude extract of Haplophyllum acutifolium (syn. Haplophyllum perforatum). This technique allowed fast on-line identification of six quinolinone alkaloids, named haplacutine A-F, as well as of acutine, haplamine, eudesmine, and 2-nonylquinolin-4(1H)-one. Acutine and haplacutine E, isolated by preparative-scale HPLC, showed moderate antiplasmodial activity with IC(50) values of 2.17+/-0.22 microM and 3.79+/-0.24 microM, respectively (chloroquine-sensitive Plasmodium falciparum 3D7 strain).

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Staerk D,Kesting JR,Sairafianpour M,Witt M,Asili J,Emami SA,Jaroszewski JW

doi

10.1016/j.phytochem.2009.05.004

subject

Has Abstract

pub_date

2009-05-01 00:00:00

pages

1055-61

issue

8

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(09)00199-X

journal_volume

70

pub_type

杂志文章
  • Phytochemistry and pharmacology of the genus Leonurus: The herb to benefit the mothers and more.

    abstract::Plants belonging to the genus Leonurus, also named motherwort, are traditionally used for anti-gynecological disorder in East Asia, and for sedative in Europe. Chemical investigation of the genus Leonurus not only enriched the natural products library, but also enlarged the pharmacological application of this traditio...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2017.12.016

    authors: Zhang RH,Liu ZK,Yang DS,Zhang XJ,Sun HD,Xiao WL

    更新日期:2018-03-01 00:00:00

  • Cyanogenic and non-cyanogenic glycosides from Manihot esculenta.

    abstract::In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)-2-met hylbutanenitrile , two novel non-cyanogenic glycosides, (2S)-((6-O-(beta-D-apiofuranosyl)-beta-D- glucopyranosyl)oxy)butane and 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00398-q

    authors: Prawat H,Mahidol C,Ruchirawat S,Prawat U,Tuntiwachwut-tikul P,Tooptakong U,Taylor WC,Pakawatchai C,Skeleton BW,White AH

    更新日期:1995-11-01 00:00:00

  • Terpenoids in transformed root culture of Tripterygium wilfordii.

    abstract::Investigation of a hairy root culture of Tripterygium wilfordii var. regelii transformed with Agrobacterium rhizogenes resulted in the isolation of new diterpenoid and sesquiterpenoid together with known triterpenoids. These structures were determined by spectroscopic analyses. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00300-8

    authors: Nakano K,Yoshida C,Furukawa W,Takaishi Y,Shishido K

    更新日期:1998-11-20 00:00:00

  • Hydroperoxide lyase cascade in pea seedlings: Non-volatile oxylipins and their age and stress dependent alterations.

    abstract::The profiles of non-volatile oxylipins of pea (Pisum sativum) seedlings were examined by gas chromatography-mass spectrometry after invitro incubation with α-linolenic acid. The 13-lipoxygenase/hydroperoxide lyase (HPL) products were predominant in the leaves, while the roots possess both 13- and 9-HPL products. Allen...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.01.013

    authors: Mukhtarova LS,Mukhitova FK,Gogolev YV,Grechkin AN

    更新日期:2011-04-01 00:00:00

  • Dammarane-type saponins from Gynostemma pentaphyllum.

    abstract::Seven dammarane glycosides, gypenosides GC1 to GC7, together with ten known compounds, gypenosides V, XIV, XLII-XLVI, gynosaponins TN-1, -2, and gymnemaside VI, were isolated from the methanol extract of the aerial parts of Gynostemma pentaphyllum. Their structures were elucidated by both analysis of 1D and 2D NMR spe...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.04.003

    authors: Kim JH,Han YN

    更新日期:2011-08-01 00:00:00

  • Ester-type cephalotaxus alkaloids from Cephalotaxus harringtonia var. drupacea.

    abstract::Three alkaloids, neoharringtonine, homoneoharringtonine and 3'S-hydroxyneoharringtonine, were isolated from the leaves and stems of Cephalotaxus harringtonia var. drupacea. Their structures were established by spectroscopic methods, including two-dimensional NMR and CD spectra, and their antileukaemic activity was eva...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(96)00574-2

    authors: Takano I,Yasuda I,Nishijima M,Yanagi Y,Takeya K,Itokawa H

    更新日期:1997-02-01 00:00:00

  • Caffeic glycoside esters from Jasminum nudiflorum and some related species.

    abstract::Poliumoside, forsythoside B, echinacoside and arenarioside, caffeic glycoside esters, were isolated from several species of Oleaceae. The poliumoside/forsythoside ratio distinguishes Jasminum nudiflorum from J. mesnyi. Arenarioside and forsythoside B act in Forsythia species as good hybridization markers. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)80032-a

    authors: Andary C,Tahrouch S,Marion C,Wylde R,Heitz A

    更新日期:1992-03-01 00:00:00

  • Phytochemistry and medicinal plants.

    abstract::A truncated history of the contribution of plants to medicine is given with reference to some of the less well known ancestors of the Harborne family. Six of the top 20 prescriptions dispensed in 1996 were natural products and the clinical use of drugs such as artemisinin, etoposide and taxol has once more focussed at...

    journal_title:Phytochemistry

    pub_type: 历史文章,杂志文章

    doi:10.1016/s0031-9422(00)00456-8

    authors: Phillipson JD

    更新日期:2001-02-01 00:00:00

  • Sinapoyltransferases in the light of molecular evolution.

    abstract::Acylation is a prevalent chemical modification that to a significant extent accounts for the tremendous diversity of plant metabolites. To catalyze acyl transfer reactions, higher plants have evolved acyltransferases that accept beta-acetal esters, typically 1-O-glucose esters, as an alternative to the ubiquitously oc...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.07.023

    authors: Stehle F,Brandt W,Stubbs MT,Milkowski C,Strack D

    更新日期:2009-10-01 00:00:00

  • Application of MS and NMR to the structure elucidation of complex sugar moieties of natural products: exemplified by the steroidal saponin from Yucca filamentosa L.

    abstract::An approach, using well characterized procedures, is presented that should be of general applicability for the structural elucidation of complex sugar moieties of natural products. The methods used are exemplified by the structure elucidation of a new gitogenin-based steroidal saponin that has a strong leishmanicidal ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00035-8

    authors: Plock A,Beyer G,Hiller K,Gründemann E,Krause E,Nimtz M,Wray V

    更新日期:2001-06-01 00:00:00

  • A triterpenoid saponin from Phytolacca esculenta.

    abstract::A new triterpenoid saponin, 3-O-[beta-D-glucopyranosyl(1----4)-beta-D- xylopyranosyl]-28-O-beta-D-glucopyranosyl-30-methyloleanate-9(11), 12-dien- 2,3,23-trihydroxyl-28-oic acid, was isolated from the roots of Phytolacca esculenta. The structure was assigned by chemical methods and spectral analysis (1H, 13C, DEPT NMR...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)83327-u

    authors: Yi YH

    更新日期:1992-07-01 00:00:00

  • PTP1B inhibitory and cytotoxic C-24 epimers of Δ28-24-hydroxy stigmastane-type steroids from the brown alga Dictyopteris undulata Holmes.

    abstract::Ten stigmastane-type steroids bearing unusual Δ28-24-hydroxy side chains, dictyopterisins A-J, including three pairs of C-24 epimers, dictyopterisins B/C, F/G, and I/J, were isolated from the brown alga Dictyopteris undulata Holmes, together with two previously reported analogues, (24S)- and (24R)-saringosterol. Their...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.11.013

    authors: Feng MT,Wang T,Liu AH,Li J,Yao LG,Wang B,Guo YW,Mao SC

    更新日期:2018-02-01 00:00:00

  • Two oleanene glycosides from the aerial parts of Caltha polypetala.

    abstract::Two new oleanene glycosides (1-2) possessing hederagenin as the aglycone were isolated from the methanolic extract of the aerial parts of Caltha polypetala together with four known glycosides. The saccharide portion linked to C-3 of the aglycone is made up of alpha-L-arabinopyranose, alpha-L-rhamnopyranose and galacto...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00164-8

    authors: Baykal T,Bedir E,Calis I,Aquino R,Piacente S,Pizza C

    更新日期:1999-08-01 00:00:00

  • Xanthones from Hypericum roeperanum.

    abstract::Four new xanthones have been isolated from the roots of Hypericum roeperanum. Their structures have been established by a combination of spectroscopic and chemical methods as 1,6-dihydroxy-5-methoxy-4',5'-dihydro-4',4',5'-trimethylfurano- (2',3':3,4)-xanthone (5-O-methyl-2-deprenylrheediaxanthone B), 1,6-dihydroxy-5-m...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(96)00284-1

    authors: Rath G,Potterat O,Mavi S,Hostettmann K

    更新日期:1996-09-01 00:00:00

  • Three phenylethanoid glycosides and an iridoid glycoside from Picrorhiza scrophulariiflora.

    abstract::Three new phenylethanoid glycoside, named scrosides A-C and a new iridoid glycosides, named picroside IV, have been isolated from the underground parts of Picrorhiza scrophulariiflora, together with 11 known compounds. Their structures were elucidated by the means of 2D NMR spectroscopy and chemical methods. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00030-2

    authors: Li JX,Li P,Tezuka Y,Namba T,Kadota S

    更新日期:1998-06-01 00:00:00

  • Cytotoxic xanthones from the roots of Mesua ferrea L.

    abstract::Five undescribed xanthones, 4-methoxypyranojacareubin, 4-hydroxy-3-prenylpyranoxanthone, 1-hydroxy-5,7-dimethoxyxanthone, 5-hydroxy-1,6,7-trimethoxyxanthone and 2-hydroxy-1,5-dimethoxyxanthone, together with thirty-three known xanthones were isolated from the roots of Mesua ferrea L. The structures of all isolated xan...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.10.008

    authors: Chukaew A,Saithong S,Chusri S,Limsuwan S,Watanapokasin R,Voravuthikunchai SP,Chakthong S

    更新日期:2019-01-01 00:00:00

  • Ginsenosides from American ginseng: chemical and pharmacological diversity.

    abstract::Ginseng occupies a prominent position in the list of best-selling natural products in the world. Compared to the long history of use and widespread research on Asian ginseng, the study of American ginseng is relatively limited. In the past decade, some promising advances have been achieved in understanding the chemist...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2011.02.012

    authors: Qi LW,Wang CZ,Yuan CS

    更新日期:2011-06-01 00:00:00

  • A galloylated cyanogenic glycoside from the Australian endemic rainforest tree Elaeocarpus sericopetalus (Elaeocarpaceae).

    abstract::A cyanogenic glycoside - 6'-O-galloylsambunigrin - has been isolated from the foliage of the Australian tropical rainforest tree species Elaeocarpus sericopetalus F. Muell. (Elaeocarpaceae). This is the first formal characterisation of a cyanogenic constituent in the Elaeocarpaceae family, and only the second in the o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.03.022

    authors: Miller RE,Stewart M,Capon RJ,Woodrow IE

    更新日期:2006-07-01 00:00:00

  • Detection of tomatinase from Fusarium oxysporum f. sp. lycopersici in infected tomato plants.

    abstract::The antifungal glycoalkaloid alpha-tomatine of the tomato plant (Lycopersicon esculentum) is proposed to protect the plant against phytopathogenic fungi. Fusarium oxysporum f. sp. lycopersici, a vascular pathogen of tomato, produces a tomatinase enzyme which hydrolyses the glycoalkaloid into non-fungitoxic compounds. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00170-2

    authors: Lairini K,Ruiz-Rubio M

    更新日期:1997-08-01 00:00:00

  • Sesquiterpene lactones of Centaurea scoparia.

    abstract::From the ethanolic extract of the aerial parts of Centaurea scoparia four new sesquiterpene lactones, belonging to the guaiane class, were isolated and identified, together with a known germacranolide. The structures were elucidated by spectroscopic methods including one- and two-dimensional NMR studies. The relative ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00257-x

    authors: Youssef DT

    更新日期:1998-11-20 00:00:00

  • Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity.

    abstract::The dichloromethane extract of the stem bark of Warburgia ugandensis afforded three new coloratane sesquiterpenes, namely: 6alpha,9alpha-dihydroxy-4(13),7-coloratadien-11,12-dial (1), 4(13),7-coloratadien-12,11-olide (2), and 7beta-hydroxy-4(13),8-coloratadien-11,12-olide (3), together with nine known sesquiterpenes, ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.07.018

    authors: Wube AA,Bucar F,Gibbons S,Asres K

    更新日期:2005-10-01 00:00:00

  • Steroidal glycosides from the bulbs of Bessera elegans and their cytotoxic activities.

    abstract::Examination of the bulbs of Bessera elegans (Liliaceae) led to isolation of nine new and five known steroidal glycosides. The structures of the nine compounds were determined based on the results of spectroscopic analysis, including two-dimensional NMR, and hydrolysis followed by chromatographic and spectroscopic anal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.09.023

    authors: Matsuo Y,Akagi N,Hashimoto C,Tachikawa F,Mimaki Y

    更新日期:2013-12-01 00:00:00

  • Biosynthesis of 20-hydroxyecdysone in plants: 3β-hydroxy-5β-cholestan-6-one as an intermediate immediately after cholesterol in Ajuga hairy roots.

    abstract::3β-Hydroxy-5β-cholestan-6-one was identified in the EtOAc extract of Ajuga hairy roots by micro-analysis using LC-MS/MS in the multiple reaction mode (MRM). Furthermore, administration of (2,2,4,4,7,7-(2)H6)- and (2,2,4,4,6,7,7-(2)H7)-cholesterols to the hairy roots followed by LC-MS/MS analysis of the EtOAc extract o...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.12.019

    authors: Fujimoto Y,Maeda I,Ohyama K,Hikiba J,Kataoka H

    更新日期:2015-03-01 00:00:00

  • Probing the transcriptome of Aconitum carmichaelii reveals the candidate genes associated with the biosynthesis of the toxic aconitine-type C19-diterpenoid alkaloids.

    abstract::Aconitum carmichaelii has long been used as a traditional Chinese medicine, and its processed lateral roots are known commonly as fuzi. Aconitine-type C19-diterpenoid alkaloids accumulating in the lateral roots are some of the main toxicants of this species, yet their biosynthesis remains largely unresolved. As a firs...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.04.022

    authors: Zhao D,Shen Y,Shi Y,Shi X,Qiao Q,Zi S,Zhao E,Yu D,Kennelly EJ

    更新日期:2018-08-01 00:00:00

  • Phytochemistry and pharmacognosy.

    abstract::During the past 50 years there have been tremendous advances in chemical and biological techniques of analysis that have transformed research in pharmacognosy. The PSE has regularly held symposia of relevance to pharmacognosy and some of these are briefly reviewed in the area of natural products from higher plants. Th...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2007.06.028

    authors: Phillipson JD

    更新日期:2007-11-01 00:00:00

  • Sesquiterpenoid glycosides from glandular trichomes of the wild tomato relative Solanum habrochaites.

    abstract::Profiles of terpenoid glycoside metabolites in glandular trichomes of Solanum habrochaites LA1777 leaves were generated using ultrahigh performance liquid chromatography/time-of-flight mass spectrometry with multiplexing of non-selective collision-induced dissociation (CID). Profiling data suggested a diverse group of...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.11.011

    authors: Ekanayaka EA,Li C,Jones AD

    更新日期:2014-02-01 00:00:00

  • Reassessment of effects on lignification and vascular development in the irx4 Arabidopsis mutant.

    abstract::The Arabidopsis thaliana irregular xylem4 (irx4) cinnamoyl-CoA reductase 1 (CCR1) mutant was reassessed for its purported exclusive rate-limiting or key effects on lignification. Analyses of gross growth characteristics and stem cross-section anatomy, from seedling emergence to senescence, revealed that stunted irx4 m...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.12.016

    authors: Patten AM,Cardenas CL,Cochrane FC,Laskar DD,Bedgar DL,Davin LB,Lewis NG

    更新日期:2005-09-01 00:00:00

  • Comparative analysis of CYP93E proteins for improved microbial synthesis of plant triterpenoids.

    abstract::Cytochrome P450-dependent monooxygenases (P450s) belonging to the CYP93E subfamily catalyze the C-24 oxidation of the triterpene backbone during the biosynthesis of triterpenoid saponins, which are bioactive plant natural products. In our attempts to produce plant triterpenoids in the yeast Saccharomyces cerevisiae, w...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.10.002

    authors: Moses T,Thevelein JM,Goossens A,Pollier J

    更新日期:2014-12-01 00:00:00

  • Identification and heritability of fumonisin insensitivity in Zea mays.

    abstract::Landraces of maize (Zea mays ssp. mays) and its wild teosinte relatives (Zea mays spp. parviglumis and mexicana) were surveyed for sensitivity to fumonisin B(1), a phytotoxin produced by the maize pathogen Gibberella moniliformis. Only two of 42 Z. mays samples were highly insensitive to FB(1) (ED(50) = ca. 200 microM...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.08.013

    authors: Desjardins AE,Plattner RD,Stessman RJ,McCormick SP,Millard MJ

    更新日期:2005-10-01 00:00:00

  • Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry.

    abstract::A method is described for the enrichment of odd very-long-chain polyunsaturated fatty acids (VLCPUFAs) by means of RP-HPLC and argentation TLC from total fatty acids of the dinoflagellate A. carterae and their identification as picolinyl esters by means of microbore liquid chromatography-mass spectrometry with atmosph...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.08.021

    authors: Rezanka T,Nedbalová L,Sigler K

    更新日期:2008-11-01 00:00:00