The configuration of methyl jasmonate affects paclitaxel and baccatin III production in Taxus cells.

Abstract:

:All stereoisomers of methyl jasmonate (MJA) were prepared, and their effects on cell yield and promotion of paclitaxel (Taxol) and baccatin III production investigated in cell suspension cultures of Taxus media. (3R,7S)-MJA showed the strongest cell growth inhibition, followed by (3R,7R)-MJA. In contrast, (3S,7R)- and (3S,7S)-MJA had very low inhibitory effects, indicating that this inhibition depends largely on the (3R)-configuration. In terms of the promotion of paclitaxel and baccatin III production, (3R,7R)-MJA had the highest activity. Although it showed considerable activity at low concentration, at higher concentrations the activity was decreased due to strong inhibition of cell growth. Interestingly, paclitaxel and baccatin III contents increased even at a high (3S,7R)-MJA concentration, whereas the other isomers had the opposite effects. These findings are interpreted to suggest that the optimum configuration is (3R,7R), the (3R)-configuration not being indispensable, and that the (7R)-configuration is suitable for the promotion of paclitaxel and baccatin III production.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Yukimune Y,Hara Y,Nomura E,Seto H,Yoshida S

doi

10.1016/s0031-9422(00)00006-6

subject

Has Abstract

pub_date

2000-05-01 00:00:00

pages

13-7

issue

1

eissn

0031-9422

issn

1873-3700

pii

S0031942200000066

journal_volume

54

pub_type

杂志文章
  • Annosenegalin and annogalene: two cytotoxic mono-tetrahydrofuran acetogenins from Annona senegalensis and Annona cherimolia.

    abstract::Two new cytotoxic mono-tetrahydrofuran acetongenins, annosenegalin and annogalene, have been isolated from the cytotoxic methanolic extract of Annona senegalensis and A. cherimolia seeds. Their structures were established on the basis of 1D and 2D NMR spectroscopic techniques. Annosenegalin belongs to the rare type of...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00891-8

    authors: Sahpaz S,González MC,Hocquemiller R,Zafra-Polo MC,Cortes D

    更新日期:1996-05-01 00:00:00

  • Microbial oligosaccharides differentially induce volatiles and signalling components in Medicago truncatula.

    abstract::Plants perceive biotic stimuli by recognising a multitude of different signalling compounds originating from the interacting organisms. Some of these substances represent pathogen-associated molecular patterns, which act as general elicitors of defence reactions. But also beneficial microorganisms like rhizobia take a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.04.019

    authors: Leitner M,Kaiser R,Rasmussen MO,Driguez H,Boland W,Mithöfer A

    更新日期:2008-07-01 00:00:00

  • Abscisic acid-induced modulation of metabolic and redox control pathways in Arabidopsis thaliana.

    abstract::Abscisic acid (ABA) has been implicated as a mediator in plant responses to various environmental stresses. To evaluate the transcriptional and metabolic events downstream of ABA perception, Arabidopsis thaliana seedlings were analyzed by transcript and metabolite profiling, and results were integrated, using the rece...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.09.020

    authors: Ghassemian M,Lutes J,Chang HS,Lange I,Chen W,Zhu T,Wang X,Lange BM

    更新日期:2008-12-01 00:00:00

  • Characterization of native and yeast-expressed tomato fruit fructokinase enzymes.

    abstract::Three fructokinase isozymes (FKI, FKII, FKIII) were separated from both immature and ripe tomato fruit pericarp. All three isozymes were specific for fructose with undetectable activity towards glucose or mannose. The three isozymes could be distinguished from one another with respect to response to fructose, Mg and n...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00331-4

    authors: Petreikov M,Dai N,Granot D,Schaffer AA

    更新日期:2001-11-01 00:00:00

  • Polyketide derivatives from a marine-sponge-associated fungus Pestalotiopsis heterocornis.

    abstract::Twelve previously undescribed polyketide derivatives, heterocornols A-L, and seven known analogues were isolated from a culture of the fungus Pestalotiopsis heterocornis associated with sponge. Their structures were elucidated by a comprehensive spectroscopic data analysis and CD Cotton effects. These compounds were e...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.06.009

    authors: Lei H,Lin X,Han L,Ma J,Dong K,Wang X,Zhong J,Mu Y,Liu Y,Huang X

    更新日期:2017-10-01 00:00:00

  • Isoflavones and anti-inflammatory constituents from the fruits of Psoralea corylifolia.

    abstract::The fruits of Psoralea corylifolia, known as Psoraleae Fructus (Buguzhi in Chinese), are traditionally used for the treatment of spermatorrhea, nephritis, asthma, pollakiuria, and various inflammatory diseases. Three previously undescribed isoflavone derivatives, 7-O-methylcorylifol A, 7-O-isoprenylcorylifol A, and 7-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.08.004

    authors: Chen CH,Hwang TL,Chen LC,Chang TH,Wei CS,Chen JJ

    更新日期:2017-11-01 00:00:00

  • Procyanidin xylosides from the bark of Betula pendula.

    abstract::A procyanidin dimer xyloside, catechin-(4α→8)-7-O-β-xylopyranosyl-catechin, was isolated from the inner bark of Betula pendula and its structure was determined using 1D and 2D NMR, CD and high-resolution ESIMS. Interestingly, the 7-O-β-xylopyranose unit was found to be present in the lower terminal unit of the dimer. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.01.008

    authors: Liimatainen J,Karonen M,Sinkkonen J

    更新日期:2012-04-01 00:00:00

  • Response of prostaglandin content in the red alga Gracilaria verrucosa to season and solar irradiance.

    abstract::The influence of solar irradiance and seasons on prostaglandin (PG) and arachidonic acid (AA) content in the marine red alga Gracilaria verrucosa (Huds.) Papenf. (unattached form) was investigated. PGA(2), PGE(2), PGF(2), and 15-keto-PGE(2) were isolated from the alga, quantitatively analyzed as 4-methyl-7-methoxycoum...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00321-1

    authors: Imbs AB,Vologodskaya AV,Nevshupova NV,Khotimchenko SV,Titlyanov EA

    更新日期:2001-12-01 00:00:00

  • Cytotoxic benzil and coumestan derivatives from Tephrosia calophylla.

    abstract::A benzil, calophione A, 1-(6'-Hydroxy-1',3'-benzodioxol-5'-yl)-2-(6''-hydroxy-2''-isopropenyl-2'',3''-dihydro-benzofuran-5''-yl)-ethane-1,2-dione and three coumestan derivatives, tephcalostan B, C and D were isolated from the roots of Tephrosia calophylla. Their structures were deduced from spectroscopic data, includi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.10.009

    authors: Ganapaty S,Srilakshmi GV,Pannakal ST,Rahman H,Laatsch H,Brun R

    更新日期:2009-01-01 00:00:00

  • Production of (+)-5-deoxystrigol by Lotus japonicus root culture.

    abstract::Lotus japonicus roots, cultured in a modified B5 medium, produced and secreted germination stimulants that induced Striga hermonthica seed germination. The germination-inducing activity was detected both in the roots and the culture filtrate. Following bioassay-guided purification procedures, an active compound was is...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.06.011

    authors: Sugimoto Y,Ueyama T

    更新日期:2008-01-01 00:00:00

  • Malate. Jack of all trades or master of a few?

    abstract::The dicarboxylic acid malate has long been thought to play important roles in plant physiology. In addition to being a major photosynthate in C4 and CAM plants and an intermediate of the tricarboxylic acid cycle it has been proposed to play essential roles in pH regulation and important roles in pathogen response, as ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.04.023

    authors: Fernie AR,Martinoia E

    更新日期:2009-05-01 00:00:00

  • Three isoflavones from Derris scandens (Roxb.) Benth and their cancer chemopreventive activity and in vitro antiproliferative effects.

    abstract::Three undescribed isoflavones, derriscandenon A, B, and C, together with seven known isoflavones were isolated and structurally characterized during a study of the chemical constituents in the leaves of Derris scandens (Roxb.) Benth (Leguminosae, Fabaceae) collected in Bangladesh. The inhibitory activity of the compou...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112376

    authors: Ito C,Matsui T,Miyabe K,Hasan CM,Rashid MA,Tokuda H,Itoigawa M

    更新日期:2020-07-01 00:00:00

  • The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements.

    abstract::Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixture...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00266-1

    authors: Bülow N,Konig WA

    更新日期:2000-09-01 00:00:00

  • Protein phosphorylation in Nicotiana tabacum cells in response to perception of lipopolysaccharides from Burkholderia cepacia.

    abstract::Bacterial LPS have the ability to act as modulators of the innate immune response in plants. Complex and largely unresolved perception systems exist for LPS on the plant cell surfaces that lead to the activation of multiple intracellular defense signaling pathways. The aim of the present study was to investigate the p...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.09.005

    authors: Gerber IB,Dubery IA

    更新日期:2004-11-01 00:00:00

  • Characterization of an epoxide hydrolase from the Florida red tide dinoflagellate, Karenia brevis.

    abstract::Epoxide hydrolases (EH, EC 3.3.2.3) have been proposed to be key enzymes in the biosynthesis of polyether (PE) ladder compounds such as the brevetoxins which are produced by the dinoflagellate Karenia brevis. These enzymes have the potential to catalyze kinetically disfavored endo-tet cyclization reactions. Data minin...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.11.002

    authors: Sun P,Leeson C,Zhi X,Leng F,Pierce RH,Henry MS,Rein KS

    更新日期:2016-02-01 00:00:00

  • Phenylpropanoid glucosides from Chrozophora obliqua.

    abstract::From the aerial parts of Chrozophora obliqua, two phenylpropanoid glucosides: 4-O-methyl guaiacylglycerol 9-O-beta-glucopyranoside (1) and 4-O-methyl guaiacylglycerol 8-O-beta-glucopyranoside (2) together with syringin, benzyl alcohol glucoside, isorhamnetin-3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quer...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00262-x

    authors: Mohamed KM

    更新日期:2001-10-01 00:00:00

  • Mechanisms of survival of necrotrophic fungal plant pathogens in hosts expressing the hypersensitive response.

    abstract::The hypersensitive response (HR), elicited when resistant hosts are infected by incompatible races of biotrophic fungi, has been researched extensively. New studies on host responses to necrotrophic fungi are beginning to show that when the HR occurs in hosts colonized by necrotrophs, fungal growth is accelerated rath...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(01)00187-x

    authors: Mayer AM,Staples RC,Gil-ad NL

    更新日期:2001-09-01 00:00:00

  • Characterization of recombinant nitrile-specifier proteins (NSPs) of Arabidopsis thaliana: dependency on Fe(II) ions and the effect of glucosinolate substrate and reaction conditions.

    abstract::Glucosinolates are plant secondary metabolites that are part of a plant defence system against pathogens and pests, the myrosinase-glucosinolate system, in which glucosinolates get activated by enzymic degradation through thioglucoside glucohydrolases called myrosinases. Epithiospecifier protein (ESP) and nitrile-spec...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.08.004

    authors: Kong XY,Kissen R,Bones AM

    更新日期:2012-12-01 00:00:00

  • Metabolic profile of wound-induced changes in primary carbon metabolism in sugarbeet root.

    abstract::Injury to plant products by harvest and postharvest operations induces respiration rate and increases the demand for respiratory substrates. Alterations in primary carbon metabolism are likely to support the elevated demand for respiratory substrates, although the nature of these alterations is unknown. To gain insigh...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.12.016

    authors: Lafta AM,Fugate KK

    更新日期:2011-04-01 00:00:00

  • Amino acid sequence of the 26 kDa subunit of legumin-type seed storage protein of common buckwheat (Fagopyrum esculentum Moench): molecular characterization and phylogenetic analysis.

    abstract::The paper describes the amino acid sequence of a 26 kDa basic subunit of 13S globulin of common buckwheat (Fagopyrum esculentum Moench). The protein has 93 and 75% sequence homology with 11S globulin of Coffea arabica and beta subunit of 11S globulin of Cucurbita pepo respectively. The subunit has the "globally conser...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00755-0

    authors: Bharali S,Chrungoo NK

    更新日期:2003-05-01 00:00:00

  • Is the C:N ratio a reliable indicator of C allocation to primary and defence-related metabolisms in tomato?

    abstract::Plant growth and defence are both fuelled by compounds synthesized from a common pool of carbon and nitrogen, implying the existence of a competition for carbon and nitrogen allocation to both metabolisms. The ratio of carbon to nitrogen (C:N) of an organ is often regarded as a convenient indicator of growth and quali...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.12.003

    authors: Royer M,Larbat R,Le Bot J,Adamowicz S,Robin C

    更新日期:2013-04-01 00:00:00

  • WITHDRAWN: Phytochemical Society of North America.

    abstract::This article has been withdrawn at the request of the author(s) and/or editor. The Publisher apologizes for any inconvenience this may cause. The full Elsevier Policy on Article Withdrawal can be found at http://www.elsevier.com/locate/withdrawalpolicy. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.03.001

    authors: McIntosh C

    更新日期:2012-03-16 00:00:00

  • Vacuolar transport of the glutathione conjugate of trans-cinnamic acid.

    abstract::Red beet (Beta vulgaris L.) tonoplast membrane vesicles and [14C]trans-cinnamic acid-glutatione were used to study the vacuolar transport of phynylpropanoid-glutathione conjugates which are formed in peroxidase-mediated reactions. It was determined that the uptake of [14C]trans-cinnamic acid-glutathione into the tonop...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00563-4

    authors: Walczak HA,Dean JV

    更新日期:2000-02-01 00:00:00

  • Phytotoxic triterpene saponins from Bellis longifolia, an endemic plant of Crete.

    abstract::In a study of 62 plant species of the Cretan flora for their phytotoxic activity, plants were extracted successively with CH2Cl2, MeOH and H2O. Phytotoxicity evaluation of the 240 extracts was performed against Lactuca sativa L. and Agrostis stolonifera L.. The MeOH extract of Bellis longifolia was the most phytotoxic...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.08.019

    authors: Stavropoulou MI,Angelis A,Aligiannis N,Kalpoutzakis E,Mitakou S,Duke SO,Fokialakis N

    更新日期:2017-12-01 00:00:00

  • Integration of non-targeted metabolomics and automated determination of elemental compositions for comprehensive alkaloid profiling in plants.

    abstract::Plants produce a large array of specialized metabolites to protect themselves. Among these allelochemicals, alkaloids display highly diverse and complex structures that are directly related to their biological activities. Plant alkaloid profiling traditionally requires extensive and time-consuming sample preparation a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.06.011

    authors: Vanderplanck M,Glauser G

    更新日期:2018-10-01 00:00:00

  • A bidesmosidic hederagenin hexasaccharide from the roots of Symphytum officinale.

    abstract::A new bidesmosidic triterpenoidal saponin 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-alpha-L - arabinopyranosyl]-hederagenin-28-O-[alpha-L-rhamnopyranosyl- (1-->4)-beta-D- glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, was isolated from the roots of Symphytum officinale. The structure was a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00246-4

    authors: Mohammad FV,Noorwala M,Ahmad VU,Sener B

    更新日期:1995-09-01 00:00:00

  • Dimeric antioxidant and cytotoxic triterpenoid saponins from Terminalia ivorensis A. Chev.

    abstract::Three saponins, including two dimeric triterpenoid glucosides possessing an unusual skeleton, ivorenosides A and B, and a monomeric triterpenoid saponin (ivorenoside C), together with the known sericoside, were isolated from the bark of Terminalia ivorensis. Their structures were established on the basis of 1D and 2D ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.08.020

    authors: Ponou BK,Teponno RB,Ricciutelli M,Quassinti L,Bramucci M,Lupidi G,Barboni L,Tapondjou LA

    更新日期:2010-12-01 00:00:00

  • Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).

    abstract::The flavonoid profiles of two monotypic genera, Teucridium and Tripora, have been studied by analytical methods. These genera were formerly placed in the Verbenaceae, but are now classified in the Lamiaceae, subfamily Ajugoideae. The major flavonoids of both genera were identified as glycosides of scutellarein 4'-meth...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00192-9

    authors: Grayer RJ,Veitch NC,Kite GC,Paton AJ,Garnock-Jones PJ

    更新日期:2002-08-01 00:00:00

  • Nonenolides and cytochalasins with phytotoxic activity against Cirsium arvense and Sonchus arvensis: a structure-activity relationships study.

    abstract::A structure-activity relationships study was conducted assaying 15 natural analogues and derivatives belonging to two groups of organic compounds, nonenolides and cytochalasins, for their toxicity against the composite perennial weeds Cirsium arvense and Sonchus arvensis occurring through the temperate region of world...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.11.003

    authors: Berestetskiy A,Dmitriev A,Mitina G,Lisker I,Andolfi A,Evidente A

    更新日期:2008-02-01 00:00:00

  • p-coumaric acid esters from Tanacetum longifolium.

    abstract::Two new long chain alkyl p-coumaric acid esters (2-3) along with eicosanyl trans-p-coumarate (1) were isolated from chloroform extract of the roots of Tanacetum longifolium. The structures of new compounds were assigned as 21'-hydroxyheneicosanyl-4-hydroxy-(cis and trans) p-coumarate (2a, 2b) and 27'-hydroxy heptacosa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.08.023

    authors: Mahmood U,Kaul VK,Acharya R,Jirovetz L

    更新日期:2003-10-01 00:00:00