The first prenylation step in hyperforin biosynthesis.

Abstract:

:Prenylation reactions contribute considerably to the diversity of natural products. Polyprenylated secondary metabolites include hyperforin which is both quantitatively and pharmacologically a major constituent of the medicinal plant Hypericum perforatum (St. John's wort). Cell cultures of the related species Hypericum calycinum were found to contain a prenyltransferase activity which is likely to catalyze the first prenylation step in hyperforin biosynthesis. The enzyme was soluble and dependent on a divalent cation, with Fe2+ leading to maximum activity (Km=3.8 mM). The preferred prenyl donor was DMAPP (Km=0.46 mM) and the preferred prenyl acceptor was phlorisobutyrophenone (Km=0.52 mM). A broad pH optimum from 6.5 to 8.5 and a temperature optimum from 35 to 40 degrees C were observed. The formation of hyperforins in H. calycinum cell cultures was preceded by an increase in dimethylallyltransferase activity, with the maximum specific activity being 3.6 microkat/kg protein.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Boubakir Z,Beuerle T,Liu B,Beerhues L

doi

10.1016/j.phytochem.2004.10.020

subject

Has Abstract

pub_date

2005-01-01 00:00:00

pages

51-7

issue

1

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(04)00553-9

journal_volume

66

pub_type

杂志文章
  • Profiling of secondary metabolites in root exudates of Arabidopsis thaliana.

    abstract::To explore the chemical composition of root exudates of the model plant Arabidopsis thaliana a workflow for nontargeted metabolite profiling of the semipolar fraction of root exudates was developed. It comprises hydroponic plant cultivation and sampling of root exudates under sterile conditions, sample preparation by ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.10.003

    authors: Strehmel N,Böttcher C,Schmidt S,Scheel D

    更新日期:2014-12-01 00:00:00

  • Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak.

    abstract::The methanolic extract from the pericarps of Sapindus rarak DC. was found to show pancreatic lipase inhibitory activity (IC50=ca. 614 microg/mL). From the extract, oleanane-type triterpene oligoglycosides, rarasaponins I-III (1-3), and raraoside A (4), were isolated together with 13 known saponins and four known sesqu...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.06.015

    authors: Morikawa T,Xie Y,Asao Y,Okamoto M,Yamashita C,Muraoka O,Matsuda H,Pongpiriyadacha Y,Yuan D,Yoshikawa M

    更新日期:2009-06-01 00:00:00

  • Norditerpene and diterpene alkaloids from Aconitum variegatum.

    abstract::Aerial parts of Aconitum variegatum L. from the Pyrenees furnished four norditerpene alkaloids, 16 beta-hydroxycardiopetaline, 8-ethoxysachaconitine, 14-acetylgenicunine B, N-deethyl-N-19-didehydrosachaconitine, five diterpene alkaloids 15-veratroyldictizine, 15-veratroyl-17-acetyldictizine, 15-veratroyl-17-acetyl-19-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.01.019

    authors: Díaz JG,Ruiza JG,Herz W

    更新日期:2005-04-01 00:00:00

  • Why are so many food plants cyanogenic?

    abstract::A disproportionately large number of the most important human food plants is cyanogenic. The accumulated research of numerous people working in several different disciplines now allows a tenable explanation for this observation. Cyanogenesis by plants is not only a surprisingly effective chemical defence against casua...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(97)00425-1

    authors: Jones DA

    更新日期:1998-01-01 00:00:00

  • Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures.

    abstract::Hyperforin is an important antidepressant constituent of Hypericum perforatum (St. John's wort). Cell cultures of the related species H. calycinum were found to contain the homologue adhyperforin and to a low extent hyperforin, when grown in BDS medium in the dark. Adhyperforin formation paralleled cell culture growth...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.11.003

    authors: Klingauf P,Beuerle T,Mellenthin A,El-Moghazy SA,Boubakir Z,Beerhues L

    更新日期:2005-01-01 00:00:00

  • Diterpenoid from Salvia greggii.

    abstract::The structure of a diterpenoid, designated salvigresin, that was isolated from the aerial parts of Salvia greggii, has been confirmed by spectroscopic investigation and X-ray analysis. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00216-4

    authors: Kawahara N,Inoue M,Kawai Ki,Sekita S,Satake M,Goda Y

    更新日期:2003-08-01 00:00:00

  • Dietary phytoestrogens and health.

    abstract::The interest in the potential health effects of dietary phytoestrogens has increased with the findings that hormone replacement therapy is not as safe or effective as previously thought. This review summarizes the dietary sources of the phytoestrogens; isoflavonoids, stilbenes, coumestans and lignans. It also examines...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2004.03.005

    authors: Cornwell T,Cohick W,Raskin I

    更新日期:2004-04-01 00:00:00

  • Bioactive terpenoids from sunflower leaves cv. Peredovick.

    abstract::The CH(2)Cl(2) extract of dried leaves of Helianthus annuus L. cv. Peredovick(R) has yielded, in addition to the known sesquiterpene lactones annuolide E and leptocarpin, and the sesquiterpenes heliannuols A, C, D, F, G, H, I, the new bisnorsesquiterpene, annuionone E, and the new sesquiterpenes heliannuol L, helibisa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00370-9

    authors: Macías FA,Torres A,Galindo JL,Varela RM,Alvarez JA,Molinillo JM

    更新日期:2002-11-01 00:00:00

  • A flavonoid from Brassica rapa flower as the UV-absorbing nectar guide.

    abstract::The corolla of Brassica rapa has an UV-absorbing zone in its center, known as the nectar guide for attracting pollinating insects. The pigment which plays the role of the nectar guide was isolated from the petals and identified to be isorhamnetin 3,7-O-di-beta-D-glucopyranoside on the basis of MS and NMR spectroscopic...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00237-6

    authors: Sasaki K,Takahashi T

    更新日期:2002-10-01 00:00:00

  • Naphthoquinone metabolites of the fungi.

    abstract::Structures and physico-chemical properties of 100 naphthoquinone metabolites produced by filamentous fungi are reviewed. The conditions of pigment formation, biogenesis and the mechanism of biosynthesis of pigments by fungi are described. Sixty-three fungi cultures able to produce naphthoquinone are listed. The biolog...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(98)80053-8

    authors: Medentsev AG,Akimenko VK

    更新日期:1998-03-01 00:00:00

  • Discovery of small molecule inhibitors of xyloglucan endotransglucosylase (XET) activity by high-throughput screening.

    abstract::Small molecules (xenobiotics) that inhibit cell-wall-localised enzymes are valuable for elucidating the enzymes' biological roles. We applied a high-throughput fluorescent dot-blot screen to search for inhibitors of Petroselinum xyloglucan endotransglucosylase (XET) activity in vitro. Of 4216 xenobiotics tested, with ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.06.016

    authors: Chormova D,Franková L,Defries A,Cutler SR,Fry SC

    更新日期:2015-09-01 00:00:00

  • Putrescine N-methyltransferase--the start for alkaloids.

    abstract::Putrescine N-methyltransferase (PMT) catalyses S-adenosylmethionine (SAM) dependent methylation of the diamine putrescine. The product N-methylputrescine is the first specific metabolite on the route to nicotine, tropane, and nortropane alkaloids. PMT cDNA sequences were cloned from tobacco species and other Solanacea...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.06.012

    authors: Biastoff S,Brandt W,Dräger B

    更新日期:2009-10-01 00:00:00

  • 3 alpha-hydroxy-oleanane-type triterpene glycosyl esters from leaves of Acanthopanax spinosus.

    abstract::Three novel 3 alpha-hydroxy-oleanane-type triterpene oligoglycosyl esters, spinoside C1, C4 and C5, were isolated from the leaves of Acanthopanax spinosus. The structures were established to be 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl esters of 3 alpha, 29-dihydroxy-olean...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)90853-7

    authors: Miyakoshi M,Ida Y,Isoda S,Shoji J

    更新日期:1993-12-01 00:00:00

  • Anti-inflammatory and cytotoxic carbazole alkaloids from Murraya kwangsiensis.

    abstract::Chemical investigation of the traditional Chinese medicine, Murraya kwangsiensis, led to the isolation of 16 undescribed biscarbazole alkaloids, kwangsines A-M, two undescribed natural products, (+/-)-bispyrayafoline C, and 19 known monomeric analogues. (±)-Bispyrayafoline C and (±)-kwangsines A-C are four pairs of bi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2019.112186

    authors: Chen Y,Cao N,Lv H,Zeng K,Yuan J,Guo X,Zhao M,Tu P,Jiang Y

    更新日期:2020-02-01 00:00:00

  • Jatrophane diterpenoids from Euphorbia peplus.

    abstract::From the pro-inflammatory active extract of Euphorbia peplus, a new diterpene polyester (1) based on the jatrophane skeleton was isolated together with the known compounds 2-5. The irritant activities of some jatrophane diterpenes (2, 3 and 6-9) were also investigated: only compound 2 was found to exert a weak pro-inf...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00088-6

    authors: Hohmann J,Vasas A,Günther G,Dombi G,Blazsó G,Falkay G,Máthé I,Jerkovich G

    更新日期:1999-07-01 00:00:00

  • Heterogeneity of carrageenans from Chondrus crispus.

    abstract::Carrageenans extracted from gametophytic and sporophytic Chondrus crispus were analysed by hydrolysis, KCl fractionation and 1H NMR spectroscopy. The carrageenan from gametophytic plants is composed predominantly of two KCl insoluble fractions which contain kappa-carrageenan as the major component with 1-carrageenan a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)90032-l

    authors: Matsuhiro B,Urzua CC

    更新日期:1992-02-01 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

  • Kahiricosides II-V, cycloartane glycosides from an Egyptian collection of Astragalus kahiricus.

    abstract::Four cycloartane-type saponins, kahiricosides II-V (1-4), were isolated from the aerial parts of Astragalus kahiricus of Egyptian origin. Their structures were established as 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetraol-3-O-beta-D-glucopyranoside, 9beta,19-cyclolanost-24E-ene-3beta,6alpha,16beta,27-tetr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.08.037

    authors: Radwan MM,El-Sebakhy NA,Asaad AM,Toaima SM,Kingston DG

    更新日期:2004-11-01 00:00:00

  • Volatile constituents of Capillipedium parviflorum.

    abstract::The essential oil of aerial parts of Capillipedium parviflorum (family Poaceae) was obtained by hydrodistillation in 0.4% yield on dry weight basis. The oil was analysed by capillary GC and GC-MS techniques. Two new compounds from plant source 4-nonanol 51.7% and 4-undecanone 23.5% predominated in the essential oil an...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.04.003

    authors: Mahmood U,Kaul VK,Acharya R

    更新日期:2004-07-01 00:00:00

  • Saikosaponin derivatives from Bupleurum wenchuanense.

    abstract::From the roots of Bupleurum wenchuanense 14 derivatives of saikosaponin were isolated and identified as 2"-O-beta-D-xylopyranosylsaikosaponin b2, 3",6"-O O-diacetylsaikosaponin b2, 2"-O-beta-D-glucopyranosylsaikosaponin b2, saikosaponin b2, 6"-O-acetylsaikosaponin b2, saikosaponin d, 2"-O-acetylsaikosaponin d, 3"-O-ac...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(93)85049-w

    authors: Luo SQ,Lin LZ,Cordell GA

    更新日期:1993-07-01 00:00:00

  • Biosynthesis of fomannoxin in the root rotting pathogen Heterobasidion occidentale.

    abstract::Fomannoxin is a biologically active benzohydrofuran, which has been suggested to be involved in the pathogenicity of the root rotting fungus Heterobasidion annosum sensu lato. The biosynthesis of fomannoxin was investigated through an isotopic enrichment study utilizing [1-¹³C]glucose as metabolic tracer. ¹³C NMR spec...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.08.008

    authors: Hansson D,Menkis A,Olson K,Stenlid J,Broberg A,Karlsson M

    更新日期:2012-12-01 00:00:00

  • Partial purification and characterisation of sugarcane neutral invertase.

    abstract::Sugarcane neutral invertase (SNI) has been partially purified from mature sugarcane stem tissue to remove any potential competing activity. The enzyme is non-glycosylated and exhibits catalytic activity as a monomer, dimer and tetramer, most of the activity elutes as a monomer of native M(r) ca 60 k. The enzyme displa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00204-0

    authors: Vorster DJ,Botha FC

    更新日期:1998-10-01 00:00:00

  • N,beta-D-Glucopyranosyl vincosamide, a light regulated indole alkaloid from the shoots of Psychotria leiocarpa.

    abstract::From leaves of Psychotria leiocarpa, an indole alkaloid was isolated to which the structure N,beta-D-glucopyranosyl vincosamide (1) was assigned. This represents the first report of an N-glycosylated monoterpenoid indole alkaloid. In field-grown plants highest amounts of 1 were found in the leaves (2.5% of dry wt) and...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.10.027

    authors: Henriques AT,Lopes SO,Paranhos JT,Gregianini TS,Von Poser GL,Fett-Neto AG,Schripsema J

    更新日期:2004-02-01 00:00:00

  • The effect of growth temperature on the long-chain alkenes composition in the marine coccolithophorid Emiliania huxleyi.

    abstract::The hydrocarbon fraction of a pure culture of Emiliania huxleyi, composed of a mixture of C31, C33, C37 and C38 polyunsaturated n-alkenes, appeared strongly dependent on the growth temperature of the alga between 8 degrees C and 25 degrees C. The total hydrocarbon content increased linearly with decreasing temperature...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00120-5

    authors: Grossi V,Raphel D,Aubert C,Rontani JF

    更新日期:2000-06-01 00:00:00

  • Caudatan A, an undescribed human kidney-type glutaminase inhibitor with tetracyclic flavan from Ohwia caudata.

    abstract::Human kidney-type glutaminase (KGA) is an important target that is often over expressed in many cancer cells but very few effective inhibitors of this enzyme have yet reached clinical trials. Caudatan A and caudatan B, two undescribed tetracyclic flavans with an unusual ether bond between the C-4 and C-2' were isolate...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.04.013

    authors: Sun Y,Feng X,Liu X,Qian C,Che X,Cao F,Jin S,Meng D

    更新日期:2018-08-01 00:00:00

  • Changes in wheat leaf phenolome in response to cold acclimation.

    abstract::A study of wheat (Triticum aestivum L.) leaves phenolome was carried out during cold acclimation of the winter (Claire) and spring (Bounty) varieties using a combination of HPLC-ESI-MS techniques. A total of 40 phenolic and flavonoid compounds were identified, and consisted mainly of two coumarin derivatives, eight si...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.08.021

    authors: Moheb A,Ibrahim RK,Roy R,Sarhan F

    更新日期:2011-12-01 00:00:00

  • A 1H NMR-based metabolomic approach to study the production of antimalarial compounds from Psiadia arguta leaves (pers.) voigt.

    abstract::Psiadia arguta (Asteraceae) is endemic to the island of Mauritius in the Indian Ocean. The species is traditionally used to treat various ailments, such as its use as an expectorant or for the treatment of bronchitis and asthma. Preliminary biological screenings have displayed the antimalarial (Plasmodium falciparum) ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112401

    authors: Mahadeo K,Grondin I,Herbette G,Palama TL,Bouchemal N,Soulange J,Laulloo SJ,Sadeyen J,Humeau L,Frederich M,Gauvin-Bialecki A,Kodja H

    更新日期:2020-08-01 00:00:00

  • Aporphine Alkaloids from Illigera aromatica from Guangxi Province, China.

    abstract::Three undescribed aporphine alkaloids laurodionine B (1), illigerine A (2), and N-formyl-laurolitsine (3) were isolated from the methanolic extracts of the Chinese medicinal plant, Illigera aromatica, together with three known analogues (4-6). The chemical structures of 1-6 were identified by spectroscopic methods inc...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.06.017

    authors: Ge YC,Zhang HJ,Wang KW,Fan XF

    更新日期:2018-10-01 00:00:00

  • Phenolic and triterpenoid glycosides from Aster batangensis.

    abstract::A new phenolic glycoside, asterbatanoside A [p-hydroxyacetophenone-4-O-beta-D-xylopyranosyl-(1-->6)-beta-D- glucopyranoside], and two new triterpenoid saponins, asterbatanoside B [2 alpha,3 beta,23-trihydroxyolean-12-en-28-oic acid-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside] and asterbatanoside C [3-O-b...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00219-7

    authors: Shao Y,Li YL,Zhou BN

    更新日期:1996-04-01 00:00:00

  • Lipoxygenases - Structure and reaction mechanism.

    abstract::Lipid oxidation is a common metabolic reaction in all biological systems, appearing in developmentally regulated processes and as response to abiotic and biotic stresses. Products derived from lipid oxidation processes are collectively named oxylipins. Initial lipid oxidation may either occur by chemical reactions or ...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.05.008

    authors: Andreou A,Feussner I

    更新日期:2009-09-01 00:00:00