Distribution of morphinan and benzo[c]phenanthridine alkaloid gene transcript accumulation in Papaver somninferum.

Abstract:

:The opium poppy Papaver somniferum L. produces the antimicrobial benzo[c]phenanthridine alkaloid sanguinarine and the narcotic analgesic morphinan alkaloid morphine. Transcripts of three genes of alkaloid biosynthesis in P. somniferum in developing seedlings, mature plants and plant cell suspension culture were monitored for temporal/spatial or for methyl jasmonate-induced accumulation by RNA gel blot analysis. These genes encoded (S)-N-methylcoclaurine 3'-hydroxylase (CYP80B1) that is common to morphine and sanguinarine biosynthesis, the berberine bridge enzyme (BBE) that lies on the pathway to sanguinarine, and codeinone reductase (COR) the penultimate enzyme of morphine biosynthesis. In developing P. somniferum seedlings, the morphine precursor thebaine was present throughout the first twenty days of germination. In contrast, sanguinarine was present in detectable quantities only after day five after germination and continued to increase at least until day twenty. Accumulation of cyp80b1, bbe1 and cor1 gene transcripts paralleled these differences. In the mature poppy plant, cyp80b1, bbe1 and cor1 gene transcripts were detected in the root, the stem, the leaf lamina and the leaf mid rib. Only cyp80b1 and cor1, however, were found in the flower bud and the capsule. Consistent with the fact that sanguinarine accumulation, but not that of morphine, can be induced in opium poppy cell suspension culture by addition of methyl jasmonate to the culture medium, cyp80b1 and bbe1, but not cor1 transcript accumulated in response to elicitor treatment.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Huang FC,Kutchan TM

doi

10.1016/s0031-9422(99)00600-7

subject

Has Abstract

pub_date

2000-03-01 00:00:00

pages

555-64

issue

5

eissn

0031-9422

issn

1873-3700

pii

S0031942299006007

journal_volume

53

pub_type

杂志文章
  • Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus grandifolia.

    abstract::In addition to Z-coniferyl and Z-sinapyl alcohols, bark extracts of Fagus grandifolia also contain significant amounts of the glucosides, Z-coniferin, Z-isoconiferin (previously called faguside) and Z-syringin. The corresponding E-isomers of these glucosides do not accumulate to a detectable level. The accumulation ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(88)80107-9

    authors: Lewis NG,Inciong EJ,Ohashi H,Towers GH,Yamamoto E

    更新日期:1988-01-01 00:00:00

  • Corynanthean, eburnan, secoleuconoxine, and pauciflorine alkaloids from Kopsia pauciflora.

    abstract::Eleven indole alkaloids, comprising four corynanthean, two eburnane, one aspidofractinine, one secoleuconoxine, one andranginine, and two pauciflorine type alkaloids were isolated from the stem-bark and leaf extracts of Kopsia pauciflora. Their structures were determined using NMR and MS analyses. The catharinensine t...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.09.014

    authors: Gan CY,Yoganathan K,Sim KS,Low YY,Lim SH,Kam TS

    更新日期:2014-12-01 00:00:00

  • Hemicellulosic polysaccharides from bamboo shoot cell-walls.

    abstract::Cell-wall polysaccharides of bamboo shoots were extracted with chelating reagent (CDTA, trans-1,2-cyclohexanediamine-N,N,N',N'-tetraacetic acid), Na(2)CO(3) and KOH solutions. Glycosyl composition and glycosyl linkage analyses showed that the hemicellulose was composed of arabinoxylan, (1-->3, 1-->4)-beta-D-glucan, xy...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00237-4

    authors: Edashige Y,Ishii T

    更新日期:1998-11-20 00:00:00

  • Highly glycosylated flavonols with an O-linked branched pentasaccharide from Iberis saxatilis (Brassicaceae).

    abstract::Four flavonol glycosides isolated from non-flowering leafy shoots of Iberis saxatilis (Brassicaceae) were characterised by spectroscopic and chemical methods as saxatilisins A-D, the 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside, 3-O-β-D-...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.12.009

    authors: Prescott TA,Kite GC,Porter EA,Veitch NC

    更新日期:2013-04-01 00:00:00

  • Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana.

    abstract::The glucosinolate content of various organs of the model plant Arabidopsis thaliana (L.) Heynh., Columbia (Col-0) ecotype, was analyzed at different stages during its life cycle. Significant differences were noted among organs in both glucosinolate concentration and composition. Dormant and germinating seeds had the h...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00549-6

    authors: Brown PD,Tokuhisa JG,Reichelt M,Gershenzon J

    更新日期:2003-02-01 00:00:00

  • The broad spectrum 2-oxoglutarate oxygenase inhibitor N-oxalylglycine is present in rhubarb and spinach leaves.

    abstract::2-Oxoglutarate (2OG) and ferrous iron dependent oxygenases are involved in many biological processes in organisms ranging from humans (where some are therapeutic targets) to plants. These enzymes are of significant biomedicinal interest because of their roles in hypoxic signaling and epigenetic regulation. Synthetic N...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.06.028

    authors: Al-Qahtani K,Jabeen B,Sekirnik R,Riaz N,Claridge TDW,Schofield CJ,McCullagh JSO

    更新日期:2015-09-01 00:00:00

  • Developments in aspects of ecological phytochemistry: the role of cis-jasmone in inducible defence systems in plants.

    abstract::The challenges and opportunities for protecting agricultural production of food and other materials will be met through exploiting the induction of defence pathways in plants to control pests, diseases and weeds. These approaches will involve processes that can be activated by application of natural products, patented...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2007.09.025

    authors: Pickett JA,Birkett MA,Bruce TJ,Chamberlain K,Gordon-Weeks R,Matthes MC,Napier JA,Smart LE,Woodcock CM

    更新日期:2007-11-01 00:00:00

  • Hypoglycemic triterpenes from Gynostemma pentaphyllum.

    abstract::To search for bioactive gypenosides and their analogues, a saponin enriched fraction and its hydrolyzate from Gynostemma pentaphyllum were phytochemically investigated. Fractionation by diverse chromatographic methods, including HPLC, Sephadex LH-20, silica gel, and C18 reverse phase silica gel, led to the isolation a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.08.008

    authors: Wang J,Ha TKQ,Shi YP,Oh WK,Yang JL

    更新日期:2018-11-01 00:00:00

  • Conversions of deoxyradicinin to radicinin and of radicinin to 3-epi-radicinin in the phytopathogenic fungus Bipolaris coicis.

    abstract::Radicinin is a phytotoxic and antibiotic metabolite produced by some phytopathogenic fungi. Precursor administration and cell-free experiments with deoxyradicinin and radicinin were carried out in Bipolaris coicis H13-3. When deoxyradicinin was administered to the fungus, radicinin and 3-epi-radicinin formed. When rad...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.11.010

    authors: Suzuki M,Sakuno E,Ishihara A,Tamura J,Nakajima H

    更新日期:2012-03-01 00:00:00

  • Defensive strategies in Geranium sylvaticum. Part 1: organ-specific distribution of water-soluble tannins, flavonoids and phenolic acids.

    abstract::A combination of high-resolution mass spectrometry and modern HPLC column technology, assisted by diode array detection, was used for accurate characterization of water-soluble polyphenolic compounds in the pistils, stamens, petals, sepals, stems, leaves, roots and seeds of Geranium sylvaticum. The organs contained a ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.05.013

    authors: Tuominen A,Toivonen E,Mutikainen P,Salminen JP

    更新日期:2013-11-01 00:00:00

  • Diels-Alder type adducts from Morus cathayana.

    abstract::Two natural Diels-Alder type adducts, cathayanon A (1) and cathayanon B (2), resembling sanggenon C (4) and O (3), were isolated from the root bark of Morus cathayana. Their structures were elucidated on the basis of spectroscopic evidence. The structure of 1 was confirmed by the results of X-ray crystallographic anal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00171-6

    authors: Shen RC,Lin M

    更新日期:2001-08-01 00:00:00

  • Patterns of phenylpropanoids in non-inoculated and potato virus Y-inoculated leaves of transgenic tobacco plants expressing yeast-derived invertase.

    abstract::The patterns of secondary metabolites in leaves of yeast invertase-transgenic tobacco plants (Nicotiana tabacum L. cv. Samsun NN) were analyzed. Plants expressing cytosolic yeast-derived invertase (cytInv) or apoplastic (cell wall associated) yeast invertase (cwInv) showed a characteristic phytochemical phenotype comp...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00422-2

    authors: Baumert A,Mock HP,Schmidt J,Herbers K,Sonnewald U,Strack D

    更新日期:2001-03-01 00:00:00

  • Nitrogen depletion and small R3-MYB transcription factors affecting anthocyanin accumulation in Arabidopsis leaves.

    abstract::Ternary complexes consisting of a R2R3-MYB, a bHLH and a WD40 protein (MBW complexes) regulate trichome formation and anthocyanin synthesis in plants. Small R3-MYBs interact with the MBW complexes to exert a negative feedback, and thereby participate in regulation of epidermal cell fate, for example trichome numbers a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.12.006

    authors: Nemie-Feyissa D,Olafsdottir SM,Heidari B,Lillo C

    更新日期:2014-02-01 00:00:00

  • Chemical polymorphism of the essential oils from populations of Thymus caespititius grown on the island S. Jorge (Azores).

    abstract::The compositions of the essential oils obtained from ten populations of Thymus caespititius grown on S. Jorge (Azores) were studied by GC and GC-MS. All the oils analysed were dominated by their monoterpene fraction (69-9%). The sesquiterpene fraction was rather small (4-17%) and consisted mainly of oxygen-containing ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00278-8

    authors: Pereira SI,Santos PA,Barroso JG,Figueiredo AC,Pedro LG,Salgueiro LR,Deans SG,Scheffer JJ

    更新日期:2000-10-01 00:00:00

  • Two linear acetogenins from Goniothalamus gardneri.

    abstract::Two new acetogenins, gardnerilins A and B, have been isolated from the roots of Goniothalamus gardneri. Both are C35 acetogenins containing non-tetrahydrofuran rings. Their structures have been established on the basis of spectral evidence. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00959-x

    authors: Chen Y,Jiang Z,Chen RR,Yu DQ

    更新日期:1998-11-01 00:00:00

  • Production of phenylacetic acid derivatives and 4-epiradicinol in culture by Curvularia lunata.

    abstract::Phenylacetic acid derivatives, methyl 2-acetyl-3,5-dihydroxyphenylacetate (1) and methyl 2-acetyl-5-hydroxy-3-methoxyphenylacetate (3); curvulin or ethyl 2-acetyl-3,5-dihydroxyphenylacetate (4), a known metabolite of Curvularia siddiqui, and 4-epiradicinol (5) have been isolated from the culture mycelia of Curvularia ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.05.032

    authors: Varma GB,Fatope MO,Marwah RG,Deadman ME,Al-Rawahi FK

    更新日期:2006-09-01 00:00:00

  • Cladocalol, a pentacyclic 28-nor-triterpene from Eucalyptus cladocalyx with cytotoxic activity.

    abstract::A formylated triterpene named cladocalol has been isolated from the leaves of Eucalyptus cladocalyx, together with ursulolactone acetate, ursolic acid, 3 beta-acetate-12,20(29)-lupadien-28-oic acid, beta-sitosterol and the known flavonoid eucalyptine. Their structures were mainly established by extensive NMR studies (...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.12.018

    authors: Benyahia S,Benayache S,Benayache F,León F,Quintana J,López M,Hernández JC,Estévez F,Bermejo J

    更新日期:2005-03-01 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

  • Purification, sequencing and characterization of phospholipase D from Indian mustard seeds.

    abstract::Phospholipase D (PLD; E.C. 3.1.4.4) is widespread in plants where it fulfills diverse functions in growth and in the response to stresses. The enzyme occurs in multiple forms that differ in their biochemical properties. In the present paper PLD from medicinally relevant Indian mustard seeds was purified by Ca(2+)-medi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.05.022

    authors: Khatoon H,Mansfeld J,Schierhorn A,Ulbrich-Hofmann R

    更新日期:2015-09-01 00:00:00

  • Seco diterpenoids from Excoecaria agallocha L.

    abstract::Chemical examination of the ethyl acetate solubles of the CH(3)OH:CH(2)Cl(2) (1:1) extract of the roots of Excoecaria agallocha L. collected from Godavary estuary resulted in the isolation of three more new diterpenoids, agallochins M-O (1-3). The structures of the new diterpenoids were elucidated by a study of their ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00269-8

    authors: Anjaneyulu AS,Rao VL

    更新日期:2003-02-01 00:00:00

  • Oleanane triterpenes with protein tyrosine phosphatase 1B inhibitory activity from aerial parts of Lantana camara collected in Indonesia and Japan.

    abstract::During the search for new protein tyrosine phosphatase (PTP) 1B inhibitors, EtOH extracts from the aerial parts of Lantana camara L. (lantana) collected at Manado (Indonesia) and two subtropical islands in Japan (Ishigaki and Iriomote Islands, Okinawa) exhibited potent inhibitory activities against PTP1B in an enzyme ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.08.020

    authors: Abdjul DB,Yamazaki H,Maarisit W,Rotinsulu H,Wewengkang DS,Sumilat DA,Kapojos MM,Losung F,Ukai K,Namikoshi M

    更新日期:2017-12-01 00:00:00

  • Isolation and synthesis of chalcones with different degrees of saturation.

    abstract::Crotaoprostrin, a chalcone not yet known as a plant constituent, was isolated from the aerial parts of the Indian medicinal plant Crotalaria prostrata. The structures of the chalcone polyarvin and the partially hydrogenated naturally occurring derivatives crotaramin, crotaramosmin, and crotin were confirmed by chemica...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00475-2

    authors: Krohn K,Steingröver K,Srinivasa Rao M

    更新日期:2002-12-01 00:00:00

  • Triglucosylation on the biotransformation of (+)-menthol by cultured cells of Eucalyptus perriniana.

    abstract::Cultured cells of Eucalyptus perriniana biotransformed (+)-menthol to its gentiobioside and triglucoside [2,6-di-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside]. The structures of these compounds were determined by means of NMR techniques. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)85025-u

    authors: Orihara Y,Miyatake H,Furuya T

    更新日期:1991-01-01 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

  • Macrocyclic trichothecenes are undetectable in kudzu (Pueraria montana) plants treated with a high-producing isolate of Myrothecium verrucaria.

    abstract::Myrothecium verrucaria was found to be an effective pathogen against kudzu grown in the greenhouse and the field. M. verrucaria produced large amounts of macrocyclic trichothecenes when cultured on solid rice medium, including epiroridin E (16.8 mg/g crude extract), epiisororidin E (1 mg/g), roridin E (8.7 mg/g), rori...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00214-x

    authors: Abbas HK,Tak H,Boyette CD,Shier WT,Jarvis BB

    更新日期:2001-09-01 00:00:00

  • 2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'O-malonyl-beta-D-glucopyranoside in strawberry fruits.

    abstract::2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'-O-malonyl-beta-D-glucopyranoside was isolated from a glycosidic extract of strawberry fruit (Fragaria x ananassa, cv. Senga Sengana) by means of countercurrent chromatography and reverse-phase HPLC. Identification was achieved by comparison of chromatographic and 1H, 13C and 2D...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(96)00216-6

    authors: Roscher R,Herderich M,Steffen JP,Schreier P,Schwab W

    更新日期:1996-09-01 00:00:00

  • Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase.

    abstract::Carrot (Daucus carota subsp. sativus) is a widely cultivated root vegetable of high economic importance. The aroma of carrot roots and aboveground organs is mainly defined by terpenes. We found that leaves of orange carrot cultivar also produce considerable amounts of the phenylpropenes methyleugenol and methylisoeuge...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.12.020

    authors: Yahyaa M,Berim A,Nawade B,Ibdah M,Dudareva N,Ibdah M

    更新日期:2019-03-01 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

  • The isolation, structure and fragmentation characteristics of natural truxillic and truxinic acid derivatives in Abrus mollis leaves.

    abstract::Five undescribed compounds were separated from Abrus mollis leaves, including two truxillate forms (abrusamide D, H) and three truxinate forms (abrusamide E, F, G). The absolute configuration of abrusamide D was determined by X-ray crystallography. Abrusamide A was reassessed and corrected to be β-truxinate configurat...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112572

    authors: Yuan X,Liu Y,Zhao H,Men L,He C,Qiu Y,Yu Q,Li K,Qi L,Chen D

    更新日期:2021-01-01 00:00:00

  • Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit.

    abstract::Two sulfur-containing compounds, (S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid (1) and (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid (2), and one 1H-pyrrole-2-carboxylic acid deriva...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.08.014

    authors: Zheng ZP,Ma J,Cheng KW,Chao J,Zhu Q,Chang RC,Zhao M,Lin ZX,Wang M

    更新日期:2010-12-01 00:00:00