Minor C-geranylated flavanones from Paulownia tomentosa fruits with MRSA antibacterial activity.

Abstract:

:Exhaustive chromatographic separation of the chloroform portion of the ethanolic extract obtained from Paulownia tomentosa (Thunb). Steud. (Paulowniaceae) fruits has led to isolation of ten C-6 geranylated flavanones tomentodiplacone C-I and mimulone C-E, featured by 3'-methoxy and 4'-hydroxy or 4'-hydroxy substitution of the B-ring of the flavonoid, respectively. The structures of these compounds were determined by using mass spectrometry (including HRMS) and 1D and 2D NMR spectroscopy. The absolute configurations of the compounds at C-2 were determined using circular dichroism. The obtained compounds showed the presence of a geranyl moiety functionalized by a carbonyl, hydroxyl or methoxyl group, or by formation of tetrahydrofuran or fused-pyrane ring, respectively. All of the flavanones described were isolated for the first time from a natural source. The antibacterial activities of selected compounds isolated along with the previously isolated geranylated flavanones were evaluated against a common panel of microbes and MRSA strains. The selected isolated compounds were tested for their ability to affect eukaryotic translation initiation via dual-luciferase reporter assay (firefly and renilla).

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Navrátilová A,Schneiderová K,Veselá D,Hanáková Z,Fontana A,Dall'Acqua S,Cvačka J,Innocenti G,Novotná J,Urbanová M,Pelletier J,Čížek A,Žemličková H,Šmejkal K

doi

10.1016/j.phytochem.2013.01.002

subject

Has Abstract

pub_date

2013-05-01 00:00:00

pages

104-13

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(13)00024-1

journal_volume

89

pub_type

杂志文章
  • Analysis of commercial proanthocyanidins. Part 2: An electrospray mass spectrometry investigation into the chemical composition of sulfited quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood extract.

    abstract::Proanthocyanidins (PACs) are natural plant-derived polymers used in leather tanning, wood adhesives, water purification, and mud additives for oil drilling. Quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood and mimosa (Acacia mearnsii) bark extracts are the major industrial sources of PACs. These comm...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.01.027

    authors: Venter PB,Senekal ND,Amra-Jordaan M,Bonnet SL,Van der Westhuizen JH

    更新日期:2012-06-01 00:00:00

  • Production of bioactive triterpenes by Eriobotrya japonica calli.

    abstract::Callus tissue cultures induced from an axenic leaf of Eriobotrya japonica (Rosaceae) produced triterpenes in large amounts (ca. 50 mg/g dry wt). Nine triterpenes were characterized as ursolic acid, oleanolic acid, 2alpha-hydoxyursolic acid, maslinic acid, tormentic acid, 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00455-1

    authors: Taniguchi S,Imayoshi Y,Kobayashi E,Takamatsu Y,Ito H,Hatano T,Sakagami H,Tokuda H,Nishino H,Sugita D,Shimura S,Yoshida T

    更新日期:2002-02-01 00:00:00

  • Dhurrin-6'-glucoside, a cyanogenic diglucoside from Sorghum bicolor.

    abstract::A novel cyanogenic diglucoside has been isolated from methanolic extracts of young seedlings of Sorghum bicolor. Its structure was established as dhurrin-6-glucoside from NMR, mass spectrometry and enzymatic hydrolysis data. Compared with dhurrin, which is the major cyanogenic glucoside in sorghum leaves, dhurrin-6-gl...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(96)00297-x

    authors: Selmar D,Irandoost Z,Wray V

    更新日期:1996-10-01 00:00:00

  • ent-Labdane diterpenes from the aquatic plant Potamogeton pectinatus.

    abstract::Four new ent-labdane diterpenes were isolated from the freshwater aquatic plant Potamogeton pectinatus, together with two known furano-ent-labdanes. The new compounds were assigned the structures methyl-15,16-epoxy-12(R)-acetoxy- 8(17), 13(16),14-ent-labdatrien-19-oate,15,16-epoxy-12(R)-acetoxy-8(17), 13(16),14-ent-la...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.08.014

    authors: Waridel P,Wolfender JL,Lachavanne JB,Hostettmann K

    更新日期:2003-12-01 00:00:00

  • Age and nutrient limitation enhance polyunsaturated aldehyde production in marine diatoms.

    abstract::Skeletonema marinoi produces 2,4-heptadienal, 2,4-octadienal, and 2,4,7-octatrienal, the latter only in traces. In nutrient-replete cultures, the production of potentially defensive polyunsaturated aldehydes (PUA) increases from the exponential to the stationary phase of growth from 1.2 fmol cell(-1) (+/-0.4 fmol cell...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.012

    authors: Ribalet F,Wichard T,Pohnert G,Ianora A,Miralto A,Casotti R

    更新日期:2007-08-01 00:00:00

  • Triterpenoid glycosides from Adina rubella.

    abstract::Two new triterpenoid glycosides, quinovic acid-3 beta-O-beta-D- glucopyranosyl-(1-->4)-alpha-L-rhamnopyranoside and quinovic acid-3 beta-O-beta-D-glucopyranosyl-(1-->3)-beta-D-fucopyranoside (named rubelloside A and B, respectively), were isolated from roots of Adina rubella. Their structures were elucidated by spectr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00119-r

    authors: Fang SY,He ZS,Gao JH,Wang P

    更新日期:1995-07-01 00:00:00

  • Evolution of pyrrolizidine alkaloids in Phalaenopsis orchids and other monocotyledons: identification of deoxyhypusine synthase, homospermidine synthase and related pseudogenes.

    abstract::In order to study the evolution of pathways of plant secondary metabolism, we use the biosynthesis of pyrrolizidine alkaloids (PAs) as a model system. PAs are regarded as part of the plant's constitutive defense against herbivores. Homospermidine synthase (HSS) is the first specific enzyme of PA biosynthesis. The gene...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.01.019

    authors: Nurhayati N,Gondé D,Ober D

    更新日期:2009-03-01 00:00:00

  • Chromenes of polyketide origin from Peperomia villipetiola.

    abstract::An extract of leaves and stems of Peperomia villipetiola has been found to contain myristicin (3-methoxy-4,5-methylenedioxy-allylbenzene) and seven chromenes, whose structures are methyl 5-hydroxy-7-methyl-2,2-dimethyl-2H-1-chromene-6-carboxylate (1), methyl 5-methoxy-7-methyl-2,2-dimethyl-2H-1-chromene-8-carboxylate ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.01.003

    authors: Malquichagua Salazar KJ,Delgado Paredes GE,Lluncor LR,Young MC,Kato MJ

    更新日期:2005-03-01 00:00:00

  • Triterpene saponins and flavonoids in the seeds of Trifolium species.

    abstract::Seeds of 57 species of the genus Trifolium have been studied for the occurrence and concentration of soyasapogenol B glycosides and flavonoids. It was shown that all tested species contained soyasaponin I and in some species astragaloside VIII and/or 22-O-glucoside and 22-O-diglucoside of soyasaponin I were also prese...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00230-3

    authors: Oleszek W,Stochmal A

    更新日期:2002-09-01 00:00:00

  • Meroterpenoids with diverse structures and anti-inflammatory activities from Rhododendron anthopogonoides.

    abstract::Eight pairs of meroterpenoid enantiomers and four achiral meroterpenoids were isolated from Rhododendron anthopogonoides Maxim. Seventeen of them, named (+)-/(-)-anthoponoids A-G, (+)-daurichromene D, and anthoponoids H and I, are undescribed compounds with structural diversity. Their structures were characterized her...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112524

    authors: Shi Q,Li TT,Wu YM,Sun XY,Lei C,Li JY,Hou AJ

    更新日期:2020-12-01 00:00:00

  • Antibacterial compounds from Carissa lanceolata R.Br.

    abstract::The dichloromethane extract of the wood of Carissa lanceolata R.Br. (Apocynaceae) afforded the eudesmanes carissone, dehydrocarissone and carindone. This is the first account of carissone being isolated from the wood of C. lanceolata, and of carindone being isolated from this Carissa species. Dehydrocarissone has not ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00343-5

    authors: Lindsay EA,Berry Y,Jamie JF,Bremner JB

    更新日期:2000-11-01 00:00:00

  • Steroidal saponins from the leaves of Cordyline stricta.

    abstract::Three new spirostanol saponins and two new furostanol saponins were isolated from the fresh leaves of Cordyline stricta. Their structures were elucidated on the basis of spectroscopic analysis, including various 2D NMR techniques, hydrolysis, and by comparison of spectral data of known compounds. Two of the isolated s...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00545-1

    authors: Mimaki Y,Kuroda M,Takaashi Y,Sashida Y

    更新日期:1998-01-01 00:00:00

  • Cordifolisides A, B, C: norditerpene furan glycosides from Tinospora cordifolia.

    abstract::Several glycosides were isolated, as polyacetates, from the n-BuOH fraction of the Tinospora cordifolia stems. The structures of three new norditerpene furan glycosides cordifoliside A, B and C have been established by 1D and 2D NMR spectroscopy. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)90358-3

    authors: Gangan VD,Pradhan P,Sipahimalani AT,Banerji A

    更新日期:1994-10-01 00:00:00

  • Molecular cloning and characterization of an amidase from Arabidopsis thaliana capable of converting indole-3-acetamide into the plant growth hormone, indole-3-acetic acid.

    abstract::Acylamidohydrolases from higher plants have not been characterized or cloned so far. AtAMI1 is the first member of this enzyme family from a higher plant and was identified in the genome of Arabidopsis thaliana based on sequence homology with the catalytic-domain sequence of bacterial acylamidohydrolases, particularly...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00563-0

    authors: Pollmann S,Neu D,Weiler EW

    更新日期:2003-02-01 00:00:00

  • Targeted metabolite profiling provides a functional link among eucalypt taxonomy, physiology and evolution.

    abstract::Adaptation to aridity is considered a major factor in the evolution of the genus Eucalyptus. For the first time, targeted metabolite profiling has uncovered a quantitative yet discrete phytochemical link with eucalypt taxonomy. The distribution of cyclitols among Eucalyptus species, and a range of other Australian tre...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.11.027

    authors: Merchant A,Richter A,Popp M,Adams M

    更新日期:2006-02-01 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

  • Triterpenoid saponins from Dianthus chinensis.

    abstract::Two novel triterpenoid saponins, dianchinenoside C [23-O-beta-D-glucopyranosyl 3 beta, 16 alpha-dihydroxyolean-12-ene 23 alpha, 28 beta-dioic acid 28-O-beta-D-glucopyranoside] and dianchinenoside D [3 beta, 16 alpha-dihydroxyolean-12-ene 23 alpha, 28 beta-dioic acid 28-O-beta-D-glucopyranosyl [1-->6)-beta-D-glucopyran...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)90599-5

    authors: Li HY,Koike K,Ohmoto T

    更新日期:1994-02-01 00:00:00

  • Cholestane and spirostane glycosides from the rhizomes of Dioscorea septemloba.

    abstract::Cholestane glycosides, dioseptemlosides A (1) and B (2), together with six spirostane glycosides, dioseptemlosides C-H (3-8), were isolated from the rhizomes of Dioscorea septemloba. Their structures were established on the basis of physical data, spectroscopic analysis (HRESIMS, 1D and 2D NMR), and chemical methods. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.12.014

    authors: Liu XT,Wang ZZ,Xiao W,Zhao HW,Hu J,Yu B

    更新日期:2008-04-01 00:00:00

  • Four tetracyclic oxindole alkaloids and a taberpsychine derivative from a Malayan Tabernaemontana.

    abstract::Four tetracyclic oxindole alkaloids, 7(R)- and 7(S)-geissoschizol oxindole (1 and 2), 7(R),16(R)- and 7(S),16(R)-19(E)-isositsirikine oxindole (3 and 4), in addition to a taberpsychine derivative, N(4)-demethyltaberpsychine (5), were isolated from the Malayan Tabernaemontana corymbosa and the structures were establish...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.06.010

    authors: Lim KH,Sim KM,Tan GH,Kam TS

    更新日期:2009-06-01 00:00:00

  • Antimicrobial activities of sesquiterpene lactones and inositol derivatives from Hymenoxys robusta.

    abstract::Six compounds from the aerial parts of the Argentinean plant Hymenoxys robusta (Rusby) Parker were isolated and their structures elucidated using extensive spectroscopic analyses. These compounds comprise two inositol derivatives and four 3,4-seco-pseudoguaianolides, including vermeerin. Bioactivity assays of these co...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.09.001

    authors: Fortuna AM,Juárez ZN,Bach H,Nematallah A,Av-Gay Y,Sánchez-Arreola E,Catalán CA,Turbay S,Hernández LR

    更新日期:2011-12-01 00:00:00

  • Determination of hydroxycinnamic acids present in Rhododendron species.

    abstract::Hydroxycinnamates including free hydroxycinnamic acids and their chlorogenic acid derivatives and glycosides have been profiled in leaf extracts of 98 Rhododendron species using LC-MS techniques. In total, 69 hydroxycinnamic acid derivatives were identified in the leaves of 98 Rhododendron species. Some derivatives se...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.09.018

    authors: Shrestha A,Hakeem Said I,Grimbs A,Thielen N,Lansing L,Schepker H,Kuhnert N

    更新日期:2017-12-01 00:00:00

  • The microbiological transformation of 7alpha-hydroxy-ent-kaur-16-ene derivatives by Gibberella fujikuroi.

    abstract::The biotransformation of 7alpha-hydroxy-ent-kaur-16-ene (epi-candol A) by the fungus Gibberella fujikuroi gave 7alpha,16alpha,17-trihydroxy-ent-kaur-16-ene and a seco-ring B derivative, fujenoic acid, whilst the incubation of candicandiol (7alpha,18-dihydroxy-ent-kaur-16-ene) and canditriol (7alpha,15alpha,18-trihydro...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.03.024

    authors: Fraga BM,Bressa C,González P,Guillermo R,Hernández MG,Suárez S

    更新日期:2007-06-01 00:00:00

  • Direct NMR analysis of cannabis water extracts and tinctures and semi-quantitative data on delta9-THC and delta9-THC-acid.

    abstract::Cannabis sativa L. is the source for a whole series of chemically diverse bioactive compounds that are currently under intensive pharmaceutical investigation. In this work, hot and cold water extracts as well as ethanol/water mixtures (tinctures) of cannabis were compared in order to better understand how these extrac...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.07.018

    authors: Politi M,Peschel W,Wilson N,Zloh M,Prieto JM,Heinrich M

    更新日期:2008-01-01 00:00:00

  • On the propensity of lignin to associate: a size exclusion chromatography study with lignin derivatives isolated from different plant species.

    abstract::Despite evidence that lignin associates under both aqueous and organic media, the magnitude and nature of the underlying driving forces are still a matter of discussion. The present paper addresses this issue by examining both solution properties and size exclusion behaviour of lignins isolated from five different spe...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.026

    authors: Guerra A,Gaspar AR,Contreras S,Lucia LA,Crestini C,Argyropoulos DS

    更新日期:2007-10-01 00:00:00

  • Diarylheptanoids from Myrica arborea.

    abstract::Investigations of the stem and root bark of Myrica arborea (Myricaceae) have yielded two novel diarylheptanoids, myricarborin and 11-O-beta-D-xylopyranosylmyricanol along with the known myricanol and 5-O-beta-D-glucopyranosylmyricanol. The structures of the novel compounds were determined by spectroscopic methods. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00164-3

    authors: Tene M,Wabo HK,Kamnaing P,Tsopmo A,Tane P,Ayafor JF,Sterner O

    更新日期:2000-08-01 00:00:00

  • Sebestenoids A-D, BACE1 inhibitors from Cordia sebestena.

    abstract::Bioassay-guided fractionation of an extract prepared from the fruits of Cordia sebestena led to the isolation of sebestenoids A-D (1-4). Their structures were elucidated on the basis of extensive NMR experiments and mass spectroscopic measurements. Compounds 1-4 exhibited moderate inhibition of the aspartic protease B...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.09.008

    authors: Dai J,Sorribas A,Yoshida WY,Williams PG

    更新日期:2010-12-01 00:00:00

  • Anti-plasmodial and antioxidant activities of constituents of the seed shells of Symphonia globulifera Linn f.

    abstract::A xanthone derivative, named gaboxanthone (1), has been isolated from the seed shells of Symphonia globulifera, together with known compounds, symphonin (2), globuliferin (3), guttiferone A (4), sistosterol, oleanolic acid and methyl citrate. The structure of the compound was assigned as 5,10-dihydroxy-8,9-dimethoxy-2...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.11.004

    authors: Ngouela S,Lenta BN,Noungoue DT,Ngoupayo J,Boyom FF,Tsamo E,Gut J,Rosenthal PJ,Connolly JD

    更新日期:2006-02-01 00:00:00

  • A lipase inhibitor monoterpene and monoterpene glycosides from Monarda punctata.

    abstract::An 80% acetone extract of Monarda punctata showed an inhibitory effect on lipase activity in isolated mouse plasma in vitro and carvacrol was obtained as the active constituent. It had an IC₅₀ value of 4.07 mM invitro and suppressed elevations in blood triacylglycerol levels in olive oil-loaded mice. Furthermore, from...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.08.009

    authors: Yamada K,Murata T,Kobayashi K,Miyase T,Yoshizaki F

    更新日期:2010-11-01 00:00:00

  • Biochemical characterization of two differentially expressed polyphenol oxidases from hybrid poplar.

    abstract::Two polyphenol oxidase isoforms with distinct expression patterns were identified in hybrid poplar (Populus trichocarpaxP. deltoides). PPO-1, corresponding to the previously cloned PtdPPO (Constabel et al., Plant Physiol. 124: 285-295) was primarily leaf tissue-specific and detected only after wounding. PPO-2 was expr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00159-6

    authors: Wang J,Constabel CP

    更新日期:2003-09-01 00:00:00

  • Friedolanostanes and xanthones from the twigs of Garcinia hombroniana.

    abstract::The twigs of Garcinia hombroniana yielded six compounds: two 17,14-friedolanostanes (garcihombronanes K-L, 1-2) and four xanthones (garcihombronones A-D, 3-6) together with 14 known compounds including four friedolanostanes, one lanostane, six xanthones, two benzoic acid derivatives and one biflavonoid. Their structur...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.08.020

    authors: Klaiklay S,Sukpondma Y,Rukachaisirikul V,Phongpaichit S

    更新日期:2013-01-01 00:00:00