Peltogynoids and 2-phenoxychromones from Peltophorum pterocarpum and evaluation of their estrogenic activity.

Abstract:

:Phytochemical investigation of the dichloromethane extract of the leaves of Peltophorum pterocarpum, a tropical ornamental tree, led to the isolation of twelve compounds (1-12). One new derivative of peltogynoid ophioglonin (1) and a new 2-phenoxychromone (2) with its 3'-O-β-D-glucoside derivative (3) are described here for the first time. In addition, nine flavonoid derivatives, including peltogynoid ophioglonin (4), were isolated for the first time from this plant. The structures were determined by spectroscopic and chemical methods. Evaluation of the estrogenic activities of 1, 2, and 4 using different model cell systems revealed that 4 was estrogenic and that 2 was largely inactive. Interestingly, 1 was unable to stimulate the proliferation of breast and endometrial cancer cells but exhibited substantial estrogen receptor α-mediated activation of gene expression. This observation indicates that 1 can be further evaluated for its cancer chemopreventive potential.

journal_name

Planta Med

journal_title

Planta medica

authors

Polasek J,Queiroz EF,Marcourt L,Meligova AK,Halabalaki M,Skaltsounis AL,Alexis MN,Prajogo B,Wolfender JL,Hostettmann K

doi

10.1055/s-0032-1328299

subject

Has Abstract

pub_date

2013-04-01 00:00:00

pages

480-6

issue

6

eissn

0032-0943

issn

1439-0221

journal_volume

79

pub_type

杂志文章
  • Dysoxydensins A-G, seven new clerodane diterpenoids from Dysoxylum densiflorum.

    abstract::Seven new clerodane diterpenoids, dysoxydensins A-G (1-7), together with six known clerodanes, were isolated from Dysoxylum densiflorum. The structures of all the compounds were elucidated by extensive spectroscopic analysis. These compounds were evaluated for their cytotoxic activities against five human cancer cell ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0034-1382903

    authors: Gu J,Cheng GG,Qian SY,Li Y,Liu YP,Luo XD

    更新日期:2014-08-01 00:00:00

  • Steroidal saponins from Tribulus terrestris.

    abstract::Three new steroidal saponins were isolated from the fruits of Tribulus terrestris, and their structures were elucidated as (25R,S)-5 alpha-spirostane-12-one-3 beta-ol-3-O-beta-xylopyranosyl(1-->2)- [beta-xylopyranosyl(1-->3)]-beta-glucopyranosyl(1-->4)-[alpha-rhamno- pyranosyl(1-->2)]-beta-galactopyranoside; 26-O-beta...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2001-11650

    authors: Cai L,Wu Y,Zhang J,Pei F,Xu Y,Xie S,Xu D

    更新日期:2001-03-01 00:00:00

  • Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica.

    abstract::Aquaticol, an unusual bis-sesquiterpene was isolated from the medicinal plant Veronica anagallis-aquatica, in addition to 11 known compounds, aucubin, geniposidic acid, mussaenoside, catalposide, verproside, amphicoside, catalpol, boschnaloside, shanzhiside methyl ester, sitosterol and beta-stigmast-4-en-6 beta-ol-3-o...

    journal_title:Planta medica

    pub_type: 信件

    doi:10.1055/s-2000-8564

    authors: Su BN,Yang L,Gao K,Jia ZJ

    更新日期:2000-04-01 00:00:00

  • What Else Is in Salviae officinalis folium? Comprehensive Species Identification of Plant Raw Material by DNA Metabarcoding.

    abstract::Quality control of drugs consists of identifying the raw material to avoid unwanted admixtures or exchange of material as well as looking for abiotic and biotic contaminations. So far, identity and microbial contamination are analyzed by separate processes and separate methods. Species identification by their DNA ("DN...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0043-121470

    authors: Schmiderer C,Lukas B,Ruzicka J,Novak J

    更新日期:2018-04-01 00:00:00

  • The effect of N-deacetylcolchiceine on serum lipoproteins in rats.

    abstract::N-Deacetylcolchiceine (DAC) administered i.p. to rats decreased the level of serum cholesterol and apoB. It was accompanied by the fall of HDL-C due to the decrease of both HDL subfractions HDLa and HDLb, and by a rather weaker decrease of LDL-C. The levels of serum and lipoprotein triacylglycerols were not significan...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:

    authors: Skottová N,Vecera R,Walterová D,Simánek V

    更新日期:1992-02-01 00:00:00

  • Phytochemical Study of Eryngium triquetrum: Isolation of Polyacetylenes and Lignans.

    abstract::Phytochemical investigation of the ethyl acetate extract from the aerial parts of Eryngium triquetrum Vahl resulted in the isolation of new polyacetylenes, triquetridiol (6) and trans-epoxy-triquetrol (7a/7b, diastereomeric mixture), and the lignan demethoxy carolignan Z (8a/8b, erythro/threo pair), together with a se...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0042-110316

    authors: Bouzergoune F,Ciavatta ML,Bitam F,Carbone M,Aberkane MC,Gavagnin M

    更新日期:2016-11-01 00:00:00

  • Suppression of inducible nitric oxide synthase expression by diarylheptanoids from Alpinia officinarum.

    abstract::Six diarylheptanoids were isolated from the rhizome of Alpinia officinarum (Zingiberaceae) as inhibitors of nitric oxide (NO) production in the lipopolysaccharide-activated macrophage cell line RAW 264.7. A double bond at C-4 of the linker between two aromatic rings was found to be essential for activity. Furthermore,...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2005-873176

    authors: Lee HJ,Kim JS,Ryu JH

    更新日期:2006-01-01 00:00:00

  • New lignans and cytotoxic constituents from Wikstroemia lanceolata.

    abstract::Two new lignans, (-)-aptosimon ( 1) and (-)-diasesamin-di-gamma-lactone ( 2), together with twenty-two known compounds, have been isolated from the stems and roots of Wikstroemia lanceolata. The structures of the new compounds were determined through spectral analyses. The proton and carbon assignments of the known se...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2004-815540

    authors: Lin RW,Tsai IL,Duh CY,Lee KH,Chen IS

    更新日期:2004-03-01 00:00:00

  • Intestinal transport of 3,6'-disinapoylsucrose, a major active component of Polygala tenuifolia, using Caco-2 cell monolayer and in situ rat intestinal perfusion models.

    abstract::3,6'-Disinapoylsucrose is a major active component of the herb Polygala tenuifolia which has long been used for relieving tranquilization, uneasiness of the mind, and improving learning and memory. Our previous study found that 3,6'-disinapoylsucrose had a very low oral bioavailability. Its mechanisms of absorption in...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0033-1350794

    authors: Chen Y,Liu X,Pan R,Zhu X,Steinmetz A,Liao Y,Wang N,Peng B,Chang Q

    更新日期:2013-10-01 00:00:00

  • [Iridoid Glucosides from Euphrasia rostkoviana].

    abstract::Eight iridoid glucosides have been isolated from Euphrasia rostkoviana by the combination of open column- and high performance liquid chromatography. The structure of a new compound, named eurostoside, and the identity of the others have been established by chemical transformations and spectral evidence of the compoun...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-969960

    authors: Salama O,Sticher O

    更新日期:1983-02-01 00:00:00

  • Chemical constituents from the stem bark of Trewia nudiflora L. and their antioxidant activities.

    abstract::Three new compounds, namely, (+)-dihydrodehydrodiconiferyl alcohol 4- O- beta-(6''- O-galloyl)-glucopyranoside ( 1), 4,4'- O-dimethylellagic acid 3-(2''- O-acetyl)- alpha-rhamnopyranoside ( 2), and ethyl O- beta-(6'-galloyl)-glucopyranoside ( 3), together with eleven known ones, were isolated from the stem bark of Tre...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2008-1034361

    authors: Kang QJ,Yang XW,Wu SH,Ma YL,Li L,Shen YM

    更新日期:2008-03-01 00:00:00

  • Inhibition of lipid peroxidation and superoxide generation by diterpenoids from Rosmarinus officinalis.

    abstract::Four diterpenoids, carnosic acid (1), carnosol (2), rosmanol (3), and epirosmanol (4), were isolated as antioxidative agents from the leaves of Rosmarinus officinalis by bioassay-directed fractionation. These diterpenoids inhibited superoxide anion production in the xanthine/xanthine oxidase system. Mitochondrial and ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-958094

    authors: Haraguchi H,Saito T,Okamura N,Yagi A

    更新日期:1995-08-01 00:00:00

  • Allele-specific primers for diagnostic PCR authentication of Dendrobium officinale.

    abstract::Based on rDNA ITS sequences of D. officinale and the other 37 species of Dendrobium, a pair of allele-specific diagnostic primers, TP-JB01S and TP-JB01X, were designed to authenticate D. officinale from the other species. Before the diagnostic PCR, the primer pair, P1 and P2, for amplifying the whole ITS region was us...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2003-40651

    authors: Ding X,Wang Z,Zhou K,Xu L,Xu H,Wang Y

    更新日期:2003-06-01 00:00:00

  • [Biologically active compounds from the aqueous extract of Urtica dioica].

    abstract::From the water extract of the roots of Urtica dioica (stinging nettle) a polysaccharide fraction was isolated which revealed activity in the carrageenan rat paw edema model and lymphocyte transformation test. Ion exchange chromatography and gel filtration of this fraction afforded 4 different polysaccharides, one of w...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-962062

    authors: Wagner H,Willer F,Kreher B

    更新日期:1989-10-01 00:00:00

  • Procyanidines from Vitis vinifera seeds protect rabbit heart from ischemia/reperfusion injury: antioxidant intervention and/or iron and copper sequestering ability.

    abstract::An isolated rabbit heart Langendorff preparation paced electrically was used to evaluate the effects of a highly purified, high molecular weight fraction of oligomeric procyanidines isolated from Vitis vinifera seeds on myocardial reperfusion injury after 40 minutes of low flow (1 ml/min) ischemia. Infusion of the hea...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957956

    authors: Maffei Facinó R,Carini M,Aldini G,Berti F,Rossoni G,Bombardelli E,Morazzoni P

    更新日期:1996-12-01 00:00:00

  • Salidroside, the main active compound of Rhodiola plants, inhibits high glucose-induced mesangial cell proliferation.

    abstract::Because Rhodiola plants are known to have a protective effect on diabetic nephropathy, this study aimed to investigate the inhibitory effect of salidroside, the main active component of Rhodiola plants, on high glucose-induced mesangial cell proliferation and its possible mechanism. Salidroside (1 approximately 100 mi...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0029-1185717

    authors: Yin D,Yao W,Chen S,Hu R,Gao X

    更新日期:2009-09-01 00:00:00

  • Purification and biochemical characterization of a novel allergenic protein from tatary buckwheat seeds.

    abstract::An allergenic protein from tatary buckwheat seeds, designated TBt, was purified by salting out, anion exchange chromatography and size exclusion chromatography (SEC). Analysis by sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) and SEC showed that the allergenic protein was composed of two subunits...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0028-1088319

    authors: Zhang X,Cui X,Li Y,Wang Z

    更新日期:2008-12-01 00:00:00

  • Drimane-type sesquiterpenes from Polygonum hydropiper.

    abstract::One new drimane-type sesquiterpenoid, 3 β-angeloyloxy-7-epifutronolide (1), and one new natural product, polygonumate (2), along with six known drimane-type sesquiterpenes [dendocarbin L (3), (+) winterin (4), (+) fuegin (5), changweikangic acid A (6), futronolide (7), and 7-ketoisodrimenin (8)] were isolated from the...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0030-1271178

    authors: Sultana R,Hossain R,Adhikari A,Ali Z,Yousuf S,Choudhary MI,Ali MY,Zaman MS

    更新日期:2011-11-01 00:00:00

  • Synergistic induction of 1,25-dihydroxyvitamin D(3)- and all-trans-retinoic acid-induced differentiation of HL-60 leukemia cells by yomogin, a sesquiterpene lactone from Artemisia princeps.

    abstract::Many anti-inflammatory agents are known to significantly enhance the terminal differentiation of some cancer cells such as leukemia cells. In this study, the effect of yomogin, a eudesmane sesquiterpene lactone isolated from Artemisia princeps with anti-inflammatory activity, was investigated in human promyelocytic le...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2002-34937

    authors: Kim SH,Kim TS

    更新日期:2002-10-01 00:00:00

  • 21-Methylmelianodiols from Poncirus trifoliata as inhibitors of interleukin-5 bioactivity in Pro-B cells.

    abstract::Interleukin (IL)-5 plays an important role in the progression of allergic inflammation. Here, we have isolated 21alpha-methylmelianodiol and 21beta-methylmelianodiol from Poncirus trifoliata (L.) Raf., a plant of the Rutaceae family, as the inhibitors of IL-5-dependent growth of Y16 pro-B cells by bioassay-guided frac...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2008-1034329

    authors: Lee IJ,Xu GH,Ju JH,Kim JA,Kwon SW,Lee SH,Han SB,Kim Y

    更新日期:2008-03-01 00:00:00

  • Inhibition of butyrylcholinesterase activity by some isoquinoline alkaloids.

    abstract::The inhibition of butyrylcholinesterase activity in human serum by protoberberine, benzophenanthridine and aporphine alkaloids as well as four model compounds has been studied. The mechanism of the inhibition is discussed on the basis of the different types of interaction of these compounds with butyrylcholinesterase ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-969916

    authors: Ulrichová J,Walterová D,Preininger V,Simánek V

    更新日期:1983-07-01 00:00:00

  • Compounds inhibiting prostaglandin synthesis isolated from Ipomoea pes-caprae.

    abstract::The crude extract (IPA) of the plant Ipomoea pes-caprae (L.) R. Br. showed an inhibitory effect on prostaglandin synthesis in vitro. Bioassay-guided separation of the extract led to the isolation of four active compounds: 2-hydroxy-4,4,7-trimethyl-1(4H)-naphthalenone (1), (-)-mellein (2), eugenol (3), and 4-vinyl-guai...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-960196

    authors: Pongprayoon U,Baeckström P,Jacobsson U,Lindström M,Bohlin L

    更新日期:1991-12-01 00:00:00

  • Effect of gomisin A in an immunologically-induced acute hepatic failure model.

    abstract::Guinea pigs were sensitized with trinitrophenylated liver macromolecular protein fraction (TNP-LP1) prepared by using sodium trinitrobenzenesulfonate of strong immunogenicity as the hapten and LP1 as the carrier protein. The administration of trinitrophenylated hepatocytes and lipopolysaccharide to these TNP-LP1-sensi...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-960006

    authors: Mizoguchi Y,Shin T,Kobayashi K,Morisawa S

    更新日期:1991-02-01 00:00:00

  • Variability in yield and composition of essential oil in Cymbopogon jawarancusa.

    abstract::Variability in the oil content in natural populations of Cymbopogon jawarancusa is discussed. Races rich in piperitone, phellandrene and other chemical constituents have been identified. The oil producing ability was largely genetic and showed heritability of 79.0 percent. ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-971731

    authors: Dhar AK,Thappa RK,Atal CK

    更新日期:1981-04-01 00:00:00

  • New aspects of DNA-based authentication of Chinese medicinal plants by molecular biological techniques.

    abstract::DNA technology provides a powerful tool to complement chemical analyses for authentication of Chinese medicinal plants and to ensure that herbal materials are not contaminated with ineffective or potentially harmful substitutes or adulterants. In the last two decades molecular biotechnology has provided sophisticated ...

    journal_title:Planta medica

    pub_type: 杂志文章,评审

    doi:10.1055/s-0030-1250519

    authors: Heubl G

    更新日期:2010-12-01 00:00:00

  • Hypouricemic action of scopoletin arising from xanthine oxidase inhibition and uricosuric activity.

    abstract::Scopoletin exhibited an immediate and dose-dependent hypouricemic effect after intraperitoneal administration (50, 100, 200 mg/kg) in hyperuricemic mice induced by potassium oxonate; however, it did not affect the serum uric acid level in normal mice at the tested doses. For exploring the involved mechanisms of action...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2005-837789

    authors: Ding Z,Dai Y,Wang Z

    更新日期:2005-02-01 00:00:00

  • Molecular Identification Based on Chloroplast Sequences and Anti-complementary Activity Comparison of Juniperus Samples from the Qinghai-Tibet Plateau.

    abstract::Juniperus (Cupressaceae, Pinales) plants are widely distributed in the Qinghai-Tibet Plateau of China. The leaves and twigs of at least 8 Juniperus species (J. pingii, J. pingii var. wilsonii, J. squamata, J. recurva var. coxii, J. saltuaria, J. indica, J. tibetica and J. convallium var. microsperma) have been used as...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/a-1194-0471

    authors: Yang YT,De J,Fu ZL,Wang XL,Chen DF,Xie H,Lu Y

    更新日期:2020-11-01 00:00:00

  • Aescin protection of human vascular endothelial cells exposed to cobalt chloride mimicked hypoxia and inflammatory stimuli.

    abstract::Human vascular endothelial cells (HUVECs) were exposed to CoCl2 as an in vitro model of hypoxia. Expression of VCAM-1 (vascular cell adhesion molecule), reduction of PECAM-1 (platelet endothelial cell adhesion molecule) and cytoskeletal changes without alterations in cell viability were observed. HUVECs were also expo...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2007-967118

    authors: Montopoli M,Froldi G,Comelli MC,Prosdocimi M,Caparrotta L

    更新日期:2007-03-01 00:00:00

  • Antiplatelet Effects of Flavonoids Mediated by Inhibition of Arachidonic Acid Based Pathway.

    abstract::Flavonoids, important components of human diet, have been claimed to possess a significant antiplatelet potential, in particular due to their effects on the arachidonic acid cascade. Due to variable and incomplete results, this study was aimed at delivering a detailed analysis of the effects of 29 structurally relevan...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-0035-1557902

    authors: Karlíčková J,Říha M,Filipský T,Macáková K,Hrdina R,Mladěnka P

    更新日期:2016-01-01 00:00:00

  • Intestinal immune system modulating polysaccharides from rhizomes of Atractylodes lancea.

    abstract::Hot water extract (ALR-0) of rhizomes of Atractylodes lanceo DC. was fractionated into MeOH-soluble fraction (ALR-1), supernatant fraction of EtOH precipitation (ALR-3 + 4), and crude polysaccharide fraction (ALR-5). Among these fractions, only ALR-5 showed potent stimulating activity for proliferation of bone marrow ...

    journal_title:Planta medica

    pub_type: 杂志文章

    doi:10.1055/s-2006-957564

    authors: Yu KW,Kiyohara H,Matsumoto T,Yang HC,Yamada H

    更新日期:1998-12-01 00:00:00