Phenylpropanoid glycosides from Rhodiola rosea.

Abstract:

:Rhodiola rosea L. (Golden Root) has been used for a long time as an adaptogen in Chinese traditional medicine and is reported to have many pharmacological properties. Along its known secondary metabolites tyrosol (1), salidroside (rhodioloside) (2), rosin (3), rosarin (4), rosavin (5), sachaliside 1 (6) and 4-methoxy-cinnamyl-O-beta-D-glucopyranoside (7), four compounds were isolated from aqueous methanol extract of the plant and identified as cinnamyl-(6'-O-beta-xylopyranosyl)-O-beta-glucopyranoside (8), 4-methoxy-cinnamyl-(6'-O-alpha-arabinopyranosyl)-O-beta-glucopyranoside (9), picein (10) and benzyl-O-beta-glucopyranoside (11) by UV, MS and NMR methods. Compounds 8 and 9 are new natural compounds whereas compounds 10 and 11 were isolated first time from R. rosea. Also the compounds 6 and 7 are isolated earlier only from the callus cultures of the plant but not from the differentiated plant.

authors

Tolonen A,Pakonen M,Hohtola A,Jalonen J

doi

10.1248/cpb.51.467

subject

Has Abstract

pub_date

2003-04-01 00:00:00

pages

467-70

issue

4

eissn

0009-2363

issn

1347-5223

journal_volume

51

pub_type

杂志文章
  • Synthesis of peptides mimicking chemokine receptor CCR5 and their inhibitory effects against HIV-1 infection.

    abstract::Peptides mimicking chemokine receptor CCR5 were synthesized and their anti-HIV-1 activities evaluated. Prepared compounds, especially a sulfated derivatives, showed significant anti-HIV-1 activities. Furthermore, a hybrid molecule linked to an N-carbomethoxycarbonyl-prolyl-phenylalanine (CPF) moiety had a greater effe...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.308

    authors: Konishi K,Ikeda K,Achiwa K,Hoshino H,Tanaka K

    更新日期:2000-02-01 00:00:00

  • Synthesis and structure-activity studies of a series of 1-oxa-8-azaspiro[4.5]decanes as M1 muscarinic agonists.

    abstract::2,8-Dimethyl-1-oxa-8-azaspiro[4,5]decan-3-one (17), designed by incorporating the tetrahydrofuran ring moiety of muscarone into an 8-azaspiro[4,5]decane skeleton, and related 1-oxa-8-azaspiro[4.5]decanes were synthesized and assessed as M1 muscarinic agonists for the symptomatic treatment of dementia of Alzheimer's ty...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.842

    authors: Tsukamoto S,Fujii M,Yasunaga T,Matsuda K,Wanibuchi F,Hidaka K,Furuya T,Tamura T

    更新日期:1995-05-01 00:00:00

  • Synthesis and biological activity of 5'-aminobenzoxazinorifamycin derivatives.

    abstract::Benzoxazinorifamycin reacted with various secondary amines to yield various 5'-substituted aminobenzoxazinorifamycin derivatives. The derivatives exhibited potent activities against gram-positive bacteria and mycobacteria. The antimicrobial activities of these compounds against Mycobacterium tuberculosis and Mycobacte...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2707

    authors: Yamane T,Hashizume T,Yamashita K,Hosoe K,Hidaka T,Watanabe K,Kawaharada H,Kudoh S

    更新日期:1992-10-01 00:00:00

  • Synthesis and anti-HIV-1 activity of new delavirdine analogues carrying arylpyrrole moieties.

    abstract::In our search for novel anti-human immunodeficiency virus (HIV)-1 agents, 14 delavirdine analogues were synthesized and evaluated as potential anti-HIV-1 agents in cell-based assays. Compound 1Aa exhibited potent and selective anti-HIV-1 activity in acutely infected MT4 cells, with effective concentration (EC50) value...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1406

    authors: Pinna GA,Loriga G,Murineddu G,Grella G,Mura M,Vargiu L,Murgioni C,La Colla P

    更新日期:2001-11-01 00:00:00

  • Curcumin Inhibits Chondrocyte Hypertrophy of Mesenchymal Stem Cells through IHH and Notch Signaling Pathways.

    abstract::Using tissue engineering technique to repair cartilage damage caused by osteoarthritis is a promising strategy. However, the regenerated tissue usually is fibrous cartilage, which has poor mechanical characteristics compared to hyaline cartilage. Chondrocyte hypertrophy plays an important role in this process. Thus, i...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00225

    authors: Cao Z,Dou C,Dong S

    更新日期:2017-01-01 00:00:00

  • New friedelane triterpenoids with antimicrobial activity from the stems of Drypetes paxii.

    abstract::Two new friedelane-type triterpenes named 12alpha-hydroxyfriedelane-3,15-dione and 3beta-hydroxyfriedelan-25-al, together with six known compounds were isolated from the stems of Drypetes paxii Hutch. (Euphorbiaceae). Their structures were established on the basis of conventional 1 dimensional (1D) NMR methods, 2D shi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1119

    authors: Chiozem DD,Trinh-Van-Dufat H,Wansi JD,Mbazoa Djama C,Fannang VS,Seguin E,Tillequin F,Wandji J

    更新日期:2009-10-01 00:00:00

  • Acacia concinna saponins. I. Structures of prosapogenols, concinnosides A-F, isolated from the alkaline hydrolysate of the highly polar saponin fraction.

    abstract::A highly polar saponin mixture from pods of Acacia concinna (Leguminosae) was hydrolyzed with alkali to yield five new triterpenoidal prosapogenols named concinnosides A (6), B (3), C (7), D (4), and E (8), together with four known glycosides, acaciaside, (2), julibroside A1 (10) julibroside A3 (9), albiziasaponin C (...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.620

    authors: Abul Gafur M,Obata T,Kiuchi F,Tsuda Y

    更新日期:1997-04-01 00:00:00

  • Novel hypotensive peptides from the body of Elaphe climacophora.

    abstract::Four hypotensive peptides called elapherine-A, -B, -C and -D were isolated from the body of Elaphe climacophora after removal of the internal organs. Elapherine-A, which had the lowest molecular weight, exhibited a prolonged fall for 5 min in the blood pressure of spontaneously hypertensive rats, whereas elapherin-B, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1004

    authors: Tsujibo H,Sato H,Taniguchi T,Kamatani Y,Kenny PT,Nomoto K,Inamori Y

    更新日期:1990-04-01 00:00:00

  • Agents for the treatment of overactive detrusor. IX. Synthesis and pharmacological properties of metabolites of N-tert-Butyl-4,4-diphenyl-2-cyclopentenylamine (FK584) in human urine.

    abstract::We synthesized the racemates of the five presumed metabolites (1b-f) of (S)-(--)-N-tert-butyl-4,4-diphenyl-2-cyclopentenylamine hydrochloride (FK584, S(--)-1a), a novel agent for the treatment of overactive detrusor syndrome, in order to confirm the structures of the metabolites and also to evaluate their inhibitory a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.1188

    authors: Taniguchi K,Miyao Y,Yamano K,Yamamoto T,Terai T,Kusunoki T,Tsubaki K,Shiokawa Y

    更新日期:1996-06-01 00:00:00

  • Cimiracemoside a: A new cyclolanostanol xyloside from the rhizome of Cimicifuga racemosa.

    abstract::A new 9,19-cyclolanostane-type triterpene xyloside (1), from the rhizomes of Cimicifuga racemosa, has been isolated together with four known saponins; cimiaceroside A, 25-O-methylcimigenol-3-O-beta-D-xylopyranoside, 27-deoxyactein and 23-O-acetylshengmanol-3-O-beta-D-xylopyranoside. The structure of the new compound w...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.425

    authors: Bedir E,Khan IA

    更新日期:2000-03-01 00:00:00

  • Antitumor agents. V. Synthesis and antileukemic activity of E-ring-modified (RS)-camptothecin analogues.

    abstract::Several E-ring-modified analogues of (RS)-camptothecin were synthesized by total synthesis via Friedländer condensation and evaluated for cytotoxicity and antitumor activity against P388 mouse leukemia cells. Among them, (RS)-20-deoxyamino-7-ethyl-10-methoxycamptothecin (25c) was found to be more active than (RS)-camp...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.683

    authors: Ejima A,Terasawa H,Sugimori M,Ohsuki S,Matsumoto K,Kawato Y,Yasuoka M,Tagawa H

    更新日期:1992-03-01 00:00:00

  • Junceols D-H, new polyoxygenated briaranes from sea whip gorgonian coral Junceella juncea (Ellisellidae).

    abstract::Chemical investigations on the sea whip gorgonian coral Junceella juncea have led to the isolation of five new 8-hydroxybriarane diterpenoids, junceols D-H (1-5). The structures of briaranes 1-5 were determined on the basis of spectroscopic methods and the methylenecyclohexane rings were found to exist in boat form in...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1276

    authors: Sung PJ,Pai CH,Hwang TL,Fan TY,Su JH,Chen JJ,Fang LS,Wang WH,Sheu JH

    更新日期:2008-09-01 00:00:00

  • Four new cycloartane glycosides from Thalictrum fortunei.

    abstract::Four new cycloartane glycosides were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The chemical structures of these new glycosides were elucidated as 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranosyl (22S,24Z)-cycloart-24-en-3beta,22,26-triol 26-O-beta-D-glucopyranoside, 3-O-beta-D-glucop...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.107

    authors: Zhang XT,Zhang LH,Ye WC,Zhang XL,Yin ZQ,Zhao SX,Yao XS

    更新日期:2006-01-01 00:00:00

  • Drug Discovery Researches on Modulators of Lysine-Modifying Enzymes Based on Strategic Chemistry Approaches.

    abstract::Enzymatic and post-translational modifications (PTMs) such as ubiquitination, acetylation, and methylation occur at lysine residues. The PTMs play critical roles in the regulation of the protein functions, and thus, various cellular processes. In addition, aberrations of the PTMs are associated with various diseases, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c19-00741

    authors: Itoh Y

    更新日期:2020-01-01 00:00:00

  • Studies on the preparation of bioactive lignans by oxidative coupling reaction. III. Synthesis of polyphenolic benzofuran and coumestan derivatives by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate and their inhibitory e

    abstract::Three dihydrobenzofuran derivatives 11, 19, 22, a Pummerer's ketone 20 and a dimeric phenylpropanoid 24 were synthesized by oxidative coupling reaction of methyl (E)-3-(4-hydroxy-2-methoxyphenyl)propenoate 10, which was prepared from umbelliferone. The major product 11 was converted into its acetate 21 and schizotenui...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.2536

    authors: Maeda S,Masuda H,Tokoroyama T

    更新日期:1994-12-01 00:00:00

  • Minor saponins from Tetrapanax papyriferum.

    abstract::Four new minor saponins, papyrioside LE-LH, were isolated from the leaves of Tetrapanax papyriferum, and their structures were determined on the basis of spectroscopic evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.552

    authors: Mutsuga M,Kojima K,Saracoglu I,Ogihara Y

    更新日期:1997-03-01 00:00:00

  • Tannins and related polyphenols of euphorbiaceous plants. XI. Three new hydrolyzable tannins and a polyphenol glucoside from Euphorbia humifusa.

    abstract::Three new hydrolyzable tannins, euphormisins M1, M2, and M3, were isolated from Euphorbia humifusa WILLD., and respectively characterized as 1,3,6-tri-O-galloyl-4-O- brevifolincarboxyl-beta-D-glucose (19), an oxidative metabolite (23) of geraniin, and 1,3,6-tri-O-galloyl-alpha-D-glucose (18), by spectroscopic and chem...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.1803

    authors: Yoshida T,Amakura Y,Liu YZ,Okuda T

    更新日期:1994-09-01 00:00:00

  • 2-Acyl-3-carboxyl-tetrahydroisoquinoline Derivatives: Mixed-Type PTP1B Inhibitors without PPARγ Activation.

    abstract::A novel series of 2-acyl-3-carboxyl-tetrahydroisoquinoline derivatives were synthesized and biologically evaluated. Among them, (S)-2-{(E)-3-furan-2-ylacryloyl}-7-[(2E,4E)-5-(2,4,6-trifluorophenyl)penta-2,4-dienyloxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (compound 17u) was identified as a potent protein ty...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00571

    authors: Morishita K,Shoji Y,Fukui M,Ito Y,Kitao T,Ozawa SI,Hirono S,Shirahase H

    更新日期:2018-01-01 00:00:00

  • Tricalysionoside A, a megastigmane gentiobioside, sulfatricalysines A-F, and tricalysiosides X-Z, ent-kaurane glucosides, from the leaves of Tricalysia dubia.

    abstract::Further isolation work on the water-soluble fraction of a MeOH extract of Tricalysia dubia afforded one new megastigmane gentiobioside, named tricalysionoside A (1), and three sulfates, named sulfatricalysines A-C (2-4). Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of T. dubia yielded sulf...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.72

    authors: Shitamoto J,Sugimoto S,Matsunami K,Otsuka H,Shinzato T,Takeda Y

    更新日期:2011-01-01 00:00:00

  • Plasma-polymerized allylamine film used as a new solid phase in immunoradiometric assay (IRMA): effect of antibody (F(ab')2 fragment) concentration on dose response in two-site IRMA.

    abstract::Allylamine (ALAM) film was plasma-polymerized on a flat glass (referred to as ALAM(GLA): GLA refers to a flat glass plate) for use as a solid phase in two-site immunoradiometric assay (two-site IRMA). Adsorption of F(ab')2 anti-human immunoglobulin G [formula: see text] to ALAM(GLA) was larger than adsorption on a pol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.501

    authors: Muratsugu M,Kurosawa S,Mori Y,Kamo N

    更新日期:1992-02-01 00:00:00

  • Structure-based design and synthesis of fluorescent PPARalpha/delta co-agonist and its application as a probe for fluorescent polarization assay of PPARdelta ligands.

    abstract::Based on the result of X-ray crystallographic analysis of our peroxisome proliferator-activated receptor alpha and delta (PPARalpha/delta) co-agonist complexed with human PPAR ligand binding domain (LBD), we designed and synthesized an optically active fluorescent PPARalpha/delta co-agonist, which has a pyrene unit in...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1357

    authors: Araya Y,Kasuga J,Toyota K,Hirakawa Y,Oyama T,Makishima M,Morikawa K,Hashimoto Y,Miyachi H

    更新日期:2008-09-01 00:00:00

  • Taste masking of propiverine hydrochloride by conversion to its free base.

    abstract::The aim of the present study was to mask the bitterness of propiverine hydrochloride (P-4) by converting it to propiverine free base. Fine granules comprising the free base, which was converted from P-4 by desalination, were prepared. By using Fourier transform infrared spectroscopy, thermogravimetry-differential ther...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00206

    authors: Ogata T,Koide A,Kinoshita M,Ozeki T

    更新日期:2012-01-01 00:00:00

  • An effective synthesis of 5,4'-disubstituted flavones via a cesium enolate assisted intramolecular ipso-substitution reaction.

    abstract::A variety of 5,4'-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1107

    authors: Matsugi M,Takeda M,Takahashi A,Tazaki T,Tamura H,Shioiri T

    更新日期:2010-08-01 00:00:00

  • Synthesis and evaluation of (piperidinomethylene)bis(phosphonic acid) derivatives as anti-osteoporosis agents.

    abstract::Some (piperidinomethylene)bis(phosphonic acid) derivatives were prepared and their activity to inhibit a rise in serum calcium induced by parathyroid hormone in thyroparathyroidectomised rats was evaluated. Several (4-alkylidene-, 4,4-dialkyl-, or 4-alkyl-4-halopiperidinomethylene)bis(phosphonic acid) derivatives show...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1971

    authors: Mimura M,Hayashida M,Nomiyama K,Ikegami S,Iida Y,Tamura M,Hiyama Y,Ohishi Y

    更新日期:1993-11-01 00:00:00

  • Pyridonecarboxylic acids as antibacterial agents. VII. Synthesis and structure-activity relationship of amino- and hydroxyl-substituted 7-cycloalkyl and 7-vinyl derivatives of 1-cyclopropyl-6-fluoro-4-quinolone-3- carboxylic acid.

    abstract::Novel C(7)-derivatives of 1-cyclopropyl-6-fluoro-4-quinolone carboxylic acid (3a-o) have been synthesized and evaluated for in vitro antibacterial activity. Compounds 3e (3-aminocyclobutyl), 3g (1-aminocyclopropyl), 3m ((2-aminomethyl)vinyl), and 3o ((1-aminomethyl)vinyl) showed significant inhibitory activity, compar...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.42.2055

    authors: Todo Y,Nitta J,Miyajima M,Fukuoka Y,Ikeda Y,Yamashiro Y,Saikawa I,Narita H

    更新日期:1994-10-01 00:00:00

  • New fatty monoesters of erythromycin A.

    abstract::New fatty polyenic (linoleic, linolenic, arachidonic, linoelaidic) mono esters of erythromycin A have been synthesized by using various reagents such as acyl chloride, carboxylic acid anhydride, and mixed carbonic anhydride. These different ways of activating the fatty acid allowed a regioselectivity of esterification...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1672

    authors: Philippe M,Campos A,Sebag H,Rougier A,Dupuis D,Saint-Leger D,Vanlerberghe G

    更新日期:1990-06-01 00:00:00

  • Biotransformation of a taxadiene by ginkgo cell cultures and the tumor multi-drug resistant reversal activities of the metabolites.

    abstract::The biotransformation of 2α,5α,10β-triacetoxy-14-oxo-taxa-4(20),11-diene (1) by cultured Gingko cells afforded four products. Their structures were identified on the basis of analyses of the chemical and spectroscopic (IR, MS, ¹H- and ¹³C-NMR) data. Among them, 2, 3 and 5 were three new compounds, and 4 displayed pote...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1038

    authors: Xie D,Zhang Y,Zou J,Yin D,Chen X,Dai J

    更新日期:2011-01-01 00:00:00

  • Catalytic activity of anion-exchange resins modified with metal-porphine in oxidative reactions of phenols.

    abstract::Anion-exchange resins modified with metal-porphine (M-Pr) have been investigated to develop a solid catalyst in the oxidative reaction of phenols by O2 in air. Co-Pr, which is easily prepared and separable from the reaction mixture, has been proved to accelerate the oxidative reaction of phenols such as 3,5-di-tertbut...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1831

    authors: Iwado A,Mifune M,Kato J,Oda J,Chikuma M,Motohashi N,Saito Y

    更新日期:2000-11-01 00:00:00

  • Synthesis, structure and cytostatic activity of a series of N-substituted 3,4-diphenyl-1H-pyrrole-2,5-diones.

    abstract::A series of N-substituted 3,4-diphenyl-1H-pyrrole-2,5-diones (diphenylmaleimides) (IV) were synthesized and tested for cytostatic activity. Compounds IVa--k were prepared from diphenylmaleic anhydride or its dinitro derivative (V or VI) and the corresponding amine. Compounds IVl--n were obtained by reaction of 3-(p-ni...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2710

    authors: Fernández Braña M,Fernández A,Garrido M,López Rodríguez ML,Morcillo MJ,Sanz AM

    更新日期:1989-10-01 00:00:00

  • Benzylidene 2-aminoimidazolones derivatives: synthesis and in vitro evaluation of anti-tumor carcinoma activity.

    abstract::A series of benzylidene 2-aminoimidazolones derivatives were synthesized. Most compounds displayed strong inhibitory activity on the proliferation of human HepG2 cells in vitro. The active compounds were further evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay against five human ca...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00340

    authors: Ling Y,Wang ZQ,Xiao YA,Zhu C,Shen L,Wang XM,Hui Y,Wang XY

    更新日期:2013-01-01 00:00:00