A novel bufadienolide, marinosin, in the skin of the giant toad, Bufo marinus.

Abstract:

:We have identified a novel cardiac steroid, 11,19-epoxy-19-methoxytelocinobufagin, named marinosin (1), in the skin of the toad, Bufo marinus (L.) Schneider. The treatment of compound 1 with 50% CH3CN containing 0.1% trifluoroacetic acid yielded a 11 alpha-hydroxyhellebrigenin (2), which has not previously been isolated from animals or plants. The structures of both compounds were established from spectral data obtained by NMR and MS, which were compared with those of a reference bufadienolide, 11 alpha-hydroxytelocinobufagin. Compounds 1 and 2 have A/B cis and C/D cis configuration, which is characteristic of bufadienolides such as bufalin and marinobufagin. However, the stereo-structure of compound 1 was characterized by a boat form of the B ring, which is different from the chair form in typical bufadienolides such as compound 2. Compounds 1 and 2 both exhibited activity, as demonstrated by inhibition of Na+, K(+)-ATPase enzymatic activity and by inhibition of the binding of [3H]ouabain to Na+, K(+)-ATPase; however, marinosin (1) was as less effective inhibitor than 2, 11 alpha-hydroxyhellebrigenin. We have identified compound 2 in toad venom, but not in the skin.

authors

Matsukawa M,Akizawa T,Ohigashi M,Morris JF,Butler VP Jr,Yoshioka M

doi

10.1248/cpb.45.249

subject

Has Abstract

pub_date

1997-02-01 00:00:00

pages

249-54

issue

2

eissn

0009-2363

issn

1347-5223

journal_volume

45

pub_type

杂志文章
  • Amino acids and peptides. XXVII. Solid phase synthesis of fibrinogen-related peptides with disulfide bond formed on solid support.

    abstract::Fibrinogen-related peptides, monomeric cyclic peptides through a disulfide bond [cyclo(H-Cys-Arg-Gly-Asp-Phe-Cys-NH2), cyclo(H-Cys-Arg-Gly-Asp-Phe-Cys-Gly-NH2), cyclo(H-Cys-Arg-Gly-Asp-Cys-NH2) and cyclo(H-Cys-Arg-Gly-Asp-Cys-Gly-NH2)], were prepared by the solid phase method with disulfide bond formation on the solid...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.1107

    authors: Kakiuchi M,Izuno Y,Maeda M,Ueda K,Fujiwara K,Kunitada S,Kawasaki K

    更新日期:1996-05-01 00:00:00

  • Synthesis and antinociceptive activity of orally active opioid peptides: improvement of oral bioavailability by esterification.

    abstract::To improve the oral bioavailability of a dermorphin tetrapeptide analog, N(alpha)-1-iminoethyl-Tyr-D-MetO-Phe-MebetaAla-OH (III), which has a potent analgesic activity after oral administration, various derivatives were synthesized to increase lipophilicity by esterification of the C-terminal carboxyl group and/or acy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.759

    authors: Ogawa T,Araki M,Miyamae T,Okayama T,Hagiwara M,Sakurada S,Morikawa T

    更新日期:2003-07-01 00:00:00

  • Biochemical and partial molecular characterization of bitter and sweet forms of Lupinus angustifolius, an experimental model for study of molecular regulation of quinolizidine alkaloid biosynthesis.

    abstract::The bitter and sweet forms of a plant species differing with alkaloid contents may provide a model system for investigation of alkaloid biosynthesis at a molecular level. The pattern and concentration of quinolizidine alkaloids were determined by capillary GC-MS in bitter and sweet plants of Lupinus angustifolius. Bit...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1458

    authors: Hirai MY,Suzuki H,Yamazaki M,Saito K

    更新日期:2000-10-01 00:00:00

  • Studies on orally active cephalosporin esters. III. Effect of the 3-substituent on the chemical stability of pivaloyloxymethyl esters in phosphate buffer solution.

    abstract::The effect of substituents at the C-3 position on the degradation kinetics of the pivaloyloxymethyl (POM) ester of delta 3 cephalosporin in phosphate buffer solution (pH 6-8) was investigated. In the degradation, the isomerization process to the delta 2 ester was the rate-determining step. In this study, the logarithm...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.2375

    authors: Miyauchi M,Kurihara H,Fujimoto K,Kawamoto I,Ide J,Nakao H

    更新日期:1989-09-01 00:00:00

  • The new method for introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one and its application to chiral Wieland-Miescher type compound synthesis.

    abstract::The stereoselective introduction of an allyl group into the angular position of 2-(TBS-oxymethyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one was accomplished using Birch reduction and an enolate trapping reaction. It was determined that the allyl group was introduced via an unexpected conformation-flipped from the initi...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.207

    authors: Hiroya K,Takahashi T,Shimomae K,Sakamoto T

    更新日期:2005-02-01 00:00:00

  • Secondary metabolites from Andrographis paniculata.

    abstract::Two new flavonoid glycosides, 5-hydroxy-7,8-dimethoxy (2R)-flavanone-5-O-beta-D-glucopyranoside (1) and 5-hydroxy-7,8,2',5'-tetramethoxy-flavone-5-O-beta-D-glucopyranoside (2), and a new diterpenoid, andrographic acid (3), along with andrographidine A (4) were isolated from Andrographis paniculata, and their structure...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.455

    authors: Li W,Xu X,Zhang H,Ma C,Fong H,van Breemen R,Fitzloff J

    更新日期:2007-03-01 00:00:00

  • Amino acids and peptides. XIII. Synthetic studies on N-terminal tripeptide amide analogs of fibrin alpha-chain.

    abstract::N-Terminal tripeptide analogs of fibrin alpha-chain were synthesized and their inhibitory effect on fibrinogen/thrombin clotting was examined. A new water-soluble active ester, 3-pyridinium ester, was used for the synthesis. Among the synthetic peptides, H-Gly-Pro-Arg-hexamethyleneimine exhibited the highest inhibitor...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.584

    authors: Kawasaki K,Tsuji T,Hirase K,Miyano M,Imoto Y,Iwamoto M

    更新日期:1991-03-01 00:00:00

  • Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by flavonoids from licorice roots and 4-arylcoumarins.

    abstract::Isoliquiritigenin, glabridin, licoarylcoumarin and licoricidin were identified as strong inhibitors of adenosine 3',5'-cyclic monophosphate (cAMP) phosphodiesterase in waste materials which were obtained during the industrial extraction of glycyrrhizin from licorice roots. The structure-activity relationships of 12 fl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.930

    authors: Kusano A,Nikaido T,Kuge T,Ohmoto T,Delle Monache G,Botta B,Botta M,Saitoh T

    更新日期:1991-04-01 00:00:00

  • "One-pot" synthesis and antimalarial activity of formamidine derivatives of 4-anilinoquinoline.

    abstract::Amodiaquine (AQ) is an antimalarial which is effective against chloroquino-resistant strains of Plasmodium falciparum but whose clinical use is severely restricted because of associated hepatotoxicity and agranulocytosis. "One-pot" synthesis of formamidines likely to be transformed into AQ derivatives is reported. Com...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.933

    authors: Delarue S,Girault S,Dali Ali F,Maes L,Grellier P,Sergheraert C

    更新日期:2001-08-01 00:00:00

  • MRI Monitoring of the Mixed State of Admixtures Consisting of Moisturizing Cream and Steroid Ointment during the Mixing Process by a Revolution/Rotation-Type Hybrid Mixer.

    abstract::The admixture of a steroid ointment and a moisturizing cream is frequently prescribed to patients suffering from atopic dermatitis. For the mixing operation, a revolution/rotation-type hybrid mixer is widely used in pharmacy. The purpose of this study was to monitor the mixed state of the admixtures during the mixing ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00490

    authors: Yokokawa M,Setoyama H,Okada K,Hayashi Y,Machida Y,Onuki Y,Obata Y

    更新日期:2018-01-01 00:00:00

  • Regioselective intramolecular [3+2] annulation of allene-nitrones.

    abstract::The regioselective intramolecular 1,3-dipolar cycloaddition of the phenylsulfonylallene-nitrone derivatives has been developed. This reaction showed that the distal double bond of the allene exclusively reacted with the nitrone group to produce the bicyclic isoxazolidine derivatives regardless of the substitution patt...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.381

    authors: Inagaki F,Kobayashi H,Mukai C

    更新日期:2012-01-01 00:00:00

  • Studies on topical antiinflammatory agents. II. Synthesis and vasoconstrictive activity of 21-substituted corticosteroids with sulfur-containing moieties.

    abstract::As part of the search for new topical antiinflammatory agents, various 21-substituted corticosteroids having sulfur-containing moieties were prepared and tested for vasoconstrictive activity in humans. A structure-activity relationship study revealed that substitution of the 21-hydroxy group with a lower alkyl-thio gr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1795

    authors: Mitsukuchi M,Ikemoto T,Taguchi M,Higuchi S,Abe S,Yasui H,Hatayama K,Sota K

    更新日期:1989-07-01 00:00:00

  • A chemical approach to searching for bioactive ingredients in cigarette smoke.

    abstract::Cigarette smoke, a collection of many toxic chemicals, contributes to the pathogenesis of smoking-related diseases such as chronic obstructive pulmonary disease and cancer. Much work has been done on the chemical analysis of ingredients in cigarette smoke, but there are few reports on the active ingredients that can m...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00539

    authors: Takahashi Y,Horiyama S,Honda C,Suwa K,Nakamura K,Kunitomo M,Shimma S,Toyoda M,Sato H,Shizuma M,Takayama M

    更新日期:2013-01-01 00:00:00

  • Synthesis, characterization, cytotoxic activities, and DNA-binding studies of ternary copper(II) complexes with new coumarin derivatives.

    abstract::In this study, two novel complexes [Cu(MCVH)phen(H(2)O)].ClO(4) (1) and [Cu(MCLH)phen(H(2)O)].ClO(4) (2) (here, MCVH(2)=(7-hydroxy-4-methyl-8-coumarinyl) valine, MCLH(2)=(7-hydroxy-4-methyl-8-coumarinyl) leucine) have been synthesized and characterized by elemental analyses, molar conductance, infrared spectra (IR), (...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1003

    authors: Jia L,Xu XM,Xu J,Chen LH,Jiang P,Cheng FX,Lu GN,Wang Q,Wu JC,Tang N

    更新日期:2010-08-01 00:00:00

  • Steroidal glycosides from the fruits of Solanum viarum.

    abstract::Three new steroidal glycosides, named solaviasides A, B, and C, have been isolated from the fruits of Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae), along with seven known ones. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.632

    authors: Ono M,Kakiuchi T,Ebisawa H,Shiono Y,Nakamura T,Kai T,Ikeda T,Miyashita H,Yoshimitsu H,Nohara T

    更新日期:2009-06-01 00:00:00

  • Enzyme immunoassay for the drug of anti-ulcer using avidin-biotin system.

    abstract::We have developed a competitive enzyme immunoassay for a drug, which was a newly synthesized anti-ulcer agent, using an enzyme immunoassay. The polyclonal anti-drug antibody coupled to biotin, peroxidase labeled drug derivatives as a tracer, and a small column of Sepharose 4B covalently bound to avidin were used in th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.1779

    authors: Okumura T,Asano T,Adachi T,Hirano K

    更新日期:1991-07-01 00:00:00

  • Rupestines F-M, new guaipyridine sesquiterpene alkaloids from Artemisia rupestris.

    abstract::Eight new guaipyridine sesquiterpene alkaloids, rupestines F-M (1-8) were isolated from the leaves of Artemisia rupestris and their structures were elucidated on the basis of 2D-NMR data. The absolute configurations of 1-8 have been assigned by comparison of their experimental and calculated circular dichroism (CD) sp...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.60.213

    authors: He F,Nugroho AE,Wong CP,Hirasawa Y,Shirota O,Morita H,Aisa HA

    更新日期:2012-01-01 00:00:00

  • On the interaction of doxorubicin with oleate ions: fluorescence spectroscopy and liquid-liquid extraction study.

    abstract::Increase of lipophilicity of cationic doxorubicin (DOX) by its association with a fatty acid ion is of interest for pharmaceutical formulations and could have an impact on the drug delivery into cancer cells. On the basis of spectroscopic analysis of intrinsic DOX fluorescence, this study provides an experimental evid...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1006

    authors: Munnier E,Tewes F,Cohen-Jonathan S,Linassier C,Douziech-Eyrolles L,Marchais H,Soucé M,Hervé K,Dubois P,Chourpa I

    更新日期:2007-07-01 00:00:00

  • Oplopanphesides A-C, three new phenolic glycosides from the root barks of Oplopanax horridus.

    abstract::Three new phenolic glycosides, named oplopanphesides A-C (1-3), have been isolated from the root barks of Oplopanax horridus. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR techniques. These phenolic glycosides possess a novel feature in their sugar moieties that ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.676

    authors: Huang WH,Zhang QW,Meng LZ,Yuan CS,Wang CZ,Li SP

    更新日期:2011-01-01 00:00:00

  • Use of Phthalimidoacetyl Isothiocyanate as a Scaffold in the Synthesis of Target Heterocyclic Systems, and Their Antimicrobial Assessment.

    abstract::Phthalimidoacetyl isothiocyanate underwent addition-cyclization reactions with some nitrogen and carbon nucleophilic reagents. Simultaneous or subsequent cyclization of the obtained adducts gave target heterocyclic systems such as 1,2,4-triazoles, 1,3-diazines, 1,3-oxazines and thiourea attached to a phthalimido moiet...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00099

    authors: Hemdan MM,El-Sayed AA

    更新日期:2016-01-01 00:00:00

  • Cytotoxicity of asymmetric platinum complexes against L-1210 cells. Effect of bulky substituents.

    abstract::The asymmetric platinum complexes cis-Pt(LL')Cl2 (L = NH3, L' = CH3NH2, (CH3)2NH, C2H5NH2 and (C2H5)2NH and LL' = N,N-dimethylethylenediamine),--one of the NH3 groups of cis-Pt(NH3)2Cl2 was substituted by alkylamine--, were synthesized and their cytotoxic effects have been measured using L-1210 cells. The IC50 values ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2850

    authors: Hirano T,Inagaki K,Fukai T,Alink M,Nakahara H,Kidani Y

    更新日期:1990-10-01 00:00:00

  • Structural Optimization of Ghrelin Receptor Inverse Agonists to Improve Lipophilicity and Avoid Mechanism-Based CYP3A4 Inactivation.

    abstract::Structural optimization of 2-aminonicotinamide derivatives as ghrelin receptor inverse agonists is reported. So as to avoid mechanism-based inactivation (MBI) of CYP3A4, 1,3-benzodioxol ring of the lead compound was modified. Improvement of the main activity and lipophilicity was achieved simultaneously, leading to co...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00285

    authors: Takahashi B,Funami H,Shibata M,Maruoka H,Koyama M,Kanki S,Muto T

    更新日期:2015-01-01 00:00:00

  • A novel, bio-reducible gene vector containing arginine and histidine enhances gene transfection and expression of plasmid DNA.

    abstract::We have engineered a novel, non-viral, multifunctional gene vector (STR-CH(2)R(4)H(2)C) that contained stearoyl (STR) and a block peptide consisting of Cys (C), His (H), and Arg (R). STR-CH(2)R(4)H(2)C can form a stable nano-complex with plasmid DNA (pDNA) based on electronic interactions and disulfide cross linkages....

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.202

    authors: Tanaka K,Kanazawa T,Ogawa T,Suda Y,Takashima Y,Fukuda T,Okada H

    更新日期:2011-01-01 00:00:00

  • Synthesis and evaluation of pyrrolin-2-one compounds, a series of plasminogen activator inhibitor-1 inhibitors.

    abstract::A novel series of furan-2-one and pyrrolin-2-one derivatives having PAI-1 (plasminogen activator inhibitor-1) inhibitory activity were synthesized and evaluated for their antithrombotic activity in a rat arterial thrombosis model. Among the synthesized compounds, 5f (T-1776Na) was found to have good selectivity for PA...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.979

    authors: Miyazaki H,Ogiku T,Sai H,Moritani Y,Ohtani A,Ohmizu H

    更新日期:2009-09-01 00:00:00

  • Design, Synthesis and Antiproliferative Evaluation of Novel Disulfides Containing 1,3,4-Thiadiazole Moiety.

    abstract::A series of novel disulfides containing 1,3,4-thiadiazole moiety were designed, synthesized, and the structures of all products were identified by spectral data (IR, NMR, and high resolution (HR)-MS). Their in vitro antiproliferative activities were evaluated using 2-(2-methoxy-4-nitro-phenyl)-3-(4-nitro-phenyl)-5-(2,...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00485

    authors: Zhang S,Liu XJ,Tang R,Wang HX,Liu HY,Liu YM,Chen BQ

    更新日期:2017-01-01 00:00:00

  • Screening and Characterization of Hydrate Forms of T-3256336, a Novel Inhibitor of Apoptosis (IAP) Protein Antagonist.

    abstract::Different crystal packing of hydrates from anhydrate crystals leads to different physical properties, such as solubility and stability. Investigation of the potential of varied hydrate formation, and understanding the stability in an anhydrous/hydrate system, are crucial to prevent an undesired transition during the m...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00262

    authors: Takeuchi S,Kojima T,Hashimoto K,Saito B,Sumi H,Ishikawa T,Ikeda Y

    更新日期:2015-01-01 00:00:00

  • Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates.

    abstract::Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxy...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00122

    authors: Yasui E,Tsuda J,Ohnuki S,Nagumo S

    更新日期:2016-01-01 00:00:00

  • Spectroscopic, thermal and biological studies of the coordination compounds of sulfasalazine drug: Mn(II), Hg(II), Cr(III), ZrO(II), VO(II) and Y(III) transition metal complexes.

    abstract::The complexations of sulfasalazine (H3Suz) with some of transition metals have been investigated. Three types of complexes, [Mn(HSuz)-2(H2O)4] x 2H2O, [M(HSuz)-2(H2O)2] x xH2O (M=Hg(II), ZrO(II) and VO(II), x=4, 8 and 6, respectively) and [M(HSuz)-2(Cl)(H2O)3] x xH2O (M=Cr(III) and Y(III), x=5 and 6, respectively) wer...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1585

    authors: El-Wahed MG,Refat MS,El-Megharbel SM

    更新日期:2008-11-01 00:00:00

  • Identification of indoline-2-thione analogs as novel potent inhibitors of α-melanocyte stimulating hormone induced melanogenesis.

    abstract::Based on the hits, 3,4-dihydroquinazoline-2-thione (1) and benzimidazole-2-thione (2), a series of indole-2-thione (3) and indole-2-thiol inhibitors (4) of melanogenesis were designed, synthesized and evaluated in melanoma B16 cells under the stimulant of α-melanocyte stimulating hormone (α-MSH). The indole-2-thione c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.1285

    authors: Thanigaimalai P,Lee KC,Sharma VK,Sharma N,Roh E,Kim Y,Jung SH

    更新日期:2011-01-01 00:00:00

  • Synthesis, antitumor, antitrypanosomal and antileishmanial activities of benzo[4,5]canthin-6-ones bearing the N'-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide groups at C-2.

    abstract::A series of novel benzo[4,5]canthin-6-ones, bearing the N'-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and antileishmanial act...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00356

    authors: Leite Silva CM,Garcia FP,Rodrigues JH,Nakamura CV,Ueda-Nakamura T,Meyer E,Ruiz AL,Foglio MA,de Carvalho JE,da Costa WF,Sarragiotto MH

    更新日期:2012-01-01 00:00:00