Three new naphthoquinone derivatives from Diospyros maritima Blume.

Abstract:

:Three new naphthoquinone derivatives, 6-(1-ethoxyethyl)plumbagin (16), ethylidene-3,3'-biplumbagin (17), and ethylidene-3,6'-biplumbagin (18), were isolated, in addition to six known naphthoquinones, isozeylanone (10), 3,3'-biplumbagin (11), chitranone (12), methylene-3,3'-biplumbagin (13), 2,3-epoxyplumbagin (14), and 3,8'-biplumbagin (15), from the fruits of Diospyros maritima Blume (Ebenaceae). The structures of the new compounds were established by spectroscopic methods. The eight naphthoquinones 11-18 were examined for ichthyotoxic activity and germination inhibitory activity. The quinones 11, 12, and 14-16 showed strong ichthyotoxic activity and the quinone 14 mild germination inhibitory activity.

authors

Higa M,Noha N,Yokaryo H,Ogihara K,Yogi S

doi

10.1248/cpb.50.590

subject

Has Abstract

pub_date

2002-05-01 00:00:00

pages

590-3

issue

5

eissn

0009-2363

issn

1347-5223

journal_volume

50

pub_type

杂志文章
  • Structure-Activity Relationship Study on Col-003, a Protein-Protein Interaction Inhibitor between Collagen and Hsp47.

    abstract::This study demonstrates the structure-activity relationship of Col-003, a potent collagen-heat-shock protein 47 (Hsp47) interaction inhibitor. Col-003 analogues were successfully synthesized by Pd(0)-catalyzed cross-coupling reactions of 5-bromosalicylaldehyde derivatives with alkyl-metal species, and the inhibitory a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c19-00634

    authors: Yoshida M,Saito M,Ito S,Ogawa K,Goshima N,Nagata K,Doi T

    更新日期:2020-03-01 00:00:00

  • Application of the solid dispersion method to the controlled release of medicine. IV. Precise control of the release rate of a water soluble medicine by using the solid dispersion method applying the difference in the molecular weight of a polymer.

    abstract::Solid dispersions were prepared by the evaporation of ethanol after dissolving into ethanol a water soluble medicine (oxprenolol hydrochloride (OXP)), four grades of water insoluble ethylcellulose (EC) and four grades of water soluble hydroxypropyl cellulose (HPC), both having different molecular weights. The precise ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.933

    authors: Yuasa H,Ozeki T,Kanaya Y,Oishi K

    更新日期:1993-05-01 00:00:00

  • New abietane and seco-abietane diterpenes from the roots of Taiwania cryptomerioides.

    abstract::Four new diterpenes, 3-oxosaprorthoquinone (1), 3-oxomicrostegiol (2), 3-oxoisotaxodione (3), and taiwaninal (4), together with two known compounds, 3-oxosapriparaquinone (5) and 6-dehydrohinokiol (6), were isolated from the roots of Taiwania cryptomerioides. The structures of 1-4 were principle elucidated based on sp...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.11

    authors: Chyu CF,Lin HC,Kuo YH

    更新日期:2005-01-01 00:00:00

  • Absolute Structures of Wedelolide Derivatives and Structure-Activity Relationships of Protein Tyrosine Phosphatase 1B Inhibitory ent-Kaurene Diterpenes from Aerial Parts of Wedelia spp. Collected in Indonesia and Japan.

    abstract::Two sesquiterpene lactones with the (9R)-eudesman-9,12-olide framework, wedelolides I and J, have been isolated together with five eudesmanolide sesquiterpenes and twelve ent-kaurene diterpenes from the aerial parts of Indonesian Wedelia prostrata. The absolute configurations of wedelolides I and J, proposed in the pr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00117

    authors: Abdjul DB,Yamazaki H,Kanno SI,Kirikoshi R,Tomizawa A,Takahashi O,Maarisit W,Losung F,Rotinsulu H,Wewengkang DS,Sumilat DA,Kapojos MM,Namikoshi M

    更新日期:2018-01-01 00:00:00

  • Cycloartane glycosides from Cimicifuga dahurica.

    abstract::A new cycloartane bisdesmoside and two new trinorcycloartane glycosides, along with four known cycloartane compounds, were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae). The structures of the new compounds were elucidated as 3-O-alpha-L-arabinopyranosyl cimigenol 15-O-beta-D-glucopyranoside, 24-hyd...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1468

    authors: Zhang QW,Ye WC,Hsiao WW,Zhao SX,Che CT

    更新日期:2001-11-01 00:00:00

  • Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,β-Unsaturated Amide and Azomethine Imine.

    abstract::α,β-Unsaturated amides were incorporated as viable dipolarophiles in a catalytic asymmetric 1,3-dipolar cycloaddition of azomethine imines. The use of a 7-azaindoline auxiliary was essential to acquire sufficient reactivity with excellent diastereoselectivity, likely due to the chelating activation of the amide by the...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00130

    authors: Li Z,Kumagai N,Shibasaki M

    更新日期:2020-01-01 00:00:00

  • Microbial metabolites of harman alkaloids.

    abstract::Several microorganisms showed the ability to transform the harman alkaloids, harmaline (1), harmalol (2) and harman (5). Harmaline (1) and harmalol (2) were converted by Rhodotorula rubra ATCC 20129 into the tryptamines, 2-acetyl-3-(2-acetamidoethyl)-7-methoxyindole (3) and 2-acetyl-3-(2-acetamidoethyl)-7-hydroxyindol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.646

    authors: Herath W,Mikell JR,Ferreira D,Khan IA

    更新日期:2003-06-01 00:00:00

  • First synthesis of a alpha-trifluoromethyl allenol ether via the Julia-Lythgoe process.

    abstract::Alpha-trifluoromethyl allenol ethers 9a-e were prepared in moderate to good yields by the Julia-Lythgoe process using beta-ethoxy-beta-trifluoromethyl vinylic sulfone 3. Several reactions of 9c were examined to give alpha,beta-unsaturated trifluoromethyl ketone derivatives 11 and 12. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.1395

    authors: Yoshimatsu M,Hibino M

    更新日期:2000-09-01 00:00:00

  • Flavonol triglycosides from the leaves of Hammada scoparia (POMEL) ILJIN.

    abstract::A new flavonol triglycoside, isorhamnetin 3-O-beta-D-xylopyranosyl-(1"-->3)-alpha-L-rhamnopyranosyl-(1'''-->6")-beta-D-galactopyranoside, has been isolated from the leaves of Hammada scoparia together with two known compounds, isorhamnetin 3-O-beta-D-apiofuranosyl-(1'''-->2")[alpha-L-rhamnopyranosyl-(1"-->6")]-beta-D-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1268

    authors: Ben Salah H,Jarraya R,Martin MT,Veitch NC,Grayer RJ,Simmonds MS,Damak M

    更新日期:2002-09-01 00:00:00

  • Progress in Development of Interventions to Prevent Birth Defects in Diabetic Pregnancies.

    abstract::Diabetic embryopathy is a diabetic complication, in which maternal hyperglycemia in early pregnancy causes birth defects in newborn infants. Under maternal diabetic conditions, hyperglycemia disturbs intracellular molecular activities and organelles functions. These include protein misfolding in the endoplasmic reticu...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c18-01013

    authors: Han L,Jiang Z,Zheng X,Qiu J,Hu Y,Li X

    更新日期:2019-01-01 00:00:00

  • Enhancement of water solubility of fullerene by cogrinding with mixture of cycloamyloses, novel cyclic alpha-1,4-glucans, via solid-solid mechanochemical reaction.

    abstract::Improvement of solubility for fullerene (C60) was studied by cogrinding with cycloamyloses using a ball mill in the solid state. Cycloamylose is a novel cyclic alpha-1,4-glucan produced from synthetic amylose by enzymatic reaction. Although sample solutions showed a pale yellow for the initial period of cogrinding wit...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.961

    authors: Fukami T,Mugishima A,Suzuki T,Hidaka S,Endo T,Ueda H,Tomono K

    更新日期:2004-08-01 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

  • Nanoparticle formation of poorly water-soluble drugs from ternary ground mixtures with PVP and SDS.

    abstract::Poorly water-soluble drugs N-5159, griseofulvin (GFV), glibenclamide (GBM) and nifedipine (NFP) were ground in a dry process with polyvinylpyrrolidone (PVP) and sodium dodecyl sulfate (SDS). Different crystallinity behavior of each drug during grinding was shown in the ternary Drug/PVP/SDS system. However, when each t...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.171

    authors: Itoh K,Pongpeerapat A,Tozuka Y,Oguchi T,Yamamoto K

    更新日期:2003-02-01 00:00:00

  • Enzyme inhibitory constituents from Duranta repens.

    abstract::Isoprenylated flavonoids 5,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-3,6,4'-trimethoxyflavone (1), 3,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-5,6,4'-trimethoxyflavone (2) and an isoprenylated acetophenone derivative (3) have been isolated from Duranta repens along with known compounds, 5-hydroxy-3,6,7,4'-tetr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.515

    authors: Anis I,Ahmed S,Malik A,Yasin A,Choudary MI

    更新日期:2002-04-01 00:00:00

  • Effects of dehydration temperatures on moisture absorption and dissolution behavior of theophylline.

    abstract::Anhydrous theophylline was prepared by heating theophylline monohydrate at temperatures between 60 degrees C and 140 degrees C. The effects of dehydration temperatures on the moisture absorption and dissolution behavior of anhydrous theophylline were investigated in this study. The hydration rate of anhydrous theophyl...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1526

    authors: Ono M,Tozuka Y,Oguchi T,Yamamoto K

    更新日期:2001-12-01 00:00:00

  • Chiral Calcium-Catalyzed Asymmetric Epoxidation Reactions Using Hydrogen Peroxide as the Terminal Oxidant.

    abstract::Asymmetric epoxidation reactions of chalcone derivatives catalyzed by chiral calcium complexes using hydrogen peroxide were developed. The epoxidation reactions proceeded smoothly to afford the desired products in good yields with good enantioselectivities. This is the first example of chiral calcium-catalyzed asymmet...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00485

    authors: Yamashita Y,Macor JA,Fushimi S,Tsubogo T,Kobayashi S

    更新日期:2018-01-01 00:00:00

  • Amino acids and peptides. XXIX. Synthesis of peptide fragments related to active center of eglin c and studies on the relationship between their structure and their inhibitory activity against cathepsin G and alpha-chymotrypsin.

    abstract::H-Ser-Pro-Val-Thr-Leu-Asp-Leu-Arg-Tyr-OMe, corresponding to the sequence 41-49 of eglin c, inhibited human leukocyte cathepsin G and alpha-chymotrypsin. In order to gain further insight into the relationship between the structure and the inhibitory activity against cathepsin G and alpha-chymotrypsin, peptide fragments...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.3249

    authors: Nakabayashi K,Tsuboi S,Fujimoto T,Okada Y,Nagamatsu Y,Yamamoto J

    更新日期:1990-12-01 00:00:00

  • Fern constituents: dryocrassy formate, sitostanyl formate and 12alpha-hydroxyfern-9(11)-ene from Cyathea podophylla.

    abstract::Dryocrassyl formate, sitostanyl formate, and 12alpha-hydroxyfern-9(11)-ene were isolated from the fresh fronds of Cyathea podophylla. Their structures were elucidated by spectroscopic techniques and synthesis. Ten known triterpenoids, three derivatives of phytol, a stanol, and beta-tocopherol were also identified from...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1311

    authors: Arai Y,Hattori T,Hamaguchi N,Masuda K,Takano A,Shiojima K

    更新日期:2003-11-01 00:00:00

  • Synthesis, crystal structure, and DNA-binding study on the trinitrate{2,2'-[2,3-naphthylenebis(oxy)]-bis(N,N-diisopropyl(acetamide))} gadolinium(III) complex.

    abstract::A 2,2'-[2,3-naphthylenebis(oxy)]-bis(N,N-diisopropyl(acetamide)) ligand (L) and its Gd(III) complex have been prepared and characterized. The crystal and molecular structure of the complex was determined by single-crystal X-ray diffraction. The interactions of complex with calf thymus DNA were investigated by UV-vis, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1150

    authors: Lei K,Liu W,Huang X,Wang D

    更新日期:2006-08-01 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

  • Design of nateglinide controlled release tablet containing erosion matrix tablet and multiple administration study in normal beagle dogs.

    abstract::We designed a single unit type tablet formulation containing nateglinide to decrease both postprandial blood glucose level (PBG) and fasting blood glucose level (FBG) in normal beagle dogs. The tablet was a dry coated tablet comprising both a core tablet (an erosion matrix tablet: a controlled release portion(nateglin...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.907

    authors: Makino C,Sakai H,Okano A,Yabuki A

    更新日期:2009-09-01 00:00:00

  • Utility of 2-hydroxypropyl-beta-cyclodextrin in an intramuscular injectable preparation of nimodipine.

    abstract::Possible utility of hydroxyalkylated beta-cyclodextrin (beta-CyD) derivatives as parenteral drug carriers was investigated, using nimodipine, a dihydropyridine derivative with calcium antagonistic action, as a model drug. The aqueous solubility of nimodipine increased linearly with increase in the concentration of hyd...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.176

    authors: Yoshida A,Yamamoto M,Itoh T,Irie T,Hirayama F,Uekama K

    更新日期:1990-01-01 00:00:00

  • Pyrrole Oligoglycosides from the Starfish Acanthaster planci Suppress Lipopolysaccharide-Induced Nitric Oxide Production in RAW264.7 Macrophages.

    abstract::Two new pyrrole oligoglycosides, plancipyrrosides A and B (1 and 2), were isolated from methanol extract of the Vietnamese starfish Acanthaster planci using various chromatographic procedures. Their structures were elucidated by spectroscopic methods including one and two dimensional (1D- and 2D)-NMR and Fourier trans...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00585

    authors: Vien LT,Hanh TT,Huong PT,Dang NH,Thanh NV,Lyakhova E,Cuong NX,Nam NH,Kiem PV,Kicha A,Minh CV

    更新日期:2016-11-01 00:00:00

  • Synthesis of N-substituted piperazinyl carbamoyl and acetyl derivatives of tetrahydropapaverine: potent antispasmodic agents.

    abstract::The synthesis and structure-activity-relationship (SAR) for a series of N-substituted piperazinyl carbamoyl 7-15 and piperazinyl acetyl 18-26 derivatives of tetrahydropapaverine have been carried out. The general synthetic methods of carbamoyl tetrahydropapaverine analogues involve N-substituted piperazines and carbam...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.1223

    authors: Kaur J,Ghosh NN,Talwar A,Chandra R

    更新日期:2002-09-01 00:00:00

  • Fasciculic acids A, B and C as calmodulin antagonists from the mushroom Naematoloma fasciculare.

    abstract::Three new fasciculol esters, fasciculic acids A (1), B (2) and C (3), having potent calmodulin antagonistic activity were isolated from the toxic mushroom Naematoloma fasciculare (Fr.) Karst. Their structures were elucidated on the basis of spectral and chemical evidence. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.3247

    authors: Takahashi A,Kusano G,Ohta T,Ohizumi Y,Nozoe S

    更新日期:1989-12-01 00:00:00

  • Study on the reactivity of diarylmethane derivatives in supercritical alcohols media: reduction of diarylmethanols and diaryl ketones to diarylmethanes using supercritical 2-propanol.

    abstract::We found that diarylmethanols and diaryl ketones were smoothly reduced to the corresponding diarylalkanes using supercritical 2-propanol in good yields. Furthermore, we determined the specific reaction of fluorene using supercritical methanol at high temperature. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.1304

    authors: Hatano B,Kubo D,Tagaya H

    更新日期:2006-09-01 00:00:00

  • Quaternary isoquinoline alkaloids from Stephania cepharantha.

    abstract::From the quaternary alkaloidal fraction of the dried tubers of Stephania cepharantha, two new isoquinoline alkaloids, stecepharine and tetradehydroreticuline have been isolated along with the known compounds, magnoflorine, menisperine, steponine, cyclanoline, oblongine, cis-N-methylcapaurine and 2'-N-methylisotetrandr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.48.370

    authors: Tanahashi T,Su U,Nagakura N,Nayeshiro H

    更新日期:2000-03-01 00:00:00

  • Synthesis of 16 alpha-hydroxyandrost-4-ene-3,17,19-trione and 3 beta, 16 alpha-dihydroxyandrost-5-ene-17,19-dione; potential intermediates of estriol biosynthesis.

    abstract::16 alpha-Hydroxyandrost-4-ene-3,17,19-trione (10) was synthesized from the 16 alpha-hydroxy-6 beta,19-epoxy-17-one 3 via protection of the 16 alpha-hydroxy function as its tert-butyldimethylsilyl ether or acetate. Reductive cleavage of the epoxy ring of the silyl ether 4 or the acetate 5 with zinc dust gave the 19-alc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2040

    authors: Numazawa M,Hoshi K,Konno T,Nagaoka M

    更新日期:1990-07-01 00:00:00

  • 3-anilino-L-alanine, structural determination of UV-5, a contaminant in EMS-associated L-tryptophan samples.

    abstract::An aniline derivative which corresponds to UV-5 in the preceding paper was isolated from the case L-tryptophan sample associated with eosinophilia-myalgia syndrome (EMS). By spectroscopic analyses, the structure was identified as 3-anilinoalanine. The compound was optically active, and the stereochemistry of alanine m...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.40.2236

    authors: Goda Y,Suzuki J,Maitani T,Yoshihira K,Takeda M,Uchiyama M

    更新日期:1992-08-01 00:00:00

  • Development and validation of liquid chromatographic and UV derivative spectrophotometric methods for the determination of famciclovir in pharmaceutical dosage forms.

    abstract::A high-performance liquid chromatographic method and a UV derivative spectrophotometric method for the determination of famciclovir, a highly active antiviral agent, in tablets were developed in the present work. The various parameters, such as linearity, precision, accuracy, specificity, robustness, limit of detectio...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.819

    authors: Srinubabu G,Sudharani B,Sridhar L,Rao JS

    更新日期:2006-06-01 00:00:00