Seven-membered vibsane-type diterpenes with a 5,10-cis relationship from Viburnum awabuki.

Abstract:

:New five seven-membered vibsane-type diterpenes named 5-epi-vibsanin C, 5-epi-vibsanin H, 5-epi-vibsanin K, 18-O-methyl-5-epi-vibsanin K and 5-epi-vibsanin E have been isolated from the leaves of Viburnum awabuki (Caplifoliaceae). Their structures have been elucidated by analyses of spectroscopic data and comparison of their spectral data with those of the previously known seven-membered vibsane-type diterpenes. The occurrence of these seven-membered vibsane-type diterpenes with a cis relationship on the C-5 and C-10 positions in nature have been predicted by conformational analysis of vibsanin B, an eleven-membered vibsane-type diterpene. Vibsanin C, 5-epi-vibsanin C and 5-epi-vibsanin H exhibited moderate cytotoxic activities on KB cells.

authors

Fukuyama Y,Minami H,Matsuo A,Kitamura K,Akizuki M,Kubo M,Kodama M

doi

10.1248/cpb.50.368

subject

Has Abstract

pub_date

2002-03-01 00:00:00

pages

368-71

issue

3

eissn

0009-2363

issn

1347-5223

journal_volume

50

pub_type

杂志文章
  • Prediction of the stability of imipenem in intravenous mixtures.

    abstract::The purpose of this study was to predict the stability of imipenem in a mixed infusion. The hydrolysis of imipenem in aqueous solution was found to be accelerated by pH, and by increasing concentrations of sodium bisulfite (SBS) and L-cysteine. Equations were derived for the degradation rate constants (k(obs)) of pH, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00427

    authors: Yoshida M,Takasu Y,Shimizu K,Asahara K,Uchida T

    更新日期:2013-01-01 00:00:00

  • Product analyses of ozone mediated nitration of benzimidazole derivatives with nitrogen dioxide: formation of 1-nitrobenzimidazoles and conversion to benzotriazoles.

    abstract::Several benzimidazole derivatives having electron-withdrawing or -donating substituent(s) at the benzene moiety were used as models of the imidazole moiety of purine bases and their nitration with nitrogen dioxide and ozone (so-called Kyodai nitration) were examined. Products were extracted from the reaction mixture w...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.570

    authors: Kaiya T,Nakamura K,Tanaka M,Miyata N,Kohda K

    更新日期:2004-05-01 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

  • Studies on cardiotonic agents. II. Synthesis of novel phthalazine and 1,2,3-benzotriazine derivatives.

    abstract::A series of phthalazine and 1,2,3-benzotriazine derivatives which have heterocyclylpiperidino groups was synthesized and tested for cardiotonic activity in anesthetized dogs. Several 6,7-dimethoxyphthalazine derivatives showed relatively potent cardiotonic activity comparable to that of amrinone. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2179

    authors: Nomoto Y,Obase H,Takai H,Teranishi M,Nakamura J,Kubo K

    更新日期:1990-08-01 00:00:00

  • Synthesis of dibenzofurans directly from aryl halides and ortho-bromophenols via one-pot consecutive SNAr and intramolecular palladium-catalyzed aryl-aryl coupling reactions.

    abstract::A series of dibenzofurans were efficiently and conveniently synthesized via one-pot consecutive C(sp(2))-O bond formation reaction (SNAr) in the presence of anhydrous K(2)CO(3), followed by C(sp(2))-C(sp(2)) bond formation reaction (intramolecular palladium-catalyzed aryl-aryl coupling reaction) between aryl halides a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1496

    authors: Xu H,Fan LL

    更新日期:2008-10-01 00:00:00

  • Amino acids and peptides. XLIV. Synthesis of stereoisomeric pentapeptides of thiol proteinase inhibitor.

    abstract::Stereoisomers of thiol proteinase inhibitor (TPI) were synthesized by a conventional solution method. Among them, iNoc-D-Gln-Val-Val-Ala-Ala-pNA weakly inhibited the amidolytic activity of papain, although iNoc-Gln-Val-Val-Ala-Ala-pNA inhibited papain activity fairly potently. However, the other five D-amino acid-cont...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.1599

    authors: Iguchi S,Hirano K,Okamoto H,Okamoto Y,Okada Y

    更新日期:1996-08-01 00:00:00

  • Synthesis and antifungal activities of some thiolane-triazole derivatives.

    abstract::As part of our search for active agents against systemic fungal infections, a new series of triazole compounds with a thiolane ring was synthesized. Their antifungal activities were investigated in vitro and in vivo. Some of these thiolanetriazoles showed promising activity, comparable to that of ketoconazole, against...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.1258

    authors: Konosu T,Takeda N,Tajima Y,Yasuda H,Oida S

    更新日期:1990-05-01 00:00:00

  • One-pot N-arylation of indoles directly from N-arylsulfonylindoles via consecutive deprotection and S(N)Ar Reactions with activated Aryl halides.

    abstract::An efficient one-pot step by step t-BuOK-mediated procedure for the synthesis of N-arylindoles has been developed in moderate to good yields. The protocol involves the consecutive deprotection of N-arylsulfonylindoles as latent indoles and subsequent S(N)Ar reactions with activated aryl halides. This tandem reaction a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.321

    authors: Xu H,Fan LL

    更新日期:2009-03-01 00:00:00

  • Jatrophenone, a novel macrocyclic bioactive diterpene from Jatropha gossypifolia.

    abstract::A novel macrocyclic diterpene, jatrophenone, has been isolated from the whole plant of Jatropha gossypifolia. The structure of the compound was established by detailed studies of its one- and two-dimensional (1D and 2D) NMR spectra. The compound possesses significant antibacterial activity. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.870

    authors: Ravindranath N,Venkataiah B,Ramesh C,Jayaprakash P,Das B

    更新日期:2003-07-01 00:00:00

  • Stomach-site specific drug delivery system of clarithromycin for eradication of Helicobacter pylori.

    abstract::Gellan gum based floating beads containing clarithromycin (FBC) were prepared by iontotropic gelation method for stomach-specific drug delivery against Helicobacter pylori. The scanning electron microscope photograph indicated that prepared beads were spherical in shape with rough outer surface. Formulation variables ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1068

    authors: Rajinikanth PS,Mishra B

    更新日期:2009-10-01 00:00:00

  • Production of sesquiterpene-type phytoalexins by hairy roots of Hyoscyamus albus co-treated with cupper sulfate and methyl jasmonate.

    abstract::The production of sesquiterpene-type phytoalexins with a vetispyradiene skeleton by Hyoscyamus albus hairy roots induced by methyl jasmonate (MeJA) was reported in a previous paper. The production pattern on co-treatment with cupper sulfate and MeJA (CuSO(4)-MeJA) showed a TLC profile differing from that on treatment ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.934

    authors: Kawauchi M,Arima T,Shirota O,Sekita S,Nakane T,Takase Y,Kuroyanagi M

    更新日期:2010-07-01 00:00:00

  • New sesquiterpenes and calebin derivatives from Curcuma longa.

    abstract::One novel sesquiterpene with new skeleton, (6S)-2-methyl-6-(4-hydroxyphenyl-3-methyl)-2-hepten-4-one (1), two new bisabolane sesquiterpenes, (6S)-2-methyl-6-(4-hydroxyphenyl)-2-hepten-4-one (2), (6S)-2-methyl-6-(4-formylphenyl)-2-hepten-4-one (3), and two calebin derivatives, 4''-(4'''-hydroxyphenyl-3'''-methoxy)-2''-...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.940

    authors: Zeng Y,Qiu F,Takahashi K,Liang J,Qu G,Yao X

    更新日期:2007-06-01 00:00:00

  • New neplanocin analogues. VIII. Synthesis and biological activity of 6'-C-ethyl, -ethenyl, and -ethynyl derivatives of neplanocin A.

    abstract::This report describes the synthesis and antiviral effects of (6'R)-6'-C-ethynyl, -ethenyl, and -ethyl derivatives of neplanocin A (7a, 8a, and 9a, respectively) and the corresponding 6'S-diastereomers (7b, 8b, and 9b, respectively), as examples of 6'-C-substituted analogues of neplanocin A. Grignard reaction of the 6'...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1163

    authors: Shuto S,Obara T,Saito Y,Yamashita K,Tanaka M,Sasaki T,Andrei G,Snoeck R,Neyts J,Padalko E,Balzarini J,De Clercq E,Matsuda A

    更新日期:1997-07-01 00:00:00

  • One-step synthesis and bioassay of N-phosphoramidophosphonates.

    abstract::A simple one-step synthesis was accomplished for the preparation of N-phosphoramidophosphonates by a direct reaction of phosphoramidate (1) with heterocyclic aldehydes (2a-j) and dialkyl phosphites at 60-70 degrees C in the presence of tetramethylguanidine. The tetramethylguanidine not only catalyses this reaction but...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.57.1391

    authors: Veera Narayana Reddy M,Balakrishna A,Kumar MA,Reddy GC,Sankar AU,Reddy CS,Krishna TM

    更新日期:2009-12-01 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

  • Cytotoxic Biscembranoids from the Soft Coral Sarcophyton pauciplicatum.

    abstract::Ten biscembranoids (1-10), including the two new compounds sarcophytolides M and N (1 and 2), were isolated from the methanol extract of the Vietnamese soft coral Sarcophyton pauciplicatum. Their structures were elucidated by spectroscopic methods including one dimensional (1D)- and 2D-NMR, high-resolution electrospra...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00273

    authors: Nam NH,Tung PT,Ngoc NT,Hanh TT,Thao NP,Thanh NV,Cuong NX,Thao do T,Huong TT,Thung do C,Kiem PV,Kim YH,Minh CV

    更新日期:2015-01-01 00:00:00

  • Separation of sympathomimetic amines of abuse and related compounds by micellar electrokinetic chromatography.

    abstract::Separation of twelve sympathomimetic amines and related compounds by micellar electrokinetic chromatography (MEKC) with UV absorbance detection is described. These amines were well separated within 25 min using 50 mM sodium tetraborate solution containing 15 mM sodium dodecylsulfate (SDS) of pH 9.3 as a running soluti...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.905

    authors: Kuroda N,Sato D,Ohyama K,Wada M,Nakahara Y,Nakashima K

    更新日期:2001-07-01 00:00:00

  • A biologically active insulin analogue with modification in the A2 position. [2-Valine-A] sheep insulin.

    abstract::The synthesis and biological evaluation of [2-Valine-A] insulin ([Val2-A]insulin) is reported. In this insulin, the isoleucine residue in position A2, invariant in the majority of mammalian insulins, is substituted by valine. The same substitution, along with four others, occurs naturally in the insulin produced by th...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.670

    authors: Ohta N,Burke GT,Katsoyannis PG

    更新日期:1989-03-01 00:00:00

  • A novel method for estimation of transition temperature for polymorphic pairs in pharmaceuticals using heat of solution and solubility data.

    abstract::A novel method for thermodynamic stability studies of polymorphic drug substances has been developed. In order to estimate the transition temperature for an enantiotropic polymorphic pair, a formula for calculating the temperature at which the solubilities of each polymorph become equal has been derived with heat of s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.50.263

    authors: Urakami K,Shono Y,Higashi A,Umemoto K,Godo M

    更新日期:2002-02-01 00:00:00

  • Cucurbitane triterpenoids from Momordica charantia and their cytoprotective activity in tert-butyl hydroperoxide-induced hepatotoxicity of HepG2 cells.

    abstract::Two novel pentanorcucurbitane triterpenes, 22-hydroxy-23,24,25,26,27-pentanorcucurbit-5-en-3-one (1) and 3,7-dioxo-23,24,25,26,27-pentanorcucurbit-5-en-22-oic acid (2) together with a new trinorcucurbitane triterpene, 25,26,27-trinorcucurbit-5-ene-3,7,23-trione (3) were isolated from the methyl alcohol extract of the ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.1639

    authors: Chen CR,Liao YW,Wang L,Kuo YH,Liu HJ,Shih WL,Cheng HL,Chang CI

    更新日期:2010-12-01 00:00:00

  • Pharmacokinetics in chimpanzees of recombinant human tissue-type plasminogen activator produced in mouse C127 and Chinese hamster ovary cells.

    abstract::Pharmacokinetics of recombinant tissue-type plasminogen activator (rt-PA) produced in mouse C127 cells (t-PA(C127] and Chinese hamster ovary cells (t-PA(CHO] was investigated in chimpanzees. rt-PA was administered via a constant rate i.v. infusion for 60 min, and t-PA concentration and activity in plasma were measured...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.517

    authors: Tanigawara Y,Hori R,Okumura K,Tsuji J,Shimizu N,Noma S,Suzuki J,Livingston DJ,Richards SM,Keyes LD

    更新日期:1990-02-01 00:00:00

  • Isolation and characterization of 1,3-dicapryloyl-2-linoleoylglycerol: a novel triglyceride from berries of Hippophae rhamnoides.

    abstract::1,3-Dicapryloyl-2-linoleoylglycerol (1), a novel triglyceride, was isolated from berries of Hippophae rhamnoides. The structure was elucidated on the basis of MS, 1D and 2D NMR experiments including HMQC and HMBC. The metal chelating, free radical scavenging, and lipid peroxidation inhibiting properties of the compoun...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.1021

    authors: Swaroop A,Sinha AK,Chawla R,Arora R,Sharma RK,Kumar JK

    更新日期:2005-08-01 00:00:00

  • Isolation of Three New Diterpenes from Dodonaea viscosa.

    abstract::An investigation into the methanol extracts obtained from the stems of Dodonaea viscosa led to the isolation of one nor-clerodane diterpene (1) and two labdane diterpenes (2, 3), as well as 17 known compounds (4-20). The structures of these compounds were elucidated based on chemical and spectral evidence. The stereoc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c20-00327

    authors: Sagara T,Sugimoto S,Yamano Y,Nehira T,Masuda K,Otsuka H,Matsunami K

    更新日期:2021-01-01 00:00:00

  • Contribution of prostaglandins to the renal responses to magnesium lithospermate B isolated from salviae miltiorrhizae radix.

    abstract::The involvement of prostanoids in the improvement of adenine-induced renal failure in rats by magnesium lithospermate B was studied. After intraperitoneal administration of magnesium lithospermate B to renal failure rats, the levels of glomerular filtration rate, renal plasma flow and renal blood flow were increased. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.1568

    authors: Yokozawa T,Chung HY,Lee TW,Oura H,Tanaka T,Nonaka G,Nishioka I,Hirai A

    更新日期:1989-06-01 00:00:00

  • The structure of a new cardenolide diglycoside and the biological activities of eleven cardenolide diglycosides from Nerium oleander.

    abstract::A new cardenolide diglycoside (1) was isolated from Nerium oleander together with ten known cardenolide diglycosides 2-11. The structure of compound 1 was established on the basis of their spectroscopic data. The in vitro anti-inflammatory activity of compounds 1-11 was examined on the basis of inhibitory activity aga...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.371

    authors: Zhao M,Bai L,Toki A,Hasegawa R,Sakai J,Hasegawa T,Ogura H,Kataoka T,Bai Y,Ando M,Hirose K,Ando M

    更新日期:2011-01-01 00:00:00

  • Structures of toxic steroidal saponins from Narthecium asiaticum MAXIM.

    abstract::The full structures of the two steroidal saponins from Narthecium asiaticum MAXIM. We previously identified as toxic substances by monitoring the toxicity in guinea pigs were phytochemically reinvestigation on the aerial parts of the plant. The desired toxic saponins (6,7) were isolated together with two known lignan ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.1162

    authors: Inoue T,Mimaki Y,Sashida Y,Kobayashi M

    更新日期:1995-07-01 00:00:00

  • Studies on the constituents of Mikania hirsutissima (Compositae).

    abstract::Two novel norhumulene-type sesquiterpenes, named mikaniahumulene I (1) and II (2) were isolated along with nine known compounds, seven kaurenic acid-type diterpenes (3-9), a coumarin (10) and a flavone (11), from the aerial parts of Mikania hirsutissima DC (Compositae). The structures of new norhumulenes were determin...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1436

    authors: Ohkoshi E,Makino M,Fujimoto Y

    更新日期:1999-10-01 00:00:00

  • NF-κB inhibitory activities of glycosides and alkaloids from Zanthoxylum schinifolium stems.

    abstract::Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2-12) and alkaloids (13-17), were isolated from methanol extract o...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c13-00759

    authors: Li W,Yang SY,Yan XT,Sun YN,Song SB,Kang HK,Kim YH

    更新日期:2014-01-01 00:00:00

  • Selective Targeting of Cancer Stem Cells by 2-Aminodihydroquinoline Analogs.

    abstract::Many aminodihydroquinoline compounds have been studied to determine their cytotoxicity to cancer cells. However, anti-cancer stem cells (CSCs) activity of aminodihydroquinoline has not been tested in spite that CSC is believed to do an important roles in chemotherapy resistance and recurrence. The CSC selective target...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00726

    authors: Park H,Yu Y,Kim H,Lee E,Lee H,Jeon R,Kim WY

    更新日期:2017-04-01 00:00:00

  • Pericyclic reaction of ketenes with cascade reaction products of pyridine N-oxides and dipolarophiles. X-ray structures of the adducts and formation mechanism.

    abstract::The structures of the adducts derived from the reactions of substituted ketenes with dihydropyridine derivatives have been clarified by single crystal X-ray analyses and the formation mechanism is discussed on the basis of the reaction-path calculations by semiempirical and density functional theory (DFT) molecular or...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.1068

    authors: Oiso S,Eto M,Yoshitake Y,Harano K

    更新日期:2003-09-01 00:00:00