Regular Articles

Granulation of Core Particles Suitable for Film Coating by Agitation Fluidized Bed II.A Proposal of a Rapid Dissolution Test forEvaluation of Bitter Taste of Ibuprofen

T. Hamashita, M. Matsuzaki, T. Ono, M. Ono, Y. Tsunenari, T. Aketo, and S. Watano

pp. 883–887

Spectrophotometric Determination of IodineSpecies in Table Salt and PharmaceuticalPreparations

G. Mary, N. Balasubramanian, and K. S. Nagaraja

pp. 888–893

Synthesis and Evaluation of Novel N-Substituted-6-methoxynaphthalene-2-Carboxamides as Potential ChemosensitizingAgents for Cancer

T. N. Lokhande, C. L. Viswanathan, and A. S. Juvekar

pp. 894–896

Antioxidant and Anti-inflammatory RelatedActivities of Selected Synthetic Chalcones: Structure–Activity Relationship Studies UsingComputational Tools

R. Gacche, M. Khsirsagar, S. Kamble, B. Bandgar,N. Dhole, K. Shisode, and A. Chaudhari

pp. 897–901

A sensitive spectrophotometric method for the determination of iodine species like iodide, iodine, iodate and periodate is described. The method involves the oxidation of iodide to ICl2

� in the presence of iodate and chloride in acidic me-dium. The formed ICl2

� bleaches the dye methyl red. The decrease in the intensi-ty of the colour of the dye is measured at 520nm.

Methyl Red

N NH

HOOC

(H3C)2N N NH

I

HOOC

(H3C)2N

2I2 � IO3� � 6H� � 10Cl� 5ICl2

� � 3H2O

2I� � IO3� � 6H� � 6Cl� 3ICl2

� � 3H2O

ICl2� ICl � Cl�

A rapid dissolution test that can be used to investi-gate the early dissolution of ibuprofen in vitro was proposed to evaluate the taste-masking level of the coated particles. The bitter taste-masking level of the coated particles was successfully confirmed by using this novel dissolution test. These results indi-cate that this novel test can predict the taste-mask-ing level of the coated particles without the need to perform a sensory test.

Relationship between amount of coating film and concentration of ibuprofen ob-tained rapid dissolution test.

ii

CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 56, No. 7 July 2008 © Copyright, 2008, by the Pharmaceutical Society of Japan.

Conten t s

Novel bb -Lactam Antibiotics Synthesized byAmination of Catechols Using Fungal Laccase

A. Mikolasch, M. Wurster, M. Lalk, S. Witt, S. Seefeldt, E. Hammer, F. Schauer, W.-D. Jülich, and U. Lindequist

pp. 902–907

Structures and Interaction with DNA ofTernary Palladium(II) Complexes:[Pd(Gly)(X)] (Gly�Glycine; X�2,2�-Bipyridine, 1,10-Phenanthroline and2,2�-Bi-pyridylamine)

M. Yodoshi and N. Okabe

pp. 908–914

New Triterpene Constituents, FoliasalacinsA1—A4, B1—B3, and C, from the Leaves of Salacia chinensis

M. Yoshikawa, Y. Zhang, T. Wang, S. Nakamura, and H. Matsuda

pp. 915–920

Plasma-Assisted Immobilization of Heparinonto Low-Density Polyethylene Surface

S. Kondo, Y. Fukunaga, M. Oikawa, Y. Sasai, and M. Kuzuya

pp. 921–925

Conversion of Esculeoside A into Esculeogenin B

M. El Aasr, Y. Oshiro, Y. Fujiwara, H. Miyashita, T. Ikeda, M. Ono, H. Yoshimitsu, and T. Nohara

pp. 926–929

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

iii

Briaexcavatins M—P, Four New Briarane-Related Diterpenoids from Cultured Octocoral Briareum excavatum(Briareidae)

P.-J. Sung, M.-R. Lin, T.-L. Hwang, T.-Y. Fan, W.-C. Su, C.-C. Ho, L.-S. Fang, and W.-H. Wang

pp. 930–935

Prediction of Cyclooxygenase InhibitoryActivity of Curcuma Rhizome fromChromatograms by Multivariate Analysis

K. Tanaka, Y. Kuba, A. Ina, H. Watanabe, and K. Komatsu

pp. 936–940

Synthesis and Cytotoxicity Studies of Novel[1,2,4]Triazolo[1,5-a]pyrimidine-7-amines

X. Zhai, Y.-F. Zhao, Y.-J. Liu, Y. Zhang, F.-Q. Xun, J. Liu, and P. Gong

pp. 941–945

Formulation Design of an Oral, Fast-Disintegrating Dosage Form ContainingTaste-Masked Particles of Famotidine

T. Mizumoto, T. Tamura, H. Kawai, A. Kajiyama, and S. Itai

pp. 946–950

Novel Nortriterpenes from Phlomis umbrosa

P. Liu, Z. Yao, W. Zhang, Y. Takaishi, and H.-Q. Duan

pp. 951–955

A series of novel [1,2,4]triazolo[1,5-a]pyrimidine-7-amine derivatives were syn-thesized and evaluated for their in vitro cytotoxicity. The structure–activity rela-tionships were discussed and a number of compounds were found to have good cytotoxicity.

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

iv

Medicinal Foodstuffs. XXXIV. Structures ofNew Prenylchalcones and Prenylflavanoneswith TNF-aa and Aminopeptidase N InhibitoryActivities from Boesenbergia rotunda

T. Morikawa, K. Funakoshi, K. Ninomiya, D. Yasuda, K. Miyagawa, H. Matsuda, and M. Yoshikawa

pp. 956–962

Study on Colon-Specific 5-Fu pH-Enzyme Di-Dependent Chitosan Microspheres

X.-L. Zhao, K.-X. Li, X.-F. Zhao, D.-H. Pang, and D.-W. Chen

pp. 963–968

Binding Enhancements of Nicotinic Acid toWater-Soluble Zinc Porphyrins Based on TripleAttractions of Coordination, Coulomb, andCH–pp Interactions

H. Imai, H. Munakata, and Y. Uemori

pp. 969–972

Rh–N-Heterocyclic Carbene (NHC) Complex-Catalyzed Addition of Phenylboronic Acid toN-Sulfonyl and N-Phosphinoyl Aldimines

A. B. Md., Y. Suzuki, and M. Sato

pp. 973–976

Fluorophotometric Determination of Hydrogen Peroxide and Other Reactive Oxigen Species with Fluorescein Hydrazide(FH) and Its Crystal Structure

R. Nakahara, T. Fujimoto, M. Doi, K. Morita, T. Yamaguchi, and Y. Fujita

pp. 977–981

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

v

Notes

Selaginellin A and B, Two Novel NaturalPigments Isolated from Selaginella tamariscina

X.-L. Cheng, S.-C. Ma, J.-D. Yu, S.-Y. Yang, X.-Y. Xiao, J.-Y. Hu, Y. Lu, P.-C. Shaw, P. P.-H. But, and R.-C. Lin

pp. 982–984

Concise Synthesis of Dimemorfan (DF)Starting from 3-Hydroxymorphinan (3-HM)

J. Y. Kim, H.-C. Kim, J. Kim, and J. Lee

pp. 985–987

New Cembranoid Diterpenes from theVietnamese Soft Coral Sarcophyton mililatensis Stimulate OsteoblasticDifferentiation in MC3T3-E1 Cells

N. X. Cuong, T. A. Tuan, P. V. Kiem, C. V. Minh, E. M. Choi, and Y. H. Kim

pp. 988–992

Purine and Pyrimidine Derivatives from theSouth China Sea Gorgonian Subergorgiasuberosa

S.-H. Qi, S. Zhang, C.-H. Gao, and Q.-X. Li

pp. 993–994

Quantitative Analysis of Rabeprazole Sodiumin Commercial Dosage Forms bySpectrophotometry

N. Rahman, Z. Bano, and S. N. H. Azmi

pp. 995–1001

Two spectrophotometric assays for rabeprazole sodium are based on the reaction of drug with 3-methyl-2-benzothiazolinone hydrazone hydrochloride in the pres-ence of ammonium cerium(IV) nitrate (Method A) and 1-chloro-2,4-dinitroben-zene in dimethyl sulfoxide (Method B).

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

vi

P-TSA Catalyzed Facile and Efficient Synthesisof Polyhydroquinoline Derivatives throughHantzsch Multi-Component Condensation

S. R. Cherkupally and R. Mekala

pp. 1002–1004

Cardenolides from Antiaris toxicaria as Potent Selective Nur77 Modulators

M.-M. Jiang, Y. Dai, H. Gao, X. Zhang, G.-H. Wang, J.-Y. He, Q.-Y. Hu, J.-Z. Zeng, X.-K. Zhang, and X.-S. Yao

pp. 1005–1008

Two Labdane Diterpene and MegastigmaneGlycosides from Aquilegia hybrida

H. Yoshimitsu, M. Nishida, and T. Nohara

pp. 1009–1012

A Pregnane Glycoside from Overripe Tomato

T. Nohara, E. Iwakawa, S. Matsushita, Y. Fujiwara,T. Ikeda, H. Miyashita, M. Ono, and H. Yoshimitsu

pp. 1013–1014

Mechanism for Conversion of SpirosolaneDerivative into Pregnane

T. Nohara, K. Okamoto, S. Matsushita, Y. Fujiwara,T. Ikeda, H. Miyashita, M. Ono, H. Yoshimitsu, H. Kansui, and T. Kunieda

pp. 1015–1017

O

OHH

H

CH3

R2

R3

R1

R4O

O

Mak

er

TPA

Con

trol

4 1 5 6 7 11 9 8 10

10mMTR3

b -actin

A facile and efficient synthetic route to polyhydroquinolines has been devel-oped via four-component condensation reactions of aldehydes, dimedone, ethyl acetoacetate and ammonium acetate in the presence of p-TSA cata-lyst in ethanol at room temperature through Hantzsch reaction. Simple work-up, inexpensive and non-toxic catalyst, shorter reaction times along with excellent yields are the significant features of this protocol.

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

vii

Synthesis, Characterization, and theAntioxidative Activity of 4-{[(3,4-Dimethylpyrrole-2-carbonyl)hydrazono](phenyl)methyl}-3-methyl-1-phenylpyrazol-5-ol and Its Zinc(II),Copper(II), Nickel(II) Complexes

Q. Wang, Y. Wang, and Z.-Y. Yang

pp. 1018–1021

A New Homostilbene and Two NewHomoisoflavones from the Bulbs of Scillascilloides

Y. Nishida, M. Eto, H. Miyashita, T. Ikeda, K. Yamaguchi, H. Yoshimitsu, T. Nohara, and M. Ono

pp. 1022–1025

First Total Synthesis of the Phenolic 7,8-Dihydro-8-oxoprotoberberine Alkaloid,Cerasonine

T. N. Le and W.-J. Cho

pp. 1026–1029

Beyerane Derivatives and a SesquiterpeneDimer from Japanese Cypress (Chamaecyparis obtusa)

H. Y. Gao, L. J. Wu, N. Muto, H. Fuchino, T. Nakane, O. Shirota, T. Sano, and M. Kuroyanagi

pp. 1030–1034

Highly Oxygenated Lanostane Triterpenoidsfrom the Fungus Ganoderma applanatum

F. Wang and J.-K. Liu

pp. 1035–1037

scillabene A

O

OOH

H3CO

H3CO

OH

OH

O

OOH

HOOCH3

OCH3OH

CH3

OH

OH

scillavone A scillavone B

HO

H3CO

A new ligand H3L, 4-{[3,4-dimethylpyrrole-2-carbonyl)hydrazono](phenyl)me-thyl}-3methyl-1-phenylpyrazol-5-ol, and its three transition metal complexes, M(H2L)OAc·H2O (M�Cu, Ni), Zn(H2L)2 have been synthesized and character-ized. In addition, their antioxdative activities have been investigated.

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

viii

New C28 Steroidal Glycosides fromTubocapsicum anomalum

N. Kiyota, K. Shingu, K. Yamaguchi, Y. Yoshitake,K. Harano, H. Yoshimitsu, H. Miyashita, T. Ikeda, C. Tagawa, and T. Nohara

pp. 1038–1040

Inner-Hydrogen Tautomerism in Some 5,15-Unsymmetrically Disubstituted and bb -Unsubstituted Porphyrins

A. Tohara and M. Sato

pp. 1041–1046

Revised Absolute Stereochemistry ofRhodiolosides A—D, Rhodiolol A andSachalinol A from Rhodiola rosea

W. Li, D. Dou, and K. Koike

pp. 1047–1048

Silica Supported Phosphomolybdic Acid: An Efficient Heterogeneous Catalyst forFriedlander Synthesis of Quinolines

B. Das, M. Krishnaiah, K. Laxminarayana, and D. Nandankumar

pp. 1049–1051

Synthesis and Antiviral Activities of N-Mono-and/or N,N�-Di- Carbamoyl and AcylDerivatives of Symmetrical Diamines

N. Mibu, K. Yokomizo, M. Oishi, T. Miyata, and K. Sumoto

pp. 1052–1058

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

ix

Chemical & Pharmaceutical Bulletin Vol. 56, No. 7

x

About the cover: Eight novel nortriterpenoids with unusual skeleton were isolated from Phlomis umbrosa, and the skeletonof this type of compound has been confirmed by X-ray analysis for the first time. Compounds 1—3, 5, and 7 exhibitedpositive cytotoxic activities against the carcinoma cell lines Hela and L929 in vitro, and the bioactivity data suggested that theoxygen functions at C-18 and C-21 enhance cytotoxicity of these compounds. See the article by Liu et al. on page 951 of thisissue.