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Volume 57, Issue 3
Displaying 1-20 of 20 articles from this issue
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Regular Articles
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Maurice Iwu, Christopher Okunji, Michel Tchimene, Ngozi Anele, Kennedy ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 229-232
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSExtracts of named medicinal herbs (Garcinia kola, Zingiber oificinale, Aframonum melequeta and Ocimum viride) were formulated into an antitussive preparation to alleviate cough. Some physical properties of the cough syrup formulation evaluated were: specific gravity, pH, viscosity, content uniformity, and shelf life. The specific gravity and viscosity of the formulations were stable on storage, with glycerin-based formulations having higher values. The pH of the formulation varied from 4.2 to 5.3 and was also stable on storage. Glycerin-based formulations had lower pH values. The total flavonoids content of Streptol was calculated based on GB1 and found to be 46 mg. The estimated shelf life of the Streptol cough syrup was 4.5 years.View full abstractDownload PDF (85K) -
Hong Ji, Qiao-Hong Chen, Feng-Peng WangArticle type: Regular Article
2009 Volume 57 Issue 3 Pages 233-239
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA new and efficient approach toward the conversion of C19-diterpenoid alkaloids into diterpenes with [6+8+5+6] ring system is reported. Treatment of imines 5, 14, and 24 derived from the C19-diterpenoid alkaloids with NaNO2–NaOAc–HOAc afforded a series of novel rearrangement diterpenes 6—8, 15—19, and 25—27, respectively. The lactone 11 was obtained in 41% yield by treating 5 with NaNO2–HBr–Br2. The formation of diazonium intermediate is postulated, which was subsequently subjected to skeletal rearrangement, leading to the enlargement of B ring. All the new compounds were isolated and fully characterized.View full abstractDownload PDF (280K) -
Kazushi Kanazawa, Yuki Sato, Kazuhiro Ohki, Keiko Okimura, Yoshiki Uch ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 240-244
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSThis study on the structure–activity relationship of polymyxin B, a cyclic peptide antibiotic, used sixteen synthetic polymyxin B3 analogs including alanine scanning analogs to elucidate the contribution of the side chains to antimicrobial activity and lipopolysaccharide (LPS) binding. Of these analogs, [Ala5]-polymyxin B3 showed greatly reduced antimicrobial activity against Escherichia coli (E. coli), Salmonella Typhimurium (S. Typhimurium) and Pseudomonas aeruginosa (P. aeruginosa) with MIC values of 4—16 nmol/ml, suggesting that the Dab (α,γ-diaminobutyric acid) residue at position 5 is the most important residue contributing to bactericidal activity. The antibacterial contribution of Dab when located within the lactam ring (positions 5, 8 and 9) was greater than when located outside the ring (positions 1 and 3). [D-Ala6]-, [L-Phe6]-, [Ala7]-, and [Gly7]-polymyxin B3 analogs retained potent antimicrobial activity, indicating that neither the reduction of hydrophobic character of the D-Phe6-Leu7 region nor the D-configuration at position 6 is indispensable for antimicrobial activity. LPS binding studies showed that decreased hydrophobicity of the lactam ring had little effect, but the Nγ-amino function of the Dab residues at position 1, 3, 5, 8 and 9 greatly affected LPS binding, with the contribution of Dab5 being the most significant.View full abstractDownload PDF (223K) -
Akiko Suzuki, Osamu Shirota, Kanami Mori, Setsuko Sekita, Hiroyuki Fuc ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 245-251
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSIn the course of screening leishmanicidal active compounds from Asian and South American medicinal plants, a Nepalese medicinal plant, Tulsi (Ocimum sanctum L.), showed strong activity. We therefore studied the isolation and structural elucidation of the active constituents from O. sanctum L. From the ethyl acetate soluble fraction of the plant, seven new novel neolignan derivatives were isolated along with 16 known compounds. The structures of the new compounds (1—7) were elucidated as 6-allyl-3′,8-dimethoxy-flavan-3,4′-diol (1), 6-allyl-3-(4-allyl-2-methoxyphenoxy)-3′,8-dimethoxyflavan-4′-ol (2), 5-allyl-3-(4-allyl-2-methoxyphenoxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran (3), 1,2-bis(4-allyl-2-methoxyphenoxy)-3-(4-hydroxy-3-methoxyphenyl)-3-methoxypropane (4), 1-(4-hydroxy-3-methoxyphenyl)-1,2,3-tris(4-allyl-2-methoxyphenoxy)propane (5), 1-allyl-4-(5-allyl-2-hydroxy-3-methoxyphenoxy)-3-(4-allyl-2-methoxyphenoxy)-5-methoxybenzene (6), and 3-(5-allyl-2-hydroxy-3-methoxyphenyl)-1-(4-hydroxy-3-methoxyphenoxy)-prop-1-ene (7) by means of 1H-NMR, 13C-NMR, and 2D-NMR spectral data. Some of these compounds showed leishmanicidal activity.View full abstractDownload PDF (215K) -
Takayuki Yakura, Yuan Tian, Yû Yamauchi, Masanori Omoto, Tatsuya ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 252-256
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA catalytic hypervalent iodine oxidation of p-alkoxyphenols using 4-iodophenoxyacetic acid (1a) and Oxone® was developed. Reaction of p-alkoxyphenol (2) with a catalytic amount of 1a in the presence of Oxone® as a co-oxidant in 2,2,2-trifluoroethanol–water (1 : 2) gave the corresponding p-quinone (3) in excellent yield without special operation. The substituent effect on iodobenzene ring in the oxidation was observed; p-alkoxy is the most effective, with the series following the approximate order p-RO>p-Me, o-MeO, m-MeO>H>o-CO2H. And remarkable solvent effects were observed.View full abstractDownload PDF (106K) -
Sachiko Sugimoto, Seikou Nakamura, Sachiyo Yamamoto, Chihiro Yamashita ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 257-261
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSThe methanolic extract from the leaves of Ilex paraguariensis (Aquifoliaceae) was found to show an inhibitory activity on porcine pancreatic lipase. From the methanolic extract, three new triterpene oligoglycosides, mateglycosides A, B, and C, were isolated together with 18 known compounds. The chemical structures of new oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. Several constituents showed inhibitory activities on pancreatic lipase.View full abstractDownload PDF (140K) -
Masateru Ono, Hiroko Nishioka, Tadashi Fukushima, Hiroko Kunimatsu, Ai ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 262-268
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSAlkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction of the roots of Ipomoea operculata (GOMES) MART. (Convolvulaceae) afforded a glycosidic acid named operculinic acid H along with isovaleric, tiglic, and exogonic (3,6:6,9-diepoxydecanoic) acids. Operculinic acid H was characterized to be 3S,12S-dihydroxyhexadecanoic acid 12-O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-[O-β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→6)]-O-β-D-glucopyranoside on the basis of spectroscopic data and chemical evidence. The absolute configuration of exogonic acid determined from the α-methoxy-α-trifluoromethylphenylacetic acid esters of the hydrogenolysis products revealed that exogonic acid exists as a mixture (ca. 1 : 1) of two epimers, (3S,6S,9R)- and (3S,6R,9R)-diepoxydecanoic acids.View full abstractDownload PDF (198K) -
Sachiko Sugimoto, Guihua Chi, Yasuyo Kato, Seikou Nakamura, Hisashi Ma ...Article type: Regular Article
2009 Volume 57 Issue 3 Pages 269-275
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSThe methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia oleifera ABEL were found to exhibit inhibitory effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. The ethyl acetate- and 1-butanol-soluble fractions also showed inhibitory effects on rat lens aldose reductase and scavenging effects on 1,1-diphenylpicryl-2-hydrazyl radical and superoxide. From the 1-butanol-soluble fraction, four new acylated oleanane-type triterpene oligoglycosides, yuchasaponins A, B, C, and D, were isolated and their structures were elucidated on the basis of chemical and physicochemical evidence. On the other hand, quercetin 3-O-α-L-rhamnopyranoside and kaempferol 3-O-α-L-rhamnopyranoside were isolated from the ethyl acetate- and 1-butanol-soluble fractions as the principal constituents, and their gastroprotective effects were examined.View full abstractDownload PDF (143K)
Notes
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Afsar Khan, Viqar Uddin Ahmad, Umar Farooq, Sadia Bader, Saima ArshadArticle type: Notes
2009 Volume 57 Issue 3 Pages 276-279
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA BuOH-soluble part of the methanolic extract from the roots of Otostegia limbata yielded two new flavonol glycosides; kaempferol 3-O-[β-D-glucopyranosyl-(1→2)-{β-D-glucopyranosyl-(1→3)}-{β-D-glucopyranosyl-(1→4)}-α-L-rhamnopyranoside]-7-O-[α-L-rhamnopyranoside] (1) and kaempferol 3-O-[β-D-glucopyranosyl-(1→4)-β-D-6″‴[4-hydroxy (E)-cinnamoyl]glucopyranosyl-(1→3)-{β-D-glucopyranosyl-(1→2)}-α-L-rhamnopyranoside]-7-O-[α-L-rhamnopyranoside] (2). The structures of these compounds were elucidated by spectroscopic and chemical means. To the best of our knowledge, these are the largest flavonoids derivatives described so far from the genus Otostegia.View full abstractDownload PDF (116K) -
Chiao-Ting Yen, Pei-Wen Hsieh, Tsong-Long Hwang, Yu-Hsuan Lan, Fang-Ro ...Article type: Notes
2009 Volume 57 Issue 3 Pages 280-282
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA new flavonol, morin-3-O-α-rhamnopyranoside (1), along with four known flavonols, kaempferol 3-O-α-rhamnopyranoside (2), kaempferol 3-O-β-glucopyranoside (3), quercetin 3-O-α-rhamnopyranoside (4) and (+)-catechin (5), were isolated from the methanolic extract of Muehlenbeckia platyclada. The structures of these compounds were determined on the basis of chemical and spectroscopic evidence, as well as acid hydrolysis of the original glycoside. Isolates were evaluated for inhibition of generation of superoxide anion, and inhibition of release of neutrophil elastase. Compound 2 showed moderate inhibition of superoxide anion generation with an IC50 value of 6.11±0.86 μg/ml; 1, 3 and 5 inhibited neutrophil elastase release with IC50 values of 3.82±0.80, 8.61±1.38 and 4.37±0.72 μg/ml, respectively, and were 15-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay.View full abstractDownload PDF (75K) -
Sachiko Sugimoto, Seikou Nakamura, Hisashi Matsuda, Niichiro Kitagawa, ...Article type: Notes
2009 Volume 57 Issue 3 Pages 283-287
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA new dammarane-type triterpene ketone, panaxadione, was isolated from the seeds of Panax ginseng C. A. MEYER (Araliaceae) together with two dammarane-type and lupane-type triterpenes, an aromatic oligoglycoside, three sterol glycosides, and three dammarane-type triterpene oligoglycosides (ginsenosides Rd, Re, and Rg2). The structure of a new compound was elucidated on the basis of physicochemical evidence. The relative contents of major ginsenosides in the seeds were compared with those of the flesh parts of young and mature fruits.View full abstractDownload PDF (341K) -
Setsuya Sasho, Takashi Seishi, Mariko Kawamura, Misato Tomuro, Ryo Hir ...Article type: Notes
2009 Volume 57 Issue 3 Pages 288-293
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSNovel conformationally restricted diamine derivatives containing imidazolidinylidene propanedinitrile were synthesized and evaluated for human and rat histamine H3 receptor (H3R) binding affinities. Among them, compounds 2b, 2c, 2j, 2k and 2m were found to be potent ligands for both H3Rs with Ki values in the sub-nanomolar range, and showed potent H3 receptor antagonism.View full abstractDownload PDF (160K) -
Yoshiaki Ito, Satoshi Kamo, Samir Kumar Sadhu, Takashi Ohtsuki, Masami ...Article type: Notes
2009 Volume 57 Issue 3 Pages 294-297
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA new monoterpene glycoside (1) isolated from the aerial part of Sibirae angustata RCHD. (Rosaceae) was found to be 1-O-β-D-glucopyranosyl-geraniol-5,10-olide and named as sibiskoside. Acute toxicity study revealed that oral administration of 1 (2.5 g/kg body weight) to mice resulted in no death and no evidence of abnormalities in internal organs. Its oral administration to the mice reared with high-fat diet resulted in weight-loss, which was also reflected in serum triglyceride and sugar level, and the weight of abdominal fat. Sibiskoside could be considered to be an active ingredient of Liucha for exerting weight-loss effect in a drink of S. angustata.View full abstractDownload PDF (139K) -
Jun Lee, Eun-Kyoung Seo, Dae Sik Jang, Tae Joung Ha, Jong-Pyung Kim, J ...Article type: Notes
2009 Volume 57 Issue 3 Pages 298-301
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA new stereoisomer of 8-O-4′ system neolignan, (7R,8S)-1-(3,4-dimethoxyphenyl)-2-[4-(3-hydroxy-1-propenyl)-2-methoxyphenoxy]-propane-1,3-diol (1) and a new stereoisomer of tetrahydrofuranoid lignan, (7R,8S,7′S,8′R)-(3,4,5,3′,4′)-pentamethoxy-9,7′-dihydroxy-8.8′,7.O.9′-lignan (2) along with seven known lignans and neolignans (3—9) were isolated from the methanol extracts of the flower buds of Magnolia fargesii. The structures of these compounds (1—9) were elucidated by spectroscopic methods including 1D- and 2D-NMR as well as by comparison with reported values. Absolute configurations of new stereoisomers 1 and 2 were determined by circular dichroism (CD) spectra. The absolute configuration of (7S,8S,10S)-[tetrahydro-4-hydroxy-2-(3,4,5-trimethoxyphenyl)furan-3-yl]methyl 3,4-dimethoxy benzoate (3) was determined by Mosher's esterification method for the first time in this study. Three lignans, tanegool (4), (+)-dehydrodiconiferyl alcohol (5), and epieudes-min (6), were isolated from this plant for the first time. Superoxide radical scavenging activities of the isolates (1—9) were measured by irradiated riboflavin/ethylenediaminetetraacetic acid (EDTA)/Nitroblue tetrazolium (NBT) system, and their in vitro rat lens aldose reductase (RLAR) inhibitory activities were also evaluated.View full abstractDownload PDF (203K) -
Xiong Li, Dong Wang, Ming-yu Xia, Zhi-hui Wang, Wei-ning Wang, Zheng C ...Article type: Notes
2009 Volume 57 Issue 3 Pages 302-306
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSFive new prenylated flavonoids, maackiaflavanone A (1), maackiaflavanone B (2), maackiapentone (3), maackiapterocarpan A (4), maackiapterocarpan B (5) along with eleven known flavonoids were isolated from the stem bark of Maackia amurensis. The structures of the new compounds were elucidated by spectroscopic methods. The cytotoxicities of compounds 1—4, 6, 8—12 and 14—16 against four human cancer cell lines, A375S2, HeLa, MCF-7 and HepG2, were tested by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. Among the compounds tested, compound 2 showed the strongest cytotoxic activity with IC50 value of 7.8 μM against A375S2 and euchrenone b1 showed the most potent cytotoxicity with IC50 value of 4.5 μM against HeLa.View full abstractDownload PDF (121K) -
Kiminori Ohta, Shunsuke Konno, Yasuyuki EndoArticle type: Notes
2009 Volume 57 Issue 3 Pages 307-310
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSAlthough the complexation of carborane derivatives with β-cyclodextrin (β-CD) is well-known, we present here the first observation of the complexation of carborane derivatives with α-CD in aqueous solution. The stoichiometry and association constant (Ka) of the complexes were estimated from Job's plots and NMR titration studies, respectively. The carborane : α-CD stoichiometry was 1 : 1 in all cases. The complexation ability and selectivity of the carborane derivatives for α-CD are markedly decreased compared with those for β-CD. The interaction between the carborane cage and the hydrophobic cavity of α-CD appears to be weak, probably because the hydrophobic cavity of α-CD is too small to accommodate the carborane cage. The C–H hydrogen and the polar substituents of carborane cage may form hydrogen bonds with secondary alcohol groups at the rim of α-CD. The orientation of the carborane cage influences the inclusion process, and o- and m-carborane derivatives showed moderately stronger association constants than p-carborane derivatives.View full abstractDownload PDF (215K) -
Kazuko Yoshikawa, Yuki Matsumoto, Hiroshi Hama, Masami Tanaka, Haifeng ...Article type: Notes
2009 Volume 57 Issue 3 Pages 311-314
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSSix new illudoid sesquiterpene, russujaponols G—L (1—6) were isolated from the fruit bodies of Russula japonica. Their structures were established primarily by 2D NMR experiments. Furthermore, russujaponols I—K showed neurite outgrowth promoting activity in the primary cultured rat cortical neurons.View full abstractDownload PDF (797K) -
Yuriko Ikeda, Masanori Inagaki, Koji Yamada, Xiao Wen Zhang, Bo Zhang, ...Article type: Notes
2009 Volume 57 Issue 3 Pages 315-317
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSA galactocerebroside (BAC-4-4a) was obtained from its parent galactocerebroside molecular species (BAC-4) by using two types of reversed-phase HPLC column. The parent cerebroside BAC-4 has been isolated from less polar lipid fraction of CHCl3/MeOH extract of sea cucumber Bohadschia argus, together with known typical types of glucocerebroside molecular species. The structure of BAC-4-4a was determined on the basis of chemical and spectroscopic evidences as 1-O-(β-D-galactopyranosyl)-(2S,3R,4E)-2[(2′R,15′Z)-2-hydroxytetracosenoylamino]-4-heptadecene-1,3-diol. This is the first report of isolation and structure determination of galactocerebroside from sea cucumber.View full abstractDownload PDF (117K) -
Biswanath Das, Bommena Ravikanth, Keetha Laxminarayana, Bethapudi Rama ...Article type: Notes
2009 Volume 57 Issue 3 Pages 318-320
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSChemical investigation on the stems of Jatropha multifida resulted in the isolation of two new macrocyclic diterpenoids whose structures were established by extensive studies of their 1D and 2D-NMR spectra. The occurrence of ten other known compounds in this species is reported here for the first time.View full abstractDownload PDF (83K) -
Hui Xu, Ling-Ling FanArticle type: Notes
2009 Volume 57 Issue 3 Pages 321-323
Published: March 01, 2009
Released on J-STAGE: March 01, 2009
JOURNAL FREE ACCESSAn 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 SNAr reactions with activated aryl halides. This tandem reaction affords an efficient and convenient preparation of N-arylindoles that benefit from prior indoles protection by arylsulfonyl group, and can shorten a reaction sequence and improve synthetic efficiency.View full abstractDownload PDF (77K)
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