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Volume 50, Issue 1
Displaying 1-26 of 26 articles from this issue
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Reviews
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Barry M. TrostArticle type: Review
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 1-14
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSPalladium catalyzed asymmetric allylic alkylations represent a challenging problem because the mechanism of the reaction places the chiral environment distal to the bond breaking or making events responsible for the asymmetric induction. Furthermore, unlike virtually every other asymmetric process, many strategies can be employed for introduction of asymmetry and many different types of bonds can be formed. While over 100 different ligands have been designed, a family of ligands derived from 2-diphenylphosphinobenzoic or 1-naphthoic acid and chiral scalemic diamines have been successful in inducing excellent enantioselectivity by five different enantiodiscriminating events. These methods have already provided practical strategies towards numerous biological targets—some of which are adenosine and its enantiomer, aflatoxin B, aristeromycin, calanolide A and B, carbovir, cyclophellitol, ethambutol, galanthamine, mannostatin, neplanocin, phyllanthocin, sphingofungins E and F, tetraponaines, vigabatrin, and valienamine.View full abstractDownload PDF (169K)
Regular Articles
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Elena Ramirez, Marisa Cabeza, Ivonne Heuze, Edgar Gutiérrez, Eu ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 15-20
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSThe pharmacological activity of several new pregnane derivatives 15—19 were determined on gonadectomized male hamster flank organs, seminal vesicles and in vitro conversion of testosterone (T) to dihydrotestosterone (DHT) as 5α-reductase inhibitors. Steroids 15—19 decreased the diameter of the pigmented spot in the flank organs as compared to the T treated animals; in this model, steroids 16 and 19 showed a higher activity than the commercially available finasteride 3. Injection of T increased the weight of the seminal vesicles. Compounds 15—19 when injected together with T decreased the weight of the seminal vesicles thus showing an antiandrogenic effect. The trienone 19 exhibited a considerably higher activity than finasteride. Steroids 15—19 inhibited the in vitro metabolism of [3H]T to [3H]DHT in seminal vesicles homogenates of gonadectomized male hamsters. Compounds 18 and 19 showed a much higher antiandrogenic effect than finasteride. This enhancement of the biological activity could probably be attributed to the coplanarity of the steroidal skeleton as previously observed by our group. The high antiandrogenic activity of the epoxy compound 16 is probably the result of the ring opening of the oxiran ring with the nucleophilic part of the enzyme 5α-reductase thus leading to a stable adduct with concomitant deactivation of this enzyme.View full abstractDownload PDF (71K) -
Abolghasem Jouyban, Maryam Khoubnasabjafari, Hak-Kim Chan, Brian J. Cl ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 21-25
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSNumerical methods to predict the solubility of anthracene in mixed solvents have been proposed. A minimum number of 3 solubility data points in sub-binary solvents has been employed to calculate the solvent–solute interaction terms of a well established colsolvency model, i.e. the combined nearly ideal binary solvent/Redlich–Kister model. The calculated interaction terms were used to predict the solubility in binary and ternary solvent systems. The predicted solubilities have been compared with experimental solubility data and the absolute percentage mean deviation (APMD) has been computed as a criterion of prediction capability. The overall APMD for 25 anthracene data sets in binary solvents is 0.40%. In order to provide a predictive method, which is based fully on theoretical calculations, the quantitative relationships between sub-binary interaction terms and physico-chemical properties of the solvents have been presented. The overall APMD value for 41 binary data sets is 9.19%. The estimated binary interaction terms using a minimum number of data points and the quantitative relationships have then been used to predict anthracene solubility data in 30 ternary solvent systems. The produced APMD values are 3.72 and 15.79%, respectively. To provide an accurate correlation for solubility in ternary solvent systems, an extension to the combined nearly ideal multicomponenet solvent/Redlich–Kister (CNIMS/R-K) model was proposed and the corresponding overall AMPD is 0.38%.View full abstractDownload PDF (55K) -
Satoru Watano, Eri Shimoda, Yoshifumi OsakoArticle type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 26-30
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSThis paper describes a novel and simple method for measuring the physical strength of pharmaceutical pellets prepared by extrusion granulation. Pharmaceutical powders composed of lactose, cornstarch, and microcrystalline cellulose were kneaded with purified water and dry binder (hydroxypropylcellulose), then extruded through a dome-type extrusion granulator. The physical strength of the dried extruded pellets was measured with a novel system: pellets and grinding alumina media were both fed into a ball mill pot and then “grinding degree” was measured as defined by the ground fine powder fraction after being rotated in the pot. The grinding conditions such as grinding time and number of alumina balls were optimized. The measured physical strength and pellet strength measured with a typical strength tester was compared. Quantitative relationships between the strength and the physical properties of the pellets such as friability and disintegration time were also investigated. It was found that the newly developed system could easily and accurately evaluate the physical strength of extruded pellets and could also predict the various physical properties.View full abstractDownload PDF (166K) -
Andrew Tsotinis, Margarita Vlachou, Andreas Eleutheriades, Effie Prine ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 31-39
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSThe potency of new indolic N1-phenethyl substituted melatoninergic ligands with and without methyl groups in the α and β position of the alkanamidoethyl side chain was examined using the pigment aggregation response in a clonal line of Xenopus laevis melanophores. The non 5-OMe substituted compounds, 8a—e, are all weak antagonists while introduction of the 5-OMe group, 9a—e, increases both agonist and antagonist activity except for 9c (R=C3H7), which is only an agonist and 9e (R=c-C4H7), which is only an antagonist. Introduction of an α-methyl group into the 5-OMe derivatives, 14a—e, reduces the agonist potency while introduction of a β-methyl group has only a small effect on either the agonist or antagonist potency. Double β-methyl substitution of the 5-OMe derivatives, 20a—e, generally increases the agonist potential (20c, R=C3H7 is the most potent agonist of the compounds described) and decreases the antagonist potency, except for 20a (R=CH3), which is the most potent antagonist of this series of compounds.View full abstractDownload PDF (110K) -
Haydee Blanco-Fuente, Blanca Esteban-Fernández, José Bla ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 40-46
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSCarbomers are carboxyvinylic derivatives that are widely used in the manufacture of hydrogel dosage forms. Because of their anionic nature and large number of acid groups, they tend to interact with cationic substances, and with other hydrophilic polymers containing alcohol groups. Here, we report a study of interactions between the carbomer Carbopol® and the cationic drug propranolol hydrochloride in the solid state and in solution, and of the effects of such interactions on the properties of the hydrogel. We found that the drug forms an insoluble ionic complex with the polymer, modifying all of the hydrogel properties studied (swelling, release, bioadhesion). The inclusion of β-cyclodextrin in the formulation reduces polymer/drug interactions, so that hydrogel properties remain unchanged. This is probably attributable to formation of inclusion complexes of β-cyclodextrin and the drug, so that the drug is prevented from interacting with the polymer.View full abstractDownload PDF (93K) -
Atsushi Yamamoto, Ko Nakamura, Kazuhito Furukawa, Yukari Konishi, Taka ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 47-52
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSTo find new tachykinin NK1 receptor antagonists from natural sources, we examined the tachykinin antagonist activity in the extracts of approximately 200 species of plants by the use of isolated guinea pig ileum. As a result, we discovered a novel and potent NK1 receptor antagonist in the extract of dried flowers of Matricaria chamomilla L. (chamomile). The structure of the antagonist was established as N1, N5, N10, N14-tetrakis[3-(4-hydroxyphenyl)-2-propenoyl]-1, 5, 10, 14-tetraazatetradecane (tetracoumaroyl spermine, 1a). The Ki values of 1a, estimated from the inhibitory action on the substance P (SP)-induced contraction of the guinea pig ileum and the inhibition of the binding of [3H][Sar9, Met(O2)11]SP to human NK1 receptors, were 21.9 nM and 3.3 nM, respectively. 1a is the first potent NK1 receptor antagonist from natural sources and it has a unique structure of a polyacylated spermine. 1a was concentrated in pollen of Matricaria chamomilla L. and was also found in the extracts of flowers of other four species of Compositae. In addition, we found N1, N5, N10-tris[3-(4-hydroxyphenyl)-2-propenoyl]-1, 5, 10, 14-tetraazatetradecane (2) as a new compound in the extract of flowers of Matricaria chamomilla L., which did not exhibit any tachykinin antagonist activity. A number of related compounds were synthesized, and the structure–activity relationship was studied.View full abstractDownload PDF (82K) -
Takashi Miki, Masakuni Kori, Ryu-ichi Tozawa, Masahira Nakamura, Yasuo ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 53-58
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSThe (3,5-trans)-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid derivatives 1 have been previously identified as potent squalene synthase inhibitors. A series of (4,1-benzoxazepin-3-ylidene)acetic acid derivatives were synthesized and evaluated for their inhibition of rat and human squalene synthase, and the (E)-isomers were found to exhibit potent inhibitory activity, with the same potency as 4,1-benzoxazepine-3-acetic acid derivatives. In contrast the (Z)-isomers did not exhibit significant inhibitory activity, and the active conformation of the 4,1-benzoxazepine-3-acetic acid derivatives was deduced from the folded conformation of the (E)-isomers.View full abstractDownload PDF (107K) -
Naoki Tarui, Kazuo Nakahama, Yoichi Nagano, Motowo Izawa, Kiyoharu Mat ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 59-65
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSMicrobial enantioselective ester hydrolysis for the preparation of optically active (3R, 5S)-(−)-5-phenyl-4,1-benzoxazepine-3-acetic acid derivatives as potent squalene synthase inhibitors was investigated. Pseudomonas diminuta and Pseudomonas taetrolens hydrolyzed the racemic ethyl ester of the 5-(2-chlorophenyl) analogue to yield the (−)-carboxylic acid with excellent enantiomeric excess (>99% ee). We found that the (−)-enantiomer was an active inhibitor. Bulkiness of the ester moiety did not affect the enantioselectivity but did affect reac-tivity. The racemic ethyl ester of the 5-(2-methoxyphenyl) analogue, 5-(2,3-dimethoxyphenyl) analogue and 5-(2,4-dimethoxyphenyl) analogue were also hydrolyzed with Pseudomonas taetrolens to afford enantiomerically pure (−)-carboxylic acids in large scale. As another route to (3R,5S)-(−)-7-chloro-5-(2,3-dimethoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid [(−)-1c], the earlier intermediate (−)-2-amino-5-chloro-α-(2,3-dimethoxyphenyl)benzyl alcohol [(−)-12] was successfully obtained by asymmetric hydrolysis of (±)-5-chloro-α-(2,3-dimethoxyphenyl)-2-pivaloylaminobenzyl acetate with Pseudomonas sp. S-13 with >99% ee in kilogram scale followed by alkaline treatment. The product (−)-12 was converted to (−)-1c without racemization.View full abstractDownload PDF (106K) -
Tetsuko Matsumura, Toru Ishikawa, Junichi KitajimaArticle type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 66-72
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSNine monoterpenoids related to carvone and seven glucosides were isolated from the water-soluble portion of the methanolic extract of the caraway (fruit of Carum carvi L.), and their structures were clarified by spectral investigation. Among them, eight monoterpenoids and six glucosides were new.View full abstractDownload PDF (93K) -
Zhong Yuan, Yasuhiro Tezuka, Wenzhe Fan, Shigetoshi Kadota, Xian LiArticle type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 73-77
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSFrom the underground parts of Glehnia littoralis Fr. Schmidt ex Miquel (Umbelliferae), 26 compounds, including two new lignan glycosides [glehlinosides A (1) and B (2)], a new neolignan glycoside [glehlinoside C (3)], and a new phenylpropanoid glycoside [4-[β-d-apiofuranosyl-(1→6)-β-d-glucopyranosyloxy]-3-methoxypropiophenone (4)], were obtained and their structures were determined by analysis of their spectral data. The 1, 1-diphenyl-2-picrylhydrazyl radical-scavenging assay disclosed quercetin (8), isoquercetin (9), rutin (10), chlorogenic acid (11), and caffeic acid (24) as the major antioxidative constituents in this crude drug.View full abstractDownload PDF (71K) -
Shun-Li Wang, Chi-Hsiang Chuang, Shan-Yang LinArticle type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 78-82
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSIn order to simulate the in vivo binding behavior of angiotensin-converting enzyme (ACE) inhibitors to the zinc-containing active center of ACE, the in vitro interaction between lisinopril and zinc or nickel ions was investigated in aqueous solutions of different pH by using attenuated total reflection (ATR)/Fourier transform infrared (FT-IR) spectroscopy with second-derivative IR spectral analysis. The results indicated that the lisinopril dissociation process occurred in a stepwise fashion during increase in pH. The IR peaks at 1642 cm−1 (carbonyl stretching of tertiary amide) and at 1582 cm−1 (asymmetric COO− stretching) for lisinopril in solution at pH 3.5 shifted to 1606 and 1586 cm−1 after addition of Ni2+ ions, respectively, but there was no marked changes in IR spectra of lisinopril after addition of Zn2+ ions. When the Zn2+ ions were added to lisinopril solution at pH 5.0, the peak at 1642 cm−1 also shifted to 1604 cm−1 and the peak at 1582 cm−1 shifted to 1586 cm−1, similar to the changes at pH 3.5 after adding Ni2+ ions. However, the peaks at 1582 and 1642 cm−1 both shifted to 1599 cm−1 after addition of Ni2+ ions at pH 5.0 or at pH 7.3. The peak at 1576 cm−1 also shifted to 1599 cm−1 after addition of Zn2+ ions to lisinopril solution at pH 7.3. Different coordination sites or types (chelating, bridging or pseudo-unidentate complex) between lisinopril and Zn2+ or Ni2+ ions were proposed, based on the separation value between νas (COO−) and νs (COO−), and the shifting of carbonyl groups. Coordination of the secondary amine in lisinopril to metal ions was also evidenced.View full abstractDownload PDF (69K) -
Taisuke Itaya, Takehiko Iida, Itaru Natsutani, Masashi OhbaArticle type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 83-86
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSThe relationship between the product patterns and the configurations of 1,2-cycloheptane- and 1,2-cyclooctanediols 9 in the cyclocondensations with oxalyl chloride in the presence of triethylamine at 0 °C has been shown analogous to that obtained for 1,2-disubstituted acyclic ethylene glycols 1: cis-1,2-cyclooctanediol (9f) produced the cyclic oxalate 14f as the major product, while trans-1,2-cycloheptanediol (9e) and trans-1,2-cyclooctanediol (9g) formed the cyclic carbonates 12e, g as the major products. On the other hand, the cyclic oxalates 14a—d were formed as the major products from 1,2-cyclopentane- and 1,2-cyclohexanediols regardless of the configuration. These results can be accounted for by assuming the boat-like transition states for cyclizations of the half esters of comparatively rigid five- and six-membered diols 9a—d. The cyclic oxalates 14a, c may be directly formed through the resulting tetrahedral intermediates from cis-diols (9a, c), and the cyclic carbonates 12a, c as the minor products after ring inversion of the tetrahedral intermediates. The tetrahedral intermediates from the trans-isomers 9b, d cannot undergo ring inversion, producing no traces of the cyclic carbonates 12b, d.View full abstractDownload PDF (64K) -
Toshihito Hosokawa, Masahiro Yamauchi, Yoshihiko Yamamoto, Kenji Iwata ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 87-91
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSKW-3902 (a newly synthesized adenosine A1-receptor antagonist) has potent diuretic and renal protective activities. The objective of the present study was to develop an injectable formulation of KW-3902, that was water-insoluble and less than 1 µg/ml, and so lipid emulsion was selected as a favorable formulation. Changing the mixing ratio of oil to lecithin, the particle size of the lipid emulsion was controlled, and by adjusting the mixing ratio of oil/lecithin=1 : 1, the weight ratio, a lipid emulsion with a mean particle size of 130 nm was prepared. This small particle size makes this emulsion filter-sterilizable, which is a favorable feature for heat labile products. The stability of the KW-3902 lipid emulsion was assessed from the viewpoint of the electrostatic repulsion, and by including the oleic acid a stable lipid emulsion was developed, which was stable for at least 12 months at 10 and 25 °C and for 3 months at 40 °C. The feature of this small particle size emulsion was also characterized by comparing it with a conventional emulsion (oil/lecithin=1 : 0.12, the weight ratio, particle size is 220 nm). The release of KW-3902 from the oil particles was measured and the apparent permeability of KW-3902 was calculated from the equation according to Fick's theory. The apparent permeability, P, of KW-3902 was not affected by the particle size of the emulsion (1.78×10−11 cm/s for the small emulsion and 1.76×10−11 cm/s for the conventional emulsion). The distribution mode of KW-3902 in the lipid emulsion was also discussed by considering the findings of the permeability and solubility of KW-3902.View full abstractDownload PDF (68K) -
Fumio Yamada, Mayumi Tamura, Atsuko Hasegawa, Masanori SomeiArticle type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 92-99
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSPsilocin analogs having either a formyl group (9—12) or a bromine atom (13—18) at the 5- or 7-position have been prepared for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25, 29, 30), 4-benzyloxyindole-3-acetonitriles (20, 31), and 4-benzyloxy-N, N-dimethyltryptamine (32, 34, 35) have also been established.View full abstractDownload PDF (103K) -
Yu Momose, Tsuyoshi Maekawa, Hiroyuki Odaka, Hitoshi Ikeda, Takashi So ...Article type: Regular Article
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 100-111
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSA series of 5-(4-alkoxyphenylalkyl)-1H-tetrazole derivatives, containing an oxazole-based group at the alkoxy moiety, was prepared and their antidiabetic effects were evaluated in two genetically obese and diabetic animal models, KKAy mice and Wistar fatty rats. Syntheses were performed by cyclization of the corresponding nitriles reacting with azide compounds. A large number of the 5-(4-alkoxyphenylalkyl)-1H-tetrazoles showed potent glucose and lipid lowering activities in KKAy mice. In particular, 5-[3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridyl]propyl]-1H-tetrazole had potent glucose lowering activity (ED25=0.0839 mg⋅kg−1⋅d−1), being 72 times more active than pioglitazone hydrochloride (ED25=6.0 mg⋅kg−1⋅d−1). This compound also showed strong glucose lowering (ED25=0.0873 mg⋅kg−1⋅d−1) and lipid lowering effects (ED25=0.0277 mg⋅kg−1⋅d−1) in Wistar fatty rats. The antidiabetic effects of this compound are considered to be due to its potent agonistic activity for peroxisome proliferator-activated receptor γ (PPARγ) (EC50=6.75 nM).View full abstractDownload PDF (131K)
Notes
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Erum Anis, Itrat Anis, Saeed Ahmed, Ghulam Mustafa, Abdul Malik, Nigha ...Article type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 112-114
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSTwo new compounds, 7′-(3′, 4′-dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (4), and 7′-(4′-hydroxy, 3′-methoxyphenyl)-N-[(4-butylphenyl)ethyl]propenamide (5) have been isolated from Cuscuta reflexa along with five known compounds, 6, 7-dimethoxy-2H-1-benzopyran-2-one (1), 3-(3, 4-dihydroxyphenyl)-2-propen-1-ethanoate (2), 6, 7, 8-trimethoxy-2H-1-benzopyran-2-one (3), 3-(4-O-β-d-glucopyranoside-3, 5-dimethoxyphenyl)-2-propen-1-ol (6), 2-(3-hydroxy-4-methoxyphenyl)-3, 5-dihydroxy-7-O-β-d-glucopyranoside-4H-1-benzopyrane-4-one (7), reported for the first time from this species. Structures of these compounds were determined by spectral analysis. These compounds showed strong inhibitory activity against α-glucosidase.View full abstractDownload PDF (51K) -
Hongquan Duan, Yoshihisa Takaishi, Yoshinori Fujimoto, Cristina Garzon ...Article type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 115-117
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSTwo coumarins and one polyacetylene, 5-O-(3-chloro-2-hydroxy-3-methylbutyl)-8-methoxypsoralen (1), 2′, 3′-dihydro-jatamansin (2), and 10-chloro-1-heptadecene-4, 6-diyne-3, 8, 9-triol (3), along with 15 known compounds (4—18), were isolated from the methanol extract of Niphogeton ternata. Their structures were elucidated by spectroscopy.View full abstractDownload PDF (55K) -
Takeshi Kinoshita, Motoko ShimadaArticle type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 118-120
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSA new C-8 prenylated 5, 7-dimethoxycoumarin named omphamurrayin was isolated from the leaves of Murraya paniculata var. omphalocarpa, and its structure was established as 5, 7-dimethoxy-8-(1-oxo-2-senecioyl-3-methyl-3-butenyl)-2H-1-benzopyran-2-one on the basis of the spectroscopic evidence. The taxonomic status of M. paniculata var. omphalocarpa is briefly discussed, along with its synonymity to M. paniculata from the chemosystematic viewpoint.View full abstractDownload PDF (48K) -
Kazuki Watanabe, Yoshihiro Mimaki, Hiroshi Sakagami, Yutaka SashidaArticle type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 121-125
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSPhytochemical analysis of the rhizomes of Cimicifuga racemosa (Ranunculaceae) resulted in the isolation of twelve cycloartane glycosides (1—12), including four new ones (4—6, 12). The structures of the new compounds were determined by spectroscopic analysis, including two-dimensional (2D) NMR data, and chemical methods. The isolated compounds were evaluated for their cytotoxic activities against human oral squamous cell carcinoma (HSC-2) cells and normal human gingival fibroblasts (HGF).View full abstractDownload PDF (64K) -
Mitsuru Satoh, Masayoshi Ishii, Mitsuo Watanabe, Kimiaki Isobe, Taketo ...Article type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 126-128
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSDiastereomeric mixture at C-3 of (9R, 10R)-panaxytriol acetonide (3) and (9S, 10S)-panaxytriol acetonide (4) were enantioselectively acetylated to give (3R)-acetates (3a-Ac, 4a-Ac) and (3S)-alcohols (3b, 4b) by enzyme mediated-acetylation using CHIRAZYME and vinyl acetate, respectively. Hydrolysis of (3R)-acetate (3a-Ac, 4a-Ac) with CHIRAZYME and phosphate buffer afforded (3R)-alcohols (3a, 4a), respectively. Deprotection of panaxytriol acetonides (3a, 3b, 4a, 4b) gave panaxatriol and its isomers, respectively. Comparison of optical rotation values of the synthetic panaxatriols with that of the natural one confirmed that the absolute configuration of panaxytriol sould be 3R, 9R, 10R.View full abstractDownload PDF (55K) -
Fumiko Fujisaki, Nobuhiro Abe, Kunihiro SumotoArticle type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 129-132
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSNovel benzamide derivatives, N-[1-(aminocarbonyl)-2-(1-piperidinyl)ethyl]benzamides (4 and 5), were prepared from the reaction of β-piperidinoalanine (6) as the starting material.View full abstractDownload PDF (69K) -
Jian-Mei Huang, Kousuke Nakade, Mamiko Kondo, Chun-Shu Yang, Yoshiyasu ...Article type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 133-136
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSIn the study of bioactive substances in Illicium plants, the methanol extract of I. merrillianum showed brine shrimp lethality test (BST) activity at 200 µg/ml. Bioassay-guided fractionation of the BST active fractions resulted in the isolation of 4-O-methyleudesm-11-en-4α-ol, eudesmol-11-en-4α-ol and (−)-hinokinin as potent BST active compounds. On the other hand, four new highly oxygenated seco-prezizaane-type sesquiterpenes, merrilliortholactone (1), 2α-hydroxycycloparvifloralone (2), 2α-hydroxycycloparviflorolide (3), and 2α-hydroxyanisatin (4) were isolated from the BST-inactive polar fractions. The structures of new compounds were elucidated by extensive analyses of spectral data. Furthermore, the absolute configuration of 3 was established by the modified Mosher's method. Compounds 1—4 showed neither BST activity at 100 µg/ml nor neurite outgrowth-promoting activity.View full abstractDownload PDF (61K) -
Zhi-Hong Jiang, Takashi Tanaka, Takako Sakamoto, Isao Kouno, Jin-Ao Du ...Article type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 137-139
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSA new biflavanone (1) with a C-3/C-3″ linkage, a new daphnane-type diterpene (2) acylated by an unsaturated fatty acid, and a new coumarin glycoside (3), along with six lignans, two phenylpropanoids, five flavonoids, two diterpenes, and three coumarins were isolated from the roots of Stellera chamaejasme L. (Thymelaeaceae). Elucidation of these secondary metabolites of S. chamaejasme L. supplied strong chemical verification of the close taxonomic relationships among the genera Stellera, Daphne, and Wikstroemia, all of which belong to the family Thymelaeaceae.View full abstractDownload PDF (59K) -
Keiko Hojo, Mitsuko Maeda, Timothy J. Smith, Koichi KawasakiArticle type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 140-142
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSIn peptide synthesis, hydrazides are important intermediates for the azide coupling method. A hydrazide is converted to the corresponding azide in the presence of an acid and a nitrite. When acetic acid (or formic acid) is used as the acid, partial acetylation (or formylation) of the hydrazide occurs as a side reaction. Formylation of the hydrazide is much faster than acetylation. Removal of the formyl group on the hydrazide with hydrazine and hydroxylamine was studied. The rate of deformylation with hydrazine treatment is faster than that with hydroxyl-amine treatment.View full abstractDownload PDF (48K) -
Akito Yasuhara, Naoyuki Suzuki, Takao SakamotoArticle type: Note
Subject area: [not specified]
2002 Volume 50 Issue 1 Pages 143-145
Published: 2002
Released on J-STAGE: March 19, 2002
JOURNAL FREE ACCESSFurostifoline, a furo[3, 2-a]carbazole alkaloid, was synthesized in 10% overall yield in four steps from 2-acetyl-3-bromofuran. The key step of this synthesis was the 2-substituted indole formation with tetrabutylammonium fluoride (TBAF) from 2-(2-propenyl)-3-((2-ethoxycarbonylamino)phenylethynyl)furan, which was easily prepared from ethyl 2-ethynylphenylcarbamate with 3-bromo-2-(2-propenyl)furan by the Sonogashira reaction.View full abstractDownload PDF (55K)
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