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Juziro Nishijo, Shiho Moriyama, Sachiko Shiota, Miyoko Kamigauchi, Mak ...
2004 Volume 52 Issue 12 Pages
1405-1410
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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The interaction of cholesterol with heptakis (2,3,6-tri-
O-methyl)-β-cyclodextrin (TOM-β-CyD) was investigated in water using solubility method. It was found that TOM-β-CyD forms two kinds of soluble complexes, with molar ratios of 1 : 1 and 1 : 2 (cholesterol : TOM-β-CyD). The thermodynamic parameters for 1 : 1 and 1 : 2 complex formation of cholesterol with TOM-β-CyD were: Δ
G01 : 1=−11.0 kJ/mol at 25 °C (
K1 : 1=7.70×10
M−1); Δ
H01 : 1=−1.28 kJ/mol;
TΔ
S01 : 1=9.48 kJ/mol; Δ
G01 : 2=−27.8 kJ/mol at 25 °C (
K1 : 2=7.55×10
4 M−1); Δ
H01 : 2=−0.57 kJ/mol;
TΔ
S01 : 1=27.3 kJ/mol. The formation of the 1 : 2 complex occurred much more easily than that of the 1 : 1 complex. The driving force for 1 : 1 and 1 : 2 complex formation was suggested to be exclusively hydrophobic interaction. Based on the measurements of proton nuclear magnetic resonance spectra and studies with Corey–Pauling–Koltun atomic models, the probable structures of the 1 : 2 complex were estimated. In addition, the interaction of TOM-β-CyD with cholesterol was compared with that of heptakis (2,6-di-
O-methyl)-β-CyD (DOM-β-CyD). The interaction of TOM-β-CyD is more hydrophobic than that of DOM-β-CyD, and the life time of the complexed TOM-β-CyD is sufficiently long to give separated signals, at the NMR time scale, which differs from that of complexed DOM-β-CyD.
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Vakhtang Mshvildadze, Riad Elias, Robert Faure, David Rondeau, Laurent ...
2004 Volume 52 Issue 12 Pages
1411-1415
Published: 2004
Released on J-STAGE: December 01, 2004
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Five new triterpenoid saponins, pastuchoside A (1), B (3), C (5), D (7) and E (9), were isolated from the leaves of
Hedera pastuchowii. They have oleanolic acid or hederagenin as aglycone. The structures were established by NMR spectroscopy including gs (gradient selected)-COSY, gs-HSQC, gs-HSQC-TOCSY and gs-HMBC experiments, and mass spectrometry ( ESI-HR-MS). Heptaoside saponins, compounds 1 and 3, are described for the first time in the genus
Hedera.
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Junji Mukai, Yohko Miyanaga, Toshihiko Ishizaka, Kiyokazu Asaka, Yuka ...
2004 Volume 52 Issue 12 Pages
1416-1421
Published: 2004
Released on J-STAGE: December 01, 2004
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The purpose of this study was to evaluate quantitatively the taste of the various total enteral nutrients marketed in Japan using human gustatory sensation tests and an artificial taste sensor. In the human gustatory sensation test, four basic taste intensities (sweetness, saltiness, sourness, and bitterness), as well as 15 kinds of palatability scales, were evaluated according to the semantic differential (SD) method. Among 15 palatability items, the item; difficult to drink/easy to drink, was adopted as an overall palatability since it shows the highest factor loading by factor analysis. The overall palatability was found to be highly positively correlated with sweetness and sourness, but negatively correlated with bitterness and saltiness. Addition of a flavour to the amino acid-based enteral nutrient Aminoleban
®EN significantly improved its palatability. This effect is presumably due to sour components of the flavour, such as citric acid, which reduce the bitterness intensity of branched-chain amino acids in the product. The sweetness and sourness intensities predicted by the taste sensor showed a high correlation with the results obtained in the human gustatory sensation tests. The taste sensor was able to predict the overall palatability of the total enteral nutrients with high accuracy. The products could be classified into three groups (peptide-based, amino-acid-based, and protein-based) by principal component analysis using sensor output of 8 channels. The products could be also classified into four groups; peptide-based, amino-acid-based, and protein-based and flavor addition group by principal component analysis using sensor output of channels 1, 3, 4 and 7, which are specific to basic tastes. The taste sensor could therefore be useful in predicting the taste or palatability of total enteral nutrients, and could contribute to attempts to improve compliance for such products and for enteral nutrients.
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Tun-Cheng Chien, Chien-Shu Chen, Fang-Hwa Yu, Ji-Wang Chern
2004 Volume 52 Issue 12 Pages
1422-1426
Published: 2004
Released on J-STAGE: December 01, 2004
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4-Amino-1-(β-
D-ribofuranosyl)quinazolin-2-one (3) was prepared by a direct glycosylation of 4-aminoquinazolin-2-one (7) using the Vorbruggen's silylation method and provided exclusively the β-anomer. This quinazoline nucleoside and its 2′,3′-
O-isopropylidene derivative (9) did not undergo the coupling reaction with dialkyl disulfides in the presence of tri-
n-butylphosphine unless their 4-amino groups were protected by
N,
N-dimethylaminomethylidene. This approach provides a viable alternative synthetic route to 5′-alkylthio-5′-deoxy nucleosides.
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Tatsuya Takagi, Yukiko Makino, Yuko Tanaka, Kousuke Okamoto, Noriyuki ...
2004 Volume 52 Issue 12 Pages
1427-1432
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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Recently, profiling the chemical substances in illegally distributed drugs has been needed in order to reveal the drug channels. However, this kind of profiling is often difficult because such drugs contain various kinds of impurities and the quantity of these impurities changes. Due to these circumstances, several methods, including a slightly revised ICA (Independent Component Analysis) by a Hebbian learning artificial neural network, were applied for profiling illegally distributed methamphetamine. Eventually, better classification results with the ICA than with other methods were obtained. These results show that ICA could make it easier to profile illegally distributed methamphetamine.
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Pierre Alexandre dos Santos, Maria Fernanda Castro Amarante, Ana Maria ...
2004 Volume 52 Issue 12 Pages
1433-1435
Published: 2004
Released on J-STAGE: December 01, 2004
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This work reports for the first time the production a furanoheliangolide (goyazensolide) by plant cell culture. Monitoring of the goyazensolide metabolism revealed that the maximum production occurred during the lag phase of the
Lychnophora ericoides callus culture. The antiproliferative activity of obtained goyazensolide was evaluated against seven cancer cell lines using MTT assay. The results revealed a potent cytotoxic activity for the furaheliangolide with IC
50 values in the range of 0.06 μg/ml for CEM leukemia cells to 0.75 μg/ml for B16 melanome cells.
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Mourboul Ablise, Brigitte Leininger-Muller, Choi Dal Wong, Géra ...
2004 Volume 52 Issue 12 Pages
1436-1439
Published: 2004
Released on J-STAGE: December 01, 2004
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Five glycyrrhetinic acid (Ib) derivatives have been synthesized to try to improve the antioxidant activity. Their
in vitro antioxidant activities were studied using a cytochrome P450/NADPH reductase system from rat liver microsomes. The generation of microsomal free radicals was followed by oxidation of the DCFH-DA probe, while evaluating the capacity to inhibit reactive oxygen species (ROS) formation. Two hydroxylated derivatives, 18β-olean-12-ene-3β,11α,30-triol (II) and 18β-olean-12-ene-3β,11β,30-triol (IV), exhibited strong antioxidant activities. At a concentration of 1.0 mg/ml, these derivatives inhibited ROS formation by 50% and 51%, respectively. Moreover, two homo- and heterocyclic diene derivatives, 18β-olean-11,13(18)-diene-3β,30-diol (III) and 18β-olean-9(11),12-diene-3β,30-diol (V), were also effective in ROS-scavenging activity (inhibition of 41% and 44% of ROS activity, respectively). In the same conditions, the lead compound (Ib) and the reference vitamin E inhibited ROS activity by 31% and 32%, respectively. Our results suggest that the chemical reduction of the 11-keto and 30-carboxyl groups into hydroxyl function (example, II, IV) can increase the antioxidant activity of Ib significantly. In view of these results, our study represents a further approach to the development of potential therapeutic agents from Ib derivatives for use in pathologic events in which, free radical damage could be involved.
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Feng Yin, Lihong Hu, Ruixiang Pan
2004 Volume 52 Issue 12 Pages
1440-1444
Published: 2004
Released on J-STAGE: December 01, 2004
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Three new dammarane glycosides (1—3), together with five known compounds, gypenoside LXIX (4), gylongiposide I (5), gypenoside XLVIII (6), allantion (7) and vitexin (8) were isolated from the MeOH extract of the aerial parts of
Gynostemma pentaphyllum. Compounds 5, 7, and 8 were isolated from this plant for the first time. Their structures were elucidated by 1D and 2D NMR spectra interpretation as well as by chemical degradation.
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Toshiaki Morimoto, Kiyoshi Yoshikawa, Masanao Murata, Naoko Yamamoto, ...
2004 Volume 52 Issue 12 Pages
1445-1450
Published: 2004
Released on J-STAGE: December 01, 2004
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Axially chiral biphenyldiphosphine ligands bearing diphenylphosphino group(s) and/or dicyclohexylphosphino group(s) were prepared in enantiomerically pure form starting from 2,6-dimethylnitrobenzene
via 8 steps: iodination, reduction, methoxylation through diazotization, Ullmann coupling, bromination, phosphorylation, optical resolution, and silane reduction, and the obtained ligands were used in rhodium-catalyzed asymmetric hydrogenation.
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Takeru Kohinata, Mitsuo Fujii, Souichiro Nakamura, Noritaka Hamada, Et ...
2004 Volume 52 Issue 12 Pages
1451-1457
Published: 2004
Released on J-STAGE: December 01, 2004
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We investigated a method to quantitatively determine amorphous nicardipine hydrochloride (NIC) in the NIC-long acting formula (LA) model formulas prepared using NIC, light anhydrous silicic acid (LASA) and carboxymethylethylcellulose (CMEC). Consequently, since the quantity of total NIC in the formula can be determined by means of HPLC and crystal NIC can be determined by the differential scanning calorimetry (DSC) method because the heat of fusion (85.08 J/g) of NIC is constant and unaffected by excipients, we developed the HPLC-DSC method by which the quantity of amorphous NIC is calculated as the difference between the quantity of total NIC determined by HPLC and the quantity of crystal NIC determined by DSC. This practical HPLC-DSC method was confirmed to have good accuracy and reproducibility.
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Viqar Uddin Ahmad, Farman Ullah, Javid Hussain, Umar Farooq, Muhammad ...
2004 Volume 52 Issue 12 Pages
1458-1461
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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A new coumarinolignoid 8′-epi-cleomiscosin A (1) together with the new glycoside 8-
O-β-
D-glucopyranosyl-6-hydroxy-2-methyl-4
H-1-benzopyrane-4-one (2) have been isolated from the aerial parts of
Rhododendron collettianum and their structures determined on the basis of spectroscopic evidences. Tyrosinase inhibition study of these compounds and their structure–activity relationship (SAR) were also investigated. The compounds exhibited potent to mild inhibition activity against the enzyme. Especially, the compound 1 showed strong inhibition (IC
50=1.33 μ
M) against the enzyme tyrosinase, as compared to the standard tyrosinase inhibitors kojic acid (IC
50=16.67 μ
M) and
L-mimosine (IC
50=3.68 μ
M), indicating its potential used for the treatment of hyperpigmentation associated with the high production of melanocytes.
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Tatjana Kundakovic, Nikolas Fokialakis, Prokopios Magiatis, Nada Kovac ...
2004 Volume 52 Issue 12 Pages
1462-1465
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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Investigation of the aerial parts of
Achillea alexandri-regis led to the identification of 19 chemical constituents: twelve 3-
O-fatty acid esters of triterpene alcohols arnidiol (1—4), maniladiol (5—8) and 16β-hydroxylupeol (9—12), α-amyrin, β-amyrin, β-sitosterol, 3,4-
O-dicaffeoyl quinic acid, cinnamic acid, pinoresinol-β-
D-glucoside and rutin. Among them, compounds 3, 4, 8, 11 and 12 are new natural products. The structures of all compounds have been elucidated on the basis of their spectral and chemical data.
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Mi-Ran Kim, Hyung-In Moon, Jin Ho Chung, Young Hee Moon, Kyung-Soo Hah ...
2004 Volume 52 Issue 12 Pages
1466-1469
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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A bioassay-guided fractionation of the ethyl acetate soluble fraction from the stem bark of
Styrax japonica S.
et Z. (Styracaceae) yielded two new lignan compounds, styraxjaponoside A (1) and styraxjaponoside B (2), along with three known compounds, matairesinoside (3), egonol glucoside (4), and dihydrodehydrodiconiferyl alcohol 9′-
O-glucoside (5). The structures of compounds 1—5 were determined by spectroscopic method, as well as 1D- and 2D-NMR (HSQC,
1H–
1H COSY, and HMBC) spectroscopy. Among them, compound 2 exhibited potent inhibitory activity against matrix metalloproteinase (MMP)-1, and prevented the UV-induced changes in the MMP-1 expression. In addition, compounds 3 and 5 were isolated from this plant for the first time.
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Bunji Uno, Noriko Okumura
2004 Volume 52 Issue 12 Pages
1470-1472
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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The tosylation reaction of endocrine-disruptive alkylphenolic compounds in a solid-phase aqueous system was investigated with the aim of developing an environment-friendly and efficient derivatization method for HPLC analyses of environmental samples. The phenols were rapidly and efficiently converted to the tosyl derivatives on a commercially available ODS solid-phase cartridge by passing an aqueous buffer solution through it. The solid-phase aqueous tosylation system has been incorporated into a preconcentration step performed by solid-phase extraction from environmental water.
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Boppana Deepa, Natesan Balasubramanian, Karachalacherevu Seetharamiah ...
2004 Volume 52 Issue 12 Pages
1473-1475
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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A sensitive spectrophotometric method for the determination of hydroxylamine is described. The method is based on the oxidation of hydroxylamine to nitrite using sodium arsenate under alkaline condition. The formed nitrite is determined based on the diazo coupling reaction between
p-nitroaniline and
N-(1-naphthyl)ethylenediamine dihydrochloride [NEDA]. The system obeys Beer's law over the concentration range 0—7 μg of hydroxylamine at 545 nm and the colour is stable for 3 h. The molar absorptivity of the colour system is found to be 6.7×10
4 l mol
−1 cm
−1. The relative standard deviation is 1.2% for ten determinations at 4 μg of hydroxylamine. Interferences due to various foreign ions have been studied and the method has been applied to the determination of hydroxylamine and its derivatives used in pharmaceutical formulations after hydrolysis.
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Shu-Hua Qi, Si Zhang, Zhi-Hui Xiao, Jian-She Huang, Jun Wu, Qing-Xin L ...
2004 Volume 52 Issue 12 Pages
1476-1478
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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A new steroidal glycoside—4′-
O-acetyl-3-
O-[β-
D-arabino-pyranosyl-oxy]-cholest-5-ene-3β,19-diol (1), and a new glycerol derivative—1,2-
O-[2′-hydroxyoctadecyl]-glycerol (2), along with 16 known compounds were isolated from the EtOH/CH
2Cl
2 extracts of the South China Sea gorgonian coral
Junceella juncea. The structures of 1 and 2 were established by extensive spectroscopic analysis, including 1D and 2D NMR data.
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Kiyoshi Ikeda, Yuko Ishii, Koji Konishi, Masayuki Sato, Kiyoshi Tanaka
2004 Volume 52 Issue 12 Pages
1479-1482
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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Peptide mimics derived from the first extracellular loop of CCR5 bearing non-peptide spacers in place of Ala-Ala-Ala sequence in the peptide moiety were synthesized, and the effects of these compounds on the inhibition against HIV-1 were examined. Compound 2b having
m-aminophenoxyacetic acid derivative as a non-peptide spacer significantly inhibited HIV-1.
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Kai Sun, Xian Li, Wen Li, Jinhui Wang, Jianming Liu, Yi Sha
2004 Volume 52 Issue 12 Pages
1483-1486
Published: 2004
Released on J-STAGE: December 01, 2004
JOURNAL
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Two new lactones (1, 2), descurainolide A and B, and one new aryl-8-oxa-bicyclo[3,2,1]-oct-3-en-2-one (3), descurainin, together with five known compounds (4—8), were isolated from the seeds of
Descurainia sophia (L.) W
EBB ex P
RANTL. The structures of the new compounds were elucidated by extensive studies of their 1D, 2D NMR and HR-MS. Compounds 4 and 5 showed cytotoxicity.
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Rodrigo Rezende Kitagawa, Maria Stella Gonçalves Raddi, Lourdes ...
2004 Volume 52 Issue 12 Pages
1487-1488
Published: 2004
Released on J-STAGE: December 01, 2004
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Quinones constitute an important class of naturally occurring compounds. They are found in plants, fungi and bacteria. Large number of quinones has been associated with antitumor, antibacterial, antimalarial and antifungal activities. In this work we describe the isolation, structure determination and the cytotoxic index of a new 1,4-naphthoquinone isolated from the capitula of
Paepalanthus latipes.
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Gaolin Liang, Kejun Cheng, Hong Zhou, Changqi Hu
2004 Volume 52 Issue 12 Pages
1489-1491
Published: 2004
Released on J-STAGE: December 01, 2004
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Two new phase I metabolites of phytoestrogen kobophenol A (1), called koboquinone A (2) and B (3), have been isolated from the feces of rats orally administered 1. Their structures were determined by spectroscopic methods. 2 also showed activity of stimulating the proliferation of cultured osteoblasts.
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Fumiyuki Kiuchi, Kenji Matsuo, Michiho Ito, Tran Kim Qui, Gisho Honda
2004 Volume 52 Issue 12 Pages
1492-1494
Published: 2004
Released on J-STAGE: December 01, 2004
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Trypanocidal constituents of the fruits of
Vitex trifolia were investigated. Activity-guided isolation of the acetone extract resulted in the isolation of two new norditerpene aldehydes, 1 and 2, together with five known diterpenes: vitexifolin E (3), vitexifolin F (4), vitexilactone (5), 6-acetoxy-9-hydroxy-13(14)-labden-16,15-olide (6), and previtexilactone (7).
In vitro minimum lethal concentrations of the isolated compounds against epimastigotes of
Trypanosoma cruzi were 11 μ
M (1), 36 μ
M (2), 34 μ
M (3), 34 μ
M (4), 66 μ
M (5), 66 μ
M (6), and >265 μ
M (7).
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Fumiyuki Kiuchi, Kenji Matsuo, Michiho Ito, Tran Kim Qui, Gisho Honda
2004 Volume 52 Issue 12 Pages
1495-1496
Published: 2004
Released on J-STAGE: December 01, 2004
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Trypanocidal constituents of
Pogostemon cablin were investigated. Activity guided isolation of the acetone extract resulted in isolation of three new sesquiterpene hydroperoxides 1—3, together with a known sesquiterpene, patchouli alcohol (4).
In vitro minimum lethal concentrations of the hydroperoxides 1—3 against epimastigotes of
Trypanosoma cruzi were 0.84 μ
M (1), 1.7 μ
M (2) and 1.7 μ
M (3). The activity of the corresponding alcohols and patchouli alcohol was very weak (MLC>200 μ
M).
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Maurizio Bruno, Sergio Rosselli, Antonella Maggio, Franco Piozzi, Leon ...
2004 Volume 52 Issue 12 Pages
1497-1500
Published: 2004
Released on J-STAGE: December 01, 2004
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Two new neoclerodane diterpenoids, 6-deacetyl-teucrolivin A (5) and 8β-hydroxy-teucrolivin B (6), were isolated from the aerial parts of
Teucrium orientale, along with four already known neoclerodane diterpenoids, teucrolivin A (1), teucrolivin B (2), teucrolivin C (3) and teucrolivin H (4), previously isolated from
Teucrium oliverianum. Their structures were elucidated on the basis of spectroscopic evidence and chemical transformations. Compounds 1—3 were assayed for antifeedant activity against
Spodoptera littoralis,
S. frugiperda and
Heliocoverpa armigera. Teucrolivin A was the most potent of the three compounds tested.
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Mee Jung Jung, Sam Sik Kang, Yu Jung Jung, Jae Sue Choi
2004 Volume 52 Issue 12 Pages
1501-1503
Published: 2004
Released on J-STAGE: December 01, 2004
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From the stem bark of
Albizzia julibrissin D
URAZZ (Leguminosae), two new phenolic glycosides (albibrissinosides A and B) were isolated. Their structures were determined by spectroscopic analysis. The albibrissinoside B was found to be a radical scavenger on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.
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Ping-Jyun Sung, Mei-Ru Lin, Lee-Shing Fang
2004 Volume 52 Issue 12 Pages
1504-1506
Published: 2004
Released on J-STAGE: December 01, 2004
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A new trihydroxy briarane-related diterpenoid, junceellolide I (1), along with a known metabolite, (1
R,2
R,5
Z,7
R,8
S,9
R,10
R,12
R,14
R,17
S)-2,14-diacetoxy-8,17-epoxy-9,12-dihydroxybriara-5,11(20)-dien-19-one (2), have been isolated from the gorgonian coral
Junceella fragilis, collected off the southern Taiwan coast. The structure, including the relative configuration of the new compound 1, was elucidated by the combination of spectral data, particularly in high-resolution
1H- and
13C-NMR spectroscopy utilizing COSY, HMBC, HMQC, and NOESY experiments.
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Kenjiro Koga, Kumiko Takekoshi, Susumu Kawashima, Masakazu Taniguchi, ...
2004 Volume 52 Issue 12 Pages
1507-1510
Published: 2004
Released on J-STAGE: December 01, 2004
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One persistent problem with using therapeutic concentrations of glycyrrhizin (GZ) is that, at these high concentrations, it forms a gel in an aqueous solution. We previously solved this problem by dissolving GZ in a highly concentrated phosphate buffer. Unfortunately, the resulting GZ solution has a hyperosmotic pressure that renders it unsuitable for use in patients. The aim of this study was to prepare a highly concentrated GZ solution having an osmotic pressure ratio of 1 and a pH of 7.4. By adding small amounts of oil and using a 100 m
M phosphate buffer, we achieved an emulsified GZ solution that is stable at room temperature and has a physiological osmotic pressure and pH. When clove oil was used as an emulsifier, the gel formation temperature of GZ solution decreased appreciably compared to that of GZ solution without clove oil. Using scanning electron microscopy (SEM), we examined the detailed characteristics of GZ gels prepared from solutions with or without clove oil. SEM of cross sections of GZ gels revealed an irregular structure in gels prepared with clove oil, indicating that clove oil prevented the formation of the intermolecular GZ networks typically characterized by gels derived from pure GZ solutions.
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