Faculty Profiles - HARADA Emiko

Papers - HARADA Emiko

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Differential expression of genes encoding enzymes involved in sulfur assimilation pathways in response to wounding and jasmonate in Arabidopsis thaliana Reviewed

Harada E., Kusano T., Sano H.

Journal of Plant Physiology 156 ( 2 ) 272 - 276 2000.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Journal of Plant Physiology

Effects of mechanical wounding on levels of transcripts encoding enzymes involved in the sulfur assimilation pathway were examined. RNA blot hybridization showed the sulfate transporter, ATP sulfurylase, adenosine phosphosulfate (APS) kinase, APS reductase and cysteine synthase, all but the first being chloroplastic isozymes differentially responding to wounding, and also to jasmonate, a powerful inducer of wound responsive gene expression. When plants were exposed to jasmonate, transcripts for APS kinase were increased within 1 h after treatment, while those for APS reductase were increased after 3 h. We also found the glucosinolate content to be 2-fold elevated at the latter time point. APS is directed to the secondary metabolic pathway by APS kinase, so that glucosinolates are synthesized, while it is allotted through the action of APS reductase to the primary metabolic pathway by which cysteine is synthesized. Consequently, our results suggest that wounded plants primarily deliver available sulfur to synthesize defense-related substances by activating genes involved in the secondary metabolic pathway.

DOI： 10.1016/S0176-1617(00)80317-X

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Differential Accumulation of Transcripts Encoding Sulfur Assimilation Enzymes upon Sulfur and/or Nitrogen Deprivation in Arabidopsi Reviewed

Yamaguchi Y., Nakamura T., Harada E., Koizumi N., Sano H.

Bioscience, Biotechnology and Biochemistry 63 ( 4 ) 762 - 766 1999.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Bioscience, Biotechnology and Biochemistry

Expression of nine genes encoding enzymes involved in the sulfur assimilation pathway was examined by RNA blot hybridization. Significantly increased levels of transcripts encoding ATP sulfurylase and APS reductase were apparent under sulfur deprivation. However, in the absence of nitrogen, their responsiveness to sulfur deprivation was markedly reduced. Results suggest that the sulfur assimilation pathway is regulated at the transcriptional level by both nitrogen and sulfur sources. © 1999, Taylor & Francis Group, LLC. All rights reserved.

DOI： 10.1271/bbb.63.762

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Quantitative determination of constituents in various licorice roots by means of high performance liquid chromatography Reviewed

Kitagawa I., Chen W., Taniyama T., Harada E., Hori K., Kobayashi M., Ren J.

Yakugaku Zasshi 118 ( 11 ) 519 - 528 1998.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Yakugaku Zasshi

During the course of our studies on the chemical constituents of botanically identified Chinese licorice roots of various origins, we have identified 15 kinds of saponins and 49 kinds of flavonoids (including flavonoid glycosides). With these chemical constituents at hand, we have carried out the chemical evaluation studies of licorice roots available in Japan by means of high performance liquid chromatography (HPLC). In the HPLC analysis using an ODS reversed-phase column, a combination of 1% aqueous acetic acid and acetonitrile was used as the mobile phase in a gradient solvent system, and the eluate was monitored with UV absorption at 254 nm (for saponins with a diene or a conjugated carbonyl moiety, liquiritin, and liquiritin apioside) or at 350 nm (for other flavonoid constituents). By our analytical method described here, quantitative analyses of saponin and flavonoid constituents were effected simultaneously. We have found an interesting piece of information concerning the origin of parent plants and their characteristic constituents such as saponins and flavonoids.

DOI： 10.1248/yakushi1947.118.11_519

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Bioactive saponins and glycosides. VI. Elatosides A and B, potent inhibitors of ethanol absorption, from the bark of Aralia elata SEEM. (Araliaceae): The structure-requirement in oleanolic acid glucuronide- saponins for the inhibitory activity Reviewed

Yoshikawa M., Murakami T., Harada E., Murakami N., Yamahara J., Matsuda H.

Chemical and Pharmaceutical Bulletin 44 ( 10 ) 1915 - 1922 1996.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

Potent inhibitors of ethanol absorption, elatosides A and B, were isolated from the bark of Aralia elata SEEM. through bioassay-guided separation together with elatosides C and D and four known oleanolic acid glucuronide-saponins, spinasaponin A, spinasaponin A 28-O-glucoside, and stipuleanosides R1 and R2. The structures of elatosides A, B, C, and D were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-{[β-D-xylopyranosyl (1→2)] [β-D-galactopyranosyl (1→3)]}-β- D-glucopyranosiduronic acid, oleanolic acid 3-O-{[β-D-galactopyranosyl (1- 2)] [β-D-galactopyranosyl (1-3)]}-β-D-glucopyranosiduronic acid, and their 28-O-glucopyranosyl esters, respectively. The inhibitory effect of various oleanolic acid 3, 28-O-bisdesmosides, oleanolic acid 3-O-monodesmosides, and oleanolic acid on ethanol absorption was examined and it was found that the 3-O-glucuronide moiety and the 28-carboxyl group in oleanolic acid glucuronide-saponin were required to exert the inhibitory activity.

DOI： 10.1248/cpb.44.1915

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Bioactive saponins and glycosides. VII. On the hypoglycemic principles from the root cortex of Aralia elata SEEM.: Structure related hypoglycemic activity of oleanolic acid oligoglycoside Reviewed

Yoshikawa M., Murakami T., Harada E., Murakami N., Yamahara J., Matsuda H.

Chemical and Pharmaceutical Bulletin 44 ( 10 ) 1923 - 1927 1996.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

The hypoglycemic component, elatoside E, was isolated from the root cortex of Aralia elata SEEM. (Araliaceae) together with elatoside F and eight known oleanolic acid glycosides, elatosides A and C, oleanolic acid 3-O-[α- L-arabinofuranosyl (1→4)]-β-D-glucopyranosiduronic acid, oleanolic acid 3- O-β-D-glucopyranosiduronic acid, stipuleanosides R1 and R2, and chikusetsusaponins IV and IVa. The structures of elatosides E and F were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-[β-D-xylopyranosyl (1→2)][β-D-glucopyranosyl (1→3)]-α-L- arabinopyranoside and its 28-O-β-D-glucopyranosyl ester, respectively. The hypoglycemic activity of oleanolic acid and nine oleanolic acid oligoglycosides from the root cortex of Aralia elata was determined by monitoring inhibition effect on the elevation of plasma glucose level by oral sucrose tolerance test in rats, and some structure-activity relationships of oleanolic acid glycoside were obtained.

DOI： 10.1248/cpb.44.1923

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Antioxidant constituents from the fruit hulls of mangosteen (Garcinia mangostana L.) originating in Vietnam Reviewed

Yoshikawa M., Harada E., Miki A., Tsukamoto K., Si Qian Liang, Yamahara J., Murakami N.

Yakugaku Zasshi 114 ( 2 ) 129 - 133 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Yakugaku Zasshi

In the course of our search for natural antioxidants, the methanol extract of the fruit hulls of mangosteen (Garcinia mangostana L.) originating in Vietnam was found to exhibit a potent radical scavenging effect. By monitoring the radical scavenging effect, two xanthones, α- and γ- mangostins, were isolated together with (-)-epicatechin, procyanidins A-2 and B-2 as active principles. The antioxidative activity of these two xanthones was measured by the ferric thiocyanate method and it was found that γ- mangostin showed more potent antioxidative activity than BHA and α- tocopherol.

DOI： 10.1248/yakushi1947.114.2_129

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Quantitative analysis of dihydroisocoumarin constituents of Hydrangeae Dulcis Folium by means of high performance liquid chromatography. Chemical characterization of the processing, distribution in plant, and seasonal fluctuation Reviewed

Yoshikawa M., Chatani N., Harada E., Nishino Y., Yamahara J., Murakami N.

Yakugaku Zasshi 114 ( 3 ) 176 - 181 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Yakugaku Zasshi

In order to characterize the chemical change of the constituents during the processing of Hydrangeae Dulcis Folium, quantitative analyses of phyllodulcin, hydrangenol, and their 8-O-glucosides were developed by means of high performance liquid chromatography. As an application of this HPLC method, the distribution of those dihydroisocoumarins in different parts of Hydrangea macrophylla var. thunbergii was investigated. It was found that these dihydroisocoumarins were contained at the highest concentration in the leaves. Furthermore, the seasonal fluctuation of these compounds in the leaves, together with the height of the plant and total dry weight of the leaves, were clarified and so that, the suitable period for the harvest of Hydrangea macrophylla var. thunbergii was deduced to be from Oct. to Nov.

DOI： 10.1248/yakushi1947.114.3_176

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Escins-ia ib, iia, iib, and iiia, bioactive triterpene oligoglycosides from the seeds of aesculus hippocastanum L.: Their inhibitory effects on ethanol absorption and hypoglycemic activity on glucose tolerance test Reviewed

Yoshikawa M., Harada E., Murakami T., Matsuda H., Wariishi N., Yamahara J., Murakami N.

Chemical and Pharmaceutical Bulletin 42 ( 6 ) 1357 - 1359 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

Five triterpene oligoglycosides named escins-Ia, Ib, IIa, IIb, and IIIa were isolated from the seeds of Aesculus hippocastanum L. and their chemical structures were determined on the basis of chemical and physicochemical evidence. Escins-Ia, Ib, IIa, and lib were found to exhibit inhibitory effect on ethanol absorption and hypoglycemic activity on oral glucose tolerance test in rats. Among them, escins-IIa and IIb showed the higher activities for both bioassays, while desacylescins-I and II had no activity. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.42.1357

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Elatoside E, A New Hypoglycemic Principle From the Root Cortex of Aralia Elata Seem.: Structure-Related Hypoglycemic Activity of Oleanolic Acid Glycosides Reviewed

Yoshikawa M., Matsuda H., Harada E., Murakami T., Wariishi N., Yamahara Y., Murakami N., Johji J.

Chemical and Pharmaceutical Bulletin 42 ( 6 ) 1354 - 1356 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

A new inhibitor named elatosides E (which was shown to affect the elevation of plasma glucose level by oral sugar tolerance test in rats) was isolated from the root cortex of Aralia elata Seem, together with elatoside F. The structures of elatosides E and F were elucidated on the basis of chemical and physicochemical evidence. The hypoglycemic activities of oleanolic acid and nine oleanolic acid glycosides obtained from the root cortex of Aralia elata have been examined, and some structure-activity relationships have been found. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.42.1354

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Development of Bioactive Functions in Hydrangeae Dulcis Folium. On the Antiallergic and Antimicrobial Principles of Hydrangeae Dulcis Folium. (1). Thunberginols A, B, and F Reviewed

Yoshikawa M., Harada E., Naitoh Y., Inoue K., Matsuda H., Shimoda H., Yamahara J., Murakami N.

Chemical and Pharmaceutical Bulletin 42 ( 11 ) 2225 - 2230 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

From the less polar fraction of Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla Seringe var. thunbergii Makino, eight antiallergic and antimicrobial principles were isolated together with several known compounds. Among the newly isolated bioactive constituents, the chemical structures of thunberginols A, B, and F have been determined on the basis of chemical and physicochemical evidence. Thunberginols A, B, and F were found to exhibit more potent antiallergic activity than phyllodulcin, hydrangenol, disodium cromoglycate (DSCG), and tranilast. In addition, these thunberginols showed antimicrobial activity against oral bacteria. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.42.2225

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Development of bioactive functions in Hydrangeae Dulcis Folium. II. Antiulcer, antiallergy, and cholagoic effects of the extract from hydrangeae dulcis folium Reviewed

Yamahara J., Matsuda H., Shimoda H., Ishikawa H., Kawamori S., Wariishi N., Harada E., Murakami N., Yoshikawa M.

Yakugaku Zasshi 114 ( 6 ) 401 - 413 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Yakugaku Zasshi

In order to develop new bioactive functions of Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla Seringe var. thunbergii Makino, effects of the methanolic extract from the crude drug on antiulcer, antiallergic, cholagoic, and various pharmacological actions were investigated. Consequently, the methanolic extract was found to exhibit potent antiulcer, antiallergic, and cholagoic activities. By monitoring with these activities, it was found that the active constituents were contained in the lipophilic portion of the methanolic extract. Furthermore, the known lipophilic constituents such as phyllodulcin and hydrangenol were found to show little antiulcer and cholagoic activities, while it was also found that they showed antiallergic activity on Schultz-Dale reactions.

DOI： 10.1248/yakushi1947.114.6_401

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Chemical transformation from dihydroisocoumarin into benzylidene-phthalide by use of regiospecific oxidative lactonization mediated by copper chloride (II) - syntheses of thunberginol f and hydramacrophyllol A and B Reviewed

Yoshikawa M., Harada E., Yagi N., Okuno Y., Murakami N., Muraoka O., Aoyama H.

Chemical and Pharmaceutical Bulletin 42 ( 3 ) 721 - 723 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

Oxidative lactonization of 2-carboxystilbene mediated by CuCl2 proceeded regiospecifically to give the five-membered lactone. By utilizing this lactonization as a key reaction, chemical transformation from dihydroisocoumarine into benzylidencphthalide was accomplished, and it was applied to structural elucidation of two new phthalide, hydramacroohyllols A and B. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.42.721

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Camelliasaponins B<inf>1</inf>,B<inf>2</inf>,C<inf>1</inf> and C<inf>2</inf>, new type inhibitors of ethanol absorption in rats from the seeds of camellia japonica l Reviewed

Yoshikawa M., Harada E., Murakami T., Matsuda H., Yamahara J., Murakami N.

Chemical and Pharmaceutical Bulletin 42 ( 3 ) 742 - 744 1994.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

New type inhibitors of ethanol absorption, camelliasaponins B1, B2, C1 and C2, were isolated from the seeds of Camellia japonica L. The structures of camelliasaponins were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effect of camelliasaponins and related saponins on ethanol absorption have been examined, and it was found that the triterpene oligoglycoside structure having an acyl group was essential to exerting the activity. © 1994, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.42.742

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Absolute Stereostructures of Paeonisuffrone and Paeonisuffral Two New Labile Monoterpenes, from Chinese Moutan Cortex Reviewed

Yoshikawa M., Harada E., Kawaguchi A., Yamahara J., Murakanii N., Kitagawa I.

Chemical and Pharmaceutical Bulletin 41 ( 3 ) 630 - 632 1993.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

Two new labile monoterpenes named paeonisuffrone and paeonisuffral were isolated from Chinese Moutan Cortex, the dried root of Paeonia suffruticosa ANDREWS. The absolute stereostructures of paeonisuffrone and paeonisuffral were elucidated on the basis of chemical and physicochemical evidence which included the application of a modified Mosher’s method and lipase catalyzed debenzoylation. © 1993, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.41.630

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Indonesian Medicinal Plants. VI. On the Chemical Constituents of the Bark of Picrasma javanica bl. (Simaroubaceae) from Flores Island. Absolute Stereostructures of Picrajavanins A and B Reviewed

Yoshikawa M., Harada E., Aoki S., Yamahara J., Murakami N., Shibuya H., Kitagawa I.

Chemical and Pharmaceutical Bulletin 41 ( 12 ) 2101 - 2105 1993.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

Two new quassinoids named picrajavanins A and B were isolated, together with known β-carboline alkaloids and picrasidine G, from the bark of Picrasma javanica bl. (Simaroubaceae), an Indonesian folk medicine, collected on Flores Island. The absolute stereostructures of picrajavanins A (6) and B (7) have been elucidated on the basis of chemical and physicochemical evidence, together with the application of the modified Mosher’s method. © 1993, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.41.2101

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Elatosides a and b, Potent inhibitors of ethanol absorption in rats from the bark of aralia elata seem. : The structure-activity relationships of oleanolic acid oligoglycosides Reviewed

Yoshikawa M., Harada E., Matsuda H., Murakami T., Yamahara J., Murakami N.

Chemical and Pharmaceutical Bulletin 41 ( 11 ) 2069 - 2071 1993.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

By monitoring the inhibitory effect on ethanol absorption in rats, new active saponins named elatosides A and B were isolated from the bark of Aralia elata seem, together with elatosides C and D. The structures of elatosides A, B, C, and D were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of several oleanolic acid oligoglycosides on ethanol absorption have been examined and some structure-activity relationships have been found. © 1993, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.41.2069

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Thunberginols a, b, and f, new antiallergic and antimicrobial principles from hydrangeae dulcis folium Reviewed

Yoshikawa M., Uchida E., Chatani N., Murakami N., Yamahara J.

Chemical and Pharmaceutical Bulletin 40 ( 11 ) 3121 - 3123 1992.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

Six new antiallergic and antimicrobial principles, thunberginols A, B, C, D, E, and F, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The chemical structures of thunberginols A, B, and F have been determined on the basis of chemical and physicochemical evidence. Thunberginols A, B, and F showed more potent antiallergic activity than phyllodulcin, hydrangenol, and AA-861 in the in vitro test using the Schults-Dale reaction in sensitized guinea pig bronchial muscle. Thunberginols A, B, and F also exhibited antimicrobial activity against oral bacteria. © 1992, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.40.3121

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Thunberginols C, D, and E, New Antiallergic and Antimicrobial Dihydroisocoumarins, and Thunberginol G 3’-0-gluc0side and (-)-hydrangenol 4’-0-glucoside New Dihydroisocoumarin Glycosides, From Hydrangeae Dulcis Folium Reviewed

Yoshikawa M., Uchida E., Chatan N., Kobayash H., Naitoh Y., Murakami I., Matsuda H., Okunc Y.

Chemical and Pharmaceutical Bulletin 40 ( 12 ) 3352 - 3354 1992.1

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical and Pharmaceutical Bulletin

New antiallergic and antimicrobial dihydroisocoumarins, thunberginols C, D, and E, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO, together with new dihydroisocoumarin glycosides, thunberginol G 3’-0-glucoside and (-)-hydrangenol 4’-0-glucoside. Their chemical structures have been determined on the basis of chemical and physicochemical evidence. Thunberginols C, D, E, G, and (-)-hydrangenol 4’-0-glucoside showed antiallergic activity in the in vitro bioassay using the Schults-Dale reaction in sensitized guinea pig bronchial muscle, and they also exhibited antimicrobial activity against oral bacteria. © 1992, The Pharmaceutical Society of Japan. All rights reserved.

DOI： 10.1248/cpb.40.3352

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