Published Papers - TAKARA Kensaku

Odorous volatiles and methoxypyrazines responsible for the musty- peanut aroma in microwave-heated sponge gourd (Luffa cylindrica)

Asikin Yonathan, Tanahara Naoya, Maeda Goki, Tsuchida Eito, Hirose Naoto, Oe Moena, Takara Kensaku, Wada Koji

FOOD SCIENCE AND TECHNOLOGY RESEARCH ( 公益社団法人 日本食品科学工学会 )  27 ( 6 ) 933 - 938   2021.11 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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<p>Microwave heating results in the generation of odorous compounds in sliced sponge gourd (<i>Luffa cylindrica</i>). Herein, the odorous components of microwave-heated sponge gourd were extracted, and the volatiles were separated by a solvent-assisted flavor evaporation technique. Subsequently, gas chromatography (GC)–olfactometry analysis identified 10 compounds in the aroma extract including unsaturated aliphatic aldehydes (3-hexenal; 2-octenal), alcohols (3-hexen-1-ol; 1-octen-3-ol), and ketones (1-octen-3-one; 1,5-octadien-3-one), which might be responsible for the typical green-grassy and metallic characteristics. Microwave heating could also promote the nonenzymatic browning reaction in the softened gourd to release methional and 2-acetyl-1-pyrroline, which have boiled potato and roasted-peanut odors, respectively. Furthermore, preparative GC–mass spectrometry was used to distinguish two methoxypyrazines (3,5-dimethyl-2-methoxypyrazine and 3-isopropyl-2-methoxypyrazine) responsible for a highly noticeable, unpleasant musty-peanut aroma in heated sponge gourd. Moreover, 3-isopropyl-2-methoxypyrazine might also generate an unlikeable earthy odor, resulting an off-flavor, and thus could be used as one of quality markers in sponge gourd.</p>

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Anti-tyrosinase properties of different species of turmeric and isolation of active compounds from <i>Curcuma amada</i>

Akter Jesmin, Islam Md Zahorul, Hossain Md Amzad, Takara Kensaku

MEDICINAL CHEMISTRY RESEARCH ( Medicinal Chemistry Research )  30 ( 9 ) 1669 - 1676   2021.09 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Turmeric is traditionally used as a skin cosmetic in some religious and cultural occasions on the Indian subcontinent. In this study, we compared the tyrosinase inhibitory properties of four Curcuma spp., namely, C. xanthorrhiza, C. aromatica, C. amada, and C. zedoaria. Bioassay-guided isolation and purification of tyrosinase inhibitors using silica gel column and high-performance liquid chromatography. Structural identification of the compounds was conducted using 1H NMR, 13C NMR, and liquid chromatography-tandem mass spectrometry. C. amada showed the highest tyrosinase inhibitory activity, with an IC50 of 53.4 μg/mL. Therefore, it was chosen for the isolation and purification of tyrosinase inhibitors. The purified compounds were zederone (1), furanodienone (2), 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxyphenyl) heptanes (3), 3,5-dihydroxy-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl) heptanes (4) and 1,5-epoxy-3-hydroxy-1-(3,4-dihydroxy-5-methoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl) heptanes (5). The IC50 values for the mushroom anti-tyrosinase activity of compounds 1, 2, 3, 4, and 5 were 108.2, 89.2, 92.3, 21.7, and 41.3 µM, respectively. These compounds also inhibited intracellular tyrosinase activity, thus reducing melanin synthesis in B16F10 melanoma cells. Compound 4 showed significantly stronger anti-tyrosinase activity than that of arbutin (a positive control drug). No significant difference was observed in the tyrosinase inhibitory effect between compound 5 and arbutin. Our findings strongly suggest that C. amada is a promising source of natural tyrosinase inhibitors to prevent melanogenesis and could be used as a whitening cosmetic. [Figure not available: see fulltext.]

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Syringin: A Phenylpropanoid Glycoside Compound in Cirsium brevicaule A. GRAY Root Modulates Adipogenesis.

Hossin AY, Inafuku M, Takara K, Nugara RN, Oku H

Molecules (Basel, Switzerland) ( Molecules )  26 ( 6 )   2021.03 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Cirsium brevicaule A. GRAY is a wild perennial herb, and its roots (CbR) have traditionally been used as both food and medicine on the Japanese islands of Okinawa and Amami. The present study evaluated the antiadipogenic effect of CbR using mouse embryonic fibroblast cell line 3T3-L1 from JCRB cell bank. Dried CbR powder was serially extracted with solvents of various polarities, and these crude extracts were tested for antiadipogenic activity. Treatment with the methanol extract of CbR showed a significant suppression of lipid accumulation in 3T3-L1 cells. Methanol extract of CbR was then fractionated and subjected to further activity analyses. The phenylpropanoid glycosidic molecule syringin was identified as an active compound. Syringin dose dependently suppressed lipid accumulation of 3T3-L1 cells without cytotoxicity, and significantly reduced the expressions of peroxisome proliferator-activated receptor gamma, the master regulator of adipogenesis, and other differentiation markers. It was demonstrated that syringin effectively enhanced the phosphorylation of the AMP-activated protein kinase and acetyl-CoA carboxylase. These results indicate that syringin attenuates adipocyte differentiation, adipogenesis, and promotes lipid metabolism; thus, syringin may potentially serve as a therapeutic candidate for treatment of obesity.

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Phenolic constituents of sugarcane bagasse and juice extracts

Kensaku Takara, Tomoro Goeku, Yuki Higa, Asahiro Kamiya, Kiyoaki Miyasaka, Toshikazu Kawai

Food Preservation Science ( Japan Association of Food Preservation Scientists )  47 ( 1 ) 19 - 25   2021.01 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

Suitability of lactic acid bacteria for the production of pickled luffa (Luffa cylindrica Roem.)

Naoto Hirose, Goki Maeda, Naoya Tanahara, Kensaku Takara, Koji Wada

Food Science and Technology Research ( Japanese Society for Food Science and Technology )  27 ( 1 ) 57 - 61   2021.01 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Suitability of lactic acid bacteria for the production of pickled luffa (Luffa cylindrica Roem.)

Hirose N.

Food Science and Technology International, Tokyo ( 公益社団法人 日本食品科学工学会 )  27 ( 1 ) 57 - 61   2021 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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<p>In the present study, we examined the use of lactic acid bacteria as a starter for the production of pickled luffa. A starter culture of lactic acid bacteria was added to a brine containing 1% of glucose and NaCl that was used to make pickled luffa. Fermentation at 10 °C for 7 days resulted in an increase in the γ-aminobutyric acid content of pickled luffa in all the strains. In <i>Lactococcus lactis</i> NH-61, pickled luffa had good taste and its browning was suppressed. <i>Lactobacillus sakei</i> MMF-LS151 was excellent in regarding the acidity of brine, but led to the browning of pickled luffa. To the best our knowledge, this is the first report on the production of good tasting low-salt pickled luffa.</p>

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Phenolic Constituents of Sugarcane Bagasse and Juice Extracts

TAKARA Kensaku, GOEKU Tomoro, HIGA Yuki, KAMIYA Asahiro, MIYASAKA Kiyoaki, KAWAI Toshikazu

Food Preservation Science ( Japan Association of Food Preservation Scientists )  47 ( 1 ) 19 - 25   2021 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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<p> The phenolic constituents in three sugarcane extracts—bagasse extract (BE), bagasse hydrothermal extract (BHE), and sugarcane juice extract (SJE)—were studied for antioxidant properties using LC coupled to a photodiode array detector and an electrospray ionization mass spectrometer (ESI-MS). The LC-UV/MS chromatogram of the BE showed a signal similar to that of the BHE. Syringic acid (1), 4-hydroxybenzaldehyde (2), <i>p</i>-coumaric acid (3), vanillin (4), syringaldehyde (5), and ferulic acid (6) were detected in the BE and BHE, while the profile of SJE was different; only compounds 4 and 5 were detected in the SJE. In this work, we attempted to elucidate the chemical structure of an unknown peak in the spectrum of the BE. Subsequently, (4<i>E</i>) -3,5-bis (4-hydroxyphenyl) pent-4-enoic acid (7) was identified by a spectral investigation. These seven phenolic compounds were quantified by selective ion mass chromatography (SIM) using LC-MS, and the accumulated contents were 130.3, 105.2 and 1.4mg/g of dry weight in the BE, BHE, and SJE, respectively. Furthermore, each of the seven phenolics and three extracts was examined for antioxidative activity by measurement of the H-ORAC value. These values for the BE, BHE, and SJE were estimated to be 9319, 9417 and 9276 <i>μ</i>mol Trolox equivalent/g D.W., respectively. Therefore, the contributions of these seven phenolics to the H-ORAC values were 23.9% for BE, 24.5% for BHE and 0.3% for SJE of the total H-ORAC value.</p>

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Comparison of Analyzed and Calculated Values of Gamma-Aminobutyric Acid (GABA) Intake from Hospital Diet.

Ito S, Takara K, Shiroma K, Namihira C, Todoriki H

Journal of nutritional science and vitaminology ( 一般財団法人 学会誌刊行センター )  67 ( 2 ) 139 - 142   2021 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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<p>Intake of gamma-aminobutyric acid (GABA) from nutritionally controlled hospital diet was analyzed and compared with those estimated by calculation. Thirty meals provided at a hospital in Okinawa were sampled. GABA content per meal were measured by HPLC and calculated from GABA content data in foods as much as available. As a result, out of a total of 30 meals, only 49.3% of the weight of food that appeared in the meals could be calculated. The analyzed and calculated median daily GABA intake was 67.3 mg and 30.0 mg. Overall, the calculated values were lower than the analytical values, but there was a significant positive correlation (<i>r</i>_s=0.618, <i>p</i><0.001). The more complete the database on GABA content, the more accurate the GABA intake could be estimated by calculation.</p>

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Physicochemical, antioxidant, volatile component, and mass spectrometry‑based electronic nose analyses differentiated unrefined non‑centrifugal cane, palm, and coconut sugars

Monthana Weerawatanakorn, Yonathan Asikin, Sudthida Kamchonemenukool, Hajime Tamaki, Kensaku Takara, Koji Wada

Journal of Food Measurement and Characterization ( Springer )  15 ( 2 ) 1563 - 1577   2020.11 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Pharmacological activities of 4-methylene-8-hydroxybisabola-2,10-diene-9-one, a new compound isolated from Ryudai gold (Curcuma longa).

Akter J, Islam Z, Hossain A, Takara K

Naunyn-Schmiedeberg's archives of pharmacology ( Naunyn-Schmiedeberg's Archives of Pharmacology )  393 ( 2 ) 191 - 201   2020.02 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Endothelium-independent and calcium channel-dependent relaxation of the porcine cerebral artery by different species and strains of turmeric.

Akter J, Islam MZ, Hossain MA, Kawabata S, Takara K, Nguyen HTT, Hou DX, Miyamoto A

Journal of traditional and complementary medicine ( Journal of Traditional and Complementary Medicine )  9 ( 4 ) 297 - 303   2019.10 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Isolation and structural elucidation of antifungal compounds from Ryudai gold (Curcuma longa) against Fusarium solani sensu lato isolated from American manatee.

Akter J, Islam MZ, Takara K, Hossain MA, Sano A

Comparative biochemistry and physiology. Toxicology & pharmacology : CBP ( Comparative Biochemistry and Physiology Part - C: Toxicology and Pharmacology )  219   87 - 94   2019.05 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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In a previous study, we reported that Curcuma longa strain Ryudai gold (RD) showed antifungal activity against Fusarium solani sensu lato (FSSL) among the different species and varieties of turmeric. The present study focused on isolation, identification and structural elucidation of antifungal compounds in RD. The ethyl acetate (EtOAc) fraction was eluted with n-hexane and EtOAc with gradually increasing the concentration of EtOAc (n-hexane:EtOAc 100:0 80:20 60:40, 40:60, 20:80 and 0:100). The antifungal compounds were isolated from the most effective fraction by using silica gel, TOYOPEARL® HW-40F column, and high-performance liquid chromatography. Structural identification of the antifungal compounds was conducted using 1H NMR, 13C NMR, and liquid chromatography-tandem mass spectrometry. The MeOH extract of the rhizome of RD inhibited the growth of FSSL in a concentration-dependent manner. The EtOAc fraction of the MeOH extract of RD demonstrated the highest antifungal activity against FSSL. The purified antifungal compounds were turmeronol B (1), turmeronol A (2), (E)-α-atlantone (3), dihydrobisdemethoxycurcumin (4), demethoxycurcumin (5) and curcumin (6). These six compounds showed concentration-dependent antifungal activity against FSSL. The concentration required for 50% growth inhibition (IC50) of the four isolates of FSSL ranged from 116 to172, 127 to 185, 88 to 109, 90 to 112, 74 to 80 and 63 to 68 μM/L for turmeronol B, turmeronol A, (E)-α-atlantone, dihydrobisdemethoxycurcumin, demethoxycurcumin and curcumin, respectively. These results suggested that RD contained potential antifungal compounds that could be useful to control FSSL. The isolated compounds of RD can be a good source of natural antifungal agents or the lead compounds for the development of new synthetic drugs.

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Isolation and structural elucidation of antifungal compounds from Curcuma amada

Akter J

Asian Pacific Journal of Tropical Medicine ( Asian Pacific Journal of Tropical Medicine )  12 ( 3 ) 123 - 129   2019.03

Type of publication: Research paper (scientific journal)

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Study of the Interrelation between Variations in Sugarcane Juice Contents and Qualities of Non-Centrifugal Brown Sugar "Kokuto" during Production

HIROSE Naoto, MAEDA Goki, TAKARA Kensaku, WADA Koji

Food preservation science ( Japan Association of Food Preservation Scientists )  45 ( 3 ) 141 - 147   2019.03 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

Antioxidant activity of different species and varieties of turmeric (Curcuma spp): Isolation of active compounds.

Akter J, Hossain MA, Takara K, Islam MZ, Hou DX

Comparative biochemistry and physiology. Toxicology & pharmacology : CBP ( Comparative Biochemistry and Physiology Part - C: Toxicology and Pharmacology )  215   9 - 17   2019.01 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Study of the Interrelation between Variations in Sugarcane Juice Contents and Qualities of Non-Centrifugal Brown Sugar "<i>Kokuto</i>" during Production

HIROSE Naoto, MAEDA Goki, TAKARA Kensaku, WADA Koji

Food Preservation Science ( Japan Association of Food Preservation Scientists )  45 ( 3 ) 141 - 147   2019 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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<p> The interrelation between variations in sugarcane juice contents and the qualities of non-centrifugal brown sugar, "<i>Kokuto</i>", was investigated during the production period of <i>Kokuto</i> in 2014 and 2015. Large variations were observed in sugarcane juice contents, including the reducing sugar ratio, amino acid, organic acid, and sodium contents. Many components of sugarcane juice and <i>Kokuto</i> were positively correlated. Therefore, the component of sugarcane juice, sugarcane, was shown to be reflected in the contents of <i>Kokuto</i>. The apparent sugar purity of sugarcane juice was correlated with the hardness, moisture, and water activity of <i>Kokuto</i>. As a result, it was suggested that management of the apparent sugar purity during the production process is important for stabilizing the quality of <i>Kokuto</i>. Taste sensor measurement values showed a large fluctuation in the saltiness of <i>Kokuto</i>. "Salty taste" was positively correlated with the acetic acid, sodium, and calcium contents, but negatively correlated with the amino acid content of sugarcane juice.</p>

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Plant growth inhibitors in turmeric (Curcuma longa) and their effects on Bidens pilosa

Akter J. Islam MD Z, Takara K, Hossain MD A, Gima S, Hou DX

Weed Biology and Management ( Weed Biology and Management )  18 ( 3 ) 136 - 145   2018.09 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Antifungal Activity of Various Species and Strains of Turmeric (Curcuma SPP.) Against Fusarium Solani Sensu Lato

Akter J, Hossain MA, Sano A, Takara K, Islam MZ, Hou DX

Pharmaceutical Chemistry Journal ( Pharmaceutical Chemistry Journal )  52 ( 4 ) 320 - 325   2018.07 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Influence of Fruit Ripening on Color, Organic Acid Contents, Capsaicinoids, Aroma Compounds, and Antioxidant Capacity of Shimatogarashi (Capsicum frutescens).

Manikharda, Takahashi M, Arakaki M, Yonamine K, Hashimoto F, Takara K, Wada K

Journal of Oleo science ( 公益社団法人 日本油化学会 )  67 ( 1 ) 113 - 123   2018.01 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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<p>Shimatogarashi (<i>Capsicum frutescens</i>) is a typical chili pepper domesticated in southern Japan. Important traits of Shimatogarashi peppers, such as color; proportion of organic acids, capsaicinoids, and aromatic compounds; and antioxidant activity in three stages of maturity (green (immature), orange (turning), and red (mature) stages) were characterized. The results indicated that the concentration of organic acids, including ascorbic, citric, and malic acid, increased during ripening. In addition, the amount of capsaicinoids, which are responsible for the pungent taste of chili peppers, increased as the fruit matured to the orange and red stages. The volatile compound profile of Shimatogarashi was dominated by the presence of esters, which mainly contributed to fruity notes. The total amount of volatile compounds analyzed by gas chromatography-headspace solid-phase microextraction (GC-HS-SPME), especially esters, decreased as the fruit changed in color from green to red. This was in contrast to the amount of terpenoids, especially limonene, which increased at the red stage, denoting a change in flavor from fruity to a more citrus-like aroma. Based on the total phenolic content (TPC), the oxygen radical absorbance capacity (ORAC) and the diphenylpicrylhydrazyl (DPPH) free radical method, the antioxidant capacity of Shimatogarashi showed an increase at the mature red stage. However, while the red stage showed higher pungency and antioxidant capacity as well as an attractive color, the results of aromatic compound analysis revealed that the immature green stage had the advantages of having pleasant fruity smell, making it suitable for use in condiments.</p>

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Isolation and characterization of allelopathic compounds from the indigenous rice variety ‘boterswar’ and their biological activity against Echinochloa crus-galli L

S. M. Masum, M. A. Hossain, H. Akamine, J. I. Sakagami, T. Ishii, S. Gima, T. Kensaku, P. C. Bhowmik

Allelopathy Journal   43 ( 1 ) 31   2018.01 [ Peer Review Accepted ]

Type of publication: Research paper (scientific journal)

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Aqueous methanol extracts of the Bangladesh indigenous rice (Oryza sativa L.ssp. indica) variety „Boterswar‟ inhibited the germination and seedling growth of Lepidium sativum L. and Echinochloa crus-galli L. Beauv which suggested that this variety may contain phytotoxic substance(s). Four biologically active compounds, syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde), (-) loliolide, 3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one and 3-hydroxy-β-ionone, were isolated from the ethyl acetate phase using several chromatographic steps. The chemical structures of the compounds were determined through electrospray ionization and spectroscopic analyses. The biological activity of these compounds showed that concentration > 10 μM significantly inhibited the root and shoot growth of E. crus-galli seedlings, and the I50 (50% growth inhibition) values ranged from 16.03 to 27.23 μM and 23.94 to 75.49 μM for root and shoot growth, respectively. The four compounds synergistically suppressed the growth of E. crus-galli more strongly than the individual compounds. Thus, the indigenous rice „Boterswar‟ has potential use for weed management and this indigenous variety could be used to develop a new commercial rice variety that may suppress weeds.

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