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Establishment of the basic technology for producing Z-isomer-rich carotenoid material having high bioavailability and excellent processability

Research Project

Project/Area Number 19K15779
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 38050:Food sciences-related
Research InstitutionMeijo University

Principal Investigator

Honda Masaki  名城大学, 理工学部, 助教 (60824191)

Project Period (FY) 2019-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2020: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2019: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsカロテノイド / 異性化 / 抽出 / 安定化 / 天然触媒 / イソチオシアネート類 / ポリスルフィド類 / シス-トランス異性化 / 有機分子触媒 / 抗酸化剤 / 超臨界流体
Outline of Research at the Start

カロテノイド類は食品や化粧品などに使用される天然色素素材として極めて重要な化合物であり、一般に植物や微生物から溶媒抽出により得られる。その利用価値は極めて高いにもかかわらず、カロテノイド(トランス型)の溶媒への溶解度が低いため、天然から効率よく入手できないことが問題となっている。本研究は、カロテノイドを効率的にシス異性化させる新規化学変換技術を開発し、物性改変による溶解度特性の改善によって、天然資源からカロテノイド素材を効率的に製造する基盤技術を確立する。

Outline of Final Research Achievements

Carotenoids are important natural compounds used in food and cosmetic industries, and are generally obtained from plants and microorganisms by solvent extraction. However, natural carotenoids (all-E-isomer) have low solubility in various solvents, and that results in low production efficiency of them via the extraction method. Here, we developed a novel Z-isomerization technology of carotenoids using natural catalysts, and utilizing the changes in physical properties associated with the isomerization, an efficient method for carotenoid extraction was developed. In addition, a stabilization technology of Z-isomer-rich carotenoids was also developed aiming at practical applications.

Academic Significance and Societal Importance of the Research Achievements

これまで、天然のカロテノイド(トランス型)をシス型に変換するためには、高温処理や重金属触媒の利用が不可欠であった。今回、イソチオシアネート類やポリスルフィド類など、天然由来の有機分子がカロテノイド異性化反応の触媒効果を示すことを明らかにした。本知見を活用することで、シス型比率を高めたカロテノイド素材の効率的な製造が可能になる。さらに、異性化に伴う物性改変を活用することでカロテノイド素材の生産効率を改善できることを明らかにし、シス型カロテノイドを安定化できる処方を開発した。これらの成果は、カロテノイド素材の高付加価値化と低価格化につながる重要な知見である。

Report

(3 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • Research Products

    (41 results)

All 2021 2020 2019

All Journal Article (20 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 18 results,  Open Access: 6 results) Presentation (13 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results) Book (3 results) Patent(Industrial Property Rights) (5 results)

  • [Journal Article] Evaluation and improvement of storage stability of astaxanthin isomers in oils and fats2021

    • Author(s)
      Honda Masaki、Kageyama Hakuto、Hibino Takashi、Osawa Yukiko、Kawashima Yuki、Hirasawa Kazuaki、Kuroda Ikuo
    • Journal Title

      Food Chemistry

      Volume: 352 Pages: 129371-129371

    • DOI

      10.1016/j.foodchem.2021.129371

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enriched (Z)-lycopene in tomato extract via co-extraction of tomatoes and foodstuffs containing Z-isomerization-accelerating compounds2021

    • Author(s)
      Honda Masaki、Murakami Kazuya、Ichihashi Kohei、Takada Wataru、Goto Motonobu
    • Journal Title

      Catalysts

      Volume: 11 Issue: 4 Pages: 462-462

    • DOI

      10.3390/catal11040462

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enhanced Efficiency of Carotenoid Processing Utilizing Change in Physicochemical Properties Induced by <i>Z</i>-isomerization2020

    • Author(s)
      本田 真己
    • Journal Title

      Japan Journal of Food Engineering

      Volume: 21 Issue: 1 Pages: 1-10

    • DOI

      10.11301/jsfe.20565

    • NAID

      130007818492

    • ISSN
      1345-7942, 1884-5924
    • Year and Date
      2020-03-15
    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synergistic Effects of Food Ingredients and Vegetable Oils on Thermal Isomerization of Lycopene2020

    • Author(s)
      Honda Masaki、Kageyama Hakuto、Hibino Takashi、Ichihashi Kohei、Takada Wataru、Goto Motonobu
    • Journal Title

      Journal of Oleo Science

      Volume: 69 Issue: 12 Pages: 1529-1540

    • DOI

      10.5650/jos.ess20174

    • NAID

      130007948414

    • ISSN
      1345-8957, 1347-3352
    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Production of (Z)-lycopene-rich tomato concentrate: A natural catalyst-utilized and oil-based study for practical applications2020

    • Author(s)
      Honda Masaki、Ichihashi Kohei、Takada Wataru、Goto Motonobu
    • Journal Title

      Journal of Agricultural and Food Chemistry

      Volume: 68 Issue: 40 Pages: 11273-11281

    • DOI

      10.1021/acs.jafc.0c04892

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of liposomes encapsulating β-carotene using supercritical carbon dioxide with ultrasonication2020

    • Author(s)
      Tanaka Yukako、Uemori Chiho、Kon Tatsuhiko、Honda Masaki、Wahyudiono、Machmudah Siti、Kanda Hideki、Goto Motonobu
    • Journal Title

      The Journal of Supercritical Fluids

      Volume: 161 Pages: 104848-104848

    • DOI

      10.1016/j.supflu.2020.104848

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-step preparation of Z-isomer-rich β-carotene nanosuspensions utilizing a natural catalyst, allyl isothiocyanate, via supercritical CO22020

    • Author(s)
      Zhang Yelin、Honda Masaki、Fukaya Tetsuya、Wahyudiono、Kanda Hideki、Goto Motonobu
    • Journal Title

      Symmetry

      Volume: 12 Issue: 5 Pages: 777-777

    • DOI

      10.3390/sym12050777

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Possibility of using astaxanthin-rich dried cell powder from Paracoccus carotinifaciens to improve egg yolk pigmentation of laying hens2020

    • Author(s)
      Honda Masaki、Kawashima Yuki、Hirasawa Kazuaki、Uemura Takeshi、Jinkun Sun、Hayashi Yoshiaki
    • Journal Title

      Symmetry

      Volume: 12 Issue: 6 Pages: 923-923

    • DOI

      10.3390/sym12060923

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Thermal‐and photo‐induced isomerization of all‐E‐and Z‐isomer‐rich xanthophylls: astaxanthin and its structurally related xanthophylls, adonirubin and adonixanthin2020

    • Author(s)
      Masaki Honda, Toshiyasu Sowa, Yuki Kawashima
    • Journal Title

      European Journal of Lipid Science and Technology

      Volume: 122 Issue: 5 Pages: 1900462-1900462

    • DOI

      10.1002/ejlt.201900462

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] 超臨界流体の食品・飲料への応用2020

    • Author(s)
      後藤 元信, 本田 真己, 根路銘 葉月, 田中 雅裕, 福里 隆一
    • Journal Title

      日本食品工学会誌

      Volume: 21 Pages: 7-10

    • Related Report
      2019 Research-status Report
  • [Journal Article] Chemical‐free approach for Z‐isomerization of lycopene in tomato powder: Hot air and superheated steam heating above the melting point of lycopene2020

    • Author(s)
      Masaki Honda, Hakuto Kageyama, Takashi Hibino, Rungaroon Waditee‐Sirisattha, Tetsuya Fukaya, Yoshiaki Hayashi, Motonobu Goto
    • Journal Title

      European Journal of Lipid Science and Technology

      Volume: 122 Issue: 3 Pages: 1900327-1900327

    • DOI

      10.1002/ejlt.201900327

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] 本田 真己, 後藤 元信2020

    • Author(s)
      カロテノイドのシス異性化技術の開発とその応用
    • Journal Title

      アグリバイオ

      Volume: 4 Pages: 50-53

    • Related Report
      2019 Research-status Report
  • [Journal Article] Isomerization of commercially important carotenoids (lycopene, β-carotene, and astaxanthin) by natural catalysts: Isothiocyanates and polysulfides2020

    • Author(s)
      Masaki Honda, Hakuto Kageyama, Takashi Hibino, Kohei Ichihashi, Wataru Takada, Motonobu Goto
    • Journal Title

      Journal of Agricultural and Food Chemistry

      Volume: 68 Issue: 10 Pages: 3228-3237

    • DOI

      10.1021/acs.jafc.0c00316

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Efficient and environmentally friendly method for carotenoid extraction from Paracoccus carotinifaciens utilizing naturally occurring Z-isomerization-accelerating catalysts2020

    • Author(s)
      Masaki Honda, Hakuto Kageyama, Takashi Hibino, Toshiyasu Sowa, Yuki Kawashima
    • Journal Title

      Process Biochemistry

      Volume: 89 Pages: 146-154

    • DOI

      10.1016/j.procbio.2019.10.005

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Z-Isomers of lycopene exhibit greater liver accumulation than the all-E-isomer in mice.2020

    • Author(s)
      Honda, M., Nakayama, Y., Nishikawa, S., Tsuda, T.
    • Journal Title

      Biosci. Biotechnol. Biochem.

      Volume: 84 Issue: 2 Pages: 428-431

    • DOI

      10.1080/09168451.2019.1677144

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enhanced <i>cis</i>-Isomerization of (all-<i>trans</i>)-Lycopene in Tomato Products with via Specific Vegetables in Home Cooking2019

    • Author(s)
      竹村 諒太, 本田 真己, 深谷 哲也
    • Journal Title

      Journal of Cookery Science of Japan

      Volume: 52 Issue: 2 Pages: 57-66

    • DOI

      10.11402/cookeryscience.52.57

    • NAID

      130007638533

    • ISSN
      1341-1535, 2186-5787
    • Year and Date
      2019-04-05
    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Impact of global traditional seasonings on thermal Z-isomerization of (all-E)-lycopene in tomato puree2019

    • Author(s)
      Masaki Honda, Hakuto Kageyama, Takashi Hibino, Yelin Zhang, Kohei Ichihashi, Tetsuya Fukaya, Motonobu Goto
    • Journal Title

      LWT

      Volume: 116 Pages: 108565-108565

    • DOI

      10.1016/j.lwt.2019.108565

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Alterations in lycopene concentration and Z‐isomer content in egg yolk of hens fed all‐E‐isomer‐rich and Z‐isomer‐rich lycopene2019

    • Author(s)
      Masaki Honda, Hiroto Ishikawa, Yoshiaki Hayashi
    • Journal Title

      Animal Science Journal

      Volume: 90 Issue: 9 Pages: 1261-1269

    • DOI

      10.1111/asj.13276

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Improved carotenoid processing with sustainable solvents utilizing Z-isomerization-induced alteration in physicochemical properties: A review and future directions2019

    • Author(s)
      Masaki Honda, Hakuto Kageyama, Takashi Hibino, Yelin Zhang, Wahyudiono, Hideki Kanda, Ryusei Yamaguchi, Ryota Takemura, Tetsuya Fukaya, Motonobu Goto
    • Journal Title

      Molecules

      Volume: 24 Issue: 11 Pages: 2149-2149

    • DOI

      10.3390/molecules24112149

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enhanced Z-isomerization of tomato lycopene through the optimal combination of food ingredients2019

    • Author(s)
      Masaki Honda, Hakuto Kageyama, Takashi Hibino, Ryota Takemura, Motonobu Goto, Tetsuya Fukaya
    • Journal Title

      Scientific Reports

      Volume: 9 Issue: 1 Pages: 7979-7979

    • DOI

      10.1038/s41598-019-44177-4

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 融解処理によるカロテノイドの異性化と加工への応用2020

    • Author(s)
      本田 真己
    • Organizer
      日本油化学会 第59回年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 天然由来の有機分子触媒を用いたカロテノイドの高効率シス異性化2020

    • Author(s)
      本田 真己
    • Organizer
      日本食品工学会 第21回年次大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] トマトリコピンの最新知見 ~健康効果と効率的な摂取方法~2019

    • Author(s)
      本田 真己
    • Organizer
      2019年度 名城大学農学部附属農場公開講演会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Enhanced production of β-carotene suspensions using supercritical CO2 via naturally occurring Z-isomerization-accelerating catalyst2019

    • Author(s)
      Yelin Zhang, Masaki Honda, Wahyudiono, Hideki Kanda, Motonobu Goto
    • Organizer
      The 26th Regional Symposium on Chemical Engineering
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 採卵鶏への異なるリコピン含量の飼料給与が卵黄中リコピンと卵質に及ぼす影響2019

    • Author(s)
      林 義明, 石川 大登, 本田 真己
    • Organizer
      第126回 日本家禽学会
    • Related Report
      2019 Research-status Report
  • [Presentation] Effects of Z-isomerization in supercritical fluid processing of carotenoids2019

    • Author(s)
      Motonobu Goto, Masaki Honda, Tomohiko Kodama, Haruka Sato, Wahyudiono, Hideki Kanda
    • Organizer
      Effects of Z-isomerization in supercritical fluid processing of carotenoids
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 本田 真己, 石川大登, 林義明2019

    • Author(s)
      高い色揚げ効果を有する畜産飼料の開発と評価
    • Organizer
      第33回 カロテノイド研究談話会
    • Related Report
      2019 Research-status Report
  • [Presentation] Enhanced production of β-carotene suspensions using supercritical CO2 via naturally occurring Z-isomerization-accelerating catalyst2019

    • Author(s)
      Yelin Zhang, Masaki Honda, Wahyudiono, Hideki Kanda, Motonobu Goto
    • Organizer
      26th Regional Symposium on Chemical Engineering
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 植物由来グリーン触媒を用いた パラコッカス菌アスタキサンチンの抽出効率改善2019

    • Author(s)
      本田 真己, 岨 稔康, 川嶋 祐貴
    • Organizer
      第15回 アスタキサンチン研究会
    • Related Report
      2019 Research-status Report
  • [Presentation] カロテノイドのシス異性化に関する研究2019

    • Author(s)
      本田 真己
    • Organizer
      日本食品工学会 第20回年次大会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 化学薬品フリーなカロテノイドのシス異性化手法の開発2019

    • Author(s)
      本田 真己
    • Organizer
      日本食品工学会 第20回年次大会
    • Related Report
      2019 Research-status Report
  • [Presentation] シス-トランス異性化反応により創出するカロテノイド加工のイノベーション2019

    • Author(s)
      本田 真己
    • Organizer
      第25回 国際食品素材/添加物展・会議 (ifia JAPAN)
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Ultrasonic-assisted preparation of liposome using supercritical carbon dioxide2019

    • Author(s)
      Motonobu Goto, Yukako Tanaka, Wahyudiono, Hideki Kanda, Masaki Honda
    • Organizer
      17th European Meeting on Supercritical Fluids
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Book] Studies in Natural Products Chemistry: Chapter 5 - Carotenoid isomers: A systematic review of the analysis, biological activity, physicochemical property, and methods for isomerization2021

    • Author(s)
      Masaki Honda
    • Publisher
      Elsevier
    • Related Report
      2020 Annual Research Report
  • [Book] Pigments from Microalgae Handbook: Chapter 18 - Nutraceutical and pharmaceutical applications of carotenoids:2020

    • Author(s)
      Masaki Honda
    • Publisher
      Springer Nature
    • Related Report
      2020 Annual Research Report
  • [Book] An Essential Guide to Astaxanthin: Dietary Sources, Properties and Health Benefits2019

    • Author(s)
      Masaki Honda
    • Total Pages
      113
    • Publisher
      Nova Science Publishers
    • ISBN
      9781536155716
    • Related Report
      2019 Research-status Report
  • [Patent(Industrial Property Rights)] 機能性食品用組成物及び機能性食品2020

    • Inventor(s)
      本田 真己
    • Industrial Property Rights Holder
      本田 真己
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] シス型キサントフィル組成物および使用方法2020

    • Inventor(s)
      本田真己 他
    • Industrial Property Rights Holder
      JXTGエネルギー株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2020-030453
    • Filing Date
      2020
    • Related Report
      2019 Research-status Report
  • [Patent(Industrial Property Rights)] トマトパウダー、トマトパウダーの製造方法、及びトマトパウダー抽出物の製造方法2019

    • Inventor(s)
      本田真己
    • Industrial Property Rights Holder
      学校法人名城大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-190278
    • Filing Date
      2019
    • Related Report
      2019 Research-status Report
  • [Patent(Industrial Property Rights)] シス型キサントフィルの抽出方法2019

    • Inventor(s)
      本田真己 他
    • Industrial Property Rights Holder
      JXTGエネルギー株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-163742
    • Filing Date
      2019
    • Related Report
      2019 Research-status Report
  • [Patent(Industrial Property Rights)] リコピンの異性化方法、シス異性体リコピン含有組成物及びその製造方法2019

    • Inventor(s)
      本田真己 他
    • Industrial Property Rights Holder
      カゴメ株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-152588
    • Filing Date
      2019
    • Related Report
      2019 Research-status Report

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Published: 2019-04-18   Modified: 2022-01-27  

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