Estimation of saponin chemical structures in soyfoods by profile anbalysis

• Project/Area Number: 18H02149
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Review Section: Basic Section 38050:Food sciences-related
• Research Institution: Iwate University
• Principal Investigator: TSUKAMOTO CHIGEN 岩手大学, 農学部, 教授 (20312514)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Project Status: Completed (Fiscal Year 2020)
• Budget Amount: ¥15,990,000 (Direct Cost: ¥12,300,000、Indirect Cost: ¥3,690,000); Fiscal Year 2020: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000); Fiscal Year 2019: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2018: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
• Keywords: 大豆 / サポニン / 化学構造解析 / プロファイル解析 / 遺伝子 / LC-PDA/MS/MS / 大豆加工食品 / 化学構造 / 生合成 / 大豆サポニン / サポニン糖鎖配列

Outline of Final Research Achievements

It had been said that the chemical structures of soybean saponins could not be elucidated without purification step and instrumental analysis such as HI-MS, IR, NMR. However, it takes a lot of time with hard work in order to obtain sufficient amount for instrumental analysis. It turned out that we could elucidate the chemical structures of soybean saponins without doing the purification and instrumental analysis by using the profile analysis technique (general judgment by genetic information and the LC-PDA/MS/MS analysis) by this study.

Academic Significance and Societal Importance of the Research Achievements

天然有機化合物の化学構造は，その物質を単離精製して機器分析（HR-MS、IR、NMR分析等）しないと決定できないと言われてきた。しかし，食品や生体内で検出される多様な天然有機化合物の化学構造は単離精製が非常に困難な場合が多く，化学構造決定に至るまでに多大な労力と時間を要してきた。
本研究は，蓄積されている膨大な遺伝子DNA情報と，極微量の試料で必要な情報が得られるLC-PDA/MS/MS分析とを活用することで，天然有機化合物の化学構造決定が可能になることを示唆している。

Research Products

• [Int'l Joint Research] 韓国全南大学生命工学部/韓国慶北大学応用生物学部(韓国)
• [Int'l Joint Research] 韓国全南大学生命工学部/韓国慶北大学応用生物学部(韓国)
• [Int'l Joint Research] 中国農業科学院作物科学研究所(中国)
• [Int'l Joint Research] 韓国全南大学生命工学部/韓国慶北大学応用生物科学部(韓国)
• [Int'l Joint Research] カセットサート大学食品開発研究所(タイ)
• [Journal Article] Soyasaponin composition complexities in soyfoods relating nutraceutical properties and undesirable taste characteristics (2021)
  • Author(s): Chitisankul Wanida T.、Itabashi Mei、Son Haereon、Takahashi Yuya、Ito Ayaka、Varanyanond Warunee、Tsukamoto Chigen
  • Journal Title: LWT-Food Science and Technology Volume: 146 Pages: 111337-111337
  • DOI: 10.1016/j.lwt.2021.111337
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] ダイズサポニンの生合成と機能 (2020)
  • Author(s): 石本政男、塚本知玄
  • Journal Title: アグリバイオ Volume: 4(12) Pages: 23-27
• [Journal Article] Reconstruction of the Evolutionary Histories of UGT Gene Superfamily in Legumes Clarifies the Functional Divergence of Duplicates in Specialized Metabolism (2020)
  • Author(s): Krishnamurthy Panneerselvam、Tsukamoto Chigen、Ishimoto Masao
  • Journal Title: International Journal of Molecular Sciences Volume: 21 Issue: 5 Pages: 1855-1855
  • DOI: 10.3390/ijms21051855
  • Peer Reviewed / Open Access
• [Journal Article] Molecular Analysis of Two Novel Missense Mutations in the Sg-1 Gene Associated with Group A Saponin Biosynthesis in Soybean (2019)
  • Author(s): Sundaramoorthy Jagadeesh、Park Gyu Tae、Son Hae Reon、Tsukamoto Chigen、Lee Jeong-Dong、Seo Hak Soo、Song Jong Tae
  • Journal Title: Crop Science Volume: 59 Issue: 6 Pages: 2634-2641
  • DOI: 10.2135/cropsci2019.06.0376
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Characterization of a new sg-5 variant with reduced biosynthesis of group A saponins in soybean [Glycine max (L.) Merr.]. (2019)
  • Author(s): Jagadeesh Sundaramoorthy, Sampathkumar Palanisamy, Gyu Tae Park, Hae Reon Son, Chigen Tsukamoto, Jeong-Dong Lee, Jeong Hoe Kim, Hak Soo Seo, Jong Tae Song
  • Journal Title: Molecular Breeding Volume: 39 Issue: 10-11 Pages: 144-144
  • DOI: 10.1007/s11032-019-1066-4
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] High-Throughput Screening and Characterization of a High-Density Soybean Mutant Library Elucidate the Biosynthesis Pathway of Triterpenoid Saponins (2019)
  • Author(s): Krishnamurthy Panneerselvam、Fujisawa Yukiko、Takahashi Yuya、Abe Hanako、Yamane Kentaro、Mukaiyama Kyosuke、Son Hae-Reon、Hiraga Susumu、Kaga Akito、Anai Toyoaki、Tsukamoto Chigen、Ishimoto Masao
  • Journal Title: Plant and Cell Physiology Volume: 0 Issue: 5 Pages: 1-16
  • DOI: 10.1093/pcp/pcz025
  • Peer Reviewed / Open Access
• [Journal Article] Biosynthesis of DDMP saponins in soybean is regulated by a distinct UDP ‐glycosyltransferase (2018)
  • Author(s): Sundaramoorthy Jagadeesh、Park Gyu Tae、Komagamine Kumpei、Tsukamoto Chigen、Chang Jeong Ho、Lee Jeong‐Dong、Kim Jeong Hoe、Seo Hak Soo、Song Jong Tae
  • Journal Title: New Phytologist Volume: 222 Issue: 1 Pages: 261-274
  • DOI: 10.1111/nph.15588
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Phenotypic and genotypic signature of saponin chemical composition in Chinese wild soybean (Glycine soja): revealing genetic diversity, geographical variation and dispersal history of the species (2018)
  • Author(s): Takahashi Yuya、Li Xiang-Hua、Tsukamoto Chigen、Wang Ke-Jing
  • Journal Title: Crop and Pasture Science Volume: 69 Issue: 11 Pages: 1126-1126
  • DOI: 10.1071/cp18214
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Genetic and functional characterization of Sg-4 glycosyltransferase involved in the formation of sugar chain structure at the C-3 position of soybean saponins (2018)
  • Author(s): Takagi Kyoko、Yano Ryoichi、Tochigi Saeko、Fujisawa Yukiko、Tsuchinaga Hiroki、Takahashi Yuya、Takada Yoshitake、Kaga Akito、Anai Toyoaki、Tsukamoto Chigen、Seki Hikaru、Muranaka Toshiya、Ishimoto Masao
  • Journal Title: Phytochemistry Volume: 156 Pages: 96-105
  • DOI: 10.1016/j.phytochem.2018.09.002
  • Peer Reviewed / Open Access
• [Journal Article] Characterization of an EMS-induced soybean mutant with an increased content of Af saponin and a new component Ab-δ in the seed hypocotyl (2018)
  • Author(s): Park Cheol Woo、Kulkarni Krishnanand P.、Kim Minsu、Mukaiyama Kyosuke、Tsukamoto Chigen、Chung Gyuhwa、Song Jong Tae、Lee Jeong-Dong
  • Journal Title: Euphytica Volume: 214 Issue: 9 Pages: 163-163
  • DOI: 10.1007/s10681-018-2242-z
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Allelic differentiation at the Sg-1 locus for the terminal sugar of the C-22 position of group A saponin in Chinese wild soybean (Glycine soja Sieb. & Zucc.) (2018)
  • Author(s): Takahashi Yuya、Li Xianghua、Tsukamoto Chigen、Wang Kejing
  • Journal Title: Molecular Breeding Volume: 38 Issue: 7 Pages: 93-93
  • DOI: 10.1007/s11032-018-0851-9
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Isoflavone profile diversity in Korean wild soybeans (Glycine soja Sieb. & Zucc.). (2018)
  • Author(s): Chigen TSUKAMOTO, Muhammad Amjad NAWAZ, Ayaka KUROSAKA, Bao LE, Jeong Dong LEE, Eunho SON, Seung Hwan YANG, Cemel Kurt, Faheem Shehzad BALOCH, Gyuhwa CHUNG
  • Journal Title: Turkish Journal of Agriculture and Forestry Volume: 42 Issue: 4 Pages: 248-261
  • DOI: 10.3906/tar-1801-95
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Isolation and Characterization of the Soybean Sg-3 Gene that is Involved in Genetic Variation in Sugar Chain Composition at the C-3 Position in Soyasaponins (2018)
  • Author(s): Yano Ryoichi、Takagi Kyoko、Tochigi Saeko、Fujisawa Yukiko、Nomura Yuhta、Tsuchinaga Hiroki、Takahashi Yuya、Takada Yoshitake、Kaga Akito、Anai Toyoaki、Tsukamoto Chigen、Seki Hikaru、Muranaka Toshiya、Ishimoto Masao
  • Journal Title: Plant and Cell Physiology Volume: 59 Issue: 4 Pages: 792-805
  • DOI: 10.1093/pcp/pcy019
  • Peer Reviewed / Open Access
• [Presentation] Structural elucidation of soybean saponins by LC-PDA/MS/MS profile analysis (2021)
  • Author(s): Haereon Son, Genta Takahashi, Takehiro Mori, Minae Sasaki, Hiroki Muraoka, Susumu Hiraga, Masao Ishimoto and Chigen Tsukamoto
  • Organizer: 日本育種学会第139回講演会
• [Presentation] Reconstruction of the evolutionary histories of UGT gene superfamily clarifies the species-specific functional divergence of duplicates in specialized metabolism. (2019)
  • Author(s): Panneerselvam Krishnamurthy, Ryoichi Yano, Saeko Tochigi, Kyoko Takagi, Yukiko Fujisawa, Chigen Tsukamoto and Masao Ishimoto
  • Organizer: TERPNET 2019 -14th International Meeting on the Biosynthesis, Function and Synthetic Biology of Isoprenoids
  • Int'l Joint Research
• [Presentation] Relation between chemical structure and mass spectrum pattern of soyasaponins (2019)
  • Author(s): Hae Reon Son, Kyosuke Mukaiyama and Chigen Tsukamoto
  • Organizer: 2nd Food Chemistry Conference, P2.2.40. 17-19 September, Seville, Spain
  • Int'l Joint Research
• [Presentation] Attempts for developing new soybeans which accumulate only group B saponins to enhance human health benefits (2019)
  • Author(s): Chigen Tsukamoto, Hae Reon Son, Kumpei Komagamine, Kyosuke Mukaiyama, Jeong-Dong Lee and Jong Tae Song
  • Organizer: 2nd Food Chemistry Conference, P.2.2.44. 17-19 September, Seville, Spain
  • Int'l Joint Research
• [Presentation] 共発現解析に基づくダイズサポニン配糖化酵素の同定 (2019)
  • Author(s): Panneerselvam Krishnamurthy，藤澤由紀子，Soo-Yeon Chung，Hae-Reon Son，下田宜司，平賀 勧，加賀秋人，穴井豊昭，塚本知玄，關 光，村中俊哉，石本政男
  • Organizer: 日本育種学会第136回講演会（9月6-7日，発表6日401，近畿大学）
• [Presentation] Profile Analysis: New method to elucidate chemical structures of saponin in soybean (2019)
  • Author(s): Haereon Son, Yuya Takahashi, Hiroki Muraoka, Yukiko Fujisawa, Susumu Hiraga, Masao Ishimoto, Chigen Tsukamoto
  • Organizer: The International Conference on Research in Science, Engineering and Technology
  • Int'l Joint Research
• [Presentation] マメ科モデル植物ミヤコグサのサポニン組成解析 (2018)
  • Author(s): 山根健太郎，Son Haereon，藤澤由紀子，平賀 勧，石本政男，塚本知玄
  • Organizer: 第39回種子生理生化学研究会
• [Presentation] LC-MSによるダイズサポニンプロファイル解析用データベースの構築 (2018)
  • Author(s): 向山恭介，Son Haereon，藤澤由紀子，平賀 勧，石本政男，塚本知玄
  • Organizer: 第39回種子生理生化学研究会
• [Presentation] Relationship between saponin chemical structures and the interaction of two gene combination on sg5/sg-9 allele (2018)
  • Author(s): Kumpei Komagamine，Kyosuke Mukaiyama，Haereon Son，Jong Tae Song，Jeong-Dong Lee，Chigen Tsukamoto
  • Organizer: 第39回種子生理生化学研究会