Evaluation of the significance of prenylation on the physiological function of flavonoids

• Project/Area Number: 25292075
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Food science
• Research Institution: The University of Tokushima
• Principal Investigator: TERAO Junji 徳島大学, 大学院医歯薬学研究部, 教授 (60093275)
• Co-Investigator(Kenkyū-buntansha): MUKAI Rie 徳島大学, 大学院医歯薬学研究部, 助教 (90547978) ; 中村 俊之 静岡県立大学, 食品栄養科学部, 助教 (90706988)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥14,040,000 (Direct Cost: ¥10,800,000、Indirect Cost: ¥3,240,000); Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000); Fiscal Year 2014: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000); Fiscal Year 2013: ¥7,930,000 (Direct Cost: ¥6,100,000、Indirect Cost: ¥1,830,000)
• Keywords: 食品機能 / フラボノイド / プレニル化 / 抗酸化酵素 / 血管内皮 / 血管内皮細胞 / ヘムオキシゲナーゼー１ / カベオリン-1 / カベオラ / Nrf2 / MAPK経路 / 生体利用性 / 抱合体代謝

Outline of Final Research Achievements

This study was aimed to evaluate the effect of prenylation on the functionality of flavonoids from the viewpoint of structure-activity relationship. The compounds used were 6-prenylquercetin (6-PQ), 5-PQ and 8-PQ. We found that hydrophobicity is changed depending on the positon of prenyl group in the flavonoid structure. 6-PQ with the highest hydrophobicity showed the highest induction of heme oxygenase-1 in accordance with the highest efficiency of cellular uptake in human blood endothelial cells. The result that quercetin modulated the vascular function of caveolin-1 in the cells may indicate that caveolin-1 and caveolae are potential targets for the action of prenylated flavonoids

Research Products

• [Journal Article] Preventive effect of dietary quercetin on disuse muscle atrophy by targeting mitochondria in denervated mice. (2016)
  • Author(s): Mukai, R., Matsui N., Fujikura Y., Matsumoto N., Hou D-X, Kanzaki N., Shibata H., Horikawa M., Iwasa K., Hirasaka K., Nikawa T., Terao J.
  • Journal Title: Jouranl of Nutritional Biochemistry Volume: 31 Pages: 67-76
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Effect of quercetin and its metabolite on caveolin-1 exspression induced by oxidized LDL and lysophosphatidylcholine in endothelial cells (2016)
  • Author(s): Kamada C, Mukai R., Kondo A., Sato S, Terao J
  • Journal Title: Journal of Clinical Biochemistry and Nutrition Volume: 印刷中
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] プレニルフラボノイドの生体利用性 (2015)
  • Author(s): 向井理恵、寺尾純二
  • Journal Title: 化学と生物 Volume: 53 Pages: 71-73
• [Journal Article] Prenylation modulates the bioavailability and bioaccumulation of dietary flavonoids (2014)
  • Author(s): J. Terao, R. Mukai
  • Journal Title: Archives of Biochemistry and Biophysics Volume: 印刷中 Pages: 12-16
  • DOI: 10.1016/j.abb.2014.04.002
  • Peer Reviewed
• [Journal Article] Role of dietary flavonoids in oxidative stress and prevention of muscle atrophy (2013)
  • Author(s): R.Mukai, J. Terao
  • Journal Title: The Journal of Physical Fitness and Sports Medicine Volume: 2 Issue: 4 Pages: 385-392
  • DOI: 10.7600/jpfsm.2.385
  • NAID: 10031203875
  • ISSN: 2186-8123, 2186-8131
  • Peer Reviewed
• [Presentation] Caveolin-1発現に対するケルセチンおよびα-とこふぇロールの効果 (2016)
  • Author(s): 鎌田智英実、近藤あかり、向井理恵、寺尾純二
  • Organizer: ビタミンE研究会
  • Place of Presentation: 高松市市民会館(香川県高松市）
  • Year and Date: 2016-01-09
• [Presentation] A siginal transduction pathway in prenylquercetin-induced heme oxygenase-1 ezpression in vascular endothelium cells (2015)
  • Author(s): Shono H, Saito H, Sato S, Kawamura T, Nemoto H, Terao J Mukai R
  • Organizer: The 6th International Conferenceon Food Factors
  • Place of Presentation: Seoul, Korea
  • Year and Date: 2015-11-24
  • Int'l Joint Research
• [Presentation] Effect of quercerin on hydrogen peroxide-induced phosphorylation of caveolin-1 endothelial cells. (2015)
  • Author(s): Kondo A, Kamada C, Mukai R, Terao J.
  • Organizer: The 6th International Conferenceon Food Factors
  • Place of Presentation: Seoul, KOREA
  • Year and Date: 2015-11-24
  • Int'l Joint Research
• [Presentation] 血管内皮細胞における酸化ストレス誘導のcaveolin-1リン酸化に対するケルセチンおよびその代謝物の効果 (2015)
  • Author(s): 近藤あかり、鎌田智英実、向井理恵、寺尾純二
  • Organizer: 日本農芸化学会2015年度中四国・西日本支部合同大会
  • Place of Presentation: 愛媛大学(愛媛県松山市）
  • Year and Date: 2015-09-17
• [Presentation] ポリフェノールの生体利用性と高機能化戦略 (2014)
  • Author(s): 寺尾純二
  • Organizer: 日本農芸化学会中四国支部
  • Place of Presentation: 徳島大学工学部(徳島県徳島市）
  • Year and Date: 2014-09-26
  • Invited
• [Presentation] 筋萎縮予防因子としての食事性ポリフェノール (2014)
  • Author(s): 寺尾純二、向井理恵、根本尚夫、二川健
  • Organizer: 日本栄養食糧学会大会
  • Place of Presentation: 酪農学園大学(北海道江別市）
  • Year and Date: 2014-05-30 – 2014-06-01
  • Invited
• [Presentation] プレニル基がケルセチンのグルクロン酸抱合とABCトランスポーターによる排出に及ぼす影響
  • Author(s): 嶺川祥子、向井理恵、藤倉温、生城真一、榊利之、室田佳恵子、河村知志、根本尚夫、寺尾純二
  • Organizer: 第67回日本栄養・食糧学会大会
  • Place of Presentation: 名古屋大学(愛知県）
• [Presentation] Prenylation modulates the bioavailavility of dietary flavonoids
  • Author(s): J. Terao
  • Organizer: VI International Conference on Polyphenols and Health
  • Place of Presentation: 国立ブレノスアイレス大学（Buenos Aires, Argentina)
  • Invited
• [Book] Clinincal Aspects of Functional Foods and Nutritional foods and Nutraceuticals (2015)
  • Author(s): Junji Terao, Rie Mukai, Yuki Yamashita, Arisa Ochi, Shohei Kohno、Katsuya Hirasaka, Takeshi Nikawa
  • Total Pages: 452
  • Publisher: CRC Press