Synthetic study on furofuran lignans by means of control of electronic properties of phenol
| Project/Area Number |
26860013
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | University of Shizuoka |
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Principal Investigator |
Inai Makoto 静岡県立大学, 薬学部, 助教 (20621626)
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| Project Period (FY) |
2014-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | セサミン / セサミノール / ヘジオトール A / 不斉アルドール反応 / フロフランリグナン / 有機触媒 / プリンセピン / プロリンアルドール / C-H挿入反応 / キノンメチド |
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| Outline of Final Research Achievements |
Furofuran lignans isolated from various vascular plants have been reported to exhibit antitumor, antioxidant, antiviral, and antihypertensive activities, as well as inhibition of low-density lipoprotein oxidation. These furofuran lignans and their derivatives are expected to be useful as lead compounds for drug development.
In this research, plant products (+)-hedyotol A, (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through proline-catalyzed cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.
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Report
(3 results)
Research Products
(21 results)
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[Journal Article] The source of "fairy rings": 2-azahypoxanthine and its metabolite found in a novel purine metabolic pathway in plants2014
Author(s)
J-H. Choi, T. Ohnishi, Y. Yamakawa, S. Takeda, S. Sekiguchi, W. Maruyama, K. Yamashita, T. Suzuki, A. Morita, T. Ikka, R. Motohashi, Y. Kiriiwa, H. Tobina, T. Asai, S. Tokuyama, H. Hirai, N. Yasuda, K. Noguchi, T. Asakawa, S. Sugiyama, T. Kan, H. Kawagishi
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Journal Title
Angew. Chem. Int. Ed.
Volume: 53
Issue: 6
Pages: 1552-1555
DOI
NAID
Related Report
Peer Reviewed
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[Journal Article] Total Syntheses of (+)-Sesamin and (+)-Sesaminol2014
Author(s)
Ryo Ishikawa, Naoto Yoshida, Yusuke Akao, Yusuke Kawabe, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, and Toshiyuki Kan
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Journal Title
Chemistry Letters
Volume: 43
Issue: 10
Pages: 1572-1574
DOI
NAID
ISSN
0366-7022, 1348-0715
Related Report
Peer Reviewed / Open Access
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[Journal Article] Isolation and Total Syntheses of Cytotoxic Cryptolactones A1, A2, B1, and B2: α,β-Unsaturated δ-Lactones from a Cryptomyzus sp. Aphid.2014
Author(s)
M. Horikawa, M. Inai, Y. Oguri, E. Kuroda, M. Tanaka, S. Suzuki, T. Ito, S. Takahashi, H. Kaku, and T. Tsunoda
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Journal Title
J. Nat. Prod.
Volume: 77
Issue: 11
Pages: 2459-2464
DOI
Related Report
Peer Reviewed / Open Access / Acknowledgement Compliant
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[Presentation] Synthetic Study on Furofuran Lignans2014
Author(s)
Ryo Ishikawa, Yusuke Kawabe, Yusuke Akao, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
Organizer
The 2nd International Conference on Pharma-Food
Place of Presentation
Shizuoka
Year and Date
2014-11-06
Related Report
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[Presentation] Synthetic Study on Furofuran Lignans2014
Author(s)
Ryo Ishikawa, Yusuke Kawabe, Yusuke Akao, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan:
Organizer
The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
Place of Presentation
Nagoya
Year and Date
2014-09-05
Related Report
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