Synthetic study on a bioactive natural product, the most active hatching agent of potato cyst nematodes
| Project/Area Number |
18K05456
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Multi-year Fund |
|---|
| Section | 一般 |
|---|
| Review Section |
Basic Section 38040:Bioorganic chemistry-related
|
|---|
| Research Institution | Tohoku University (2019-2020)
Nagoya University (2018) |
|---|
Principal Investigator |
|
|---|
| Project Period (FY) |
2018-04-01 – 2021-03-31
|
| Project Status |
Completed (Fiscal Year 2020)
|
| Budget Amount *help |
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
|
|---|
| Keywords | 有機化学 / 合成化学 / 天然物化学 / 生理活性 |
|---|
| Outline of Final Research Achievements |
Synthesis of solanoeclepin A, the most active hatching agent of potato cyst nematode isolated from hydroponic potato cultures was examined for the chemical supply of solanoeclepin A. As a result, a tricyclic compound possessing a DEF ring of the right-hand nucleus of solanoeclepin A was synthesized from Hajos-Parrish ketone through introduction of a hydroxy group at the C-15 position and construction of the highly strained cyclobutane by samarium(II)-mediated 4-exo-trig radical cyclization.
|
| Academic Significance and Societal Importance of the Research Achievements |
申請者は、化学合成によって得られる天然物や中間体等を利用すれば生命現象を分子レベルで詳細に解明できると考え、天然から得ることが困難でその生理活性の詳細が明らかにされていない天然有機化合物を研究材料に取り上げ、その合成研究を行っている。本研究で着目した高度に歪んだシクロブタンを持つソラノエクレピンAは、天然からの単離収率が極めて低く、生合成経路も未だ不明なことから、有機合成による量的供給が必要不可欠である。また、合成難度が極めて高いため、構造活性相関の情報に基づきシスト線虫の孵化促進活性を保持した単純化アナログを開発することが重要であると考えた。
|
Report
(4 results)
Research Products
(21 results)
-
[Journal Article] The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes.2021
Author(s)
Uenoyama, R.; Miyazaki, T.; Hurst, J.; Beynon, R.; Asachi, M.; Murooka, T.; Onoda, I.; Miyazawa, Y.; Katayama, T.; Yamashita, T.; Kaneko, S.; Nishikawa, T.; Miyazaki, M.
-
Journal Title
Sci. Adv.
Volume: 7
Issue: 4
Pages: 1-14
DOI
NAID
Related Report
Peer Reviewed / Open Access / Int'l Joint Research
-
-
[Journal Article] Biosynthesis of Indole Diterpene Lolitrems: Radical-Induced Cyclization of an Epoxyalcohol Affording a Characteristic Lolitremane Skeleton2020
Author(s)
Yulu Jiang, Taro Ozaki, Mei Harada, Tadachika Miyasaka, Hajime Sato, Kazunori Miyamoto, Junichiro Kanazawa, Chengwei Liu, Jun-ichi Maruyama, Masaatsu Adachi, Atsuo Nakazaki, Toshio Nishikawa, Masanobu Uchiyama, Atsushi Minami, Hideaki Oikawa
-
Journal Title
Angew. Chem. Int. Ed.
Volume: 59
Issue: 41
Pages: 17996-18002
DOI
NAID
Related Report
Peer Reviewed
-
-
-
-
-
-
-
-
-
-
-
-
[Presentation] Sensitivity of the voltage-gated sodium channel subtypes, Nav1.1 to Nav1.7, against guanidine-containing natural products and their analogues2019
Author(s)
Tadaaki Tsukamoto, Yukie Chiba, Shunsuke Tsunogae, Tomoshi Yamada, Yuko Cho, Ryo Sakakibara, Takuya Imazu, Shouta Tokoro, Yoshiki Satake, Yuki Ishikawa, Yoshiki Nakane, Masaatsu Adachi, Atsuo Nakazaki, Toshio Nishikawa, Minoru Wakamori, Mari Yotsu-Yamashita, Keiichi Konoki
Organizer
The 1st International Symposium on Chemical Communication (ISCC2019)
Related Report
-
-
-
-
-
-
