Elucidation of biosynthetic pathways towards tetrodotoxin and saxitoxin based on the structures of novel biosynthetic intermediates
| Project/Area Number |
26292057
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Bioorganic chemistry
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| Research Institution | Tohoku University |
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Principal Investigator |
Yamashita Mari 東北大学, (連合)農学研究科(研究院), 教授 (50192430)
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| Co-Investigator(Renkei-kenkyūsha) |
NISHIKAWA TOSHIO 名古屋大学, 大学院生命農学研究科, 教授 (90208158)
NAGASAWA KAZUO 東京農工大学, 大学院工学研究院, 教授 (10247223)
KONOKI KEIICHI 東北大学, 大学院農学研究科, 准教授 (40292825)
CHO YUKO 東北大学, 大学院農学研究科, 助教 (60323086)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥16,510,000 (Direct Cost: ¥12,700,000、Indirect Cost: ¥3,810,000)
Fiscal Year 2016: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2015: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥6,110,000 (Direct Cost: ¥4,700,000、Indirect Cost: ¥1,410,000)
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| Keywords | テトロドトキシン / サキシトキシン / 生合成 / LC/MS / 中間体 / グアニジン / 構造決定 / LC-MS |
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| Outline of Final Research Achievements |
We reported the first C10-C5 directly bonded tetrodotoxin (TTX) analogues from newts, and proposed monoterpene origin of TTX. In this study, five novel bicyclic guanidine compounds related to TTX were isolated and their structures were determined. These structures strongly supported monoterpene origin of TTX.
Although biosynthetic genes corresponding to production of STX had been reported, chemical study of intermediates were not enough. In this study, Int-A', Int-C'2, and CyclicC' were chemically synthesized, and identified in toxin producing cyanobacterium and dinoflagellate using high resolution LC-MS/MS. In addition, incorporation experiments with 15N labeled these intermediates indicated that Int-A' and Int-C'2 are genuine precursors of STX analogues and Cyclic C' is a shunt compound. This is the first shunt pathway in STX biosynthesis ever found.
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Report
(4 results)
Research Products
(100 results)
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[Journal Article] Inhibition of veratridine-induced delayed inactivation of the voltage-sensitive sodium channel by synthetic analogs of crambescin B2017
Author(s)
Tadaaki Tsukamoto, Yukie Chiba, Atsuo Nakazaki, Yuki Ishikawa, Yoshiki Nakane, Yuko Cho, Mari Yotsu-Yamashita, Toshio Nishikawa, Minoru Wakamori, and Keiichi Konoki,*
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Journal Title
Bioorg. Medicinal Chem. Letter.
Volume: 27
Pages: 1247-1251
DOI
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Peer Reviewed / Open Access / Acknowledgement Compliant
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[Journal Article] Identification of okadaic acid binding protein 2 in reconstituted sponge cell clusters from Halichondria okadai and its contribution to the detoxification of okadaic acid.2015
Author(s)
Keiichi Konoki*, Kayo Okada, Mami Kohama, Hiroki Matsuura, Kaori Saito, Yuko Cho, Goh Nishitani, Tomofumi Miyamoto, Seketsu Fukuzawa, Kazuo Tachibana, Mari Yotsu-Yamashita
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Journal Title
Toxicon
Volume: 108
Pages: 38-45
DOI
Related Report
Peer Reviewed
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[Journal Article] Confirmation of the absence of tetrodotoxin and its analogues in the juveniles of the Japanese fire-bellied newt, Cynops pyrrhogaster, captive-reared from eggs in the laboratory using HILIC-LC-MS2015
Author(s)
Kudo, Y., Chiba, C., Konoki, K., Cho, Y. and Yotsu-Yamashita, M.
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Journal Title
Toxicon
Volume: 101
Pages: 101-105
DOI
Related Report
Peer Reviewed / Acknowledgement Compliant
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[Journal Article] A High-Throughput Screen for Inhibitors of the Prolyl Isomerase, Pin1, Identifies a Seaweed Polyphenol that Reduces Adipose Cell Differentiation.2014
Author(s)
Mori T, Hidaka M, Ikuji H, Yoshizawa I, Toyohara H, Okuda T, Uchida C, Asano T, Yotsu-Yamashita M, Uchida T
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Journal Title
Biosci Biotechnol Biochem
Volume: 78
Pages: 832-838
DOI
Related Report
Peer Reviewed / Open Access / Acknowledgement Compliant
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[Presentation] Analysis of polycavernoside A in the red alga Gracilaria edulis that caused previous fatal food poisonings in Guam and Philippines2014
Author(s)
○Mari Yotsu-Yamashita1, Kosuke Maeta1, Yuki Taya1, Eri Omizu1, Takahide Endo1, Yuko Cho1, Keiichi Konoki1, Mirriam A. Cayme2, Yasuo Fukuyo3, Sherwood Hall4, Takeshi Yasumoto5,
Organizer
The 16th International conference on Harmful Algae
Place of Presentation
Wellington, New Zealand
Year and Date
2014-10-27 – 2014-10-31
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