TY - JOUR
T1 - Identification of tricyclic guanidino compounds from the tetrodotoxin-bearing newt taricha granulosa
AU - Kudo, Yuta
AU - Hanifin, Charles T.
AU - Yotsu-Yamashita, Mari
N1 - Funding Information:
Taricha granulosa were collected by C.T.H. in Lincoln County, OR under collecting permit no. 020-19. We appreciate Mr. D. Unabara, Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, for acquiring NMR spectra using the Bruker AVANCE III 600 apparatus, especially LR-HSQMBC. This work was funded by the Japan Society for the Promotion of Science (JSPS) through its KAKENHI Grant-in-Aid for Scientific Research nos. JP20H02921, JP19H04636, JP17H06406, and JP19K22266 to M.Y.-Y. and nos. JP18H05997, JP19K21141, and JP20K15405 to Y.K. This work was supported by The Uehara Memorial Foundation (to M.Y.-Y.) and The Naito Foundation (to Y.K.).
Funding Information:
Taricha granulosa were collected by C.T.H. in Lincoln County, OR under collecting permit no. 020-19. We appreciate Mr. D. Unabara, Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, for acquiring NMR spectra using the Bruker AVANCE III 600 apparatus, especially LRHSQMBC. This work was funded by the Japan Society for the Promotion of Science (JSPS) through its KAKENHI Grant-in- Aid for Scientific Research nos. JP20H02921, JP19H04636, JP17H06406, and JP19K22266 to M.Y.-Y. and nos. JP18H05997, JP19K21141, and JP20K15405 to Y.K. This work was supported by The Uehara Memorial Foundation (to M.Y.-Y.) and The Naito Foundation (to Y.K.).
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/5/7
Y1 - 2021/5/7
N2 - The biosynthesis of the potent neurotoxin tetrodotoxin (TTX, 1) is still unresolved. We used MS-guided screening and nuclear magnetic resonance analyses including long-range HSQMBC to characterize two novel skeletal tricyclic guanidino compounds, Tgr-288 (2a and 2b) and Tgr-210 (3), from the TTX-bearing newt, Taricha granulosa. The presence of these compounds in toxic newts is congruent with a previously proposed pathway for TTX biosynthesis in terrestrial organisms that includes a monoterpene precursor and the production of structurally diversified guanidino compounds.
AB - The biosynthesis of the potent neurotoxin tetrodotoxin (TTX, 1) is still unresolved. We used MS-guided screening and nuclear magnetic resonance analyses including long-range HSQMBC to characterize two novel skeletal tricyclic guanidino compounds, Tgr-288 (2a and 2b) and Tgr-210 (3), from the TTX-bearing newt, Taricha granulosa. The presence of these compounds in toxic newts is congruent with a previously proposed pathway for TTX biosynthesis in terrestrial organisms that includes a monoterpene precursor and the production of structurally diversified guanidino compounds.
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U2 - 10.1021/acs.orglett.1c00916
DO - 10.1021/acs.orglett.1c00916
M3 - Article
C2 - 33830775
AN - SCOPUS:85104926705
SN - 1523-7060
VL - 23
SP - 3513
EP - 3517
JO - Organic Letters
JF - Organic Letters
IS - 9
ER -