PMID- 33813339
OWN - NLM
STAT- MEDLINE
DCOM- 20210615
LR  - 20210615
IS  - 1879-1298 (Electronic)
IS  - 0045-6535 (Linking)
VI  - 278
DP  - 2021 Sep
TI  - Two new skeletal analogues of saxitoxin found in the scallop, Patinopecten 
      yessoensis, as possible metabolites of paralytic shellfish toxins.
PG  - 130224
LID - S0045-6535(21)00693-7 [pii]
LID - 10.1016/j.chemosphere.2021.130224 [doi]
AB  - The scallop, Patinopecten yessoensis, was screened for new saxitoxin analogues to 
      study the metabolism of paralytic shellfish toxins (PSTs), and this resulted in 
      the discovery of two new analogues: M5-hemiaminal (HA) and M6-HA. M5-HA was 
      isolated and its structure was determined by using NMR spectroscopy. It contains 
      hydrogen at C-4 with opposite stereochemistry to that in saxitoxin, and a 
      hemiaminal was formed between 9-NH(2) and the hydrated ketone at C-12 in 
      alpha-orientation. This is the first reported structural feature in a natural 
      saxitoxin analogue, whereas the same ring system has previously been reported in 
      a synthetic saxitoxin analogue, FD-saxitoxin. Acid hydrolysis of the carbamoyl 
      N-sulfate in M5-HA produced M6-HA which was also identified in P. yessoensis by 
      using LC-MSMS. M5-HA was not synthetically produced from M1 (11-hydroxy 
      gonyautoxin-5) and M3 (11,11-dihydroxy gonyautoxin-5) through incubation in 
      aqueous buffers. Furthermore, PSTs in the hepatopancreas of P. yessoensis, 
      cultured in a bay located in northeastern Japan, were chronologically analyzed in 
      2018. The highest concentrations of M1/M3/M5-HA were observed two weeks after 
      C-toxins had reached their highest concentrations, which provides evidence that 
      M1/M3/M5-HA are metabolites of C-toxins. The voltage-gated sodium channel 
      blockage activity of M6-HA was not detected at the concentration of 140 nM by 
      using the Neuro-2A veratridine/ouabain assay.
CI  - Copyright (c) 2021 Elsevier Ltd. All rights reserved.
FAU - Numano, Satoshi
AU  - Numano S
AD  - Graduate School of Agricultural Science, Tohoku University, 468-1 
      Aramaki-Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8572, Japan; Iwate Prefectural 
      Research Institute for Environmental Sciences and Public Health, 1-11-16 
      Kita-Iioka, Morioka, Iwate, 020-0857, Japan.
FAU - Kudo, Yuta
AU  - Kudo Y
AD  - Graduate School of Agricultural Science, Tohoku University, 468-1 
      Aramaki-Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8572, Japan; Frontier Research 
      Institute for Interdisciplinary Sciences, Tohoku University, 6-3 
      Aramaki-Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8578, Japan.
FAU - Cho, Yuko
AU  - Cho Y
AD  - Graduate School of Agricultural Science, Tohoku University, 468-1 
      Aramaki-Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8572, Japan.
FAU - Konoki, Keiichi
AU  - Konoki K
AD  - Graduate School of Agricultural Science, Tohoku University, 468-1 
      Aramaki-Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8572, Japan.
FAU - Kaga, Yoshimasa
AU  - Kaga Y
AD  - Iwate Prefectural Inland Fisheries Technology Center, Yoriki, Matsuo, Iwate, 
      028-7302, Japan.
FAU - Nagasawa, Kazuo
AU  - Nagasawa K
AD  - Department of Biotechnology and Life Science, Faculty of Technology, Tokyo 
      University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo, 
      184-8588, Japan.
FAU - Yotsu-Yamashita, Mari
AU  - Yotsu-Yamashita M
AD  - Graduate School of Agricultural Science, Tohoku University, 468-1 
      Aramaki-Aza-Aoba, Aoba-ku, Sendai, Miyagi, 980-8572, Japan. Electronic address: 
      mari.yamashita.c1@tohoku.ac.jp.
LA  - eng
PT  - Journal Article
DEP - 20210315
PL  - England
TA  - Chemosphere
JT  - Chemosphere
JID - 0320657
RN  - 35523-89-8 (Saxitoxin)
SB  - IM
MH  - Animals
MH  - Japan
MH  - *Pectinidae
MH  - *Saxitoxin/toxicity
MH  - Seafood
MH  - Shellfish/analysis
OTO - NOTNLM
OT  - Metabolites
OT  - NMR
OT  - Paralytic shellfish toxins
OT  - Saxitoxin
OT  - Scallop
EDAT- 2021/04/05 06:00
MHDA- 2021/06/16 06:00
CRDT- 2021/04/04 20:56
PHST- 2020/12/16 00:00 [received]
PHST- 2021/03/09 00:00 [revised]
PHST- 2021/03/10 00:00 [accepted]
PHST- 2021/04/05 06:00 [pubmed]
PHST- 2021/06/16 06:00 [medline]
PHST- 2021/04/04 20:56 [entrez]
AID - S0045-6535(21)00693-7 [pii]
AID - 10.1016/j.chemosphere.2021.130224 [doi]
PST - ppublish
SO  - Chemosphere. 2021 Sep;278:130224. doi: 10.1016/j.chemosphere.2021.130224. Epub 
      2021 Mar 15.