PMID- 35323466
OWN - NLM
STAT- MEDLINE
DCOM- 20220401
LR  - 20220401
IS  - 1660-3397 (Electronic)
IS  - 1660-3397 (Linking)
VI  - 20
IP  - 3
DP  - 2022 Feb 25
TI  - First Identification of 12beta-Deoxygonyautoxin 5 (12alpha-Gonyautoxinol 5) in the 
      Cyanobacterium Dolichospermum circinale (TA04) and 12beta-Deoxysaxitoxin 
      (12alpha-Saxitoxinol) in D. circinale (TA04) and the Dinoflagellate Alexandrium 
      pacificum (Group IV) (120518KureAC).
LID - 10.3390/md20030166 [doi]
LID - 166
AB  - Saxitoxin and its analogues, paralytic shellfish toxins (PSTs), are potent and 
      specific voltage-gated sodium channel blockers. These toxins are produced by some 
      species of freshwater cyanobacteria and marine dinoflagellates. We previously 
      identified several biosynthetic intermediates of PSTs, as well as new analogues, 
      from such organisms and proposed the biosynthetic and metabolic pathways of PSTs. 
      In this study, 12beta-deoxygonyautoxin 5 (12alpha-gonyautoxinol 5 = gonyautoxin 
      5-12(R)-ol) was identified in the freshwater cyanobacterium, Dolichospermum 
      circinale (TA04), and 12beta-deoxysaxitoxin (12alpha-saxitoxinol = saxitoxin-12(R)-ol) 
      was identified in the same cyanobacterium and in the marine dinoflagellate 
      Alexandrium pacificum (Group IV) (120518KureAC) for the first time from natural 
      sources. The authentic standards of these compounds and 12alpha-deoxygonyautoxin 5 
      (12beta-gonyautoxinol 5 = gonyautoxin 5-12(S)-ol) were prepared by chemical 
      derivatization from the major PSTs, C1/C2, produced in D. circinale (TA04). These 
      standards were used to identify the deoxy analogues by comparing the retention 
      times and MS/MS spectra using high-resolution LC-MS/MS. Biosynthetic or metabolic 
      pathways for these analogues have also been proposed based on their structures. 
      The identification of these compounds supports the alpha-oriented stereoselective 
      oxidation at C12 in the biosynthetic pathway towards PSTs.
FAU - Akamatsu, Michiru
AU  - Akamatsu M
AD  - Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, 
      Japan.
FAU - Hirozumi, Ryosuke
AU  - Hirozumi R
AD  - Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, 
      Japan.
FAU - Cho, Yuko
AU  - Cho Y
AD  - Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, 
      Japan.
FAU - Kudo, Yuta
AU  - Kudo Y
AUID- ORCID: 0000-0002-1586-2004
AD  - Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, 
      Japan.
AD  - Frontier Research Institute for Interdisciplinary Sciences, Tohoku University, 
      Sendai 980-8578, Japan.
FAU - Konoki, Keiichi
AU  - Konoki K
AUID- ORCID: 0000-0001-5788-5426
AD  - Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, 
      Japan.
FAU - Oshima, Yasukatsu
AU  - Oshima Y
AD  - Graduate School of Life Sciences, Tohoku University, Sendai 980-8577, Japan.
FAU - Yotsu-Yamashita, Mari
AU  - Yotsu-Yamashita M
AUID- ORCID: 0000-0002-5009-0409
AD  - Graduate School of Agricultural Science, Tohoku University, Sendai 980-8572, 
      Japan.
LA  - eng
GR  - JP19H04636, JP17H06406, JP20H02921, JP19K22266,JP 19K06232/Japan Society for the 
      Promotion of Science/
GR  - 2020/Uehara Memorial Foundation/
PT  - Journal Article
DEP - 20220225
PL  - Switzerland
TA  - Mar Drugs
JT  - Marine drugs
JID - 101213729
RN  - 35523-89-8 (Saxitoxin)
RN  - 3833H3TURF (gonyautoxin V)
RN  - 75420-34-7 (saxitoxinol)
RN  - Dolichospermum circinale
SB  - IM
MH  - Cyanobacteria/*chemistry/metabolism
MH  - Dinoflagellida/*chemistry/metabolism
MH  - Molecular Structure
MH  - Saxitoxin/*analogs & derivatives/chemistry/isolation & purification/metabolism
PMC - PMC8954441
OTO - NOTNLM
OT  - 12beta-deoxygonyautoxin 5 (12alpha-gonyautoxinol 5)
OT  - 12beta-deoxysaxitoxin (12alpha-saxitoxinol)
OT  - Alexandrium pacificum
OT  - Dolichospermum circinale
OT  - paralytic shellfish toxins
OT  - saxitoxin
COIS- The authors declare no conflict of interest.
EDAT- 2022/03/25 06:00
MHDA- 2022/04/02 06:00
PMCR- 2022/02/25
CRDT- 2022/03/24 12:14
PHST- 2021/12/31 00:00 [received]
PHST- 2022/02/20 00:00 [revised]
PHST- 2022/02/22 00:00 [accepted]
PHST- 2022/03/24 12:14 [entrez]
PHST- 2022/03/25 06:00 [pubmed]
PHST- 2022/04/02 06:00 [medline]
PHST- 2022/02/25 00:00 [pmc-release]
AID - md20030166 [pii]
AID - marinedrugs-20-00166 [pii]
AID - 10.3390/md20030166 [doi]
PST - epublish
SO  - Mar Drugs. 2022 Feb 25;20(3):166. doi: 10.3390/md20030166.