2003
DOI: 10.1021/jf030101r
|View full text |Cite
|
Sign up to set email alerts
|

Gymnodimine C, an Isomer of Gymnodimine B, from Karenia selliformis

Abstract: Gymnodimine C (1), an oxidized analogue of the spiro-imine algal toxin gymnodimine (3), was isolated from extracts of the cells of Karenia selliformis. The structure of gymnodimine C, determined by one- and two-dimensional 1H NMR spectroscopy and mass spectrometry, was found to be isomeric with gymnodimine B (2) at C-18.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

1
93
0

Year Published

2006
2006
2020
2020

Publication Types

Select...
5
3
1

Relationship

1
8

Authors

Journals

citations
Cited by 103 publications
(94 citation statements)
references
References 4 publications
1
93
0
Order By: Relevance
“…Accurate masses (Table 3) of 1 and the minor gymnodimine were consistent with the molecular formula for gymnodimine B/C, C 32 H 45 O 5 N (with 11 rings or double bond equivalents), previously isolated from K. selliformis (Miles et al, 2000(Miles et al, , 2003. However, the mass spectrometric fragmentation patterns differed from those expected for gymnodimine B/C based on reports from literature (Ben Naila et al, 2012).…”
Section: Resultssupporting
confidence: 80%
See 1 more Smart Citation
“…Accurate masses (Table 3) of 1 and the minor gymnodimine were consistent with the molecular formula for gymnodimine B/C, C 32 H 45 O 5 N (with 11 rings or double bond equivalents), previously isolated from K. selliformis (Miles et al, 2000(Miles et al, , 2003. However, the mass spectrometric fragmentation patterns differed from those expected for gymnodimine B/C based on reports from literature (Ben Naila et al, 2012).…”
Section: Resultssupporting
confidence: 80%
“…Gymnodimine A (2) was found first in New Zealand oysters in 1994 (Seki et al, 1995;Stewart et al, 1997), and since then, it has been detected in several other locations around the world, and supposedly produced by K. selliformis. The hydroxylated analogues, gymnodimine B (3) and C (4), have also been isolated from K. selliformis (Miles et al, 2000(Miles et al, , 2003. These gymnodimines can be present in filter-feeding shellfish throughout the year, and have been detected in large quantities in coastal waters of New Zealand (Stirling, 2001) and Tunisia (Bire et al, 2002;Ben Naila et al, 2012) after prolonged blooms of K. selliformis.…”
Section: Introductionmentioning
confidence: 99%
“…New gymnodimine isomers, gymnodimine B and C, were isolated from Karenia selliformis (Fig. 4) (Miles et al, 2000(Miles et al, ,2003. The absolute configuration of gambieric acid from Gambierdiscus toxicus was determined by a combination of Mosher analysis, NMR, and chiral HPLC (Morohashi et al, 2000).…”
Section: F Othermentioning
confidence: 99%
“…1) have been identified from contaminated shellfish or from extracts of the dinoflagellate Karenia selliformis (12)(13)(14)(15). Similar to spirolides, gymnodimines contain a spirocyclic imine but, in contrast to spirolides, they bear a trisubstituted tetrahydrofuran embedded within a 16-membered macrocycle.…”
mentioning
confidence: 99%