Gambierone, a Ladder-Shaped Polyether from the Dinoflagellate <i>Gambierdiscus belizeanus</i>

Rodríguez, Inés; Genta‐Jouve, Grégory; Alfonso, Carmen; Calabro, Kevin; Albrecht, Eva; Sánchez, Jon Andoni; Alfonso, Amparo; Thomas, Olivier P.; Botana, Luís M.

doi:10.1021/acs.orglett.5b00902

Cited by 68 publications

(89 citation statements)

References 21 publications

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“…14 This approach based on theoretical NMR calculations has been proven to be a very powerful tool in natural products structure elucidation. 9,15 Taking both 1 H and 13 C chemical shifts calculations for the DP4 probability analysis ( Figure S40), the relative configuration at C-9a was defined to be R.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial Oligophenalenone Dimers from the Soil Fungus Talaromyces stipitatus

et al. 2016

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New polyketide-derived oligophenalenone dimers, 9a-epi-bacillisporin E (1) and bacillisporins F−H (2−5), along with the known bacillisporin A (6), were isolated from the fungus Talaromyces stipitatus. Their structures and absolute configurations were determined on the basis of spectroscopic analyses, electronic circular dichroism, and GIAO NMR shift calculation followed by DP4 analysis. The antimicrobial activity of these compounds was evaluated against a panel of human pathogenic bacteria. Among them, bacillisporin H (5) exhibited antimicrobial activity together with modest cytotoxicity against HeLa cells.

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Section: Resultsmentioning

confidence: 99%

Antimicrobial Oligophenalenone Dimers from the Soil Fungus Talaromyces stipitatus

et al. 2016

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“…For that reason, the authors carried out NMR calculations of the eight resulting candidates at the B3LYP/6‐31G(d)//B3LYP/STO‐3G level. The DP4 probability computed from 13 C data strongly supported the 2 R *,4 R *,38 S * stereochemistry present in 28 (91.2 %) that was finally proposed for this complex natural product …”

Section: Dp4mentioning

confidence: 99%

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Grimblat

Sarotti

2016

Chemistry A European J

189

147

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The calculations of NMR properties of molecules using quantum chemical methods have deeply impacted several branches of organic chemistry. They are particularly important in structural or stereochemical assignments of organic compounds, with implications in total synthesis, stereoselective reactions, and natural products chemistry. In studying the evolution of the strategies developed to support (or reject) a structural proposal, it becomes clear that the most effective and accurate ones involve sophisticated procedures to correlate experimental and computational data. Owing to their relatively high mathematical complexity, such calculations (CP3, DP4, ANN-PRA) are often carried out using additional computational resources provided by the authors (such as applets or Excel files). This Minireview will cover the state-of-the-art of these toolboxes in the assignment of organic molecules, including mathematical definitions, updates, and discussion of relevant examples.

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“…Gambierdiscus species also synthesize other toxins, including gambieric acids [81], gambierol [82], gambierone [83] and maitotoxins [84,85]. Maitotoxin (MTX-1) itself is a water-soluble cyclic polyether ladder marine toxin that was first described in the mid-1970s (Table 1).…”

Section: Ciguatoxins and Maitotoxinsmentioning

confidence: 99%

Recent Trends in Marine Phycotoxins from Australian Coastal Waters

2017

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Phycotoxins, which are produced by harmful microalgae and bioaccumulate in the marine food web, are of growing concern for Australia. These harmful algae pose a threat to ecosystem and human health, as well as constraining the progress of aquaculture, one of the fastest growing food sectors in the world. With better monitoring, advanced analytical skills and an increase in microalgal expertise, many phycotoxins have been identified in Australian coastal waters in recent years. The most concerning of these toxins are ciguatoxin, paralytic shellfish toxins, okadaic acid and domoic acid, with palytoxin and karlotoxin increasing in significance. The potential for tetrodotoxin, maitotoxin and palytoxin to contaminate seafood is also of concern, warranting future investigation. The largest and most significant toxic bloom in Tasmania in 2012 resulted in an estimated total economic loss of ~AUD$23M, indicating that there is an imperative to improve toxin and organism detection methods, clarify the toxin profiles of species of phytoplankton and carry out both intra- and inter-species toxicity comparisons. Future work also includes the application of rapid, real-time molecular assays for the detection of harmful species and toxin genes. This information, in conjunction with a better understanding of the life histories and ecology of harmful bloom species, may lead to more appropriate management of environmental, health and economic resources.

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Gambierone, a Ladder-Shaped Polyether from the Dinoflagellate Gambierdiscus belizeanus

Cited by 68 publications

References 21 publications

Antimicrobial Oligophenalenone Dimers from the Soil Fungus Talaromyces stipitatus

Antimicrobial Oligophenalenone Dimers from the Soil Fungus Talaromyces stipitatus

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Recent Trends in Marine Phycotoxins from Australian Coastal Waters

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