Complete 13C-labeling pattern of yessotoxin a marine ladder-frame polyether

Yamazaki, Masatoshi; Tachibana, Kunihide; Satake, Masayuki

doi:10.1016/j.tet.2010.12.015

Cited by 15 publications

(17 citation statements)

References 22 publications

(10 reference statements)

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“…369 Biosynthetic experiments on the dinoagellate Protoceratium reticulatum utilising 13 C-labelled precursors suggested that the carbons in the ladder-frame polyether yessotoxin (YTX) 370,371 were derived from acetates, a methyl of methionine and glycolate, and that the six-membered ring tetrads (rings A-D and H-K) were constructed from repeated condensation of C3 units, formed from a methyl group of a deleted acetate and an intact acetate unit. 372…”

Section: Biosynthesismentioning

confidence: 99%

Marine natural products

et al. 2013

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This review covers the literature published in 2011 for marine natural products, with 870 citations (558 for the period January to December 2011) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1152 for 2011), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Biosynthesismentioning

confidence: 99%

Marine natural products

et al. 2013

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“…The specific mechanism for this increase would be likely dependent on the class of toxins. For lipophilic toxins such as karlotoxins and yessotoxins, this could result from increased glycolate levels (the starter unit for toxin synthesis; Yamazaki et al 2011), allowing more fixed carbon to be diverted to the toxin machinery. A major cellular source of glycolate is photorespiration (Spencer & Togasaki 1981); however, it might be expected that this source would be reduced when ambient CO 2 :O 2 ratios are high, and so this does not appear to be consistent with the observed trends in lipophilic toxin synthesis under acidified conditions.…”

Section: Future Directionsmentioning

confidence: 99%

Global change and the future of harmful algal blooms in the ocean

Fu¹,

Tatters²,

Hutchins³

2012

Mar. Ecol. Prog. Ser.

235

140

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The frequency and intensity of harmful algal blooms (HABs) and phytoplankton community shifts toward toxic species have increased worldwide. Although most research has focused on eutrophication as the cause of this trend, many other global-and regional-scale anthropogenic influences may also play a role. Ocean acidification (high pCO 2 /low pH), greenhouse warming, shifts in nutrient availability, ratios, and speciation, changing exposure to solar irradiance, and altered salinity all have the potential to profoundly affect the growth and toxicity of these phytoplankton. Except for ocean acidification, the effects of these individual factors on harmful algae have been studied extensively. In this review, we summarize our understanding of the influence of each of these single factors on the physiological properties of important marine HAB groups. We then examine the much more limited literature on how rising CO 2 together with these other concurrent environmental changes may affect these organisms, including what is possibly the most critical property of many species: toxin production. New work with several diatom and dinoflagellate species suggests that ocean acidification combined with nutrient limitation or temperature changes may dramatically increase the toxicity of some harmful groups. This observation underscores the need for more in-depth consideration of poorly understood interactions between multiple global change variables on HAB physiology and ecology. A key limitation of global change experiments is that they typically span only a few algal generations, making it difficult to predict whether they reflect likely future decadal-or century-scale trends. We conclude by calling for thoughtfully designed experiments and observations that include adequate consideration of complex multivariate interactive effects on the long-term responses of HABs to a rapidly changing future marine environment.

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“…A similar pattern of acetate incorporation was observed with DTX-5c. 55 More recently, labeling studies with yessotoxin (23) conrmed that glycolate was also a starter unit for this ladder frame polyether 89 (Fig. 14).…”

Section: Starter Groups and Hybrid Moleculesmentioning

confidence: 91%

“…4), 46,48 and yessotoxin (23; Fig. 14), 89 and, due to the complexities involved in construction of nascent polyketide chains for polyethers, it is not straightforward to determine the direction of chain assembly from the structure of the nal metabolite alone. Another example is that of brevisamide (33) as noted above.…”

Section: Compounds Containing Isolated Ether Rings or Spiro Ring Asse...mentioning

confidence: 99%

Polyketide biosynthesis in dinoflagellates: what makes it different?

Wagoner¹,

Satake

Wright

2014

Nat. Prod. Rep.

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Dinoflagellates produce unique polyketides characterized by their size and complexity. The biosynthesis of a limited number of such metabolites has been reported, with studies largely hampered by the low yield of compounds and the severe scrambling of label in the isotopically-labeled precursors. Nonetheless, of the successful biosynthetic experiments that have been reported, many surprising and unique processes have been discovered. This knowledge has been accessed through a series of biochemical labeling studies, and while limited molecular genetic data has been amassed, it is still in the early stages of development. In an attempt to meet this challenge, this review has compared some of the biosynthetic processes with similar ones identified in other microbes such as bacteria and myxobacteria, with the idea that similar genes and enzymes are employed by dinoflagellates.

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Complete 13C-labeling pattern of yessotoxin a marine ladder-frame polyether

Cited by 15 publications

References 22 publications

Marine natural products

Marine natural products

Global change and the future of harmful algal blooms in the ocean

Polyketide biosynthesis in dinoflagellates: what makes it different?

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