The isolation and structures of unusual 1, 4-polyketides from the dinoflagellate, Amphidinium sp.

Bauer, Ines; Maranda, Lucie; Young, Kurt A.; Shimizu, Yuzuru; Huang, Stella

doi:10.1016/0040-4039(94)02423-9

Cited by 38 publications

(17 citation statements)

References 7 publications

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“…For example, such deletions are observed in amphidinolides (Rein & Snyder, 2006), and they are a hallmark of dinoflagellate polyketides. 3), also isolated from Amphidinium species (Bauer et al, 1995), may also be explained by C 1 deletions, although this has not been substantiated by incorporation of stable isotopes. One plausible mechanism involves the formation of an a-diketo group by a flavin-dependent monooxygenase, followed by a Favroskii rearrangement, a second oxidation step, and finally loss of a carbon atom by decarboxylation (Wright et al, 1996).…”

Section: Polyketides From Dinoflagellatesmentioning

confidence: 96%

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Microalgae in the postgenomic era: a blooming reservoir for new natural products

Sasso¹,

Pohnert²,

Lohr³

et al. 2012

FEMS Microbiol Rev

145

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Bacteria, fungi, algae and higher plants are the most prolific producers of natural products (secondary metabolites). Compared to macroalgae, considerably fewer natural products have been isolated from microalgae, which offer the possibility of obtaining sufficient and well-defined biological material from laboratory cultures. Interest in microalgae is reinforced by large-scale data sets from genome sequencing projects and the development of genetic tools such as transformation protocols. This review highlights what is currently known about the biosynthesis and biological role of natural products in microalgae, with examples from isoprenoids, complex polyketides, nonribosomal peptides, polyunsaturated fatty acids and oxylipins, alkaloids, and aromatic secondary metabolites. In addition, we introduce a bioinformatic analysis of available genome sequences from totally 16 microalgae, belonging to the green and red algae, heterokonts and haptophytes. The results suggest that the biosynthetic potential of microalgae is underestimated and many microalgal natural products remain to be discovered.

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Section: Polyketides From Dinoflagellatesmentioning

confidence: 96%

“…The 1,4-diketo moieties of amphidinoketides ( Fig. 3), also isolated from Amphidinium species (Bauer et al, 1995), may also be explained by C 1 deletions, although this has not been substantiated by incorporation of stable isotopes.…”

Section: Polyketides From Dinoflagellatesmentioning

confidence: 99%

Microalgae in the postgenomic era: a blooming reservoir for new natural products

Sasso¹,

Pohnert²,

Lohr³

et al. 2012

FEMS Microbiol Rev

145

View full text Add to dashboard Cite

show abstract

“…This is the third isolation of polyketide metabolites with a low molecular weight and no macrocyclic lactone ring from marine dinoflagellates Amphidinium sp., although amphidinin A [12] and amphidinoketides [13] have been isolated from dinoflagellates of the same genus. The backbone of 1 was the same as the carbon frameworks of 19-membered macrolides, amphidinolides T1, T3ϳT5.…”

Section: Physico-chemical Propertiesmentioning

confidence: 99%

Amphidinin B, a New Polyketide Metabolite from Marine Dinoflagellate Amphidinium sp.

et al. 2006

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“…gibbosum and A. carterae, have been reported to produce ichthyotoxins called amphidinols, amphidinolides, and caribenolides (Kobayashi et al 1991, Satake et al 1991, Bauer et al 1994, 1995a, Paul et al 1996, Houdai et al 2001. Amphidinolides have shown potential antitumor activity and are being investigated for use in the development of drugs against leukemia (Bauer et al 1994, 1995b, Williams and Meyer 2001, whereas amphidinols have shown antifungal activity (Satake et al 1991). The identification of species closely related to these would make new organisms available for future screening of bioactive substances.…”

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confidence: 99%

AMPHIDINIUM REVISITED. II. RESOLVING SPECIES BOUNDARIES IN THE AMPHIDINIUM OPERCULATUM SPECIES COMPLEX (DINOPHYCEAE), INCLUDING THE DESCRIPTIONS OF AMPHIDINIUM TRULLA SP. NOV. AND AMPHIDINIUM GIBBOSUM. COMB. NOV.¹

Murray

Jørgensen

Daugbjerg

et al. 2004

Journal of Phycology

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Amphidinium operculatum Claparède et Lachmann, the type species of the dinoflagellate genus Amphidinium, has long had an uncertain identity. It has been considered to be either difficult to distinguish from other similar species or a morphologically variable species itself. This has led to the hypothesis that A. operculatum represents a “species complex.” Recently, the problem of distinguishing A. operculatum from similar species has become particularly acute, because several morphologically similar species have been found to produce bioactive compounds of potential interest to the pharmaceutical industry. In this study, we cultured and examined existing cultures of several species of Amphidinium, most of which have been previously identified as A. operculatum or as species considered by some to be synonyms or varieties of A. operculatum. Thirty strains were examined using comparative LM, SEM, and partial large subunit (LSU) rDNA sequence data. Through morphological and molecular phylogenetic analyses, six distinct species were identified, including Amphidinium trulla sp. nov. and Amphidinium gibbosum comb. nov. Amphidinium operculatum was redescribed based on four cultures. Genetic variability within the examined Amphidinium species varied greatly. There was little difference among strains in partial LSU rDNA for most species, but strains of A. carterae and A. massartii Biencheler differed by as much as 4%. In both A. carterae and A. massartii, three distinct genotypes based on partial LSU rDNA were found, but no morphological differences among strains could be observed using LM or SEM. In the case of A. carterae, no biogeographically related molecular differences were found.

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The isolation and structures of unusual 1, 4-polyketides from the dinoflagellate, Amphidinium sp.

Cited by 38 publications

References 7 publications

Microalgae in the postgenomic era: a blooming reservoir for new natural products

Microalgae in the postgenomic era: a blooming reservoir for new natural products

Amphidinin B, a New Polyketide Metabolite from Marine Dinoflagellate Amphidinium sp.

AMPHIDINIUM REVISITED. II. RESOLVING SPECIES BOUNDARIES IN THE AMPHIDINIUM OPERCULATUM SPECIES COMPLEX (DINOPHYCEAE), INCLUDING THE DESCRIPTIONS OF AMPHIDINIUM TRULLA SP. NOV. AND AMPHIDINIUM GIBBOSUM. COMB. NOV.¹

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The isolation and structures of unusual 1, 4-polyketides from the dinoflagellate, Amphidinium sp.

Cited by 38 publications

References 7 publications

Microalgae in the postgenomic era: a blooming reservoir for new natural products

Microalgae in the postgenomic era: a blooming reservoir for new natural products

Amphidinin B, a New Polyketide Metabolite from Marine Dinoflagellate Amphidinium sp.

AMPHIDINIUM REVISITED. II. RESOLVING SPECIES BOUNDARIES IN THE AMPHIDINIUM OPERCULATUM SPECIES COMPLEX (DINOPHYCEAE), INCLUDING THE DESCRIPTIONS OF AMPHIDINIUM TRULLA SP. NOV. AND AMPHIDINIUM GIBBOSUM. COMB. NOV.1

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AMPHIDINIUM REVISITED. II. RESOLVING SPECIES BOUNDARIES IN THE AMPHIDINIUM OPERCULATUM SPECIES COMPLEX (DINOPHYCEAE), INCLUDING THE DESCRIPTIONS OF AMPHIDINIUM TRULLA SP. NOV. AND AMPHIDINIUM GIBBOSUM. COMB. NOV.¹