Genus Amphidinium Research Articles

Bispinodinium angelaceum gen. et sp. nov. (Dinophyceae), a new sand-dwelling dinoflagellate from the seafloor off Mageshima Island, Japan(1).

A new athecate dinoflagellate, Bispinodinium angelaceum N. Yamada et Horiguchi gen. et sp. nov., is described from a sand sample collected on the seafloor at a depth of 36m off Mageshima Island, subtropical Japan. The dinoflagellate is dorsiventrally compressed and axi-symmetric along the sulcus. The morphology resembles that of the genus Amphidinium sensu lato by having a small epicone that is less than one third of the total cell length. However, it has a new type of apical groove, the path of which traces the outline of a magnifying glass. The circular component of this path forms a complete circle in the center of the epicone and the straight "handle" runs from the sulcus to the circular component. Inside the cell, a pair of elongated fibrous structure termed here the "spinoid apparatus" extends from just beneath the circular apical groove to a point near the nucleus. Each of two paired structures consists of at least 10 hyaline fibers and this is a novel structure found in dinoflagellates. Phylogenetic analyses based on the SSU and LSU RNA genes did not show any high bootstrap affinities with currently known athecate dinoflagellates. On the basis of its novel morphological features and molecular signal, we conclude that this dinoflagellate should be described as a new species belonging to a new genus.

MORPHOLOGY AND MOLECULAR PHYLOGENY OF ANKISTRODINIUM GEN. NOV. (DINOPHYCEAE), A NEW GENUS OF MARINE SAND-DWELLING DINOFLAGELLATES FORMERLY CLASSIFIED WITHIN AMPHIDINIUM(1).

The classical athecate dinoflagellate genera (Amphidinium, Gymnodinium, Gyrodinium) have long been recognized to be polyphyletic. Amphidinium sensu lato is the most diverse of all marine benthic dinoflagellate genera; however, following the redefinition of this genus ∼100 species remain now of uncertain or unknown generic affiliation. In an effort to improve our taxonomic and phylogenetic understanding of one of these species, namely Amphidinium semilunatum, we re-investigated organisms from several distant sites around the world using light and scanning electron microscopy and molecular phylogenetic methods. Our results enabled us to describe this species within a new heterotrophic genus, Ankistrodinium. Cells of A.semilunatum were strongly laterally flattened, rounded-quadrangular to oval in lateral view, and possessed a small asymmetrical epicone. The sulcus was wide and characteristically deeply incised on the hypocone running around the antapex and reaching the dorsal side. The straight acrobase with hook-shaped end started at the sulcal extension and continued onto the epicone. The molecular phylogenetic results clearly showed that A.semilunatum is a distinct taxon and is only distantly related to species within the genus Amphidinium sensu stricto. The nearest sister group to Ankistrodinium could not be reliably determined.

Testudodinium gen. nov. (Dinophyceae), a new genus of sand‐dwelling dinoflagellates formerly classified in the genus Amphidinium

SUMMARYA new genus of sand‐dwelling photosynthetic dinoflagellate, Testudodinium Horiguchi, Tamura, Katsumata et A. Yamaguchi is proposed based on Testudodinium testudo (Herdman) Horiguchi, Tamura, Katsumata, et A. Yamaguchi comb. nov. (Basionym: Amphidinium testudo Herdman) and a new species in this new genus, Testudodinium maedaense Katsumata et Horiguchi sp. nov. is described. Amphidinium corrugatum is also transferred to this genus, making a new combination T. corrugatum (Larsen et Patterson) Horiguchi, Tamura et A. Yamaguchi. These three species are similar to the members of the genus Amphidinium in having an extremely small episome and a dorsoventrally flattened cell body. They are, however, distinguished from the genus Amphidinium seusu stricto by the possession of a distinct longitudinal furrow in the middle of ventral side of the episome. Phylogenetic trees based on small subunit (SSU) rDNA revealed that all three of these Testudodinium species formed a robust clade and, although statistical support is not high, the tree suggests Testudodinium clade is not closely related to Amphidinium seusu stricto clade. The morphological differences together with molecular data support the establishment of a new genus for A. testudo and its related species.

Iriomoteolide-12a, a 12-membered macrolide from dinoflagellate Amphidinium species

Marine dinoflagellates of the genus Amphidinium are well-known as a producer of unique cytotoxic metabolites. We have isolated a new 12-membered macrolide, iriomoteolide-12a, from the benthic dinoflagellate Amphidinium species collected off Iriomote Island, Japan. In this symposium, we will discuss the isolation and structural elucidation of this new macrolide.

Synthesis of Amphidinolide X

Amphidinolide X is one of many ­cytotoxic macrolides isolated from marine dino-flagellates of the genus Amphidinium. A silicon-tethered cross-metathesis was necessary to construct the C12-C13 E double bond after standard ring-closing metathesis failed to give the correct double bond geometry.

Total Syntheses of Amphidinolides B1, B4, G1, H1 and Structure Revision of Amphidinolide H2

Nature is a pretty unselective "chemist" when it comes to making the highly cytotoxic amphidinolide macrolides of the B/G/H series. To date, 16 different such compounds have been isolated, all of which could now be approached by a highly convergent and largely catalysis-based route (see figure). This notion is exemplified by the total synthesis of five prototype members of this family.Dinoflagellates of the genus Amphidinium produce a "library" of closely related secondary metabolites of mixed polyketide origin, which are extremely scarce but highly promising owing to the exceptional cytotoxicity against various cancer cell lines. Because of the dense array of sensitive functionalities on their largely conserved macrocyclic frame, however, these amphidinolides of the B, D, G and H types elapsed many previous attempts at their synthesis. Described herein is a robust, convergent and hence general blueprint which allowed not only to conquest five prototype members of these series, but also holds the promise of making "non-natural" analogues available by diverted total synthesis. This notion transpires for a synthesis-driven structure revision of amphidinolide H2. The successful route hinges upon a highly productive Stille-Migita cross-coupling reaction at the congested and chemically labile 1,3-diene site present in all such targets, which required the development of a modified chloride- and fluoride-free protocol. The macrocyclic ring could be formed with high efficiency and selectivity by ring-closing metathesis (RCM) engaging a vinyl epoxide unit as one of the reaction partners. Because of the sensitivity of the targets to oxidizing and reducing conditions as well as to pH changes, the proper adjustment of the protecting group pattern for the peripheral -OH functions also constitutes a critical aspect, which has to converge to silyl groups only once the diene is in place. Tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) turned out to be a sufficiently mild fluoride source to allow for the final deprotection without damaging the precious macrolides.

Amphidinolides and Its Related Macrolides from Marine Dinoflagellates

This review covers the recent results described in our publications on several new cytotoxic macrolides isolated from dinoflagellates of the genus Amphidinium in addition to an overview of the isolation, structure elucidation, synthesis, biosynthesis, and bioactivity of a series of cytotoxic macrolides, named amphidinolides, reported so far.

Comparative Morphology and Molecular Phylogeny of Apicoporus n. Gen.: A New Genus of Marine Benthic Dinoflagellates Formerly Classified within Amphidinium

The composition of the dinoflagellate genus Amphidinium is currently polyphyletic and includes several species in need of re-evaluation using modern morphological and phylogenetic methods. We investigated a broad range of uncultured morphotypes extracted from marine sediments in the Eastern Pacific Ocean that were similar in morphology to Amphidinium glabrum Hoppenrath and Okolodkov. To determine the number of distinct species associated with this phenotypic diversity, we collected LM, SEM, TEM and small subunit ribosomal DNA sequence information from different morphotypes, including the previously described A. glabrum. Both comparative morphological and molecular phylogenetic data supported the establishment of a new genus, Apicoporus n. gen., including at least two species, A. glaber n. comb., and A. parvidiaboli n. sp. Apicoporus is characterized by having amphiesmal pores and an apical pore covered by a hook-like protrusion; neither of these characters has been observed in other athecate dinoflagellates. The posterior end of Apicoporus parvidiaboli possessed varying degrees of "horn formation", ranging from slight to prominent. By contrast, the posterior end of Apicoporus glaber was distinctively rounded and lacked evidence of horn formation. Although these species were previously interpreted to be obligate heterotrophs, TEM and epifluorescence microscopy demonstrated that some cells of both species had unusually small but otherwise typical dinoflagellate plastids. The number and density of plastids in any particular cell varied significantly in the genus, but the plastids were almost always concentrated at the posterior end of the cells or around the nucleus. The presence of cryptic photosynthetic plastids in these benthic species suggests that photosynthesis might be much more widespread in dinoflagellates than is currently assumed.

Three party symbiosis: acoelomorph worms, corals and unicellular algal symbionts in Eilat (Red Sea)

Epizoic worms were found to occur on certain coral colonies from reefs off the coast of Eilat (Red Sea). We identified 14 coral species infested by acoelomorph worms at a depth range of 2–50 m. The host corals were all zooxanthellate and included both massive and branching stony corals and a soft coral. Worms from all hosts were identified as belonging to the genus Waminoa and contained two distinct algal symbionts differing in size. The smaller one was identified as Symbiodinium sp. and the larger one is presumed to belong to the genus Amphidinium. Worm-infested colonies of the soft coral, Stereonephthya cundabiluensis, lacked a mucus layer and exhibited distinct cell microvilli, a phenotype not present in colonies lacking Waminoa sp. In most cases, both cnidarian and Acoelomorph hosts displayed high specificity for genetically distinctive Symbiodinium spp. These observations show that the epizoic worms do not acquire their symbionts from the “host” coral.

On the freshwater dinoflagellates presently included in the genus Amphidinium, with a description of Prosoaulax gen. nov.

A.J. Calado and Ø. Moestrup. 2005. On the freshwater dinoflagellates presently included in the genus Amphidinium, with a description of Prosoaulax gen. nov. Phycologia 44: 112–119.Amphidinium is a genus of naked dinoflagellates, characterized by a small epicone and a larger hypocone. Presently about 120 species from both freshwater and marine biotopes have been described. The genus has long been known to be poly-phyletic, however, and the recent rediscovery of the type species has now allowed for more precise definition of the genus. The new circumscription of the genus leaves the freshwater species without a generic name. A new generic name, Prosoaulax gen. nov., is therefore proposed for the first described freshwater species, Amphidinium lacustre Stein (1883), and related species. Based on ultrastructural features, notably the very unusual type of eyespot, Prosoaulax is considered to be related to a recently recognized, but poorly understood group of dinoflagellates, comprising the marine species Gymnodinium simplex, G. natalense, Polarella antarctica, and some symbionts of marine invertebrates, G. bei and G. linucheae. It also includes the symbionts of corals (‘zooxanthellae’) belonging to the genus Symbiodinium, a genus believed to contain the modern representatives of the Suessiales, an order of dinoflagellates extending back into the Mesozoic.

Amphidinolides, Bioactive Macrolides from Symbiotic Marine Dinoflagellates

AbstractFor Abstract see ChemInform Abstract in Full Text.

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

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.

AMPHIDINIUM REVISITED. I. REDEFINITION OF AMPHIDINIUM (DINOPHYCEAE) BASED ON CLADISTIC AND MOLECULAR PHYLOGENETIC ANALYSES1

Members of Amphidinium Claparède and Lachmann constitute a major part of sand‐dwelling benthic dinoflagellates worldwide. The genus is traditionally defined by its small epicone size, not exceeding one third of the total cell length. It has long been suspected that this functional definition does not reflect phylogeny, yet the problem of identifying the type species A. operculatum and closely related species has until now hindered attempts to redefine the genus. In this study 12 Amphidinium species were examined using phylogenetic analyses based on nuclear‐encoded, partial, large subunit (LSU) rDNA, with a further six Amphidinium species being included in a morphological cladistic analysis. The species selected represented taxa with a range of morphological dissimilar epicone forms. Both cladistic analysis and analyses based on partial LSU rDNA revealed that Amphidinium species with minute left‐deflected epicones formed a monophyletic clade that included the type species. Amphidinium species with other epicone types were found to be unrelated to this clade. The type species A. operculatum was identified based on general cell shape and size, position of a dark organelle previously defined as a stigma, and origin of the sulcus. The description of A. elegans by Grell and Wohlfarth‐Bottermann was found to be identical to it. A species fitting the original description of A. operculatum was cultured and included in the analyses. Based on cladistic and molecular analyses, it grouped together with all other species with minute left‐deflected epicones, and this group constitutes the true genus Amphidinium sensu stricto. An emendation of the genus definition is presented.

Amphidinolides, bioactive macrolides from symbiotic marine dinoflagellates.

This review covers the structures, synthesis, biosynthesis, and bioactivity of a series of cytotoxic macrolides, named amphidinolides, isolated from symbiotic marine dinoflagellates of the genus Amphidinium which were separated from inside cells of marine flatworms. The structures of long-chain polyketides such as colopsinols isolated from Amphidinium sp. are also described.

A novel type of body scale found in two strains of Amphidinium species (Dinopbyceae)

A novel type of body scale has been found in two strains of unidentified species of the dinoflagellate genus Amphidinium. The body scales are distributed over the entire outer surface of the plasma membrane of the cells, and are embedded in an amorphous material. No scales are present on the flagellar membrane. The body scales are oval, uniform and simple, and lack a basal plate; they are similar in shape in the two species, but differ in size. Scale formation takes place within the Golgi cisternae. The mature scales are then transported to the vicinity of the flagellar canal in Golgi vesicles in the cytoplasm, where they are extruded out of the cell. These two species are morphologically indistinguishable from Amphidinium carterae except by the presence of scales, and this distinction is supported by base pair differences in the small subunit ribosomal RNA (SSU rRNA) gene (28–29 base alterations). We consider the two strains to be different species on the basis of differences in the size of the cells, the dimensions of the body scales, the occurrence of plate-like structures in amphiesmal vesicles and the base pair sequences of the SSU rRNA gene.

The benthic dinoflagellate genus Amphidinium in south-eastern Australian waters, including three new species

Seventeen species of the mainly sand-dwelling genus Amphidinium are reported from south-eastern Australian waters. Three new species are described: A. boggayum, A. mootonorum and A. yuroogurrum. Additional features from previously described species are presented, including non-motile cell stages. Nine of these species are new records for Australia; however, these species are probably widespread and common. Two potentially ichthyotoxic species of Amphidinium were commonly found: A. carterae and A. cf. operculatum. A table of morphological characters is compiled as a step towards recognizing new characters with which to group species of this presently artificially defined unarmoured dinoflagellate genus.

ChemInform Abstract: Amphidinolides T2, T3, and T4, New 19‐Membered Macrolides from the Dinoflagellate Amphidinium sp. and the Biosynthesis of Amphidinolide T1.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Amphidinolides T2, T3, and T4, new 19-membered macrolides from the dinoflagellate Amphidinium sp. and the biosynthesis of amphidinolide T1.

Three new 19-membered macrolides, amphidinolides T2 (2), T3 (3), and T4 (4), structurally related to amphidinolide T1 (1) have been isolated from two strains of marine dinoflagellates of the genus Amphidinium. The structures of 2-4 were elucidated on the basis of spectroscopic data. The absolute configurations at C-7, C-8, and C-10 of 1-4 were determined by comparison of NMR data of their C-1-C-12 segments with those of synthetic model compounds for the tetrahydrofuran portion. The biosynthetic origins of amphidinolide T1 (1) were investigated on the basis of 13C NMR data of a 13C enriched sample obtained by feeding experiments with [1-(13)C], [2-(13)C], and [1,2-(13)C2] sodium acetates and 13C-labeled sodium bicarbonate in the cultures of the dinoflagellate. These incorporation patterns suggested that amphidinolide T1 (1) was generated from four successive polyketide chains, an isolated C1 unit formed from C-2 of acetates, and three unusual C2 units derived only from C-2 of acetates. Furthermore, it is noted that five oxygenated carbons of C-1, C-7, C-12, C-13, and C-18 were not derived from the C-1 carbonyl, but from the C-2 methyl of acetates.

Phylogeny of some of the major genera of dinoflagellates based on ultrastructure and partial LSU rDNA sequence data, including the erection of three new genera of unarmoured dinoflagellates

Evidence from partial large-subunit (LSU) rDNA sequencing has been combined with ultrastructure, including details of the flagellar apparatus, in a number of phototrophic dinoflagellates, with the aim of trying to solve some of the most pressing taxonomic problems and to contribute to an improved understanding of the phylogeny within the group. Special attention has been paid to the unarmoured (naked) genera, many of which were described during the 1800s or early 1900s and whose taxonomy is artificial and misleading. This is particularly unsatisfactory because many of the species cause extensive plankton blooms, fish kills and other harmful events. Our studies have indicated that the path of the so-called apical groove (acrobase) is of particular importance for the taxonomy of the unarmoured genera of dinoflagellates. Features presently used to characterize many of the genera, such as the relative size of the epicone and hypocone, are misleading. Our data have resulted in the splitting of the large genus Gymnodinium into four genera. The fish-killing species are confined to two genera, Karenia G. Hansen & Moestrup gen. nov. and Karlodinium J. Larsen gen. nov. The paralytic shellfish poisoning-producing species Gymnodinium catenatum is retained within Gymnodinium, together with a number of harmless species. The fourth genus, Akashiwo G. Hansen & Moestrup gen. nov., presently comprises only the large nontoxic species previously known as Gymnodinium sanguineum. The genus Gyrodinium is redefined. The genus Amphidinium is artificial, but more data are needed before redescription of the genus can be made with any confidence. Within the armoured dinoflagellates, LSU and previously published small-subunit rDNA data show the Gonyaulacales to be a natural group. Peridiniella catenata, sometimes included in the Gonyaulacales based on gross morphology, falls outside this order both genetically and ultrastructurally. Based on the DNA data, the genus Peridinium appears to be artificial. Ultrastructure as well as gene sequences confirm that the genus Heterocapsa is unusual, since it includes both apparently unarmoured species (but with very thin plates) and armoured species.

Amphidiniella sedentaria gen. et sp. nov. (Dinophyceae), a new sand‐dwelling dinoflagellate from Japan

SUMMARYA new sand‐dwelling dinoflagellate is described from Sesoko Beach, Okinawa Island, subtropical Japan and its micromorphology is studied by means of light and electron microscopy. The cell consists of a small epitheca and a large hypothecs superficially resembling members of the unarmored genus Amphidinium. The cell is dorso‐ventrally flattened and possesses a single chloroplast with a large conspicuous pyrenoid. Transmission electron microscopy revealed that the dinoflagellate possesses typical dinoflagellate cellular organization. Scanning electron microscopy demonstrated that the organism is thecate and the thecal plate arrangement is Po, 4′, 1a, 7″, 5c, 4s, 6″′, 2″″. Most of the characteristics suggest gonyaulacalean affinity of the new species. These are the presence of ventral pore, lack of canal plate, direct contact between the sulcal anterior plate and the flagellar pore, possession of six postcingular plates and asymmetrical arrangement of the antapical plates. Affinity to existing families of the order Gonyaulacales has not been determined. Based on the unique cell shape, thecal plate arrangement and the presence of ventral pore, a new genus, Amphidiniella, is established for this organism and the species is named A. sedentaria Horiguchi gen. et sp. nov.