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The genus Amphidinium is shown in many phylogenies to be basal to other peridinin-containing, photosynthetic dinoflagellates as one of the first photosynthetic genera to arise after the evolution of heterotrophic genera. As part of our continuing examination of the plastid-associated galactolipids, namely mono- and digalactosyldiacylglycerol (MGDG and DGDG, respectively), in dinoflagellates, we here examine the galactolipid composition of members of the genus Amphidinium. We show that this genus is characterized by an abundance of 20:5(n-3)/18:5(n-3) and 20:5(n-3)/18:4(n-3) forms of MGDG and DGDG (with sn-1/sn-2 regiochemical specificity of fatty acids), but also sometimes with generally lesser amounts of some polyunsaturated C18/C18 forms, thus placing the examined species within a previously identified cluster of C20/C18 MGDG- and DGDG-containing, peridinin-containing dinoflagellates. We also show that Testudodinium testudo, previously known as Amphidinium testudo, conversely falls within a previously identified C18/C18 cluster, indicating a distinct difference in galactolipid biosynthesis capability. While it is likely that further revision of the genus may occur in the future and/or more basal peridinin-containing, photosynthetic genera may be discovered, at the current time Amphidinium is the currently agreed-upon most basal dinoflagellate genus for which isolates are available for biochemical characterization such as what we describe in this paper. Thus, because of the presumed basal position of the genus Amphidinium, we present a hypothesis that its galactolipids currently represent those that are ancestral to other genera of peridinin-containing dinoflagellates, including those within the C18/C18 cluster. Amphidinium species' galactolipids reside within the C20/C18 peridinin dinoflagellate cluster. Conversely, Testudodinium testudo (formerly Amphidinium testudo) falls within the C18/C18 cluster. We hypothesize Amphidinium's galactolipids as basal to other peridinin dinoflagellates. [ABSTRACT FROM AUTHOR]

The dinoflagellates Amphidinium carterae and Amphidinium corpulentum have been previously characterized as having Δ8(14)‐nuclear unsaturated 4α‐methyl‐5α‐cholest‐8(14)‐en‐3β‐ol (C28:1) and 4α‐methyl‐5α‐ergosta‐8(14),24(28)‐dien‐3β‐ol (amphisterol; C29:2) as predominant sterols, where they comprise approximately 80% of the total sterol composition. These two sterols have hence been considered as possible major sterol biomarkers for the genus. Here, we have examined the sterols of four recently identified species of Amphidinium (Amphidinium fijiense, Amphidinium magnum, Amphidinium theodori, and Amphidinium tomasii) that are closely related to Amphidinium operculatum as part of what is termed the Operculatum Clade to show that each species has its sterol composition dominated by the common dinoflagellate sterol cholesterol (cholest‐5‐en‐3β‐ol; C27:1), which is found in many other dinoflagellate genera, rather than Δ8(14) sterols. While the Δ8(14) sterols 4α‐methyl‐5α‐cholest‐8(14)‐en‐3β‐ol and 4α,23,24‐trimethyl‐5α‐cholest‐8(14),22E‐dien‐3β‐ol (C30:2) were present as minor sterols along with another common dinoflagellate sterol, 4α,23,24‐trimethyl‐5α‐cholest‐22E‐en‐3β‐ol (dinosterol; C30:1), in some of these four species, amphisterol was not conclusively observed. From a chemotaxonomic perspective, while this does reinforce the genus Amphidinium's ability to produce Δ8(14) sterols, albeit here as minor sterols, these results demonstrate that caution should be used when considering Δ8(14) sterols, especially amphisterol, as Amphidinium‐specific biomarkers within these species where cholesterol is the predominant sterol. [ABSTRACT FROM AUTHOR]

Prorocentrum texanum var. texanum and its morphologically distinct yet genetically identical (as based on the sequences of five genes) variety P. texanum var. cuspidatum represent a species of Prorocentrum recently isolated from the Gulf of Mexico. Together, these two varieties represent a sister species to Prorocentrum micans. P. micans has had its sterols, which are ringed lipids common to eukaryotic cell membranes, shown in some studies to be comprised of cholesterol (cholest‐5‐en‐3β‐ol), 23,24‐dimethyl‐cholesta‐5,22‐dien‐3β‐ol, 23,24‐dimethyl‐5α‐cholest‐22E‐en‐3β‐ol, dinosterol, and 4α,23,24‐trimethyl‐5α‐cholestan‐3β‐ol (dinostanol) as major sterols, thus placing it within a previously identified cluster of dinoflagellates characterized by the predominance of cholesterol and dinosterol. In this study we have determined the sterol compositions of these two varieties of P. texanum to be abundant in cholesterol, 23,24‐dimethyl‐cholesta‐5,22‐dien‐3β‐ol, 23,24‐dimethyl‐5α‐cholest‐22E‐en‐3β‐ol, dinosterol, and dinostanol such that the varieties are virtually indistinguishable from each other, making them both in general agreement with the sterols of P. micans, its closest species relative. This expands our knowledge of the sterols of this environmentally important dinoflagellate genus. [ABSTRACT FROM AUTHOR]

Testudodinium testudo is a peridinin‐containing dinoflagellate recently renamed from Amphidinium testudo. While T. testudo has been shown via phylogenetic analysis of small subunit ribosomal RNA genes to reside in a clade separate from the genus Amphidinium, it does possess morphological features similar to Amphidinium sensu stricto. Previous studies of Amphidinium carterae and Amphidinium corpulentum have found the sterols to be enriched in Δ8(14) sterols, such as 4α‐methyl‐5α‐ergosta‐8(14),24(28)‐dien‐3β‐ol (amphisterol), uncommon to most other dinoflagellate taxa and thus considered possible biomarkers for the genus Amphidinium. Here, we provide an examination of the sterols of T. testudo and show they are dominated not by amphisterol, but rather by a different Δ8(14) sterol, (24R)‐4α‐methyl‐5α‐ergosta‐8(14),22‐dien‐3β‐ol (gymnodinosterol), previously thought to be a major sterol only within the Kareniaceae genera Karenia, Karlodinium, and Takayama. Also found to be present at low levels were 4α‐methyl‐5α‐ergosta‐8,14,22‐trien‐3β‐ol, a sterol previously observed in Karenia brevis to be an intermediate in the production of gymnodinosterol, and cholesterol, a sterol common to many other dinoflagellates. The presence of gymnodinosterol in T. testudo is the first report of this sterol as the sole major sterol in a dinoflagellate outside of the Kareniaceae. The implication of this chemotaxonomic relationship to the Kareniaceae is discussed. [ABSTRACT FROM AUTHOR]

SUMMARY: Gertia stigmatica is an atypical member of the Kareniaceae that has a peridinin‐containing plastid rather than a tertiary, (acyloxy)fucoxanthin‐containing, haptophyte‐derived plastid, as is found in the canonical genera Karenia, Karlodinium, and Takayama. While the origin of G. stigmatica's plastid is uncertain per its original published description, with alternative hypotheses stating that it could have originated before or after the acquisition of a haptophyte‐derived plastid, the description of the species indicates that it does possess ultrastructural and genetic features that firmly place it within the Kareniaceae. As a photosynthetic, plastid‐containing organism, G. stigmatica, like other algae, possesses two galactolipids, mono‐ and digalactosyldiacylglycerol (MGDG and DGDG, respectively), that form the basis of its plastid‐associated photosynthetic membranes. MGDG and DGDG have been extensively characterized in peridinin‐containing dinoflagellates, where it has been observed that these dinoflagellates can be segregated into two clusters. One cluster is characterized by MGDG and DGDG possessing the polyunsaturated C18/C18 fatty acids (sn‐1/sn‐2 regiochemistry) octadecapentaenoic acid (18:5(n‐3)) and octadecatetraenoic acid (18:4(n‐3)), while the second cluster possesses eicosapentaenoic acid (20:5(n‐3)) in the sn‐1 position while retaining a polyunsaturated C18 fatty acid in the sn‐2 position. By contrast, Karenia brevis and Karenia mikimotoi have been observed to be enriched in species of MGDG and DGDG, such as 18:5(n‐3)/14:0 MGDG and DGDG, uncommon to peridinin‐containing dinoflagellates. Our objective was to characterize the galactolipids of G. stigmatica to compare it to both peridinin‐containing dinoflagellates and other members of the Kareniaceae to search for insight, such as (a) remnant 14:0 fatty acid‐containing galactolipid(s), into the evolution of its plastid. Our results show that G. stigmatica possesses 20:5(n‐3)/18:5(n‐3) MGDG and DGDG as the primary galactolipids, with little evidence of those galactolipid species enriched in K. brevis and K. mikimotoi. The implications of this for the evolution of the G. stigmatica plastid are discussed. [ABSTRACT FROM AUTHOR]

SUMMARY: 'Dinotoms' are a relatively small group of dinoflagellates with aberrant tertiary plastids of diatom origin, thus differing from the majority of photosynthetic dinoflagellates which possess the carotenoid pigment peridinin and have secondary plastids of red algal origin. As part of our laboratory's continuing efforts to examine such unusual dinoflagellates in the search for clues to the evolution of their lipid compositions, we have examined the sterol composition of the dinotom Durinskia baltica. As such, we here compared its sterols to those of the previously examined dinotom, Kryptoperidinium foliaceum, more broadly to other photosynthetic, peridinin‐containing dinoflagellates, and to the diatom genus Nitzschia, which is the presumed ancestor of the D. baltica dinotom plastid. Sterols are ringed lipids, common to eukaryotes, thought to reinforce phospholipid bilayers. Many peridinin‐containing dinoflagellates have sterol compositions which are enriched by the presence of cholesterol (cholest‐5‐en‐3β‐ol) and 4α‐methyl‐substituted sterols such as dinosterol (4α,23,24‐trimethyl‐5α‐cholest‐22E‐en‐3β‐ol); this has also been found to be true for K. foliaceum despite its aberrant plastid ancestry. Our objective was to determine if this is also true for D. baltica as only the second dinotom to have its sterols characterized in detail, and to determine if there is any indication of prominent sterols which are uncommon to dinoflagellates, possibly originating from the diatom endosymbiont, as has been demonstrated previously with K. foliaceum and D. baltica chloroplast‐associated galactolipids of clear diatom origin. Our results demonstrate that like K. foliaceum, the major sterols of D. baltica are cholesterol, dinosterol, and other 4α‐methyl‐substituted sterols common to dinoflagellates. Although there were a number of minor sterols, none were found with obvious origin from the diatom endosymbiont, indicating that most originated with the dinoflagellate host itself, most likely before acquisition of the diatom tertiary plastid. [ABSTRACT FROM AUTHOR]

Pyrodinium bahamense is a dinoflagellate of concern in subtropical and tropical coastal environments. To date, there is only a single published study on its fatty acids, but no published data on its sterol composition. Sterols, which are membrane‐reinforcing lipids in eukaryotes, display a great diversity of structures in dinoflagellates, with some serving as chemotaxonomic markers. We have examined the sterol compositions of two isolates of P. bahamense from Indian River Lagoon and Tampa Bay, Florida, and have found both to produce three sterols: cholesterol, dinosterol, and 4α‐methylgorgostanol. All three sterols are found in closely related, armored taxa. [ABSTRACT FROM AUTHOR]

Previous studies have shown that dinoflagellates with different plastid ancestries have distinct differences in the fatty acid compositions and regiochemistries of their chloroplast-associated galactolipids, mono- and digalactosyldiacylglycerol (MGDG and DGDG, respectively), thus reflecting plastid origin as a major factor in plastid membrane composition. Specifically, dinoflagellates with aberrant plastids (e.g. Karenia brevis, Kryptoperidinium foliaceum and Lepidodinium chlorophorum) possess certain MGDG- and DGDG-associated fatty acids which are not found in peridinin-containing dinoflagellates (the largest group of photosynthetic dinoflagellates with a red algal plastid ancestry which is thought to be an evolutionary precursor to aberrant plastids), but which are common to other algal groups. For example, hexadecatetraenoic acid (16:4(n-3)) is common to green algae and is found in the MGDG and DGDG of L. chlorophorum, which agrees with its green algal plastid ancestry, while hexadecatrienoic acid (16:3) and hexadecadienoic acid (16:2) are found in the MGDG and DGDG of K. foliaceum, which agrees with its diatom plastid ancestry. Notably, 16:4 has been found by others in the total fatty acids and galactolipids of Karenia mikimotoi, but in no other examined members of the Kareniaceae (all of which have plastids of haptophyte origin). However, these findings lack information as to the regiochemistry of 16:4. We have utilized positive-ion electrospray ionization/mass spectrometry (ESI/MS) and ESI/MS/MS to demonstrate that 16:4, which aside from L. chlorophorum is not found conclusively in the MGDG and DGDG of any other dinoflagellates examined to date irrespective of plastid ancestry, is found in K. mikimotoi as 18:5/16:4 (sn-1/sn-2 regiochemistry) MGDG and DGDG, and that its presence is not modulated (i.e. does not become more saturated) with an increase in growth temperature. Considering an aberrant pigment composition as described by others, we present a perspective where galactolipid-associated 16:4 in K. mikimotoi indicates a plastid ancestry more convoluted than for other members of the Kareniaceae. [ABSTRACT FROM AUTHOR]