Pigments and fatty acids of marine raphidophytes: A chemotaxonomic re-evaluation

The patterns of occurrence of photosynthetic pigments and fatty acids among seven available species (11 strains) of marine raphidophytes were determined and used as chemotaxonomic markers. All currently recognized genera of marine raphidophytes were included for analysis: that is, Chattonella, Fibrocapsa, Heterosigma, Olisthodiscus and Haramonas. The characteristic pigment composition was shown to be chlorophyll a, chlorophylls c₁ and/or c₂, fucoxanthin as the major carot-enoid, β,β-carotene and any or all of zeaxanthin, violaxanthin and an auroxanthin-like pigment as the minor carotenoids. The carotenoid composition of all marine raphidophyte genera investigated was virtually the same, except in Fibrocapsa and Haramonas, which differed due to the occurrence of fucoxanthinol and 19′-butanoyloxyfucoxanthin, respectively. These fucoxanthin derivatives, in addition to fucoxanthin, have potential chemotaxonomic use for differentiating the two species. In all 11 strains, 15 fatty acids (saturated, mono-unsaturated and polyunsaturated) were determined. Significant taxonomic distinctions between genera were reflected by their fatty acid profiles. A rapid key for the differentiation of genera, in addition to morphological features, may be the absence of the 18:4 fatty acid in Olisthodiscus; presence of 18:5 in Heterosigma; the presence of fucoxanthinol in Fibrocapsa and presence of 19′-butanoyloxyfucoxanthin in Haramonas.     

A chemometric comparison of three taxa of Scabiosa L.s.l.

ABSTRACT

A comparative chemometric study of three taxa of the genus Scabiosa L. s. lato (Dipsacaceae) from Greece, treated so far as separate genera by some authors and as separate sections of a single genus by others, was carried out. The HPLC chemical fingerprint, based on several phenolic compounds (flavonoids and caffeic acid), was investigated in the three a forementioned taxa. The results support the contention that there is a close relationship between S. atropurpurea subsp. maritima and S. tenuis, and that S. argentea seems to be well separated from the other two taxa.     

The sterol and fatty acid compositions of seven tropical seagrasses from North Queensland,Australia

The sterol and fatty acid compositions of fresh leaves of the seagrasses Cymodocea serrulata, Enhalus acoroides, Halodule uninervis, Halophila ovalis, H. ovata, H. spinulosa and Thalassia hemprichii are reported. The major fatty acids were palmitic acid, linoleic acid and linolenic acid as expected. H. ovalis and H. ovata were characterized by the relatively high abundance (ca 5%) of the acid hexadeca-7,10,13-trienoic acid (16:3<7 > ). The sterol compositions were typical of higher plants, with sitosterol and stigmasterol accounting for 60–90% of the observed sterols. 28-Isofucosterol was a major sterol (20–30%) only in the Halophila spp. Cluster analysis of the sterol composition data clearly separated the Halophila spp. from the other seagrasses and enabled the distinction of Enhalus sp. from Cymodocea, Halodule and Thalassia spp. The seagrass species were clearly separated into five chemical groups using the combined fatty acid and sterol composition data and the need for a reappraisal of the taxonomic position of Halophila was indicated.     

中国桑寄生科植物化学分类学研究

用薄层层析 (TLC)方法对中国产桑寄生科植物的 2 7个分类种 (包括变种 )进行了初步的化学分类研究。TLC结果表明 :槲寄生类植物各种均具有齐墩果酸 ,且在Rf=0 .5附近存在特征性斑点群 ,桑寄生类植物均存在槲皮素。根据TLC图谱 ,采用SPSS系统进行了聚类分析研究     

中国东北川续断科两个新变型

发表了东北产川续断科蓝盆花属两个新变型,即白花窄叶蓝盆花(Scabiosa comosa Fisch. ex Roem. et Schult. f. albiflora S. H. Liet S. Z. Liu)和白花华北蓝盆花(S. tschiliensis Grun. f. albiflora S. H. Liet S. Z. Liu).两个变型与原变型的主要区别为花为白色。     

The uropygial gland secretions of birds of the family sylviidae

The preen gland secretions from eight species of the genera Acrocephalus and Sylvia (Sylviidae, Passeriformes) mainly consist of monoester waxes. The fatty acids and alcohols are methyl-substituted at even numbered positions only. One of the methyl groups of the fatty acids is always located in the 2-position. Two patterns of methyl substitution are found for the alkanols: $\text{2-}\text{mono-}$, $\text{2,6-di-}$, and $\text{2,6,x-}\text{trimethyl}$ on the one hand, and 4-mono-, 4,8-di-, and 4,8,$\text{y-}\text{trimethyl}$ on the other. There is, however, no doubt in the uniformity of the family Sylviidae from the chemotaxonomical point of view; the waxes of the species investigated can be arranged in a gradual succession of substitution patterns. The monoester waxes of Sylviidae are similar to those found for the closely related family Turdidae.     

Intra-and interspecific variability of fatty acid composition of soft corals

The intra-and interspecific variability of fatty acid (FA) composition of soft corals was examined in the tropical alcyonarian Sarcophyton sp., tropical gorgonian Euplexaura erecta, and boreal alcyonarian Gersemia rubiformis. Characteristic significant differences in the FA composition were found between these species belonging to different taxonomic groups and habitats. We assume that the FA groups 14: 0 + 16: 0 + 18: 3n-6, 16: 2 + 20: 4n-6 + 24: 5n-6, and 18: 1n-7 + 20: 1n-7 + 20: 5n-3 + 24: 6n-3 are characteristic of Sarcophyton sp., E. erecta, and G. rubiformis respectively. There were no significant differences (p > 0.05) between the three soft coral species in the content of oleic, linoleic, and docosahexaenoic acids. The relative content of more than 45% of individual FA did not significantly differ (p > 0.05) between the pairs of species, i.e., intraspecific variations exceeded interspecific ones. The reasons for intraspecific variability of soft coral FA composition are discussed. Control of this variability is needed when using individual FA as chemotaxonomic and food markers.     

Comparative flavonoid glycoside biochemistry as a chemotaxonomic tool in the subdivision of the classical ‘genus’ Lycopodium

A wide variety of novel flavone 5-O-glucosides has been isolated from Lycopodium scariosum. The predominance of tricin derivatives in this species is not in accord with earlier proposed chemotaxonomic definitions of the sub-groups within the classical genus Lycopodium L. cernuum is the first lycopod found to contain flavone C-glycosides and its suggested taxonomic separation from other members of the group is thus substantiated. Flavonoid glycosides appear to offer more definitive chemotaxonomic characters than do the previously used aglycones and modification of the chemical definitions of the sub-groups in these terms is necessary.     

Effect of exogenous sterols on the growth and fatty acid composition of the oomycetePythium debaryanum

Exogenous ergosterol and cholesterol were found to affect the growth and lipogenesis of the oomycete fungusPythium debaryanum, which is unable to synthesize de novo steroid compounds. These sterols stimulated the growth of the fungus during its submerged cultivation in glucose-peptone medium. This was accompanied by the shortening of the lag phase, the lengthening of the period of active growth, and by a 3.7-or 4.3-fold increase in the maximum biomass in response to the addition of ergosterol or cholesterol, respectively. In the presence of ergosterol, the cellular content of polyenoic fatty acids increased, and the relative content of eicosapolyenoic fatty acids reached 31.4% of the total amount of fatty acids in cells. Conversely, cholesterol decreased the cellular content of polyenoic acids, and the relative content of eicosapolyenoic acids fell to 19.6% of the total amount of fatty acids. It may be inferred that exogenous sterols enhance the yield of pharmacologically active polyenoic acids because of the growth stimulation.     

A comparative study of cycad mucilages

The patterns of monosaccharide distribution of the mucilages of Cycadales are characteristic at the generic level. Arabinose, fucose, galactose, mannose, rhamnose and methylrhamnose were identified in the hydrolysed mucilage of Bowenia, Ceratozamia, Cycas, Dioon, Encephalartos, Lepidozamia, Macrozamia, Microcycas and Zamia. Stangeria contains no rhamnose and methylrhamnose, and Ceratozamia contains galactose only in traces. American genera may easily be distinguished from the others by means of their different monosaccharide composition. Lepidozamia appears to be well separated from Macrozamia.     

Sterols and fatty acids of the marine diatom biddulphia sinensis

Nine sterols, most showing Δ⁵- or Δ^5,22-unsaturation, were identified in the marine diatom Biddulphia sinensis. One sterol, cholesta-5,22E-dien-3β-ol, comprised 70–80% of the total sterols which is the first such predominance noted in a diatom. The only Δ⁷-sterol detected was cholest-7-en-3β-ol and this was a very minor component. A sterol showing unusual side-chain alkylation,23,24-dimethylcholesta-5,22E-dien-3β-ol, was identified for the first time in a diatom. Total fatty acids exhibited a predominance of Δ⁹- 16:1, 14:0, 20:5 and 16:0, typical of diatoms, although the proportions of these acids were found to vary with culture maturity. n-Heneicosahexaene was the major hydrocarbon together with a small amount of squalene.     

Fatty acids,sterols and hydrocarbons in the leaves from eleven species of mangrove

The fatty acid, sterol and hydrocarbon compositions of the fresh leaves from eleven species of mangroves, cultivated in a shadehouse, are reported. The fatty acid and sterol analyses, whilst generally typical of higher plants, showed several chemotaxonomically significant differences between the species. The epicuticular wax hydrocarbons and fatty acids were low in abundance compared to previous reports of mangrove leaf lipids, which may reflect the importance of environmental influences on this group of compounds. Cluster analysis of selected subsets of the data showed clear chemotaxonomic divisions amongst the mangroves. The results grouped the mangroves into genera, except for the Rhizophora and Ceriops tagal which were not separated, and grouped the family Rhizophoraceae distinct from all other species except Xylocarpus granatum. Avicennia marina var. resinifera was able to be distinguished from Avicennia marina by cluster analysis, supporting its assignment as a distinct variety. The results show that the lipids of mangroves are chemotaxonomically significant.     

Phenolic compounds of the subfamily pomoideae: A chemotaxonomic survey

The subfamily Pomoideae has been surveyed for leaf phenolics and it has been shown that flavone glycosides are present in the genera Sorbus, Aronia, Chaenomeles and Hesperomeles in addition to the previously reported occurrences in Crataegus, Malus and Pyrus. The dihydrochalcone phloridzin, a typical constituent of Malus, has also been found in Docynia. Arbutin and phenolic acid-calleryanin esters are apparently restricted to Pyrus. Naringenin and eriodictyol glucosides have been detected in Pyracantha, Sorbus, Photinia, Chaenomeles and Hesperomeles. A number of Pomoideae phenolics have been found in two Spiraeoideae genera; luteolin 7-glucoside,] luteolin 7-diglucoside, luteolin 7-rhamnosylglucoside and apigenin 7-glucoside in Exochorda and the dihydrochalcone trilobatin in Sorbaria. The chemotaxonomic evidence is consistent with the hypothesis that the Pomoideae evolved through a process of allopolyploidy from primitive members of the Spiracoideae and Prunoideae.     

Fatty acid composition and the classification of the Porifera

Investigation of the fatty acid profiles of 55 species of Porifera has confirmed the occurrence of high percentages of both long chain fatty acids (C₂₄-C₃₀) and polyunsaturated acids. These features of the fatty acid profile in conjunction with the content of branched chain acids and the dominance of particular acids in different species allow some systematic discussion. The Dictyoceratida, Clathriidae, Halichondrida, Homoscleromorpha and Calcarea are distinguished by aspects of their fatty acid profiles. The diversity in number and type of sponge fatty acids exceeds that of any other phylum. Environmentally induced variation in fatty acid content is such that percentage compositions alone have little taxonomic informational value.     

The composition and taxonomic significance of fatty acid patterns in three white rust species: <Emphasis Type="Italic">Albugo amaranthi,A. candida and A. tragopogonis</Emphasis> (Peronosporales,Albuginaceae)

The fatty acid composition of the biotrophic white rust species A. amaranthi, A. candida and A. tragopogonis was identified by means of GC and GC/MS analysis. Besides the common saturated fatty acids of C14 to C22 chain length, several unusual monounsaturated and polyunsaturated fatty acids were present in significant amounts in the lipid profiles of the three species. Each taxon revealed its own characteristic pattern which was uniform among populations of different geographic origin and independent from the host species. Fatty acids were obtained from minute amounts of sporangia collected from the surface of desiccated host plants. Comparison of herbarium specimens revealed a decrease of polyunsaturated compounds after storage for 30 months at room temperature, but still allowed unquestionable species differentiation.     

Chemotaxonomy of planktonic cyanobacteria based on non-polar and 3-hydroxy fatty acid composition

Twenty-eight axenio planktonic cyanobacterial strains (10 Microcystis, three Oscillatoria, one Spirulina, one Aphanizomenon, 13 Anabaena) were investigated for their fatty acid composition by measurement of non-polar and hydroxy fatty acids. No 2-hydroxy fatty acids were detected in any strain, but 3-hydroxy fatty acids were detected in minor quantities in 24 strains. The highest portion of total fatty acids were non-polar fatty acids. Qualitative and quantitative analyses of 3-hydroxy fatty acids showed no taxonomic value in these strains, while the type of non-polar fatty acid composition was shown to be consistent within Microcystis and Anabaena strains, distinguishing them as type 4, characterized by the presence of 18:4, and type 2, characterized by 18:3 (α) of the Kenyon-Murata system. Two Oscillatoria agardhii Gomont strains were also included in the type 2 group due to the presence of 18: 3 (α), but the difference in characteristics of 16:2 and 16:3 between O. agardhii and Anabaena further divided type 2 into two subgroups: type 2A for Anabaena and type 2B for O. agardhii. A simplified unweighted pair group method with arithmetic averages (UPGMA) dendrogram demonstrated that the classification of 28 strains (Microcystis spp., Anabaena spp., Aphanizomenon flos-aquae (Lemmermann) Ralfs f. gracile (Lemmermann) Elenkin, O. agardhii and Spirullnasubsalsa Oersted ex Gomont based on numerical analysis of non-polar fatty acids corresponded to morphological species criteria, suggesting that non-polar fatty acid composition is a valuable chemical marker in the taxonomy of planktonic cyanobacteria. However, the fatty acid composition in Oscillatoria raciborskii is similar to that of Microcystis and very different from that of O. agardhii, suggesting its special position in Oscillatoria and the chemical diversity in the genus Oscillatoria.     

Phycoerythrins as chemotaxonomic markers in red algae: A survey

A simple general procedure is described for the purification of high molecular weight phycoerythrin from red algae. Protein of purity adequate for precise spectroscopic characterization was obtained from as little as 0.2 g wet wt of fresh algal tissue. The absorption, excitation and fluorescence emission spectra of over a hundred phycoerythrins from representatives of all of the orders of the Bangiophyceae and Florideophyceae were determined. On the basis of visible absorption spectra, the phycoerythrins were subdivided into five groups: B-phycoerythrin Type I [542 > 567 > 502(s)], B-phycoerythrin Type II [566 ? 528 > 500(s)], R-phycoerythrin Type I (565 > 543 > 497), R-phycoerythrin Type II [566 > 551(s) > 496], and R-phycoerythrin Type III (567 > 539 < 496), where the numbers in parentheses specify the absorption maxima in nm and (s) denotes shoulder. Phycoerythrins do not appear to be useful at familial, ordinal and class levels in taxonomic studies. However, they do appear to be of limited value in discriminating taxonomic groupings at the generic and specific level. Audouinella (Acrochaetiales) can be separated into two groups of species, B-PE and R-PE types, but this is not correlated with cytological, morphological or life-history patterns. Rhodophysema can be removed from the Cryptonemiales and placed in the Acrochaetiales on the basis of its B-PE content, morphology and life history.     

Meconic acid as a chemotaxonomic marker in the papaveraceae

Of 48 species of Papaveraceae examined representing 12 genera, 24 were shown to contain meconic acid and of these, 21 were Papaver species. Meconopsis cambrica was also found to contain meconic acid, in contrast to other species of Meconopsis examined. One recent rearrangement of the Papaveraceae includes a grouping of Papaver, Roemeria and Stylomecon together with M. cambrica and our further discovery of meconic acid in two Roemaria species examined leads to the conclusion that meconic acid may be a distinctive taxonomic feature of this new grouping. Some attempt has also been made to correlate meconic acid occurrence with that of certain types of alkaloids, and of chelidonic acid.     

UNUSUAL DIHYDROXYSTEROLS AS CHEMOTAXONOMIC MARKERS FOR MICROALGAE FROM THE ORDER PAVLOVALES (HAPTOPHYCEAE)1

Recent studies have led to the identification of an unusual class of dihydroxysterols (steroidal diols termed “pavlovols”)in a few species of microalgae from the genus Pavlova (family Pavlovaceae, class Haptophyceae = Prymnesiophyceae). These compounds have an additional hydroxyl group at G-4 in the sterol A ring, which appears to be very rare in sterol biosynthetic pathways. The sterol compositions of many other haptophytes from different orders have been analyzed, but to date all have lacked pavlovols. We now report the occurrence of these compounds in Diacronema vlkianum Prauser and two strains of Pavlova pinguis Green. This is the first report of the lipid composition of these species. Both microalgae contained “24-methylpavlovol” (4α, 24-dimethyl-5α-cholestan-3β, 4β-diol), P. pinguis also contained “24-ethylpavlovol” (4α-methyl-24-ethyl-5α-cholestan-3β, 4β-diol), and D. vlkianum contained a diol identified from its mass spectrum as 4α, 24β-dimethyl-5α-cholest-22E-en-3β,4β-diol. Both species contained structurally analogous 4-desmethyl sterols and 4-methyl sterols, although there were major differences in the proportions in each series. The major 4-desmethyl sterol in both species was 24-ethylcholesta-5, 22E-dien-3β-ol and the major 4-methyl sterol was 4α-methyl-24-ethyl-5α-cholest-22E-en-3β-ol. The presence of pavlovols in P. pinguis, combined with earlier data, suggests that all Pavlova species might have this distinguishing lipid feature. However, their identtjication in D. vlkianum extends the occurrence of these compounds to another genus and shows that they are not unique to the genus Pavlova. However, they are probably restricted to species from the order Pavlov ales. The modes of biosynthesis and functions of pavlovols remain unknown.     

Phytochemical and chemotaxonomic study on the Lichen Lethariella cladonioides

The comprehensive phytochemical research of Lethariella cladonioides (Nyl.) Krog, (Parmeliaceae), a lichen in southwest China, resulted in isolation of eighteen compounds (1–18), including a new phenolic acid 3,5-dihydroxy-4-methylbenzaldehyde (1) and seventeen known compounds, nine phenolic acids (2–10), one dibenzofuran (11), two depsides (12 and 13), one alkane (14), one glucoside (15), two polyols (16 and 17), and one fatty acid (18). The structures of these compounds were assigned by detailed interpretations of spectroscopic data (1D and 2D NMR, HR-ESI-MS) and comparisons with the published data. Among them, 3,5-dihydroxy-4-methylbenzaldehyde (1) is a new one. (−)-hydroxypropan-2′,3′-diol-orsellinate (10) have not been reported from any species in the lichens. Compounds 6, 7, 9, 12, 14, 16 and 18 were firstly isolated from the genus Lethariella (Motyka) Krog. Compounds 2, 6, 7, 9, 10, 12, 14, 16 and 18 were reported from L. cladonioides firstly. The chemotaxonomic significance of these compounds was also discussed.