The versatility of algae and their lipid metabolism

Eukaryotic algae are a very diverse group of organisms that are key components of ecosystems ranging from deserts to the Antarctic. They account for over half of the primary production at the base of food chains. The lipids of different classes are varied and contain unusual compounds not found in other phyla. In this short review, we introduce the major cellular lipids and their fatty acids and then describe how the latter (particularly the polyunsaturated fatty acids, PUFAs) are synthesised. The discovery of different elongases and desaturases important for PUFA production is detailed and their application for biotechnology described. Finally, the potential for algae in commercial applications is discussed, particularly in relation to the production of very long chain PUFAs and biofuel.     

花色苷化学研究进展

本文以近期研究报道作为基础从花色苷的化学性质、提取与分离技术、鉴定技术三个方面对花色苷化合物的化学研究进展做一系统综述。     

The importance of high‐quality algal food sources in stream food webs – current status and future perspectives

相似文献   

Diketopiperazines from marine organisms

Diketopiperazines (DKPs), which are cyclic dipeptides, have been detected in a variety of natural resources. Recently, the interest in these compounds increased significantly because of their remarkable bioactivity. This review deals with the chemical structures, biosynthetic pathways, and biological activities of DKPs from marine microorganisms, sponges, sea stars, tunicates (ascidians), and red algae. The literature has been covered up to December 2008, and a total 124 DKPs from 104 publications have been discussed and reviewed. Some of these compounds have been found to possess various bioactivities including cytotoxicity, and antibacterial, antifungal, antifouling, plant-growth regulatory, and other activities.     

赤潮过程中“藻-菌”关系研究进展

微生物对促进海洋物质循环,维持水生环境的生态平衡具有重要作用。在赤潮事件中,基于微生物(尤其是细菌)的多样性和重要性,它们与藻类之间的相互关系成为了研究的热点。过去20年里,人们从不同角度对"藻-菌"间的关系进行了探索,包括物理学过程、生物学过程、环境过程以及化学过程。就化学过程而言,它作为一种较早出现的技术,在以往的研究中带给人们许多认识藻菌关系的方法。随着学科的渗透,化学法有了拓展与延伸,为人们认识藻菌关系带来了新的契机。从化学生态学领域来梳理"藻-菌"关系中涉及的现象和行为,包括菌对藻的有益面、菌对藻的有害面、以及藻类应答细菌行为的化学途径;并从信号语言(群体感应、化感作用)的角度来阐释两者之间的互生或克生关系。通过文献综述的方式来解读藻菌关系的互作过程和机理,为认识赤潮的发生和防控方法提供借鉴。     

Marine macroalgae and their associated microbiomes as a source of antimicrobial chemical diversity

ABSTRACT

This article reviews the role of microbial biofilms in infection, and the antimicrobial chemical diversity of marine macroalgae and their associated microbiomes. Antimicrobial resistance (AMR) represents one of the major health threats faced by humanity over the next few years. To prevent a global epidemic of antimicrobial-resistant infections, the discovery of new antimicrobials and antibiotics, better anti-infection strategies and diagnostics, and changes to our current use of antibiotics have all become of paramount importance. Numerous studies investigating the bioactivities of seaweed extracts as well as their secondary and primary metabolites highlight the vast biochemical diversity of seaweeds, with new modes of action making them ideal sources for the discovery of novel antimicrobial bioactive compounds of pharmaceutical interest. In recent years, researchers have focused on characterizing the endophytic and epiphytic microbiomes of various algal species in an attempt to elucidate host-microbe interactions as well as to understand the function of microbial communities. Although environmental and host-associated factors crucially shape microbial composition, microbial mutualistic and obligate symbionts are often found to play a fundamental role in regulating many aspects of host fitness involving ecophysiology and metabolism. In particular, algal ‘core’ epiphytic bacterial communities play an important role in the protection of surfaces from biofouling, pathogens and grazers through the production of bioactive metabolites. Together, marine macroalgae and their associated microbiomes represent unique biological systems offering great potential for the isolation and identification of novel compounds and strategies to counteract the rise and dissemination of AMR.     

Climate change and disease: bleaching of a chemically defended seaweed

Disease is emerging as an important impact of global climate change, due to the effects of environmental change on host organisms and their pathogens. Climate‐mediated disease can have severe consequences in natural systems, particularly when ecosystem engineers, such as habitat‐formers or top predators are affected, as any impacts can cascade throughout entire food webs. In temperate marine ecosystems, seaweeds are the dominant habitat‐formers on rocky reefs. We investigated a putative bleaching disease affecting Delisea pulchra, a chemically defended seaweed that occurs within a global warming ‘hot‐spot’ and assessed how patterns of this phenomenon were influenced by ocean temperature, solar radiation, algal chemical defences and microbial pathogens. Warmer waters were consistently and positively correlated with higher frequencies of bleaching in seaweed populations, but patterns of bleaching were not consistently influenced by light levels. Bleached thalli had low levels of antibacterial chemical defences relative to healthy conspecifics and this was observed across entire thalli of partially bleached algae. Microbial communities associated with bleached algae were distinct from those on the surfaces of healthy seaweeds. Direct testing of the importance of algal chemical defences, done here for the first time in the field, demonstrated that they protected the seaweed from bleaching. Treatment of algal thalli with antibiotics reduced the severity of bleaching in experimental algae, especially at high water temperatures. These results indicate that bleaching in D. pulchra is the result of temperature‐mediated bacterial infections and highlight the potential for warming to influence disease dynamics by stressing hosts. Understanding the complex ways in which global change may affect important organisms such as habitat‐forming seaweeds, is essential for the management and conservation of natural resources.     

Microorganisms living on macroalgae: diversity,interactions, and biotechnological applications

Marine microorganisms play key roles in every marine ecological process, hence the growing interest in studying their populations and functions. Microbial communities on algae remain underexplored, however, despite their huge biodiversity and the fact that they differ markedly from those living freely in seawater. The study of this microbiota and of its relationships with algal hosts should provide crucial information for ecological investigations on algae and aquatic ecosystems. Furthermore, because these microorganisms interact with algae in multiple, complex ways, they constitute an interesting source of novel bioactive compounds with biotechnological potential, such as dehalogenases, antimicrobials, and alga-specific polysaccharidases (e.g., agarases, carrageenases, and alginate lyases). Here, to demonstrate the huge potential of alga-associated organisms and their metabolites in developing future biotechnological applications, we first describe the immense diversity and density of these microbial biofilms. We further describe their complex interactions with algae, leading to the production of specific bioactive compounds and hydrolytic enzymes of biotechnological interest. We end with a glance at their potential use in medical and industrial applications.     

Effects of essential fatty acids and N and P-limited algae on the growth rate of tropical cladocerans

SUMMARY 1. In this study, the effects of nutrient (N and P) deficiency and the importance of essential polyunsaturated fatty acids (PUFA) [eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)] to tropical cladocerans, growth and reproduction were determined in a growth bioassay.
2. The animals were fed N/P-sufficient, N-deficient and P-deficient algae, and also N and P-deficient algae supplemented with fish oil emulsions rich in EPA and DHA.
3. Cladocerans showed different responses to nutrient-deficient algae and also to supplements of fish oil emulsions. Moina micrura was most sensitive to P-deficient alga and, surprisingly, grew better and produced more eggs in N-deficient alga than in N/P sufficient alga. Ceriodaphnia cornuta was less sensitive, growing well in both N and P-deficient algae. This species, however, had a lower clutch size in N-deficient alga. On the other hand, Daphnia gessneri was the most sensitive to mineral limitation, showing decreased growth and clutch size in both nutrient-deficient algae.
4. The PUFA supplements to nutrient-deficient algae increased growth rates only for M. micrura and C. cornuta , suggesting that these fatty acids are important food requirements for these species.     

Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N-oleoylethanolamine analogues

The synthesis of novel N-acylethanolamines and their use as inhibitors of the aCDase is reported here. The compounds are either 2-oxooctanamides or oleamides of sphingosine analogs featuring a 3-hydroxy-4,5-hexadecenyl tail replaced by ether or thioether moieties. It appears that, within the 2-oxooctanamide family, the C3-OH group of the sphingosine molecule is required for inhibition both in vitro and in cultured cells. Furthermore, although the (E)-4 double bond is not essential for inhibitory activity, the (E) configuration is required, since the analogue with a (Z)-4 unsaturation was not inhibitory. None of the oleamides inhibited the aCDase in vitro. Conversely, with the exception of N-oleoylethanolamine and its analogs with S-decyl and S-hexadecyl substituents, all the synthesized oleamides inhibited the aCDase in cultured cells, although with a relatively low potency. We conclude that novel aCDase inhibitors can evolve from N-acylation of sphingoid bases with electron deficient-acyl groups. In contrast, chemical modification of the N-oleoylsphingosine backbone does not seem to offer an appropriate strategy to obtain aCDase inhibitors.     

Lipid domains in bacterial membranes and the action of antimicrobial agents

There has been increasing interest in recent years in describing the lateral organization of membranes and the formation of membrane domains. Much of the focus in this area has been on the formation of cholesterol-rich domains in mammalian membranes. However, it is likely that there are domains in all biological membranes. One of the challenges has been to define the chemical composition, lifetime and size of these domains. There is evidence that bacteria have domains that are enriched in cardiolipin. In addition, the formation of lipid domains can be induced in bacteria by clustering negatively charged lipids with polycationic substances. Many antimicrobial compounds have multiple positive charges. Such polycationic compounds can sequester anionic lipids to induce lipid phase separation. The molecular interactions among lipids and their lateral packing density will be different in a domain from its environment. This will lead to phase boundary defects that will lower the permeability barrier between the cell and its surroundings. The formation of these clusters of anionic lipids may also alter the stability or composition of existing membrane domains that may affect bacterial function. Interestingly many antimicrobial agents are polycationic and therefore likely have some effect in promoting lipid phase segregation between anionic and zwitterionic lipids. However, this mechanism is expected to be most important for substances with sequential positive charges contained within a flexible molecule that can adapt to the arrangement of charged groups on the surface of the bacterial cell. When this mechanism is dominant it can allow the prediction of the bacterial species that will be most affected by the agent as a consequence of the nature of the lipid composition of the bacterial membrane.     

寄生隐丛赤壳菌Cryphonectria parasitica致病毒素Cp-I的分离纯化和结构分析

寄生隐丛赤壳菌Cryphonectria parasitica菌株经液体培养,石油醚萃取其发酵液获得对板栗带叶嫩枝具有致萎活性的粗提物,以氯仿:石油醚:甲醇(6:2:2)作洗脱剂,粗提物经硅胶色谱分离,共得到3组纯组份,其中第1组份(Cp-I)对板栗幼苗致萎活性较高.质谱、核磁共振和红外光谱测定表明Cp-I分子量为278,化学式为C<,16>H<,22>O<,4>.     

Development of microsatellites DNA markers in the cultivated seaweed,Gracilaria chilensis (Gracilariales,Rhodophyta)

The red algae Gracilaria chilensis is extensively cultivated for agar production. In spite of its commercial significance as the first algal resource in Chile, no information is available on the pattern of genetic diversity. In this paper, we isolated six polymorphic microsatellite markers from a G. chilensis‐enriched DNA library. Genetic diversity was assessed in two natural populations revealing relatively low levels of heterozygosity ranging from 0.00 to 0.51. The six loci developed here are good candidates to assess the level of genetic resources within this species, which probably suffered from over‐exploitation in several localities along the Chilean coast.     

寄生隐丛赤壳菌致病毒素Cp-I的分离纯化和结构分析

寄生隐丛赤壳菌Cryphonectria parasitica菌株经液体培养,石油醚萃取其发酵液获得对板栗带叶嫩枝具有致萎活性的粗提物,以氯仿:石油醚:甲醇(6:2:2)作洗脱剂,粗提物经硅胶色谱分离,共得到3组纯组份,其中第1组份(Cp-I)对板栗幼苗致萎活性较高。质谱、核磁共振和红外光谱测定表明Cp-I分子量为278,化学式为C16H22O4。     

An Edge Selection Mechanism for Chirally Selective Solubilization of Binaphthyl Atropisomeric Guests by Cholate and Deoxycholate Micelles

Combining micellar electrokinetic capillary chromatography (MEKC) and nuclear magnetic resonance (NMR) experimentation, we shed light on the structural basis for the chirally selective solubilization of atropisomeric binaphthyl compounds by bile salt micelles comprised of cholate (NaC) or deoxycholate (NaDC). The model binaphthyl analyte R,S‐BNDHP exhibits chirally selective interactions with primary micellar aggregates of cholate and deoxycholate, as does the closely related analyte binaphthol (R,S‐BN). Chiral selectivity was localized, by NMR chemical shift analysis, to the proton at the C12 position of these bile acids. Correspondingly, MEKC results show that the 12α‐OH group of either NaC or NaDC is necessary for chirally selective resolution of these model binaphthyl analytes by bile micelles, and the S isomer is more highly retained by the micelles. With NMR, the chemical shift of 12β‐H was perturbed more strongly in the presence of S‐BNDHP than R‐BNDHP. Intermolecular NOEs demonstrate that R,S‐BNDHP and R,S‐BN interact with a similar hydrophobic planar pocket lined with the methyl groups of the bile salts, and are best explained by the existence of an antiparallel dimeric unit of bile salts. Finally, chemical shift data and intermolecular NOEs support different interactions of the enantiomers with the edges of dimeric bile units, indicating that R,S‐BNDHP enantiomers sample the same binding site preferentially from opposite edges of the dimeric bile unit. Chirality 28:525–533, 2016. © 2016 Wiley Periodicals, Inc.     

Scraping a living: a review of littorinid grazing

Littorinid snails are predominantly herbivorous and the versatility of their radulae enables them to feed on a variety of macroscopic and microscopic plants in a diversity of habitats. Some are selective feeders preferring some species of algae to others, and rejecting some even after a prolonged period of starvation. Different species of snail exhibit different preferences. The factors affecting the attractiveness and edibility of food plants are discussed and food value considered.Foraging behaviour of littorinids is briefly reviewed in relation to the influence of chemical cues from the algae. Littorinids appear to be able to select or reject algae without having ingested them, having perceived the plants from a distance, moving towards favoured foods (or habitat-providing plants) and away from those that it rejects. The nature of the chemical cues emitted by the algae is discussed. Temporal patterns of foraging activity show some evidence of an endogenous component which can be overridden by responses to environmental conditions. These patterns place restraints on energy intake.The structural and chemical defences used by algae against littorinid grazing are considered. The importance of polyphenolic compounds is evaluated. The effects of grazing as a selective agency and a factor influencing algal populations are discussed. There is some evidence that life history patterns are a response to grazing. The influence of external physical factors, such as salinity on grazing pressure is demonstrated.Finally, the impact of littorinid snails on intertidal communities is assessed in relation to their abundance and biogeographical distribution. The relative importance of littorinids is contrasted on shores possessing or lacking limpets.     

A study of the interactions among adenosine triphosphate, epinephrine, and magnesium ions

The interactions among adenosine triphosphate, Mg⁺², and epinephrine at pH's below 7.0 have been studied by observing the effects of these interactions on the chemical shifts and line widths of their ¹H and ³¹P nuclear magnetic resonance spectra. Mg⁺² is tightly bound by the β- and γ-phosphate groups of adenosine triphosphate and there is a weak association between this chelate and epinephrine. In the ternary complex, the aromatic ring of epinephrine overlaps the purine ring of adenosine triphosphate and there appears to be an ionic interaction between the protonated amino group and the α-phosphate of adenosine triphosphate. It was also found that dichloroisoproterenol forms essentially the same type of ternary complex.     

UNIVERSAL PRIMERS AMPLIFY A 23S rDNA PLASTID MARKER IN EUKARYOTIC ALGAE AND CYANOBACTERIA1

The challenge in the development of universal algal primers lies in the genetic diversity contained within the vast array of evolutionary lineages present in this informally named group of organisms. A comparative genomics approach was used previously to identify conserved primers flanking a region of the plastid genome. Our present research illustrates the feasibility of amplifying and sequencing this marker across multiple algal lineages. We present a preliminary framework of 107 novel sequences of this region from 62 red algae, 19 green algae, 14 brown algae, 8 cyanobacteria, 2 diatoms, 1 xanthophyte, and 1 euglenoid, and illustrate levels of divergence of the marker for well‐represented groups in a neighbor‐joining analysis. This ～410 nt region distinguishes most species included in the analysis. The remarkable universality of these primers suggests potential for their use in assays of environmental samples in which they could be used to simultaneously detect a number of different algal lineages.     

HIGH POLYUNSATURATED FATTY ACID LEVELS IN TWO SUBTROPICAL MACROALGAE,CLADOSIPHON OKAMURANUS AND CAULERPA LENTILLIFERA1

The lipid and fatty acid compositions in two edible subtropical algae (the brown alga Cladosiphon okamuranus Tokida and the green alga Caulerpa lentillifera J. Agardh) were determined to clarify their lipid characteristics and nutritional values. Glycolipids and phospholipids were the major lipid classes, with significant levels of triacylglycerols. Polyunsaturated fatty acids (PUFA) were the major fatty acids of both algae. The lipid class composition and major fatty acids were similar in both the algal species, irrespective of wild and cultured specimens. Typical n‐6 PUFA, such as 18:2n‐6 (linoleic acid) and 20:4n‐6 (arachidonic acid), occurred in characteristically high levels in both of the algae. High levels of n‐3 PUFA were measured in all lipid classes of both species without 22:6n‐3 (docosahexaenoic acid), 18:3n‐3, 18:4n‐3, and 20:5n‐3 (eicosapentaenoic acid) for Cl. okamuranus; and 16:3n‐3, 18:3n‐3, and 20:5n‐3 for Ca. lentillifera. The finding suggests that the green algal species, which mainly biosynthesizes short‐chain (C₁₆ and C₁₈) PUFA, differs from that of the brown alga, which is capable of biosynthesizing high 20:5n‐3 levels. The PUFA levels in glycolipids of the two algal species comprised up to 60%, even though they are subtropical marine species. High n‐6 PUFA levels in the algal lipids probably influence the significant levels of n‐6 PUFA in herbivorous fishes, because the n‐6 PUFA levels in marine fish lipids are generally undetectable or negligible.