Evidence contrary to the existence of storage lipid in leaves of plants inhabiting cold climates

Abstract In a study of the lipid composition of the upland Empetrum nigrum subspp. hermaphroditum and Empetrum nigrum subspp. nigrum with a lowland distribution, no evidence was found to support the suggestion that lipids (triacylglycerols) play a major energy storage role in the leaves of alpine species. On a quantitative basis the triacylglycerols constituted less than 5% of the total lipid in both species and the lowland species possessed the higher levels of total lipid, neutral lipid and triacylglycerols. It is suggested that the presence of a well-developed waxy cuticle might account for the high total lipid levels encountered in dwarf evergreen shrubs.     

Fatty acids of sponges from the Sea of Okhotsk

The fatty acid (FA) composition of Demospongiae species from the Sea of Okhotsk was studied. Fifteen sponge species were investigated for the first time, and the previously studied species Desmacella rosea and Myxilla incrustans were reexamined for their FA composition. Gas chromatography-mass spectrometry revealed 150 different fatty acids, of which 15 have not been identified in sponge lipids previously. The relative content of saturated FAs varied from 7.6 in Melonachora kobjakovae to 29.6% in Amphilectus digitata, with an average of 14.6% of total FAs. The relative content of monoenic FAs ranged from 12.8 in T. dirhaphis to 27.0% in Polymastia sp., with an average of 20.6% of total FAs. Non-methylen-interrupted, primarily unsaturated Δ5,9-FAs contributed a significantly to the amount of polyunsaturated fatty acids of sponges; this being a distinguishing feature of the FA composition of the investigated group of organisms.     

昆虫功能性脂质与油脂的开发

昆虫脂质无论在量上还是在质上都有其可资研究和利用的特点,昆虫功能性脂质和油脂的开发具有广阔的前景。     

Identification of (all-cis)-6,9,12,15-octadecatetraenoic acid in Ribes nigrum and fish oils: chemical and physical characterization.

In this report, we show that the non-conjugated octadecatetraenoic acid found in the oil of the seeds from Ribes nigrum is identical to the C₁₈-polyunsaturated fatty acid previously isolated in a number of fish oils and seed oils. Evidence obtained from mass spectral data of its triazolopyridine derivative clearly indicates the presence of methylene-interrupted double bonds. Comparison with authentic material prepared by chemical synthesis provides further confirmation of the (all-cis)-6,9,12,15-octadecatetraenoic acid structure. The (all-cis)-4,8,12,15-structural arrangement erroneously attributed to this acid in several literature reports is thus definitely ruled out.     

微生物油脂及其生产工艺的研究进展

微生物油脂是一种应用前景广阔的新型油脂资源,正越来越受到人们的重视,尤其在生产富含不饱和脂肪酸的功能性油脂方面已成为研究热点。该文对微生物油脂的特点及组成、产油微生物必备条件及常见种类、微生物油脂的生产工艺等方面进行了综述,展望了其研究的发展前景。     

Fatty acids from oleaginous yeasts and yeast-like fungi and their potential applications

Purpose: Oleaginous yeasts, fatty acids biosynthesis and regulation in the oleaginous yeasts and the fatty acids from the oleaginous yeasts and their applications are reviewed in this article.

Results: Oleaginous yeasts such as Rhodosporidium toruloides, Yarrowia lipolytica, Rhodotorula mucilaginosa, and Aureobasidium melanogenum, which can accumulate over 50% lipid of their cell dry weight, have many advantages over other oleaginous microorganisms. The fatty acids from the oleaginous yeasts have many potential applications. Many oleaginous yeasts have now been genetically modified to over-produce fatty acids and their derivatives. The most important features of the oleaginous yeasts are that they have special enzymatic systems for enhanced biosynthesis and regulation of fatty acids in their lipid particles. Recently, some oleaginous yeasts such as R. toruloides have been found to have a unique fatty acids synthetase and other oleaginous yeasts such as A. melanogenum have a unique highly reducing polyketide synthase (HR-PKS) involved in the biosynthesis of hydroxyl fatty acids.

Conclusions: It is necessary to further enhance lipid biosynthesis using metabolic engineering and explore new applications of fatty acids in biotechnology.     

Localization of lipids containing (Z)-11-eicosenoic acid and (Z)-13-docosenoic acid in Tropaeolum majus

(Z)-11-Eicosenoic (gondoic) and (Z)-13-docosenoic (erucic) acids were found in large proportions as constituent fatty acids of the triglycerides and polar lipids in seeds and petals of Tropaeolum majus. In the lipids of the other floral organs as well as in those of vegetative organs, only traces of these fatty acids were detected. During seed germination, the proportions of the two fatty acids did not change. (Z)-9,12- Octadecadienoic (linoleic) and (Z)-9,12,15-octadecatrienoic (linolenic) acids, which occurred only in traces in lipids of the seeds, were major constituent fatty acids of lipids in floral and vegetative organs as well as those of callus cultures.     

Fuel oils from euphorbs and other plants

Fuel oils from Euphorbs and other plants. The increasing energy costs of finding petroleum, together with the sure knowledge that its supply is finite, has prompted us to seek other sources of liquid hydrocarbon for both fuel and material. We have turned to annually renewable plant sources such as seed oils, an obvious source, with palm oil as the most productive. Sugar cane used to produce ethanol is another fuel source already in use.
We have examined non-food plants which can be grown on marginal soil for their productivity, particularly the genus Euphorbia. All species of this genus produce a latex which can be converted into useful fuel and other material, including precursors for what might be a valuable anti-tumor agent. Euphorbias and other similar plants require repeated planting and harvesting of the entire plant, which constitutes a drain on the soil. Trees can be long-term sources for hydrocarbon-like materials with a single planting. Examples are: the genus Copaifera which can be tapped for sesquiterpenes, the genus Pittosporum which bears fruits rich in terpenes and can be harvested annually. Finally, there are algae whose oil productivity is already of interest.
It seems possible to modify genetically the terpene biosynthetic pathways in plants to improve both the quality and quantity of the oils produced from them.     

Lipase-catalyzed esterification of glycerol and polyunsaturated fatty acids from fish and microalgae oils

This paper reports on the synthesis of triglycerides by enzymatic esterification of polyunsaturated fatty acids (PUFA) with glycerol. The lipase Novozym 435 (Novo Nordisk, A/S) from Candida antarctica was used to catalyze this reaction. The main factors influencing the degree of esterification and triglyceride yield were the amount of enzyme, water content, temperature and glycerol/fatty acid ratio. The optimum reaction conditions were established as: 100 mg of lipase; 9 ml hexane; 50°C; glycerol/PUFA concentrate molar ratio 1.2:3; 0% initial water; 1 g molecular sieves added at the start of reaction; and an agitation rate of 200 rpm. Under these conditions, a triglyceride yield of 93.5% was obtained from cod liver oil PUFA concentrate; the product contained 25.7% eicosapentaenoic acid and 44.7% docosahexaenoic acid. These optimized conditions were used to study esterification from a PUFA concentrate of the microalgae Phaeodactylum tricornutum and Porphyridium cruentum. With the first, a triglyceride yield of 96.5%, without monoglycerides and very few diglycerides, was obtained after 72 h of reaction; the resulting triglycerides had 42.5% eicosapentaenoic acid. A triglyceride yield of 89.3% was obtained from a P. cruentum PUFA concentrate at 96 h of reaction, which contained 43.4% arachidonic acid and 45.6% EPA. These high triglyceride yields were also achieved when the esterification reaction was scaled up 5-fold.     

Metabolic effects of intravenous LCT or MCT/LCT lipid emulsions in preterm infants

Most lipid emulsions for parenteral feeding of premature infants are based on long-chain triacylglycerols (LCTs), but inclusion of medium-chain triacylglycerols (MCTs) might provide a more readily oxidizable energy source. The influence of these emulsions on fatty acid composition and metabolism was studied in 12 premature neonates, who were randomly assigned to an LCT emulsion (control) or an emulsion with a mixture of MCT and LCT (1:1). On study day 7, all infants received [13C]linoleic (LA) and [13C]alpha-linolenic acid (ALA) tracers orally. Plasma phospholipid (PL) and triacylglycerol (TG) fatty acid composition and 13C enrichments of plasma PL fatty acids were determined on day 8. After 8 days of lipid infusion, plasma TGs in the MCT/LCT group had higher contents of C8:0 (0.50 +/- 0.60% vs. 0.10 +/- 0.12%; means +/- SD) and C10:0 (0.66 +/- 0.51% vs. 0.15 +/- 0.17%) than controls. LA content of plasma PLs was slightly lower in the MCT/LCT group (16.47 +/- 1.16% vs. 18.57 +/- 2.09%), whereas long-chain polyunsaturated derivatives (LC-PUFAs) of LA and ALA tended to be higher. The tracer distributions between precursors and products (LC-PUFAs) were not significantly different between groups. Both lipid emulsions achieve similar plasma essential fatty acid (EFA) contents and similar proportional conversion of EFAs to LC-PUFAs. The MCT/LCT emulsion seems to protect EFAs and LC-PUFAs from beta-oxidation.     

Identification of (all-cis)-6,9,12,15-octadecatetraenoic acid in Ribes nigrum and fish oils: chemical and physical characterization

In this report, we show that the non-conjugated octadecatetraenoic acid found in the oil of the seeds from Ribes nigrum is identical to the C₁₈-polyunsaturated fatty acid previously isolated in a number of fish oils and seed oils. Evidence obtained from mass spectral data of its triazolopyridine derivative clearly indicates the presence of methylene-interrupted double bonds. Comparison with authentic material prepared by chemical synthesis provides further confirmation of the (all-cis)-6,9,12,15-octadecatetraenoic acid structure. The (all-cis)-4,8,12,15-structural arrangement erroneously attributed to this acid in several literature reports is thus definitely ruled out.     

Characterization of triacylglycerols from overwintering prepupae of the alfalfa pollinator Megachile rotundata (Hymenoptera: Megachilidae)

Alfalfa leafcutting bees, Megachile rotundata (F.), overwinter as prepupae. The internal lipids were extracted from prepupae that had been wintered at 4 degrees C for 7 months. Megachile rotundata prepupae possessed copious quantities of internal lipids (20% of the fresh weight) that were extracted with CHCl3/methanol (2:1). Transmission electron microscopy revealed that lipids were stored within very large intracellular vacuoles. Separation by silica chromatography revealed that 88% of the internal lipids were triacylglycerols. Ester derivatives of fatty acids from triacylglycerol components were analyzed by gas chromatography-mass spectrometry and 15 fatty acid constituents were identified. The majority (76%) of the triacylglycerol fatty acids were unsaturated fatty acids. The major triacylglycerol fatty acid constituent (30%) was the C16 monounsaturated fatty acid, palmitoleic acid (16:1, hexadec-9-enoic acid), with substantial amounts of linolenic acid (18:3, octadec-9,12,15-trienoic acid, 15%), palmitic acid (16:0, hexadecanoic acid, 14%) and oleic acid (18:1, octadec-9-enoic acid, 13%). Palmitoleic acid as the major fatty acid of an insect is an unusual occurrence as well as the presence of the 16-carbon polyunsaturated fatty acids, 16:2 and 16:3. The major intact triacylglycerol components were separated and identified by high performance liquid chromatography-mass spectrometry. A complex mixture of approximately 40 triacylglycerol components were identified and major components included palmitoyl palmitoleoyl oleoyl glycerol, palmitoyl palmitoleoyl palmitoleoyl glycerol, myristoyl palmitoleoyl palmitoleoyl glycerol, myristoleoyl palmitoyl palmitoleoyl glycerol, and palmitoyl palmitoleoyl linolenoyl glycerol. The function of these internal lipids and their relevance to winter survival and post-wintering development of M. rotundata is discussed.     

Essential oils from micropropagated plants of Lavandula viridis

The essential oils of Lavandula viridis were analysed by GC and GC-MS. Comparisons were made between three types of plant material from the same clone: field-grown plant, in vitro shoot cultures and micropropagated plants of the same clone. The most common components usually found in lavender oils were present in the oil samples analysed and more than 45 constituents were identified, representing more than 80% of the essential oil. The essential oils analysed consisted mainly of monoterpenes (75.4-76.3%), where oxygenated and hydrocarbons identified ranged from 41.8 to 57.3% and 18.1 to 34.2%, respectively. The major components found were 1.8-cineole (18.2-25.1%), camphor (9.1-15.7%), alpha-pinene (8.8-14.1%), borneol (4.1-4.8%), beta-pinene (1.2-5.6%), delta 3-carene (1.0-6.5%) and alpha-terpineol (0.8-4.2%). The monoterpene fraction of the in vitro shoot cultures showed different relative amounts of hydrocarbons and oxygenated components in relation to the parent plant and to micropropagated plants. In the sesquiterpene hydrocarbon fraction of the oil samples analysed (6.1-8.2%), 7-epi-alpha-selinene (1.6-4.8%) was the most important component and the oxygenated sesquiterpenes were found in small amounts (1.1-1.7%). The essential oils from field-grown plants of L. viridis, when compared with those obtained from in vitro shoot cultures or micropropagated plants of the same clone, demonstrated that the same major components were found without significant compositional variations.     

Preparation of fatty acid methyl esters for gas-liquid chromatography

A convenient method using commercial aqueous concentrated HCl (conc. HCl; 35%, w/w) as an acid catalyst was developed for preparation of fatty acid methyl esters (FAMEs) from sterol esters, triacylglycerols, phospholipids, and FFAs for gas-liquid chromatography (GC). An 8% (w/v) solution of HCl in methanol/water (85:15, v/v) was prepared by diluting 9.7 ml of conc. HCl with 41.5 ml of methanol. Toluene (0.2 ml), methanol (1.5 ml), and the 8% HCl solution (0.3 ml) were added sequentially to the lipid sample. The final HCl concentration was 1.2% (w/v). This solution (2 ml) was incubated at 45°C overnight or heated at 100°C for 1–1.5 h. The amount of FFA formed in the presence of water derived from conc. HCl was estimated to be <1.4%. The yields of FAMEs were >96% for the above lipid classes and were the same as or better than those obtained by saponification/methylation or by acid-catalyzed methanolysis/methylation using commercial anhydrous HCl/methanol. The method developed here could be successfully applied to fatty acid analysis of various lipid samples, including fish oils, vegetable oils, and blood lipids by GC.     

Fish oils and aggression or hostility

Fish oils have long been known to protect the heart from ischemic heart disease and fatal arrhythmia. Recently they have also been suggested to protect the heart in a literal sense! Although not all reports on fish oils and psychiatric disorder support the latter notion, many of them claim that fish oils were effective. The point is that, different from currently prescribed psychiatric medicines, fish oils do not do harm to any part of the body. We have been working on the effects of fish oils on aggressive behavior and hostility. Unfortunately this area of research is not mature yet. The number of related papers is rather limited, so we will take aggression and/or hostility in a broader sense including oppositional behavior, violence etc. in this review. We found fourteen intervention studies checking the effects of fish oils on aggressive behavior. Eleven of them showed the aggression/hostility-controlling effects of fish oils one way or another. We did not try to summarize those effects by meta-analysis, because we thought that the methods of research were too heterogeneous. The mechanisms as to how fish oils affect aggression/hostility is not clear yet, but several possible mechanisms have been postulated. Among them, activation of the serotonergic neuron system is the most promising. The research area of fish oils and aggression/hostility is clearly important from the medical and social points of view.     

Molecular breeding strategies for the modification of lipid composition

Summary Lipids are key components of all living cells. Acyl lipids and sterols provide the matrix of the biological membranes that both define the boundaries of cells and organelles, and act as sites for the trafficking of molecules within and into/out of cells. Lipids are also important metabolic intermediates and the most efficient form of energy storage that is available to a cell. It is the latter, energy-storing function that is of most relevance to this review. Storage lipids are accumulated in abundance in many of our most important crops, including maize, soybean, rapeseed, and oil palm, giving rise to a commerical sector valued at over $50 billion/year. Because the storage lipids of the major global oil crops have a relatively restricted composition, there is great interest in using all available breeding technologies, whether traditional or modern, to enhance the variation in lipid quality in existing crops and/or to domesticate new crops that already accumulate useful novel lipids. Over the past few decades, there has been a great deal of effort to manipulate fatty acid composition in order to produce novel lipids, especially for industrial applications. However, these attempts, many based on genetic engineering, have met with only limited commercial success-to date. More recently, there has been a resurgence of interest in the modification of both acyl and non-acyl lipids to enhance the nutritional quality of plant oils. In this review, we will examine the background to plant lipid modification and some of the latest developments, with a particular focus on edible oils.     

Lipids from the floral glands of Krameria

Gland extracts from the flowers of seven South American species of Krameria have been shown to contain free 3-acetoxy fatty acids of the same type as previously found in species from North America.     

Antibacterial activity and mechanism of essential oils in combination with medium-chain fatty acids against predominant bovine mastitis pathogens

Bovine mastitis has become a significant economic importance for the dairy industry. Concerns regarding poor milk quality and emergence of bacterial resistance have necessitated to develop an alternative therapeutic approach to antibiotics for the treatment of mastitis. Saturated medium-chain fatty acids (MCFAs) and essential oils (EOs) are known natural antimicrobials, but their combined effect has not been investigated extensively. The objective of the present investigation was to examine the bactericidal effect of various combined treatments of eight EOs and three saturated MCFAs to inactivate predominant mastitis pathogens, including Staphylococcus aureus ATCC 29213; Escherichia coli ATCC 25922; Klebsiella pneumoniae ATCC 27736 and Streptococcus agalactiae ATCC 27956. The minimum inhibitory concentration (MIC) values confirmed that all the tested pathogens were variably susceptible to both EOs and saturated MCFAs. Among essential oils, carvacrol (CAR), trans-cinnamaldehyde (TC) and thymol (TM) showed the highest inhibitory activity at concentration 0·38–1·32 mg/mL. Carvacrol exhibited effective additive antibacterial activity in combined treatment with octanoic acid (OA) in terms of its fractional inhibitory index (0·63–0·88) and time-kill effect in reducing about 6 log CFU/mL bacterial cells in less than 5 min. The effort was also made to elucidate the mechanism of antibacterial action of CAR and OA against selected mastitis pathogens by observing changes in cell microstructure, permeability and integrity of cell membrane and their membrane potential. After adding CAR and OA at MIC level, there were obvious changes in cell morphology, leakage of small electrolytes and macromolecules at the initial few hours of treatment i.e. within 1–2 h were observed. Our results indicated that CAR and OA could be evaluated as alternatives or adjuncts to antibiotics as intramammary infusion or topical application to treat bovine mastitis, significantly improving the microbiological safety of milk.     

Lipids from the glandular trichome of ailanthus altissima

The secretion from the glandular trichomes of Ailanthus altissima was found to contain bound lipid (mainly monogalactosyldiacylglycerol) as well as oleic, palmitic and linoleic acids in the free state.     

Distribution of unusual fatty acids in the triacylglycerols of sea buckthorn mesocarp oil

The structure of unusual fatty acid (FA) components of triacylglycerols (TAGs) of mature sea buckthorn (Hippophae rhamnoides L.) mesocarp oil was determined by GLC and MS, and the positional-species composition (PSC) of these TAGs was estimated using the methods of TAG chemical deacylation, TLC, GLC, and computer calculation. It was shown that the unusual FAs comprised n-cis-Δ9-hexadecenoic, n-cis-Δ9,12-hexadecadienoic (palmitolinoleic), and n-cis-Δ11-octadecenoic (cis-vaccenic) acids. The hexadecenoic acid predominated in the oil, and in its distribution in TAGs, it was similar to the total FAs differing from them only in some prevalence in the triunsaturated TAGs and in the TAGs with a shorter acyl chain, as well as in the sn-2 position of TAGs. Palmitolinoleic (16:2) acid comprised only 5% of total FAs, and it was exclusively concentrated in the sn-2 position of TAGs. As regards its distribution between various positional types and forms of TAGs, the 16:2 acid was similar to oleate and total FAs. As compared to the total TAGs, the TAGs with 16:2 acid were characterized by a lower FA chain length as well as by a highest unsaturation. The TAGs with vaccenic acid (V-TAGs) considerably exceeded O-TAGs, i.e., the TAGs containing oleic acid, another 18:1 positional isomer, both in their content in the total TAGs and in their unsaturation. In the composition of positional types and fractions of various unsaturation, O-TAGs were similar to the total TAGs, while V-TAGs were characterized by a very unusual structure, viz., a very high triunsaturated TAG level and an extremely low concentration of 1,3-disaturated-2-monounsaturated TAGs. In addition, oleic acid, like most other unsaturated FAs, was incorporated predominantly in the sn-2 position of TAGs, while vaccenic acid, being also unsaturated, was nevertheless by 90% concentrated in the sn-1,3 positions of V-TAGs. Unusual FAs were related to each other in the mechanism of their biosynthesis. In fact, hexadecenoic acid biosynthesis produced by palmitic acid desaturation, was, on the one hand, further desaturated forming palmitolinoleic acid, and, on the other hand, converted to vaccenic acid via C₂ elongation.