Oviposition deterrents from the egg masses of the adzuki bean borer, Ostrinia scapulalis and Asian corn borer, O. furnacalis

Bioassays using gravid females of the adzuki bean borer, Ostrinia scapulalis (Walker), and the Asian corn borer, O. furnacalis (Guenée) (Lepidoptera: Crambidae), showed that the presence of an egg mass of a conspecific deters oviposition. Volatile chemicals emanating from the egg mass were responsible for the deterrence, and these deterrents could be extracted from the egg mass with hexane. When fractionated using a Sep‐Pak® Plus NH₂ cartridge, the deterrents were eluted with a 98 : 2 mixture of diethyl ether and acetic acid (polar lipid fraction). The polar lipid fraction contained free fatty acids with 14–20 carbons, and palmitic acid, palmitoleic acid, and oleic acid were predominant. A blend of all identified fatty acids, a blend of six major fatty acids (palmitic, palmitoleic, stearic, oleic, linoleic, and linolenic acids), a blend of the two Z‐9‐alkenoic acids (palmitoleic and oleic acids), palmitoleic acid alone, and oleic acid alone showed deterrence against O. scapulalis which was comparable to that provoked by the full egg extract. The dose‐dependency of the deterrent effects of palmitoleic acid and oleic acid was verified in O. scapulalis. The binary blend of palmitoleic acid and oleic acid was also confirmed to deter oviposition in O. furnacalis.     

The distribution of fatty acids including petroselinic and tariric acids in the fruit and seed oils of the Pittosporaceae, Araliaceae, Umbelliferae, Simarubaceae and Rutaceae

The fatty acid composition of the fruit oils or seed oils of Pittosporaceae (eight genera, 10 species), Araliaceae (two species), Simarubaceae (three species), and of one umbelliferous and one rutaceous species were determined by gas chromatography, argentation TLC and ozonolysis. In the Pittosporaceae, in which the major C₁₈ fatty acid of all species was either oleic acid (18:1, 9c) or linoleic acid (18:2, 9c, 12c), large amounts of C₂₀ and C₂₂ fatty acids seem to occur regularly. Petroselinic (18:1, 6c) and tariric (18:1, 6a) acids were absent. However, petroselinic acid was the major fatty acid in the Araliaceae and Umbelliferae. In these two families only small amounts of C₂₀ and C₂₂ acids were detected and tariric acid was absent. The Rutales contained relatively high amounts of trans-octadecenoic acids (18:1, 9t). Tariric acid was the major fatty acid in the two species of Picramnia (Simarubraceae), which also contained small amounts of petroselinic acid. The major fatty acids in Ailanthus glandulosa (Simarubaceae) and Phellodendron amurense (Rutaceae) were linoleic or linolenic acid (18:3, 9c, 12c, 15c); these species contained neither tariric nor petroselinic acid and the levels of C₂₀ and C₂₂ fatty acids were low. The appearance of schizogenous resin canals and polyacetylenes and the absence of iridoids and petroselinic acid allows the Pittosporaceae to be separated from the Rutales and Araliales and to be placed in an independent order, the Pittosporales. Arguments for a rather close relationship of the Pittosporales to the Araliales and Cornales (including the Escalloniaceae) are presented.     

Seasonal variation in triacylglyceride fatty acids of dwarf mistletoes

Fatty acids in the triacylglyceride fraction of three species of dwarf mistletoe (Arceuthobium, Viscaceae) showed considerable seasonal variation in proportions of saturated acids and some differences in chain length for those fatty acids. Early summer aerial shoot tissue contained 34–49% saturated fatty acids, while the same species in late October had only 8–15% saturated fatty acids. Fatty acids with a chain length of C₂₀ or greater comprised 18–25% of the total in late June but only 1.5–6.4% in the autumn. Three other species analysed in only one season showed similar saturated fatty acids, and chain length patterns were also parallel to the seasonally varying species analysed in the same season. The ratio of linolenic to oleic acid remained constant with season but linolenic acid increased from less than 1% in June to 7–8% in October samples.     

Specificity of fatty acid composition of highly migratory fish. A comparison of docosahexaenoic acid content in total lipids extracted in various organs of bonito (Euthynnus pelamis)

Fatty acid composition of lipids in various organs of the bonito (Euthynnus pelamis), a typical species within the tuna species, caught in the sea off the Pacific coast of Japan, was determined by gas-liquid chromatography. The major fatty acids of all organs examined were palmitic acid (16:0), palmitoleic acid (16:1), oleic acid (18:1), icosapentaenoic acid (20:5), and docosahexaenoic acid (22:6). 22:6 (DHA) was the dominant fatty acid accounting for 25% or more of the total fatty acids in all organs of the bonito, caught in the sea off the Japanese coast.     

Changes in the lipid and fatty acid composition of hemolymph and ovaries during the reproductive cycle of Labidura riparia

Lipid metabolism was investigated during the reproductive cycle of Labidura riparia (Pallas). The lipid classes and their constitutive fatty acids present in hemolymph and ovaries were measured using thin‐layer chromatography and gas‐liquid chromatography. In the hemolymph, total lipids increase steadily from the previtellogenic period to vitellogenic arrest. These lipids are predominantly diacylglycerols and phospholipids. In the ovaries, total lipids increase during vitellogenesis then decrease during the vitellogenesis arrest period. The major lipids are triacylglycerols, followed by phospholipids. In both hemolymph and ovaries, all lipid classes contained variable proportions of seven main fatty acids: the saturated fatty acids myristic acid (14:0), palmetic acid (16:0), and stearic acid (18:0); the monounsaturated fatty acids palmitoleic acid (16:1) and oleic acid (18:1); and the polyunsaturated fatty acids linoleic acid (18:2) and linolenic acid (18:3). Unsaturated fatty acids predominate throughout the reproductive cycle. The percentage compositions of total and triacylglycerol fatty acids do not change markedly during the reproductive cycle in hemolymph nor in ovaries, with 18:2, 18:1 and 16:0 fatty acids being the major components. However, for diacylglycerols and phospholipids, the proportions of fatty acids vary systematically. For phospholipids during the vitellogenesis period, 18:2 increases considerably whereas other fatty acids decrease; for diacylglycerols, these fatty acids vary in the reverse way.     

Phospholipid fatty acids from exocrine and reproductive tissues of male american cockroaches,Periplaneta americana (L.)

We present the phospholipid fatty acid compositions, determined by GLC,* of four individual tissues (testes, mushroom glands, conglobate glands, and salivary glands) from adult male cockroaches, P. americana. The testes phospholipids contained higher proportions of palmitic acid than did the exocrine tissues (16% vs about 8%). This was also true for palmitoleic (2.3% vs 0.4–1.3%), oleic (49% vs 30–35%), and linolenic acids (7% vs 0.5–2.8%). Testicular extracts were lower in linoleic acid (16%) than were the exocrine gland extracts (at 40–45%). All four tissues also contained low proportions of several long-chain polyunsaturated fatty acids of both omega-3 and omega-6 metabolic families, including C20:3n6, C20:4n6, and C20:5n3. The data suggest that the phospholipid fatty acid profiles of specific tissues differ from each other and from those obtained from whole-insect extracts. The presence of several polyenoics from the n3 and n6 metabolic families is interpreted in the context of complex fatty acid requirements at the tissue level.     

THE BIOCHEMICAL ANALYSIS OF SOME ESTUARINE PHYTOPLANKTON SPECIES. I. FATTY ACID COMPOSITION12

The fatty acid composition of 10 species of estuarine phytoplankton was determined using gas-liquid chromatography. Nine of the species were isolated from Yaquina Bay, Oregon. These species were common components of the phytoplankton of the bay. The tenth species, Isochrysis galbana, was obtained from the Culture Collection of Algae at Indiana University. The 10 organisms comprised 3 species of Chlorophyta, 1 species of Cryptophyta, and 6 species of Chrysophyta. Twenty-eight fatty acids were found in the 10 species. The fatty acids common to all species were 14:0, 16:0, 16:1, 13:0, 18:1, and 18:2. The Chlorophyta were distinguished by a high content of linolenic acid, 18:3. The diatoms were distinguished by very low amounts of C₁₈ acids and high proportion of 20:5. All species contained a high proportion of palmitic acid, 16:0.     

Hydrocarbons and wax esters from seven species of mangrove leaves

Seven species of fresh mangrove leaves were found to contain saturated normal and branched chain hydrocarbons, mostly between C₁₆ and C₃₆ with both odd and even carbon numbers. Significant quantitative variations were found between species. Wax esters were found to contain fatty acids with chain lengths between C₁₂ and C₂₂. Palmitic (16:0) and stearic (18:0) acids were the major component saturated fatty acids, whereas, oleic (18:1) and linolenic (18:3) acids were the major unsaturate α-acids. Chain lengths of the alcohols of wax esters were between C₁₄ and C₃₆. Significant quantitative and minor qualitative differences were noted in the alcohol composition of wax esters. Hydrocarbon and wax ester compositions were characterised by the presence of low M, components in high proportions.     

Growth temperature affects accumulation of exogenous fatty acids and fatty acid composition in <Emphasis Type="Italic">Schizosaccharomyces pombe</Emphasis>

The incorporation of exogenously supplied fatty acids, palmitic acid, palmitoleic acid, oleic acid and linoleic acid, was examined in the yeast Schizosaccharomyces pombe at two growth temperatures, 20 °C and 30 °C. Fatty acids supplied to S. pombe in the growth medium were found to be preferentially incorporated into the cells, becoming a dominant species. The relative increase in exogenous fatty acids in cells came at the expense of endogenous oleic acid as a proportion of total fatty acids. Lowering the temperature at which the yeast were grown resulted in decreased levels of incorporation of the fatty acids palmitic acid, palmitoleic acid and linoleic acid compared to cells supplemented at 30 °C. In addition, the relative amount of the endogenously produced unsaturated fatty acid oleic acid, while greatly reduced compared to unsupplemented cells, was increased in cells supplemented with fatty acids at 20 °C compared to supplemented cells at 30 °C. The differential production of oleic acid in S. pombe cells indicates that regulation of unsaturated fatty acid levels, possibly by control of the stearoyl-CoA desaturase, is an important control point in membrane composition in response to temperature and diet in this species.     

Oleaginous yeast Meyerozyma guilliermondii shows fermentative metabolism of sugars in the biosynthesis of ethanol and converts raw glycerol and cheese whey permeate into polyunsaturated fatty acids

We studied the biotechnological potential of the recently isolated yeast Meyerozyma guilliermondii BI281A to produce polyunsaturated fatty acids and ethanol, comparing products yields using glucose, raw glycerol from biodiesel synthesis, or whey permeate as substrates. The yeast metabolism was evaluated for different C/N ratios (100:1 and 50:1). Results found that M. guilliermondii BI281A was able to assimilate all tested substrates, and the most efficient conversion obtained was observed using raw glycerol as carbon source (C/N ratio 50:1), concerning biomass formation (5.67 g·L⁻¹) and lipid production (1.04 g·L⁻¹), representing 18% of dry cell weight. Bioreactors experiments under pH and aeration-controlled conditions were conducted. Obtained fatty acids were composed of ~67% of unsaturated fatty acids, distributed as palmitoleic acid (C_16:1, 9.4%), oleic acid (C_18:1, 47.2%), linoleic acid (C_{18:2 n−6}, 9.6%), and linolenic acid (C_{18:3 n−3}, 1.3%). Showing fermentative metabolism, which is unusual for oleaginous yeasts, M. guilliermondii produced 13.7 g·L⁻¹ of ethanol (yields of 0.27) when growing on glucose medium. These results suggest the promising use of this uncommonly studied yeast to produce unsaturated fatty acids and ethanol using cheap agro-industrial residues as substrates in bioprocess.     

Fatty Acids in the Species of Several Zygomycete Taxa

The composition of fatty acids synthesized de novo by thirty strains of zygomycetes from various taxa was studied. The qualitative fatty acid compositions of the fungal lipids were found to be virtually identical, but there were significant differences in the contents of individual acids. Highly active producers of essential C₁₈ fatty acids, with their content exceeding 30–40% of total fatty acids, were discovered among the fungi of the families Mucoraceae, Pilobolaceae, and Radiomycetaceae. Linoleic acid was found to predominate in the fungi of the genera Radiomyces, Mycotypha, and Circinella, and linolenic acid (identified as its -isomer by gas-liquid chromatography), in the fungi of the genera Absidia, Circinella, Pilaira, and Hesseltinella. The total yield (mg/l) of bioactive acids (C_18:3, C_18:2, C_18:1) varied from 761.4 in Pilaira anomala to 3477.9 in Syncephalastrum racemosum; the total yield of essential acids, from 520.7 in Pilaira anomala to 1154.5 in Hesseltinella vesiculosa; of linoleic acid, from 279.7 in Pilaira anomala to 836.3 in Mycotypha indica; and of linolenic acid, from 120.8 in Mycotypha indica to 708.0 in Hesseltinella vesiculosa. The data on the efficient synthesis of these acids make the actively producing strains promising for biotechnological synthesis of commercially valuable lipids. Linderina pennispora VKM F-1219, a zygomycete of the family Kickxellaceae, which was earlier singled out into the order Kickxellales, was shown to differ from zygomycetes of the order Mucorales in having a high content of cis-9-hexadecenoic (palmitoleic) acid, reaching 37.0% of the fatty acid total.     

Analysis of whole cellular fatty acids and anastomosis relationships of binucleate Rhizoctonia spp. associated with Ceratobasidium cornigerum

Previous research has demonstrated that whole cellular fatty acids analysis is a useful tool for identifying and establishing taxonomic relationships between anastomosis groups (AGs) and related Rhizoctonia isolates. In this experiment, the composition of fatty acid of 28 isolates of teleomorph genus Ceratobasidium cornigerum, consisting of binucleate Rhizoctonia, AG-A, AG-B(o), AG-C, AG-P, and AG-Q, was evaluated using gas chromatography. Eleven fatty acids identified, i.e., myristic, pentadecanoic, palmitic, 2-hydroxypalmitic, palmitoleic, heptadecanoic, 9-heptadecenoic, stearic, oleic, linoleic, and linolenic acids, were present in isolates of AG-A, AG-B(o), AG-C, AG-P, and AG-Q. The major fatty acids, palmitic, oleic, and linoleic acids, were common in all isolates, constituting 87.1% to 94.7% of the whole cellular fatty acids identified. Isolates within the same AG were closely clustered, whereas isolates from different AGs were clearly and distinctly clustered based on average linkage cluster analysis of whole cellular fatty acids. Principal-component analysis generated from all fatty acids also confirmed the divergent separation of the 5 AGs of binucleate Rhizoctonia.     

The long-chain fatty acid composition of yeasts used in the brewing industry

Summary The cellular long-chain fatty acids of 69 strains of yeasts, representing 29 species associated with the brewing industry, were extracted by saponification and analyzed asmethyl esters by gas chromatography. The strains were characterized by the presence of palmitic, palmitoleic, stearic, oleic, linoleic and linolenic acid as the major fatty acids. The strains were divided into six groups on the basis of their fatty acid content. With this method it was possible to differentiate between the yeasts on species and, in some instances, on strain level.     

ACTIVATION OF GUANYLATE CYCLASE IN SYNAPTIC PLASMA MEMBRANES OF CEREBRAL CORTEX BY FREE FATTY ACIDS

Guanylate cyclase (EC 4.6.1.2) of synaptic plasma membranes of rat cerebral cortex was stimulated about 6-fold by several unsaturated fatty acids (arachidonic, linolenic, linoleic, oleic, palmitoleic and myristoleic acid). Ricinoleic acid (12-hydroxyoleic acid) was much less effective. Saturated fatty acids (C₁₀ and C₁₄-C₂₀) and the methylester of linoleic acid were ineffective. Stimulation by linoleic acid was influenced by the concentration of enzyme protein. At 480 μg/ml of protein 0.6 mm -linoleic acid produced maximal activation of 6-fold_ Activity stimulated by linoleic acid examined with 1.0 mm -GTP was maximal at pH 7.8-7.9 and with 2 mm -MnCl₂, whereas basal activity showed broad optimal pH and Mn²⁺-concentration dependence. Activation of the enzyme by linoleic acid was only partially reversed by washing. Particulate guanylate cyclase of heart, small intestine, adrenal medulla, liver and lung was also activated by linoleic acid. The extents of activation (1.5-14.7-fold) by linoleic acid and the concentrations (0.2-1.0 mat) required for maximal activation depended on the tissues.     

Anti‐Androgenic Activity of Fatty Acids

In this study, we show that 5α‐reductase derived from rat fresh liver was inhibited by certain aliphatic free fatty acids. The influences of chain length, unsaturation, oxidation, and esterification on the potency to inhibit 5α‐reductase activity were studied. Among the fatty acids we tested, inhibitory saturated fatty acids had C₁₂–C₁₆ chains, and the presence of a C?C bond enhanced the inhibitory activity. Esterification and hydroxy compounds were totally inactive. Finally, we tested the prostate cancer cell proliferation effect of free fatty acids. In keeping with the results of the 5α‐reductase assay, saturated fatty acids with a C₁₂ chain (lauric acid) and unsaturated fatty acids (oleic acid and α‐linolenic acid) showed a proliferation inhibitory effect on lymph‐node carcinoma of the prostate (LNCaP) cells. At the same time, the testosterone‐induced prostate‐specific antigen (PSA) mRNA expression was down‐regulated. These results suggested that fatty acids with 5α‐reductase inhibitory activity block the conversion of testosterone to 5α‐dihydrotestosterone (DHT) and then inhibit the proliferation of prostate cancer cells.     

Volatile constituents and fatty acid composition of lipids in Durio zibethinus

The predominating flavour compounds in the fruit pulp of Durio zibethinus were hydrogen sulfide, ethyl hydrodisulfide and several dialkyl polysulfides, particularly (C₂H₅)₂S_n, where n = 2 or 3. Ethyl acetate, 1,1-diethoxyethane and ethyl 2-methylbutanoate contribute to an additional fruity odour note. Hydrodisulfides are probably the precursors of the dialkyl sulfides. In the pericarp and seed no volatile sulfur compounds could be detected. The fatty acid composition of the lipids in pericarp, pulp and seed depended on the origin and/or harvest season of the fruit. The main components were oleic and palmitic acids or arachidic acid together with appreciable quantities of palmitoleic, stearic, linoleic and linolenic acids.     

Triglyceride metabolism in germinating Andropogon gayanus seeds

Seed triglycerides of Andropogon gayanus contained 17 fatty acid moieties, principally palmitic, oleic and linoleic acids. These were distributed in an essentially random manner amongst the triglycerides to form the following main types: POL, PLL, OOL, LLO and LLL. Triglycerides decreased during both light and dark germination but there was no evidence for selective hydrolysis. Free fatty acids appear to be derived from triglyceride hydrolysis but the free and triglyceride fatty acid composition differed. Less palmitic, oleic and linoleic acids and more stearic, linolenic and C₂₀-acids were found in the free state than combined in the triglycerides. Free fatty acids did not accumulate during germination.     

Expression and Characterization of CYP52 Genes Involved in the Biosynthesis of Sophorolipid and Alkane Metabolism from Starmerella bombicola

Three cytochrome P450 monooxygenase CYP52 gene family members were isolated from the sophorolipid-producing yeast Starmerella bombicola (former Candida bombicola), namely, CYP52E3, CYP52M1, and CYP52N1, and their open reading frames were cloned into the pYES2 vector for expression in Saccharomyces cerevisiae. The functions of the recombinant proteins were analyzed with a variety of alkane and fatty acid substrates using microsome proteins or a whole-cell system. CYP52M1 was found to oxidize C₁₆ to C₂₀ fatty acids preferentially. It converted oleic acid (C_18:1) more efficiently than stearic acid (C_18:0) and linoleic acid (C_18:2) and much more effectively than α-linolenic acid (C_18:3). No products were detected when C₁₀ to C₁₂ fatty acids were used as the substrates. Moreover, CYP52M1 hydroxylated fatty acids at their ω- and ω-1 positions. CYP52N1 oxidized C₁₄ to C₂₀ saturated and unsaturated fatty acids and preferentially oxidized palmitic acid, oleic acid, and linoleic acid. It only catalyzed ω-hydroxylation of fatty acids. Minor ω-hydroxylation activity against myristic acid, palmitic acid, palmitoleic acid, and oleic acid was shown for CYP52E3. Furthermore, the three P450s were coassayed with glucosyltransferase UGTA1. UGTA1 glycosylated all hydroxyl fatty acids generated by CYP52E3, CYP52M1, and CYP52N1. The transformation efficiency of fatty acids into glucolipids by CYP52M1/UGTA1 was much higher than those by CYP52N1/UGTA1 and CYP52E3/UGTA1. Taken together, CYP52M1 is demonstrated to be involved in the biosynthesis of sophorolipid, whereas CYP52E3 and CYP52N1 might be involved in alkane metabolism in S. bombicola but downstream of the initial oxidation steps.     

Cadmium Alters the Concentration of Fatty Acids in THP-1 Macrophages

Fatty acid composition of human immune cells influences their function. The aim of this study was to evaluate the effects of known toxicant and immunomodulator, cadmium, at low concentrations on levels of selected fatty acids (FAs) in THP-1 macrophages. The differentiation of THP-1 monocytes into macrophages was achieved by administration of phorbol myristate acetate. Macrophages were incubated with various cadmium chloride (CdCl₂) solutions for 48 h at final concentrations of 5 nM, 20 nM, 200 nM, and 2 μM CdCl₂. Fatty acids were extracted from samples according to the Folch method. The fatty acid levels were determined using gas chromatography. The following fatty acids were analyzed: long-chain saturated fatty acids (SFAs) palmitic acid and stearic acid, very long-chain saturated fatty acid (VLSFA) arachidic acid, monounsaturated fatty acids (MUFAs) palmitoleic acid, oleic acid and vaccenic acid, and n-6 polyunsaturated fatty acids (PUFAs) linoleic acid and arachidonic acid. Treatment of macrophages with very low concentrations of cadmium (5–200 nM) resulted in significant reduction in the levels of arachidic, palmitoleic, oleic, vaccenic, and linoleic acids and significant increase in arachidonic acid levels (following exposure to 5 nM Cd), without significant reduction of palmitic and stearic acid levels. Treatment of macrophages with the highest tested cadmium concentration (2 μM) produced significant reduction in the levels of all examined FAs: SFAs, VLSFA, MUFAs, and PUFAs. In conclusion, cadmium at tested concentrations caused significant alterations in THP-1 macrophage fatty acid levels, disrupting their composition, which might dysregulate fatty acid/lipid metabolism thus affecting macrophage behavior and inflammatory state.     

Fatty acids of some cornaceae,hydrangeaceae, aquifoliaceae,hamamelidaceae and styracaceae

Seed, kernel or fruit oils of the Cornaceae (nine species). Hydrangea, Hamamelis, Ilex (Aquifoliaceae) and the Styracaceae (two species) were analysed for fatty acid composition. Special attention was paid to the occurrence of petroselinic acid (18: 1Δ6c). In the species investigated. C₁₈ acids were always present in greater quantities than C₁₆ fatty acids; C₂₀ and C₂₂ acids were only minor components. The Cornaceae show differing fatty acid patterns which correlate well with anatomical, morphological and other chemical data. In Cornus, Curtisia, Mastixia and Corokia linoleic acid predominates, whereas linoleic and linolenic acid form the major components in Davidia and Nyssa. 18 : 1Δ6c, an aralioid type, occurs in large amounts in Aucuba and Griselinia. Hamamelis, Hydrangea and Ilex show a common fatty acid pattern with linoleic acid as the dominant component in all cases. Classification currently based on morphological and anatomical differences between the two species of Styracaceae which were investigated here should include their different fatty acid compositions: in Halesia linoleic acid predominates over oleic acid, whereas in Styrax equal amounts of these two acids are found.