Novel Odd-Chain Fatty Acids with a Terminal Double Bond in Ovaries of the Limpet <Emphasis Type="Italic">Cellana toreuma</Emphasis>

Our previous study characterized highly diverse dienoic fatty acids (FA), in particular an uncommon non‐methylene‐interrupted (NMI) FA, in the ovaries of the Japanese limpet Cellana toreuma belonging to the archaeogastropods, but many minor chemically unidentified FA remain. In this study, among previously unidentified FA (less than 0.1% of total FA), four novel NMI FA with a terminal double bond [7,18‐nonadecadienoic (19:2Δ7,18), 11,18‐nonadecadienoic (19:2Δ11,18), 7,20‐heneicosadienoic (21:2Δ7,20), and 11,20‐heneicosadienoic (21:2Δ11,20) acids] were found, along with known 14‐pentadecenoic (15:1Δ14), 16‐heptadecenoic (17:1Δ16), and 9,18‐nonadecadienoic (19:2Δ9,18) acids, based on capillary GC–MS of their methyl esters, 3‐pyridylcarbinol derivatives, and argentation thin‐layer chromatography. From our findings, possible biosynthetic pathways for the novel FA are discussed.     

Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet <Emphasis Type="Italic">Cellana toreuma</Emphasis>

In our previous study, unusual odd‐numbered dienoic acids with a terminal olefin were found as minor components in ovaries of the Japanese limpet Cellana toreuma, and the synthetic interests have been focused onto their structural confirmation and the inspection into their potential biological activity. Here, we describe an efficient and stereoselective total synthesis of two new unusual dienoic acids, 19:2?7,18 and 21:2?7,20, through a common pathway involving the strategic combination of alkyne‐zipper reaction and Lindlar hydrogenation for the construction of their unique carbon chains. In our synthetic study, 2‐propyn‐1‐ol was at first subjected to alkylation and alkyne‐zipper reaction to form the two fragments, and the subsequent carbon chain elongation was achieved by the usual coupling reaction to obtain the C‐19 and C‐21 products bearing an internal acetylenic group. Then, the internal acetylenic group of these products was subjected to Lindlar hydrogenation to form a Z‐alkenyl moiety, and the subsequent deprotection of the products was carried out under an acidic condition without isomerization of the internal Z‐alkenyl group. Total synthesis of target fatty acids, 19:2?7,18 and 21:2?7,20, was finally accomplished by two‐step oxidation of the resulting alcohols into carboxylic acids in a highly chemoselective manner, and the structures of these unusual natural fatty acids were finally elucidated by identifying the GC–MS spectra of the methyl esters of authentic and synthetic fatty acids.     

Non-methylene Interrupted and Hydroxy Fatty Acids in Polar Lipids of the Alga Grateloupia turuturu Over the Four Seasons

Phospholipids (PL) and glycolipids (GL) FA in the edible Rhodophyta Grateloupia turuturu, from Brittany, France, were investigated over four seasons. The major lipid class was GL in all seasons (around 45 %). More than 80 FA occurred in polar lipids, with chains from C₁₂ to C₂₆, identified as methyl esters and N-acyl pyrrolidides by gas chromatography–mass spectrometry (GC–MS). PUFA occurred at up to 47.1 % (summer) in PL, and up to 43.6 % (summer) in GL. The major PUFA were 20:5n-3 (12.2 % in PL and 29.0 % in GL) and 20:4n-6 (25.6 % in PL and 10.4 % in GL). The unusual 18:3n-7 acid was identified in PL up to 2.2 %. Several minor unsaturated FA were identified in PL and are previously unreported in seaweeds, namely 14-tricosenoic, 15-tetracosenoic, 5,11-octadecadienoic and 5,9-nonadecadienoic. Also unprecedented in seaweeds, ten 2-hydroxy and three 3-hydroxy FA occurred mainly in PL, 13.9 % in spring with the 3-hydroxyhexadecanoic acid as the major one (8.1 % winter). Three n-9 monounsaturated 2-hydroxy FA occurred in PL. The 2-hydroxy-15-tetracosenoic acid was characterized as the dimethyl disulfide adduct of its methyl ester. The 2-hydroxy-16-pentacosenoic and 2-hydroxy-17-hexacosenoic acids were identified by comparison of mass spectra and GC mobilities with those of the 2-hydroxy-15-tetracosenoic acid, and of other homogeneous FA series. These rare n-9 monounsaturated 2-hydroxy FA are unprecedented in seaweeds.     

Fatty Acids in Liver,Muscle and Gonad of three Tropical Rays including Non-Methylene-Interrupted Dienoic Fatty Acids

Scientific investigation of lipids in Elasmobranchs has been conducted mainly on shark species. Because rays seem to be neglected, this study was performed to examine the complete fatty acid (FA) composition with a particular interest for long-chain polyunsaturated FA (PUFA) content in different tissues of three ray species including parts usually discarded. The total FA and PUFA profiles of total lipids were determined in muscle, liver, and gonad of Rhinobatos cemiculus, Rhinoptera marginata, and Dasyatis marmorata, the most often caught ray species from the East Tropical Atlantic Ocean. Fifty FA were characterized as methyl esters and N-acyl pyrrolidides by gas chromatography/mass spectrometry, showing significant levels of 20:5n-3 (EPA) (up to 5.3%) and 22:5n-3 (DPA) (up to 7.3%), high levels of 20:4n-6 arachidonic (ARA) (4.8–8.6% of total FA) and 22:6n-3 (DHA) (up to 20.0%). The results show that muscle, liver and gonad of rays can provide high amounts of essential PUFA, specially DHA, for direct human nutrition or the food processing industry. High proportions of DHA were particularly found in all samples of R. cemiculus (11.6–20.0%), and in muscle and liver of D. marmorata (11.1–16.1%). Regarding the high amounts of (n-3) PUFA, this study shows that these rays deserve a better up-grading, including the normally discarded parts, and describes the occurrence of unusual NMID FA in all tissues studied. Five non-methylene-interrupted dienoic fatty acids (NMID FA) (0–3.4%) were reported, including previously known isomers, namely 20:2 Δ7,13, 20:2 Δ7,15, 22:2 Δ7,13, 22:2 Δ7,15, and new 22:2 Δ6,14. These acids are quite unusual in fish and unprecedented in rays. The 22:2 Δ6,14 acid occurred in gonads of male specimens of R. cemiculus at 2.9%.     

Dietary Counseling and Probiotic Supplementation During Pregnancy Modify Placental Phospholipid Fatty Acids

It has previously been shown that maternal nutrition affects the fetal environment, with consequences for the infant’s health. From early pregnancy onwards participants here received a combination of dietary counseling and probiotics (Lactobacillus GG and Bifidobacterium lactis Bb12; n = 10), dietary counseling with placebo (n = 12), or placebo alone (n = 8). The major differences in placental fatty acids were attributable to a higher concentration of n-3 polyunsaturated fatty acids in both intervention arms than in controls. Further, dietary counseling with probiotics resulted in higher concentrations of linoleic (18:2n-6) and dihomo-γ-linolenic acids (20:3n-6) compared with dietary counseling with placebo or controls. Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users.     

Sources and Bioactive Properties of Conjugated Dietary Fatty Acids

The group of conjugated fatty acids known as conjugated linoleic acid (CLA) isomers have been extensively studied with regard to their bioactive potential in treating some of the most prominent human health malignancies. However, CLA isomers are not the only group of potentially bioactive conjugated fatty acids currently undergoing study. In this regard, isomers of conjugated α‐linolenic acid, conjugated nonadecadienoic acid and conjugated eicosapentaenoic acid, to name but a few, have undergone experimental assessment. These studies have indicated many of these conjugated fatty acid isomers commonly possess anti‐carcinogenic, anti‐adipogenic, anti‐inflammatory and immune modulating properties, a number of which will be discussed in this review. The mechanisms through which these bioactivities are mediated have not yet been fully elucidated. However, existing evidence indicates that these fatty acids may play a role in modulating the expression of several oncogenes, cell cycle regulators, and genes associated with energy metabolism. Despite such bioactive potential, interest in these conjugated fatty acids has remained low relative to the CLA isomers. This may be partly attributed to the relatively recent emergence of these fatty acids as bioactives, but also due to a lack of awareness regarding sources from which they can be produced. In this review, we will also highlight the common sources of these conjugated fatty acids, including plants, algae, microbes and chemosynthesis.     

Role of n-3 Fatty Acids on Bile Acid Metabolism and Transport in Dyslipidemia: A Review

Dietary n-3 fatty acids, especially of marine origin, eicosapentaenoic acid (20:5n-3) and docosahexaenoic acid (22:6n-3), have always been lauded for their profound effects on regulating the risk factors for major metabolic disorders. Yet, their consumption rate is poor compared to n-6 fatty acids [linoleic acid (18:2n-6)], which are predominantly consumed. Hence, the skewed n-6 to n-3 fatty acid ratio may have a bearing on the risk factors of various diseases, including dyslipidemia. Dyslipidemia and other lifestyle diseases associated with it, such as diabetes, obesity, hypertension, are a growing concern in both developed and developing countries. A common strategy for addressing dyslipidemia involves bile acid (BA) sequestration, to interrupt the enterohepatic circulation of BA, resulting in the modulation of lipid absorption in the intestine, thereby normalizing the levels of circulating lipids. The BA homeostasis is under the tight control of hepatic and enteric BA transporters. Many investigations have reported the effects of dietary constituents, including certain fatty acids on the reabsorption and transport of BA. However, a critical review of the effects of n-3 fatty acids on BA metabolism and transport is not available. The present review attempts to explore certain unmapped facets of the n-3 fatty acids on BA metabolism and transport in dyslipidemia, and their interplay with biological processes involving lipid rafts and gut microbiome.     

Quantification of Fatty Acids and their Regioisomeric Distribution in Triacylglycerols from Porcine and Bovine Sources Using 13C NMR Spectroscopy

The uptake of specific fatty acids in humans is dependent on their position on the glycerol backbone. There is a great interest in methods that can access this information fast and accurately. By way of high-resolution NMR, we have analyzed TAG extracted from pig and beef tissues and obtained quantitative data for the composition and regioisomeric distribution of all major unsaturated fatty acids usually found in these source materials, using a combination of manual integration and deconvolution of ¹³C NMR spectra. In addition, we have developed a method for determining composition and regioisomeric distribution of the two main saturated fatty acids found in pork (16:0, 18:0). The results are discussed in relation to species-specific genetic characteristics of fatty acid and TAG biosynthesis. The developed method could support decisions related to breeding for desired fatty acid profiles, and stimulate further methodology developments using high field NMR.     

Multiply Methyl-Branched Fatty Acids and Diacids in the Polar Lipids of a Microaerophilic Subsurface Microbial Community

A previously unreported series of di- and tri-methylated fatty acids, as well as saturated and monounsaturated diacids were identified in polar lipids isolated from environmental subsurface sediment samples. Mechanisms are proposed for their formation, but their origin and role in cell membranes remains unknown.     

Preferential Partitioning of Rumen-Protected n-3 and n-6 Fatty Acids into Functionally Different Adipose Tissues

Lipids are stored at various sites inside the body as adipose tissue (AT). These include subcutaneous, abdominal, and intermuscular locations. The AT substantially differ in their metabolic function. It is, however, unclear whether AT have specific requirements for individual essential n-3 and n-6 fatty acids (FA). If so, control mechanisms would partition FA from the blood. To investigate the hypothesis of a selective FA incorporation, 18 beef heifers were fed diets supplemented with 60 g/kg diet with lipids from either fish oil (FO) or sunflower oil (SO). The lipids had partially been rumen-protected to ruminal biohydrogenation of n-3 and n-6 FA. The AT analyzed for n-3 and n-6 FA by gas chromatography were obtained from pericardial, longissimus thoracis (LT) intermuscular, perirenal, and subcutaneous sites. The greatest proportions of n-3 and n-6 FA were found in the pericardial AT. Despite generally low abundance, n-3 FA proportions increased with FO compared to SO supplementation in all AT, but to a different extent. No such partitioning was found for the n-6 FA when supplementing SO. Concomitantly, the n-6/n-3 FA ratio was reduced with FO in all AT, except in the pericardial AT. The latter has specific metabolic functions and thus appears to be quite resistant to diet-induced changes in FA profile in order to maintain its function. The present findings showed the special role of specific n-3 and n-6 FA in bovine AT.     

n-3 Polyunsaturated Fatty Acids Improve Inflammation via Inhibiting Sphingosine Kinase 1 in a Rat Model of Parenteral Nutrition and CLP-Induced Sepsis

The sphingosine kinase 1 (SphK1)/sphingosine‐1‐phosphate (S1P) pathway plays a key role in inflammation. Parenteral nutrition containing n‐3 polyunsaturated fatty acids (n‐3 PUFA) may regulate inflammatory reactions. The aim of this study is to determine whether n‐3 PUFA may improve inflammatory responses by neutralizing SphK1 signaling. Rat models of parenteral nutrition, cecal ligation and puncture (CLP)‐induced sepsis were generated. Male Sprague–Dawley rats were operated for CLP on day 2 after venous catheterization. The rats were randomized to receive normal saline (NS; n = 20), parenteral nutrition (PN; n = 20), or PN + fish oil (FO; n = 20) for 5 days. The daily intake of fish oil (1.25–2.82 g EPA and 1.44–3.09 g DHA per 100 ml) in the FO group was approximately 1.8 g/kg body weight/day. Rats in the control group (n = 10) were subjected to sham operation and received a chow diet. Spleen tissues were collected for SphK1 and S1P receptor expression analysis. Our data showed that n‐3 PUFA ameliorated the survival rate. SphK1 expression and its enzymatic activity were significantly upregulated in sepsis rats. Furthermore, mRNA and protein levels of S1PR3, but not S1PR1, were also facilitated after CLP. However, PN + FO dramatically decreased SphK1 mRNA level and its enzymatic activity. S1PR3 expression was also attenuated by FO addition. In conclusion, the anti‐inflammatory effect of n‐3 PUFA may be linked to the inhibition of the SphK1/S1P pathway in a rat model of parenteral nutrition and CLP‐induced sepsis.     

Lipids and Fatty Acids of the Gonads of Sea Urchin Diadema setosum (Echinodermata) From the Coastal Area of the Nha Trang Bay,Central Vietnam

The sea urchin Diadema setosum is edible and desirable as food by locals in central Vietnam and a promising target for potential fishing. The lipid profiles of the gonads of the sea urchin inhabiting the coastal area in Nha Trang Bay are studied for the first time. The determination of the content of the total lipids (TL), total phospholipids (PL), monoacylglycerols (MAG), diacylglycerols (DAG), triacylglycerols (TAG), cholesterol (Chol), sterol esters, and free fatty acids (FFA) is analyzed by high-performance thin layer chromatography (HPTLC); the phosphatidylserine (PS), phosphatidylethanolamine (PE), phosphatidylinositol (PI), phosphatidylcholine (PC), lysophosphatidylcholine (LPC), and sphingomyelin (SM) are determined by high-pressure liquid chromatography (HPLC); and the fatty acid levels of TLs are identified using gas chromatography (GC). Non-polar TAG, FFA, Chol, and DAG dominated. The content of total PL is significant. PC is abundant among PL fractions, followed by PE, PI, and PS. The TLs contain a high proportion of PUFA, mainly due to arachidonic fatty acid and eicosapentanoic fatty acid. The (n−6)/(n−3) ratio is 1.68, and the atherogenic and thrombogenic indexes of D. setosum are 1.13 and 0.73. The results can be used in the development of marine bioprospecting and methodological approaches for the creation of functional substances.     

Hypolipidemic Effects of Phospholipids (PL) Containing n-3 Polyunsaturated Fatty Acids (PUFA) Are Not Dependent on Esterification of n-3 PUFA to PL

Phospholipids (PL) containing n‐3 polyunsaturated fatty acids (PUFA) have beneficial effects of maintaining and promoting health compared with triacylglycerols (TAG) containing n‐3 PUFA or general PL. This study evaluated the effects of dietary PL containing n‐3 PUFA and elucidated the effects of the glycerophosphate structure and n‐3 PUFA on fatty acid (FA) metabolism in rats. Rats were fed a basal diet containing soybean oil alone, TAG containing n‐3 PUFA (1.8 %), soybean PL (2.7 %), PL containing n‐3 PUFA (2.7 %), or TAG containing n‐3 PUFA (1.8 %) + soybean PL (2.7 %). The present n‐3 PUFA‐supplemented diets had similar FA compositions, and the PL diets had similar PL compositions. TAG containing n‐3 PUFA reduced serum TAG contents, but did not affect serum cholesterol contents compared with soybean oil alone. PL diets containing n‐3 PUFA and the combination of TAG containing n‐3 PUFA and soybean PL resulted in decreased serum and liver TAG contents compared with the diet containing soybean oil alone, reflecting enhanced liver FA β‐oxidation. The results of this study show that TAG containing n‐3 PUFA with added soybean PL affects serum and liver TAG and cholesterol contents to a similar degree as PL containing n‐3 PUFA. TAG containing n‐3 PUFA and soybean PL are widely used as functional food ingredients and pharmaceutical constituents and are inexpensive compared with PL containing n‐3 PUFA. Therefore, the combination of TAG containing n‐3 PUFA and soybean PL has potential as a useful and inexpensive component of functional foods.     

Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids

Plant oils rich in oxygenated fatty acids (FAs) are of interest as renewable raw materials for industry. Previous studies reported unusual oxygenated FAs in the seed lipids of Plantago major and P. ovata. To determine if oxygenated FAs are a common component of Plantago seed oils, seed fatty acyl quality and quantity were determined for 23 Plantago species. Fatty acyl content, as a percentage of dry weight, ranged from 4.9 % in P. sempervirens to 18.8 % in P. coronopus. Oxygenated FAs were a frequent, but not ubiquitous component of Plantago seed lipids, reaching a level of almost 15 % in the seeds of P. nivalis. The oxygenated FAs were identified as isoricinoleic acid (9-hydroxy-cis-12-octadecenoic acid, IR) and 9-oxo-cis-12-octadecenoic acid (OX). When present, most species contained both IR and OX. FAs containing oxo groups have not been reported as components of the seed oil of other plant species that synthesize IR or ricinoleic acid (12-hydroxy-cis-9-octadecenoic acid), suggesting unique aspects to the pathway of oxygenated FA biosynthesis in Plantago. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) demonstrated that IR and OX are components of triacylglycerol, and triacylglycerol estolides are a minor component of the seed oil of P. lanceolata with secondary acylation by oxygenated FAs.     

GC-EI-MS Analysis of Fatty Acid Composition in Brain and Serum of Twitcher Mouse

Globoid cell leukodystrophy or Krabbe disease is an inherited autosomal recessive disorder caused by mutations in the galactosylceramidase gene. The objective of the study was to present information about the fatty acid (FA) composition of the brain and serum of twitcher mice, a mouse model of Krabbe disease, compared to wild type, in order to identify biomarker of disease progression. We defined the FA profiles by identifying the main components present in serum and brain using GC‐EI‐MS analysis. The FA percentage composition was measured and data were analyzed considering the disease and the mouse age as experimental factors. Significant correlations were established, both in brain and in serum, in the fatty acid percentage composition of twitcher compared to wild type mice. The most abundant saturated fatty acid in brain was the palmitic acid (C16:0) with mean values significantly increased in twitcher mouse (p = 0.0142); moreover, three monounsaturated, three polyunsaturated (PUFA) and a plasmalogen were significantly correlated to disease. In the serum highly significant differences were observed between the two groups for three polyunsaturated fatty acids. In fact, the docosahexaenoic acid (C22:6n3c) content was significantly increased (p = 0.0116), while the C20 PUFA (C20:3n6c and C20:5n3c) were significantly decreased in twitcher serum samples. Our study shows a specific FA profile that may help to define a possible pattern that could distinguish between twitcher and wild type; these data are likely to provide insight in the identification of new biomarkers to monitor the disease progression and thereby permit the critical analysis of therapeutic approaches.     

Interactions of Linoleic and Alpha-Linolenic Acids in the Development of Fatty Acid Alterations in Cystic Fibrosis

Patients with cystic fibrosis (CF) exhibit characteristic polyunsaturated fatty acid abnormalities, including low linoleic acid and high arachidonic acid levels that are thought to contribute to the pathophysiology of this disease. Recent studies indicate that changes in fatty acid metabolism are responsible for these abnormalities. This study examines the role of fatty acid substrate concentrations in the development of these alterations in a cultured cell model of CF. By incubating cells with varying concentrations of exogenous fatty acids, it shows that increasing the concentration of substrates from the parallel n-3 and n-6 polyunsaturated fatty acid pathways (linoleic acid and alpha-linolenic acid, respectively) not only increases formation of the products in that pathway, but also reduces metabolism in the parallel pathway. In particular, we demonstrate that high levels of linoleic acid and low levels of alpha-linolenic acid are required to observe the typical fatty acid alterations of cystic fibrosis. These results shed light on the mechanisms of fatty acid metabolic abnormalities in cystic fibrosis. They also have implications for the nutritional therapy of CF, highlighting the importance of specific fatty acid content, and in understanding the anti-inflammatory effects of n-3 fatty acids.     

Temporal Changes of Phospholipids Fatty Acids and Cholesterol in Breast Milk and Relationship with Diet

Phospholipids (PLs) and cholesterol in human milk (HM) are affected by lactation, and differential lipids are closely related to maternal diet. The contents of PLs and cholesterol in Chinese HM are quantified by gas chromatography and high performance liquid chromatography, respectively, and the relationship between differential lipids and the maternal diet is obtained by Pearson. The result shows that SFA, MUFA, and polyunsaturated fatty acid (PUFA) are not affected by lactation and geography for total fatty acids, but almost all sn‐2 fatty acids are influenced by geography and remain unchanged during lactation. Most SFAs show absolute sn‐2 selectivity and the majority of MUFAs and PUFAs are esterified at the sn‐1 position. Cholesterol (13.8–22.6 mg per 100 g milk) and 25‐hydroxycholesterol (0.45–1.01 mg per 100 g milk) increase significantly and remain constant during lactation, respectively, and they are affected by regions. In addition, the differential lipids (22:1n‐9, C9:0, trans‐PUFA, 22:4n‐6, etc.) of PLs are closely related to the maternal diet. PLs and cholesterol content differ from western research and infant formula, which will help to design an infant formula that is more suitable for Chinese babies in the future. Practical Application: Compared with PLs and cholesterol in western countries and infant formula, the specificity of Chinese HM can more accurately target the development of formulas suitable for the growth of Chinese infants. At the same time, according to the influence of the mother?s diet on the composition of HM, it is more reasonable to guide the diet of the mother.     

One-Step Concentration of Highly Unsaturated Fatty Acids from Tuna Oil by Low-Temperature Crystallization

Highly unsaturated fatty acids (HUFA), including eicosapentaenoic acid (EPA, 20:5n‐3), docosapentaenoic acid (DPA, 22:5n‐3 and 22:5n‐6) and docosahexaenoic acid (DHA, 22:6n‐3), play an important role in human health and nutrition. In this study, concentration of HUFA in free fatty acids (FFA) form by low‐temperature crystallization was investigated. For this purpose, tuna oil (7.1% EPA, 26.8% DHA) was first converted into corresponding FFA. Subsequently, crystallization conditions of various solvent types, the ratio of FFA to acetonitrile, operation temperature and crystallization time were optimized at a small scale of 2 g tuna oil fatty acids. Taking purity and yield into account, the optimum conditions were a 1:10 ratio of FFA to acetonitrile (w/v), ?60 °C, and 1 h. The optimal conditions resulted in concentrations of EPA, DHA and HUFA of 15.1, 58.4 and 79.6%, respectively, with corresponding yields of 61.5, 61.8 and 60.7%, respectively. Crystallization was carried out under the optimal conditions at a large scale of 200 g tuna oil FFA, and a similar concentration result was achieved. After evaporating away the solvent, the residual amount of acetonitrile met the US Pharmacopoeia requirement of <410 ppm. The process for enrichment of HUFA is readily scalable, effective and time‐saving.     

Fatty Acids from a Glass Sponge <Emphasis Type="Italic">Aulosaccus</Emphasis> sp. Occurrence of New Cyclopropane-Containing and Methyl-Branched Acids

In order to identify new structures, the free fatty acids from an extract of a glass sponge Aulosaccus sp. (from the north‐west Pacific) belonging to one of the least chemically investigated classes (Hexactinellida), were fractionated by RP‐HPLC and analyzed by NMR spectroscopy and GC–MS of their pyrrolidine derivatives, methyl(ethyl) esters and their dimethyl disulfide adducts. One hundred and twenty‐three C₁₂–C₃₁ acids (including nine new compounds) were detected, one hundred and ten of these compounds have not been found previously in glass sponges. The levels of common methylene‐interrupted polyenes, monoenes of the (n–7) family and less common branched‐chain components proved to be high. New acids were shown to be 5,13‐dimethyl‐tetradec‐4‐enoic, cis‐10,11‐methylene‐heptadecanoic, 10,12‐dimethyl‐octadecanoic, cis‐12,13‐methylene‐nonadecanoic, (14E)‐13‐methyl‐eicos‐14‐enoic, 19‐methyl‐eicos‐13‐enoic, cis‐20,21‐methylene‐heptacosanoic, 27‐methyl‐octacos‐21‐enoic and (22Z)‐nonacos‐22‐enoic. Some important mass spectrometric characteristics of pyrrolidides of homologous cyclopropane fatty acids are reported and discussed.     

Contents of Fatty Acids, Selected Lipids and Physicochemical Properties of Western Australian Sandalwood Seed Oil

The study was designed to characterise two extracts of Western Australian sandalwood (Santalum spicatum) seed oils for their physicochemical and lipid characteristics. Sandalwood plantation’s surplus seeds could be used for their oil content, to improve the commercial viability of this industry. The seed oils were obtained by solvent extraction and supercritical carbon dioxide extraction respectively. Important physicochemical parameters were compared with other oils commonly used in pharmaceutical and cosmetic products. Acid values were found to be higher (6.0–7.5 mg KOH/1 g oil) while peroxide values (6.7–9.0 mequiv/Kg) were lower than reported for other oils. Tocopherols were found to be lower than those usually reported for nut oils (α-tocopherol 1–3 mg/100 g; δ-tocopherol 2.2–5.7 mg/100 g), squalenes and phytosterols were found in considerable quantities. The fatty acid content consisted largely of ximenynic acid (35 %) and oleic acid (52 %). No oxidative derivatives of fatty acids were observed. Although there were statistically significant differences in some properties, the magnitude of these were insufficient to conclude there were any notable differences in the two oil extracts.