Defatted seedmeals from 15 glucosinolate-containing plant species were analyzed for herbicidal activity by determining inhibition of seedling emergence when added to a sandy loam soil containing wheat and sicklepod seeds at concentrations of 0.1, 0.5, and 1% (w/w). In general, the seedmeals were more phytotoxic to wheat than sicklepod. For wheat, all of the seedmeals significantly inhibited seedling emergence at the 1.0% concentration. At the 0.1% concentration three of the seedmeals (Indian mustard, money plant, and field pennycress) completely inhibited wheat emergence. For sicklepod emergence, eight of the seedmeals were completely inhibitory at the 1% level (Indian mustard, field pennycress, garden rocket, Siberian wallflower, English wallflower, garden cress, sweet alyssum, and evening stock) and four were completely inhibitory at the 0.5% level (brown mustard, garden rocket, English wallflower, and sweet alyssum). Intact glucosinolates and their corresponding hydrolysis products varied among the seedmeals with the highest activity. Major hydrolysis products produced by the seedmeals with the most phytotoxicity, respectively, included 2-propenyl (allyl) isothiocyanate (AITC) by brown mustard seedmeal, allyl thiocyanate and AITC by field pennycress seedmeal, erucin (4-methylthiobutyl isothiocyanate) by arugula seedmeal, 3-butenyl isothiocyanate and lesquerellin (6-methylthiohexyl isothiocyanate) by sweet alyssum seedmeal, and isopropyl isothiocyanate by money plant seedmeal. From our data it appears that both the type and concentration of glucosinolates and their hydrolysis products present in the seedmeals affect seed-emergence inhibition.

The effect of dietary docosahexaenoic acid (22:6n-3, DHA) on the metabolism of oleic, linoleic, and linolenic acids was investigated in male subjects (n = 6) confined to a metabolic unit and fed diets containing 6.5 or <0.1 g/d of DHA for 90 d. At the end of the diet period, the subjects were fed a mixture of deuterated triglycerides containing 18:1n-9[d6], 18:2n-6[d2], and 18:3n-3[d4]. Blood samples were drawn at 0, 2, 4, 6, 8, 12, 24, 48, and 72 h. Methyl esters of plasma total lipids, triglycerides, phospholipids, and cholesterol esters were analyzed by gas chromatography-mass spectrometry. Chylomicron triglyceride results show that the deuterated fatty acids were equally well absorbed and diet did not influence absorption. Compared to the low-DHA diet (LO-DHA), clearance of the labeled fatty acids from chylomicron triglycerides was modestly higher for subjects fed the high DHA diet (HI-DHA). DHA supplementation significantly reduced the concentrations of most n-6[d2] and n-3[d4] long-chain fatty acid (LCFA) metabolites in plasma lipids. Accumulation of 20:5n-3[d4] and 22:6n-3[d4] was depressed by 76 and 88%, respectively. Accumulations of 20:3n-6[d2] and 20:4n-6[d2] were both decreased by 72%. No effect of diet was observed on acyltransferase selectivity or on uptake and clearance of 18:1n-9[d6], 18:2n-6[d2], and 18:3n-3[d4]. The results indicate that accumulation of n-3 LCFA metabolites synthesized from 18:3n-3 in typical U.S. diets would be reduced from about 120 to 30 mg/d by supplementation with 6.5 g/d of DHA. Accumulation of n-6 LCFA metabolites synthesized from 18:2n-6 in U.S. diets is estimated to be reduced from about 800 to 180 mg/d. This decrease is two to three times the amount of n-6 LCFA in a typical U.S. diet. These results support the hypothesis that health benefits associated with DHA supplementation are the combined result of reduced accretion of n-6 LCFA metabolites and an increase in n-3 LCFA levels in tissue lipids.

This paper deals with the reanalysis of serum lipids from previous studies in which deuterated fatty acids were administered to a single person. Samples were reanalyzed to determine if the deuterated fatty acids were converted to deuterium-labeled conjugated linoleic acid (CLA, 9c,11t-18:2) or other CLA isomers. We found 11-trans-octadecenoate (fed as the triglyceride) was converted (delta9 desaturase) to CLA, at a CLA enrichment of ca. 30%. The 11-cis-octadecenoate isomer was also converted to 9c,11c-18:2, but at <10% the concentration of the 11t-18:1 isomer. No evidence (within our limits of detection) for conversion of 10-cis- or 10-trans-octadecenoate to the 10,12-CLA isomers (delta12 desaturase) was found. No evidence for the conversion of 9-cis,12-cis-octadecadienoate to CLA (via isomerase enzyme) was found. Although these data come from four single human subject studies, data from some 30 similar human studies have convinced us that the existence of a metabolic pathway in one subject may be extrapolated to the normal adult population.

A combination of high-pressure extraction and preparative chromatography was used to purify the group A and group B soyasaponins from soy germ for use as analytical standards and for use in biological assays. A standardized sample preparation and extraction method was developed for the analysis of phytochemicals found in soy and processed soy products, which is reproducible in other laboratories. The extracts can be analyzed with standard liquid chromatography-mass spectrometry and high-performance liquid chromatography methods to identify and quantitate the group A and group B forms of the soy saponins, as well as the soy isoflavones. Complete saponin analysis of the extracts prepared from soy germ (hypocots), hulls, and cotyledons shows that a significant portion of the saponins is concentrated in the germ. The germ contains nearly all of the group A soyasaponins, while the group B soyasaponins are nearly equally distributed between the germ and the cotyledons. The hulls contain little of either isoflavones or saponins. Whole (full fat) soybeans grown on a tract in central Illinois in 2003 contain approximately 4-6% saponins on a weight basis, of which about one-fifth or less of the total saponin content are group A soyasaponins; the balance is group B soyasaponins.

Pure analytical standards for the major saponins present in processed soy products, the group B saponins (soyasaponins I, II, III and IV), were isolated in mg quantities by a combination of processing, precipitation/re-solubilisation, TLC and preparative HPLC. These standards were determined to be pure by LC-ESI/MS analysis and NMR. The standards were used to perfect a facile analytical HPLC method using spectrometric detection to determine the percent composition of the group B soyasaponins in various products from processing of soybean.