AOCS Phospholipid Division
Newsletter October 2007

Message from the Chair
Jonathan Maynes

As usual, those who were able to attend the annual AOCS meeting had the opportunity to renew acquaintances, make new friends, and become informed on the latest research. Adding to the events this year, we were joined by the Japanese Oil Chemists' Society. In this issue of the division newsletter you will find an overview of the technical sessions, and a summary of the phospholipid short course held prior to the convention.

I also invite you to review some of the latest research in lecithin as reflected in the papers on “Synthesis of Diphosphatidylglycerol” and “Ring trial validation of a method for the extraction of DNA from soy lecithins.” Speaking of ring trials, Spectral Services has adjudicated the use of 31P-NMR for analysis of lecithin for years, and has recently concluded a ring test of this method in Europe, a summary report of which is included in this newsletter. Also included are several articles from recent issues of inform magazine which may be of particular interest.

It is with sadness we note that Dr. David Wayne Yesair passed away on April 20, 2007. His contributions to the Phospholipid Division have been many, and we will miss his presence.

Moving forward, we are planning for another great meeting next year in Seattle, May 18-21, 2008. We are currently arranging speakers for the various sessions. If you would like to participate, please contact a division officer, or submit an application on-line in the AOCS web site.

May you continue to have a great year, and best of luck in all your efforts.

31P-NMR Round Robin Tests on Phospholipids
Bernd W. K. Diehl, Ph.D.

The goal of this Round Robin test was to demonstrate that the results of 31P-NMR analysis of phospholipids is independent of laboratory, NMR instrument manufacturer, NMR filed strength, and test material. Validation of the sample preparation method has been previously published and was not a part of this evaluation. Five different materials (native soy lecithin, 90% phosphtidylserine, DSPC, egg yolk lecithin, and 20% phosphtidylserine) were prepared for analysis by Spectral Services. Twenty one laboratories participated in the study: eleven industrial, seven academic, and three research institutes. Equipment included three different manufacturers and ten different probes. Six different field strengths were also tested.

Results: Twenty five of twenty nine NMR units were able to analyze the five different materials to within a variation of 1%. Reasons for some of the failures included incorrect parameter and decoupler settings, and insufficient instrument tuning. Within the scope of statistical deviations, results were independent of the laboratory and material analyzed. The number of units from different manufacturers was too low to determine significance, and some errors in field strength results were dependent upon the signal/noise ratio.

Ring trial validation of a method for the extraction of DNA from soy lecithins
Authors - Waiblinger, H. U.; Ernst, B.; Graf, N.; Pietsch, K.

Abstract: Validation of a DNA extraction method for use in identification of GMO and derived products is described. Practical LOD (limit of detection) was used as a key tool for assessing suitability of the extraction method for subsequent real-time PCR quantification. In a ring trial (12 laboratories) involving DNA extraction from soy lecithins, satisfactory results with practical LOD of <0.9 % were achieved in 4 of the 5 soy lecithin samples examined. In-house tests showed that this protocol, in a slightly extended version, could also be used to extract DNA from cold pressed rapeseed oils.

Journal fuer Verbraucherschutz und Lebensmittelsicherheit/Journal of Consumer Protection and Food Safety 2007 (2):113-115

In Memoriam
 published in inform August 2007

Former AOCS member David W. Yesair died in Byfield, Massachusetts (USA) on April 20, 2007, at the age of 73. Yesair received his Ph.D. in biochemistry/organic chemistry/cellular biology from Cornell University, Ithaca, New York in 1958 and after several post-doctoral appointments worked for Arthur D. Little, Inc. from 1962 to 1984. In his final five years there he was vice president, but he then left to found BioMolecular Products (BMP). BMP is best known for its lipid complex Lym-X-Sorb, a formulation that enables fat and medicine, for example, to be absorbed directly into the body from the intestines and into the lymphatic system. He was a charter member of the International Society for the Study of Xenobiotics and the International Lecithin and Phospholipid Society. He received 10 U.S. patents and over 100 world patents and had more than 120 publications.

Results of AOCS Lecithin Short Course Québec 2007
Willem van Nieuwenhuyzen

The Lecithin Short Course met its expectations and budget. The short course was attended by 31 paying participants, 7 instructors and organizers, and 6 MSc students of Laval University as demonstrators in the labs and pilot plant.

5 registrants came from Canada, 9 from the USA, 3 from Latin America, 9 from Europe, and 5 from Asia. Most worked for companies. During the last afternoon, participants were asked to fill in an enquiry form with their judgment about the course. We got a 60% response rate.

Some findings:

Conclusion

A number of remarks are useful for further short courses. However a short course should be pre-competitive. Therefore we cannot handle all proprietary lecithin processing details and specific food application with specific lecithin types. And interests of participants is scattered.

A number of program suggestions may have been fulfilled by attending papers at the 4 Phospholipid sessions during the AOCS Annual Meeting.

It was not that easy to achieve full balance between the oral presentations and the lab demonstrations. The Laval-INAF professors Joseph Arul and Paul Angers stimulated their MSc students to train lecithin emulsification test and emulsion procedures. The students did marvelous jobs in organizing the laboratory tours, making presentations in English language (most students usually speak French) and answering questions. The number of enquiries and discussions during the presentations and the demonstrations was adequate.

Personally I was very pleased to organize this short course and I got a lot of positive remarks.

Synthesis of 1,3- and 1,2-Diphosphatidylglycerol

Moghis U. Ahmad, U. Murali Krishna, Shoukath M. Ali, Sreeti Choudhury, Imran Ahmad. Lipids (2007) 42:291-296

Abstract A novel phosphonium salt methodology was utilized for the first time to synthesize 1,3- and 1,2-diphosphatidylglycerol. Optically active 1,2-di-O-acyl-sn-glyceryl phosphate was coupled with unprotected glycerol in the presence of pyridiniumbromide perbromide and triethylamine to yield, after final removal of the phosphate protecting group, the title compounds. The 1,2-diphosphatidylglycerol (1,2-isomer of cardilipin) may be a member of a new class of phospholipids for industrial applications similar to other phosphocholines.

(Read full text online in PDF format)

Technical Program 2007

This year we were well represented in the technical program. We have always been known for our quality sessions in the past that inform the general audiences of the latest research in phospholipid-related topics. We had a total of four oral sessions with 29 papers presented, and a poster presentation with eight posters.

On Monday, Moghis Ahmad and Joe Casey chaired two sessions on Ether lipids. The sessions featuring such papers as “The Ether Lipid Deficient Mouse: Tracking Down Plasmologens,” and “Rx of Cancer using Ether Lipid,” showing the latest in research in this important area. Also on Monday, at the Phospholipid Luncheon, the Best Paper Award was presented along with the accompanying paper. This year it was “Comparative Evaluation of the Emulsifying Properties of Phospatidylcholine after Enzymatic Acyl Modification.” The paper was presented by Anders Vikbjerg.

Anders Vikbjerg.

Anders Vikbjerg presents his award-winning paper at the AOCS Annual Meeting.

Tuesday’s session was chaired by Willem van Nieuwenhuyzen and O. Shibata Kyushu on Specialty Phospholipids. The session included papers such as “Modification Processes of Lecithin,” and “Oxidative Stability and Emulsification properties of Egg Yolk Lecithin.” The session featured the some of the latest work in the area of specialty lecithin.

Wednesday’s session concluded our sessions. The session was chaired by Berndt Diehl and covered general topics in phospholipids. Some of the highlights of the session were the papers “Heat Deterioration of Phosholipids. III” and “Phosphatidylserine May Recover Neuronal Membrane Function of Aged Rat Brain Leading to Recovering the Activity of Neurotrophin Receptors and Choline Acetyltransferase.”

All in all the program went very well. We look forward to next year’s program which will include the following sessions:

Patent Applications: Enzymatic modification of lecithin
published in inform July 2007

Schmitt, H. and Heirman, M., Cargill, Inc., Wayzata, Minnesota, USA, 3/13/2007, US7189544

The disclosure pertains to enzymatic modification of lecithin and to hydrolyzed lecithin products obtained by such modification. One particular implementation provides methods for producing a hydrolyzed lecithin product containing hydrolyzed phospholipids, monoglycerides, and diglycerides. For example, such a method may include the steps of: (a) contacting a lecithin material, which includes a phospholipid component and a triglyceride component, in an aqueous or organic solvent medium, with a first enzyme effective to hydrolyze the phospholipid and (b) subsequently contacting the product of step (a) with a second enzyme, effective to hydrolyze the triglyceride under reaction conditions effective to inhibit esterification of the hydrolyzed phospholipid with released fatty acids.

Extracts and Distillates: Phospholipid species analysis
published in inform July 2007

Bang, D.Y., E.J. Ahn, and M.H. Moon, Shotgun Analysis of Phospholipids from Mouse Liver and Brain by Nanoflow Liquid Chromatography/Tandem Mass Spectrometry, J. Chromatogr. B 852:268–277, 2007.

Phospholipid (PL) species were determined using nanoflow reversed phase liquid chromatography/electrospray ionization tandem mass spectrometry (LC-ESI-MS-MS). A dual scan method was introduced for the high throughput analysis of complex PL mixtures. Two consecutive LC-ESI-MS-MS runs were made in positive ion mode for phosphatidylcholines (PC) and phosphatidyl-ethanolamines (PE) first followed by analysis in the negative ion mode for phosphatidylserines (PS) and phosphatidylinositols (PI) using the same binary gradient elution with and without formic acid, respectively. The MS analysis of the eluted PL molecules was performed with a precursor scan followed by a data dependent MS-MS scan. Identification was made of 90 and 60 PL species present in mouse liver and mouse brain, respectively.

Business News: Tight oilseed/oil markets forecast
published in inform August 2007

Global oilseed production has been forecast to decline for the season 2007/08, although the production of oils and fats is seen as improving significantly. These generalizations were made in the World Agricultural Supply and Demand Estimates report numbered WASDE-447-3 and issued on June 11 by the U.S. Department of Agriculture (USDA) (netlink: www.ussoyexports.org/resources/wasde-06-11-2007.pdf), and in a commentary published in the June 22 issue of Oil World.

Global oilseed production for 2007/08 is projected at 399 million metric tons (MMT) down by approximately 4 MMT from 2006/07, the first possible year-to-year decline since 1995/96. A projected oilseed production from non-United States sources at 315 MMT, would equate to an increase of 7 MMT over the previous season, inferring a significant drop in production in the United States.

Oil World attributes the global production deficit in 2007/08 to tightness in wheat and corn in the current season and sharply higher grain prices that have seen a shift in planting acreage away from oilseeds in the United States, Argentina, China, and some other countries. Unfavorable weather is also noted as a contributing factor, and one that may have a definite impact on any forecasts for the 2007/08 season. Concerns exist that, if La Niña develops, drier conditions will prevail in the U.S. Midwest with a negative impact on crop yields. The situation is further compromised with expectations that global demand for oilseeds is expected to rise by 14 MMT to 410 MMT against the forecast production of 399 MMT, resulting in a sharp depletion of stocks.

Globally, soybean production is projected to decrease in 2007/08 by approximately 10 MMT to 225–228 MMT due to predicted lower plantings and projected production of only 77.6 MMT in the United States that could be further subjected to unfavorable weather conditions associated with La Niña. This situation would be the first decline in world soybean production in four years, but is tempered by expectations of increased productions to record highs in Brazil and Argentina owing to increased plantings. Consumption of soybeans worldwide is seen to exceed production in 2007/08 by 10 MMT, leading to a corresponding decline in stocks.

Global production of rapeseed (including canola) in 2007/08 is seen at 51.6 MMT, up 4.4 MMT from 2006/07, reflecting increased plantings, but lower than anticipated due to weather problems in Europe and China. Higher productions are forecast for Canada, India, and Australia. The lower global sunflower seed production at a three-year low of 30.6 MMT for 2007/08 is seen as a consequence of smaller crops projected for EU-27 and Ukraine. Cottonseed is set globally to decline by 0.6 MMT to 43.3 MMT in 2007/08 owing to reduced plantings and lower production in Russia, Brazil, China, Turkey, and Australia. A recovery of 0.9 MMT is forecast for peanut (groundnut) output to 23.8 MMT, but the crop is seen as being in difficulties in the United States because of dry conditions in the state of Georgia.

Vegetable oil production is projected to increase 5.3% in 2007/08 to 160.2 MMT, led by increases for China, India, and EU-27, but consumption is expected to keep pace at 160.5 MMT. The increased consumption in EU-27 mostly reflects increased production of biodiesel. The contribution of palm oil to the production of vegetable oils, which is forecast for 2008 at 41.8 MMT, up from 38.5 MMT in 2007, shows a slowing growth rate. Global vegetable oil stocks, however, are projected to decline 6% for 2006/07.