ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

PHOSPHOLIPID
PHO 1: Phospholipids and Bioactive Lipids in Foods and Pharmaceutical Applications
Chairs: Ernesto Hernandez, Advanced Lipid Consultants, USA; and Samia Mezouari, Research &
Consulting, Canada

Bioactive Lipids Yeonhwa Park*, Dept. of Food need for high stability oils. The oil is high in oleic
Science, University of Massachusetts Amherst, acid and low in polyunsaturated fatty acids
USA making it as stable as partially hydrogenated
Lipids are primarily known for its basic oils but without the trans fat. In addition to the
functions of energy reservoir as well as its intended changes in the oil, we have found that
structural components of cell membranes. both the protein and lecithin fractions from
However, many biologically significant functions high oleic soybeans have improved functional
have been discovered from ‘bioactive lipids’ characteristics. The lecithin has an altered
from the basic cell biology to even cancer. Many composition reflecting the oil profile and
research studies on bioactive lipids focus on the functions more effectively as an antioxidant.
functions of fatty acids, such as n-3 fatty acids High oleic soybean lecithin offers the potential
or conjugated linoleic acid, but bioactive lipids for a natural, clean-label, antioxidant and pan
also include ceramide, diacylglycerol, release agent.
eicosanoids, steroid hormones, and
phosphatidic acid. Lipid soluble components Long-Chain Omega-3 Status in Canadian
including lipid-soluble vitamins and Adults: Results from the Canadian Health
phytochemicals also contribute to improvement Measures Survey 2012-2015 Isabelle
of health. Overview of functions of bioactive Demonty*1, Kellie Langlois2, Linda Greene-
lipids in the biological system, along with its Finestone3, Rana Zoka4, and Loan
sources and potential application of these Nguyen5,1Nutrition Research Division, Bureau of
bioactive lipids to functional food product, will Nutritional Sciences, Health Canada, Canada;
be presented. 2
Health Analysis Division, Statistics Canada,
Canada; 3Public Health Agency of Canada,
Superior Antioxidant Activity of Lecithin Canada; 4Bureau of Nutritional Sciences, Food
Derived from High Oleic Soybeans Susan Directorate, HPFB, Health Canada, Canada;
Knowlton*, DuPont Company, Pioneer, USA 5
Bureau of Food Surveillance and Science
Lecithin is a byproduct of vegetable oil Integration, Food Directorate, HPFB, Health
processing and is removed during the Canada, Canada
degumming step as a mixture of phospholipids Objective: The sum of eicosapentaenoic
in oil. It is valued for its emulsification acid (EPA) and docosahexaenoic acid (DHA) in
properties and is used in a wide variety of red blood cell (RBC) membranes (Omega-3
applications, particularly in foods. Lecithin Index) reflects long-term dietary intake and has
derived from soybeans is the major form of been proposed as a marker of coronary heart
lecithin on the market today although disease (CHD) risk. We aimed at characterizing
sunflower lecithin is gaining share because of its the Canadian population subgroups that have
status as a non-GMO crop. High oleic soybeans the lowest Omega-3 Index and may benefit
are growing in popularity because the oil brings from increased long-chain omega-3 intake.
a soy-based solution for the food industry’s

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

Methods: Data from the Canadian Health level. The art of combining various active
Measures Survey Cycles 3-4, obtained from ingredients is in the optimal concentration
4025 adults aged 20-79y, were pooled. ratios, complemented with suitable aiding
Adjusted mean RBC levels of EPA, DHA, Omega- agents. At the same time, neither ingredients
3 Index, other omega-3s, total omega-6, and nor aiding agents should affect the flavor, odor
ratios were calculated for different population or color of the final application. In order to
subgroups using multiple linear regression. meet this challenge, we have formulated
synergistic antioxidant management solutions
Results: Only Omega-3 Index results are
using highly potent rosemary extract solutions,
summarised here. Females had a higher Index
tocopherols and ascorbyl palmitate, while
(4.59) than males (4.44) (P<0.05), but <3% of
phospholipid lecithin was added as a support
females and 1% of males had an Index ≥8
system. Results showed that lecithin
(associated with low CHD risk). The Index was
outperforms other tested agents in providing
higher in older adults; those 60-79y had the
formulations of premium quality in terms of
highest Index (4.96), and those 20-39y, the
better solubility, lower viscosity and absence of
lowest (4.29). Fish intake, omega-3 supplement
precipitation products. Moreover, lecithin
use, and race were the characteristics the most
showed to be an essential ingredient in
strongly associated with Index scores. The Index
dissolving higher concentrations of ascorbyl
was significantly higher in participants
palmitate. Such synergistic formulations
consuming fish ≥2 times/week (including ≥1 oily
exhibited better efficiency in ensuring oxidative
fish) (5.56) versus those consuming less fish
protection of final applications, especially
(4.37), in participants taking supplements (5.69)
various oils (vegetable oils, fish oils, omega – 3
versus those not taking any (4.39), and in Asians
oils) and edible fats (animal fats, margarines
(5.28) or other (pooled) ethnic groups (4.79)
and mayonnaises), where they provided up to
versus Whites (4.36) (all P<0.001).
6-fold better oxidative stability of the tested
Conclusions: Despite moderate differences samples as indicated using rancimat method. At
between subgroups, most adults have a low the same time, 40% higher antioxidant
Omega-3 Index. Nutrition communication efficiency was achieved in comparison to
messages aimed at increasing long-chain formulations without ascorbyl palmitate and
omega-3 intake should target the majority of lecithin. In conclusion, obtained results indicate
Canadians. that phospholipid lecithin has an important role
in formulating synergistic antioxidant solutions
and that it contributes to efficient oxidative
Lecithin as a Support System of Various protection of various food products.
Antioxidant Management Solutions Dushka
Dimitrijevic*1, Ksenija Uroic, Simona Urbancic, Achieving a Tumor Docosahexaenoic Acid
Masa Hojnik Niderl2, Karmen Plajnsek, and Nina (DHA) Content of 5% from Different Doses and
Janzekovic2, 1Frutarom IFF, Slovenia; 2Food Sources of DHA Improved Chemotherapy
Protection BU of Frutarom-IFF, Slovenia Efficacy in Mice Bearing Patient Derived Breast
Certain sensitive food applications, that are Cancer Xenografts Marnie Newell*, Vera
highly susceptible to oxidation and degradation Mazurak, Lynne M. Postovit, and Catherine J.
processes due to their nature and composition, Field, University of Alberta, Canada
require application of different antioxidant Docosahexaenoic acid (DHA) has been
systems in order to protect them at adequate shown to reduce breast cancer (BC) cell growth

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

of immortalized cell lines in vitro and when sphingomyelin (> 30%), however, in infant
implanted in rodents but not in more formula is phosphatidylcholine. The structure of
representative heterogeneic models. We sought phospholipid on MFGM was investigated using
to determine if DHA would elicit an anti-tumor CLSM and TEM. The mean diameter of fat
effect on patient derived xenografts (PDX) and if globules (~200 nm) in infant formula was
different dietary doses (high DHA, algal source significantly smaller than human milk fat
and low DHA, canola source) would elicit similar globules (~ 5 μm). In breast milk, the
responses. Female NSG mice bearing BC PDX phospholipids are evenly coverage on the
tumors (100 mm3) were randomized to one of triacylglycerols, while, the phospholipids in
three nutritionally adequate high fat diets (20% infant formula tend to aggregate. The MFGM
w/w ±DHA). Treatment paradigms included a) were observed by CLSM labeled by multi-
0% dietary DHA b) 0% DHA + TXT (docetaxel fluorescent probes. Moreover, a stable oil-in-
5mg/kg) c) 4% DHA (algal source) + TXT and d) water emulsion with large size fat globules
2% DHA (DHA canola oil) + TXT. After 6 wks of stabilizing by nanoscale protein droplets was
chemotherapy, tumors were excised, weighed prepared. Further study on the effect of the
and the phospholipid (PL) composition unique architecture of MFGM on infant’s lipid
determined. Feeding 2% or 4% DHA decreased metabolism are needed to fill the gaps in the
tumor growth compared to 0% DHA±TXT (P knowledge of phospholipid supplemented in
infant formula.
Composition and Structure of Human Milk Fat
Globules: Towards Specific Interest in Infant Use of New Phospholipid Blends for
Formula Wei Wei*1, Mingdong Dong2, and Stabilization and Delivery of Bioactives in
Xingguo Wang1,1Jiangnan University, China; Beverages Ernesto M. Hernandez*, Advanced
2
Interdisciplinary Nanoscience Center, Aarhus Lipid Consultants, USA
University, Denmark Phospholipids are widely utilized as natural
Human breast milk is an oil-in-water emulsifiers, wetting, and dispersing agents in
emulsion comprising fat droplets stabilized by a food as well as in many cosmetic and
complex tri-layer membrane. The surface of the pharmaceutical applications. Phospholipids are
milk fat globule membrane (MFGM) includes a also widely used in several emulsion systems
variety of components (mainly polar lipids, because of their tendency to form structures
proteins, neutral lipids, etc.). In recent years, such as bilayers, micelles, and liposomes. This
this unique physical structure of MFGM are has resulted in the development of new
receiving increasing interests due to its supplements and pharmaceutical products for
nutritional effects on lipid digestion and brain the targeted delivery of some drugs and
development of infants. In our recent study, we specialized nutrients. Applications of
determined the composition and structure of phospholipids have also extended into more
phospholipid in Chinese breast milk of different specialized areas such as emulsion stabilization
gestational age and lactation stages and infant and a more efficient digestive delivery of
formulas from the Chinese market. nutrients such as essential fatty acids, and other
Phospholipids composition were analyzed by lipids-soluble bioactives. This presentation will
31P NMR and UPLC-MS/MS (Q-ToF). Results include the use of modified blends of soybean,
revealed that the infant formulas have much canola and sunflower phospholipids in the
higher phospholipid than breast milk. The preparation of emulsions for the delivery of
highest content of phospholipid in breast milk is omega 3 fatty acids and other bioactive lipids in

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

beverages. These oil-in-water emulsions were analyzed for emulsion stability, organoleptic
manufactured using modified blends of shelf life and absorption rate of bioactives.
soybean, canola sand sunflower lecithins, mono Results showed that these new lecithin blends
and diglycerides, and modified sugars. The main are able to prevent creaming, coalescing and oil
objectives of using these new emulsions are to phase precipitation in the emulsion by
stabilize the suspended emulsion particles by balancing the specific gravity of the oil phase
preventing creaming, coalescing and versus that of the water phase and also increase
precipitation of the suspended globules and the bioavailabilty of the bioactives by the
increase the bio availability of nutrients. The combination of phospholipids and modified
methods of emulsion preparation included high sugars.
shear mixing and high pressure
homogenization. The resulting emulsions were

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

PHO 2: New Trends in Lecithin Process, Modification and Applications

Chairs: Moghis Ahmad, Jina Pharmaceuticals Inc., USA; and Swapnil Jadhav, Archer Daniels Midland Co.,
USA

Polar Lipids: Potentiality for Exploration could address multi-function demands in

Xuebing Xu*,Wilmar Global Research and different fields. Starting with mariane
Development Center, China phospholipids, we developed an entirely green
Polar lipids exist in nature in small process for enzymatic production of lyso-
percentage but with large variety. Those large phosphatidylcholine. A few liquid lipases are
varieties have played various functions in life screened for ethanolysis of purified
such as cell structure, delivery system, etc. Polar phosphatidylcholine (PC), TLC-FID and GC-FID
lipids play a big role in nutrigenomics in recent detections were used to monitor reaction
studies. This has brought interesting discussions progress and examine fatty acid compositions
on polar lipids in nutritional and pharmaceutical of different product fractions. Lipase NS-40116
applications. With the targeted understanding from a genetic C. antarctica lipase A (CAL-A)
and possibilities in various applications, the displayed the best performance in either yield
tailor making of polar lipids through of lyso-PC and n-3 PUFA enrichment. Critical
modifications and syntheses have been parameters, such as ethanol:PC ratio, reaction
received attentions, particularly with the time and temperature, water content, and
progress of biotechnology. The artificial polar enzyme dosage are optimized. The results
lipids have been explored for synthesis and showed that, under optimized conditions
applications in targeted cases. In general, for a through just one step-process, the yield of lyso-
lipid structure with various hydrophobic groups PC is up to 85% and the total n-3 PUFAs
in various chemical structures and a hydrophilic enriched up to 90% and DHA up to 75% in lyso-
group with the similar structural possibilities, a PC fraction. 1H/13C NMR analyses were used to
functional property can be tailor-made for illustrate the reaction mechanism, which
various possibilities. This possibility can be verified that the non-regioselectivity and high
learnt from natural polar lipids. The general non-hydrolytic property towards long chain
possibilities will be discussed in this PUFAs of CAL-A are the main character to drive
presentation. A few case studies will be this high efficiency and high selective process.
illustrated also.
Production and Applications of New Structured
Enzymatic Production of Marine Based Lyso- Phospholipids with Omega 7, Palmitoleic Fatty
phosphatidylcholine Enriched in ω-3 acid. Ernesto M. Hernandez*, Advanced Lipid
Polyunsaturated Fatty Acids Bo Zhou1, Consultants, USA
Sampson Anankanbil2, Yongjin He1, and Zheng Palmitoleic acid (PA) is now widely
Guo*1,1Aarhus University, Denmark; 2Dept. of marketed as a supplement and reported to
Engineering, Aarhus University, Denmark have protective effects against some cardio
Lyso-phospholipids enriched in n-3 vascular disease risk factors. PA rich foods (i.e.,
polyunsaturated fatty acids have both macadamia nuts, buckthorn seeds, and some
surface/interface-active functionality and fish oils) have been found to significantly lower
health-beneficial fragments such levels of CRP (a measure of inflammation in the
eicosapentaenoic acid (EPA, C20:5ω-3) and body), triglycerides, and LDL ("bad")
docosahexaenoic acid (DHA, C22:6ω-3); which cholesterol, while increasing HDL ("good")

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

cholesterol. A recently patented process also utilized by-product of skim milk and anhydrous
shows that interesterifying PA to phospholipids milk fat production that is currently being
results in a product that can have superior discarded by the dairy industry. This product
bioactivity than the triglyceride version. In this contains a higher concentration of PLs and
research we synthesized and concentrated PA- MFGM proteins but an economically feasible
ethyl esters from macadamia oil and then processing method to obtain these valuable
interesterified them into phospholipids using components has yet to be obtained. Zinc
immobilized enzymes. We investigated the use acetate and calcium acetate along with mild
of different lipases and phospholipases, at heat treatment and pH adjustment have been
different reaction times and temperature shown to precipitate PLs and proteins into a
parameters to study the effect on the yield of pellet. This method has great potential to
the structured phospholipids. In a typical produce an isolated lipid fraction rich in PLs, as
reaction, lecithin was mixed with palmitoleic well as an enriched MFGM protein product
acid rich ethyl esters and immobilized lipase (or when used in tandem with an ethanol
phospholipase) was added to the reaction extraction (90% ethanol at 70°C). The optimum
mixture and the interesterification reaction was precipitation treatments that were identified
carried out at 40 -60 C. Enzymes Lipozyme TLIM for the beta stream were zinc acetate at 25 mM
and Phospholipase A2 were used. After the concentration at pH of 7.5 and temperature of
reaction was completed the immobilized 30°C and calcium acetate at 100 mM
enzyme was filtered off and the lecithin- oil concentration at pH of 7.5 and temperature of
mixture was solvent and water washed to 60°C. The novel use of ethanol extraction was
separate the phospholipid fraction. The shown to be an effective way to remove the
phospholipid fraction was dried in a vacuum lipid from the precipitated pellet with a PL
oven and analyzed for palmitoleic acid recovery of 97.7% for zinc acetate and 94.9%
incorporation. We were able to incorporate for calcium acetate under the optimum
more than 40% palmitoleic acid into the precipitation treatments.
phospholipid fraction. The structured
phospholipid was also tested for emulsifying Lecithin: The Role in Compounds (Coating,
properties for use in food and beverage Filling), Does the Source Matter? Donna C.
products. Studenka*, Bunge Loders Croklaan, USA
Abstract not available.
Application of Zinc and Calcium Acetate to
Precipitate Milk Fat Globule Membrane Double-Layer Chia Oil Microcapsules with
Components from a Dairy By-product Tao Fei, Sunflower Lysolecithin and Maltodextrin-Chia
Stephanie Clark, Tong Wang, and Nathan R. Mucilage Mabel Tomás*, CIDCA (CONICET-
Price*, Iowa State University, USA UNLP), Argentina
There has been a great interest in Lysolecithin obtained after enzymatic
developing isolated dairy lipid fractions that are phospholipid hydrolysis exhibits interesting
rich in phospholipids (PLs) due to their health applications in foods. In this regard, has been
and functional properties. There is also great reported that hydrolyzed sunflower lecithin
potential to utilize dairy by-products that are (HSL) presents enhanced functional properties
currently being discarded due to their elevated over native ones. On the other hand, the use of
content of PLs and milk fat globular membrane biopolymer combinations to improve their
(MFGM) proteins. The beta stream is an under- individual characteristics associated with the

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

retention and protection of microencapsulated spectral overlap and low isotopic abundance,
active compounds such as omega-3 rich oils respectively. However, 31P NMR spectroscopy
constitutes a challenge. In this context, double- was shown to be particularly powerful, due in
layer chia oil (~64 % ALA) emulsions 5:95 wt/wt part to the 100% isotopic abundance of the 31P
were prepared through the electrostatic nucleus. Further, each unique phospholipid
deposition of chitosan (cationic character) onto contains a single phosphorus atom, thus greatly
hydrolyzed sunflower lecithin (anionic simplifying spectral interpretation. Since this
character) coated droplets (pH 3), discovery, 31P NMR spectroscopy has been used
microfluidization at 1000 bar with the addition for both qualitative and quantitative
of maltodextrin (Mx) or maltodextrin: chia determination of phospholipids in foods
mucilage (Mx: CM 90:10) as structural containing lecithin, including egg, wheat germ,
materials. The double-layer microcapsules were soy, milk, meats and other naturally-derived
obtained by spray-drying of these emulsions phospholipid sources such as krill oil. This
with an efficiency of ~ 97%. The powder presentation will detail the history of
characterization resulted in aw and moisture phospholipid analysis by 31P NMR spectroscopy:
contents of ~0.21-0.24 and ~1.45-1.99%, where we’ve been, where we are, and where
respectively. The use of the Mx: CM we are headed in the future. A wide variety of
combination led to an increase of the D3,2 examples will be presented, with a particular
value (0.15 from 7.25 µm) and a decrease on focus on the advantages of the 31P NMR
the ζ potential (+43 to +38). Additionally, the method, advancements in automated analysis
color parameters resulted in 94.9 and 91.8, -0.1 protocols and multivariate analysis of the
and +0.1, 7.9 and 7.7 for L*, a* and b*, resulting data.
respectively. The use of HSL as emulsifying
agent and the combination of biopolymers Mx-
CM would be efficient in the development of
chia oil multilayer microcapsules.

Forty Years of 31P NMR Spectroscopy of

Phospholipids Kristie Adams*1, and Bernd W.K
Diehl2, 1Steelyard Analytics, Inc., USA; 2Spectral
Service AG, Germany
The power of NMR spectroscopy for
studying phospholipids was first demonstrated
in the 1970s. These early studies showed that
1
H and 13C NMR spectroscopies had limited
applicability for the study of mixtures of
phospholipids, due to excessive amounts of

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ABSTRACTS 2019 AOCS ANNUAL MEETING & EXPO May 5–8, 2019

PHO-P: Phospholipid Poster Session

Chairs: Shawn Pan, Bunge North America, USA; and Sheher Mohsin, Agilent, USA

Retardation of Anhydrous Milk Fat

Crystallization through the Addition of Dairy
Phospholipids Zachary Cooper*1, Casey R.
Simons2, and Silvana Martini1,1Utah State
University, USA; 2Utah State University, United
States
The objective of this study was to evaluate
the effect of milk phospholipids (PL) on the
crystallization of anhydrous milk fat (AMF). PL
were isolated from a phospholipid concentrate
powder. Three mixtures of PL in AMF (0%,
0.01%, and 0.1%) were made. Samples were
crystallized for 90 min at 24, 26, and 28°C. The
solid fat content was measured as a function of
time and fitted to the Avrami equation. Melting
point, thermal behavior, viscoelastic properties,
and crystal morphology were measured at 90
min and after storage at 5°C for 48 h. PL slowed
crystallization as concentration increased and
this effect was more pronounced at higher
temperatures with no crystallization observed
for the 0.1% PL at 28°C. The addition of PL
resulted in bigger crystals. PL reduced G’ values
at 90 min for samples crystallized at 24 and
26°C with G’ values of 1.8x106±3.0x104 Pa,
7.1x104±2.1x104 Pa respectively for the AMF
and G’ values of 2.1x104±1.1x104 Pa and
1.4x104±1.0x104 Pa for the 0.1% PL and
8.5x104±2.9x104 Pa and 9.1x104±2.1x104 Pa for
the 0.01% PL. Similarly, hardness decreased
from 20.10±1.13 N for AMF at 24 and 26°C to
15.06±0.77 N for 0.01% at 24 and 26°C and
0.1% at 24°C, but an increase occurred for 0.1%
at 26°C 25.62±1.98 N. The delay in
crystallization caused by PL was also evidenced
by lower enthalpy values.

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