WO2022006711A1 - Procédé pour la préparation de lysophosphatidylinositol - Google Patents

Procédé pour la préparation de lysophosphatidylinositol Download PDF

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Publication number
WO2022006711A1
WO2022006711A1 PCT/CN2020/100444 CN2020100444W WO2022006711A1 WO 2022006711 A1 WO2022006711 A1 WO 2022006711A1 CN 2020100444 W CN2020100444 W CN 2020100444W WO 2022006711 A1 WO2022006711 A1 WO 2022006711A1
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Prior art keywords
lecithin
lpi
lysolecithin
weight
buffer
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PCT/CN2020/100444
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English (en)
Inventor
Zheng Li
Songying Li
Shengshi Huang
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Kemin Industries, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Kemin Industries, Inc. filed Critical Kemin Industries, Inc.
Priority to PCT/CN2020/100444 priority Critical patent/WO2022006711A1/fr
Priority to US17/235,561 priority patent/US20220002325A1/en
Priority to PCT/US2021/028184 priority patent/WO2022010559A1/fr
Priority to CN202180046187.7A priority patent/CN115867293A/zh
Publication of WO2022006711A1 publication Critical patent/WO2022006711A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6481—Phosphoglycerides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C12Y301/01032—Phospholipase A1 (3.1.1.32)

Definitions

  • lecithin is a family of phospholipids (PL) rich in phosphatidylcholine (PC) , phosphatidylinositol (PI) , phosphatidylethanolamine (PE) and phosphatidic acid (PA) (Fig. 1) . It is well known as a natural surfactant and widely used in food, feed and pharmaceutical industries. Commercial lecithins are usually extracted from soybean, rapeseed, sunflower seed and egg yolk. Lecithins of different resources not only vary in phospholipid type and its content, but also vary in the fatty acid profile at sn-1 and sn-2 position, which makes lecithin a very complex mixture. It is difficult to isolate high-purity phospholipid component, especially LPI from natural lecithin.
  • Lysoforte TM a lysolecithin-based product
  • LPC lysophosphatidylcholine
  • LPI Lysoforte -lysophosphatidylinositol
  • LPI can be synthesized from the partial hydrolysis of PI (Phosphatidylinositol) , a major phospholipid component in lecithin, via phospholipase A 1 or A 2 in an aqueous medium 2, 3, 4 .
  • PI Phosphatidylinositol
  • Most sources are focused on converting PC (Phosphatidylcholine) /PE (Phosphatidylethanolamine) to LPC/LPE (Lysophosphatidylethanolamine) , whereas little information on LPI conversion has been involved (Table 1) . It has also been found that LPI content in lysolecithin products is very low –less than 2.5%.
  • Kemin has developed different enzymatic hydrolysis methods for the production of lysolecithin.
  • the content of LPI in LCL is less than 2.5%and the conversion rate of PI to LPI is very low.
  • the present invention relates to the preparation of lysolecithin with high LPI content using an acetate or an ether as solvent.
  • a fast and effective work-up procedure was also developed to separate LPI products from the starting material simply by phase separation.
  • the method of the invention surprisingly provides enriched LPC, LPE and LPA content in the high-LPI lysolecithin product of the invention.
  • the lecithin with an organic solvent, a buffer or water, and a phospholipase to catalyze the hydrolysis of the phospholipids.
  • the lecithin is mixed with EtOAc, PBS buffer and PLA 1 for a period of time sufficient to hydrolyze the phospholipids, after which the resulting lysophospholipids are separated from the mixture then dried.
  • EtOAc EtOAc
  • PBS buffer PBS buffer
  • PLA 1 a period of time sufficient to hydrolyze the phospholipids
  • the LPI content achieved is higher than 13%while LPC content is likewise increased to greater than 15%.
  • the method of the invention is applicable to synthesis of high-LPI lysolecithin under pilot production conditions.
  • Figure 1 shows chemical structure of phospholipid components
  • Figure 2 shows equipment for pilot production of high-LPI lysolecithin in the plant
  • Figure 3 shows flow chart for the pilot production of high-LPI lysolecithin usingregular soy lecithin as the starting material
  • Figure 4 shows effects of reaction temperature on LPI content
  • Figure 5 shows effects of reaction time on LPI content
  • Figure 6 shows effects of ethyl acetate volume on LPI content
  • Figure 7 shows effects of PBS content on LPI content
  • Figure 8 shows influence of the four factors on LPI content using de-oiled lecithinas the starting material
  • Figure 9 shows the predicted highest LPI content (13.9%) under the suggestedconditions
  • Figure 10 shows LPI and LPC content in the repeating experiments under theoptimal conditions when de-oiled lecithin used as the starting material
  • Figure 11 shows the effects of PBS, Time, EtOAc and PLA on LPI content usingregular soy lecithin as the starting material
  • Figure 12 shows L
  • the invention relates to the high-LPI lysolecithin and the processes and methods related to the same.
  • the starting material is lecithin (phosphatidylcholine) and all sources thereof including, but not limited to, soy, sunflower, corn, rapeseed, peanuts, organ meats, red meats, whole eggs, whole milk with cream, spinach, cauliflower, oranges, wheat germ, fish, dairy cream, and liver, .
  • the appearance of starting material can also be at various forms thereof including, but not limited to liquid, solid, syrup, slurry and paste.
  • the sources of lecithin are deoiled lecithin and soy lecithin.
  • the invention is also intended to include other potential natural and synthetic sources of lecithin.
  • the lecithin is first mixed with a solvent, a buffer, and a phospholipase to catalyze the hydrolysis of the phospholipid.
  • the solvent is one capable of at least partially dissolving the lecithin.
  • solvents are well known in the art and include, but are not limited to, methanol, ethanol, acetonitrile, acetone, and ethers and acetates such as diethyl ether, ethyl ether, methyl tert-butyl ether, methyl t-butyl ether (MTBE) , isopropyl acetate and ethyl acetate (EtOAc) .
  • the solvent is EtOAc.
  • the solvent should be included in an amount of at least about 100%volume of solvent to lecithin weight. In one embodiment, the solvent is included in a range of about 500-1200%volume of solvent to lecithin weight, with about 400-600%volume of solvent to lecithin weight being preferred.
  • buffers as well as deionized water are appropriate for use in the invention include, but are not limited to, phosphate buffered solution (PBS) , modified PBS buffers, borate buffers, Hepes and othe Good’s buffers, alkaline buffers such as carbonate buffers and Tris-based buffers, and acidic buffers such as citrate buffers.
  • PBS phosphate buffered solution
  • the buffer is PBS.
  • the buffer is included in an amount of at least about 1%by weight buffer to lecithin weight.
  • the buffer is included in a range of about 20-120%weight of buffer to lecithin weight, with about 30-80%weight of buffer to lecithin weight being preferred.
  • the phospholipase of the invention may be any phospholipase capable of cleaving the lecithin molecule into fatty acid and other lipophilic substances, which is generally phospholipase A 1 or phospholipase A 2 .
  • the phospholipase is phospholipase A 1 (PLA 1 ) .
  • the PLA 1 is included in an amount of at least about 0.1%by weight PLA 1 to lecithin weight.
  • the PLA 1 is included in an amount of 0.2-0.8%by weight PLA 1 to lecithin weight, with about 0.3-0.5%by weight PLA 1 to lecithin weight being preferred.
  • the mixture of lecithin, solvent, buffer, and phospholipase is heated to a temperature sufficient to cause hydrolysis of the lecithin.
  • the mixture is heated to a temperature of at least 30°C for a time period of at least 15 minutes.
  • the mixture is heated to a temperature ranging from about 40-65°C for a time period of about 0.5-5 hours, with a temperature less than about 65°C and a time period of about 3-5 hours being preferred.
  • the PLA 1 is heated to a temperature and for a time period sufficient to deactivate the enzyme, which is generally a temperature of at least 70°C for at least 30 minutes.
  • the hydrolyzed mixture is next cooled to a temperature and for a time period sufficient to allow the phase separation to occur, which is generally to a temperature of 40°C or less and a time period of at least 30 minutes.
  • the lysolecithin component settles into the aqueous phase at the bottom while the oil and free fatty acid remain in the solvent phase on the top.
  • the aqueous phase is collected and dried using procedures known in the art including, but not limited to spray drying, drum drying, freeze drying, microwave drying, convective drying, conductive drying, air drying, etc.
  • the solution is dried to 20%by weight or less moisture.
  • the solution is dried to a moisture content of about 10%by weight or less.
  • the organic phase is either discarded or recycled.
  • the final composition contains a substantially higher percentage of LPI, with LPI content increased from about 1.4%to 6.5%and higher when using regular soy lecithin as the starting material. Furthermore, average LPC content also substantially increased from about 5%to 15%or higher. LPA content was also significantly higher. Overall, the invention provides a cost-effective, environmentally friendly and efficient way to prepare high-LPI, high-LPC, and high-LPA lysolecithin.
  • compositions of the present invention may optionally be combined with a pharmaceutically acceptable carrier that may include one or more carriers or excipients, such as fillers, diluents, binders, lubricants, and disintegrants.
  • a pharmaceutically acceptable carrier may include one or more carriers or excipients, such as fillers, diluents, binders, lubricants, and disintegrants.
  • carriers or excipients such as fillers, diluents, binders, lubricants, and disintegrants.
  • Phospholipase A1 enzyme –Lecitase Ultra was also obtained from KAC warehouse. It was produced by Novozyme and currently used for the on-site production of Lysoforte concentrate liquid (LCL) in KAC.
  • Thin layer chromatography plate sica gel matrix, aluminum foil backing, 20 x 20 cm
  • flash-chromatography column 50 mm x 60 cm, with fritted disc
  • silica gel 100-200 mesh
  • Phospholipase A1-catalyzed hydrolysis of lecithin in organic solvents This assay was developed to screen reaction parameters for the hydrolysis of lecithin.
  • a 20 mL sealed test tube 0.2 g lecithin and 2 mL organic solvent was added. The mixture was heated on 30-40 °C water bath and agitated occasionally in order to dissolve PC90 as much as possible. It was then heated on a 50 °C water bath.
  • Leictase Ultra was diluted to 50%with ultrapure deionized water and added to the mixture according to the dosage level.
  • the reaction mixture was continuously incubated at 50 °C and sampled after 1 hr, 2hrs and 4 hrs for thin layer chromatography (TLC) analysis (described later) .
  • TLC thin layer chromatography
  • the TLC could semi-quantitatively determine the conversion of lecithin to lysolecithin.
  • the assay was repeated several times by varying the solvent, concentration of substrate and enzyme dosage.
  • 31P-NMR and LC-MS analysis 31 P-NMR was run by Spectral Service AG in Germany. It gave the molar ratio of phospholipid and lysophospholipid molecules to an internal standard, triphenyl phosphate (PPh 3 ) 10 . The weight percent of each molecule could be calculated based on their molecular weight and molar ratio from 31 P-NMR.
  • the conversion was estimated by ratio of lecithin/ (lecithin+lysolecithin) on the thin layer chromatography (TLC) plate.
  • TLC thin layer chromatography
  • MTBE and EtOAc are found to be very good solvent for the enzymatic hydrolysis of lecithins. They both gave >90%conversion. More interestingly, there are precipitates in both solvents and we find most LPI product stays in the precipitate whereas fatty acids stay in the solvent, allowing the enrichment of LPI by simply decanting the organic layer.
  • This new enzymatic synthesis consists of all easy-handling steps: reaction, decanting, washing and filtration. No complicated purification process is needed.
  • Two organic solvents involved in the synthesis are ethyl acetate and ethanol. They are both environment-friendly and quiet acceptable in food industry.
  • the reaction step requires a small amount of water for the hydrolysis process, so the moisture in open air would not be a problem for the synthesis. Moreover, no mixed solvent is used all through the process. Ethyl acetate and ethanol could be easily distilled separately and reused for next batches of synthesis. It possesses the property of a scalable reaction. It can be scaled up to kilo or hundred kilos scale after necessary modifications.
  • De-oiled powdery lecithin (light yellow powder) containing high phosphatidylinositol (PI, 24%) and less phosphatidylcholine (PC, 5%) was purchased from Maxim Biotechnology Co., Ltd, Jiangsu, China; phospholipase A 1 (Lecitase Ultra, Novozymes, Lot#1801106600) and ethyl acetate (AR grade, 99%) and regular soy lecithin were used from the KAC warehouse; NaH 2 PO 4 ⁇ 2H 2 O and Na 2 HPO 4 ⁇ 12H 2 O (AR grade) were purchased from Guangzhou Chemical Reagents Factory. All organic solvents were of HPLC grade if not mentioned specifically.
  • phosphate buffer PBS, pH 7.0, 0.1 M
  • 20.66 g of Na 2 HPO 4 ⁇ 12H 2 O and 6.6 g of NaH 2 PO 4 ⁇ 2H 2 O were dissolved in 950 ml deionized water, and adjusted pH 7.0, followed by dilution to 1000 ml.
  • reaction time 0.5, 1.0, 1.5, 2, 3, and 4 h
  • reaction temperature 40 °C, 50 °C, 60 °C, and 65 °C
  • EtOAc volume 300%, 500%, 750%and 1000%of lecithin, volume to lecithin weight, v/w
  • PBS content 20%, 40%, 60%and 100%, weight to lecithin weight, w/w
  • Pilot production of high-LPI lysolecithin Three batches of production were performed in Hongji Photoelectric Material Co., Ltd. Fuxin, Liaoning province, China. Regular soy lecithin was used as the starting material. The optimal conditions were applied for pilot production. Briefly, 250 kg regular soy lecithin (RM45557, Lot. 1902111680) , 75 kg PBS, 800 kg EtOAc and 0.5 kg PLA 1 were loaded into an enamel reactor (2000 L) . The reactor was equipped with a spiral mixer, a temperature controller, and a vacuum distillation system (Figure 2) . The flow chart for pilot production of high-LPI lysolecithin is shown in Figure 3.
  • PLA 1 was de-activated at 75°C for 30 min in the reactor.
  • the aqueous phase containing lysolecithin, PBS and minor EtOAc was discharged from the bottom of the reactor. It was condensed and then put on stainless-steel trays and dried in a steam oven. Samples were withdrawn from reaction mixture at 2 h, 3 h and 4 h and dried in oven for the quantification of LPI and LPC level. The product after oven drying was also collected for LPI and LPC analysis.
  • HPLC High-performance liquid chromatography
  • the reaction system was able to fully hydrolyze PI as well as enrich the hydrolyzed product (LPI) in the final product.
  • LPI contents in the lysolecithin prepared by this new method were at the range of 5.8-13.1%, which were 5-10 times higher than that in commercial lysolecithins.
  • the method was also verified at 250 kg scale to produce bulk quantities of high-LPI lysolecithin.
  • This new enzymatic modification of lecithin consists of all easy-handling steps: reaction, phase separation, and drying. No complicated purification process is needed. Although many organic solvents were reported to tolerate enzymatic hydrolysis of lecithins 5- 7, 12 , EtOAc was used in our process because it was environmentally friendly and quite acceptable in both food and feed industries. First, for the reaction itself, it required a small amount of water for the hydrolysis process, so the moisture in open air would not be a problem for the reaction. No mixed solvent was used all through the process. Ethyl acetate could be easily distilled separately and reused for subsequent batches. Second, the process did not contain any difficult or expensive purification steps.
  • Lysolecithin automatically formed an emulsion in the aqueous phase and then was separated from the starting materials and free fatty acid by-product.
  • All raw materials used in the reaction were not expensive except phosphatase A 1 .
  • the dosage of PLA 1 was only 0.2% (w/w) so the overall cost was still very low.

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Abstract

La présente invention concerne une lysolécithine à IPL élevé et des procédés associés. Le produit à IPL élevé est obtenu par la réaction de la lécithine selon un procédé unique utilisant un solvant, un tampon et une phospholipase. Selon le procédé de production de l'invention, la teneur en LPI passe de 1,4 % à entre 2.5 et 13,1 % en utilisant la lécithine de soja ordinaire comme matière première, et les teneurs en LPC, LPE et LPA augmentent également de 5,1 %, 2,0 % et 1,0 % à 15,8 %, 14,6 % et 4,4 % respectivement.
PCT/CN2020/100444 2020-07-06 2020-07-06 Procédé pour la préparation de lysophosphatidylinositol WO2022006711A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
PCT/CN2020/100444 WO2022006711A1 (fr) 2020-07-06 2020-07-06 Procédé pour la préparation de lysophosphatidylinositol
US17/235,561 US20220002325A1 (en) 2020-07-06 2021-04-20 Method for the preparation of lysophosphatidylinositol
PCT/US2021/028184 WO2022010559A1 (fr) 2020-07-06 2021-04-20 Procédé de préparation de lysophosphatidylinositol
CN202180046187.7A CN115867293A (zh) 2020-07-06 2021-04-20 溶血磷脂酰肌醇的制备方法

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5955327A (en) * 1997-04-08 1999-09-21 Tsuji Oil Mill Co., Ltd. Process for manufacturing vegetable lysolecithins
WO2011046815A1 (fr) * 2009-10-16 2011-04-21 Bunge Oils, Inc. Procédés de démucilagination d'huile
WO2011046812A1 (fr) * 2009-10-16 2011-04-21 Verenium Corporation Phospholipases, acides nucléiques codant pour celles-ci et leurs procédés de fabrication et d'utilisation
WO2019123015A1 (fr) * 2017-12-21 2019-06-27 Aker Biomarine Antarctic As Compositions de lysophosphatidylcholine
US20190281852A1 (en) * 2016-12-08 2019-09-19 Mitsubishi-Chemical Foods Corporation Oil-in-water type emulsion composition, and method for producing said oil-in-water type emulsion composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5955327A (en) * 1997-04-08 1999-09-21 Tsuji Oil Mill Co., Ltd. Process for manufacturing vegetable lysolecithins
WO2011046815A1 (fr) * 2009-10-16 2011-04-21 Bunge Oils, Inc. Procédés de démucilagination d'huile
WO2011046812A1 (fr) * 2009-10-16 2011-04-21 Verenium Corporation Phospholipases, acides nucléiques codant pour celles-ci et leurs procédés de fabrication et d'utilisation
US20190281852A1 (en) * 2016-12-08 2019-09-19 Mitsubishi-Chemical Foods Corporation Oil-in-water type emulsion composition, and method for producing said oil-in-water type emulsion composition
WO2019123015A1 (fr) * 2017-12-21 2019-06-27 Aker Biomarine Antarctic As Compositions de lysophosphatidylcholine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
AURA A.-M., ET AL.: "ENZYMATIC HYDROLYSIS OF OAT AND OYA LECITHIN: EFFECTS ON FUNCTIONALPROPERTIES.", JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, SPRINGER, DE, vol. 71., no. 08., 1 August 1994 (1994-08-01), DE , pages 887 - 891., XP002033240, ISSN: 0003-021X, DOI: 10.1007/BF02540468 *
REDDY JALA J C, CHEN B, LI H, ZHANG Y, CHEONG L-Z, YANG T, XU X: "Enzymatic preparation and characterization of soybean lecithin-based emulsifiers", GRASAS Y ACEITES, CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (SPANISH NATIONAL RESEARCH COUNCIL)., SPAIN, vol. 67, no. 4, 30 December 2016 (2016-12-30), SPAIN , XP055886550, ISSN: 0017-3495, DOI: 10.3989/gya.0571161 *

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