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EP-4735561-A1 - MODIFIED BLACK SOLDIER FLY OIL EXTRACT AND USES THEREOF

EP4735561A1EP 4735561 A1EP4735561 A1EP 4735561A1EP-4735561-A1

Abstract

A modified, monoglyceride-enriched black soldier fly (BSF) oil extract, compositions, and edible products such as feed and food supplemental products comprising same and uses thereof in treating or preventing inflammation and/or microbial infection and/or biofilm formation, and/or in reducing a mortality, increasing an average body weight and/or improving a feed conversion ratio in a population comprising a plurality of subjects, are provided. A composition comprising a monoglyceride-enriched oil and a plant oil or extract derived from a Lamiaceae plant and uses thereof are also provided. The subjects to treated include, for example, human being, pets, farm animals, fish and crustaceans.

Inventors

  • BARZILAY, AMIR
  • LAPIDOT, MIRI
  • WITTENBERG, Gal
  • BARON, Yuval

Assignees

  • NeoManna Ltd

Dates

Publication Date
20260506
Application Date
20240627

Claims (20)

  1. 1. A modified, monoglyceride-enriched black soldier fly (BSF) oil extract, comprising one or more monoglycerides in a total amount that is higher by at least 20 % of a total amount of monoglycerides in an unmodified BSF oil extract.
  2. 2. The modified BSF oil extract of claim 1, comprising one or more monoglycerides in a total amount of at least 25 %, at least 30 %, at least 35 %, at least 40 %, at least 45 %, at least 50 %, at least 55 %, at least 60 % or at least 65%, by weight of the total weight of the modified BSF oil extract.
  3. 3. The modified BSF oil extract of claim 1, comprising one or more monoglycerides in a total amount that ranges from 25 to 70 % by weight, of the total weight of the modified BSF oil extract.
  4. 4. A modified BSF oil extract comprising monoglycerides in a total amount of at least 25 %, at least 30 %, least 35 %, at least 40 %, at least 45 %, at least 50 %, at least 55 %, at least 60 % or at least 65 % by weight of the total weight of the modified BSF oil extract.
  5. 5. The modified BSF oil extract of claim 4, wherein a total amount of the monoglycerides ranges from 25 to 70 %, by weight, of the total weight of the modified BSF oil.
  6. 6. The modified BSF oil of any one of claims 1 to 5, comprising monolaurin in an amount of at least at least 10 %, or 15 %, or at least 20 %, or at least 25 %, or at least 30% by weight, of the total weight of the modified BSF oil.
  7. 7. The modified BSF oil of any one of claims 1 to 5, comprising monolaurin in an amount that ranges from 10 to 40 %, by weight, of the total weight of the modified BSF oil.
  8. 8. The modified BSF oil of any one of claims 1 to 7, comprising monolaurin in an amount that ranges from 25 to 75 %, by weight, of the total weight of the one or more monoglycerides in the modified BSF oil.
  9. 9. The modified BSF oil of any one of claims 1 to 8, further comprising triglycerides in a total amount of no more than 25%, no more than 20 % or no more than 10% by weight of the total weight of the modified BSF oil.
  10. 10. The modified BSF oil of any one of claims 1 to 9, further comprising diglycerides in a total amount of no more than 40 %, no more than 35% or no more than 30 %, by weight of the total weight of the modified BSF oil.
  11. 11. The modified BSF oil of any one of claims 1 to 10, further comprising free fatty acids, in a total amount of no more than 10, % by weight of the total weight of the modified BSF oil.
  12. 12. The modified BSF oil of any one of claims 1 to 11, further comprising glycerol in an amount of no more than 15 %, no more than 12% or no more than 10 %, by weight of the total weight of the modified BSF oil.
  13. 13. A process of preparing a modified, monoglycerides-enriched BSF oil, the process comprising contacting a BSF oil extract with glycerol, and an alkaline substance, under conditions that promote transesterification.
  14. 14. The process of claim 13, wherein a mol ratio of said BSF oil extract and said glycerol ranges from 2: 1 to 1 : 10, or from 1 : 1 to 1 : 10, or from 1 : 1 to 1 :6, or from 1 : 1 to 1 :4, or from 1 :2 to 1 :3.
  15. 15. The process of claim 13 or 14, wherein said alkaline catalyst is a methoxide or a hydroxide.
  16. 16. The process of any one of claims 13 to 15, wherein a mol ratio of said alkaline substance and said BSF oil extract ranges from 1 : 100 to 10: 100 .
  17. 17. The process of any one of claims 13 to 16, wherein said conditions comprise heating said mixture, for example, to a temperature of at least 100, or at least 150 °C, under reduced pressure .
  18. 18. The process of any one of claims 13 to 17, wherein said contacting is for a time period that ranges from 1 to 24 hours.
  19. 19. The process of any one of claims 13 to 18, further comprising, subsequent to said contacting, removing the glycerol from said mixture, to thereby obtain the modified BSF oil.
  20. 20. The process of claim 19, wherein said removing is such that an amount of the glycerol in the modified BSF oil is less than 20 %, or less than 15%, or less than 10% by weight of the total weight of the modified BSF oil.

Description

MODIFIED BLACK SOLDIER FLY OIL EXTRACT AND USES THEREOF RELATED APPLICATION This application claims the benefit of priority from US Provisional Application No. 63/523,421, filed June 27, 2023, the contents of which are incorporated herein by reference in their entirety. FIELD AND BACKGROUND OF THE INVENTION The present invention, in some embodiments thereof, relates to monoglyceride-enriched oil, such as, but not limited to, monoglyceride-enriched black soldier fly (BSF) oil extract, to processes of preparing same, to compositions and products comprising same and to uses thereof. Black soldier fly (BSF; Hermetia illucens) larvae (BSFL) are rich in fat, with levels typically ranging between 15 % and 49 % on dry matter basis. Notably, the fatty acid profile of the prepupae is high in the medium-chain fatty acids (MCFAs), with lauric acid (C12:0) being the major component. Lauric acid is known to have antiviral, antifungal and antibacterial activity, and as particularly active against Gram positive bacteria. The fatty acid profile of the prepupae contains additional MCFAs such as capric acid (C10:0) and caprylic acid (C8:0). Trials showed that black soldier fly prepupal fat (0.58 gram C 12:0/100ml) suppressed growth of Lactobacilli, and exhibited substantial antibacterial effects against D-streptococci infections in pigs. In vivo experimentations suggested that these positive effects are most likely seen when farming conditions and/or health status are sub-optimal [Gasco et al., Journal of Insects as Food and Feed (2018), 4(1), 1-4], It has also been reported that while some components of virgin coconut oil (VCO), such as medium-chain fatty acids (MCFAs), monoglycerides and free fatty acids (FFA) exhibit antimicrobial activity, other components such as triglycerides and diglycerides have a lesser antimicrobial activity. It has been suggested that VCO may be metabolized to release MCFAs such as caprylic acid (C8:0), capric acid (C10:0), and lauric acid (C12:0) to exert its antimicrobial effects [Shilling et al., Journal of medicinal food (2013), 16(12), 1079-1085], Lauric acid in insect larvae is stored mainly as triglycerides [Liland et al., PLoS ONE (2017), 12(8), eO 183188] . There are several ways known in the industry to break triglycerides into monoglycerides and free fatty acids to enhance its antimicrobial properties. For example, WO 2007/067028 describes that coconut oil and palm kernel are hydrolyzed using the catalytic activity of 1,3 -positional specific lipases to provide modified oil compositions that comprise free fatty acids (FFAs, 9.40-25.01 %), monoglycerides (MAGs, 1.31-14.28 %), diglycerides (DAGs, 21.66- 39.98 %) and triglycerides (TAGs, 25.08-64.16 %), and that these compositions are able to inhibit the growth of Gram-positive bacteria (i.e., Staphylococcus aurous aureus, Listeria monocytogenes, Streptococcus pyogenes), Gram-negative bacteria (i.e., Vibrio cholerae, Escherichia coli) and yeast (i.e., Candida albicans). Fatty acids and monoglycerides achieve their antimicrobial effects by several mechanisms. An early postulated mechanism is the perturbation of the microorganism’s plasma membrane lipid bilayer. For example, the antiviral action attributed to monolaurin involves fluidizing the lipids and phospholipids in the envelope of the virus, and thereby causing the disintegration of the microbial membrane. Some studies indicate that one antimicrobial effect in bacteria is related to monolaurin's interference with signal transduction/toxin formation [Projan, et al., J Bacteriology (1994), 176, 4204-4209], Another antimicrobial effect in viruses relates to lauric acid's interference with virus assembly and viral maturation [Hornung et al., Journal of General Virology (1994), 75(2), 353-361], Another suggested mode of action involves an effect on the immune system itself [Witcher et al., Clinical and Diagnostic Faboratory Immunology (1996), 3, 10-13], Hess et al. [Surgical Infections (2015), 16(5), 538-542] teach using the natural surfactant glycerol monolaurate (GML) to inhibit biofilm development. WO 2020/234884 discloses a method that comprises extracting black soldier fly larvae (BSFL) oil, and modifying the BSFL oil by converting triglycerides in the BSFL oil to medium chain fatty acids (MCFAs) in the form of monoacylglycerides (MAGs, monoglycerides or MGs), up to 7.33 % w/w in BSFL oil; out of which monolaurin is the most abundant - up to 2.39 % w/w in BSFL oil), fatty acid salts and/or free fatty acids (FFAs, up to 3.13 % w/w in oil), by, e.g., saponification and/or hydrolysis. WO 2020/234884 teaches that the obtained modified BSFL (MBSFL) oil is usable in suppressing biofilm development and/or microorganism growth. Additional background art includes U.S. Patent Application Publication No. 2018/256483. SUMMARY OF THE INVENTION According to an aspect of some embodiments of the present invention there is provided a modified, monoglyceride-enriched black soldier fly (BSF) oil extract