Rapid Thermal Isomerization of Lycopene

Abstract

The use of lycopene has been demonstrated to be effective in decreasing risk factors associated with cardiovascular disease, skin cancer and prostate cancer in mammals. Lycopene is difficult to solubilize in its native trans-lycopene form. Cis-lycopene, formed by applying thermal energy generated by excitation of polar molecules through microwave-assisted processing, appears in several isomeric forms. The cis isomers are effective in improving lycopene micellularization, bioaccessibility and mammalian absorption. The cis isomers are effective in improving vascular circulation of lycopene by way transport vesicle low density lipo-protein (LDL). Lycopene-based ingredients, end products, functional foods, medical foods and nutraceuticals, containing isomerized cis-lycopene can be used in place of ingredients with more naturally abundant trans-lycopene as phytonutrient, micronutrient and antioxidant delivery vehicles through dietary consumption to improve the outcomes of a variety of conditions, including hypertension, cardiovascular disease, skin cancer, prostate cancer, macular degeneration and related proinflammatory conditions.

Claims

1. A process for the rapid thermal isomerization of a mixture of all-trans-lycopene and its cis-isomers of any composition to increase the proportion of cis-isomers, wherein the isomerization takes place in a polar solvent.

2. A functional ingredient, nutraceutical, functional food, medical food composition suitable for administration to mammal, comprising greater than 4% of isomerized cis-lycopene compared to total lycopene content.

3. A process claimed in claim 1, wherein the isomerization takes place by way of energizing polar water molecules and ionic salt compounds through friction within the food mixture matrix using microwave-assisted heating

4. A process claimed in claim 1, wherein the isomerization takes place by way of energizing food mixture matrix using volumetric heating.

5. A process as claimed in claim 1, wherein the isomerization takes place at between 60 and 180 degree C.

6. A process as claimed in claim 1, wherein the monounsaturated and polyunsaturated fatty acids such as edible oils including but not limited to canola oil, olive oil, sunflower oil, safflower oil, saffron oil, vegetable oil, grapeseed oil, black cumin seed oil, cooking oils, omega 3 fatty acids, omega 6 fatty acids, fat soluble vitamins E, D, K, A are used as solvent components and processing aids in water used as solvent.

7. A process as claimed in any of claim 1, wherein C.sub.1 C.sub.8-alcohols, diols, polyols, amides, carbonates, sulfoxides, or water are used as solvent.

8. A process as claimed in any of claim 1, wherein methanol, ethanol, isopropanol, butanol or organic solvents are used as solvent or processing aids.

9. A process as claimed in any of claim 1, wherein surfactants, including but not limited to proteins, amino acids, lecithin, monoglycerides, diglycerides, triglycerides, fat soluble vitamins E, D, K, A used as solvent or processing aids.

10. A process as claimed in any of claim 1, wherein cation other than H, preferably Na.sup+ or K.sup+ or Li.sup+ or Iodine is used as a processing aid to increase isomerization potential or enhance dielectric properties though out carotenoid solvent matrix.

11. A process as claimed in any of claim 1, wherein less than 97% of total lycopene is in the all-trans-lycopene crystalline form at the chosen isomerization temperature.

12. A process as claimed in any of claim 1, wherein more than 4% of the total lycopene content is in its cis-lycopene isomeric form at the chosen isomerization temperature.

13. A process as claimed in any of claim 1, where in 0.2% or more of trans-Lycopene is converted to cis-lycopene isomeric form at the chosen isomerization temperature.

13. A process as claimed in claim 1, wherein the lycopene mixture comprises 5-cis lycopene.

14. A process as claimed in claim 1, wherein the lycopene mixture may comprise 7-cis lycopene

15. A process as claimed in claim 1, wherein the lycopene mixture may comprise 9-cis lycopene.

16. A process as claimed in claim 1, wherein the lycopene mixture may comprise 11-cis lycopene.

17. A process as claimed in claim 1, wherein the lycopene mixture may comprise 13-cis lycopene.

18. A process as claimed in claim 1, wherein the lycopene mixture may comprise 15-cis lycopene.

19. A process as claimed in claim 1, where said carrier is a buffered solution having a pH greater than 2.0

Description

DETAILED DESCRIPTION OF INVENTION

[0022] Theoretically lycopene can assume 211 or 2048 geometrical configurations, due to the 11 conjugated carbon-carbon double bonds in its backbone (Omani, 2005). Lycopene biosynthesis in plants leads to the all-trans-form that is independent of its thermodynamic stability. In human plasma, lycopene is an isomeric mixture, containing at least 60% of the total lycopene as cis-isomers (Kim, 2012).

[0023] All-trans, 5-cis, 9-cis, 13-cis, and 15-cis are the most commonly identified isomeric forms of lycopene with the stability sequence being 5-cis>all-trans>9-cis>13-cis>15-cis>7-cis>11-cis (Agarwal, 2000). The 5-cis-form is thermodynamically more stable than the all-trans-isomer, nevertheless a large number of geometrical isomers are theoretically possible for all-trans lycopene with limitations to cis-trans isomerization by steric hinderance of ethylenic groups of certain lycopene molecules (Agarwal, 2000).

[0024] In fruit such as tomatoes lycopene exists in chromoplast as ratio of E/Z or trans/cis isomers depending on cultivar and degree of ripeness. Our lab has observed homogenized untreated samples with a ratio of trans to cis at 96:4, respectively. Studies performed by Honda et al on isomerization of trans-lycopene, purified from tomato paste, was investigated with organic solvents and the isomerization ratios to the cis-isomer of lycopene ranged from 11.4% at 4 C to 77.8% at 50 C for 24 hrs (Honda, 2015).

[0025] Previous state of the art in lycopene isomerization process approved for patent protection was designed to convert existing Z or cis-lycopene isomers in lycopene containing material such as tomatoes to E or trans-lycopene isomers (U.S. Pat. No. 7,126,036). These processes involving organic solvents and traditional thermal processes entailed several ours of processing in the range of 2-160 hours, preferably 16 to 40 hours at select temperatures.

[0026] There is to date no method by which a mixture of trans-lycopene isomers or else individual trans-lycopene can be converted efficiently in minutes to cis-lycopene isomer forms. There is to date no method by which a mixture of cis-lycopene or else individual cis-lycopene can be excited efficiently in minutes into other cis-lycopene isomer forms.

[0027] It is an object of the present invention to develop an efficient method or isomerizing the trans-lycopene form into cis-lycopene form which does not have the described prior art disadvantages and makes it possible to use the more energy efficient and cost-effective thermal energy transfer isomerization process for lycopene.

[0028] We have found that this object is achieved by a process for the volumetric heating and/or microwave-assisted rapid thermal isomerization of a mixture of trans-lycopene and its cis-isomers of any composition to increase the proportion of cis-lycopene isomers, wherein the isomerization takes place in a polar solvent in which lycopene is insoluble or slightly soluble.

[0029] The invention thus relates to a process for the thermal isomerization of trans-lycopene and its cis-lycopene isomers of any composition to increase the proportion of cis-lycopene, wherein the isomerization takes place in a polar solvent.

[0030] The process of the invention makes use of a suspension of lycopene in a polar solvent in which lycopene is insoluble soluble or slightly soluble.

[0031] Polar solvents employed are water or water/oil.

[0032] Polar solvents are monounsaturated and polyunsaturated fatty acids such as edible oils including but not limited to olive oil, canola oil, sunflower oil, vegetable oil, safflower oil, grapeseed oil saffron oil, black cumin seed oil, cooking oils, omega 3 fatty acids, omega 6 fatty acids, lecithin, surfactants and fat soluble vitamins E, D, K, A.

[0033] Polar solvents employed can be alcohols such as C.sub.1 C.sub.8-alcohols, diols, polyols, amines, carbonates, sulfoxides or edible oils.

[0034] C.sub.1 C.sub.8-Alcohols are, for example, methanol, ethanol, ethylene glycol, glycerol, propanol, isopropanol, butanol, tert-butanol, pentanol, hexanol, heptanol, or octanol, and methanol, ethanol, or butanol are preferably employed. An example of a diol which can be employed is ethylene glycol. Polyols mean, for example, polyethylene glycol. Examples of amines are formamide, acetamide, methylformamide, methylacetamide, dimethylformamide, dimethylacetamide or y-butyrolactone. Carbonates mean, for example, ethylene carbonate or propylene carbonate. An example of a sulfoxide which can be used is dimethyl sulfoxide.

[0035] The process of the invention exploits the effect that microwave assisted heating excites polar molecules throughout the discontinuous phase of the homogenate composition which contains the continuous phase comprising the virtually insoluble trans-lycopene accompanied by 5-cis-lycopene in their respective most thermodynamically stable forms. Thermogenesis formed from polar and ionic molecules activated by microwave generation excites lycopene isomers to change conformation favoring increases in cis-isomer content and cis-isomerization. In this case it is possible, if the temperature is sufficiently high, for there to be selective isomerization of cis-lycopene isomers, because the trans-lycopene isomers bound in the crystal have a considerably higher isomerization activation energy. Owing to the properties of crystalline trans-lycopene, solubilization with oil or polyunsaturated triglycerides lowers trans-lycopene isomerization activation energy thus allowing the process of the invention to exploit the effect of microwave assisted heating or volumetric heating to effectively excite polar and ionic molecules throughout the continuous and discontinuous phases of the fruit or vegetable homogenate containing lycopene. Overall, the isomerization equilibrium can thus be shifted towards the cis-lycopene isomer.

[0036] The isomerization temperature is between 40 and 180 degree C., preferably between 60 and 120 degree C. The isomerization can be carried out both under atmospheric pressure and under elevated pressure, preferably under pressures of from 0 to 10 bar. The isomerization process duration is between 0.25 minutes and 2,880 minutes, preferably between 2 minutes and 1,440 minutes.

[0037] A suspension of lycopene in a polar solvent in which lycopene is insoluble or only slightly soluble is prepared after shear stress homogenization processing of fruit or vegetable material to give lycopene directly in this polar solvent. Hydrophobic compounds, oil and/or amphiporus surfactant processing aids can be added during the homogenization process within a range between 0.25%-75% of lycopene, preferably between 1%-60% of lycopene to improve lycopene solubilization in polar solvent.

[0038] It is then possible for lycopene, in various ratios of amounts in relation to the polar solvent, preferable as 1 to 98% strength suspension of lycopene in the polar solvent, to be isomerized by microwave or dielectric property influenced volumetric heating or thermogenesis.

[0039] This can then be followed by 8 different variants: firstly, the homogenate suspension can be isomerized directly by microwave or volumetric heating. An alternative is to add edible oil or polyunsaturated fatty acids and subsequently isomerize by heating. In the third variant, the surfactant, for example, lecithin is added to the homogenate suspension with or without oil, and then isomerization is carried out. The fourth variant, adding an alcohol, for example methanol, and subsequently to isomerize by heating. The fifth variant, the solvent incorporates, for example, n-butanol, and then is isomerization is carried out. The sixth variant, the solvent incorporates, for example, hexane then the isomerization is carried out. The seventh variant, the solvent incorporates, for example ethyl acetate then the isomerization is carried out. The eighth variant, the solvent incorporates, for example alkyl halides such as dichloromethane or chloroform then the isomerization is carried out.

[0040] The lycopene quality and quantity can be evaluated by cooling the suspension, and performing a lycopene extraction and washing, then determining the qualitative and quantitative content by HPLC measurement.

[0041] It was possible to increase 9-cis-lycopene isomer by 1010% in HR (Heated Roma) compared to control (unheated) (FIG. 3), increase 7-cis-lycopene isomer by 344% in HR compared to control (FIG. 2), and increase di-cis-lycopene isomer by 99.4% in HR compared to control (FIG. 6). Results from in-vitro digestibility assay confirmed increases in cis-lycopene isomerization translated into a 25% increase in relative bioaccessbility of cis-lycopene (FIG. 12) in HR. No significant increase in absolute bioaccessbility for total cis-Lycopene or trans-Lycopene was observed in HR compared to control (FIGS. 10 & 11).

[0042] It was possible to increase 9-cis-lycopene isomer by 758% in HRO (Heated Roma Oil) compared to control (unheated) (FIG. 3), increase 9-cis-lycopene isomer by 50% in HRO compared to control (FIG. 4), increase 13-cis-Lycopene isomer by 40000% in HRO compared to control (FIG. 5), and increase di-cis-lycopene isomer by 182% in HRO compared to control (FIG. 6). Data shows a 350% increase of c-Lycopene-1 in HRO compared to control (FIG. 7). Results from in-vitro digestibility assay confirmed increases in cis-lycopene isomerization translated into a 100% increase in relative bioaccessbility of cis-lycopene in HRO (FIG. 12) and a 315% increase in total-Lycopene relative bioaccessbility in HRO compared to control (FIG. 12). Additionally, HRO treatment expressed a 200% increase in total cis-Lycopene isomer absolute bioaccessbility (FIG. 10) and a 220% increase in trans-Lycopene isomer absolute bioaccessbility compared to control (FIG. 11).

[0043] It was possible to increase 9-cis-lycopene isomer by 333% in HROL (Heated Roma Oil/Lecithin) compared to control (unheated) (FIG. 3), no significant increase 9-cis-lycopene isomer in HROL compared to control (FIG. 4), increase di-cis-lycopene isomer by 81.9% in HROL compared to control (FIG. 6). Data shows a 270% increase of c-Lycopene-1 in HROL compared to control (FIG. 7). Results from in-vitro digestibility assay confirmed increases in cis-lycopene isomerization translated into a 362.8% increase in relative bioaccessbility of cis-lycopene in HROL (FIG. 12) and a 905.6% increase in total-Lycopene relative bioaccessbility in HROL compared to control (FIG. 12). Additionally, HROL treatment expressed a 650% increase in total cis-Lycopene isomer absolute bioaccessbility (FIG. 10) and 850% increase in trans-Lycopene isomer absolute bioaccessbility compared to control (FIG. 11).

[0044] It was possible to influence the cis/trans isomer ratio based upon processing conditions concerning the current invention. Analysis of isomer ratio in mg/100 g showed a cis/trans ratio of 1:15 for control, 1:12 for HR, 1:7 for HRO and 1:9 for HROL, which collectively represents lycopene crystalline structure solubilization and isomerization efficiency as cis/trans ratio is shifted in the direction of cis-lycopene at the expense of trans isomer. Moreover, it was possible identify a shift in cis/trans lycopene percentage ratio shift from 4%:96% in control, to 8%:92% in HR, 12%:88% in HRO and 10%:90% in HROL. This data is consistent with both increases in cis-isomer generation by microwave or volumetric mediated heating and increases observed in absolute and relative bioaccessbility of lycopene and its isomers in heat treated samples (HR, HRO, HROL) versus control untreated samples.

[0045] Cis-Lycopene isomerization is obtained by homogenizing lycopene containing fruit or vegetable and heating using microwave or volumetric mediated thermogenesis. Lycopene is a naturally occurring carotenoid, and is otherwise available to those of skill in the art. It may be obtained from a large variety of natural sources, including tomato.

[0046] The advantages which can thus be achieved overall by the volumetric heating and/or microwave-assisted thermal lycopene isomerization method of the invention are as follows: increase in more bioavailable yield of cis-lycopene isomer in processed lycopene containing material, decrease in isomerization activation energy requirement, decrease in thermal processing times necessary to achieve desired lycopene isomerization, decrease in cost of production due to rapid, efficient and identifiable processing end points defined by quantification of lycopene isomer quality, and increase in lycopene bioaccessiblility due to increase in micellularization efficiency of lycopene and its isomers resulting from the novel process invention.

[0047] In vitro bioaccessibility assay was used to simulate human oral, gastric and small intestinal digestion based on the method described by Hedren et al and Garrett et al. Tomatoes were subjected to a three-stage static in vitro digestion model, and lycopene was analyzed by HPLC-MS. The lycopene bioaccessibility of a sample is reported as a ratio (%) of the in vitro bioaccessible lycopene content to the corresponding lycopene content of the sample. This in vitro digestion model has been widely applied to fat-soluble micronutrients vitamin D, Vitamin E, vitamin K, fat-soluble carotenoids to model gastric and small intestinal release as well as micellarization (Reboul 2011, Failla 2008). In the small intestine, bile is required to incorporate lycopene into mixed micelles (Schachter 1964). Lycopene that has been released from the food matrix and solubilized in mixed micelles is available for subsequent absorption at the epithelial surface in the duodenum and jejunum (bioaccessible). While in vitro methodologies may not fully portray in vivo bioavailability, this approach offers a method to comparatively assess lycopene containing food matrixes with additional insight into confirming the impact processing including but not limited to rapid microwave-assisted or dielectric property mediated volumetric heat induced lycopene isomerization has on improving lycopene solubilization and micellularization leading to enhanced absorption capacity for lycopene antioxidants.

[0048] This invention has been disclosed in terms of specific embodiments, and generic description. The specific embodiments are not intended as limiting, and variations will occur to those of ordinary skill in the art without the exercise of inventive skill. Such variations remain within the scope of the invention, save as excluded by the recitations of the claims set forth. In particular, variations in isomerization procedure and specific condition will occur to those of ordinary skill in the art, without departing from the scope and spirit of the invention.

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DESCRIPTION OF THE FIGURE

[0237] FIG. 1 illustrates the structural distinctions of the predominant lycopene geometrical isomers. Geometric isomers of lycopene, all-trans lycopene, 15-cis lycopene, 13-cis lycopene, 11-cis lycopene, 9-cis lycopene, 7-cis lycopene, 5-cis lycopene

[0238] FIG. 2 illustrates the quantification of 7-cis-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. The data shows a 344% increase of 7-cis-Lycopene in HR (heated roma) compared to control (unheated) roma.

[0239] FIG. 3 illustrates the quantification of 9-cis-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. The data shows a 1010% increase of 9-cis-lycopene in HR (heated roma) compared to control (unheated). 9-cis lycopene in HRO (heated roma w/oil) increased by 758% compared to control. 9-cis lycopene in HROL increased by 333% compared to untreated control.

[0240] FIG. 4 illustrates the quantification of 9-cis-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. The data shows a 50% increase of 9-cis-lycopene in HRO (Heated Roma Oil) compared to control (unheated).

[0241] FIG. 5 illustrates the quantification of 13-cis-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. The data shows a 40000% increase of 13-cis-lycopene in HRO (Heated Roma Oil) compared to control (unheated)

[0242] FIG. 6 illustrates the quantification of di-cis-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. The data shows a 99.4% increase of di-cis-Lycopene isomer in HR (heated roma) compared to control (unheated). Data shows a 182% increase of di-cis-Lycopene isomer in HRO compared to control. Data shows an 81.9% increase of di-cis-Lycopene isomer in HROL compared to control

[0243] FIG. 7 illustrates the quantification of c-lycopene-1 detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. Data shows a 350% increase of c-Lycopene-1 in HRO compared to control; Data displays a 270% increase of c-Lycopene-1 in HROL (Heated Roma Oil/Lecithin) compared to control.

[0244] FIG. 8 illustrates the quantification of 5-cis-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. Stable form 5-cis-lycopene decreased in HR, HRO and HROL by 8.7%, 29.5%, 21.5% (respectively) compared to control.

[0245] FIG. 9 illustrates the quantification of trans-lycopene detected in processed Roma Tomatoes for unheated control, heated, heated with oil and heated with oil and lecithin. Stable form trans-lycopene remained constant in HR compared to control. HRO and HRL expressed 31.9% and 9.64%, respectively, decreased trans-Lycopene content compared to control.

[0246] FIG. 10 illustrates the quantification of cis-Lycopene Absolute Bioaccessibility identified in processed Roma Tomatoes for unheated control, heated, heated with oil, heated with oil/lecithin. Data shows absolute bioaccessibility of total cis-Lycopene increase 200% in HRO compared to control; Data displays a 650% increase in total cis-Lycopene absolute bioaccessibility in HROL (Heated Roma Oil/Lecithin) compared to control.

[0247] FIG. 11 illustrates the quantification of trans-Lycopene Absolute Bioaccessibility identified in processed Roma Tomatoes for unheated control, heated, heated w/oil, heated w/oil+lecithin. Data shows absolute bioaccessbility of trans-Lycopene decreased 20% in HR compared to control, Trans-Lycopene absolute bioaccessibility increased 220% in HRO compared to control, and increased 850% in HROL compared to control

[0248] FIG. 12 illustrates the quantification of % Relative Bioaccessibility (aqueous/digestia) calculated in processed Roma Tomatoes for unheated control, heated, heated w/oil, heated w/oil+lecithin. Relative bioaccessbility of cis-lycopene increased by 25% in HR compared to control. Cis-Lycopene relative bioaccessbility increased in HRO by 100% compared to control. Cis-Lycopene in HROL increased by 362.8% compared to control. Total-Lycopene relative bioaccessbility remained constant in HR, compared to control but increased by 315.5% in HRO compared to control, increased by 905.6% in HROL compared to control