Patent Grant
10119947
This application is the U.S. national stage application of International Patent Application No. PCT/FR2014/052046, filed Aug. 6, 2014.
The present invention relates to novel protein-rich compositions of biomass of microalgae of the Chlorella genus having an optimized sensory profile, thereby making it possible to incorporate them into food formulations without generating undesirable flavors, and also to a method for evaluating the organoleptic profile of a protein-rich composition of biomass of microalgae of the Chlorella genus.
It is well known to those skilled in the art that chlorellae are a potential source of food, since they are rich in proteins and other essential nutrients.
They contain especially 45% of proteins, 20% of fats, 20% of carbohydrates, 5% of fibers and 10% of minerals and vitamins.
The use of biomasses of microalgae (and principally the proteins thereof) as food is being increasingly considered in the search for alternative sources to meet the increasing global demand for animal proteins (as reported by the FAO).
Moreover, the European Union has been suffering from a structural deficit in plant proteins for years now, which has amounted in recent years to more than 20 million tons of soy equivalent, currently imported from South America.
The mass production of certain protein-rich microalgae is thus envisioned as a possible way to reduce this “protein deficit”.
Extensive analyses and nutritional studies have shown that these algal proteins are equivalent to conventional plant proteins, or even are of superior quality.
Nonetheless, due to the high production costs and technical difficulties in incorporating the material derived from microalgae into organoleptically acceptable food preparations, the widespread distribution of microalgal proteins is still in its infancy.
Microalgal biomasses from various species having a high percentage of proteins have been reported (see table 1 in Becker, Biotechnology Advances (2007), 25:207-210).
Additionally, a certain number of patent applications in the prior art, such as patent application WO 2010/045368, teach that it is possible to adjust the culturing conditions so as to further increase the protein content of the microalgal biomass.
However, when it is desired to industrially produce microalgal biomass powders from the biomass of said microalgae, considerable difficulties remain, not only from the technological point of view, but also from the point of view of the sensory profile of the compositions produced.
Indeed, while algal powders for example produced with algae photosynthetically cultured in exterior ponds or using photobioreactors are commercially available, they have a dark green color (associated with chlorophyll) and a strong, unpleasant taste.
Even formulated in food products or as nutritional supplements, these algal powders always give this visually unattractive green color to the food product or to the nutritional supplement and have an unpleasant fishy taste or the taste of seaweed.
Moreover, it is known that certain species of blue algae naturally produce odorous chemical molecules such as geosmin (trans-1,10-dimethyl-trans-9-decalol) or MIB (2-methylisoborneol), generating earthy or musty odors.
As for chlorellae, the descriptor commonly accepted in this field is the taste of “green tea”, slightly similar to other green vegetable powders such as powdered green barley or powdered green wheat, the taste being attributed to its high chlorophyll content.
Their taste is usually masked only when they are mixed with vegetables with a strong taste or citrus fruit juices.
There is therefore still an unsatisfied need for compositions of biomass of microalgae of the Chlorella genus of suitable organoleptic quality, allowing the use thereof in more numerous and diversified food products.
The applicant company has found that it is possible to meet this need by providing protein-rich microalgal biomass compositions having an optimized sensory profile, characterized by the overall flavor value of 4 volatile organic compounds chosen from 11 specific compounds.
Thus, the present invention relates first of all to a method for determining the organoleptic quality of a protein-rich microalgal biomass composition, comprising determining the content of 11 volatile organic compounds, the 11 volatile organic compounds being pentanal, hexanal, 1-octen-3-ol, 2-pentylfuran, octanal, 3,5-octadien-2-ol (or 3-octen-2-one), 3,5-octadien-2-one, nonanal, 2-nonenal, (E,E)-2,4-nonadienal and hexanoic acid.
Preferably, the microalgal biomass comprises more than 50% proteins by dry weight of biomass and the microalgae are of the Chlorella genus.
Preferably, the content of each of these 11 volatile organic compounds is determined by SPME/GC, preferably by SPME/GC-MS.
Preferably, the content of each of these 11 volatile organic compounds is determined by the surface area of the chromatography peaks after SPME/GC corresponding to each of these 11 volatile organic compounds.
Preferably, the content of each of these 11 volatile organic compounds, in particular the surface area of the chromatography peaks corresponding to the 11 volatile organic compounds, is compared to that of a reference protein-rich microalgal biomass composition or compositions for which the organoleptic qualities are defined, especially as unacceptable or acceptable.
The present invention also relates to a method for defining an analytical profile of volatile organic compounds making it possible to evaluate the organoleptic quality of the protein-rich microalgal biomass compositions, comprising:
Preferably, the microalgal biomass comprises more than 50% proteins by dry weight of biomass and the microalgae are of the Chlorella genus.
Preferably, the descriptors of the sensory analysis comprise:
Finally, the present invention relates to selecting 4 of the 11 volatile organic compounds having a low olfactory threshold (that is to say having a major impact on the overall odor perceived by the members of the sensory panel), in order to construct a simplified model which makes it possible to give an overall flavor value to the protein-rich microalgal biomass compositions. Thus, the invention relates to a method for determining the organoleptic quality of a protein-rich microalgal biomass composition, comprising determining the content of 4 volatile organic compounds, these 4 organic compounds being 3,5-octadien-2-ol (or 3-octen-2-one), 1-octen-3-ol, 3,5-octadien-2-one and (E,E)-2,4-nonadienal.
This overall flavor value is then expressed as the sum of the individual flavor values of 3,5-octadien-2-ol (or 3-octen-2-one), 1-octen-3-ol, 3,5-octadien-2-one and (E,E)-2,4-nonadienal.
Preferably, the microalgal biomass comprises more than 50% proteins by dry weight of biomass and the microalgae are of the Chlorella genus.
The protein-rich microalgal biomass compositions in accordance with the invention thus have an optimized sensory profile when their overall flavor value is low, preferably between 0 and 40% relative to that of an organoleptically unacceptable reference microalgal flour composition.
The present invention also relates to a method for selecting protein-rich microalgal biomass compositions having an acceptable organoleptic profile, characterized in that the organoleptic quality is determined by the method as described above, and that the composition is selected when the overall flavor value calculated by the method as described above is between 0 and 40% relative to that of an organoleptically unacceptable reference microalgal biomass composition. Preferably, the microalgal biomass comprises more than 50% proteins by dry weight of biomass and the microalgae are of the Chlorella genus.
Preferably, the microalgae are of the Chlorella genus and are chosen in particular from the group consisting of Chlorella vulgaris, Chlorella sorokiniana and Chlorella protothecoides, and more particularly Chlorella protothecoides.
Preferably, the microalgal biomass comprises more than 50% proteins by dry weight of biomass.
For the purposes of the invention, a protein-rich microalgal biomass composition has an “optimized sensory profile” or an “optimized organoleptic quality” when its evaluation by a sensory panel concludes that there is an absence of off-notes which impair the organoleptic quality of said food formulations containing these microalgal biomass compositions.
The term “organoleptic quality” is intended to mean the property of a food in terms of color and odor.
These off-notes are associated with the presence of undesirable specific odorous and/or aromatic molecules which are characterized by a perception threshold corresponding to the minimum value of the sensory stimulus required to arouse a sensation.
The “optimized sensory profile” or “optimized organoleptic quality” is then reflected by a sensory panel by obtaining the best scores on a scale of evaluation of the 2 sensory criteria (color and odors).
The term “approximately” is intended to mean the value plus or minus 10% thereof, preferably plus or minus 5% thereof. For example, “approximately 100” means between 90 and 110, preferably between 95 and 105.
The term “microalgal biomass composition” is intended to mean a composition comprising at least 50%, 60%, 70%, 80% or 90% by dry weight of microalgal biomass. However, other ingredients can optionally be included in this composition.
The term “protein-rich” is intended to mean a proteins content in the biomass of more than 50% by dry weight, preferably more than 55%, more preferably still more than 60%, 65% and 70% by dry weight of biomass.
For the purposes of the present invention, the term “microalgal biomass” should be understood in its broadest interpretation and as denoting, for example, a composition comprising a plurality of particles of microalgal biomass. The microalgal biomass is derived from whole microalgal cells.
A certain number of prior art documents, such as international patent application WO 2010/045368, describe methods for the production and use in food of protein-rich Chlorella microalgal biomass.
The microalgae in question in the present invention are therefore microalgae of the Chlorella genus, more particularly Chlorella protothecoides, more particularly still Chlorella deprived of chlorophyll pigments, by any method known per se to those skilled in the art (either because the culture is carried out in the dark, or because the strain has been mutated so as to no longer produce these pigments).
In particular, the microalgae can be chosen, non-exhaustively, from Chlorella protothecoides, Chlorella kessleri, Chlorella minutissima, Chlorella sp., Chlorella sorokiniana, Chlorella luteoviridis, Chlorella vulgaris, Chlorella reisiglii, Chlorella ellipsoidea, Chlorella saccarophila, Parachiorella kessleri, Parachiorella Prototheca stagnora and Prototheca moriformis. Thus, in one quite particular embodiment, the microalgal biomass composition is a Chlorella biomass composition, and in particular a Chlorella protothecoides biomass composition.
The fermentative process described in this patent application WO 2010/045368 thus allows the production of a certain number of microalgal biomass compositions of variable sensory quality.
The method as described in the present document therefore makes it possible to select the protein-rich microalgal biomass compositions which have an acceptable organoleptic profile, especially for food applications, without having to organize organoleptic evaluations by a panel of individuals in order to do so.
1. Definition of the Sensory Profile by Detecting 11 Volatile Organic Compounds
The applicant company has discovered that the sensory profile of a protein-rich microalgal biomass composition can be defined by the nature and the threshold of detection of odorous specific molecules, in particular of specific volatile organic compounds.
Indeed, it has identified 11 volatile organic compounds, the content of which in a protein-rich microalgal biomass composition makes it possible to determine the organoleptic quality of said composition.
These 11 volatile organic compounds are the following: pentanal, hexanal, 1-octen-3-ol, 2-pentylfuran, octanal, 3,5-octadien-2-ol (or 3-octen-2-one), 3,5-octadien-2-one, nonanal, 2-nonenal, (E,E)-2,4-nonadienal and hexanoic acid.
Thus, the present invention relates to a method for determining the organoleptic quality of a protein-rich microalgal biomass composition, comprising determining the content of each of these 11 volatile organic compounds, the 11 volatile organic compounds being pentanal, hexanal, 1-octen-3-ol, 2-pentylfuran, octanal, 3,5-octadien-2-ol (or 3-octen-2-one), 3,5-octadien-2-one, nonanal, 2-nonenal, (E,E)-2,4-nonadienal and hexanoic acid.
The method does not exclude determining the content of other volatile organic compounds. However, the 11 volatile organic compounds are sufficient to determine the organoleptic quality of a protein-rich microalgal biomass composition.
Preferably, these volatile organic compounds are sampled by solid phase microextraction (SPME) and analyzed by gas chromatography GC, in particular by GC-MS (gas chromatography-mass spectrometry).
The volatile fraction is extracted from the sample of the protein-rich microalgal biomass composition by heating said composition for a sufficient period of time in the presence of an SPME fiber.
The fiber may, for example, be chosen, non-exhaustively, from the group consisting of carboxen and polydimethylsiloxane (CAR/PDMS), divinylbenzene, carboxen and polydimethylsiloxane (DVB/CAR/PDMS), an alloy of metal and of polydimethylsiloxane (PDMS), a Carbopack-Z® fiber (graphitized carbon black), polyacrylate, Carbowax® polyethylene glycol (PEG), and PDMS/DVB.
Preferably, a DVB/CAR/PDMS fiber (df 50/30 μm) is used.
Here, the applicant company recommends using a wet extraction technique (aqueous suspension) between 40 and 70° C., preferably between 50 and 65° C., in particular approximately 60° C. for at least 10 minutes, preferably at least 15 minutes and for example between 15 minutes and 1 hour.
Preferably, this extraction step is carried out in a sealed container. A sufficient amount of sample must be used, for example at least 1 g, especially between 1 g and 10 g and in particular approximately 2 g.
These 2 g are then suspended in 7 ml water containing 1 g CaCl2, 200 μl HCl and 2.32 μg hexanal-d12 (internal standard), placed in a sealed SPME flask (20 ml).
The volatile organic compounds are then desorbed at a temperature compatible with the type of SPME fiber used, for example between 220 and 250° C. for the fiber used in our tests, more precisely at 230° C., and injected into the analysis system.
Preferably, the analysis is carried out by gas chromatography GC, in particular by GC-MS.
Several GC/MS devices are commercially available, for example the GC/Mass Clarus spectrometer (PerkinElmer, USA), the Hewlett Packard 6890 gas chromatograph (Hewlett Packard, USA) and the Agilent 6890N gas chromatograph coupled to the Agilent 5973 selective mass detector.
The ionization methods which can be used in GC/MS are for example mass spectrometry with electron impact ionization (EI), chemical impact ionization (CI), electrospray ionization, luminescent discharge, field desorption (FD), etc.
The volatile substances extracted are more precisely desorbed here in the injector of the TSQ GC-MS system from Thermo Scientific, and then separated on a CPwax52 (60 m×0.25 mm, 0.25 μm) column with helium gas at 1.5 ml/min.
The temperature program is:
The detection is carried out by electron impact (EI) mass spectrometry (MS) and the compounds are identified by comparison with the EI spectra of the NIST library.
Thus, the height or the surface area of the chromatography peak corresponding to the volatile organic compound correlates with the amount of said compound.
The term “surface area of the peak” is intended to mean the surface area of a specific ion under the curve in the SPME-GC/MS chromatogram.
Preferably, the content of one of the 11 volatile organic compounds is determined by the surface area of the peak of the specific ion of the SPME-GC/MS chromatogram corresponding to this volatile organic compound.
The content of volatile organic compounds is determined, especially in comparison with that of a reference product.
Thus, overall, a low total content of the 11 volatile organic compounds is associated with an optimized organoleptic quality. Conversely, a higher total content of the 11 volatile organic compounds is associated with a medium, or even poor or unacceptable, organoleptic quality.
For example, the total content of a composition with an acceptable organoleptic quality is low when it is at least two times less than that of a composition with an unacceptable organoleptic quality, for example at least 2, 3 or 4 times less, and in a most demanding embodiment, at least 10 times less.
2. Definition of the Sensory Panel and Choice of Descriptors
The present invention relates to a method for testing the organoleptic qualities of a protein-rich microalgal biomass composition comprising evaluation of the organoleptic qualities by a panel of testers. This evaluation can especially be carried out by the methods detailed below.
The applicant company also provides a method for defining an analytical profile of volatile compounds making it possible to evaluate the organoleptic quality of the microalgal biomass compositions, comprising:
A sensory panel is formed in order to evaluate the sensory properties of various batches of microalgal biomass compositions, in particular Chlorella protothecoides biomass compositions.
In order to evaluate the sensory properties of the protein-rich microalgal biomass compositions, a panel of at least 15 individuals, for example 18 individuals, was brought together.
This “expert panel” makes it possible to carry out analyses of the QDA® (Quantitative Descriptive Analysis) type, conventionally referred to as “sensory profiles” (Stone, H., Sidel, J-L., Olivier, S., Woolsey, A., Singleton, R. C; (1974), Sensory evaluation by quantitative descriptive analysis, Food Technology, 28(11), 24-33).
As clarified by standard NF ISO 11035: 1995, sessions for generating descriptors were undertaken in order to exhaustively describe the olfactory properties of the protein-rich microalgal biomass compositions.
For this purpose, batches of protein-rich microalgal biomass compositions identified as being highly heterogeneous were placed in solution at 3% in water.
Each panelist evaluates this solution in a closed glass jar which has been heated beforehand in a water bath to 55° C., and lists all the odors he or she senses from the product.
During the sessions for generating descriptors, more than 60 terms were listed by the judges to describe the odor of the protein-rich microalgal biomass compositions.
The list of descriptors was firstly reduced qualitatively (e.g: “lawn” odor=“cut grass” odor), in order to obtain a list of 16 descriptors, then some QDA® sessions enabled the list to be further reduced (cf: ISO 4121:1987) to 9 sensory descriptors.
Preferably, the reference products as presented in the following table are associated with each descriptor:
Since the “paint” descriptor was the most organoleptically discriminating, it is recommended by the applicant company to use it as the main descriptor in order to establish the sensory classification of the various batches of protein-rich microalgal biomass compositions produced.
Training the Panel
Various exercises were carried out in order to train the panel in the use of intensity scales for each descriptor (NF ISO 08587:1992, ISO 08586-1:1993, ISO 08586-2: 1994).
The performance of the panel was finally validated by carrying out a profile exercise 3 times with the same batches of protein-rich microalgal biomass compositions; since the panel was considered to be discriminating, consensual and reproducible (method described in: Pages, J., Lê, S., Husson, F., Une approche statistiques de la performance en analyse sensorielle descriptive [A statistical approach to performance in descriptive sensory analysis], Sciences des aliments, 26(2006), 446-469), the tool can be used for the sensory analysis of the various batches of protein-rich microalgal biomass compositions, using the QDA® method.
Sensory Profile
The panel analyses each protein-rich microalgal biomass composition one after the other on intensity scales for each descriptor.
The questionnaire for one profile session (for 1 sample) is as follows:
Analyses of variance (ANOVAs) are carried out in order to evaluate the discriminating capacity of the descriptors (descriptors of which the p-value associated with the Fisher test is less than 0.20 for the Composition effect in the model Descriptor˜Composition+Panelist).
The Composition effect is interpreted as the discriminating capacity of the descriptors: if there is no effect (Critical Probability>0.20), the various batches of compositions were not discriminated according to this criterion.
The smaller the critical probability, the more discriminating the descriptor.
The paint descriptor stood out as one of the most significant descriptors for characterizing the acceptability of a batch; the grade obtained for this descriptor will serve for sensory classification.
This classification therefore then serves as a basis for studying the analytical profile of the volatile organic compounds and selecting molecules responsible for the poor organoleptic quality of the microalgal biomass compositions.
Thus, the profile of the volatile organic compounds of the microalgal biomass compositions is determined. It is determined by any method known to those skilled in the art, and preferably by SPME/GC-MS, as detailed above.
The analysis of the volatile compounds gives very complex GC-MS chromatograms, with a very large number of peaks. By means of analyses of variance and linear regressions, the volatile organic compounds which correlate best with the results obtained for the sensory matrix and with the paint odor.
Thus, an optimized organoleptic profile is associated and characterized by an analytical profile of volatile organic compounds.
In one preferred embodiment, the various organic compounds selected will be considered in terms of their total content, in comparison with reference compositions, especially as defined above. In particular, the total surface area of the chromatography peaks corresponding to the volatile organic compounds selected will be considered and compared.
3. Simplified Model Based on Four Volatile Organic Compounds Having an Impact on the Overall Odor
In this preferred embodiment, the applicant company found that it is advantageously possible to establish an overall flavor value for the protein-rich microalgal biomass compositions having an optimized sensory profile, which overall value is based on 4 volatile organic compounds chosen from the 11 organic compounds identified above.
These volatile organic compounds are selected on the basis of their criterion of low olfactory threshold. The overall flavor value is then established according the relationship:
Overall flavor value=Σ□ of the individual flavor values of 3,5-octadien-2-ol (or 3-octen-2-one), 1-octen-3-ol, 3,5-octadien-2-one and (E,E)-2,4-nonadienal.
Total FV=ΣFV(3,5-octadien-2-ol), FV(1-octen-3-ol), FV(3,5-octadien-2-one), and FV[(E,E)-2,4-nonadienal],
where FV=Concentration of the compound x/olfactory threshold of the compound x
As will be shown in the examples below, the protein-rich microalgal biomass compositions having a low overall flavor value of between 0 and 40%, relative to that of an organoleptically unacceptable reference microalgal biomass composition, are certain to have an optimized sensory profile.
The invention will be understood more clearly from the examples which follow, which are intended to be illustrative and nonlimiting.
The perception of the protein-rich microalgal biomass composition is determined by solubilization in water, the neutral medium par excellence.
A sensory panel was therefore formed to evaluate, according to the methodology set out above, the sensory properties of various batches of biomass of protein-rich microalgae, prepared according to the teaching of patent application WO 2010/045368.
18 batches of microalgal biomass were tested: batch 11, batch 12, batch 14, batch 33, batch 34, batch 42, batch 43, batch 44, batch 54, batch 81, batch 82, batch 83, batch 84, batch 85, batch 92, batch 93, batch 111, batch 112.
The result of such characterization of the batches is given based on the highly characteristic descriptor of the odor of “paint”.
Data Processing:
The analyses were carried out using the R software (freely sold):
R version 2.14.1 (Dec. 22, 2011)
Copyright (C) 2011 The R Foundation for Statistical Computing
ISBN 3-900051-07-0
Platform: i386-pc-mingw32/i386 (32-bit)
The software is a working environment which requires the loading of modules containing the calculation functions.
The modules used for the processing of profile data are as follows:
The ANOVA shows significantly different results from one product to the next:
The mean values obtained, by product, are as follows:
The classification is thus as follows, in increasing order of “paint” grade:
batch 92>batch 111>batch 12>batch 112>batch 43>batch 44>batch 33>batch 11>batch 81>batch 14>batch 82>batch 34>batch 42>batch 93>batch 84>batch 54>batch 83>batch 85.
Batch 92 is therefore defined as the control for acceptable organoleptic quality for this paint descriptor.
Batch 85, for its part, is defined as the control for unacceptable organoleptic quality for this paint descriptor.
This organoleptic classification having now been established, it is possible, efficiently according to the invention, to analyze the SPME/GC-MS profile of these samples in order to identify the reference molecular targets that will make it possible to define the quality of the compositions produced.
In order to carry out the SPME/GC-MS analysis of the 18 various batches of microalgal biomass compositions, the process is carried out as indicated above in aqueous suspension.
Analysis of the Volatile Compounds on Products in Aqueous Suspension
The volatile compounds were analysed in aqueous suspension in order to reduce the matrix effect, and an internal standard was added.
Visually, as shown in
The first approach consists in comparing the chromatographic profiles, in integrating all the peaks between 3.2 and 35.0 min (TIC, “total ion current”), and in checking whether these “untreated” results enable a link to be made to the sensory classification.
The comparison of the chromatographic profiles and the integration of all the peaks between 3.2 and 35.0 min (TIC, “total ion current”)—see
Because of the high complexity of the chromatograms, it is difficult to visually distinguish acceptable products from unacceptable products.
The integration of the surface areas of the chromatograms also does not enable a clear distinction to be made between acceptable and unacceptable products.
Moreover, this approach with untreated data does not enable it to be known which volatile compound(s) is (are) responsible for the off-notes or undesirable tastes or odors, nor to specifically monitor their appearance, nor to have any information on how they are formed.
A second approach consisted in adding to the list of volatile organic compounds of the above model by listing the volatile compounds identified on the SPME/GC-MS chromatograms which appear to accompany the organoleptic classifications.
From the GC-MS-olfactometric analysis of six samples, certain volatile compounds stood out; predominantly aldehydes derived from the degradation of the lipid fraction of the protein-rich microalgal biomass compositions, which are apparently responsible for the off-notes or undesirable tastes or odors.
In this second approach, it was thus decided to monitor some of these molecules selected by GC-MS-olfactometry and GC-MS of the various products.
In order to select the representative volatile organic compounds, a series of analyses of variance is carried out so as to keep only the volatile organic compounds which actually differ from one composition to the other given the variability of the SPME-GC/MS measurement.
The model is the following: Volatile organic compound˜Composition; only the compounds for which the critical probability associated with the Fisher test is less than 0.05 are retained.
Two examples of ANOVA on the compounds 2-nonenal and 3,5-octadien-2-one are given here:
It appears on the first volatile organic compound (2-nonenal) that the composition effect is significant (critical probability <0.00025), which means that there is a significant difference between the products given the variability of the measurement.
On the second compound (3,5-octadien-2-one, peak 2), the composition effect is not significant (critical probability >0.05). Thus, for the study, 2-nonenal will be retained but 3,5-octadien-2-one will not.
After this first selection of volatile compounds, linear regression models are established: this involves explaining the “paint” variable by each compound one by one.
As many models as there are compounds are therefore constructed. The model is the following: Paint˜Compound.
In order to select the final list of compounds identified as responsible for the unacceptable organoleptic classifications (off-notes) observed, only the compounds for which the critical probability associated with Student's test is less than 0.05 (test for nullity of the linear regression coefficient) will be retained.
The R2 associated with the model is an indicator for quantifying the percentage of variability explained by the compound. It may not be very high, but significant; for this reason, it is chosen to select the compounds according to the critical probability (so as not to neglect a compound which has little but significant influence on the paint odor described by the panel).
Coefficients:
Coefficients:
For these 2 compounds, hexanal and 3,5-octadien-2-one (peak 1), the critical probability is lower than 0.05, therefore they are correlated with the paint odor described by the panel.
The 11 compounds of the study are found to be well correlated with the “paint” descriptor.
These 11 molecules selected are listed in the table below:
As shown in
The statistical analysis confirms that all 11 molecules are significant (except the second peak of 3,5-octadien-2-one at 21.24 min).
In conclusion, monitoring these 11 molecules (pentanal, hexanal, 1-octen-3-ol, 2-pentylfuran, octanal, 3,5-octadien-2-ol (or 3-octen-2-one), 3,5-octadien-2-one (first of the 2 peaks), nonanal, 2-nonenal, (E,E)-2,4-nonadienal, hexanoic acid) makes it possible to distinguish acceptable products from unacceptable products on the basis of the “paint” criterion, by analyzing the volatile substances of the product placed in aqueous suspension.
Creating the Simplified Model
In order to simplify the model, it is decided to retain the compounds having the greatest impact on the overall odor of the protein-rich microalgal biomass compositions according to the invention, that is to say the compounds with extremely low olfactory thresholds.
These individual flavor values (=concentration of the compound/olfactory threshold thereof) are represented in
Taking into account the concentration and the olfactory threshold of each compound, four compounds appear to be particularly important for the sensory properties of the protein-rich microalgal biomass compositions according to the invention: 3,5-octadien-2-ol or 3-octen-2-one (floral-zest), 1-octen-3-ol (mushroom-solvent, paint, mushroom-ink), 3,5-octadien-2-one (the first of the two peaks, floral), and (E,E)-2,4-nonadienal (oily-oxidized).
The individual descriptors of these four compounds bring together very well the overall perceived odor of the unacceptable protein-rich microalgal biomass compositions according to the invention.
It is therefore possible to establish an overall flavor value for the protein-rich microalgal biomass compositions based on these four compounds:
Overall flavor value=Σ of the individual flavor values of 3,5-octadien-2-ol (or 3-octen-2-one), 1-octen-3-ol, 3,5-octadien-2-one and (E,E)-2,4-nonadienal.
As shown in
It should be noted that batch 85, which is a batch of organoleptically unacceptable quality according to example 1, has a flavor value of 100%.
The acceptable batches therefore do indeed have an overall flavor value of between 0 and 40% compared to that of an unacceptable reference microalgal flour composition, in this case batch 85.
Batches 42, 93 and 54 have an overall flavor value, based on the four organoleptic compounds, far greater than that of the reference batch 85.
However, it should be noted that batch 85 was defined as unacceptable on the basis solely of the “paint” descriptor.
Batches 42, 93 and 54, in terms of the analysis of volatile organic compounds, are particularly affected, undoubtedly by a synergistic effect between volatile organic compounds.
This does not detract from the fact that the simplified model based on this selection of the 4 volatile organic compounds from the reference 11 makes it possible to classify the protein-rich microalgal biomass compositions into two distinct and easily identifiable families.
| Number | Date | Country | Kind |
|---|---|---|---|
| 13 57843 | Aug 2013 | FR | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/FR2014/052046 | 8/6/2014 | WO | 00 |
| Publishing Document | Publishing Date | Country | Kind |
|---|---|---|---|
| WO2015/019023 | 2/12/2015 | WO | A |
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| Email dated Nov. 3, 2015, from Gerald Suh of Solazyme, Inc., to Jeffrey M. Goehring of Young & Thompson International Patent & Trademark Law (counsel for Roquette Frères, S.A.). |
| Letter dated Oct. 6, 2015, from Jeffrey M. Goehring of Young & Thompson International Patent & Trademark Law (counsel for Roquette Frères, S.A.) to Gerald Suh of Solazyme, Inc., and R. James Balls and William E. McShane of Novak Druce Connolly Bove + Quigg LLP (counsel for Solazyme Roquette Nutritionals, LLC), which included the following enclosures: Exhibits 1, 9-12, and 14-15 to the Declaration of Jeffrey M. Goehring in Support of Roquette Frères, S.A.'s Brief in Support of its Motion for Summary Judgment of Solazyme, Inc.'s Claim for Misappropriation of Trade Secrets, Roquette Frères, S.A. v. Solazyme, Inc., C.A. No. 14-01442, District Court for the District of Delaware, D.I. 141, Jun. 22, 2015, Redacted Version; Exibits 2-8 to the Declaration for Jeffrey M. Goehring in Support of Roquette Frères, S.A.'s Brief in Support of its Motion for Summary Judgment of Solazyme, Inc.'s Claim for Misappropriation of Trade Secrets, Roquette Frères, S.A. v. Solazyme, Inc., C.A. No. 14/01442, District Court for the District of Delaware, D.I. 112-1, Jun. 22, 2015; Exhibit 13 to the Declaration of Jeffrey M. Goehring in Support of Roquette Frères, S.A.'s Brief in Support of its Motion for Summary Judgment of Solazyme, Inc.'s Claim for Misappropriation of Trade Secrets, Roquette Frères, S.A. v. Solazyme, Inc., C.A. No. 14-01442, District Court for the District of Delaware, D.I. 112-2, Jun. 22, 2015; Declaration of Jeffrey M. Goehring in Support of Roquette Frères, S.A.'s Brief in Support of its Motion for Summary Judgment of Solazyme, Inc.'s Claim for Misappropriation of Trade Secrets, Roquette Frères, S.A. v. Solazyme, Inc., C.A. No. 14-01442, District Court for the District of Delaware, D.I. 112, Jun. 22, 2015; Roquette Frères, S.A.'s Opening Brief in Support of its Motion for Summary Judgment of Solazyme, Inc.'s Claim for Misappropriation of Trade Secrets, Roquette Frères, S.A. v. Solazyme, Inc., C.A. No. 14-01442, District Court for the District of Delaware, D.I. 140, Jun. 22, 2015, Redacted Version. |
| Letter dated Nov. 2, 2015, from Jeffrey M. Goehring of Young & Thompson International Patent & Trademark Law (counsel for Roquette Frères, S.A.) to Gerald Suh of Solazyme, Inc., and R. James Balls and William E. McShane of Novak Druce Connolly Bove + Quigg LLP (counsel for Solazyme Roquette Nutritionals, LLC), which included the same enclosures included with the letter dated Oct. 6, 2015 of Cite No. CB. |
| Email dated Nov. 4, 2015, from Jeffrey M. Goehring of Young & Thompson International Patent & Trademark Law (counsel for Roquette Frères, S.A.) to Gerald Suh of Solazyme, Inc., and R. James Balls and William E. McShane of Novak Druce Connolly Bove + Quigg LLP (counsel for Solazyme Roquette Nutritionals, LLC). |
| Opinion dated Dec. 21, 2015 in Roquette Frères, S.A., v. Solazyme, Inc., Case No. 1:14-cv-01442 (D. Del. 2015) granting Solazyme's motion for an order confirming the arbitration award rendered by CPR International Institute for Conflict Prevention & Resolution on Feb. 19, 2015, in favor of Solazyme, Inc. |
| Youzhi Jiagong, (Jun. 8, 2007), “Oil Processing Technology (2nd edition)”, Chemical Undustry Press, Title page, Publication Page, Table of Contents, pp. 206-213, (in Chinese). |
| “Linoleic acid and α-linolenic acid are real essential fatty acids”, (Mar. 1998), Title page, Publication Page, Table of Contents, Chapter 2: Essential Fatty Acids (pp. 12-13) and Chapter 15: Selection of the most suitable fatty acids (pp. 89-91), with English translation. |
| Bowman, Barbara A. and Robert M. Russell (eds.), “Present Knowledge in Nutrition” (1st Edition), (Oct. 2004), Title page, Publication Page, Table of Contents, p. 231 (in Chinese). |
| “Auxenochlorella”, article from Wikipedia, Retrieved from the Internet on Mar. 23, 2016, “https://en.wikipedia.org/w/index.php?title=Auxenochlorella&oldid=711518993”. |
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| “Algen—Nudein ais Altmark Spezialitat (Algae noodles: a speciality from Altmark region)” in German language, and other Chlorella Food products, (Oct. 9, 2007), 3 pages. |
| IMAI, Ichiro, et al. “Advanced research on Shellfish poisonings: Current Status and overview”, Table of Contents, Chapters 1 and Chapter 4, 11 pages. |
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| Kay, Robert A., “Microalgae as Food and Supplement”, Critical Reviews in Food Sciense and Nutrition, 30(6):555-573 (Feb. 1991). |
| Usuki, Riichiro and Luniko Kamata,“Experimental Trials on the Role of Lipids in Good Taste and Good Body of Foods”, Research reports of Shokei Gakuin College 53, May 2006, p. 85-90 (in Japanese with English Abstract). |
| “Chlorella Photosynthesis—Disctionary”, last modified Mar. 23, 2015, Retrevied from the Internet: <URL: (http://photosyn.jp/pwiki/index.php?%E3%82%AF%E3%83%AD%E3%83%AC%E3%83%A9) with English Machine Translation. |
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| Oral Summary by the Patentee, dated Nov. 29, 2016, for Invalidation Hearing for Japanese Patent No. 5731982 (in Chinese). |
| USDA National Nutriet Database (https://ndb.nal.usda.gov/ndb/). |
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| “Roquestte Freres, S.A. and Solazyme, Inc. Agree to Dissolve Microalgae Join Venture”, (Jun. 24, 2013) Press Release, Lestrem, France. |
| Standard Tables of Food Composition in Japan 2015 (Seventh Revised Edition), Table of Fatty Acid Composition, Edited by the Council for Science and Technology, the Ministry of Education, Culture, Sports, Science and Technology, (available from http://www.mext.go.jp/a_menu/syokuhinseibun/1365295.htm) [Retreived from the Internet Oct. 12, 2016: <URL: (http://www.algomed.de/index.php?op=algenfarm_geschichte)]http://www.geocities.jp/jr2bvb/syokuhin/sibousan/oil_s.htm]. |
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| Roquette Freres S.A. v. Solazyme Inc., Delaware District Court, Case No. 1:14-cv-01442 District Judge Sue L. Robinson, presiding, Solazyme, Inc.'s Answer to Plantiff Roquette Freres, S.A.'s Complaint, Petition to Confirm Arbitration Award and Counterclaims, filed Feb. 26, 2015, 29 pages. |
| Joint Venture and Operating agreement of Solazyme Roquette Nutritionals, LLC., dated Nov. 7, 2015. |
| Solazyme, Inc. vs. Roquette Freres, S.A., Arbitration Award, dated Feb. 19, 2015. |
| Request for Invalidation, dated Jan. 7, 2015, for Chinese Patent Application No. 200980149978.1, 21 pages (in Chinese). |
| Supplemental Statement for Request for Invalidation, dated Dec. 2, 2015, for Chinese Patent Application No. 200980149978.1, 35 pages (in Chinese), including the list of submitted Counter Evidences on p. 1-2. |
| Notification of Acceptance of Request for Invalidation, dated Jan. 28, 2016, for Chinese Patent Application No. 200980149978.1, 4 pages (in Chinese). |
| Documents filed by the Petitioner—Part II, dated Apr. 29, 2015, for Chinese Patent Application No. 200980149978.1, 21 pages (in Chinese), including : Jia, Xuan, et al., “Removal of Total nitrogen form wastewater dischrage from a chemical pertilizer plant by Chlorella protothecoides USTB-01”, Chinese Journal of Environmental Engineering, (Apr. 2010), 4(4):737-740 (in Chinese). |
| Documents filed by the Petitioner—Part III, dated May 5, 2015, for Chinese Patent Application No. 2009801499781, 21 pages (in Chinese), including :, including : Singelton Paul and Diana Sainsbury, “Dictionary of Microbiological and Molecular Biology, (3rd Ed. 2006)”, pp. 155 (and Chinese translation thereof)—Singelton Paul and Diana Sainsbury, “Dictionary of Microbiological and Molecular Biology, (2nd Ed. 1987)”, pp. 178-179 (and Chinese translation therof). |
| Statement of Grounds & Particulars of Opposition, Grounds for Opposition, In the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Mar. 3, 2016, (21 pages). |
| Declaration of Michael Armin Borowitzka in the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. And Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Jun. 2, 2016, (32 pages). |
| Exhibit MB-1, Federal Court of Australia, Practice Note CM7, Expert Witnesses in Proceedings on the Federal Court of Australia, commenes Jun. 4, 2013; Exhibit MB-2, Michael Armin Borowitzka Curriculum Vitae; Exhibit MB-3, J. M. Hundley, R. B. Ing and R. W. Krauss, “Algae as Sources of Lysine and Threonine in Supplementing Wheat and Bread Diets”, Science, New Series, Vol. 124, No. 3221 (Sep. 21, 1956), pp. 536-537.; Exhibit MB-4, Krauss, Robert W., “Mass Culture of Algae for Food and Other Organic Compounds,” American Journal of Botany, vol. 49, No. 4 (Apr. 1962), pp. 425-435.; Exhibit MB-6, Soong, Pinnan, “Productions and Development of Chlorella and Spirulina in Taiwan”, Algae Biomass: Production and Use, Gedaliah Shelef and Carl J. Soeder (eds.), North-Holland Biomedical Press, (Dec. 1980), pp. 97-113 and title and copyright page.; Exhibit MB-7, Kawaguchi, Kotaro, “Microalgae Production Systems in Asia”, Algae Biomass: Production and Use, Gedaliah Shelef and Carl J. Soeder (eds.), North-Holland Biomedical Press, (Dec. 1980), pp. 25-33 and title and copyright page.; Exhibit MB-8, Kay, Robert A., “Microalgae as Food and Supplement”, Critical Reviews in Food Sciense and Nutrition, 30(6):555-573 (Feb. 1991).; Exhibit MB-9, Raymundo et al., “Fat mimetic capacity of Chlorella vulgaris biomass in oil-in-water food emulsions stabilized by pea protein,” Food Research International, 38:961-965, (Feb. 25, 2005).; Exhibit MB-10, Samejima, H. and J Myers, “On the Heterotrophic Growth of Chlorella pyrenoidosa”, J. Gen Microbiol, (1958), 18:107-117. |
| Exhibit MB-11, Aoki, Shigeji and Eiji Hase, “De- and Re-Generation of Chloroplasts in the Cells of Chlorella Protothecoides”, Plant & Cell Physiol, (Sep. 5, 1964), vol. 5, pp. 473-484 [Retreived from the internet on Jun. 7, 2013 from http://pcp.oxfordjournals.org/ by Reprints Desk ].; Exhibit MB-12, Becker, E.W., “Micro-algae as a source of protein,” Biotechnology Advances, 25:207-201, (Mar.-Apr. 2007).; Exhibit MB-13, Iwamoto, Hiroaki, “Industrial Production of Microalgal Cell-mass and Secondary Products—Major Industrial Species Chlorella”, Chapter 11, Handbook of Microalgal Culture: Biotechnology and Applied Phycology, Amos Richmond (eds), (Dec. 1, 2003), pp. 255-263.; Exhibit MB-14, Petkov et al., “Which are fatty acids of the green alga Chlorella?,” Biochemical Systematics and Ecology, 35:281-285, (2007).; Exhibit MB-15, Gladu, Patricia K., et al. “Sterol, Fatty Acid and Pigment Characteristics of UTEX 2341, a Marine Eustigmatophyte Identified Preivously as Chlorella Minutissuma (Chlorophyceae)” J. Phycol., (Jun. 21, 1995), 31:774-777.; Exhibit MB-16, Xu et al., “High Quality Biodiesel Production From a Microalga Chlorella Protothecoides by Heterotrophic Growth in Fermenters,” Journal of Biotechnology, 126(4):499-507, (May 2006).; Exhibit MB-17, Matsuka et al., “Changes in Contents of Carbohydrate and Fatty Acid in the Cells of Chlorella Protothecoidesduring the process of De- and Re-Generation of Chloroplasts,” Plant and Cell Physiol., 7:651-662 (Sep. 24, 1966).; Exhibit MB-18, Xuan, J. et al., “Removal of total nitrogen from wastewater discharge from a chemical fertilizer plant by Chlorela protothecoides USTB-01”, Chinese Journal of Environmental Engineering, (Apr. 2010), vol. 4, No. 4, pp. 737-740. |
| Exhibit MB-19, Australian Application No. 2009303354B2 from International Patent Application No. PCT/US2009/060692, naming Solazyme, Inc., International Patent Publication No. 2010/045368, dated Apr. 22, 2010.; Exhibit MB-20, Pabst, W., “Nutritional evaluation of nonsewage microalgae by the rat balance method,” Arch. HyrobioL Beih, (Dec. 1978), pp. 65-70; Exhibit MB-21, Urano, et al., “Effect of Osmotic Stabilizers on Protoplast Generation on Chlorella ellipsoidea Yellow/White Color Mutants”, Journal of Bioscience and Bioengineering, vol. 90, No. 5, 567-569, (2000).; Exhibit MB-22, Kamiya, “Effects of Blue Light and Ammonia on Nitrogen Metabolism in a Colorless Mutant of Chlorella”, Plant Cell Phyiol., 30(4):513-521 (1989); Exhibit MB-23, Biello et al., “Biofuel of the Future: Oil from Algae,” Scientific American, 2 pages, (Jan. 9, 2008). |
| Evidence in Support, In the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A.v. Solazyme, Inc., Commonweath of Ausralia, Jun. 3, 2016, (1 page). |
| Declaration of Young J. Suh in the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. And Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Aug. 31, 2016, (94 pages); Exhibit YS1, Arbitration Award, Solazyme Inc. vs. Roquette Frères, Case 1:14-cv-01442-SLR, Document 153, Filed Dec. 21, 2015; Exhibit YS2, French Patent Publication No. FR 2 924 126, filed Nov. 28, 2007.; Exhibit YS3, Memorandum Opinion, Document 153, Roquette Frères, S.A. vs. Solazyme Inc., Case 1:14-cv-01442-SLR, filed Dec. 21, 2015. |
| Declaration of Craig Patch in the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Sep. 5, 2016, (22 pages); Exhibit CP-1, Federal Court of Australia, Practice Note CM7, Expert Witnesses in Proceedings on the Federal Court of Australia, commenes Jun. 4, 2013.; Exhibit CP-2, Craig Patch Curriculum Vitae. |
| Declaration of Craig Patch in the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Sep. 28, 2016, (42 pages).; Exhibit CP3, Record of Views Formed in Response to Inquires, updated Mar. 2015 (20 pages); Exhibit CP4, Huss, V.A.R., et al., “Biochemical Taxonomy and Molecular Phylogeny of the Genus Chlorella Sensu Lato (Chlorophyta)1”, J. Phycol. 35, 587-598 (Jan. 15, 1999). |
| Evidence in Answer, In the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Sep. 29, 2016, (1 page). |
| Declaration of Michael Armin Borowitzka In the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Dec. 21, 2016, (14 pages). |
| Evidence in Reply, In the matter of Australian Patent Application No. 2009303354 in the name of Solazyme, Inc. and Opposition by Roquette Frères, S.A. v. Solazyme, Inc., Commonweath of Ausralia, Dec. 23, 2016, (1 page). |
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| Evidence 1, Explanation paper, filed with IP High Court Case No. H29 (gyo-ke) 10149 on Oct. 6, 2017 in Invalidation Appeal No. 2016-800012 against Japanese Patent No. 5731982, with English translation. |
| First Statement, Substantive Brief, filed with IP High Court Case No. H29 (gyo-ke) 10149 on Nov. 17, 2017 in Invalidation Appeal No. 2016-800012 against Japanese Patent No. 5731982, with English translation. |
| Second Statement, Substantive Brief, filed with IP High Court Case No. H29 (gyo-ke) 10149 on Jan. 17, 2018 in Invalidation Appeal No. 2016-800012 against Japanese Patent No. 5731982. With Explanation Paper for the Evidence. Japanese Only. |
| Opponent'S Outline of Submissions, in the Matter of Australian Patent Application No. 2009303354 in the name of Corbion Biotech, Inc., dated Jan. 24, 2018, 48 pages. |
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| Number | Date | Country | |
|---|---|---|---|
| 20160195503 A1 | Jul 2016 | US |
