WO2022058581A1

WO2022058581A1 - Method for treating hemp and product obtained

Info

Publication number: WO2022058581A1
Application number: PCT/EP2021/075771
Authority: WO
Inventors: Rene SCHEPENS; David KRENBRINK; Ruben VAN MARIS
Original assignee: Dmas BV
Current assignee: Dmas BV
Priority date: 2020-09-19
Filing date: 2021-09-20
Publication date: 2022-03-24
Anticipated expiration: 2023-03-19

Abstract

The present invention relates to a process for providing a composition comprising one or more cannabinoid compounds from a plant material selected from the cannabaceae family, the method comprises the steps of (i) providing a plant material from the cannabaceae family; (ii) adding one or more lactic acid bacteria strains to the plant material, providing a fermenting medium; (iii) allowing the fermenting medium to ferment for at least 1 hour providing a fermented composition; and (iv) optionally, subjecting the fermented composition to one or more separation processes providing an isolated cannabinoid composition, wherein the plant material is selected from the flowers of the plant material; the (top) leaves of the plant material; the stem of the plant material; or the combination of the flowers, leaves and the stem of the plant material.

Description

METHOD FOR TREATING HEMP AND PRODUCT OBTAINED

Technical field of the invention

The present invention relates to a new process for preparing a cannabinoid composition and to the cannabinoid composition as such. In particular, the present invention relates to a process for fermenting a plant material selected from the cannabaceae family, such as hemp (or industrial hemp), using lactic acid bacteria providing an improved cannabinoid composition.

Background of the invention

Hemp, or industrial hemp, is a variety of the Cannabis sativa plant species that is grown specifically for the industrial uses of its derived products and it is one of the fastest growing plants.

Hemp was one of the first plants to be cultivated by humans, it is grown on fields since the Neolithic times. Main purpose to grow was to use the fibre from the stem in fabric, rope and paper. But also, its recreational use in a smoking pot to get the hallucinating effect of THC (tetrahydrocannabinol, which is the principal psychoactive constituent of cannabis) is known since thousands of years.

More recently cannabinoids other than THC have been discovered to have strong potential effects in medicine or as prophylaxis. Especially CBD (cannabidiol) is a cannabinoid which is getting more and more public and scientific interest because of its positive effects on human well-being.

CBD interacts with the human endo-cannabinoid system and many effects have been claimed over time, some with scientific proof and others with less scientific backup. To name a few effects, it is said to be an effective pain relief agent, it reduces anxiety, insomnia, depression. It can prevent diabetes, acne and other skin conditions. It is said to inhibit the formation and growth of tumours and help overcome addiction problems to several compounds. In addition to CBD, other interesting relevant cannabinoid compounds are found in hemp, such as cannabidivarin (CBDV); cannabigerol (CBG); cannabinol (CBN); or cannabichromene (CBC) and these are traditionally extracted as oils.

In the hemp plant, in particular in the flowers, CBD, as well as other interesting cannabinoid compounds such as CBDV; CBG; CBN; or CBC are found as water soluble acids (CBD-A, CBDV-A; CBG-A; CBN-A; CBC-A; THC-A, etc), which e.g. by the action of heat and/or enzymes, e.g. CBD-A is converted to CBD.

Traditionally the harvested hemp is dried to preserve the plants and keep them from spoilage, as well as to get the water out of the material to limit dilution of organic solvents applied in the later extraction of cannabinoids.

During the drying process, majority of the cannabinoid acids are decarboxylated and converted to the oil forms of cannabinoids.

One of the challenges of the oil forms of cannabinoids is that the human digestive tract does not absorb the fatty forms of the cannabinoids very well. It is assumed that at most 10-15% of the cannabinoids oil ingested, are taken up into the blood stream and get to the place where their effect will become apparent.

Furthermore, CBD may cyclize to THC under acidic conditions using intramolecular cyclization and it has been assumed that consuming CBD-oils may in the gastric acids convert CBD into THC providing a psychoactive or hallucinating effect. This conversion is undesirable because THC is an illegal compound to sell and market.

In addition to the impaired functional effects caused by the traditionally used processes for providing CBD products, the production of CBD products also face a challenge with the short production periods as fresh hemp needs to be processed within one day to avoid spoilage and loss of the hemp. Hemp is a seasonal crop which is harvested once a year and dried as mentioned above, resulting in a conversion from CBD- A to CBD, which is extracted as an oil. To avoid spoilage, the freshly harvested hemp should be processed soon after harvest which requires an enormous machinery and process equipment, mainly drying equipment, to be available to fractionize and dry the plant material. The dried plant material may be stored before the cannabinoid compounds are extracted. Such enormous machinery and process equipment would then stand unused the rest of the year, or need to be carefully cleaned and adjusted for use in other purposes for the rest of the year.

Hence, an improved process of providing cannabinoids and cannabinoid acids would be advantageous, and in particular a more efficient; consistent; faster; reproducible and cost effective (financially and/or environmentally) and/or reliable process of producing and providing these compounds.

Hence, an improved process and a cannabinoid composition would be advantageous. In particular, a new process which expands the processing period; which is fast; more environmentally friendly; efficient; reliable; cheap; reproducible; and provides a cannabinoid composition which is easily absorbed and/or has a strong binding efficiency to specific serotonin receptors.

Summary of the invention

Thus, an object of the present invention relates to a process for preparing a cannabinoid composition and to the cannabinoid composition as such.

In particular, it is an object of the present invention to provide a process for fermenting a plant material selected from the cannabaceae family, such as hemp (or industrial hemp), using lactic acid bacteria providing a cannabinoid composition having improved properties and that solves the above mentioned problems of the prior art with speed; efficiency; reliability; the environment; costs; reproducibility; and a cannabinoid composition which is poorly absorbed and/or has weak binding efficiency to specific serotonin receptors or the need for high dosages.

Thus, one aspect of the invention relates to a process for providing a composition comprising one or more cannabinoid compounds from a plant material selected from the cannabaceae family, the method comprises the steps of:

(i) providing a plant material from the cannabaceae family;

(ii) adding one or more lactic acid bacteria strains to the plant material, providing a fermenting medium;

(iii) allowing the fermenting medium to ferment for at least 1 hour providing a fermented composition; and (iv) optionally, subjecting the fermented composition to one or more separation processes providing an isolated cannabinoid composition.

Another aspect of the present invention relates to a fermented composition obtainable by the process according to the present invention.

Yet another aspect of the present invention relates to a fermented composition comprising one or more cannabinoid compound and one or more lactic acid bacterial strain or a derivative of one or more lactic acid bacterial strain.

Still another aspect of the present invention relates to an isolated cannabinoid composition obtainable by a process according to the present invention.

An additional aspect of the present invention relates to an isolated cannabinoid composition comprising one or more cannabinoid compound; one or more lactic acid bacterial strain or a derivative of one or more lactic acid bacterial strain; and less than 10% (w/w) fibrous material.

Yet an aspect of the present invention relates to the use of the fermented composition according to the present invention and/or the isolated cannabinoid composition according to the present invention as an ingredient in a beverage or a food product.

Another aspect of the present invention relates to a beverage comprising the fermented composition according to the present invention and/or the isolated cannabinoid composition according to the present invention.

An even further embodiment of the present invention relates to a food product comprising the fermented composition according to the present invention and/or the isolated cannabinoid composition according to the present invention.

Yet an aspect of the present invention relates to a fermented composition according to the present invention for use as a medicament.

A further aspect of the present invention relates to a fermented composition or an isolated cannabinoid composition according to the present invention for use in the treatment of nausea, anxiety, Chronic pain, Multiple sclerosis, vomiting, no or suppressed appetite, Gilles de la Tourette syndrome, Glaucoma Cancer, Epilepsy, Inflammatory bowel diseases, Parkinson's disease, Psychiatric disorders (taken from Bedrocan), Mood disorders, depression, co-morbid anxiety, other psychiatric disorders and bipolar disorders.

An even further aspect of the present invention relates to the use of the fermented composition according to the present invention or the isolated cannabinoid composition according to the present invention for the preparation of a phytoceutical, a nutraceutical or a health product.

The present invention will now be described in more detail in the following.

Detailed description of the invention

Accordingly, as mentioned above cannabinoid compounds, like CBD, are hydrophobic, meaning it will not dissolve, or dissolve poorly in water. As a result, cannabinoid compounds, like CBD oil absorbs poorly into the bloodstream, resulting in the majority are being flushed from the body without ever having an active effect.

Unlike CBD, CBD-A (cannabidiol-acid) is water soluble, the naturally occurring in plant materials selected from the cannabaceae family, however, CBD-A is unstable. CBD-A is considered being up to a thousand times more potent than CBD in binding to a specific serotonin receptor. Among other things, this receptor is said to be responsible for the relief of nausea and anxiety.

Combination of CBD and CBD-A may also increase the effects and/or bioavailability of CBD.

An aspect of the present invention relates to a process for providing a composition comprising one or more cannabinoid compounds from a plant material selected from the cannabaceae family, the method comprises the steps of:

(i) providing a plant material from the cannabaceae family;

In the context of the present invention the term "cannabinoid compounds" relates to complex chemical compounds found in cannabis and isolated from a plant material selected from the cannabaceae family.

In the context of the present invention, the term "fermented composition" relates to the controlled fermentation of a plant material. In the present context, the term "controlled fermentation" relates to a fermentation process where mainly growth of desired bacteria is initiated and where growth of moulds, yeast and pathogenic bacteria are avoided or substantially avoided.

Step (i) of the process according to the present invention relates to providing a plant material from the cannabaceae family.

Plant materials from the cannabaceae family relates to any plant material comprising one or more cannabinoid compounds. Specifically, plant materials from the cannabaceae family may comprises a small family of flowering plants and includes about 170 species grouped in about 11 genera, including cannabis (hemp, industrial hemp and marijuana).

In an embodiment of the present invention the plant material selected from the cannabaceae family may be selected from a cannabis genus.

In a further embodiment of the present invention the plant material selected from the cannabaceae family may be selected from a cannabis species selected from Cannabis saliva Cannabis indica; Cannabis ruderals; or a combination hereof.

While the entire plant may be used the plant material may preferably be selected from the flowers of the plant material; the (top) leaves of the plant material; the stem of the plant material; or the combination of the flowers, leaves and the stem of the plant material. Preferably, the plant material may be the flowers and/or the leaves.

In an embodiment of the present invention the plant material may be subjected to a pretreatment before the lactic acid bacterial strain is added in step (ii). Preferably, the pretreatment comprising grinding, cutting, chopping, slicing, and/or fractionizing of the plant material. The extend of the pre-treatment may result in a plant material having an average particle size of 50 mm or less, such as an average particle size of 30 mm or less, such as an average particle size of 20 mm or less, such as an average particle size of 10 mm or less such as an average particle size in the range 1-40 mm; such as in the range of 10-30 mm, e.g. in the range of 20-25 mm.

In yet an embodiment of the present invention the plant material provided in step (i) may preferably be a fresh plant material.

In the context of the present invention, the term "fresh" relates to plant materials which has not been subjected to freezing; heat processing; or drying.

In an embodiment of the present invention the plant material may be provided in step (i) as a fresh plant material within 1 month from harvest; such as within 20 days from harvest; e.g. within 10 days from harvest; such as within 5 days from harvest; e.g. within 3 days from harvest; such as within 1 days from harvest; e.g. within 20 hours from harvest; such as within 15 hours from harvest; e.g. within 10 hours from harvest; such as within 5 hours from harvest; e.g. within 3 hours from harvest; such as within 2 hours from harvest.

In an embodiment of the present invention the plant material provided in step (i) may not have been subjected to drying and/or the plant material may not have been subjected to a temperature above 110°C, e.g. above 100°C; such as above 90°C; e.g. above 80°C; such as above 70°C; e.g. above 60°C; such as above 50°C.

Due to the resistance socially and regulatory the plant material may preferably not be a modified plant material, such as a genetically modified plant material.

In an embodiment of the present invention the plant material may be a modified plant material, such as a genetically modified plant material.

Preferably, the plant material may not be subjected to any pasteurisation; sterilization; or the like before being subjected to the fermentation process in step (iii) providing the composition comprising one or more cannabinoid compounds.

The plant material selected from the cannabaceae family according to the present invention is characterised by being a plant material comprising one or more cannabinoid compound. In an embodiment of the present invention the one or more cannabinoid compound comprises cannabidiol (CBD); cannabidiol-acid (CBD-A); cannabidivarin (CBDV); cannabidivarin-acid (CBDV-A); cannabigerol (CBG); cannabigerol-acid (CBG-A); cannabinol (CBN); cannabinol-acid (CBN-A), cannabichromene (CBC); cannabichromene-acid (CBC- A); or a mixture thereof. Preferably, the one or more cannabinoid compound comprises (mainly comprise) cannabidiol-acid (CBD-A); cannabidivarin-acid (CBDV-A); cannabigerol- acid (CBG-A); cannabinol-acid (CBN-A); cannabichromene-acid (CBC-A); or a mixture thereof.

In the context of the present invention the term "mainly comprise" relates to a content of 50% or more based on the weight of all cannabinoid compounds in the composition; such as 60% or more; e.g. 70% or more; such as 80 or more.

In an embodiment of the present invention the one or more cannabinoid compound comprises one or more cannabidiol; preferably, cannabidiol-acid (CBD-A).

In yet an embodiment of the present invention the composition comprising one or more cannabinoid compound consists essentially of one or more cannabidiol; preferably, cannabidiol-acid (CBD-A).

In a further embodiment of the present invention the composition according to the present invention comprises a content of cannabinoid compound, such as CBD-A, of at least 0.5% (w/w) based on the weight of all cannabinoids in the composition; such as at least 1% (w/w), such as at least 2% (w/w), e.g. at least 3% (w/w), such as at least 4% (w/w), e.g. at least 6% (w/w), such as at least 10% (w/w), such as at least 25% (w/w), e.g. at least 35% (w/w), such as at least 50% (w/w), such as at least 75% (w/w).

The composition comprising one or more cannabinoid to the present invention may comprise a range of non-cannabinoid compounds. Without being bound by theory, it is believed that this complex mixture of constituents in the fermented composition may add to the beneficial effects of the composition of the present invention.

In an embodiment of the present invention the composition in addition to the presence of the one or more cannabinoid compound as defined herein comprises one or more a terpene. Preferably, the composition according to the present invention, wherein the one or more terpenes provides a terpene profile.

In an embodiment of the present invention the terpene profile of the composition according to the present invention may be preserved, or may be substantially preserved, relative to the terpene profile of the plant material before fermentation.

In the present context the term "substantially preserved" when talking about the terpene profile, relates to at least 50% of the one or more terpene, such as the terpene profile, present in the plant material may be preserved in the fermented plant material, such as at least 60%, e.g. at least 70%, such as at least 80%, e.g. at least 90%, such as at least 95%, e.g. at least 98%.

The Inventors of the present invention found that by preserving the one or more terpene (e.g. the terpene profile) and the cannabinoid composition, preferably the cannabidiol-acid, a synergistic medical effect or an entourage effect may be observed.

In the present context the term "composition" relates to both the fermented composition of the present invention and the isolated cannabinoid composition of the present invention, if not further specified.

Since the concentration of tetrahydrocannabinol compounds (THC/THC-A) in high concentrations is illegal (the specific concentration is dependent on national legislation and application), it is desirable to limit the content of tetrahydrocannabinol compounds (THC/THC-A) in the composition of the present invention.

In an embodiment of the present invention the content of tetrahydrocannabinol compounds (THC/THC-A) in the composition is below 50% (w/w) based on the weight of all cannabinoids in the composition, in particular relative to the content of the cannabinoid compound, such as below 25% (w/w); e.g. below 10% (w/w); such as below 5% (w/w); e.g. below 3% (w/w); such as below 1% (w/w); e.g. below 0.5% (w/w); such as below 0.3% (w/w).

In yet an embodiment of the present invention the ratio of the content of tetrahydrocannabinol compounds (THC/THC-A) relative the content of cannabidiol compounds (CBD/CBD-A) in the composition is 1 : 1 or less; such as 1 :2 or less; e.g. 1 :3 or less; such as 1:4 or less; e.g. 1 : 5 or less; such as 1 : 10 or less; e.g. 1 :25 or less; such as 1 : 50 or less; e.g. 1 :75 or less; such as 1 : 100 or less. In the context of the present invention the terms "(THC/THC-A)" and "(CBD/CBD-A)" relates to the combination of THC and THC-A and CBD and CBD-A, respectively.

In more specific embodiments, the compositions of the present invention comprises greater than 50% (w/w) CBD and/or CBDA, based on the weight of all cannabinoids in the compositions or products, greater than 60% (w/w), greater than 70% (w/w), greater than 80% (w/w), greater than 90% (w/w), greater than 95% (w/w), greater than 97% (w/w), greater than 99% (w/w), or greater than 99.5% (w/w)CBD and/or CBDA, based on the weight of all cannabinoids in the compositions or products.

The composition according to the present invention may comprise a ratio of the content of tetrahydrocannabinol (THC/THC-A) relative the content of cannabidiol (CBD/ CBD-A) of 1 : 1 or less; such as 1 :2 or less; e.g. 1 :3 or less; such as 1:4 or less; e.g. 1 : 5 or less; such as 1 : 10 or less; e.g. 1 :25 or less; such as 1 : 50 or less; e.g. 1 :75 or less; such as 1 : 100 or less.

In a further embodiment of the present invention, the composition comprises less than 3% (w/w) THC and THCA, based on the weight of all cannabinoids in the compositions or products, when analyzed using high performance liquid chromatography (HPLC), less than 2% (w/w), less than 1% (w/w), less than 0.5% (w/w), less than 0.1% (w/w), less than 0.01% (w/w), less than 0.004% (w/w), or less than 0.001% (w/w).

Analyzing the composition according to the present invention for the content of one or more cannabinoid compounds, such as CBD; CBD-A; THC; or THC-A may be done e.g. using HPLC (High-performance liquid chromatography).

Step (ii) of the process according to the present invention relates to adding one or more lactic acid bacteria strains to the plant material, providing a fermenting medium.

Lactic acid bacterial are important bacteria and are widely used, in particular in the food, beverage and feed industry. The importance of the lactic acid bacteria may be evidenced by their generally regarded as safe (GRAS) status, due to their ubiquitous appearance in food, beverages, and feeds and their contribution to the healthy microflora of human mucosal surfaces. The genera that comprise the lactic acid bacteria, and which may be used in the present invention, are Lactobacillus, Leuconostoc, Pediococcus, Lactococcus, and Streptococcus, Aerococcus, Carnobacterium, Enterococcus, Oenococcus, Teragenococcus, Vagococcus, and Weisella; these genera belong to the order Lactobacillales. In an embodiment of the present invention the one or more lactic acid bacterial strain added in step (ii) and/or the one or more lactic acid bacterial strain present in the fermented composition and/or the one or more lactic acid bacterial strain present in the isolated cannabinoid composition, may be selected from the group consisting of Lactobacillus, Leuconostoc, Pediococcus, Lactococcus, Streptococcus, Aerococcus, Carnobacterium, Enterococcus, Oenococcus, Teragenococcus, Vagococcus, and Weisella.

Preferably, the one or more lactic acid bacterial strain provided in step (ii) and/or the one or more lactic acid bacterial strain present in the fermented composition and/or the one or more lactic acid bacterial strain present in the isolated cannabinoid composition is one ore more lactic acid bacteria of the genus Enterococcus, Lactobacillus, Pediococcus, Lactococcus, or a combination thereof.

In an even further embodiment of the present invention the one or more lactic acid bacteria stain provided in step (ii) and/or the one or more lactic acid bacterial strain present in the fermented composition and/or the one or more lactic acid bacterial strain present in the isolated cannabinoid composition may be selected from the group consisting of one or more Enterococcus spp., Lactobacillus spp., Lactococcus spp., Pediococcus spp., and a combination hereof. Preferably, the one or more lactic acid bacterial strain is selected from the group consisting of one or more of Enterococcus faecium, Lactobacillus rhamnosus, Lactobacillus plantarum, Pediococcus acidililactili, Pediococcus pentosaceus, Lactococcus Lactis, Lactococcus Cremoris, Lactococcus Diacetylactis, Leuconostoc Cremoris and a combination hereof.

In yet a further embodiment of the present invention, the main lactic acid bacterial strain provided in step (ii) and/or the one or more lactic acid bacterial strain present in the fermented composition and/or the one or more lactic acid bacterial strain present in the isolated cannabinoid composition may be Pediococcus pentosaceus; Pendiococcus acidilactici; Lactobacillus plantarum; Lactobacillus rhamnosus; or Enterococcus faecium. Preferably, the main lactic acid bacteria present in the composition may be Lactobacillus plantarum.

In another embodiment of the present invention the one or more lactic acid bacteria strain(s) provided in step (ii) and/or the one or more lactic acid bacterial strain present in the fermented composition and/or the one or more lactic acid bacterial strain present in the isolated cannabinoid composition may be selected from the group consisting of one or more of Enterococcus faecium MCIMB 30122, Lactobacillus rhamnosus NCIMB 30121, Pediococcus pentosaceus HTS (LMG P-22549), Pendiococcus acidilactici NCIMB 30086 and/or Lactobacillus plantarum LSI (NCIMB 30083). In order to increase productivity and effectivity two or more lactic acid bacterial strains may be provided, such as three or more lactic acid bacterial strains, e.g. four or more lactic acid bacterial strains, such as 7 or more lactic acid bacterial strains, e.g. 10 or more lactic acid bacterial strains, such as 15 or more lactic acid bacterial strains, e.g. 20 or more lactic acid bacterial strains, such as 25 or more lactic acid bacterial strains, e.g. 30 or more lactic acid bacterial strains, such as 35 or more lactic acid bacterial strains, e.g. 40 or more lactic acid bacterial strains.

In order to provide the desired effects, the fermenting medium should have a high content of viable lactic acid bacteria. In an embodiment of the present invention the fermented composition comprises one or more lactic acid bacterial strain(s) in a total amount in the range of 10⁴-10¹² CFU per gram, such as in the range of 10⁵-10¹¹ CFU per gram, e.g. in the range of 1O⁶-1O¹⁰ CFU per gram, such as in the range of 10⁶-10⁸ CFU per gram, e.g. in the range of 10⁶-10⁷ CFU per gram.

In yet an embodiment of the present invention a starter culture or an inoculum may be provided comprising one or more lactic acid bacterial strains defined herein.

The term "inoculum" relates to a source material, such as the one or more lactic acid bacterial strain, used for the inoculation of a new culture. The inoculum may be employed to prime a process of interest.

"Inoculation" refers to the placement of a microorganism (e.g. one or more lactic acid bacterial strain) that will grow when implanted in a culture medium such as a fermentation tank comprising media to be fermented, e.g. the plant material selected from the cannabaceae family.

A primary inoculum may be provided and refers to the generation of an initial inoculum in a series of repeated similar of essentially identical inoculation process, for example one or more repetitions of a fermentation process. An aliquot of the fermenting medium may be used to inoculate a new process of fermentation of plant material. Thus, the inoculum may be a portion of the fermenting medium which comprises viable lactic acid producing bacteria in sufficient amount to prime a lactic acid fermentation process of another plant material, to be fermented.

The inoculum according to the present invention may be a in a liquid form, dry form, or essentially dry form. The moisture content of the inoculum may be adjusted in order to optimize the fermentation process. In one embodiment of the present invention, the inoculum may be provided as essentially pure viable bacteria (such as bacteria in freeze dried form) or bacteria suspended in a suitable aqueous medium prior to the being added to the plant material provided in step (i).

The proportion of the inoculums added to the plant material may vary. In case it is considered that the load of undesirable microbes is significant in the plant material or the fermentation system, the proportion of the inoculum in the fermentation mixture (inoculum + plant material + additional water) may be increased to ensure that the fermentation is directed by the microbes (e.g. lactic acid bacteria) of the inoculums and not by the microorganisms present on the plant material.

In an embodiment of the present invention, the inoculum may be provided with a concentration of lactic acid bacteria in the inoculum sufficient to outgrow other non-lactic acid bacteria, yeast or moulds, present in or on the plant material.

Accordingly, in one embodiment of the invention, the proportion of the inoculums in the combination of the plant material and the one or more lactic acid material as defined in step (iii) is in the range of 0.1 to 99.9 vol-%; such as 1 to 99 vol-%; e.g. 5 to 70 vol-%; such as 10 to 50 vol-%; e.g. 25 to 35 vol-%; such as 0.1 to 10 vol-%; e.g. 0.5 to 5 vol- %; such as 1 to 2.5 vol-%; or around 1 to 2 vol-%.

In an embodiment of the present invention the fermentation process (step (iii)) may be an anaerobic fermentation process or a semi-anaerobic fermentation process. Preferably, the fermentation process is a semi-anaerobic fermentation process.

Even CBD may cyclize to THC under acidic conditions the inventors of the present invention surprisingly found that lactic acid (produced during the fermentation process of the present invention did not affect, or did not significantly affect, the stability of the cannabinoid composition, preferably the cannabidiol-acid. Without being bound by theory it is believed that the preservation of the cannabinoid composition, preferably the cannabidiol-acid, may be provided because of the fibrous material of the plant which may protect the cannabinoid composition, preferably the cannabidiol-acid, and possibly also protecting the terpenes in the composition.

A semi-anaerobic fermentation process relates to a fermentation process without the addition of oxygen and/or air to the fermenting medium. However, the oxygen and/or air present in and surrounding the fermenting medium are maintained and may be available and used by the one or more lactic acid bacteria strains. Ensilation may be an example of a semi-anaerobic fermentation process. Ensilation relates to the process of making silage from field crops where by placing the plant material in a silo or pit, by piling it in a large heap and compressing it down so as to leave as little oxygen as possible and then covering it with a plastic sheet, or by wrapping large round or square bales tightly in plastic film, or pressing it into a plastic sausage-like packaging whereby the plant material is left for semi-anaerobic fermentation. In accordance with the present invention the plant material is mixed with one or more lactic acid bacteria when ensiled.

The cannabinoid composition of the present invention, in particular the acidic cannabinoid (like CBD-A) may be sensible to the presence of oxygen. Therefore, the oxygen may be removed or substantially removed from the plant material from the cannabaceae family and/or the fermented composition to improve fermentation and the composition.

The content of oxygen during fermentation may preferably be reduced or removed to limit or avoid formation of acetic acid and/or ethanol during fermentation of the plant material.

The process of removing or depleting oxygen from the plant material may be performed during at least the first day from adding the lactic acid bacteria to the plant material; such as within at least the first 10 hours from adding the lactic acid bacteria to the plant material; e.g. within the at least first 5 hours; such as within at least the first 2 hours; e.g. within the at least first 1 hours.

In an embodiment of the present invention oxygen may be removed or substantially removed from the plant material before the fermentation is started.

In a further embodiment of the present invention the process of removing or depleting oxygen from the plant material may be performed within the first day from harvest of the plant material; such as within at least the first 10 hours from harvest; e.g. within the at least first 5 hours; such as within at least the first 2 hours; e.g. within the at least first 1 hours.

The amount of oxygen present in, and/or surrounding, the inoculated material, or the fermented material, may be reduced in, or depleted from, oxygen by introducing gas depletion and/or vacuum. In the context of the present invention the term "gas depletion" relates to a process where a gas other than oxygen is introduced into the inoculated material and depletes (fully or partly) oxygen from the inoculated material. Alternatively, or additionally, the inoculated material may be reduced in, or depleted from, oxygen content by subjecting the inoculated material to a vacuum treatment.

In an embodiment of the present invention the gas suitable for depleting the plant material from oxygen may be selected from nitrogen or argon. Preferably the gas is argon.

In an embodiment of the present invention the fermentation process as described in step (iii) of the present invention, comprising the plant material provided in step (i) with the one or more lactic acid bacterial strains provided in step (ii) may be ensiled in bags, e.g. plastic bags, 25 kg -250 tons, such as 3-200 tons, e.g. 5-150 tons, such as 10-100 tons, e.g. 50-75 tons.

In an embodiment of the present invention, the fermentation process provided in step (iii) may be a one-step fermentation of the plant material.

In the present context, the term "one-step fermentation" relates to a fermentation process wherein the same type of plant material may be subjected to the same fermentation conditions, or substantially the same fermentation conditions. Hence, the term "one-step fermentation", exclude the option of taking out a part of the plant material during fermentation, leaving the remaining plant material to be further fermented and followed by mixing the part which was taken out with the further fermented composition.

In a further embodiment of the present invention, the fermenting medium does not involve subsequent supplementation of plant material and/or subsequent supplementation of one or more lactic acid bacterial strain(s) to the fermenting medium.

The fermentation process according to the present invention, may preferably be essentially homofermentative. "Essentially homofermentative" means, that the predominant bacterial flora driving the fermentation are essentially homofermentative. In the present context, the term "essentially homofermentative" relates to a fermentation process where, 70% or more of the bacteria are homofermentative, such as 80% or more of the bacteria are homofermentative, e.g. 85% or more of the bacteria are homofermentative, such as 90% or more of the bacteria are homofermentative, e.g. 95% or more of the bacteria are homofermentative, such as 98% or more of the bacteria are homofermentative, e.g. 99% or more of the bacteria are homofermentative.

In an embodiment of the present invention the fermentation is essentially a homofermentation, such as a homolactic fermentation. The term "homolactic fermentation" when used according to the present invention indicates that the major fermentation product may be lactic acid, and the levels of e.g. acetic acid and ethanol are either below taste-threshold, around taste threshold or slightly above taste threshold, preferably below taste-threshold. The term "essentially homofermentative" may indicates a ratio of lactic acid to acetic acid or lactic acid to ethanol in (mM/mM) of more than 1 : 1, such as 2: 1 or more, e.g. 10: 1 or more, such as 20: 1 or more, e.g. 50: 1 or more, or such as 100: 1 or more.

In an embodiment of the present invention, the fermented composition provided in step (iii) and/or the isolated cannabinoid composition provided in step (iv) may have a lactic acid concentration of at least 10 mM, such as at least 50 mM, such as 50-1000 mM, such as 100-500 mM, such as 100-300 mM, such as 100-200 mM, such as 150-500 mM, such as 200-500 mM or such as 300-500, mM lactic acid.

In another embodiment of the present invention the process according to the present invention is essentially a heterofermentative fermentation.

In the present context, the term "essentially heterofermentative" means, that the predominant bacterial flora driving the fermentation is heterofermentative. In the present context the term "essentially heterofermentative" relates to a fermentation process where, 70% or more of the bacteria are heterofermentative, such as 80% or more of the bacteria are heterofermentative, e.g. 85% or more of the bacteria are heterofermentative, such as 90% or more of the bacteria are heterofermentative, e.g. 95% or more of the bacteria are heterofermentative, such as 98% or more of the bacteria are heterofermentative, e.g. 99% or more of the bacteria are heterofermentative.

In an embodiment of the present invention the hetero-fermentation according to the present invention results in a major part of the fermentation products are acetic acid and/or ethanol, and the ratio of acetic acid and/or ethanol to lactic acid in (mM/mM) is more than 1 : 1, such as 2: 1 or more, e.g. 10: 1 or more, such as 20: 1 or more, e.g. 50: 1 or more, or such as 100: 1 or more.

In a further embodiment of the present invention, the fermented composition provided in step (iii) and/or the isolated cannabinoid composition provided in step (iv) may have an acetic acid and/or ethanol concentration of at least 50 mM, such as at least 100 mM, such as 100-1000 mM, such as 100-500 mM, such as 100-300 mM, such as 100-200 mM, such as 150-500 mM, such as 200-500 mM or such as 300-500, mM. Preferably, the fermentation process according to the present invention is essentially a homofermentative fermentation process.

The inventors of the present invention surprisingly found that fermentation was important because it breaks down part of the structural carbohydrates in the plant material, where enzymes formed during the fermentation breaks down the proteinfibre matrix as well as the phytic acid in the flowers and opens up the structure of the plant material of the present invention. This all leads to a higher concentration of cannabinoid compounds, in particular cannabinoid acids, compared to traditional used methods.

Using the fermentation step, the drying step may be avoided, and conversion of cannabinoid acids can be largely avoided, and a high content of cannabinoid acids may be obtained which easier dissolves in water and will easier be absorbed in the body and provide with much higher efficiency.

The inventors of the present invention surprisingly found that the fermentation process may cause the pH to drop to acidic conditions without observing a change or cyclization from CBD (or CBD-A) to THC (or THC-A). Without being bound by theory, the inventors of the present invention trust that the CBD (or CBD-A) structure may be maintained because of the complex fibrous network and fermentation products formed during the fermentation process, protects the CBD (or CBD-A) structure from converting/cyclization.

In an embodiment of the present invention the fermentation process (step (iii)) may be continued until the fermenting medium has a pH value below 7.0. In a further embodiment of the present invention the fermentation process may be continued until the fermenting medium has a pH value below 6.5, e.g. a pH value below 6.0, such as a pH value below 5.0 e.g. a pH value below 4.5 such as a pH value below 4.0.

Preferably, the pH-value of the fermenting medium and/or the composition may be in the range of pH 3.0-7.0; e.g. in the range of pH 3.0-6.5; such as in the range of pH 3.0-6.0; e.g. in the range of pH 3.1-5.5; such as in the range of pH 3.2-5.0; such as in the range 3.3-4.2; such as 3.4-4.0; such as 3.5-3.8; such as 3.7-4.2; such as 3.7-4.0; or such as 3.8-4.2. PH of the fermenting medium may be important in order to improve permeability over the cell wall as acids, such as organic acid produced during the fermentation, disrupt or destroy the cell wall, and increasing the permeability and liberate the one or more cannabinoid compounds from the plant material. The lactic acid bacteria added in step (ii) may during fermentation produce organic acids, such as lactic acid, and other metabolic products, which may not only contribute to a more intense degeneration of the cell walls of the fermenting medium, but may also contribute to the organoleptic, textural, nutritional and pharmacological profile of the fermenting medium and the composition of the present invention.

In an embodiment of the present invention the process involves no addition of acid compound to the fermenting medium.

In the context of the present invention the term "addition of acid compound" relates to the action of adding an isolated or partly isolated acid compound to the fermenting medium. The reduction provided in the fermenting medium may preferably be provided by the acids formed by the microorganisms present in the fermenting medium. In a preferred embodiment of the present invention the acid compound present in the composition originates from the lactic acid bacterial strain. Preferably the acid compound present in the composition originating from the lactic acid bacterial strain is lactic acid.

In an embodiment of the present invention the fermentation process provided in step (iii) may introduce a decrease in pH from about pH 7.0 to about pH 5.0 in 1-8 days, such as in 3-5 days.

It may be advantageous to have a fast decrease in pH because the low pH may prevent growth of undesirable and unwanted microorganisms in the plant material and in the fermenting medium.

In an embodiment of the present invention the fermentation process provided in step (iii) introduce a decrease in pH from about pH 7.0 to about pH 5.0 in 1-10 days; such as in 2-8 days; e.g. in 3-7 days; such as in 4-6 days, e.g. in 2-4 days.

In yet an embodiment of the present invention the fermentation process provided in step (iii) introduce a decrease in pH from about pH 7.0 to about pH 4.5 in 1-10 days; such as in 2-8 days; e.g. in 3-7 days; such as in 4-6 days; e.g. in 2-4 days. In another embodiment of the present invention the fermentation process provided in step (iii) introduce a decrease in pH from about pH 7.0 to about pH 4.0 in 1-10 days; such as in 2-8 days; e.g. in 3-7 days; such as in 4-6 days; e.g. in 2-4 days.

The inventors of the present invention, found that other components from the fermentation process, e.g. enzymes produced during the fermentation, other than the acid produced, also may participate in the degeneration of the cell wall and in the liberation of the one or more cannabinoid compounds from the plant material, such as CBD-A.

Hence, with the fermentation process according to the present invention it may be possible to obtain a much more intense degeneration of the cell walls of the plants, and then increasing the efficacy of the extraction afterwards. The improved degradation and increased permeability of the cell walls make it possible to separate more of the one or more cannabinoid compounds, such as CBD-A, present in the plant material and the process may be faster, with less "pollution" from proteins, enzymes, chlorophylls and/or minerals in the composition.

In order to increase permeability and degradation of the plant material and allowing liberation of one or more cannabinoid compounds from the plant material the fermentation process of the fermenting medium (step (iiii)) may be continued for a period of time after a decreased pH level of the fermenting medium has been obtained.

In an embodiment of the present invention the fermentation process as provided in step (iii) may be continued for at least 5 hours after the pH of the fermenting medium has reached a pH in the range of pH 3.0-5.5; such as for at least 10 hours; e.g. for at least at least 15 hours; such as at least 24 hours; e.g. for at least at least 2 days; such as at least 3 days; e.g. for at least 5 days; such as at least 10 days; e.g. for at least 20 days; such as at least 30 days; e.g. for at least 50 days; such as at least 100 days; e.g. for at least 200 days.

In yet an embodiment of the present invention the fermentation process as provided in step (iii) may be continued for at least 5 hours after the pH of the fermenting medium has reached a pH in the range of pH 3.0-5.0; such as for at least 10 hours; e.g. for at least at least 15 hours; such as at least 24 hours; e.g. for at least at least 2 days; such as at least 3 days; e.g. for at least 5 days; such as at least 10 days; e.g. for at least 20 days; such as at least 30 days; e.g. for at least 50 days; such as at least 100 days; e.g. for at least 200 days. In another embodiment of the present invention the fermentation process as provided in step (iii) may be continued for at least 5 hours after the pH of the fermenting medium has reached a pH in the range of pH 3.0-4.5; such as for at least 10 hours; e.g. for at least at least 15 hours; such as at least 24 hours; e.g. for at least at least 2 days; such as at least 3 days; e.g. for at least 5 days; such as at least 10 days; e.g. for at least 20 days; such as at least 30 days; e.g. for at least 50 days; such as at least 100 days; e.g. for at least 200 days.

The fermentation process as provided in step (iii) may preferably involve a temperature gradient of the fermenting medium, said temperature gradient may involve 3 stages; a starting temperature, a temperature increase and a steady state fermentation temperature.

The inventors of the present invention found that a certain time of fermentation during steady state fermentation may be required to provide the desired effects of the fermented composition.

In an embodiment of the present invention the fermenting medium may be allowed to ferment for at least 2 hours, e.g. for at least at least 5 hours; such as at least 10 hours; e.g. for at least at least 15 hours; such as at least 24 hours; e.g. for at least at least 2 days; such as at least 3 days; e.g. for at least 5 days; such as at least 10 days; e.g. for at least 20 days; such as at least 30 days; e.g. for at least 50 days; such as at least 100 days; e.g. for at least 200 days; such as at least 300 days.

The fermentation process according to step (iii) of the claimed invention may involve a steady state fermentation.

In the context of the present invention the term "steady state fermentation" relates to a period of the fermentation process where the fermenting medium is allowed to ferment for a period of time with substantially no change in pH (at substantially constant pH) and/or substantially constant temperature. The steady state fermentation allows acids and enzymes to degrade the cell wall of the plant material, resulting in e.g. liberation of one or more cannabinoid compounds from the plant material.

In an embodiment of the present invention the fermenting medium may be allowed to ferment under a steady state fermentation for a period of at least 2 hours, e.g. for at least at least 5 hours; such as at least 10 hours; e.g. for at least at least 15 hours; such as at least 24 hours; e.g. for at least at least 2 days; such as at least 3 days; e.g. for at least 5 days; such as at least 10 days; e.g. for at least 20 days; such as at least 30 days; e.g. for at least 50 days; such as at least 100 days; e.g. for at least 200 days; such as at least 300 days.

Furthermore, the fermentation according to step (iii) of the present invention may be continued during steady state for 10 days or less, such as 9 days or less, e.g. 8 days or less, such as 7 days or less, e.g. 6 days or less, such as 5 days or less, e.g. 4 days or less, such as 3 days or less, e.g. 2 days or less, such as 36 hours or less, e.g. 24 hours or less.

In an embodiment of the present invention the fermentation process according the step (iii) of the present invention may be continued for a period (a steady state period) between 6 hours and 300 days; such as for a period of 12 hours to 100 days; e.g. for a period of 48 hours to 20 days; such as for a period of 3 days to 10 days.

Controlling the temperature during the steady state fermentation may be an important way to improve the quality and/or the effects of the fermenting medium.

In an embodiment of the present invention, the fermentation may be performed at a temperature during the steady state fermentation below 50°C, such as below 47°C, e.g. below 45°C, such as below 43°C, e.g. below 40°C, such as about 35°C. Preferably, the fermentation process in step (iii) may be conducted at a temperature (a steady state temperature) in the range of 15-50°C, preferably in the range of 25-43°C, more preferably in the range of 30-40°C, even more preferably, about 35°C.

In an embodiment of the present invention the starting temperature may be in the range of 10-35°C, such as in the range of 15-30°C, e.g. in the range of 18-25°C.

In yet an embodiment of the present invention the temperature of the fermenting medium during storage is allowed to fluctuate together with fluctuations of the surrounding temperature, in particular when the fermentation is performed as an ensilation of the plant material provided in step (i).

The temperature increase of the fermenting medium of the present invention may preferably be a slow temperature increase from the starting temperature to the steady state fermentation temperature. In an embodiment of the present invention the temperature increase is provided without addition of heat. In the present context, the term "without addition of heat" relates to a fermentation temperature increase wherein the heat provided is produced by the fermentation itself without the use of electrical, mechanical or fuel-based heat. In an embodiment of the present invention the fermentation process (as provided in step (iii)) may be a controlled fermentation process.

In a further embodiment of the present invention the fermentation process is a solid-state fermentation.

In the context of the present invention the term "solid state fermentation" relates to a process where fermenting microorganisms are added to a plant material and allowed to ferment at a low moisture content under controlled conditions for several days. A low moisture content may be conditions where the plant material during fermentation is not pumpable.

In an embodiment of the present invention the plant material provided in step (i) may have a moisture content above 10% (w/w), e.g. above 12% (w/w), such as above 15% (w/w), e.g. above 20% (w/w), such as above 30% (w/w), e.g. above 40% (w/w).

In yet an embodiment of the present invention the plant material provided in step (iii) may have a moisture content below 95% (w/w), such as below 90% (w/w), e.g. below 85% (w/w), such as below 82% (w/w), e.g. below 80% (w/w), such as below 75% (w/w), e.g. below 70% (w/w), such as below 65% (w/w), e.g. below 60% (w/w).

The plant material provided in step (iii) may have a moisture content in the range of 10- 90% (w/w); such as in the range of 20-80% (w/w); e.g. in the range of 30-70% (w/w); such as in the range of 40-60% (w/w), e.g. in the range of 45-55% (w/w).

In an embodiment of the present invention the plant material and the fermented composition may have a moisture content from step (i) until an isolated cannabinoid composition has been obtained in step (iv) in the range of 10-90% (w/w).

The plant material provided in step (i) may be a fresh plant material. Preferably, the plant material provided in step (i) has not been subjected to drying.

In order to facilitate the fermentation process and/or extraction or separation of one or more cannabinoid compounds, an aqueous medium may be added to the plant material selected from the cannabaceae family.

In an embodiment of the present invention an aqueous medium may be added to the plant material provided in step (i), to the one or more lactic acid bacteria stain before the one or more lactic acid bacteria stain is added to the plant material (step (ii)); or to the combination of the plant material and the one or more lactic acid bacteria strain.

The aqueous medium may be added to the plant material in a ratio (based on w/w) less than 1 : 50 (aqueous medium : plant material); such as a ratio less than 1 :20; e.g. a ratio less 1 : 10; such as a ratio less than 1 : 5; e.g. a ratio less 1 : 1.

In an embodiment of the present invention the aqueous medium comprises water, preferably demineralized water.

The temperature of the aqueous medium may be in the range of 15-60°C, preferably in the range of 25-50°C, more preferably in the range of 30-40°C, even more preferably, about 38°C.

In order to promote growth of the lactic acid bacteria the plant material the fermenting medium may be further supplemented with one or more further ingredient. In an embodiment of the present invention a carbon source may be added to the plant material provided in step (i), or to the fermenting medium.

Preferably, the carbon source may be a carbohydrate, a carbohydrate containing material or a combination hereof.

Preferably, the carbohydrate may be sugar, syrup, dextrose, molasses or other sugar containing sources.

Preferably, the carbohydrate containing material may be selected from cereals, (e.g. wheat, barley, rye, rice, maize (cob maize silage (CCM) or ripe), triticale, oat); vegetables (e.g. potatoes, beans, peas, maize, soy); carbohydrate ingredient (such as whey, curd, skim milk and the like); or any combination hereof.

The inventors of the present invention found it was advantageous that the process of separating one or more cannabinoid compounds, such as CBD-A, from the plant material, in particular from the fibrous plant materials, may involve a fermentation process. The fermentation process allows the acids and enzymes produced during the fermentation to act on the cell wall of the plant material and increasing the permeability of cannabinoid acid compounds, like CBD-A, from the plant cells which are then separated, and without compromising the cannabinoid acid compounds. Traditionally, harvesting plant materials comprising one or more cannabinoid compounds, like CBD-A, needs to be done in just a couple of weeks when the level is at its peak. Often the drying capacity is limiting the harvest. Plants need to be in the dryer within half a day after harvest, otherwise the quality deteriorates fast. With the present invention, avoiding the drying step and replacing it with a fermentation step, there are less or no limits to the speed of harvesting, larger quantities may be process at each batch, and much more can be done at the optimal harvesting moment.

By introducing the fermentation process according to the present invention of fresh plant materials, like fresh hemp plants, the moment of harvesting may be disconnected from the moment of further processing of the fermented composition.

In the context of the present invention, the term "disconnected" relates to extending the time from harvesting to further processing, in order to make the process more cost effective and allow the individual farmer/producer to process larger amounts of plant materials in a single season. Hence, the process according to the present invention the time may be extended from a couple of days to e.g. 12 months where the cannabinoid acid compounds, such as CBD-A, containing products can be separated from the fermented composition.

In an embodiment of the present invention the fermented composition provided in step (iii) is stored for period between 10 hours and 12 months before being subjected to at least one processing step , providing the isolated cannabinoid composition, such as isolated CBD-A, containing commercial product or raw material; e.g. for a period of 24 hours and 10 months; such as for a period of 36 hours to 9 months; e.g. for a period of 48 hours and 8 months; such as for a period of 60 hours to 7 months; e.g. for a period of 72 hours and 6 months; such as for a period of 96 hours to 5 months; e.g. for a period of 120 hours and 3 months.

Step (iv) of the present invention relates to subjecting the fermented composition to one or more separation processes providing an isolated cannabinoid composition.

In an embodiment of the present invention the separation process comprises at least one clarification process separating the solubilised one or more cannabinoid compounds from the insoluble plant material, providing the isolated cannabinoid composition.

At least one clarification process, providing the isolated cannabinoid composition may include pressing; decanting; centrifugation; precipitation; filtration and/or chromatography, such as ion exchange chromatography, affinity chromatography, hydrophobic interaction chromatography, reversed phase chromatography, or anyone combination hereof.

Cold pressing may be the preferred clarification process, since this enables the resulting product to be sold as an over the counter (non-prescription) health food, and a much higher amount of sellable product can be extracted. Cold pressing may be done by using only water as a solvent (preferably using the aqueous medium), and the processing of plant material can be performed spread over a long period of time. The harvesting moment can be de-coupled in time from the further upstream processing of the harvested plant material.

Pressing may be performed using a screw press, a stack press or a belt press.

In an embodiment of the present invention the fermented composition provided in step (iii) may be stored before being subjected to at least one separation process, providing the isolated cannabinoid composition.

The fermented composition provided in step (iii) may be stored for period between 10 hours and 12 months before being subjected to at least one separation process, providing the isolated cannabinoid composition; e.g. for a period of 24 hours to 10 months; such as for a period of 36 hours to 9 months; e.g. for a period of 48 hours and 8 months; such as for a period of 60 hours to 7 months; e.g. for a period of 72 hours and 6 months; such as for a period of 96 hours to 5 months; e.g. for a period of 120 hours and 3 months.

In an embodiment of the present invention the fermented composition provided in step (iii) may be stored for at least 10 hours before being subjected to at least one separation process, providing the isolated cannabinoid composition; e.g. for at least 24 hours; such as at least 36 hours; e.g. for at least 48 hours; such as at least 60 hours; e.g. for at least 72 hours; such as at least 96 hours; e.g. for at least 120 hours; such as at least 14 days; e.g. for at least 1 months; such as at least l¹/2 months; e.g. for at least 2 months; such as at least 2¹/2 months; e.g. for at least 3 months; such as at least 4 months; e.g. for at least 5 months; such as at least 6 months; e.g. for at least 8 months; such as for at least 10 months.

Preferably, the aqueous medium may be used as extractant of the one or more cannabinoid compound providing the isolated cannabinoid composition. In an embodiment of the present invention the extractant does not involve an organic extractant.

Increased temperature may improve and/or facilitate the solubilization or extraction of the cannabinoid compound, such as CBD-A, providing the isolated cannabinoid composition. Hence, the temperature of the fermented composition may during extraction and/or separation be in the range of 15-95°C, preferably in the range of 20-70°C, more preferably in the range of 40-65°C, even more preferably, about 60°C.

In an embodiment of the present invention the extraction may be performed in multiple step counter-flow diffusion with acid water recovered from previous batches of fermented compositions according to the present invention.

In the present context, the process of extraction relates the action of solubilizing the cannabinoid compound, such as CBD-A, present in the plant material and releasing the the cannabinoid compound, such as CBD-A, from the plant material to the aqueous medium.

In an embodiment of the present invention the temperature of the plant material during the entire process from harvest to composition may preferably be kept at a temperature below 110°C, e.g. below 100°C; such as below 90°C; e.g. below 80°C; such as below 70°C; e.g. below 65°C.

An aspect of the present invention relates to a fermented composition obtainable by the process according to the present invention.

A further aspect of the present invention relates to a fermented composition comprising one or more cannabinoid compound and one or more lactic acid bacterial strain or a derivative of one or more lactic acid bacterial strain.

In the context of the present invention the term "derivative" relates to a metabolite obtained from the at least one lactic acid bacterial strain; or a fragment of the at least one lactic acid bacterial strain.

In an embodiment of the present invention the fermented composition further comprises at least 1% fibrous material, based on the total weight of the fermented composition, such as at least 3%; e.g. at least 5%; such as at least 10%; e.g. at least 15%; such as at least 20%; e.g. at least 30%; such as at least 40%. Preferably the fibrous material of the fermented composition may be originating from the plant material provided in step (i).

In an embodiment of the present invention the fibrous material may have an average particle size of 50 mm or less, such as an average particle size of 30 mm or less, such as an average particle size of 20 mm or less, such as an average particle size of 10 mm or less such as an average particle size in the range 1-40 mm; such as in the range of 10-30 mm, e.g. in the range of 20-25 mm.

In an embodiment of the present invention the fermented composition may be a dried powder; a syrup; a liquid product; or an emulsion.

A further aspect of the present invention relates to an isolated cannabinoid composition obtainable by a process according to the present invention.

An even further aspect of the present invention relates to an isolated cannabinoid composition comprising one or more cannabinoid compound; one or more lactic acid bacterial strain or a derivative of one or more lactic acid bacterial strain; and less than 10% (w/w) fibrous material.

Preferably, the isolated cannabinoid composition comprising less than 1% (w/w) fibrous material; such as less than 0.75% (w/w); e.g. less than 0.5% (w/w); such as less than 0.25% (w/w); e.g. less than 0.1% (w/w); such as a non-detectable amount of fibrous material.

In an embodiment of the present invention the isolated cannabinoid composition may be a dried powder; a syrup; a liquid product; or an emulsion.

In an embodiment of the present invention the fermented composition and/or the isolated cannabinoid composition comprises viable lactic acid bacteria.

In an embodiment of the present invention the composition comprises one or more lactic acid bacterial strain(s) in a total amount in the range of 10⁴-10¹² CFU per gram, such as in the range of 10⁵-10¹¹ CFU per gram, e.g. in the range of 1O⁶-1O¹⁰ CFU per gram, such as in the range of 10⁶-10⁸ CFU per gram, e.g. in the range of 10⁶-10⁷ CFU per gram.

The process according to the present invention may further comprise a step of reducing the moisture content of the composition (the fermented composition and/or the isolated cannabinoid composition) obtained from the fermentation process according to step (iii) or step (iv). In an embodiment of the present invention the composition may be subjected to drying.

Any moisture reducing methods may be used which are sensitive to the pre- and probiotic components, such as the lactic acid bacteria and/or the CBD(A)s, in order to maintain the activity of the components in the fermenting medium and which moisture reducing methods ensure high viability of the lactic acid bacteria present in the fermented composition. The method to reduce to moisture content as described in WO 2013/029632 may be preferred (WO 2013/029632 is hereby incorporated by reference).

An aspect of the present invention relates to the use of the fermented composition according to the present invention and/or the isolated cannabinoid composition according to the present invention as an ingredient in a beverage or a food product or a feed product.

A further aspect of the present invention relates to a beverage comprising the fermented composition according to the present invention and/or the isolated cannabinoid composition according to the present invention.

An even further aspect relates to a food product comprising the fermented composition according to the present invention and/or the isolated cannabinoid composition according to the present invention.

In the present context of the present invention, the term "substantially no" relates to the presence of less than 5% (w/w); such as the presence of less than 3% (w/w); e.g. less than 1% (w/w); such as undetectable amounts.

A preferred embodiment of the present invention relates to a fermented composition or an isolated composition according to the present invention for use as a medicament.

In an embodiment of the present invention the fermented composition or the isolated cannabinoid composition may be used for the preparation of a phytoceutical, a nutraceutical or a health product.

A preferred embodiment of the present invention relates to a fermented composition or an isolated cannabinoid composition according to the present invention for use in the treatment of nausea, anxiety, Chronic pain, Multiple sclerosis, vomiting, no or suppressed appetite, Gilles de la Tourette syndrome, Glaucoma Cancer, Epilepsy, Inflammatory bowel diseases, Parkinson's disease, Psychiatric disorders (taken from Bedrocan), Mood disorders, depression, co-morbid anxiety, other psychiatric disorders and bipolar disorders. It should be noted that embodiments and features described in the context of one of the aspects of the present invention also apply to the other aspects of the invention.

All patent and non-patent references cited in the present application, are hereby incorporated by reference in their entirety.

References

WO 2013/029632

Claims

1. A process for providing a composition comprising one or more cannabinoid compounds from a plant material selected from the cannabaceae family, the method comprises the steps of:

(i) providing a plant material from the cannabaceae family;

(iii) allowing the fermenting medium to ferment for at least 1 hour providing a fermented composition; and

(iv) optionally, subjecting the fermented composition to one or more separation processes providing an isolated cannabinoid composition; wherein the plant material is selected from the flowers of the plant material; the (top) leaves of the plant material; the stem of the plant material; or the combination of the flowers, leaves and the stem of the plant material.

2. The process according to claim 1, wherein the fermentation process is continued until the fermenting medium has a pH value below 6.5, e.g. a pH value below 6.0, such as a pH value below 5.0 e.g. a pH value below 4.5 such as a pH value below 4.0.

3. The process according to anyone of the preceding claims wherein the fermentation process provided in step (iii) introduce a decrease in pH from about pH 7.0 to about pH 5.0 in 1-10 days; such as in 2-8 days; e.g. in 3-7 days; such as in 4-6 days.

4. The process according to anyone of the preceding claims wherein the composition comprises at least 10 mM lactic acid, such as at least 50 mM lactic acid, such as 50-1000 mM lactic acid, such as 100-500 mM lactic acid, such as 100-300 mM lactic acid, such as 100-200 mM lactic acid, such as 150-500 mM lactic acid, such as 200-500 mM lactic acid; or such as 300-500 mM lactic acid.

5. The process according to anyone of the preceding claims, wherein the fermentation process in step (iii) is conducted at a temperature (in particular a steady state temperature) is in the range of 15-50°C, preferably in the range of 25-43°C, more preferably in the range of 30-40°C, even more preferably, about 35°C.

6. The process according to anyone of the preceding claims, wherein an aqueous medium is added to the plant material provided in step (i), to the one or more lactic acid bacteria strains before the one or more lactic acid bacteria strain is added to the plant material (step (ii)); or to the combination of the plant material and the one or more lactic acid bacteria strain.

7. The process according to anyone of the preceding claims, wherein the separation process comprises at least one clarification process providing the isolated cannabinoid composition, preferably the at least one clarification process includes pressing, such as cold pressing.

8. The process according to anyone of the preceding claims, wherein oxygen is removed or substantially removed from the plant material before the fermentation is started.

9. The process according to anyone of the preceding claims, wherein the plant material and the fermented composition may have a moisture content from step (i) until an isolated cannabinoid composition has been obtained in step (iv) in the range of 10-90% (w/w).

10. A fermented composition comprising one or more cannabinoid compound and one or more lactic acid bacterial strain, or a derivative of one or more lactic acid bacterial strain.

11. An isolated cannabinoid composition comprising one or more cannabinoid compound; one or more lactic acid bacterial strain or a derivative of one or more lactic acid bacterial strain; and less than 10% (w/w) fibrous material.

12. The composition according to anyone of claims 10 or 11, wherein the composition in addition to the presence of the one or more cannabinoid compound comprises one or more terpene.

13. The composition according to claim 12, wherein the one or more terpenes may be preserved, or may be substantially preserved, relative to the terpene profile of the plant material before fermentation.

14. Use of the fermented composition according to claim 10 and/or the isolated cannabinoid composition according to claim 11, as an ingredient in a beverage or a food product.

15. A fermented composition according to claim 10 and/or the isolated cannabinoid composition according to claim 11 for use as a medicament.

16. A fermented composition according to claim 10 and/or the isolated cannabinoid composition according to claim 11, for use in the treatment of nausea, anxiety, Chronic pain, Multiple sclerosis, vomiting, no or suppressed appetite, Gilles de la Tourette syndrome, Glaucoma Cancer, Epilepsy, Inflammatory bowel diseases, Parkinson's disease, Psychiatric disorders (taken from Bedrocan), Mood disorders, depression, co-morbid anxiety, other psychiatric disorders and bipolar disorders.

17. Use of the fermented composition according to claim 10, or the isolated cannabinoid composition according to anyone of claims 11-13, for the preparation of a phytoceutical, a nutraceutical or a health product.