WO2001007135A1 - Extraction of materials from plants - Google Patents
Extraction of materials from plantsInfo
- Publication number
- WO2001007135A1 WO2001007135A1 PCT/GB2000/002870 GB0002870W WO0107135A1 WO 2001007135 A1 WO2001007135 A1 WO 2001007135A1 GB 0002870 W GB0002870 W GB 0002870W WO 0107135 A1 WO0107135 A1 WO 0107135A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- plant
- solvent
- plants
- extraction
- solvents
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 78
- 238000000605 extraction Methods 0.000 title claims description 22
- 241000196324 Embryophyta Species 0.000 claims abstract description 59
- 239000002904 solvent Substances 0.000 claims abstract description 34
- WUOACPNHFRMFPN-UHFFFAOYSA-N Terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229940116411 Terpineol Drugs 0.000 claims abstract description 24
- 230000000749 insecticidal Effects 0.000 claims abstract description 22
- 239000000077 insect repellent Substances 0.000 claims abstract description 15
- 230000000844 anti-bacterial Effects 0.000 claims abstract description 13
- 241000208818 Helianthus Species 0.000 claims abstract description 12
- 238000000638 solvent extraction Methods 0.000 claims abstract description 11
- 235000007516 Chrysanthemum Nutrition 0.000 claims abstract description 8
- 235000005986 Chrysanthemum x morifolium Nutrition 0.000 claims abstract description 8
- 150000003505 terpenes Chemical class 0.000 claims abstract description 7
- 235000007586 terpenes Nutrition 0.000 claims abstract description 7
- 239000010773 plant oil Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 38
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-(4R)-Limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 22
- 244000035851 Chrysanthemum leucanthemum Species 0.000 claims description 16
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 claims description 16
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 13
- 240000006669 Helianthus annuus Species 0.000 claims description 11
- 241000238631 Hexapoda Species 0.000 claims description 8
- 241000723353 Chrysanthemum Species 0.000 claims description 7
- 244000005700 microbiome Species 0.000 claims description 4
- 230000002879 macerating Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000001846 repelling Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 230000000975 bioactive Effects 0.000 abstract description 13
- 239000011149 active material Substances 0.000 abstract description 11
- 240000005250 Chrysanthemum indicum Species 0.000 abstract 1
- 241000255925 Diptera Species 0.000 description 17
- 240000004460 Tanacetum coccineum Species 0.000 description 14
- 229940015367 pyrethrum Drugs 0.000 description 14
- 239000000284 extract Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930007650 limonene Natural products 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000255930 Chironomidae Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000256103 Simuliidae Species 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000008601 oleoresin Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000020238 sunflower seed Nutrition 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000404133 Leucanthemum Species 0.000 description 1
- 229940099027 Leucanthemum vulgare extract Drugs 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 229940048383 Pyrethrum extract Drugs 0.000 description 1
- 241001530490 Salvia rosmarinus Species 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229940076185 Staphylococcus aureus Drugs 0.000 description 1
- 240000000785 Tagetes erecta Species 0.000 description 1
- 241000250966 Tanacetum cinerariifolium Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- -1 alcohols Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 230000001580 bacterial Effects 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 229930008380 camphors Natural products 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 125000000567 diterpene group Chemical group 0.000 description 1
- 229930004069 diterpenes Natural products 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002085 persistent Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 229930004725 sesquiterpenes Natural products 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Definitions
- This invention concerns the extraction of materials from plants, particularly bio-active materials, that is materials having insecticidal, bactericidal and/or insect repellent properties.
- Pyrethrum is a mixture of substances that acts as a powerful but non-persistent contact insecticide with rapid "knockdown" effect, while being non-toxic to mammals.
- Dried flowers are ground to fine powder. 5. Ground flowers are extracted using hexane solvent at elevated temperature.
- Oleoresin is refined by further selective solvent extraction performed at elevated temperature to provide a light coloured liquid.
- Refined extract is diluted using mineral oil to form a 25% (by weight) solution ready for sale and use.
- the process produces approximately 3% by weight pure pyrethrum extract from dry flowers.
- the present invention is based on a novel method of extracting materials from plants.
- the present invention further concerns extraction of bio-active material and associated material from the order compositi , in particular of plants in the Chrysanthemum family and of plants in the Helianthus family commonly known as Sunflowers, in particular from Helianthus Annuus which is cultivated in many countries for the production of Sunflower seed oil.
- a feature of the Invention is that it uses the Sunflower head after removal of the seeds and this part of the flower is of no value and is discarded as waste.
- the invention provides a method of extracting materials from plants, comprising mixing plant matter with one or more solvents derivable from plants, resulting in extraction into the solvent or solvents of material from the plant matter.
- the plant matter conveniently comprises flowers or flower heads (without petals) , which may be in fresh or dried condition.
- the plant matter may be reduced to smaller pieces for processing, e.g. by cutting, shredding or grinding.
- the solvent or solvent mixture conveniently comprises one or more terpenes (including sesquiterpenes, diterpenes and higher polymers and various oxygen-containing compounds from terpenes, such as alcohols, eg terpineol, ketones and camphors) and plant oils e.g. rosemary oil and lavender oil.
- terpenes including sesquiterpenes, diterpenes and higher polymers and various oxygen-containing compounds from terpenes, such as alcohols, eg terpineol, ketones and camphors
- plant oils e.g. rosemary oil and lavender oil.
- terpenes include the terpenes, terpineol, D-limonene, -pinene, ⁇ -pinene and mixtures thereof, e.g. a mixture of equal parts by weight of terpineol and D-limonene.
- the mixture is preferably agitated or stirred, desirably in a way that reduces the size of pieces of the plant matter to expose a greater surface area of plant matter to the solvent and increase the speed of the extraction process.
- This is conveniently achieved using a mechanical macerating mixer. Extraction starts to occur relatively rapidly (within a few minutes) even at ambient temperature (about 20°C) and occurs more rapidly with heating, and is typically complete within about 10 minutes even at ambient temperature. Heating;, however, is not currently favoured as this may cause evaporation of one or more bio-active ingredients of the material, reducing efficacy of the product.
- the residual solid plant matter is preferably removed, e.g. by filtration, leaving solvent having dissolved therein extracted plant material.
- the solvent may be removed or reduced in amount, e.g. by evaporation or distillation.
- the method is applicable to a range of plants, particularly those containing extractable bio-active materials having insecticidal, bactericidal and/or insect repellent properties.
- the method is applicable to plants of the order compos it i , in particular the Chrysanthemum family, such as marigold plants and also Leucanthemum vulgare (commonly known as the Oxeye daisy) , and the Helianthus family, such as Helianthus Annuus San Luca.
- the materials extracted by the method of the invention can find use as bio-active materials, particularly as insecticides, bactericides and/or insect repellents. Therefore, in a further aspect, the present invention provides a composition comprising extracted plant material capable of substantially repelling or killing insects, and/or killing micro-organisms. 5
- an extract solution obtained from 20 grams of dried Sunflower extracted with 100 grams of a mixture of 80 grams of D-Limonene and 20 grams of Terpineol is insecticidal as prepared.
- the present invention provides a mixture of the extract in D- Limonene or in D-Limonene and Terpineol, for example.
- the inclusion of Terpineol in the mixture can provide fungus and mould resistance.
- the invention covers material extracted by the method of the invention.
- Another aspect of the invention thus provides a composition comprising material extracted by the method of the invention.
- the composition may comprise extracted plant material in the solvent or solvents used for the extraction process, as discussed above.
- the solvent is plant-derived
- the composition may be fully plant-derived.
- the solvent or solvents may be used as a carrier for the bio- active material when formulated into a product and may be selected having regard to the intended use of the composition, to impart desired properties to the composition such as odour , evaporation rate and other physical and chemical properties .
- Such a composition may be used as it is as an insecticide, bactericide and/or insect repellent.
- composition need not include solvent used for extraction purposes.
- solvent may be removed, e.g. by evaporation or distillation.
- composition may include optional additional ingredients selected having regard to the intended use of the composition.
- a composition intended for use as an insecticidal or insect repellent cream, lotion, ointment, spray, etc may include a base or vehicle known to those skilled in the art for such purposes.
- the invention provides material obtainable from a plant from the order compos it i , in particular, a member of the Chrysanthemum family, such Leucanthemum vulgar , or a member of the Helianthus family, such as Helianthus annuus San Luca.
- the plant Iieucanthe.7iu.7i vulgare is commonly known as the Oxeye daisy. This plant grows widely in the wild in the United Kingdom and elsewhere, and is commonly regarded as a weed.
- the plant Helianthus annuus is commonly known as Sunflowers, and is cultivated in many countries for the production of Sunflower seed oil.
- the material is preferably obtained from plant matter comprising flowers or flower heads (without petals) , which may be in fresh or dried condition.
- the plant matter may be reduced to smaller pieces for processing, e.g. by cutting, shredding or grinding.
- the extracted material can be used as an ingredient of a composition, particularly a composition having insecticidal, bactericidal and/or insect repellent properties.
- the extracted material has been found to be bio-active and to having insecticidal, bactericidal and/or insect repellent properties. These properties are observed on contact with or in proximity to the material and/or vapour therefrom.
- the material is not pyrethrum-like in nature but instead may comprise a mixture of terpenes.
- the material appears to have stronger insecticidal properties than pyrethrum alone.
- the material may be easily produced using simple extraction techniques not requiring heating and the extracted active material has greater efficacy and better retention than pyrethrum from the known extraction processes.
- the invention thus provides a composition
- a composition comprising material obtainable from a plant the order compositi , in particular, a member of the Chrysanthemum family, such Leucanthemum vulgare , or a member of the Helianthus family, such as Helianthus annuus using the above described method of the first aspect of the present invention.
- a further aspect of the invention resides in a method of producing material having insecticidal, bactericidal and/or insect repellent properties, comprising extracting material from a plant from the order compositi , in particular, a member of the Chrysanthemum family, such Leucanthemum vulgare , or a member of the Helianthus family, such as Helianthus annuus San Luca.
- Extraction is preferably performed by solvent extraction, as described above.
- the method of the invention can be performed simply without the need for complex, costly equipment, and can be performed rapidly and efficiently at ambient temperature (about 20°C) . This thus provides benefits and advantages compared with the conventional method for extracting pyrethrum, as discussed above, which are complex, multi-step processes involving several high temperature steps.
- an emulsion of the solvent and water extracts in water can form a material suitable for spray application as an insecticide against flying and crawling insects.
- This mixture can form a material suitable for spray application on agricultural and horticultural plants to protect from insect pests and fungus with the additional benefit of the material being biodegradable.
- Figure 1 illustrates a graph depicting the effect of material extracted from Leucanthemum vulgare on flies.
- the terpineol acquires a maximum density of yellow colour, indicating maximum extraction. This occurs after about 10 minutes.
- the mixer is switched off, and the resulting mixture is filtered in conventional manner to remove ground flower residue, leaving a yellow liquid comprising terpineol with dissolved material extracted from Leucanthemum vulgare .
- the separated ground flower residue is rinsed with a fresh batch of terpineol to remove remaining material from the residue, and this batch of terpineol is used for extraction of the next batch of flowers.
- the yellow liquid produced by treatment of the first batch of flowers as described above has bio-active properties and may be used in this form, without further treatment, on its own or as an ingredient in a composition, e.g. an insecticidal cream, where it will exhibit bio-active properties as described above.
- the yellow liquid may be treated to remove some or all of the terpineol, e.g. by heat treatment or distillation, to produce a more concentrated product. This product can again be used on its own or as an ingredient in a composition.
- the process produces pure extracted bio-active material from dry flowers in an amount of about 5% by weight of the flowers.
- Example 2 Material produced as described in Example 1, in the form of the yellow liquid of maximum density of yellow colour, was tested for insecticidal properties. About 1 grams of the liquid was placed on filter paper and allowed to age for several hours. The filter paper was then placed in a container with live flies. All of the flies died within about 4 minutes. By way of comparison, terpineol alone used in the same way under the same conditions did not kill flies.
- Example 2 Material was produced as described in Example 1, but using D-limonene or a mixture of equal parts by weight of D- limonene and terpineol in place of terpineol.
- the extracted material in the form of the yellow liquid of maximum density of yellow colour, was used as an ingredient in an insect repellent product intended for use on the skin as protection against mosquitoes and other flying insects.
- the insect repellent product formulation was as follow:
- Non-ionic surfactant 1.0 grams
- Example 2 Material was produced as described in Example 1, but using D-limonene in place of terpineol.
- the extracted material in the form of the yellow liquid of maximum density of yellow colour, was concentrated by evaporation of the D- limonene until no solvent remains.
- the vapour produced from the remaining extracted material (which is in the form of an essential oil) has bactericidal properties, e.g. against methicillin resistant Staphylococcus aureus , Burkholder ⁇ a cepacia and Escherichia coli . Tests were carried out in a Petri dish at an appropriate temperature for bacterial culture (about 37°C) .
- Sample 2 (prepared in accordance with the invention) showed more effective results compared with sample 1 (pyrethrum) at early stages of the tests. At later stages these two samples gave similar results.
- sample 2 as compared with sample 1 indicates the presence of a more volatile bio- active component in sample 2 as compared with sample 1.
- Sample 3 gave poor results after 1 hour from start of the tests. This indicates that sample 3 contains mainly terpineol and very little extracted active material. Th s indicates that the solvent component of samples 2 and 3 is not effective against the flies, and that also it is preferred to use a Silverson mixer for extraction.
- Helianthus Annuus San Luca extracted in D-limonene in accordance with Example 1 was allowed to evaporate at room temperature and residue collected from open trays. A smear of residue approx. 2.5cm in diameter was made on aluminium foil. Flies were collected and placed in an upturned glass container. Several different species of flies were tested including black flies, midges and a type of wasp. All flies were immediately affected and showed signs of distress. When forced to come into contact with the smear, all became moribund within 15 minutes and death resulted after 1 hour.
- Extracts from Leucanthemum vulgare in D-limonene were allowed to evaporate at room temperature and residue collected from open trays. A smear of residue approx. 2.5cm in diameter was made on Whatman filter paper. This was also performed for Pyrethrum. Flies were collected and placed in an upturned glass container. Several different species of flies were tested including black flies, midges and a type of wasp.
- Flies were forced to contact the residues and were killed within 2 minutes. Flies were replenished at timed intervals and the length of time taken to kill them measured. With pyrethrum, the time increased rapidly within 24 hours, so that it took more than 9 minutes to kill the flies.
- the extract from Leucanthemum vulgare maintained its strength until after 96 hours. It was not until 200 hours after application that the Leucanthemum vulgare extract took as long to kill as pyrethrum after 24 hours.
Abstract
Method for extracting materials, particularly bio-active materials having insecticidal, bactericidal and/or insect repellent properties from plants such as those of the Chrysanthemum family or of the Helianthus family, by solvent extraction using plant-derived solvent such as terpenes e.g. terpineol and plant oils.
Description
EXTRACTION OF MATERIALS FROM PLANTS
Field of the Invention
This invention concerns the extraction of materials from plants, particularly bio-active materials, that is materials having insecticidal, bactericidal and/or insect repellent properties.
Background to the Invention
It is known to extract bio-active material known as pyrethrum from flowers of the plant Chrysanthemum cinerariae folium . Pyrethrum is a mixture of substances that acts as a powerful but non-persistent contact insecticide with rapid "knockdown" effect, while being non-toxic to mammals.
The normal methods of extraction of pyrethrum are complex, multi-step processes that involve heating of organic solvents derived from petroleum, and require several stages of concentration, selective separation and refinement which are carried out using expensive equipment. A typical pyrethrum extraction process involves the following steps:
1. Flowers are gathered at full bloom
2. Flowers are dried, usually in the open air.
3. Dried flowers are transported to a central processing facility.
4. Dried flowers are ground to fine powder.
5. Ground flowers are extracted using hexane solvent at elevated temperature.
6. Hexane solvent is distilled off leaving a dark tarry oleoresin.
7. Oleoresin is refined by further selective solvent extraction performed at elevated temperature to provide a light coloured liquid.
8. Refined extract is diluted using mineral oil to form a 25% (by weight) solution ready for sale and use.
The process produces approximately 3% by weight pure pyrethrum extract from dry flowers.
The present invention is based on a novel method of extracting materials from plants. The present invention further concerns extraction of bio-active material and associated material from the order compositi , in particular of plants in the Chrysanthemum family and of plants in the Helianthus family commonly known as Sunflowers, in particular from Helianthus Annuus which is cultivated in many countries for the production of Sunflower seed oil. A feature of the Invention is that it uses the Sunflower head after removal of the seeds and this part of the flower is of no value and is discarded as waste.
fiιιmnιaτγ of the Invention
In a first aspect, the invention provides a method of extracting materials from plants, comprising mixing plant matter with one or more solvents derivable from plants, resulting in extraction into the solvent or solvents of material from the plant matter.
The plant matter conveniently comprises flowers or flower heads (without petals) , which may be in fresh or dried condition.
The plant matter may be reduced to smaller pieces for processing, e.g. by cutting, shredding or grinding.
The solvent or solvent mixture conveniently comprises one or more terpenes (including sesquiterpenes, diterpenes and higher polymers and various oxygen-containing compounds from terpenes, such as alcohols, eg terpineol, ketones and camphors) and plant oils e.g. rosemary oil and lavender oil. Currently preferred plant solvents include the terpenes, terpineol, D-limonene, -pinene, β-pinene and mixtures thereof, e.g. a mixture of equal parts by weight of terpineol and D-limonene.
The mixture is preferably agitated or stirred, desirably in a way that reduces the size of pieces of the plant matter to expose a greater surface area of plant matter to the solvent and increase the speed of the extraction process. This is conveniently achieved using a mechanical macerating mixer. Extraction starts to occur relatively rapidly (within a few
minutes) even at ambient temperature (about 20°C) and occurs more rapidly with heating, and is typically complete within about 10 minutes even at ambient temperature. Heating;, however, is not currently favoured as this may cause evaporation of one or more bio-active ingredients of the material, reducing efficacy of the product.
After extraction, the residual solid plant matter is preferably removed, e.g. by filtration, leaving solvent having dissolved therein extracted plant material.
Alternatively, the solvent may be removed or reduced in amount, e.g. by evaporation or distillation.
The method is applicable to a range of plants, particularly those containing extractable bio-active materials having insecticidal, bactericidal and/or insect repellent properties. In particular the method is applicable to plants of the order compos it i , in particular the Chrysanthemum family, such as marigold plants and also Leucanthemum vulgare (commonly known as the Oxeye daisy) , and the Helianthus family, such as Helianthus Annuus San Luca.
The materials extracted by the method of the invention can find use as bio-active materials, particularly as insecticides, bactericides and/or insect repellents. Therefore, in a further aspect, the present invention provides a composition comprising extracted plant material capable of substantially repelling or killing insects, and/or killing micro-organisms.
5
It has been found that an extract solution obtained from 20 grams of dried Sunflower extracted with 100 grams of a mixture of 80 grams of D-Limonene and 20 grams of Terpineol is insecticidal as prepared. Thus, in a further aspect, the present invention provides a mixture of the extract in D- Limonene or in D-Limonene and Terpineol, for example. The inclusion of Terpineol in the mixture can provide fungus and mould resistance.
In yet a further aspect the invention covers material extracted by the method of the invention.
It has also been found that a solution in D-Limonene, when allowed to evaporate to remove the D-Limonene leaves a residue of extracted material which is both repellent and insecticidal to flies.
Another aspect of the invention thus provides a composition comprising material extracted by the method of the invention.
In a simple case, the composition may comprise extracted plant material in the solvent or solvents used for the extraction process, as discussed above. As the solvent is plant-derived, the composition may be fully plant-derived. The solvent or solvents may be used as a carrier for the bio- active material when formulated into a product and may be selected having regard to the intended use of the composition, to impart desired properties to the composition such as odour , evaporation rate and other physical and chemical properties .
Such a composition may be used as it is as an insecticide, bactericide and/or insect repellent.
The composition need not include solvent used for extraction purposes. Such solvent may be removed, e.g. by evaporation or distillation.
The composition may include optional additional ingredients selected having regard to the intended use of the composition. For example, a composition intended for use as an insecticidal or insect repellent cream, lotion, ointment, spray, etc may include a base or vehicle known to those skilled in the art for such purposes.
In yet a further aspect, the invention provides material obtainable from a plant from the order compos it i , in particular, a member of the Chrysanthemum family, such Leucanthemum vulgar , or a member of the Helianthus family, such as Helianthus annuus San Luca.
The plant Iieucanthe.7iu.7i vulgare is commonly known as the Oxeye daisy. This plant grows widely in the wild in the United Kingdom and elsewhere, and is commonly regarded as a weed.
The plant Helianthus annuus is commonly known as Sunflowers, and is cultivated in many countries for the production of Sunflower seed oil.
The material is preferably obtained from plant matter comprising flowers or flower heads (without petals) , which may be in fresh or dried condition. The plant matter may be reduced to smaller pieces for processing, e.g. by cutting,
shredding or grinding.
The extracted material can be used as an ingredient of a composition, particularly a composition having insecticidal, bactericidal and/or insect repellent properties. The extracted material has been found to be bio-active and to having insecticidal, bactericidal and/or insect repellent properties. These properties are observed on contact with or in proximity to the material and/or vapour therefrom. Not wishing to be bound by theory, it is thought that the material is not pyrethrum-like in nature but instead may comprise a mixture of terpenes. The material appears to have stronger insecticidal properties than pyrethrum alone. Moreover, the material may be easily produced using simple extraction techniques not requiring heating and the extracted active material has greater efficacy and better retention than pyrethrum from the known extraction processes.
In a further aspect the invention thus provides a composition comprising material obtainable from a plant the order compositi , in particular, a member of the Chrysanthemum family, such Leucanthemum vulgare , or a member of the Helianthus family, such as Helianthus annuus using the above described method of the first aspect of the present invention.
In another aspect of the invention provides a method of killing or repelling insects or killing microorganisms, comprising exposure to material extractable from the plant Leucanthemum vulgare or Helianthus annuus San Luca.
A further aspect of the invention resides in a method of producing material having insecticidal, bactericidal and/or insect repellent properties, comprising extracting material from a plant from the order compositi , in particular, a member of the Chrysanthemum family, such Leucanthemum vulgare , or a member of the Helianthus family, such as Helianthus annuus San Luca.
Extraction is preferably performed by solvent extraction, as described above.
The method of the invention can be performed simply without the need for complex, costly equipment, and can be performed rapidly and efficiently at ambient temperature (about 20°C) . This thus provides benefits and advantages compared with the conventional method for extracting pyrethrum, as discussed above, which are complex, multi-step processes involving several high temperature steps.
Furthermore, an emulsion of the solvent and water extracts in water can form a material suitable for spray application as an insecticide against flying and crawling insects. This mixture can form a material suitable for spray application on agricultural and horticultural plants to protect from insect pests and fungus with the additional benefit of the material being biodegradable.
The invention will be further described, by way of illustration, in the following Examples with References to the accompanying Figures, in which:
Figure 1 illustrates a graph depicting the effect of material extracted from Leucanthemum vulgare on flies.
In the Examples, all percentages are by weight unless otherwise stated.
Example 1
Material was extracted from the plant Leucanthemum vulgare in the following way.
Flowers of the plant Leucanthemum vulgare were gathered at full bloom or harvested at petal drop and dried in conventional manner. The dried flowers were mixed with terpineol (20 grams of dried flowers to 100 grams of terpineol) and the mixture ground at ambient temperature (about 20°C) in a high speed mechanical macerating mixer with cutting head in the form of a Silverson laboratory mixer (Silverson is a Trade Mark) , which acts to cut the dried flowers into small fragments and mix them intimately with the terpineol. Within a few minutes the colour of the terpineol starts to change, becoming yellow, as a result of solvent extraction of material from the flowers. Mixing is continued until no further colour change in the terpineol is observed, i.e. the terpineol acquires a maximum density of yellow colour, indicating maximum extraction. This occurs after about 10 minutes. The mixer is switched off, and the resulting mixture is filtered in conventional manner to remove ground flower residue, leaving a yellow liquid comprising terpineol
with dissolved material extracted from Leucanthemum vulgare .
The separated ground flower residue is rinsed with a fresh batch of terpineol to remove remaining material from the residue, and this batch of terpineol is used for extraction of the next batch of flowers.
The yellow liquid produced by treatment of the first batch of flowers as described above has bio-active properties and may be used in this form, without further treatment, on its own or as an ingredient in a composition, e.g. an insecticidal cream, where it will exhibit bio-active properties as described above. Alternatively, the yellow liquid may be treated to remove some or all of the terpineol, e.g. by heat treatment or distillation, to produce a more concentrated product. This product can again be used on its own or as an ingredient in a composition.
The process produces pure extracted bio-active material from dry flowers in an amount of about 5% by weight of the flowers.
Example 2
Material produced as described in Example 1, in the form of the yellow liquid of maximum density of yellow colour, was tested for insecticidal properties. About 1 grams of the liquid was placed on filter paper and allowed to age for several hours. The filter paper was then placed in a container with live flies. All of the flies died within about 4 minutes.
By way of comparison, terpineol alone used in the same way under the same conditions did not kill flies.
Example 3
Material was produced as described in Example 1, but using D-limonene or a mixture of equal parts by weight of D- limonene and terpineol in place of terpineol. The extracted material, in the form of the yellow liquid of maximum density of yellow colour, was used as an ingredient in an insect repellent product intended for use on the skin as protection against mosquitoes and other flying insects. The insect repellent product formulation was as follow:
Extract 3.0 grams
Water 47.0 grams
Corn Oil 47.0 grams
Alginate (seaweed extract) 2.0 grams
Non-ionic surfactant 1.0 grams
Example 4
Material was produced as described in Example 1, but using D-limonene in place of terpineol. The extracted material, in the form of the yellow liquid of maximum density of yellow colour, was concentrated by evaporation of the D- limonene until no solvent remains. The vapour produced from the remaining extracted material (which is in the form of an
essential oil) has bactericidal properties, e.g. against methicillin resistant Staphylococcus aureus , Burkholder±a cepacia and Escherichia coli . Tests were carried out in a Petri dish at an appropriate temperature for bacterial culture (about 37°C) .
Example 5
A comparison was made of the insecticidal efficacy of pyrethrum (in the form of a 25% solution in mineral oil) extracted in conventional manner and material extracted from Leucanthemum vulgare by the method of the invention.
The materials tested were as follows:
1. 25% pyrethrum solution obtained from The Pyrethrum Board of Kenya.
2. 20% solution of material prepared by the method in accordance with the invention, prepared from dried mature flowers of Leucanthemum vulgare as described in Example 1 by processing a mixture of 20 grams flower to 80 grams terpineol using a Silverson mixer.
3. 20% solution prepared as described in 2 above but using a serrated head stirrer (having a 64mm diameter serrated disc, rotating at 1000 rpm) in place of a Silverson mixer.
Equal volumes (about 0.5 grams) of the above 3 materials were placed in the centre of respective Whatman No. 1 filter papers 11cm in diameter and allowed to settle for about 1 hour uncovered at ambient temperature (about 20°C) . The resulting
colours on the filter papers were as follows:
1. medium red/brown
2. stronger red/brown
3. very little colour, indicating less effective extraction of active material.
No significant chromatographic separation of any of the samples on the filter papers occurred during this time.
Efficacy tests were carried out by placing a respective inverted glass jar or beaker over each - filter paper and placing two live flies of similar type in each container at various different times after the start of the tests. The tests were started about 1 hour after placing of samples on the filter papers. The effect of the materials on the insects with time was observed, with the time (in minutes) taken for the flies to die or become moribund being noted. Test results for the three different materials, using the same identification numbers as above, were as follows:
Time of day Material 1 Material 2 Material 3 llam 7 2 5
Noon 7 2 no effect
2pm 3 3 no effect
4pm 5 5 no effect
2am (next day) 10 12 no effect
The following remarks and observations are offered.
1. Sample 2 (prepared in accordance with the invention) showed more effective results compared with sample 1 (pyrethrum) at early stages of the tests. At later stages these two samples gave similar results.
2. The early higher efficacy of sample 2 as compared with sample 1 indicates the presence of a more volatile bio- active component in sample 2 as compared with sample 1.
3. Sample 3 gave poor results after 1 hour from start of the tests. This indicates that sample 3 contains mainly terpineol and very little extracted active material. Th s indicates that the solvent component of samples 2 and 3 is not effective against the flies, and that also it is preferred to use a Silverson mixer for extraction.
4. During the test period the colour of samples 1 and 2 gradually faded. At the end of the test sample 2 was pale yellow and sample 1 was a darker yellow/brown.
Example 6
Helianthus Annuus San Luca extracted in D-limonene in accordance with Example 1 was allowed to evaporate at room temperature and residue collected from open trays. A smear of residue approx. 2.5cm in diameter was made on aluminium foil. Flies were collected and placed in an upturned glass container. Several different species of flies were tested including black flies, midges and a type of wasp.
All flies were immediately affected and showed signs of distress. When forced to come into contact with the smear, all became moribund within 15 minutes and death resulted after 1 hour.
These results indicate that the residue is repellant In the vapour phase to the flies tested and is toxic through contact, indicating a strong insecticide action.
Example 7
Extracts from Leucanthemum vulgare in D-limonene were allowed to evaporate at room temperature and residue collected from open trays. A smear of residue approx. 2.5cm in diameter was made on Whatman filter paper. This was also performed for Pyrethrum. Flies were collected and placed in an upturned glass container. Several different species of flies were tested including black flies, midges and a type of wasp.
Flies were forced to contact the residues and were killed within 2 minutes. Flies were replenished at timed intervals and the length of time taken to kill them measured. With pyrethrum, the time increased rapidly within 24 hours, so that it took more than 9 minutes to kill the flies. The extract from Leucanthemum vulgare , however, maintained its strength until after 96 hours. It was not until 200 hours after application that the Leucanthemum vulgare extract took as long to kill as pyrethrum after 24 hours.
Claims
1. A method of extracting materials from plants, comprising mixing plant matter with one or more solvents derivable from plants, resulting in extraction into the solvent or solvents of material from the plant matter.
2. A method according to claim 1 wherein said plants belong to a family selected from the group comprising Chrysanthemum and Helianthus .
3. A method according to claim 2 wherein said plant is Leucanthemum vulgare .
4. A method according to claim 2 wherein said plant is Helianthus annuus .
5. A method according to claims 2, wherein said material is extracted from plant matter comprising flowers or flower heads, in fresh or dried condition from a plant selected from the group comprising eucanthemujn vulgare and Helianthus annuus .
6. A method according to any one of claims 1, 2, or 5 wherein said material is extracted by solvent extraction.
7. A method according to claim 6, wherein said solvent extraction is carried out using solvents derivable from plants.
8. A method according to claim 6 wherein said solvent comprises one or more terpenes and/or plant oils.
9. A method according to claim 8 wherein said solvent comprises terpineol and/or D-limonene.
10. A method according to claim 1, 2 or 5, wherein said plant matter is reduced to smaller pieces for processing.
11. A method according to any one of the preceding claims, wherein said solvent extraction is carried out at ambient temperature.
12. A method according to any one of the preceding claims wherein said solvent extraction is carried out in a mechanical macerating mixer.
13. A method according to any one of the preceding claims wherein after said extraction is performed, residual solid plant matter is removed, leaving solvent having dissolved therein extracted plant material.
14. A method according to claim 13 wherein after removal of residual solid plant matter, solvent is removed or reduced in amount.
15. A method according to any one of claims 1 to 14 wherein the material produced has insecticidal, bactericidal and/or insect repellent properties.
16. Insecticidal, bactericidal and/or insect repellant material extracted from a plant by the method of any one of the preceding claims.
17. Material from a plant belonging to the order compositi , wherein said material is obtainable by extracting the material from plants using one or more solvents derivable from plants.
18. Material according to claim 17 wherein said material is obtainable from a plant belonging to a family selected from the group comprising Chrysanthemum and Helianthus .
19. Material according to claim 18 wherein said material is obtainable from the plant Leucanthemum vulgare .
20. Material according to claim 18 wherein said material is obtainable from the plant Helianthus annuus .
21. Material according to any one of claims 17 to 20 wherein said material is obtainable from plant matter comprising flowers or flower heads, in fresh or dried condition.
22. Material according to any one of claim 17 to 21 wherein said material is obtainable by solvent extraction.
23. Material according to claim 22 wherein said solvent extraction is carried out using one or more solvents derivable from plants.
24. Material according to claim 23 wherein said solvent comprises one or more terpenes or plant oils.
25. Material according to claims 22, 23 or 24, wherein said solvent extraction is performed at ambient temperature.
26. A insecticidal, bactericidal and/or insect repellant composition comprising material in accordance with any one of claims 17 to 25 and a carrier.
27. A composition according to claim 26 wherein said composition further comprises one or more solvents used for extraction of the material.
28. A composition according to claim 27 wherein said one or more solvents are plant-derived.
29. A composition according to claims 26, 27 or 28 in the form of an insecticidal, bactericidal or insect repellent composition.
30. A method of killing or repelling insects or killing micro-organisms, said method comprising exposing said insects or micro-organisms to a material or composition in accordance with any one of claims 16 to 29.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU61721/00A AU6172100A (en) | 1999-07-27 | 2000-07-27 | Extraction of materials from plants |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9917504.4 | 1999-07-27 | ||
GB9917505.1 | 1999-07-27 | ||
GB9917504A GB2352396A (en) | 1999-07-27 | 1999-07-27 | Extraction of bio-active materials from Oxeye daisy plants |
GB9917505A GB2352397A (en) | 1999-07-27 | 1999-07-27 | Extraction of materials from plants |
GB9919724.6 | 1999-08-20 | ||
GB9919724A GB9919724D0 (en) | 1999-07-27 | 1999-08-20 | Extraction of material from flowers |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2001007135A1 true WO2001007135A1 (en) | 2001-02-01 |
WO2001007135A2 WO2001007135A2 (en) | 2001-02-01 |
WO2001007135A8 WO2001007135A8 (en) | 2001-04-05 |
Family
ID=27269783
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2000/002870 WO2001007135A2 (en) | 1999-07-27 | 2000-07-27 | Extraction of materials from plants |
Country Status (2)
Country | Link |
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AU (1) | AU6172100A (en) |
WO (1) | WO2001007135A2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100418423C (en) * | 2006-08-11 | 2008-09-17 | 云南大学 | Active compound extracted from pyrethrum and use thereof |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20020059369A (en) * | 2000-06-23 | 2002-07-12 | 다쿠오 사카이 | process for production plant-origin antibacterial substance |
FR2892933B1 (en) * | 2005-11-10 | 2010-11-05 | Herve Andre Gerard Durand | PLANT EXTRACT OBTAINED BY A PROCESS OF EXTRACTION USING SOLVENTS OF VEGETABLE ORIGIN |
WO2018023069A1 (en) * | 2016-07-29 | 2018-02-01 | Tapio Olavi Kristain MAKI | Methods, devices, and systems for extraction of oils from plant matter |
FR3110422B1 (en) * | 2020-05-19 | 2023-03-17 | Int Flavors & Fragrances Inc | Lavandula absolute for its cosmetic use |
WO2024054738A1 (en) * | 2022-09-08 | 2024-03-14 | Young Living Essential Oils, Lc | Methods and systems for extracting additional beneficial lipid-soluble compounds from plant materials in environmentally sustainable ways |
-
2000
- 2000-07-27 WO PCT/GB2000/002870 patent/WO2001007135A2/en active Application Filing
- 2000-07-27 AU AU61721/00A patent/AU6172100A/en not_active Abandoned
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100418423C (en) * | 2006-08-11 | 2008-09-17 | 云南大学 | Active compound extracted from pyrethrum and use thereof |
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