GB2469167A - Extraction of 8-hydroxyquinoline and other components from knapweed - Google Patents

Extraction of 8-hydroxyquinoline and other components from knapweed Download PDF

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Publication number
GB2469167A
GB2469167A GB1002502A GB201002502A GB2469167A GB 2469167 A GB2469167 A GB 2469167A GB 1002502 A GB1002502 A GB 1002502A GB 201002502 A GB201002502 A GB 201002502A GB 2469167 A GB2469167 A GB 2469167A
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Prior art keywords
hydroxyquinoline
knapweed
hydrosol
oil
cnicin
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Withdrawn
Application number
GB1002502A
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GB201002502D0 (en
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Russell Taylor
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Individual
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Individual
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Publication of GB201002502D0 publication Critical patent/GB201002502D0/en
Publication of GB2469167A publication Critical patent/GB2469167A/en
Priority to GBGB1020050.9A priority Critical patent/GB201020050D0/en
Withdrawn legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Mycology (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Pest Control & Pesticides (AREA)
  • Virology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A natural source of 8-hydroxyquinoline is disclosed and the process described therein, which involves steam distillation, results in the extraction of 8-hydroxyquinoline, as well as the compounds cnicin and (-) catechin from the herbage and root material of a plant called Centaurea Diffusa (Knapweed). The hydrosol obtained from this process that contains the above three components finds use as an organic spray for insect control. Furthermore, the said hydrosol may be further treated to produce an aqueous based metal ion chelating composition that consists 8-hydroxyquinoline, useful for the treatment of bacterial and various medical conditions.

Description

Description
8-hydroxyquinoline, a natural metal ion chelating compound, has been found in the roots and herbage of Centaurea diffusa, along with Cnicin and (-) Catechin compounds. This invention relates to its extraction and formulation to obtain full benefit of the compounds properties in treating various medical conditions within humans and animals.
Centaurea difftisa (a variety of Knapweed) is a naturally occurring plant from the Balkans which has today become a rather prolific weed in many parts of the world especially in the United States where it has been described as the number one weed. Within the Knapweed species there are many varieties and all of them do have some interesting chemicals present. However Centaurea diffusa is the most interesting species as it has present, 8-hydroxyquinoline, Cnicin and (-) catechin which all have interesting properties. It has been shown that the root structure of the Centaurea diffusa actually exudes 8-hydroxyquinoline, Cnicin and (-) Catechin into the soil surrounding each plant with the purpose of eliminating other plants that may absorb the minerals and food that the Centaurea diffusa may require. It has been shown that the concentration of 8-hydroxyquinoline in the soil surrounding a centaurs diffusa plants on a 600mm radius the level of 8-hydroxyquinoline is around 450 ppm which is an unusual high figure, and Cnicin up to around 1.0% and C-) Catechin at 0.2% . It has been shown that 2 off the chemicals present in the root structure and the herbage are in the range of very similar to the range of the ground content of 8-hydroxyquinoline and the (-) catechin., but the Cnicin is higher.
(-) catechin is a compound that is present in green tea and is regarded as being an anti cancer agent in the range of 0.2%. Cnicin is an unusual compound and is also anti-cancerous and anti-bacterial and has ranged in the ground up to 1% but in the herbage during different times of the year from 2.0% up to 3.2%., With 8-hydroxyquinoline the compound has been around since 1632 where it was a component in the anti-malarial compound produced from a tree in Peru and today with other patents and patents pending associated with the inventor of this patent, have been shown to be a excellent treatment for killing bacteria which includes MRSA and other super bugs, all forms of cancer, various gastro-intestinal conditions, adverse wounds, peripheral neuropathy and many other medical applications.
The invention attributed to producing this unique distillate and its hydrosol is in the method of distillation where the maximum yield can be achieved and that a range of other phytochemicals will be extracted at the same time which appear to be beneficial.
When distilling the herbage material, for every litre of oil produced, we normally get 20 litres of hydrosol which contains the aqueous isomers of the isomers in the oil mixture and is of use in plant pest control.
To recover the mixture of 8-hydroxyquinoline,Cnicin and (-) catechin the invention in the form of a unique distillation unit is described as follows; INVENTION.
LOW PRESSURE FIELD DISTILLATION UNiT
BOILER: The boiler was constructed in cylindrical shape and measured 1500 mm high by 900 mm across.
The firebox area was 300 mm high and had three LPG burners located in the space available.
Two are connected together and the third was independent.
Three burners were used to heat the boiler to the point of steam and beyond until steam penetrated the load of herbage material in the bin and steam started to pass through the condenser into the separator. At this point the third burner was turned off and the remaining two were sufficient to complete the distillation process.
Above the firebox plate a series of 25 mm steel tubes led through the water chamber to the top sealed compartment. In addition to the burners applied direct the firebox plate, these also assisted in funnelling the heat into the top chamber. A 100 mm flue dispersed the excess heat from the boiler.
A series of copper pipes led through the water chamber to the top compartment, where they were arranged so that they passed over the top of the tubes bringing direct heat from the firebox. This created the super heating process necessary to achieve the temperatures as high as 115 degrees Centigrade.
Water levels in the steam producing pipes was maintained at an appropriate level by a float chamber on the outside of the still.
It was found that by re-introducing heated water from the condenser that the efficiency of the still was even further improved by not having to heat the incoming water from tap temperature.
Water supply was sustained from an ordinary nineteen millimetre garden hose.
A flexible rubber stem pipe connected between the Boiler and the Bin using quick release level attachments. This was kept as short as possible to minimise temperature loss.
A temperature probe and gauge was fitted at the point of entry of the stem to determine the temperature and the need to use the third burning if necessary to maintain the optimum temperature
DISTILLATION BIN
The bin, which measured 1500mm x 1500mm x 1500 was constructed with a central core out of 306 stainless steel 16 gauge plate inside an angle iron frame that was filled with insulation material and covered in flat galvanised sheeting.
The stainless steel lining is essential against the nature of the Knapweed Oil, as is any metal connections on the passage of the steam/oil combination throughout the distillation process.
The Bin was designed with 14 inch tyres to enable it to be moved around the property to facilitate loading with chipped/ground herbage material and to unload the bin after the distillation process is completed. To further aide in the quick turn around between distillations the trailer designed bin was also constructed so that it could be tipped upside down to empty the contents.
The removable lid of the chamber is of similar construction with a 50 mm outlet which joins to the Condenser.
CONDENSER
The condenser was built of 306 Stainless steel sheet bent to form a tube of approximately 200 mm diameter. Inside this tube were twelve small stainless steel tubes, passing through three stainless steel baffle sheets located at each end and in the middle. Each 20 mm tube had a twisted 19 mm Stainless steel flat strip inserted, running the length of the tube to ensure that the condensate remained in the tube long enough for the condensation process to separate the oil and water.
The Condenser was approximately 1.5 metres long and was cone shaped on each end to disperse the condensate as required. The liquid when condensed to a combination of oil and water from the steam entering the Condenser was passed through to a separator.
SEPARATOR
The separator was also built of 306 55 material and was 500 mm in diameter and approximately 450 mm high. A glass indicator column was fitted to the top to enable the oil level to be seen and the oil separated from the Hydrosol as required. S 4
The whole distillation unit could be moved from area to area with a small utility vehicle, by putting the boiler and peripheral equipment in the back of the utility vehicle and towing the mobile bin behind the vehicle.
Procedure.
To ensure maximum recovery of the oil and hydrosol, the herbage, which includes the roots, stalks, stems and leaves are chipped or ground down to less than 6 mm in size, This ground herbage is then placed in the distillation bin ready to be treated. The process plant is then started up to run through a 2 hour cycle with constant monitoring of the temperatures being used.
We have found that with this process plant compared to a process plant we used earlier was that the yield of the oil went up by 100% and the composition of the 3 compounds increased but at the same time additional phytochemicals appeared. The amount of hydrosol produced was at the ratio of 20 litres per litre of oil produced.
Analysis of the Hydrosol indicated up to 52% of the aqueous isomers of the 3 compounds were present, together with a range of minor phytochemicals.
We compared the yield of oil and hydrosol with trials we did in Australia on the Backhousia citridora and they were very similar.
Once the oil is separated an analysis is carried out to ascertain the value of the various chemical compounds. With the 8-hydroxyquinoline it is possible to precipitate it out of the solution by the addition of a lèrrous ion and then the mixture is filtered and the residue is then treated to remove the ferrous ion and a reasonable grade of 8-hydroxyquinoline is available With this invention of the extraction unit and the resulting liquid compound available it is possible to manulcture a liquid composition that has anti-bacterial, anti-viral, anti-fungal creme which is very effective against MRSA/MSSWVRSA and also various other skin disorders.
With the invention of the extraction unit and the resulting liquid compound it is possible to extract 8-hydroxyquinoline from it. The precipitate from the 8-hydroxyquinoline is then mixed with a wetting agent and a diluent being propylene glycol and heated to 70 degrees centigrade being stirred at the same time to achieve a base for an aqueous solution. Depending on the 8-Hydroxyquinoline analysis will dictate the strength of this solution. It is normally diluted further to around a 2% concentration and held as a base * 5 product. When used for various products a percentage of the base liquid is taken and diluted further with distilled water to achieve the end result desired.
With the invention of the extraction uni and the resulting hydrosol it is possible to use one part of the hydrosol to 4 parts of water to manufacture a spray for vegetables and flowers that qualifies for an environmentally safe spray classification as the insects and bugs killed can be consumed by birds leaving no toxic effect. This is an unique beneficial effect.
Trials were held on the basic oil diluted with other water soluble oil and it was found that as a residual spray it was very effective especially in stables and animal sheds/barns in lowering the fly population.

Claims (6)

  1. Claims I claim; 1. That by the process described 8-hydroxyquinoline which is present in Knapweed (Difftisa variety) can be extracted and converted into a metal ion chelation agent that is aqueous based.
  2. 2. That the 8-hydroxyquinoline from the Knapweed can be used to treat bacterial and adverse medical conditions then formulated as outlined.
  3. 3, That the 8-hydroxyquinoline being extracted from a plant can be classified as a naturally sourced material.
  4. 4. That the use of the combined mixture with 8-hydroxyquinoline, Cnicin, and (-) Catechin can be made into a anti-bacterial, anti-viral and anti-fungal crème.
  5. 5. That the hydrosol which is a by-product from the oil production has a use as an organic insecticide spray where the insects killed are non-toxic to birds.
  6. 6. That a mixture of the original opil distilled diluted with a water soluble oil and then water provides a suitable residual spray that lowers the insect population in stables and barns.
GB1002502A 2009-04-01 2010-02-15 Extraction of 8-hydroxyquinoline and other components from knapweed Withdrawn GB2469167A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GBGB1020050.9A GB201020050D0 (en) 2009-04-01 2010-11-26 The invention relates to the extraction of 8-Hydroxyquinoline, Cnicin and (-) Catechin from a plant called Centaurea Diffusa (Knapweed)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB0905650.8A GB0905650D0 (en) 2009-04-01 2009-04-01 This invention relates to the extraction of 8-hydroxyquinoline from a plant called centaurea diffusa (knapweed) for the purpose of manufacture of an aqueous

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GB201002502D0 GB201002502D0 (en) 2010-03-31
GB2469167A true GB2469167A (en) 2010-10-06

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Application Number Title Priority Date Filing Date
GBGB0905650.8A Ceased GB0905650D0 (en) 2009-04-01 2009-04-01 This invention relates to the extraction of 8-hydroxyquinoline from a plant called centaurea diffusa (knapweed) for the purpose of manufacture of an aqueous
GB1002502A Withdrawn GB2469167A (en) 2009-04-01 2010-02-15 Extraction of 8-hydroxyquinoline and other components from knapweed
GBGB1020050.9A Ceased GB201020050D0 (en) 2009-04-01 2010-11-26 The invention relates to the extraction of 8-Hydroxyquinoline, Cnicin and (-) Catechin from a plant called Centaurea Diffusa (Knapweed)

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GBGB0905650.8A Ceased GB0905650D0 (en) 2009-04-01 2009-04-01 This invention relates to the extraction of 8-hydroxyquinoline from a plant called centaurea diffusa (knapweed) for the purpose of manufacture of an aqueous

Family Applications After (1)

Application Number Title Priority Date Filing Date
GBGB1020050.9A Ceased GB201020050D0 (en) 2009-04-01 2010-11-26 The invention relates to the extraction of 8-Hydroxyquinoline, Cnicin and (-) Catechin from a plant called Centaurea Diffusa (Knapweed)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005039289A2 (en) * 2003-10-24 2005-05-06 Colorado State University Research Foundation Herbicidal compositions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005039289A2 (en) * 2003-10-24 2005-05-06 Colorado State University Research Foundation Herbicidal compositions

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GB201020050D0 (en) 2011-01-12
GB0905650D0 (en) 2009-05-13

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