WO2003002133A2 - Stabilisation de chlorophylle - Google Patents

Stabilisation de chlorophylle Download PDF

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Publication number
WO2003002133A2
WO2003002133A2 PCT/GB2002/002893 GB0202893W WO03002133A2 WO 2003002133 A2 WO2003002133 A2 WO 2003002133A2 GB 0202893 W GB0202893 W GB 0202893W WO 03002133 A2 WO03002133 A2 WO 03002133A2
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WO
WIPO (PCT)
Prior art keywords
formulation
medium chain
extract
acid
chain triglyceride
Prior art date
Application number
PCT/GB2002/002893
Other languages
English (en)
Other versions
WO2003002133A3 (fr
Inventor
Piotr Marek Kalinowski
Original Assignee
Oaklea Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Oaklea Ltd filed Critical Oaklea Ltd
Priority to AU2002317275A priority Critical patent/AU2002317275A1/en
Publication of WO2003002133A2 publication Critical patent/WO2003002133A2/fr
Publication of WO2003002133A3 publication Critical patent/WO2003002133A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters

Definitions

  • the invention relates to a formulation of chlorophyll extract or chlorophyll dissolved, suspended or dispersed in an oil made from the esterification of fatty acids and glycerol. More particularly, the invention relates to a formulation of chlorophyll extract or chlorophyll in a medium chain triglyceride oil.
  • chlorophyll as a component of food e.g. in dark-green leafy vegetables, as a healthfood supplement, as a natural colourant for food, in cosmetic products and toiletry products and for pharmaceutical purposes such as deodorants and surgical dressings.
  • chlorophyll In nature, the role of chlorophyll is fundamental to the process of photosynthesis.
  • chlorophylls are well able to survive the highly destructive effects of photo-oxidation arising from free radicals created largely by the partial re-reduction of oxygen released following the photosplitting of water, i.e. 2H2O - 4H+ + 4e- + O2. This is due to the stable and specialised chlorophyll/polypeptide complex found in plant chloroplasts creating a protective environment.
  • the photosynthetic apparatus is surrounded by a complete complement of antioxidants, such as tocopherols, carotenoids and vitamin C (Salin M.L. Physiol. Plant 1987 72 pp681-689).
  • Chlorophyll is a magnesium-chelated porphyrin, which, in its excited state, is a strong reducing agent. If the electron deficiency is not rapidly balanced, as occurs during photosynthesis, the excited chlorophyll will combine with oxygen. Purified chlorophylls are especially unstable in the presence of dilute acids and in light. (Hendry & Houghton. ibid).
  • chlorophylls a and b (commonly found in algae, some photosynthetic bacteria and all higher plants) become demetalated to pheophytins a and b.
  • This loss of the magnesium ion is accompanied by a characteristic, distinct and readily visible colour change.
  • the natural colour of chlorophyll a is bright blue-green and chlorophyll b is bright greenish-yellow.
  • Both their respective pheophytins are variously described as brown in colour (Scheer.H. Handbook of Chromatography, Plant Pigments Ed. Kost H.P. 1987 Vol 1 p.250 CRC Press) or green-grey in colour (Hendry GAF, pers com).
  • the generally adopted solution is to allow or promote the natural degradation to pheophytin to take place. Then two of the four hydrogen ions in the porphyrin ring are replaced with a copper ion rather than the (natural) magnesium ion. This is achieved by adding a copper salt or solution, in stochiometric proportion to the pheophytin present, to the extract.
  • the resulting blue-green copper chlorophyllins are relatively resistant to both light and to acidic conditions (Hendry & Houghton. ibid).
  • Such a carefully made extract will have the added benefit of helping to preserve other labile components present in green plant material such as the carotenoids, tocopherols, glycolipids, fatty acids, sterols, etc.
  • Such an extract would have valuable nutritional and dietary benefits for humans and for animals. It could also be used as a totally natural green colourant.
  • chlorophyll extracts Due to such chlorophyll extracts being derived from naturally mutable substrates, they will also be inherently variable. They will require a diluent to aid in the standardisation of the product. Different products will need different levels of dilution.
  • chlorophyll extracts are only oil-soluble, the simplest and most appropriate diluents would be vegetable oils.
  • a non-exhaustive list would include oils derived from corn, cottonseed, soybeans, sunflower seeds, peanuts, olives, rapeseed, linseed and the like. They are readily available, relatively cheap and are acceptable by regulatory authorities for such purposes.
  • chlorophylls a and b decompose to their respective pheophytins under the influence of hydroperoxides in vegetable oils (The Decomposition of Chlorophylls into Pheophytins during the Autoxidation of Rapeseed Oil. Bratkowska and Niewiadomski. Rocz. Technol. Chem. Zyw. 1970 18 69-75. in Polish with English summary).
  • alfalfa also known as lucerne (Medicago sativa)
  • lucerne Medicago sativa
  • the alfalfa extract when dissolved in acetone, was a bright blue-green colour indicating the presence of chlorophylls a and b.
  • Portions of the alfalfa extract were dissolved separately in corn, olive, peanut and sunflower oils at a ratio of one part oil to one part extract.
  • Opaque (lightproof) plastic containers were filled to the brim with the mixtures, so as to minimise the headspace and therefore the oxygen present.
  • the containers were kept at a constant 42° C for a month. This approximates to an accelerated ageing of the contents equivalent to six months at ambient temperatures.
  • a formulation comprising an extract of a green photosynthetic plant material containing chlorophyll dissolved, suspended or dispersed in one or more medium chain triglyceride oils (also commonly referred to as MCT oils).
  • MCT oils also commonly referred to as MCT oils.
  • the one or more medium chain triglyceride oils are selected from a range wherein the fatty acid is C 6 to C- ⁇ 2 fatty acid.
  • the fatty acid is a C 8 to C ⁇ o fatty acid. More preferably the fatty acid is caproic acid, caprylic acid, capric acid or lauric acid.
  • the formulation may contain up to 98% by weight of the photosynthetic plant extract. Preferably the formulation contains 20-80% percent by weight of the extract.
  • the formulation may contain less than 20% by weight of the extract.
  • the photosynthetic plant extract contains chlorophyll wholly or largely in its natural undegraded state.
  • the formulation may include one or more oil-soluble antioxidants.
  • the one or more anti-oxidants may be chosen from the following: synthetic or natural tocopherols, tocotrienols, butylated hydroxytoluene, butylated hydroxyanisole, tertiary butylhydroquinone, ethoxyquin, ascorbyl palmitate, propyl gallate and extracts derived from herbs such as rosemary or mixtures of these, whether synergistic or not.
  • the formulation may include one or more complexing agents.
  • the one or more complexing agents may be chosen from the following: citric acid, tartaric acid, ethylene diamine tetra-acetic acid, salts or esters of the aforementioned acids, and lecithin.
  • a formulation as described in the first aspect of the present invention comprising fresh, part dried or dried green photosynthetic plant material containing chlorophyll suspended or dispersed in a medium chain triglyceride oil.
  • Fresh alfalfa leaves were ground in a Waring Blendor with an approximately equal weight of chilled acetone.
  • the pH was adjusted to about 7.5 using dilute sodium hydroxide.
  • the mixture was filtered in a vacuum filter and the supernatant liquid, which had a pale green colour, was discarded.
  • a further equal weight of acetone was added.
  • the supernatant was now a bright blue- green colour, indicating chlorophyll had been extracted.
  • the supernatant was removed by vacuum filtration and the extraction procedure was repeated twice further, after which there was no useful further material left to be extracted.
  • the three extracts were combined and the acetone solvent removed under vacuum.
  • extract described in the previous paragraph was divided and mixed with 'Radiamuls' MCT oil in the proportions 1 :1 , 1 :2, 1 :25 and 1 :50 (extrac oil). They were stored in tightly-stoppered opaque plastic bottles, in a dark place and at room temperature, for one year. Their colour at the end of that time remained bright blue-green.
  • extract refers to an extract of a green photosynthetic plant material present in a parent material composed of fresh, frozen, dried or otherwise preserved, green photosynthetic plant matter.
  • This parent material is subjected to extraction procedures commonly, but not exclusively, using polar or non-polar solvents or mixtures of such solvents.
  • extractions need to be carefully carried out using techniques known to those skilled in the art, so as to avoid the chlorophylls and/or other labile components present in the original plant material becoming degraded during extraction.
  • Green, photosynthetic plant matter includes all higher plants, all those algae possessing photosynthetic organelles known as chloroplasts, blue-green algae and photosynthetic bacteria that contain chlorophyll in any of its chemical forms.
  • a chlorophyll is typically a magnesium complex of dihydroporphyrins or tetrahydroporphyrins usually but not always with an attached esterifying alcohol group, usually phytol.
  • the polar and/or non-polar solvents may be removed from the extract either before the addition of the medium chain triglyceride oil as diluent, or after its addition as diluent.
  • the latter method is in accordance with patent number GB2256600.
  • the extract may be maintained in an inert atmosphere or a vacuum to prevent decomposition.
  • the diluent oil may be derived from the esterification of fatty acids and glycerol.
  • fatty acids and glycerol Preferably substantially pure fatty acids and glycerol are used for the esterification.
  • the fatty acids are purified by distillation.
  • oils which have only relatively recently been commercialised, are commonly and generically known as 'medium chain triglyceride oils' (or MCT oils).
  • MCT oils MCT oils
  • a non-exhaustive list of manufacturers and suppliers of such oils includes Oleon under their tradename 'Radiamuls', Cognis under their tradename 'Delios' and Stepan Co under their tradename 'Neobee'.
  • the one or more optional antioxidants may be added to the product in such proportions, as are known to persons skilled in the art, so as to provide effective antioxidant benefit.
  • the one or more optional complexing agents may be added to the product in such proportions, as are known to persons skilled in the art, so as to provide effective benefit.
  • the formulation may include, as well as a medium chain triglyceride oil, other triglyceride oils.
  • the formulation may be of fresh, part-dried or dried green photosynthetic plant material suspended or dispersed in a medium chain triglyceride oil.
  • the plant material may be entire or may be cut, crushed or ground into a finer state.
  • oils derived from the esterification of fatty acids and glycerol as opposed to using commonly available vegetable oils extracted from seeds or fruits by solvent extraction or by cold-pressing
  • the most suitable oils are those wherein the chain length of the fatty acid is between C ⁇ and C12.
  • oils as diluents are their natural low viscosity (about one third of the viscosity of normal vegetable oils), and low melting point (about -15°C) This considerably reduces the proportion of diluent oil required to achieve a predetermined level of viscosity in the final mixed product. Such a mixture may then be stored, if required, at chill-room temperatures yet still remain handleable by being easy-flowing.
  • a further usefulness of such oils is related to their physiological properties.
  • Conventional vegetable oils contain long chain fatty acids. They are absorbed by the body relatively slowly because they need to be hydrolysed in the intestine and then transported by the lymphatic system to be deposited in adipose tissues.
  • Medium chain triglycerides having a lower molecular weight, are rapidly absorbed by the body without needing initial intestinal hydrolysis and are transported through the much faster portal vein system directly to the liver. Here they are rapidly oxidised as an immediate energy source.
  • other oil- soluble compounds for example vitamins, that are dissolved or dispersed in the medium-chain triglyceride oil, are known to be more rapidly absorbed by the body.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Biotechnology (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Medical Informatics (AREA)
  • Botany (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention concerne une formulation comprenant un matériau formant plante de photosynthèse verte ou un extrait de ce dernier dissous, en suspension ou dispersé dans une huile de triglycéride à chaîne moyenne.
PCT/GB2002/002893 2001-06-29 2002-06-24 Stabilisation de chlorophylle WO2003002133A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002317275A AU2002317275A1 (en) 2001-06-29 2002-06-24 Stabilisation of chlorophyll using medium chain triglyceride oils

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0115982A GB0115982D0 (en) 2001-06-29 2001-06-29 Stabilisation of chlorophyll
GB0115982.1 2001-06-29

Publications (2)

Publication Number Publication Date
WO2003002133A2 true WO2003002133A2 (fr) 2003-01-09
WO2003002133A3 WO2003002133A3 (fr) 2003-04-03

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2002/002893 WO2003002133A2 (fr) 2001-06-29 2002-06-24 Stabilisation de chlorophylle

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AU (1) AU2002317275A1 (fr)
GB (1) GB0115982D0 (fr)
WO (1) WO2003002133A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017158427A1 (fr) * 2016-03-14 2017-09-21 Team Foods Colombia S.A. Composition et procédé pour le traitement de troubles cognitifs

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0711544A2 (fr) * 1994-10-18 1996-05-15 Kao Corporation Dentrifice
US6174514B1 (en) * 1999-04-12 2001-01-16 Fuisz Technologies Ltd. Breath Freshening chewing gum with encapsulations
US6287542B1 (en) * 1999-02-15 2001-09-11 Ilever Home & Personal Care Usa, A Division Of Conopco, Inc. Encapsulation
US6391323B1 (en) * 1997-11-26 2002-05-21 Andrea Carnevali Composition for the treatment of burns, sunburns, abrasions, ulcers and cutaneous irritation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0711544A2 (fr) * 1994-10-18 1996-05-15 Kao Corporation Dentrifice
US6391323B1 (en) * 1997-11-26 2002-05-21 Andrea Carnevali Composition for the treatment of burns, sunburns, abrasions, ulcers and cutaneous irritation
US6287542B1 (en) * 1999-02-15 2001-09-11 Ilever Home & Personal Care Usa, A Division Of Conopco, Inc. Encapsulation
US6174514B1 (en) * 1999-04-12 2001-01-16 Fuisz Technologies Ltd. Breath Freshening chewing gum with encapsulations

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BUECH, G. W. ET AL: "Degradation of chlorophyll in model preparations" DEUTSCHE LEBENSMITTEL-RUNDSCHAU (1998), 94(4), 109-112 , XP009003987 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017158427A1 (fr) * 2016-03-14 2017-09-21 Team Foods Colombia S.A. Composition et procédé pour le traitement de troubles cognitifs
US10869852B2 (en) 2016-03-14 2020-12-22 Team Foods Colombia S.A. Composition and method for treatment of neurodegenerative diseases

Also Published As

Publication number Publication date
GB0115982D0 (en) 2001-08-22
WO2003002133A3 (fr) 2003-04-03
AU2002317275A1 (en) 2003-03-03

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