WO1999048982A1 - Colorant alimentaire et procede de production correspondant - Google Patents

Colorant alimentaire et procede de production correspondant Download PDF

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Publication number
WO1999048982A1
WO1999048982A1 PCT/AU1999/000193 AU9900193W WO9948982A1 WO 1999048982 A1 WO1999048982 A1 WO 1999048982A1 AU 9900193 W AU9900193 W AU 9900193W WO 9948982 A1 WO9948982 A1 WO 9948982A1
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WO
WIPO (PCT)
Prior art keywords
flavonoid compound
flavonoid
dough composition
compound
alkaline
Prior art date
Application number
PCT/AU1999/000193
Other languages
English (en)
Inventor
Daryl J. Mares
Youming Wang
Original Assignee
Quality Wheat Crc Limited
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 Quality Wheat Crc Limited filed Critical Quality Wheat Crc Limited
Priority to AU29161/99A priority Critical patent/AU2916199A/en
Publication of WO1999048982A1 publication Critical patent/WO1999048982A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10—Cereal-derived products
    • A23L7/109—Types of pasta, e.g. macaroni or noodles

Definitions

  • This invention relates to the field of food technology and, particularly, to the colouring of foods.
  • a method of producing Asian yellow alkaline noodles involving the addition of a colour enhancer selected from xanthophyll and flavonoid compound(s).
  • a method for extracting flavonoid compound(s) from plant tissue involving the addition of a colour enhancer selected from xanthophyll and flavonoid compound(s).
  • Asian yellow alkaline noodles are a very popular type of noodle accounting for approximately 30% of the world's total noodle production. Part of the reason for this popularity stems from the yellow colour of the noodles. Indeed, the intensity of the yellow colour is often perceived as an indicator of quality, although the actual preferred intensity of the yellow colour does vary in different markets.
  • Asian yellow alkaline noodles are prepared from wheat flour and an alkaline salt solution(s) such as sodium hydroxide or more usually, "Kansui", which is a mixture of potassium carbonate and sodium carbonate. It has been found that both the wheat flour and the alkaline salt solution(s) can influence the intensity of the yellow colour which develops in the noodles. For example, it is known that wheat flours prepared by different milling methods or from wheat of different genotype or which have been grown under different environments, will affect colour development in Asian yellow alkaline noodles.
  • an alkaline salt solution(s) such as sodium hydroxide or more usually, "Kansui"
  • Asian yellow alkaline noodles In order to satisfy the colour preferences of different markets and ensure consistent colouring, manufacturers of Asian yellow alkaline noodles presently add yellow food colouring(s) (e.g. tartrazine and riboflavin) during the production of the noodle dough. This, however, is generally regarded by manufacturers as being undesirable since the food colourings add considerably to the cost of the noodles and further, as a consequence of the necessity to make mention of the food colourings on product labelling, may also lead to reduced market appeal. Consequently, there is a need to identify and develop a method for producing Asian yellow alkaline noodles which allows control over the intensity of the yellow colour without addition of "artificial" yellow food colouring(s).
  • yellow food colouring(s) e.g. tartrazine and riboflavin
  • the present applicant has discovered that the yellow colour of Asian yellow alkaline noodles owes to the presence of xanthophyll (e.g. lutein and its esters) and flavonoid (e.g. Flavone-C-diglycosides) compounds in wheat flour.
  • xanthophyll e.g. lutein and its esters
  • flavonoid e.g. Flavone-C-diglycosides
  • the present invention provides a method for the production of Asian yellow alkaline noodles, said method comprising preparing a dough composition from at least wheat flour, an alkaline solution and a colour enhancer selected from one or more xanthophyll and/or flavonoid compound(s), and thereafter forming noodles from the dough composition.
  • the colour enhancer be selected from xanthophyll and/or flavonoid compound (s) that are naturally present in wheat grain
  • xanthophyll and/or flavonoid compounds as might be present in grain from other cereal plants (e.g. barley and linseed) or which might be produced synthetically, may also be suitable for producing or enhancing yellow colour in Asian yellow alkaline noodles.
  • the colour enhancer may be used in combination with one or more traditional "artificial" yellow food colouring(s) such as tartrazine, riboflavin, annatto and gardenia yellow.
  • the colour enhancer is selected from flavonoid compound(s) of formula I:
  • R 1 and R 3 are independently selected from H, OH, lower alkyl, lower alcohol and lower alkoxy
  • R 2 and R 4 are independently selected from H, OH, lower, alkyl, lower alcohol, lower alkoxy and glycoside
  • X and Y are independently selected from H, OH, lower alkyl, lower alcohol, lower alkoxy and groups of formula II:
  • X and Y are not both groups of formula II and where R 5 , R 6 , R 7 and R 8 are independently selected from H, OH, lower alkyl, lower alcohol and lower alkoxy.
  • lower as used in “lower alkyl”, “lower alcohol” and “lower alkoxy” is intended to mean a group having 1 to 6 carbon atom(s).
  • Suitable “lower alcohol” groups may be methanol, ethanol, propanol, isopropanol, butanol, isobutanol and the like.
  • the preferred lower alcohol group is methanol.
  • Suitable "lower alkyl” groups may be straight or branched such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl or the like. However, the preferred lower alkyl group is methyl.
  • Suitable "lower alkoxy” groups may be methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy and the like. However, the preferred lower alkoxy group is methoxy.
  • Especially preferred compounds of formula (I) are those where one or both of R 2 and R 4 are glycosides (e.g. O-glycosides or, more preferably, C- glycosides).
  • the colour enhancer is selected from the group consisting of 5,7,4'-trihydroxyflavone (Apigenin), 5,7-dihydroxyflavone, 3, 7, 3', 4'- tetrahydroxyflavone, 7,4'-dihydroxyisoflavone, 5,7,3'-trihydroxy-4'- methoxyflavone, 3,4',5,7-tetrahydroxyflavone, 5,7,3',4'-tetrahydroxyflavone, 3,5,7,2',4'-pentahydiOxyflavone, 3,5,7,3',4',5'-hexahydroxyflavone and 3,5,7,3',4'-pentahydroxyflavone, and monoglycoside and diglycoside forms thereof.
  • Apigenin 5,7-dihydroxyflavone
  • 3, 7, 3', 4'- tetrahydroxyflavone 7,4'-dihydroxyisoflavone
  • the colour enhancer be added to provide a concentration in the range of 1 to 50 x 10 "4 % (i.e. 0.0001 to 0.005%), more preferably 5 to 25 x 10 ⁇ 4 % (i.e. 0.0005 to
  • the colour enhancer be added to provide a concentration in the range of 1 to 75 x 10 "3 % (i.e. 0.001 to 0.075%), more preferably 5 to 50 x 10 "3 % (i.e. 0.005 to 0.05%), by weight of the dough composition.
  • the dough composition prepared in the method of the first aspect of the present invention preferably comprises, by weight %; 60 to 65 % wheat flour,
  • the dough composition has a pH > 9, more preferably a pH in the range of 10 to 12, and the alkaline solution used in the preparation of the dough composition is preferably selected from alkaline salt solutions routinely used in the art. More preferably, the alkaline solution is a 1 to 3 %
  • the dough composition may further comprise additives as routinely used in the art.
  • the dough composition may further include gluten-softening agents (e.g. L-cysteine and sodium metabisulfite) or, as mentioned above, one or more of the traditional "artificial" yellow food colouring(s) (e.g. tartrazine and riboflavin).
  • the dough composition may be prepared by any of the methods routine to the art. Since xanthophyll compounds typically show a low level of solubility in water, the xanthophyll compound(s) are preferably added in solid form or in an organic solvent carrier such as methanol.
  • the wheat flavonoid compound(s) are predominantly in the form of of flavonoid glycosides which show a high level of solubility in water and in aqueous solutions containing methanol up to 60% (v/v).
  • the flavonoid compound(s) are therefore preferably added as a water solution or, more preferably, by dissolving a solid preparation into the water that is used to produce the dough composition (i.e. prior to the addition of the wheat flour).
  • Non- glycosylated flavonoids are generally insoluble in water and are therefore preferably added in solid form or in an organic carrier such as methanol.
  • the alkaline solution is also preferably added by dissolving the solution (or salts) into the water used to produce the dough composition.
  • the preparation of dough for Asian yellow alkaline noodles involves mixing the components, compressing the mixture into a dough piece, followed by passage through a plurality of sheeting rolls as required.
  • the formation of noodles from the dough composition may be in accordance with any of the methods routine to the art. Typically, this will involve cutting the noodles from extruded sheets or, alternatively, by extrusion directly into noodles.
  • the present invention provides Asian yellow alkaline noodles produced in accordance with the method of the first aspect of the present invention.
  • flavonoid compounds have not been previously used to colour foods or other products.
  • the present invention provides a method for colouring a solid or liquid material, said method comprising adding to said material or a component therof, one or more flavonoid compound(s).
  • the method may further comprise adding an alkaline solution (or alkaline salts) to produce a pH > 9 and preferably within the range of 10 to 12.
  • the material to be coloured may be a food such as baked or other flour- based products, or a beverage such as a soft drink.
  • the material may also be selected from products such as wool, paper and fibreboard, and plastics.
  • the applicant has further identified and developed a method for extracting flavonoid compound(s) from plant tissue. Since this method does not involve the use of organic solvents, the extracted flavonoid compound(s) may be partic ilarly suitable for the colouring of foods.
  • the present invention provides a method for extracting flavonoid compound(s) from suitable plant tissue, said method comprising extracting said flavonoid compound(s) from said plant tissue with an aqtieous solvent, and thereafter substantially removing non-flavonoid compounds and impurities from the aqueous solvent extract.
  • the plant tissue is ground or otherwise reduced to a particle form to thereby present a greater surface area to the aqueous extraction solvent.
  • the extraction step may comprise one or more extractions of the plant tissue with an aqueous solvent.
  • the extraction(s) is/are conducted at room temperature (e.g. 20-27°C) for 2 to 24 hours, more preferably 10 to 20 hours.
  • the aqueous solvent may be selected from water, hydroxylamine, water/alcohol mixtures containing hydroxylamine, sodium carbonate and dilute sodium hydroxide.
  • the aqueous solvent is hydroxylamine, particularly at concentrations of 0.05 to 0.2 molar or dilute sodium hydroxide (i.e. water adjusted to pH 11 with sodium hydroxide).
  • the step of substantially removing non-flavonoid compounds and impurities from the aqueous solvent extract preferably substantially removes proteinaceous material and polysaccharides (e.g. starches and arabinoxylans).
  • Proteinaceous materials may be readily removed by acid precipitation (e.g by treatment with acetic or other suitable acid).
  • Polysaccharides may be readily removed by precipitation with a suitable alcohol (e.g. methanol).
  • the flavonoid compound(s) may optionally be recovered from the aqueous product (i.e. the product remaining after removal of non-flavonoid compounds and impurities).
  • the aqueous product containing the flavonoid compound(s) may, however, be directly used for colouring applications such as the production of Asian yellow alkaline noodles.
  • the flavonoid compound(s) extracted by the method of the fourth aspect of the present invention is/are prefererably selected from Flavone-C- diglycosides and, especially from Apigenin-C-diglycosides.
  • the plant tissue from which the flavonoid compound (s) is/are extracted is preferably selected from grains of cereal plants. More preferably, the plant tissue is wheat grain. Most preferably, the plant tissue is wheat germ tissue, which has been found by the applicant's to provide an enriched source of flavonoid compound(s). This finding is particularly important since it provides a new use for wheat germ, which is a by-product of flour milling and, at present, is primarily used as an animal feed.
  • the terms "comprise”, “comprises” and “comprising” as used throughout the specification are intended to refer to the inclusion of a stated component, feature or step or group of components, features or steps with or without the inclusion of a further component, feature or step or group of components, features or steps.
  • Figure 1 shows RP-HPLC traces of hydroxylamine (NH 2 OH) extracts of wheat flour. Flavonoid and phenolic compounds were detected by their absorbance at 340nm (upper trace) whilst the compounds which turned yellow in the presence of alkali (NaOH) were detected by their absorbance at 463nm following addition of alkali to the column effluent.
  • the peaks designated 9 and 11 contained apigenin-C-diglycosides and appear to make the largest contribution to the yellow colour of alkaline noodles.
  • Figure 2 shows the absorbance profiles (180 - 600 nm) for purified apigenin-C-diglycosides (peak 9 from Figure 1) measured in the absence and presence of alkali (NaOH). The observed shift in the major absorbance peak reflects the yellow colour development that occurs in the presence of alkali.
  • Figure 3 provides the results of reflectance tests conducted on noodle sheets prepared from wheat flour and salt (NaCl) solution or alkali (NaOH) solution (controls), and sheets prepared from wheat flour, which has been extracted with hydroxylamine (NH 2 OH), and alkali (NaOH).
  • the results show that noodle sheets prepared from unextracted wheat flour and alkali solution caused considerably less reflectance at wavelengths of 400, 420, 440 and 460 nm (i.e due to the greatest yellow colour development), whereas noodle sheets prepared from extracted wheat flour and alkali caused levels of reflectance similar to that observed with the noodle sheets prepared from unextracted wheat flour and salt.
  • wheat flour or whole meal, bran, germ
  • 0.1M hydroxylamine, pH 7, (l:10,w/v) for 12 hours at room temperature.
  • the mixture was allowed to stand and the residual flour settle before the extract was decanted.
  • the remaining residue was extracted a second time with hydroxylamine (l:5,w/v) for 6 hours.
  • the extracts were combined and centrifuged at 3500 r.p.m. for 20 min., adjusted to pH 5.2 with acetic acid and left at 4°C overnight to allow protein to precipitate.
  • the precipitate was removed by centrifugation and the supernatant concentrated to a volume of approximately 20ml with a rotary evaporator under reduced pressure at 40°C.
  • the column effluent was monitored at 340nm. In order to identify the specific constituents which turn yellow in the presence of alkali, the column effluent was first reacted with 3% sodium hydroxide and then monitored at 436nm
  • Apigenin-C-diglycosides have been identified in a range of plant tissues and in extracts of wheat bran, but they have not previously been identified as the compounds responsible for the alkaline-induced component of the yellow colour of alkaline noodles (responsible for approximately two thirds of the total yellow colour and additive with the yellow colour contributed by xanthophylls).
  • Germ tissue was dissected from wheat grains, then the remaining portion separated into endosperm and bran using laboratory flour mill. The dissected germ was ground to a fine powder in a burr mill. Samples of each grain fraction were extracted with hydroxylamine as described above and then analyzed by reverse phase HPLC. The major flavonoids responsible for the alkali-induced yellow colour were located solely in the germ fraction. Other flavonoids/phenolics located in the bran layers also turned yellow in the presence of alkali, however, these compounds were largely separated from the flour during milling and made only a very minor contribution to noodle colour.
  • the present invention permits manufacturers of Asian yellow alkaline noodles to control the intensity of the yellow colour through the use of natural colour enhancers without recourse to "artificial” (i.e. non-wheat) food colourings and most likely without adversely affecting product appearance, taste or texture. 10

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  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Noodles (AREA)

Abstract

L'invention se rapporte à un procédé de production de nouilles asiatiques alcalines, de couleur jaune. Ce procédé consiste à ajouter un renforçateur de couleur sélectionné parmi la xanthophylle et un(des) composé(s) flavonoïde(s). L'invention se rapporte également à un procédé consistant à extraire un(des) composé(s) flavonoïde(s) d'un tissu végétal ainsi qu'à l'utilisation d'un(des) composé(s) flavonoïde(s) pour colorer des aliments, de la laine, du papier, des panneaux de fibres et des plastiques.
PCT/AU1999/000193 1998-03-23 1999-03-19 Colorant alimentaire et procede de production correspondant WO1999048982A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29161/99A AU2916199A (en) 1998-03-23 1999-03-19 Food colouring and method for producing same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPP2545A AUPP254598A0 (en) 1998-03-23 1998-03-23 Food colouring and method for producing same
AUPP2545 1998-03-23

Publications (1)

Publication Number Publication Date
WO1999048982A1 true WO1999048982A1 (fr) 1999-09-30

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AU (1) AUPP254598A0 (fr)
WO (1) WO1999048982A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2813503A1 (fr) * 2000-09-05 2002-03-08 Nestle Sa Nouilles et pates alimentaires colorees, et procede pour colorer la pate utilisee pour leur preparation
FR2842817A1 (fr) * 2002-07-26 2004-01-30 Univ Pasteur Utilisation de derives de composes flavylium pour leur fixation sur des substrats solides, compositions de fixation utilisees et substrats obtenus
EP1764003A1 (fr) * 2005-09-15 2007-03-21 The Quaker Oats Company Aliment coloré prêt-à-consommer, à base d'ingrédients naturels, de couleur stable, composition alimentaire et méthode
EP2368442A2 (fr) 2005-07-27 2011-09-28 Symrise AG Utilisation d'hespérétine pour améliorer le goût sucré
WO2015187120A1 (fr) * 2014-06-02 2015-12-10 Thomas Thomas Nadackal Eau améliorée phytochimique

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0612814A1 (fr) * 1993-02-25 1994-08-31 Ensuiko Sugar Refining Company, Limited Composition colorante contenant de la quercétine
DE4325532A1 (de) * 1993-07-29 1995-02-02 Schwabe Willmar Präparate aus Crataegus-Arten, Arzneimittel und ihre Verwendung zur Verhinderung des plötzlichen Herztodes sowie von reperfusionsbedingten cardiovaskulären Schädigungen
WO1997014319A1 (fr) * 1995-10-20 1997-04-24 Hauser Chemical Research, Inc. Aliments et boissons contenant des anthocyanines stabilisees par des extraits vegetaux
DE19621966A1 (de) * 1996-05-31 1997-12-04 Basf Ag Verwendung von natürlichen oder naturidentischen synthetischen Farbstoffen zur vorübergehenden Markierung oder Einfärbung von festen und flüssigen Materialien

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0612814A1 (fr) * 1993-02-25 1994-08-31 Ensuiko Sugar Refining Company, Limited Composition colorante contenant de la quercétine
DE4325532A1 (de) * 1993-07-29 1995-02-02 Schwabe Willmar Präparate aus Crataegus-Arten, Arzneimittel und ihre Verwendung zur Verhinderung des plötzlichen Herztodes sowie von reperfusionsbedingten cardiovaskulären Schädigungen
WO1997014319A1 (fr) * 1995-10-20 1997-04-24 Hauser Chemical Research, Inc. Aliments et boissons contenant des anthocyanines stabilisees par des extraits vegetaux
DE19621966A1 (de) * 1996-05-31 1997-12-04 Basf Ag Verwendung von natürlichen oder naturidentischen synthetischen Farbstoffen zur vorübergehenden Markierung oder Einfärbung von festen und flüssigen Materialien

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ASEAN FOOD JOURNAL, 1994, 9(4), LORENZ K.J., MARTIN D.J., STEWART B.G., "Chinese-Style Noodles Made from Buhler Mill Fractions of Australian Wheats", pages 156-160. *
DATABASE WPIDS, DERWENT PUBLICATIONS LTD., LONDON, GB, AN 93-364259(46), week 9346, "Health Food and Drink - Contg. Extract of Hawthorn Leaves"; & JP 05268920 A (TOYO RIKEN KK) 19 October 1993. *
DATABASE WPIDS, DERWENT PUBLICATIONS LTD., LONDON, GB, AN 94-156650(19), week 9419, "Flavonoid Glycoside Extracted from Eucalyptus - Useful as Anti-Oxidants"; & JP 06100584 A (JUMOKU CHUSHUTSU SEIBUN RIYO GIJUTSU KEN) 12 April 1994. *
HENDERSON'S DICTIONARY OF BIOLOGICAL TERMS, 10th Edition, HENDERSON I.F., LONGMAN GROUP UK LIMITED, 1989, page 187, "Flavone", "Flavonoid" and "Flavonol" and page 591, "Xanthophyll". *
PATENT ABSTRACTS OF JAPAN; & JP 06261700 A (TOYO SEITO KK) 20 September 1994. *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2813503A1 (fr) * 2000-09-05 2002-03-08 Nestle Sa Nouilles et pates alimentaires colorees, et procede pour colorer la pate utilisee pour leur preparation
SG90749A1 (en) * 2000-09-05 2002-08-20 Nestle Sa Coloured noodles
FR2842817A1 (fr) * 2002-07-26 2004-01-30 Univ Pasteur Utilisation de derives de composes flavylium pour leur fixation sur des substrats solides, compositions de fixation utilisees et substrats obtenus
WO2004013407A2 (fr) * 2002-07-26 2004-02-12 Universite Louis Pasteur Utilisation de derives de composes flavylium pour leur fixation sur des substrats solides, compositions de fixation utilisees et substrats obtenus
WO2004013407A3 (fr) * 2002-07-26 2004-04-08 Univ Pasteur Utilisation de derives de composes flavylium pour leur fixation sur des substrats solides, compositions de fixation utilisees et substrats obtenus
EP2368442A2 (fr) 2005-07-27 2011-09-28 Symrise AG Utilisation d'hespérétine pour améliorer le goût sucré
EP1764003A1 (fr) * 2005-09-15 2007-03-21 The Quaker Oats Company Aliment coloré prêt-à-consommer, à base d'ingrédients naturels, de couleur stable, composition alimentaire et méthode
WO2015187120A1 (fr) * 2014-06-02 2015-12-10 Thomas Thomas Nadackal Eau améliorée phytochimique

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