Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing saccharide radical
Patent
1998-11-23
2000-04-11
Prats, Francisco
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing compound containing saccharide radical
435 74, 435 78, 435 96, 435 99, 435105, 536 41, 536124, C12P 1960, C12P 1944, C12P 1920, C12P 1914, C07G 300
Patent
active
060487127
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing a high .alpha.-monoglucosyl hesperidin content product, and more particularly to a process for producing a high .alpha.-monoglucosyl hesperidin content product, which comprises the steps of treating a solution containing .alpha.-glucosyl hesperidin and hesperidin to crystallize and separate .alpha.-monoglucosyl hesperidin, and collecting the resulting .alpha.-monoglucosyl hesperidin.
BACKGROUND ART
As shown in the following Formula [I], hesperidin is a compound where rutinose (L-rhamnosyl-(.alpha. 1.fwdarw.6)-glucose) binds to the hydroxyl group at the C-7 in hesperetin (3',5,7-trihydroxy-4'-metoxyflavanone) via the .beta.-linkage. ##STR1##
Hesperidin is present in immature fruit skins of citruses and used in pharmaceuticals, cosmetics, etc., as a vitamin P that has physiological functions such as capillary protestant, hemorrhagic prevention, blood-pressure control, etc. Hesperidin dissolves in aqueous alkaline solutions but not substantially in water and acids. Because only about one gram hesperidin dissolves in 50 1 water (about 0.002 w/v %) at ambient temperature, it easily causes cloudiness in the liquid parts of canned foods with only a slight amount thereof to deteriorate the products' value.
There have been proposed methods to prevent such cloudiness in liquids induced by hesperidin. For example, Japanese Laid-Open Publication No. 7,593/91 discloses a process for producing an enzyme-treated hesperidin with improved water-solubility, which comprises the steps of contacting hesperidin with a saccharide-transferring enzyme (an enzyme having .alpha.-glucosyl-transferring activity) in the presence of partial starch hydrolyzates (.alpha.-glucosyl saccharides) to form .alpha.-glucosyl hesperidin as shown by the following Formula [II]: ##STR2##
As shown in the above Formula [II], the .alpha.-glucosyl hesperidin is a compound where glucose(s) (Gn, n=1-20) successively bind(s) via the .alpha.-1,4 linkage to the C-4 of the glucose in hesperidin in Formula [I], or a mixture of such .alpha.-glucosyl hesperidins having different numbers of glucoses.
In the enzymatic reaction system, 40-80% hesperidin contained in a material solution is converted into .alpha.-glucosyl hesperidin by the enzyme treatment, while 20-60% hesperidin still remains intact free of reaction. The coexistence of .alpha.-glucosyl hesperidin increases the solubility of intact hesperidin in aqueous solutions, but a higher proportion of the intact hesperidin to the .alpha.-glucosyl hesperidin results in an insolubilization and crystallization of intact hesperidin within a relatively short period of time.
Although it can be proposed a method for adding gelatinizers such as carboxymethyl cellulose (CMC) to aqueous solutions containing hesperidin to increase the viscosity of the solutions as a means to prevent the crystallization of intact hesperidin, it could not be a general method because such an addition of the gelatinizers will not be acceptable in view of product image and should not be used in export products.
Also there exists a method for delaying the crystallization of intact hesperidin by crystallizing intact hesperidin and filtering the mixture to separate and remove the crystallized hesperidin in order to lower the proportion of the intact hesperidin to .alpha.-glucosyl hesperidin. Even with the method, intact hesperidin does crystallize after a relatively long period of time as a demerit, and therefore it could not be a substantial solution.
There still exists a method which comprises a step of collecting only a fraction of .alpha.-glucosyl hesperidin from aqueous solutions containing .alpha.-glucosyl hesperidin and intact hesperidin by a technique such as chromatographic fractionation to obtain a desired product for use. The method, however, results in a cost increase and is far from a beneficial method.
The present inventors continued studying to solve the problems in the prior art and found that an enzyme-treated hesperidin, which has extremely-increased wa
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Database WPI Section, Derwent Publications Ltd., London, Great Britain: Class D13. (1996).
Kometani, Takashi et al., "Synthesis of Hesperidin Glycosides by Cyclodextrin Glucanotransferase and Stabilization of the Natural Pigments", Nippon Shokuhin Kagaku Kogaku Kaishi, vol. 42, No. 5, pp. 376-382 (1995).
Miyake Toshio
Yumoto Takashi
Kabushiki Kaisha Hayashibara
Prats Francisco
Seibutsu Kagaku Kenkyujo
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