JPH10101624A - Production of polyamine - Google Patents

Production of polyamine

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Publication number
JPH10101624A
JPH10101624A JP29434096A JP29434096A JPH10101624A JP H10101624 A JPH10101624 A JP H10101624A JP 29434096 A JP29434096 A JP 29434096A JP 29434096 A JP29434096 A JP 29434096A JP H10101624 A JPH10101624 A JP H10101624A
Authority
JP
Japan
Prior art keywords
polyamine
nmol
tea
resin
supernatant
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
JP29434096A
Other languages
Japanese (ja)
Inventor
Juzo Udaka
重三 鵜高
Akiko Okamoto
章子 岡本
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to JP29434096A priority Critical patent/JPH10101624A/en
Publication of JPH10101624A publication Critical patent/JPH10101624A/en
Pending legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PROBLEM TO BE SOLVED: To obtain a polyamine in a good efficiency and yield, having a physiological activity, and useful as a medicine, a cosmetic material, a food, etc., by extracting teas under an acidic condition. SOLUTION: This method for producing a polyamine is e.g. to add 25ml of 5% trichloroacetic acid to 5g green tea, agitate vigorously with a homogenizer, then keep agitating mildly for one hour, separate the obtained mixture to a supernatant and a precipitate with a centrifugal separator, pass the obtained supernatant through a week cation exchanging resin, then wash the resin sufficiently with water, and elute the polyamine adsorbed to the resin with 6N HCl for obtaining the polyamine from the tea.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【産業上の利用分野】本発明は、ポリアミンの製造法に
関する。
The present invention relates to a method for producing a polyamine.

【0002】[0002]

【従来の技術】ポリアミン(即ち二分子のアミンを含む
プトレスシン、三分子のアミンを含むスペルミジン及び
四分子のアミンを含むスペルミン)は、その発見が核酸
のそれより約200年も古いが、その生理活性がやや明
らかになったのは、最近のことである。そして、その生
理活性としては、現在種々検討されているが、例えば、
生物に対する多彩な作用特に細胞に必須な成分としての
作用(例えば、細胞増殖、細胞の分化、環境適応、蛋白
及び核酸の合成、細胞膜の安定化、神経伝達など)、並
びに細胞内の抗酸化性及び化学的な抗酸化性及び抗メイ
ラード反応性などがあげられている。さらに、癌の診断
にも、有効であるとされている。(例えば、ポリアミン
全般については五十嵐一衛「神秘の生命物質−ポリアミ
ン]共立出版、1993年、抗酸化性については、E.
Lφvaas「Antioxidative Effe
cts of Polyamines」J.A.O.
C.S.68、353−358、1991)。これらポ
リアミンは、広く生物の組織などに存在する。
BACKGROUND OF THE INVENTION Polyamines (i.e., putrescine containing two molecules of amine, spermidine containing three molecules of amine, and spermine containing four molecules of amine) are about 200 years older than those of nucleic acids, but their physiology. It is only recently that activity has become somewhat apparent. And as its physiological activity, various studies are currently being conducted.
Various effects on living organisms, especially as an essential component of cells (eg, cell proliferation, cell differentiation, environmental adaptation, synthesis of proteins and nucleic acids, stabilization of cell membranes, neurotransmission, etc.), and intracellular antioxidant properties And chemical antioxidant and anti-Maillard reactivity. Furthermore, it is said to be effective also in the diagnosis of cancer. (For example, for polyamines in general, Kazue Igarashi, "Mysterious Biological Substances-Polyamines", Kyoritsu Shuppan, 1993;
Lφvaas "Antioxidative Effe
cts of Polyamines " A. O.
C. S. 68, 353-358, 1991). These polyamines are widely found in biological tissues and the like.

【0003】[0003]

【発明の概要】本発明は、多彩な生理活性作用を有する
ポリアミンを得る方法に関する。即ち、本発明は、茶類
から酸性条件下でポリアミンを抽出するポリアミンの製
造法に関する。本発明では、原料として茶類を使用す
る。本発明で使用される茶類は、Camellia属の
亜熱帯性の植物である茶樹の葉及び/又は茎からとれる
ものであって、生のものでも加工されたものでも使用で
きる。茶樹は、中国種C.sinensis var
sinensis.及びアッサム種C.sin. va
rassamicaの二つの変種に大別され、さらに両
者の中間種であるアッサム雑種を含む。そして、これら
の葉及び/又は茎は、加工されて、茶類例えば緑茶(日
本茶)、ウーロン茶、紅茶などになる。本発明では、こ
れら茶類を使用することができるが、緑茶が好ましい。
また、茶類そのものでも、又はそれから熱水抽出後に残
った、いわゆる茶殻でも使用することができる。さら
に、茶類の形状としては、それを粉末化したものでも使
用できる。
SUMMARY OF THE INVENTION The present invention relates to a method for obtaining polyamines having various bioactive actions. That is, the present invention relates to a method for producing a polyamine by extracting a polyamine from teas under acidic conditions. In the present invention, tea is used as a raw material. The teas used in the present invention can be obtained from leaves and / or stems of tea plants, which are subtropical plants of the genus Camellia, and can be either raw or processed. The tea plant is Chinese C. sinensis var
sinensis. And Assam species C.I. sin. va
rassamica, which is broadly classified into two varieties, and further includes an Assam hybrid which is an intermediate between the two varieties. These leaves and / or stems are processed into teas such as green tea (Japanese tea), oolong tea, and black tea. In the present invention, these teas can be used, but green tea is preferred.
In addition, teas themselves or so-called tea husks remaining after extraction with hot water can be used. Further, as the shape of tea, powdered tea can also be used.

【0004】ポリアミンは、前記のごとく、生物体に広
く存在しているが、茶類には高い濃度でポリアミンに含
まれる3種類の化合物が平均して存在している。例え
ば、緑茶では、プトレスシン(A)が520ナノモル/
g、スペルミジン(B)が885ナノモル/gそしてス
ペルミン(C)が552ナノモル/g含まれている。こ
れに対して、同じ植物である米ではAが<10ナノモル
/g、Bが27ナノモル/g、Cが<20ナノモル/g
であり、小麦粉ではAが17ナノモル/g、Bが66ナ
ノモル/g、Cが26ナノモル/gであり、また大豆で
は、Aが200−500ナノモル/g、Bが400−8
00ナノモル、Cが40−200ナノモル/gであり、
椎茸ではAが29ナノモル/g、Bが893ナノモル/
g、Cは存在しない。さらに、オレンジでは、Aが89
0−1331ナノモル/gと多いが、Bは18−26ナ
ノモル/g、Cは<5ナノモル/gと少ない。動物につ
いては、牛肉では、Aが<5ナノモル/g、Bが18ナ
ノモル/g、Cが136ナノモル/gであり、豚肉で
は、Aが13ナノモル/g、Bが18ナノモル/g、C
が136ナノモル/gであり、鶏肉では、Aが<5ナノ
モル/g、Bが20ナノモル/g、Cが308ナノモル
/gであり、マグロ肉では、Aが存在せず、Bが30ナ
ノモル/g、Cが34ナノモル/gである。鶏卵では、
A、B及びCの何れも存在しない。このデータから分か
るように、茶類は、ポリアミンを構成する3種の化合物
の何れも高濃度で含んでおり、従ってそれから抽出を行
うと、得られるポリアミンの収量が高いことになる。こ
の理由から、茶類からポリアミンを抽出するのは、工業
的に優れていることになる。特に、従来、多量の廃棄物
として出ている茶殻を利用できることも、環境の点から
有利であるということができる。
[0004] As described above, polyamines are widely present in living organisms, but in teas, three types of compounds contained in polyamines at high concentrations are present on average. For example, in green tea, putrescine (A) contains 520 nmol /
g, spermidine (B) at 885 nmol / g and spermine (C) at 552 nmol / g. In contrast, in the same plant rice, A <10 nmol / g, B 27 nmol / g, and C <20 nmol / g.
In the flour, A is 17 nmol / g, B is 66 nmol / g, and C is 26 nmol / g. In soybean, A is 200-500 nmol / g, and B is 400-8 nmol / g.
00 nmol, C is 40-200 nmol / g,
In Shiitake mushrooms, A was 29 nmol / g and B was 893 nmol / g.
g and C do not exist. Furthermore, in orange, A is 89
Although it is as large as 0-1331 nmol / g, B is as small as 18-26 nmol / g and C is as small as <5 nmol / g. Regarding animals, in beef, A is <5 nmol / g, B is 18 nmol / g, and C is 136 nmol / g. In pork, A is 13 nmol / g, B is 18 nmol / g, C is 18 nmol / g.
Is 136 nmol / g, in chicken, A is <5 nmol / g, B is 20 nmol / g, and C is 308 nmol / g. In tuna meat, A is not present and B is 30 nmol / g. g and C are 34 nmol / g. In chicken eggs,
None of A, B and C are present. As can be seen from this data, tea contains a high concentration of any of the three compounds that make up the polyamine, so that extraction from it results in a high yield of the resulting polyamine. For this reason, extracting polyamines from teas is industrially superior. In particular, it can be said that the ability to use tea husks that are conventionally produced as a large amount of waste is also advantageous from an environmental point of view.

【0005】本発明では、この茶類から酸性条付下でポ
リアミンを抽出する。この抽出にあたっては、従来の方
法を使用することができる。例えば、その一例として、
有機溶媒中で茶類を抽出し、抽出物を陽イオン交換樹脂
に通して樹脂にポリアミンを吸着させる。樹脂に吸着し
たポリアミンを酸例えば塩酸により溶出させる。得られ
た溶離液を、高速液体クロマトグラフィーにより精製す
る。別法として、茶類を、塩酸のような無機酸又は酢酸
のような有機酸を含む酸性溶液によりポリアミンを抽出
させ、得られたポリアミンを含む溶液から水分を加熱な
どの手段により除き、アルカリにより中和して、ポリア
ミンを高濃度に含む液を得るか、又はこの液を蒸発乾固
させて固形物を得る。この方法は、茶殻から食品用途の
ような低純度のポリアミンを得るのに好適である。これ
らの方法以外にも、任意の方法を行うことができる。本
発明では、ポリアミンを高い収率で得ることができる。
得られたポリアミンは、上記のような生理活性を有する
ため、天然物であるという特質を活かし、医薬品、化粧
品、食品などの用途に使用することができる。
In the present invention, a polyamine is extracted from this tea under acidic conditions. In this extraction, a conventional method can be used. For example, as an example,
Tea is extracted in an organic solvent, and the extract is passed through a cation exchange resin to adsorb the polyamine to the resin. The polyamine adsorbed on the resin is eluted with an acid such as hydrochloric acid. The obtained eluate is purified by high performance liquid chromatography. Alternatively, teas are extracted with a polyamine by an acidic solution containing an inorganic acid such as hydrochloric acid or an organic acid such as acetic acid, and water is removed from the resulting solution containing the polyamine by means of heating or the like, and the tea is treated with an alkali. Neutralize to obtain a liquid containing a high concentration of polyamine, or evaporate the liquid to dryness to obtain a solid. This method is suitable for obtaining low-purity polyamines such as food applications from tea leaves. Any method other than these methods can be used. In the present invention, a polyamine can be obtained in a high yield.
Since the obtained polyamine has the above-mentioned physiological activities, it can be used for applications such as pharmaceuticals, cosmetics, and foods, taking advantage of the characteristic of being a natural product.

【0006】[0006]

【実施例】【Example】

実施例 1 緑茶5gに、25mLの5%トリクロロ酢酸を加え、ホ
モゲナイザーで烈しく撹拌した後、さらに1時間緩やか
に撹拌を続けた。得られた混合物を、遠心分離器(回転
数1.5万回/1分間、15分)により上清液と沈殿と
に分けた。得られた上清液100μLを、Muroma
c CR−70カラム(弱陽イオン交換樹脂、2mM酢
酸緩衝液pH5.0で平衡化)に通した後、水で十分に
洗い、6N HClにより樹脂に吸着しているポリアミ
ンを溶離させた。その溶媒液を、エバポレータにより蒸
発乾固してから、水400μLを加えて固形物を溶解し
た。その40μLを高速液体クロマトグラフィー(カラ
ム:トーソー製、TSK−ケル Aminopak、溶
離液:6%エタノール、2.4M NaClを含む0.
2M酢酸緩衝液pH5.6、65℃)にかけ、精製した
ポリアミンを分取した。得られたポリアミンは、緑茶1
gあたり46μgのプトレシン、128μgのスペルミ
ジン、112μgのスペルミンを含んだ。
Example 1 To 5 g of green tea, 25 mL of 5% trichloroacetic acid was added and stirred vigorously with a homogenizer, followed by gentle stirring for another hour. The obtained mixture was separated into a supernatant and a precipitate by a centrifuge (15,000 rotations / 1 minute, 15 minutes). 100 μL of the obtained supernatant was added to Muroma
c After passing through a CR-70 column (weak cation exchange resin, equilibrated with 2 mM acetate buffer pH 5.0), the plate was washed thoroughly with water, and the polyamine adsorbed on the resin was eluted with 6N HCl. The solvent was evaporated to dryness using an evaporator, and 400 μL of water was added to dissolve the solid. 40 μL of the mixture was subjected to high performance liquid chromatography (column: Tosoh, TSK-Kel Aminopak, eluent: 6% ethanol, 0.2M NaCl containing 2.4 M NaCl).
2M acetate buffer (pH 5.6, 65 ° C.) to separate the purified polyamine. The obtained polyamine is green tea 1
Each g contained 46 μg putrescine, 128 μg spermidine, 112 μg spermine.

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】茶類から酸性条件下でポリアミンを抽出す
るポリアミンの製造法。
1. A method for producing a polyamine, comprising extracting a polyamine from teas under acidic conditions.
JP29434096A 1996-10-01 1996-10-01 Production of polyamine Pending JPH10101624A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP29434096A JPH10101624A (en) 1996-10-01 1996-10-01 Production of polyamine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP29434096A JPH10101624A (en) 1996-10-01 1996-10-01 Production of polyamine

Publications (1)

Publication Number Publication Date
JPH10101624A true JPH10101624A (en) 1998-04-21

Family

ID=17806443

Family Applications (1)

Application Number Title Priority Date Filing Date
JP29434096A Pending JPH10101624A (en) 1996-10-01 1996-10-01 Production of polyamine

Country Status (1)

Country Link
JP (1) JPH10101624A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248341B1 (en) 2000-01-14 2001-06-19 Color Access, Inc. Method of treating topical angiogenesis-related disorders
JP2007291027A (en) * 2006-04-26 2007-11-08 Toyobo Co Ltd Method for preparing polyamine composition from plant
WO2007148737A1 (en) * 2006-06-22 2007-12-27 Toyo Boseki Kabushiki Kaisha Method of preparing plant extract, plant extract and use of the same
WO2007148739A1 (en) * 2006-06-22 2007-12-27 Toyo Boseki Kabushiki Kaisha Cell activator, anti-aging agent and extracellular matrix production promoter derived from plant
JP2008239547A (en) * 2007-03-27 2008-10-09 Toyobo Co Ltd Plant-derived activator and extracellular matrix production promoter
JP2010263816A (en) * 2009-05-13 2010-11-25 Lotte Co Ltd Method for producing food and drink containing polyamine
JP2011239786A (en) * 2011-08-09 2011-12-01 Toyobo Co Ltd Method for preparing polyamine composition from plant
JP2012006954A (en) * 2011-08-09 2012-01-12 Toyobo Co Ltd Method for preparing polyamine composition from plant
JP2012046544A (en) * 2011-11-29 2012-03-08 Toyobo Co Ltd Activation agent and extracellular matrix production promoter of plant origin
JP2012254965A (en) * 2011-05-13 2012-12-27 Toyobo Co Ltd Method for producing polyamine composition from plant
US9078455B2 (en) 2010-03-25 2015-07-14 Conopco, Inc. Process for manufacturing tea products
KR20190120779A (en) 2017-03-17 2019-10-24 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 Polyamine high yeast and food and drink composition comprising the same
KR20240010582A (en) 2022-07-13 2024-01-24 이해익 Novel strains of Bacillus coagulans producing high amount of polyamine

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6248341B1 (en) 2000-01-14 2001-06-19 Color Access, Inc. Method of treating topical angiogenesis-related disorders
JP2007291027A (en) * 2006-04-26 2007-11-08 Toyobo Co Ltd Method for preparing polyamine composition from plant
JPWO2007148739A1 (en) * 2006-06-22 2009-11-19 東洋紡績株式会社 Plant-derived cell activator, anti-aging agent, and extracellular matrix production promoter
WO2007148739A1 (en) * 2006-06-22 2007-12-27 Toyo Boseki Kabushiki Kaisha Cell activator, anti-aging agent and extracellular matrix production promoter derived from plant
JPWO2007148737A1 (en) * 2006-06-22 2009-11-19 東洋紡績株式会社 Method for preparing plant extract, plant extract and use thereof
WO2007148737A1 (en) * 2006-06-22 2007-12-27 Toyo Boseki Kabushiki Kaisha Method of preparing plant extract, plant extract and use of the same
JP2008239547A (en) * 2007-03-27 2008-10-09 Toyobo Co Ltd Plant-derived activator and extracellular matrix production promoter
JP2010263816A (en) * 2009-05-13 2010-11-25 Lotte Co Ltd Method for producing food and drink containing polyamine
US9078455B2 (en) 2010-03-25 2015-07-14 Conopco, Inc. Process for manufacturing tea products
JP2012254965A (en) * 2011-05-13 2012-12-27 Toyobo Co Ltd Method for producing polyamine composition from plant
JP2011239786A (en) * 2011-08-09 2011-12-01 Toyobo Co Ltd Method for preparing polyamine composition from plant
JP2012006954A (en) * 2011-08-09 2012-01-12 Toyobo Co Ltd Method for preparing polyamine composition from plant
JP2012046544A (en) * 2011-11-29 2012-03-08 Toyobo Co Ltd Activation agent and extracellular matrix production promoter of plant origin
KR20190120779A (en) 2017-03-17 2019-10-24 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 Polyamine high yeast and food and drink composition comprising the same
KR20240010582A (en) 2022-07-13 2024-01-24 이해익 Novel strains of Bacillus coagulans producing high amount of polyamine

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