JPH07268322A - Antioxidation agent - Google Patents
Antioxidation agentInfo
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- JPH07268322A JPH07268322A JP7471594A JP7471594A JPH07268322A JP H07268322 A JPH07268322 A JP H07268322A JP 7471594 A JP7471594 A JP 7471594A JP 7471594 A JP7471594 A JP 7471594A JP H07268322 A JPH07268322 A JP H07268322A
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- compound
- formula
- antioxidant
- compounds
- antioxidation
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- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は食品、飼料、化粧料、医
薬品またはこれらの原料等の酸化による品質低下を防ぐ
のに有用な抗酸化活性を有する、天然物由来の抗酸化剤
に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antioxidant derived from a natural product, which has an antioxidant activity useful for preventing deterioration of quality of foods, feeds, cosmetics, pharmaceuticals or raw materials thereof due to oxidation.
【０００２】[0002]
【従来の技術】従来、抗酸化剤としては、例えば、ＢＨ
Ａ（ブチルヒドロキシアニソール）、ＢＨＴ（ブチルヒ
ドロキシトルエン）や、エリソルビン酸ナトリウム、ク
エン酸イソプロピル、dl−α−トコフェロール、没食子
酸プロピル等が使用されている。しかしながら、近年、
化学合成品からなる食品添加物の安全性に対する消費者
意識の高まりにより、ＢＨＡやＢＨＴ等の化学合成品は
その使用が避けられる傾向にあり、また、比較的安全性
の高いとされるそれ以外の抗酸化剤も効果的に満足でき
るものはなかなか見当たらない。このような事情から、
安全性の高い、効果の十分な抗酸化剤を天然物から取得
する試みが多々なされ、実用に供されているものもあ
る。例えば、現在、食品加工等に用いられている天然物
由来の抗酸化剤としては、各種植物油に含まれるトコフ
ェロール類、各種植物組織中に含まれるフラボン、ケル
セチン、ルチン等のフラボン誘導体、茶葉、コーヒー
豆、カカオ豆等に含まれるコーヒー酸、没食子酸、フエ
ルラ酸等の没食子酸誘導体やカテキン類のポリフェノー
ル類、綿実油に含まれるゴシポール、米糠中のγ−オリ
ザノール、ゴマ油中のセザモール・セザモリン、各種香
辛料類の抽出物、タンパク加水分解物（ペプチド、アミ
ノ酸）などが挙げられる（例えば、特開昭５９−４５３
８５号、特開昭５９−１６６５８５号、特開昭６０−３
６５８４号、特公昭６１−３４７９２号、特開平３−７
５６５号等参照）。2. Description of the Related Art Conventionally, as an antioxidant, for example, BH
A (butylhydroxyanisole), BHT (butylhydroxytoluene), sodium erythorbate, isopropyl citrate, dl-α-tocopherol, propyl gallate and the like are used. However, in recent years
Due to increasing consumer awareness of the safety of food additives consisting of chemically synthesized products, the use of chemically synthesized products such as BHA and BHT tends to be avoided, and other than those that are considered to be relatively safe. It is difficult to find any effective antioxidant. Because of this,
Many attempts have been made to obtain highly safe and sufficiently effective antioxidants from natural products, and some have been put to practical use. For example, as antioxidants derived from natural products currently used in food processing, tocopherols contained in various plant oils, flavones contained in various plant tissues, quercetin, flavone derivatives such as rutin, tea leaves, and coffee. Beans, caffeic acid contained in cacao beans, gallic acid, gallic acid derivatives such as ferulic acid and polyphenols of catechins, gossypol contained in cottonseed oil, γ-oryzanol in rice bran, sezamol / sezamoline in sesame oil, various spices And the like, and protein hydrolysates (peptides, amino acids) and the like (for example, JP-A-59-453).
85, JP-A-59-166585, JP-A-60-3.
No. 6584, Japanese Patent Publication No. 61-34792, JP-A No. 3-7.
565, etc.).
【０００３】[0003]
【発明が解決しようとする課題】しかし、上記の天然物
由来の抗酸化剤も、未だ十分満足できるものではなく、
さらに新しい、優れた効果を発揮する抗酸化剤の開発が
望まれている。本発明者らは、天然物中の抗酸化剤成分
につき種々検索、研究する間に、意外にも、これまで抗
酸化剤の給源として利用されていなかったタマリンド種
皮から優れた抗酸化活性を有する化合物を単離、同定す
ることに成功し、本発明を完成するに至った。However, the above-mentioned antioxidants derived from natural products are not yet sufficiently satisfactory.
Furthermore, the development of new antioxidants that exhibit excellent effects has been desired. While conducting various searches and studies on antioxidant components in natural products, the present inventors surprisingly have excellent antioxidant activity from tamarind seed coat which has not been used as a source of antioxidants until now. The compound was successfully isolated and identified, and the present invention was completed.
【０００４】[0004]
【課題を解決するための手段】すなわち、本発明は、式
（１）：That is, the present invention provides the formula (1):
【０００５】[0005]
【化４】 [Chemical 4]
【０００６】（式中、Ｒはメトキシカルボニル基、アセ
チル基またはヒドロキシメチルカルボニル基を意味す
る）で示される化合物、特に、タマリンド種皮由来の式
（１）の化合物を有効成分としてなる抗酸化剤を提供す
るものである。式（１）の化合物中、Ｒがメトキシカル
ボニル、すなわち、式（２）：A compound represented by the formula (wherein R represents a methoxycarbonyl group, an acetyl group or a hydroxymethylcarbonyl group), particularly an antioxidant comprising a compound of the formula (1) derived from tamarind seed coat as an active ingredient. It is provided. In the compound of formula (1), R is methoxycarbonyl, that is, formula (2):
【０００７】[0007]
【化５】 [Chemical 5]
【０００８】で示される化合物以外は、文献未記載の新
規化合物であり、本発明はまた、式（３）：The compounds other than the compound represented by the formula are novel compounds which have not been described in the literature, and the present invention also provides a compound of the formula (3):
【０００９】[0009]
【化６】 [Chemical 6]
【００１０】さらには、式（４）：Further, equation (4):
【００１１】[0011]
【化７】 [Chemical 7]
【００１２】で示される化合物も提供する。以下、本発
明を詳細に説明する。本発明の抗酸化剤の有効成分とし
て用いられる式（１）の化合物は、熱帯原産のマメ科の
常緑高木タマリンド（Tamarindus indica L.）の種皮か
ら抽出、単離・精製して得られる。タマリンドは、熱帯
地方において一般的な食物として入手でき、また、その
種子粘質物が食品等の粘度調整に使用されている。式
（１）の化合物は、例えば、タマリンド種皮からつぎの
ようにして得られる。まず、タマリンドの種皮を公知の
方法で粉砕し、これを適当量の溶媒で抽出し、抽出物を
濃縮して粗抽出物を得る。抽出溶媒としては酢酸エチ
ル、エタノール等の極性あるいは非極性溶媒が使用で
き、酢酸エチルが好ましい。抽出条件は特に限定するも
のではないが、常圧〜減圧下、常温〜３０℃にて８〜１
６時間の抽出を２〜４回行えば効率良く抽出が行える。
濃縮も公知の方法が用いられるが、抽出物に与える損傷
が少ない等の点から、常温〜４０℃における減圧濃縮が
好ましい。There is also provided a compound of formula Hereinafter, the present invention will be described in detail. The compounds of formula used as an active ingredient (1) of the antioxidant of the present invention, extracted from seed coat of tropical native leguminous evergreen tree tamarind (Tamarindus indica L.), obtained by isolation and purification. Tamarind is available as a general food in the tropics, and its seed mucilage is used for adjusting the viscosity of foods and the like. The compound of formula (1) is obtained from tamarind seed coat as follows, for example. First, tamarind seed coat is pulverized by a known method, this is extracted with an appropriate amount of a solvent, and the extract is concentrated to obtain a crude extract. A polar or non-polar solvent such as ethyl acetate or ethanol can be used as the extraction solvent, and ethyl acetate is preferred. The extraction conditions are not particularly limited, but may be 8 to 1 at normal temperature to 30 ° C. under normal pressure to reduced pressure.
Extraction can be performed efficiently by performing extraction for 6 hours 2 to 4 times.
A known method is used for concentration, but vacuum concentration at room temperature to 40 ° C. is preferable from the viewpoint of less damage to the extract.
【００１３】得られた粗抽出物をさらに高速液体クロマ
トグラフィーによる精製に付す。高速液体クロマトグラ
フィーの条件は、本発明化合物を単離、精製できるもの
であれば特に限定されないが、例えば、分離カラムとし
てシリカゲル系のものを、溶媒としてトリフルオロ酢酸
含有アセトニトリル／水を用いるのが適当である。化合
物の検出は、式（１）の化合物がベンゼン環を有するの
で、２８０ｎｍの紫外部吸収によるのが好ましい。式
（１）の化合物を含む画分から、例えば、減圧乾固によ
り、溶媒を除去し、式（１）の単離・精製された化合物
を得る。The crude extract obtained is further subjected to purification by high performance liquid chromatography. The conditions of high performance liquid chromatography are not particularly limited as long as the compound of the present invention can be isolated and purified. For example, a silica gel-based one as a separation column and a trifluoroacetic acid-containing acetonitrile / water as a solvent are used. Appropriate. The compound is preferably detected by ultraviolet absorption at 280 nm because the compound of formula (1) has a benzene ring. From the fraction containing the compound of formula (1), the solvent is removed by, for example, drying under reduced pressure to obtain the isolated and purified compound of formula (1).
【００１４】かくして得られた式（１）の化合物は、そ
のまま抗酸化剤として用いてもよく、また、タマリンド
種皮からの酢酸エチル粗抽出物の状態で用いてもよい。
または、これらと、食品、化粧料、医薬品等に許容され
る公知の賦形剤や、その他適当な添加剤、例えば、乳
糖、デキストリン、ガム類、グリセリン酸エステル等を
用い、自体公知の方法で固体または液体の形態、例え
ば、粉末、ペースト、乳化液、オイル液、水溶液剤のよ
うな剤形として用いることもできる。このような製剤中
の式（１）の化合物の量は、使用対象、目的とする抗酸
化作用等に応じて適宜選択されるが、通常、０．０３〜
１重量％まで、好ましくは、０．０５〜０．５重量％で
ある。The compound of formula (1) thus obtained may be used as an antioxidant as it is, or may be used in the form of a crude ethyl acetate extract from tamarind seed coat.
Alternatively, with these, known excipients acceptable for foods, cosmetics, pharmaceuticals and the like, and other appropriate additives, for example, lactose, dextrin, gums, glyceric acid ester and the like, by a method known per se. It can also be used in solid or liquid form, for example in the form of powders, pastes, emulsions, oil solutions, aqueous solutions. The amount of the compound of the formula (1) in such a formulation is appropriately selected depending on the intended use, the intended antioxidant action, etc., but is usually 0.03 to
Up to 1% by weight, preferably 0.05 to 0.5% by weight.
【００１５】式（１）の化合物は食用に供される天然物
の種皮から得られ、毒性は極めて少ないものと考えら
れ、したがって、本発明の抗酸化剤は、食品、飼料、化
粧料、医薬品およびそれらの原料等の抗酸化剤として用
いることができる。例えば、食品等の製造工程で添加、
混和、湿潤その他の方法によって使用することができ
る。その使用量は所望の目的に応じて適宜選択できる
が、通常、式（１）の化合物の濃度が所望の製品中に
０．０５〜０．５重量％となるようにする。The compound of formula (1) is obtained from the seed coat of a natural product used for food and is considered to have extremely low toxicity. Therefore, the antioxidant of the present invention is used in foods, feeds, cosmetics and pharmaceuticals. Also, it can be used as an antioxidant for those raw materials and the like. For example, added in the manufacturing process of food etc.,
It can be used by mixing, wetting or other methods. The amount used can be appropriately selected depending on the desired purpose, but usually the concentration of the compound of formula (1) is adjusted to 0.05 to 0.5% by weight in the desired product.
【００１６】以下に実施例を示して本発明を具体的に説
明するが、本発明はこれに限定されるものではない。抗
酸化活性の測定は、リノール酸を基質としたモデル系
［ティー・オーサワ(T.Osawa)およびエム・ナミキ(M. N
amiki)、アグリカルチュラル・アンド・バイオロジカル
・ケミストリー(Agric. Biol. Chem.)、第４５巻、７３
５頁(１９８１年)］を用い、ロダン鉄法［満田ら、栄養
と食糧 第１９巻、２１０頁(１９６６年)］およびＴＢ
Ａ法［オー・オトレンジ(O. Ottolenghi)、アチーブス
・オブ・バイオケミストリー・アンド・バイオフィジッ
クス(Arch. Biochem. Biophys.)、第７９巻、３５５頁
(１９５９年)］により測定した。The present invention will be specifically described below with reference to examples, but the present invention is not limited thereto. The antioxidant activity was measured using a model system using linoleic acid as a substrate [T. Osawa and M. Namiki (M. N.
amiki), Agricultural and Biological Chemistry (Agric. Biol. Chem.), Vol. 45, 73.
5 (1981)], using the Rodan iron method [Mitsuda et al., Nutrition and Food Vol. 19, 210 (1966)] and TB.
Method A [O. Ottolenghi, Achievements of Biochemistry and Biophysics, Vol. 79, p. 355]
(1959)].
【００１７】実施例１ 抗酸化活性化合物の抽出および単離 タマリンド種皮４６０ｇを粉砕器（日本理化学機械
（株）製、Ｒ−８型）で粉砕し、２０℃、常圧下で２リ
ットルの酢酸エチルで４回抽出し、集めた抽出液を４０
℃以下で減圧濃縮し、３.４ｇの粗抽出物を得た。得ら
れた粗抽出物を分取高速液体クロマトグラフィー［カラ
ム：野村化学（株）製Develosil ODS-10（２０ｍｍ×２
５０ｍｍ）、溶媒：０．１％（ｗ／ｖ）トリフルオロ酢
酸含有１７％（ｖ／ｖ）アセトニトリル／水、流量：
５．０ｍｌ／分、検出：２８０ｎｍ紫外部吸収］により
付し、単一の成分からなる抗酸化活性画分と、複数の成
分からなる抗酸化活性画分とを分取した。単一の成分か
らなる画分から溶媒を減圧除去して抗酸化活性物質２８
１．２ｍｇを得、これを化合物２と命名した。 Example 1 Extraction and Isolation of Antioxidant Compounds 460 g of tamarind seed coat was crushed with a crusher (R-8 type, manufactured by Nippon Rikagaku Kikai Co., Ltd.), and 2 liters of ethyl acetate was added at 20 ° C. under normal pressure. Extracted 4 times with 40
Concentration under reduced pressure at or below ℃ gave 3.4 g of crude extract. The obtained crude extract was subjected to preparative high performance liquid chromatography [column: Novel Chemical Co., Ltd. Develosil ODS-10 (20 mm × 2
50 mm), solvent: 0.1% (w / v) trifluoroacetic acid-containing 17% (v / v) acetonitrile / water, flow rate:
5.0 ml / min, detection: 280 nm ultraviolet absorption] to separate an antioxidant activity fraction consisting of a single component and an antioxidant activity fraction consisting of a plurality of components. The solvent is removed under reduced pressure from the fraction consisting of a single component, and the antioxidant active substance 28
1.2 mg was obtained and was named compound 2.
【００１９】一方、複数の成分をを含む方の画分をさら
に分取高速液体クロマトグラフィー［カラム：野村化学
（株）製Develosil ODS-10（２０ｍｍ×２５０ｍｍ）、
溶媒：０．１％（ｗ／ｖ）トリフルオロ酢酸含有７％
（ｖ／ｖ）アセトニトリル／水、流量：５．０ｍｌ／
分、検出：２８０ｎｍ紫外部吸収］に付し、各々、単一
の成分を含む２画分を分取した。これから溶媒を減圧除
去し、各々、抗酸化活性物質２１．３ｍｇおよび７．８
ｍｇを得、これを、各々、化合物１および３と命名し
た。On the other hand, the fraction containing a plurality of components was further subjected to preparative high performance liquid chromatography [column: Novel Chemical Co., Ltd. Develosil ODS-10 (20 mm × 250 mm),
Solvent: 0.1% (w / v) trifluoroacetic acid-containing 7%
(V / v) acetonitrile / water, flow rate: 5.0 ml /
Min., Detection: 280 nm ultraviolet absorption], and two fractions each containing a single component were collected. The solvent was removed from this under reduced pressure, and 21.3 mg and 7.8 of antioxidant active substances, respectively.
mg were obtained and were named compounds 1 and 3, respectively.
【００２０】実施例２ 化合物１〜３の同定 化合物１〜３の構造解析を、紫外部吸収（ＵＶ）スペク
トル、赤外吸収（ＩＲ）スペクトル、電子衝撃質量分析
スペクトル（ＥＩ−ＭＳ）、一次元1Ｈ核磁気共鳴吸収
（1Ｈ−ＮＭＲ、ＣＤ3ＯＤ，４００ＭＨｚ）および13Ｃ
核磁気共鳴吸収（13Ｃ−ＮＭＲ、ＣＤ3ＯＤ，１００Ｍ
Ｈｚ）により行った。化合物１の結果を表１に、化合物
２の結果を表２、化合物３の結果を表３に示す。さら
に、化合物１〜３について二次元ＮＭＲ（ＣＯＳＹ，Ｈ
ＭＱＣ，ＨＭＢＣ）を行い、表１〜３の結果から、化合
物１を、上記の式（２）で示される３，４−ジヒドロキ
シ安息香酸メチル、化合物２を上記の式（３）で示され
る３，４−ジヒドロキシフェニルアセテート、化合物３
を上記式（４）で示される２−ヒドロキシ−３'，４'−
ジヒドロキシアセトフェノンと同定した。 Example 2 Identification of Compounds 1 to 3 Structural analysis of Compounds 1 to 3 was carried out by ultraviolet absorption (UV) spectrum, infrared absorption (IR) spectrum, electron impact mass spectrometry spectrum (EI-MS), one-dimensional analysis. 1 H nuclear magnetic resonance absorption ( 1 H-NMR, CD 3 OD, 400 MHz) and 13 C
Nuclear magnetic resonance absorption ( 13 C-NMR, CD 3 OD, 100M
Hz). The results of Compound 1 are shown in Table 1, the results of Compound 2 are shown in Table 2, and the results of Compound 3 are shown in Table 3. Furthermore, two-dimensional NMR (COSY, H
MQC, HMBC), and from the results of Tables 1 to 3, compound 1 is methyl 3,4-dihydroxybenzoate represented by the above formula (2) and compound 2 is 3 represented by the above formula (3). , 4-dihydroxyphenylacetate, compound 3
To 2-hydroxy-3 ′, 4′- represented by the above formula (4)
It was identified as dihydroxyacetophenone.
【００２１】[0021]
【表１】 [Table 1]
【００２２】[0022]
【表２】 [Table 2]
【００２３】[0023]
【表３】 [Table 3]
【００２４】実施例３ 化合物１〜３の抗酸化活性 リノール酸０.１３ｍｌ、９９％蒸留エタノール１０ｍ
ｌの混合液に試料を最終濃度として２０μＭになるよう
に添加し、これに５０ｍＭリン酸緩衝液（ｐＨ＝７．
０）１０ｍｌを加え、蒸留水で２５ｍｌになるようにメ
スアップした。なお、比較のために試料無添加の対照お
よび標準試料としてα−トコフェロールを２０μＭ添加
したものを用意した。これらを５０ｍｌ共栓付きフラス
コに入れ、パラフィルムで密栓し、４０℃で保存し、経
時的に抗酸化活性をロダン鉄法、ＴＢＡ法により測定し
た。その結果を図１（ロダン鉄法）および図２（ＴＢＡ
法）に示した。なお、結果は、対照（無添加）の吸光度
（酸化度）を１００％としたときの各試料添加系におけ
る酸化の度合いを％で表した。化合物１〜３はいずれも
２０μＭの濃度でロダン鉄法、ＴＢＡ法いずれの方法に
おいても抗酸化活性を示した。化合物１および３の抗酸
化活性が強く、α−トコフェロールと同レベルの抗酸化
活性であった。 Example 3 Antioxidant activity of compounds 1 to 3 0.13 ml of linoleic acid, 10 m of 99% distilled ethanol
The sample was added to the mixed solution of 1 to a final concentration of 20 μM, and 50 mM phosphate buffer (pH = 7.
0) 10 ml was added, and distilled water was added to make 25 ml. For comparison, a control to which no sample was added and a standard sample to which 20 μM of α-tocopherol was added were prepared. These were placed in a 50 ml stoppered flask, sealed tightly with Parafilm, stored at 40 ° C., and the antioxidant activity was measured with the Rhodan iron method and the TBA method over time. The results are shown in Fig. 1 (Rhodan iron method) and Fig. 2 (TBA
Method). In addition, the results are shown in% of the degree of oxidation in each sample addition system when the absorbance (oxidation degree) of the control (no addition) is 100%. Compounds 1 to 3 each showed an antioxidant activity at a concentration of 20 μM by both the rhodan iron method and the TBA method. Compounds 1 and 3 had strong antioxidant activity, and had the same level of antioxidant activity as α-tocopherol.
【００２５】[0025]
【発明の効果】以上記載したごとく、本発明によれば、
食品、飼料、化粧料、医薬品およびそれらの原料等に適
した、安全性の高い、かつ優れた活性を有する、タマリ
ンド種皮由来の抗酸化剤が提供される。As described above, according to the present invention,
Provided is a highly safe and highly active antioxidant derived from tamarind seed coat, which is suitable for foods, feeds, cosmetics, pharmaceuticals and raw materials thereof.
【図１】 ロダン鉄法で測定した抗酸化活性を示すグラ
フ。FIG. 1 is a graph showing antioxidant activity measured by the Rhodan iron method.
【図２】 ＴＢＡ法で測定した抗酸化活性を示すグラ
フ。FIG. 2 is a graph showing antioxidant activity measured by TBA method.
Claims (5)
ヒドロキシメチルカルボニル基を意味する）で示される
化合物を有効成分としてなる抗酸化剤。1. Formula (1): (In the formula, R means a methoxycarbonyl group, an acetyl group or a hydroxymethylcarbonyl group), which is an antioxidant.
抽出されたものである請求項１記載の抗酸化剤。2. The antioxidant according to claim 1, wherein the compound of formula (1) is extracted from tamarind seed coat.
酸エチル抽出物として含有する請求項１記載の抗酸化
剤。3. The antioxidant according to claim 1, which contains the compound of formula (1) as an ethyl acetate extract of tamarind seed coat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7471594A JPH07268322A (en) | 1994-02-09 | 1994-04-13 | Antioxidation agent |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1519094 | 1994-02-09 | ||
| JP6-15190 | 1994-02-09 | ||
| JP7471594A JPH07268322A (en) | 1994-02-09 | 1994-04-13 | Antioxidation agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07268322A true JPH07268322A (en) | 1995-10-17 |
Family
ID=26351306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7471594A Pending JPH07268322A (en) | 1994-02-09 | 1994-04-13 | Antioxidation agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07268322A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10158646A (en) * | 1996-11-29 | 1998-06-16 | Q P Corp | Antioxidant composition and food or feed containing the same |
| JP2010174118A (en) * | 2009-01-29 | 2010-08-12 | Soda Aromatic Co Ltd | New antioxidant, active oxygen-eliminating agent and aromatizing cosmetic |
-
1994
- 1994-04-13 JP JP7471594A patent/JPH07268322A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10158646A (en) * | 1996-11-29 | 1998-06-16 | Q P Corp | Antioxidant composition and food or feed containing the same |
| JP2010174118A (en) * | 2009-01-29 | 2010-08-12 | Soda Aromatic Co Ltd | New antioxidant, active oxygen-eliminating agent and aromatizing cosmetic |
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