JP2008133192A - Antidiabetic agent - Google Patents

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JP2008133192A
JP2008133192A JP2005285553A JP2005285553A JP2008133192A JP 2008133192 A JP2008133192 A JP 2008133192A JP 2005285553 A JP2005285553 A JP 2005285553A JP 2005285553 A JP2005285553 A JP 2005285553A JP 2008133192 A JP2008133192 A JP 2008133192A
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isocartamidine
antidiabetic agent
cartamidine
flavanone
flavanone compound
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Satoshi Kumazawa
智 熊沢
Tsumoru Watanabe
積 渡邉
Yoshiharu Ito
義治 伊藤
Atsuko Ezawa
敦子 江澤
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Kureha Corp
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Priority to JP2005285553A priority Critical patent/JP2008133192A/en
Priority to PCT/JP2006/319561 priority patent/WO2007037423A1/en
Priority to JP2007537734A priority patent/JP4966859B2/en
Publication of JP2008133192A publication Critical patent/JP2008133192A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Organic Chemistry (AREA)
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  • Diabetes (AREA)
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Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new antidiabetic agent that controls an excessive blood glucose status after meal and has an excellent effect of preventing and treating diabetes. <P>SOLUTION: The antidiabetic agent contains carthamidin (4',5,6,7-tetrahydroxyflavanone) being a flavanone compound and/or isocarthamidin (4',5,7,8-tetrahydroxyflavanone) being similarly a flavanone compound as an active ingredient. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は、抗糖尿病活性を有するフラバノン化合物であるカルタミジンおよびイソカルタミジンに関する。   The present invention relates to cartamidine and isocartamidine which are flavanone compounds having anti-diabetic activity.

近年、摂取カロリーの過多が生活習慣病の原因となっていることから、摂取カロリーの制限が求められている。代表的な生活習慣病のうち、特に糖尿病は我が国において最も患者数が多い生活習慣病の一つである。糖尿病の特徴は、食事により摂取された炭水化物由来の糖分が消化管から吸収されて血中に入ったときに、血糖値が高過ぎたり、高血糖状態が持続したりすることであり、これら炭水化物の消化を抑え、生体内でエネルギーに変換されるのを阻止することは糖尿病など生活習慣病の予防・治療に有効であると考えられる。   In recent years, excessive intake of calories has been a cause of lifestyle-related diseases, and therefore, restriction of intake calories has been demanded. Among typical lifestyle-related diseases, diabetes is one of the most common lifestyle-related diseases in Japan. A characteristic of diabetes is that when sugars derived from carbohydrates taken from meals are absorbed from the digestive tract and enter the blood, the blood sugar level is too high or the hyperglycemic state persists. It is considered effective to prevent the digestion of food and prevent it from being converted into energy in vivo for the prevention and treatment of lifestyle-related diseases such as diabetes.

ここで、本発明に関連のある事項として、フラバノン化合物であるカルタミジンおよびイソカルタミジンについて、以下説明する。   Here, as a matter relevant to the present invention, cartamidine and isocartamidine which are flavanone compounds will be described below.

カルタミジン(carthamidin)は、化学式Ｃ15Ｈ12Ｏ6のフラバノン化合物（4',5,6,7-tetrahydroxyflavanone）であり、ナリンゲニン（naringenin；4',5,7-trihydroxyflavanone）の６位に水酸基を有する化合物、いわゆる６−ヒドロキシナリンゲニン（6-hydroxynaringenin）のことである。
イソカルタミジン(isocarthamidin)は、化学式Ｃ15Ｈ12Ｏ6のフラバノン化合物（4',5,7,8-tetrahydroxyflavanone）であり、いわゆる８−ヒドロキシナリンゲニン（8-hydroxynaringenin）のことである。 Carthamidin is a flavanone compound (4 ', 5,6,7-tetrahydroxyflavanone) with the chemical formula C 15 H 12 O 6 , and a hydroxyl group is placed at the 6-position of naringenin (naringenin; 4', 5,7-trihydroxyflavanone). It is a so-called 6-hydroxynaringenin.
Isocarthamidin is a flavanone compound (4 ′, 5,7,8-tetrahydroxyflavanone) having the chemical formula C 15 H 12 O 6 and is a so-called 8-hydroxynaringenin.

カルタミジン及びイソカルタミジンに関して、例えば、以下の文献がある。
特許文献１には、イソカルタミジンの消臭効果が、特許文献２〜４にはこれらの化合物の抗酸化効果が、特許文献５にはこれらの化合物のコガネバナからの抽出例が、それぞれ開示されている。
また、非特許文献では、紅花の紅色色素などを酸加水分解することで生成することが知られており、例えば、非特許文献１、非特許文献２などではそれらの合成法が報告されている。また、非特許文献３には、コガネバナの葉抽出物から分離精製された例が報告されている。その他、非特許文献４、非特許文献５などには、抗酸化効果が示されている。
特開昭６１−２６８２５９号公報 特開２００２−２８１９９５号公報 特開２００２−２９３７７９号公報 特開２００３−１０２４３０号公報 ロシア特許２２２８６７３号 Bull. Chem. Soc. Jpn., Vol.51 (12) 3627-3630(1970) Chem. Lett.915-916(1973) 薬学雑誌96（3）381-383（1976） 日本食品科学工学会誌 Vol.51 (3) 181-184 (2004) Biosci. Biotechnol. Biochem., 67(7) 1443-1450 (2003) Regarding cartamidine and isocartamidine, for example, there are the following documents.
Patent Document 1 discloses the deodorizing effect of isocartamidine, Patent Documents 2 to 4 disclose the antioxidant effect of these compounds, and Patent Document 5 discloses an extraction example of these compounds from Cognevana. ing.
In addition, in non-patent literature, it is known that the red pigment of safflower is generated by acid hydrolysis. For example, Non-patent literature 1, Non-patent literature 2 and the like report their synthesis methods. . Non-Patent Document 3 reports an example of separation and purification from a leaf extract of Scutellaria. In addition, Non-Patent Document 4, Non-Patent Document 5, and the like show an antioxidant effect.
Japanese Patent Laid-Open No. 61-268259 JP 2002-281995 A Japanese Patent Laid-Open No. 2002-293779 JP 2003-102430 A Russian patent 2228673 Bull. Chem. Soc. Jpn., Vol. 51 (12) 3627-3630 (1970) Chem. Lett. 915-916 (1973) Pharmaceutical Journal 96 (3) 381-383 (1976) Japanese Journal of Food Science and Technology Vol.51 (3) 181-184 (2004) Biosci. Biotechnol. Biochem., 67 (7) 1443-1450 (2003)

本発明の目的は、新規な抗糖尿病剤を提供することである。   An object of the present invention is to provide a novel antidiabetic agent.

本発明者らは上記事情に鑑み、種々の炭水化物消化酵素を阻害する物質を種々検討した結果、植物中に含まれ、種々の炭水化物消化酵素阻害に優れたフラバノン化合物であるカルタミジンおよびイソカルタミジンを見出した。   In view of the above circumstances, the present inventors have studied various substances that inhibit various carbohydrate digestive enzymes. As a result, the present inventors have found that cartamidine and isocartamidine, which are flavanone compounds contained in plants and excellent in inhibiting various carbohydrate digestive enzymes. I found it.

従来、これらのフラバノン化合物は、消臭効果、抗酸化効果を発揮するに止まっており、食後血糖値上昇抑制作用に関しては、現在まで知られていなかった。それに対し、本発明では、これらのフラバノン化合物が食後の過血糖状態を抑制して糖尿病の予防及び治療に優れた効果を有することを新規に見出した。   Conventionally, these flavanone compounds have only been able to exert a deodorizing effect and an antioxidant effect, and the postprandial blood glucose level inhibitory action has not been known so far. On the other hand, in the present invention, it has been newly found that these flavanone compounds have an excellent effect in the prevention and treatment of diabetes by suppressing the hyperglycemic state after meal.

そこで、本発明では、フラバノン化合物であり、「化１」の構造を有するカルタミジン（１）、及び／又は、同じくフラバノン化合物であり「化２」の構造を有するイソカルタミジン（２）を有効成分として含有する抗糖尿病剤を提供する。   Therefore, in the present invention, cartamidine (1) which is a flavanone compound and has a structure of “Chemical Formula 1” and / or isocartamidine (2) which is also a flavanone compound and has a structure of “Chemical Formula 2” is an active ingredient As an antidiabetic agent.

なお、カルタミジン及びイソカルタミジンの好適な適用量は、年齢、症状等によって異なるが、例えば、成人１回につき１〜５００ｍｇ程度、好ましくは５〜３００ｍｇ程度、である。   In addition, although the suitable application amount of a cartamidine and an isocartamidine changes with age, a symptom, etc., it is about 1-500 mg per adult, Preferably it is about 5-300 mg.

本発明に係る化合物は、糖尿病の予防及び治療に有効である。   The compound according to the present invention is effective for the prevention and treatment of diabetes.

実施例１では、カルタミジン及びイソカルタミジンについて、α−グルコシダーゼ阻害活性の測定を行った。   In Example 1, the α-glucosidase inhibitory activity was measured for cartamidine and isocartamidine.

実験手順の概要は次の通りである。
ラットアセトン粉末（ＳＩＧＭＡ社製）に９倍量の０．０５Ｍマレイン酸緩衝液（ｐＨ６．０）を加え、超音波処理後、３０００ｒｐｍ・１０分間遠心、上清を酵素液とした。マレイン酸緩衝液（ｐＨ６．０）に所定の濃度で溶解させたカルタミジン又はイソカルタミジン５０μＬに、マレイン酸緩衝液（ｐＨ６．０）に溶解した２％ショ糖５０μＬを加え、３７℃・５分間プレインキュベート後、マレイン酸緩衝液（ｐＨ６．０）で２倍希釈した酵素液を５０μＬ加え、３７℃・６０分間反応した。反応終了後、９５℃・１０分間で酵素を失活させ、１５０００ｒｐｍ・１０分間遠心後、上清中のグルコース量をＳＹＮＣＨＲＯＮ ＣＸ３Δ（ＢＥＣＫＭＡＮ社製）にて測定した。
また、コントロールとして前記試料溶液の代わりにマレイン酸緩衝液（ｐＨ６．０）のみの溶液を使用して同様に測定した。 The outline of the experimental procedure is as follows.
Nine times the amount of 0.05 M maleate buffer (pH 6.0) was added to rat acetone powder (manufactured by SIGMA), sonicated, centrifuged at 3000 rpm for 10 minutes, and the supernatant was used as the enzyme solution. 50 μL of 2% sucrose dissolved in maleate buffer (pH 6.0) is added to 50 μL of cartamidine or isocartamidine dissolved in maleate buffer (pH 6.0) at a predetermined concentration, and the temperature is 37 ° C. for 5 minutes. After pre-incubation, 50 μL of enzyme solution diluted 2-fold with maleic acid buffer solution (pH 6.0) was added, and reacted at 37 ° C. for 60 minutes. After completion of the reaction, the enzyme was inactivated at 95 ° C. for 10 minutes, centrifuged at 15000 rpm for 10 minutes, and the amount of glucose in the supernatant was measured with SYNCHRON CX3Δ (manufactured by BECKMAN).
Moreover, it measured similarly using the solution of only maleic acid buffer (pH 6.0) instead of the said sample solution as control.

結果を表１に示す。
表中の数値（下段）は、酵素阻害活性を示す値（％）であり、各サンプルを用いた場合におけるグルコース量を、マレイン酸緩衝液を用いた場合（コントロール）におけるグルコース量で除することにより算出した。

Figure 2008133192
The results are shown in Table 1.
The numerical values in the table (lower) are values (%) indicating enzyme inhibitory activity, and the amount of glucose when using each sample is divided by the amount of glucose when using maleate buffer (control). Calculated by
Figure 2008133192

その結果、表１に示す通り、カルタミジン及びイソカルタミジンは、それぞれ、優れたα−グルコシダーゼ阻害活性を有することがわかった。   As a result, as shown in Table 1, it was found that cartamidine and isocartamidine each have excellent α-glucosidase inhibitory activity.

実施例２では、カルタミジン及びイソカルタミジンについて、マルターゼ阻害活性の測定を行った。   In Example 2, maltase inhibitory activity was measured for cartamidine and isocartamidine.

実験手順の概要は次の通りである。
ラットアセトン粉末（ＳＩＧＭＡ社製）に９倍量の０．０５Ｍマレイン酸緩衝液（ｐＨ６．０）を加え、超音波処理後、３０００ｒｐｍ・１０分間遠心、上清を酵素液とした。マレイン酸緩衝液（ｐＨ６．０）に所定の濃度で溶解させたカルタミジン又はイソカルタミジン５０μＬに、マレイン酸緩衝液（ｐＨ６．０）に溶解した２％マルトース５０μＬを加え、３７℃・５分間プレインキュベート後、０．０５Ｍマレイン酸緩衝液（ｐＨ６．０）で２０倍希釈した酵素液を５０μＬ加え、３７℃・６０分間反応した。反応終了後、９５℃・１０分間で酵素を失活させ、１５０００ｒｐｍ・１０分間遠心後、上清中のグルコース量をＳＹＮＣＨＲＯＮ ＣＸ３Δ（ＢＥＣＫＭＡＮ社製）にて測定した。
また、コントロールとして前記試料溶液の代わりにマレイン酸緩衝液（ｐＨ６．０）のみの溶液を使用して同様に測定した。 The outline of the experimental procedure is as follows.
Nine times the amount of 0.05 M maleate buffer (pH 6.0) was added to rat acetone powder (manufactured by SIGMA), sonicated, centrifuged at 3000 rpm for 10 minutes, and the supernatant was used as the enzyme solution. 50 μL of 2% maltose dissolved in maleate buffer solution (pH 6.0) is added to 50 μL of cartamidine or isocartamidine dissolved in maleate buffer solution (pH 6.0) at a predetermined concentration. After the incubation, 50 μL of an enzyme solution diluted 20-fold with 0.05 M maleate buffer (pH 6.0) was added and reacted at 37 ° C. for 60 minutes. After completion of the reaction, the enzyme was inactivated at 95 ° C. for 10 minutes, centrifuged at 15000 rpm for 10 minutes, and the amount of glucose in the supernatant was measured with SYNCHRON CX3Δ (manufactured by BECKMAN).
Moreover, it measured similarly using the solution of only maleic acid buffer (pH 6.0) instead of the said sample solution as control.

結果を表２に示す。
表中の数値（下段）は、前記と同様、酵素阻害活性を示す値（％）であり、各サンプルを用いた場合におけるグルコース量を、マレイン酸緩衝液を用いた場合（コントロール）におけるグルコース量で除することにより算出した。

Figure 2008133192
The results are shown in Table 2.
The numerical value (lower part) in the table is a value (%) indicating enzyme inhibitory activity as described above, and the amount of glucose when using each sample is the amount of glucose when using maleate buffer (control). It was calculated by dividing by.
Figure 2008133192

その結果、表２に示す通り、カルタミジン及びイソカルタミジンは、それぞれ、優れたマルターゼ阻害活性を有することがわかった。
As a result, as shown in Table 2, it was found that cartamidine and isocartamidine each have excellent maltase inhibitory activity.

Claims (3)

フラバノン化合物であり下記「化１」の構造を有するカルタミジン（１）、及び／又は、同じくフラバノン化合物であり下記「化２」の構造を有するイソカルタミジン（２）を有効成分として含有する抗糖尿病剤。
Figure 2008133192
Figure 2008133192
Anti-diabetic containing flavanone compound and cartamidine (1) having the structure of the following "chemical formula 1" and / or isocartamidine (2) having the structure of the following "chemical formula 2" and the same flavanone compound as an active ingredient Agent.
Figure 2008133192
Figure 2008133192
α−グルコシダーゼ阻害活性又は抑制活性を有することを特徴とする請求項１記載の抗糖尿病剤。   The antidiabetic agent according to claim 1, which has α-glucosidase inhibitory activity or suppressive activity. マルターゼ阻害活性又は抑制活性を有することを特徴とする請求項１又は請求項２記載の抗糖尿病剤。

The antidiabetic agent according to claim 1 or 2, which has a maltase inhibitory activity or a suppressive activity.

JP2005285553A 2005-09-29 2005-09-29 Antidiabetic agent Pending JP2008133192A (en)

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JP2005285553A JP2008133192A (en) 2005-09-29 2005-09-29 Antidiabetic agent
PCT/JP2006/319561 WO2007037423A1 (en) 2005-09-29 2006-09-29 Antidiabetic agent
JP2007537734A JP4966859B2 (en) 2005-09-29 2006-09-29 Antidiabetic

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JP2010248130A (en) * 2009-04-16 2010-11-04 Kureha Corp Anti-diabetic agent and use thereof
JP2016522255A (en) * 2013-06-19 2016-07-28 アクセス ビジネス グループ インターナショナル エルエルシーＡｃｃｅｓｓ Ｂｕｓｉｎｅｓｓ Ｇｒｏｕｐ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｌｌｃ Plant-based ketohexokinase inhibitors to support weight management
JP2019205386A (en) * 2018-05-29 2019-12-05 丸善製薬株式会社 INHIBITOR OF α-GLUCOSIDASE ACTIVITY AND SUPPRESSOR OF RISE IN BLOOD SUGAR LEVEL

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010248130A (en) * 2009-04-16 2010-11-04 Kureha Corp Anti-diabetic agent and use thereof
JP2016522255A (en) * 2013-06-19 2016-07-28 アクセス ビジネス グループ インターナショナル エルエルシーＡｃｃｅｓｓ Ｂｕｓｉｎｅｓｓ Ｇｒｏｕｐ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｌｌｃ Plant-based ketohexokinase inhibitors to support weight management
JP2019205386A (en) * 2018-05-29 2019-12-05 丸善製薬株式会社 INHIBITOR OF α-GLUCOSIDASE ACTIVITY AND SUPPRESSOR OF RISE IN BLOOD SUGAR LEVEL
JP7239135B2 (en) 2018-05-29 2023-03-14 丸善製薬株式会社 α-Glucosidase activity inhibitor and blood sugar elevation inhibitor

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