JP4744297B2 - 糖脂質含有組成物、その用途およびその製造方法 - Google Patents
糖脂質含有組成物、その用途およびその製造方法 Download PDFInfo
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- JP4744297B2 JP4744297B2 JP2005514037A JP2005514037A JP4744297B2 JP 4744297 B2 JP4744297 B2 JP 4744297B2 JP 2005514037 A JP2005514037 A JP 2005514037A JP 2005514037 A JP2005514037 A JP 2005514037A JP 4744297 B2 JP4744297 B2 JP 4744297B2
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- Prior art keywords
- glycolipid
- containing composition
- fraction
- present
- lipase
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/21—Amaranthaceae (Amaranth family), e.g. pigweed, rockwort or globe amaranth
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- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A—HUMAN NECESSITIES
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- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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Description
A)海藻または陸生植物から精製され、少なくとも糖脂質としてモノガラクトシルジアシルグリセロール、ジガラクトシルジアシルグリセロール、およびスルホキノボシルジアシルグリセロールを含有する糖脂質含有組成物(以下、特に「第1の糖脂質含有組成物」という場合がある)。
B)上記第1の糖脂質含有組成物をリパーゼ処理することにより得られ、少なくとも糖脂質としてモノガラクトシルモノアシルグリセロール、およびスルホキノボシルモノアシルグリセロールを含有する糖脂質含有組成物(以下、特に「第2の糖脂質含有組成物」という場合がある)。
C)上記第1又は第2の糖脂質含有組成物を有効成分とするDNA合成酵素阻害剤。
D)上記第1又は第2の糖脂質含有組成物を有効成分とする抗癌剤。
E)上記第1又は第2の糖脂質含有組成物を有効成分とする医薬用組成物。
F)上記第1又は第2の糖脂質含有組成物を含む食用組成物。
G)海藻または陸生植物を原料として、少なくとも糖脂質としてモノガラクトシルジアシルグリセロール、ジガラクトシルジアシルグリセロール、およびスルホキノボシルジアシルグリセロールを含有する糖脂質含有組成物を製造する方法。
H)上記G)記載の方法により製造された糖脂質含有組成物をリパーゼ処理することにより、少なくとも糖脂質としてモノガラクトシルモノアシルグリセロール、およびスルホキノボシルモノアシルグリセロールを含有する糖脂質含有組成物を製造する方法。
I)上記G)記載の方法において、疎水クロマトグラフィーを用いて植物抽出物(海藻または陸生植物からの抽出物の意味。以下同じ。)から糖脂質画分を精製する工程を含む方法。
J)上記I)記載の方法において、糖脂質の溶出にエタノール等のアルコールまたはアセトン等の有機溶媒を用い、50%〜75%の含水有機溶媒にて水溶性物質を溶出後、85%〜100%の含水有機溶媒もしくは有機溶媒にて糖脂質を溶出する工程を含む方法。
K)上記G)記載の方法において、植物抽出物を得る前に、植物を40℃〜80℃の温水で洗浄し、水溶性成分を除去する工程を含む方法。
L)上記G)記載の方法において、原料にホウレン草(Spinacia)等の緑黄色野菜を使用する方法。
(1)本発明の糖脂質含有組成物およびその製造方法
前述のとおり、本発明の第1の糖脂質含有組成物は、海藻または陸生植物から精製され、少なくとも糖脂質としてモノガラクトシルジアシルグリセロール、ジガラクトシルジアシルグリセロール、およびスルホキノボシルジアシルグリセロール(以下、これら糖脂質をそれぞれ「MGDG」、「DGDG」、「SQDG」と略称する)を含有するものである。また、本発明の第2の糖脂質含有組成物は、本発明の第1の糖脂質含有組成物をリパーゼ処理することにより得られ、少なくとも糖脂質としてモノガラクトシルモノアシルグリセロール、およびスルホキノボシルモノアシルグリセロール(以下、これら糖脂質をそれぞれ「MGMG」、「SQMG」と略称する)を含有するものである。
また、各糖脂質は薬学的に許容され得る塩の状態であってもよい。このような塩としては、フッ化水素酸塩、塩酸塩などのハロゲン化水素酸塩、硫酸塩、硝酸塩などの無機酸塩、ナトリウム塩、カリウム塩などのアルカリ金属塩、スルホン酸塩、有機酸塩、およびアミノ酸塩が挙げられ、好適には塩酸塩、硫酸塩、硝酸塩、ナトリウム塩、カリウム塩を挙げることができる。
上述した本発明の第1および第2の糖脂質含有組成物はいずれも、DNA合成酵素阻害活性、癌細胞増殖抑制活性、抗腫瘍活性といった有用な生理活性を有することから、DNA合成酵素阻害剤、抗癌剤(制癌剤)として利用可能であり、特に機能性食品などに好適に用いることができ、例えば抗癌作用または癌予防効果をもつ機能性食品として利用できる。
本実施例では、図2に示される方法により、原料のホウレン草(Spinacia oleracea L.)から本発明の第1の糖脂質含有組成物を精製した。まず、市販ホウレン草の乾燥物100gを細断した後、水溶性成分をできるだけ除去するために、60℃の温水1Lで2回洗浄した。次に、濾紙を使用して濾過後、水分を除去し、得られた固形物(残渣)に1Lのエタノールを加え、撹拌しながら60℃で還流抽出を2回行った。抽出液は濾過後、減圧下で濃縮を行い、ホウレン草のオイル状抽出物20.5gを得た。
上記方法により得られた糖脂質画分(画分II)すなわち本発明の第1の糖脂質含有組成物のDNA合成酵素阻害活性を調べた。DNA合成酵素には哺乳動物由来のDNA合成酵素α、βを使用した。より詳細には、DNA合成酵素αは、牛胸腺の抽出液を抗体カラムクロマトグラフィーで精製した標品を、DNA合成酵素βは、ラットのDNA合成酵素β遺伝子を導入した組換え大腸菌を培養後、破砕して精製した標品を用いた。
(a−b)/a×100=阻害率(%)
として評価した。得られた結果を図4に示す。同図は、DNA合成酵素αに対する阻害結果を示すグラフであり、図中、三角印はエタノール抽出液存在下での阻害結果、菱形印、丸印、四角印はそれぞれ画分I〜III存在下での阻害結果である。同図に示すように、画分IIには強いDNA合成酵素α阻害活性が認められ、画分IIの50%阻害濃度(IC50)はおよそ40μg/mlであった。一方、エタノール抽出液、画分IおよびIIIは、DNA合成酵素αを殆ど阻害しなかった。
次に、上記ホウレン草各画分およびエタノール抽出液が癌細胞増殖抑制作用を有するかどうかを検討した。実験には、ヒト胃癌細胞株であるNUGC−3細胞を使用し、種々の濃度のホウレン草画分(またはエタノール抽出液)を添加してインキュベーションし、48時間後、各場合における癌細胞の生存率を通常のMTTアッセイにより決定した。
以下の方法により、上記糖脂質画分(画分II)をリパーゼ処理し、第2の糖脂質含有組成物を精製した。
図13に示すように、糖脂質画分(画分II)10mg/mlおよびブタ膵臓リパーゼ10mg/mlを反応液(0.2M Tris−HCl(pH7.6)、0.25M CaCl2)において37℃、20分間振とう反応させ、糖脂質をリパーゼにより加水分解し、ジアシルグリセロールタイプのものからモノアシルグリセロールタイプのものを生成し、その後6NのHClで反応を止めた。
図4の実験と同様の方法により、リパーゼ処理前の糖脂質画分(第1の糖脂質含有組成物)およびリパーゼ処理後の糖脂質画分(第2の糖脂質含有組成物)のDNA合成酵素阻害活性を調べ、両者を比較した。その結果を図7に示す。図中、黒丸印は、DNA合成酵素αに対するリパーゼ処理前の糖脂質画分、黒四角印は、DNA合成酵素αに対するリパーゼ処理後の糖脂質画分、白丸印は、DNA合成酵素βに対するリパーゼ処理前の糖脂質画分、白四角印は、DNA合成酵素βに対するリパーゼ処理後の糖脂質画分、の各阻害結果を示すものである。
さらに、上記第1および第2の糖脂質含有組成物のin vivo抗腫瘍活性を調査した。実験動物にはシリアン(ゴールデン)ハムスターを用い、同ハムスターへ黒色腫(Melanotic No.179,D1−179)片を皮下移植して、一週間定着させてから、糖脂質含有組成物を生理食塩水に溶かして、一日おきに10mg/kgを皮下注射により投与して、腫瘍体積を測定した。その結果を図9および図10に示す。
以上の結果より、本発明の糖脂質含有組成物は、ヒト由来の腫瘍に対してもハムスター由来の腫瘍と同様に抑制活性が認められることから、健康食品の開発などに有用である。
以上の結果より、本発明の糖脂質含有組成物は、飲料水などとして経口投与する抗癌機能性食品の開発などに有用である。
上記の方法により調製した本発明の糖脂質含有組成物150mg、精製大豆油125mg、ミツロウ15mgおよびビタミンE10mgを窒素ガス雰囲気下で約40℃に加温し、十分に混合して均質な液状物とした。これをカプセル充填機に供給して1粒内容量300mgのゼラチン被覆カプセル製剤を試作した。この製剤は医薬用組成物または食用組成物として利用できるものである。
Claims (5)
- 海藻または陸生植物を原料植物として、少なくとも糖脂質としてモノガラクトシルジアシルグリセロール(MGDG)、ジガラクトシルジアシルグリセロール(DGDG)、およびスルホキノボシルジアシルグリセロール(SQDG)を含有する糖脂質含有組成物を製造する方法において、
疎水クロマトグラフィーを用いて植物抽出物から糖脂質画分を精製する工程であって、
該疎水クロマトグラフィー工程において50%〜75%の含水エタノール溶液にて水溶性物質を溶出後、85%〜100%の含水エタノール溶液にて糖脂質を溶出する工程を含む方法。 - 請求項1記載の方法により製造された糖脂質含有組成物を、さらにリパーゼ処理することにより、少なくとも糖脂質としてモノガラクトシルモノアシルグリセロール(MGMG)、およびスルホキノボシルモノアシルグリセロール(SQMG)を含有する糖脂質含有組成物を製造する方法。
- 請求項1または2記載の方法において、植物抽出物を得る前に、植物を40℃〜80℃の温水で洗浄し、水溶性成分を除去する工程を含む方法。
- 請求項1〜3のいずれか1項に記載の方法において、原料に緑黄色野菜を使用する方法。
- 請求項1〜3のいずれか1項に記載の方法において、原料にホウレン草(Spinacia)を使用する方法。
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