TWI308152B - - Google Patents
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- Publication number
- TWI308152B TWI308152B TW092118234A TW92118234A TWI308152B TW I308152 B TWI308152 B TW I308152B TW 092118234 A TW092118234 A TW 092118234A TW 92118234 A TW92118234 A TW 92118234A TW I308152 B TWI308152 B TW I308152B
- Authority
- TW
- Taiwan
- Prior art keywords
- salt
- glycoside
- derivative
- flavonoid
- food
- Prior art date
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Description
1308152 (1) 玖、發明說明 【發明所屬之技術領域】 本發明.係關於尤其是顯示抗過敏作用之黃酮c_糖苷 之新穎衍生物或其鹽及含其之組成物。 【先前技術】 近年來,依據各種疫學調查,過敏性疾病明顯地增加 。尤其花粉症及過敏性皮膚炎之增加更爲顯著,甚至成爲 社會問題。不僅過敏原的增加,空氣污染或食品添加物及 飮食習慣變化之包圍我等之環境之變化,推測爲如此過敏 增加的原因(伊藤,綜合臨床,41: 3099 ( 1992))。過 敏性疾病之治療方法,首先除去或不攝取成爲原因之過敏 原爲基本,基於症狀程度或各疾病之發病機序,進行藥物 療法。過敏反應係依成爲其原因之免疫球蛋白及相關免疫 細胞,分爲I型至iv型之4個型。I型至m型過敏係有關 體液性抗體之免疫反應,因爲過敏反應迅速顯現,所以亦 稱爲立即型過敏,IV型過敏係與抗體無關,爲有關敏化淋 巴球之細胞性免疫性反應,亦稱爲遲緩型過敏(富岡,綜 合臨床,4 1 : 3 1 03 ( 1 992 ))。 此等過敏反應中’花粉症或異位性皮膚炎係與I型及 IV型過敏反應有關,其治療係使用抗組織胺、驗性抗過敏 劑或類固醇劑等。 - 另一方面,有關使用烏龍茶萃取物或綠茶中之掊酸表 掊兒茶酯之抗過敏劑之專利亦申請中(特開平 -5 - 1308152 (2) 10-077231、特開平 ι〇 — 175874 及特許 3023962 等)。 另外’報告指出黃酮及其糖苷具有抑制來自巨大細胞之組 織胺游離之作用或抑制免疫作用,期待其作爲過敏治療藥 之應用(Kubo M. et al,Chem. Pharm. Bull.3 2:5 05 1 ( 1 984) )。然而’幾乎所有的黃酮之顯示其效果的用量高,熱切 希望更低用量顯示效果之化合物。 【發明內容】 發明之揭示 本發明係以提供離析及確認具有抗過敏件用之物質, 以低用量可治療過敏性疾病之新穎成份及含其之組成物爲 目的。 本發明爲解決上述課題,專注於烏龍茶之抗過敏作用 ’詳細檢討烏龍茶中之抗過敏成份的結果,而發現新穎的 黃酮C -糖苷之衍生物或其鹽,具有抑制因2,4 _二硝基 氟苯(DNFB )所誘導而形成耳殼浮腫之作用及對於來自 腹腔巨大細胞之組織胺游離之抑制效果。另外,發現將此 等作爲醫藥組成物 '食品組成物或化粧材料中之有效成份 利用而完成本發明。 用以實施發明之最佳型態 如上所述之本發明亡係爲解決上述課題,專注於烏龍 茶之抗過敏作用,詳細檢討烏龍茶中之抗過敏成份的結果 ’而發現新穎的黃酮C -糖苷之衍生物或其鹽,具有對於 -6 - 1308152 (3) 2,4一二硝基氟苯(DNFB )所誘導而形成耳殼浮腫之抑 制作用及來自腹腔巨大細胞之組織胺游離之抑制效果。另 外,發現將此等作爲醫藥組成物 '食品組成物或化粧材料 中之有效成份利用而完成本發明。 因此’本發明係關於,如式(1 ) 化1
所表示之黃酮C-糖苷之衍生物或其鹽。 另外’本發明係關於,如式(2 ) 化2
所表示之黃酮C-糖苷之衍生物或其鹽。 本發明係關於至少含有1種上述之黃酮C 一糖苷之衍 -7- 1308152 (4) 生物或其鹽之過敏性疾病之預防及/或治療用 。另外,關於該過敏性疾病係至少1種選自異 、接觸性皮膚炎及花粉症之疾病之醫藥組成物 本發明係關於至少含有1種上述之黃酮C 生物(〗)或(2 )或其鹽之食品組成物。另外 關於該食物組成物係特定保健用食品、特殊營 養補助食品之飮料或其他之營養飮料、健康飮 及其他飮料之食品組成物。另外,關於該食物 心類 '麵包、麵類、大豆加工品、乳製品、蛋 製品 '油脂或調味料之食品組成物。 另外,本發明係關於至少含有1種上述之 苷之衍生物(1 )或(2 )或其鹽之化粧材料。 明係關於該化粧材料係皮膚保養品、彩粧製品 材料及沐浴材料之化粧品。 有關本發明之式(1)及/或式(2)黃酮 衍生物或其鹽係例如以茶葉爲原料,施以依加 萃取、濃縮及精製等之一般之化學分離精製手 離或層析)而可得之。 製造時所使用之茶葉係可使用Camellia si 子及/或加工其之茶葉。以使用烏龍茶爲宜。 係指以中國福建省、廣東省或台灣等爲主產地 之半醱酵茶。 溶出用之溶媒係任何水系溶媒及/或有機 以使用水系溶媒爲宜。水系溶媒係以水、乙醇 醫藥組成物 位性皮膚炎 〇 -糖苷之衍 ,本發明係 養食品及營 料、健康茶 組成物係點 加工品、煉 黃酮C一糖 另外,本發 、頭髮化粧 C—糖苷之 熱及溶媒之 段(例如分 .nensis 之葉 所謂烏龍茶 之中國原產 溶媒均可, 或甲醇等爲 1308152 (5) 第92118234號專利申請案中文說明書替換頁 民國97年8月25日修正 V ? ;>ir 宜。單獨水或水與甲醇及乙醇等之低級醇之任意混合溶液 均可。 萃取時之烏龍茶與溶劑之比率並無特別的限制,相對 於1份烏龍茶之溶媒爲2至1 000重量倍,尤其考慮萃取 操作及效率之觀點時,以5至1 0 0重量倍爲宜。
另外,溶出時之溫度,只要比溶媒之融點高,沸點低 之溫度即可,並無特別的限制,水時以10°c至100°c,乙 醇及甲醇時以1 0°C至40°c爲宜。萃取時間係以1 0秒至 24小時之範圍爲宜。 作爲化學分離精製手段,可使用作爲化學分離精製手 段之一般所使用之方法,例如可使用液一液分配、薄層層 析、吸附管柱層析、分配管柱層析、凝膠過濾管柱層析、 離子交換管柱層析、電泳或高效能液體層析等。另外,因 應需要’組合此等分離精製手段,亦可高純度精製有關本 發明之式(1)及/或式(2)之黃酮c一糖苷之衍生物或 宜鹽。
〆、J1ZL 有關本發明之式(1)及/或式(2)之黃酮C 一糖苷 之衍生物或其鹽’因爲顯示抗過敏作用,所以可使用於如 醫藥、食品及化粧品等之各種用途。作爲醫藥,式(1 ) 及/或式(2)之化合物或其鹽係因爲顯示抑制因DNFB 所誘導而形成之耳殻浮腫之作用及抑制組織胺游離之作用 ’作爲抗過敏劑’尤其可使用於異位性皮膚炎、接觸性皮 膚炎或花粉症之治療目的。作爲食品,於緩和或預防異位 性皮膚炎、接觸性皮膚炎或花粉症之症狀之目的,可作爲 -9- 1308152 (6) 食品添加物,配合於特定保健用食品、特殊營養食品、營 養補助食品及健康食品等。作爲添加對象之食品,可爲各 種食品。作爲飲料係可配合於作爲特定保健用食品、特殊 營養食品及營養補助食品之飮料或其他之營養飮料、健康 飮料、各種健康茶及其他飮料等。作爲其他食品,可舉例 如點心類、麵包、麵類、大豆加工品、乳製品 '蛋加工品 、煉製品 '油脂或調味料等。作爲化粧品,於緩和或預防 異位性皮膚炎、接觸性皮膚炎或花粉症之症狀之目的,於 皮膚保養品、粉底或彩粧製品等,可添加式(1)及/或 式(2)之化合物或其鹽。 關於醫藥’可將式(1)及/或式(2)之化合物或其 鹽,直接或以水等稀釋後,經口投予。或將其與已知之醫 藥用載體一起製劑化而調製。例如將式(1 )及/或式(2 )之化合物或其鹽作爲糖漿劑等之經口液狀製劑,或加工 成萃取物或粉末等’配合藥學上所認可之載體,作成錠劑 、膠囊劑、顆粒劑及散劑等之經口固型製劑而可投予。作 爲藥學上所認可之載體’作爲製劑材料所常用之各種有機 或無機載體物質,於固型製劑所配合之賦形劑、滑澤劑、 結合劑、崩壞劑、於液狀製劑所配合之溶劑、賦形劑、懸 濁化劑及結合劑等。另外,因應需要,亦可使用防腐劑、 抗氧化劑、著色劑及甘味劑等之製劑添加物。 .作爲賦形劑之適合例,可舉例如乳糖、白糖、D —甘 露糖醇、澱粉、結晶纖維素及輕質矽酸酐等。作爲滑澤劑 之適合例’可舉例如硬脂酸鎂、硬脂酸鈣、滑石及膠態矽 -10 - (7) l3〇8152 等’作爲結合劑之適合例’可舉例如結合纖維素 '白糖、 〇-甘露糖醇、糊精、羧丙基纖維素 '羧丙基甲基纖維素 及聚乙烯吡咯烷酮等。作爲崩壞劑之適合例,可舉例如聚 乙二醇、丙二醇、D—甘露糖醇、苯甲酸甲酯、乙醇、三 氨基甲烷、膽固醇、三乙烷胺、碳酸鈉及檸檬酸鈉等。作 爲液劑之適合例,可舉例如精製水' 醇及丙二醇等。作爲 懸濁化劑之適合例’可舉例如硬脂酸乙醇胺、十二烷基硫 酸鈉、十二烷基氨基丙酸、卵磷脂、烷基二甲基苄基氯化 銨、苄乙銨、單硬脂酸甘油酯等之界面活性劑,以及可舉 例如聚乙二醇、聚乙烯吡咯烷酮、羧甲基纖維素鈉、甲基 纖維素、羧甲基纖維素、羧乙基纖維素及羧丙基纖維素等 之親水性高分子。作爲防腐劑之適合例,可舉例如對經基 苯甲酸酯類、氯化丁醇、苄醇 '苯乙醇、3_乙醯—6 一甲 基_2,4_吡喃二酮及山梨酸等。作爲抗氧化劑之適合例 ’可舉例如亞硫酸鹽及抗壞血酸等。 作爲劑型’雖依疾病之種類或程度等而定,例如適合 於經口、非經口或鼻內投予者,可舉例如錠劑或糖衣錠、 舌下錠、明膠膠囊劑'口含錠、坐劑、乳霜劑、軟膏劑及 皮膚用凝膠劑等。另外,有效用量係依患者年齡及體重、 疾病種類及輕重度以及投予途徑而改變。單位用量係—般 以每24小時,投予!至3次爲—處理,於〇_〇〇(n至 1 00m g / kg 之 % 圍。 關於食品’可將式(1 )及/或式(2 )之化合物或其 鹽’直接或加工成萃取物或粉末等,以飲食物之形式投予 -11 - (8) 1308152 。另外,與一般所使用之飲食物材料及飮食物製造 許之載體配合’可提供作爲飲料、點心類、麵包、 大丑加工αα、乳製品、蛋加工品 '煉製品、油脂或 等。 所S胃本發明中之飲料係指烏龍茶飮料、與其他 混合之茶飲料、碳酸飮料 '果實飲料、乳酸菌飮料 飲料及豆漿’以及葡萄酒、燒酎、威士忌及淸酒等 〇 所謂本發明中之點心類係指硬式餅乾類、巧克 糖果類、口香糖類、零食點心類、油炸點心類、洋 、和式點心、冰淇淋類及果凍點心等。 大丑加工品係包含丑腐等,乳製品係包含優酷 油等’蛋加工品係包含日式煎蛋及茶碗蒸等,煉製 含魚板等。調味料係包含醬料、沙拉醬料、美乃滋 料等。此等可依常法製造。 作爲飮食物製造上所容許之載體,例如砂糖、 、果糖、異性化液糖、果寡糖 '阿斯巴甜、山梨糖 葉菊等之甘味料;紅色高麗菜色素、葡萄果皮色素 berry色素、焦糖、無花果色素、玉米色素、番紅 及胡蘿蔔素等之著色劑;果膠分解物、苯甲酸、山 對羥苯甲酸酯類及山梨酸鉀等之保存料;褐藻酸鈉 酸丙二醇酯、纖維素乙醇酸鈣及纖維素乙醇酸鈉等 ;L-抗壞血酸、生育醇、異抗壞血酸及芸香苷等 防止劑;硫酸亞鐵、亞硝酸鈉及硝酸鉀等之發色劑 上所容 麵類、 調味料 茶飲料 、運動 之酒類 力類、 生黑占心 乳及奶 品係包 及祥飯 葡萄糖 醇及甜 、e 1 d a 花色素 梨酸、 、褐藻 之糊料 之氧化 ;亞硫 -12 - 1308152 (9) 酸氫鈉及焦亞硫酸鉀等之漂白劑;丙二醇等之品質保持劑 ;L _半胱氨酸鹽酸鹽及硬脂酸乳酸鈣等之品質改良劑; 氯化銨、D-酒石酸氫鉀、碳酸銨、碳酸鉀 '碳酸氫鈉及 明礬等之膨脹劑;卵磷脂、鞘脂類 '植物性固醇、大豆皂 苷 '褐藻酸鈉、褐藻酸丙二醇酯酪蛋白鈉、甘油脂肪酸酯 、蔗糖脂肪酸酯及山梨糖醇酐脂肪酸酯等之乳化劑、軟骨 素硫酸鈉等之乳化安定劑;檸檬油、由加利油、肉桂油' 香草萃取物、柑橘油、蒜頭油' 乙醯乙酸乙酯、茴香醛、 乙基香草醛、桂皮酸、乙酸香茅醛、檸檬醛、香草醛、丁 酸丁酯及酯類等之著香料;L-抗壞血酸、L 一天門冬醯 胺、L —丙氨酸、肌醇、L一谷胺醯酸、胡蘿蔔素、生育 醇、維生素A、葉酸、檸檬酸鐵、血色素鐵及未燒成鈣等 之強化劑,過氧化苯醯、過硫酸錢及二氧化氣等之小麥改 良劑;漂白粉、過氧化氫及次氯酸等之殺菌材料;乙醯蔑 麻醇酸甲酯、脂膠樹脂、乙酸乙烯樹脂、聚異丁稀及聚丁 烯等之口香糖基礎劑、D_甘露糖醇等之粘著防止劑;酸 性焦磷酸鈉、焦磷酸鉀及焦磷酸鈉等之粘合劑;己二酸、 檸檬酸、葡糖酸、琥珀酸'D—酒石酸、乳酸及DL —鷄 果酸等之酸味料;魚介類萃取物、酵母萃取物、昆布萃取 物 '醬油 '蕃茄泥 '肉萃取物、味酣、果實泥、柴魚片、 L —褐藻酸鈉' DL —丙氨酸、L —精胺酸、L—谷胺酸鹽' 5’ —肌酸二鈉、礅檬酸三鈉、L —谷胺酸、l —谷胺酸鋼 、琥珀酸、L -酒石酸及乳酸鈉等之調味料等。 依據本發明所提供之式(1 )及/或式(2 )之化合物 -13 - 1308152 (10) 或其鹽,直接或以水等稀釋、或濃縮、或粉末化或顆粒化 ’配合已知之載體,可提供作爲氣溶膠劑、液劑、萃取物 劑、懸濁劑、乳劑、軟膏劑'糊劑 '塗抹劑及乳液劑之型 態。或因應需要,可適當地選擇已知之化粧品、醫藥部外 品及醫藥品所使用之水性成份、界面活性劑、油性成份、 可溶化劑、保濕劑、粉末成份、醇類'酸鹼調整劑、防腐 劑、氧化防止劑、增粘劑、色素、顏料及香料等而調製。 作爲皮膚外用劑’亦可製成乳液狀、凝膠狀、乳劑及軟膏 等之劑型。 本發明中所謂皮虜保養製品係指柔軟性化粧水及收斂 性化粧水等之化粧水類、滋潤乳霜'保濕乳霜及按摩乳霜 等之乳霜類、滋潤乳液、營養乳液及潔膚乳液等之乳液類 等。 所謂彩粧化粧材料係指洗面乳、皮膚洗淨劑、粉底、 眼影'腮紅及口紅等。 所謂頭髮化粧材料係使洗髮精、潤絲精、護髮劑、髮 霜、整髮劑、養髮液、養髮劑及生髮劑等。所謂沐浴材料 係指潤膚浴油、沐浴鹽及沐浴乳等^ 關於食品或化粧材料’其配合量並無特別的限制,一 般換算成乾燥固形成份爲0.0001至10〇重量%,以〇 〇〇1 至50重量%爲宜。 【實施方式】 依實驗例及實施例更詳細地說明本發明,但本發明之 -14 - 1308152 (11) 丨 範圍並不局限於此。 實施例 實施例1 :製造例 將5.0kg之中國福建省產之烏龍茶,使用100L之熱 水萃取,放冷後,供予充塡30L之合成吸附劑(DIAION HP — 2 1,二菱化學社製)之管柱,再將非吸附部份供予 充塡30L之合成吸著劑(DIAION HP — 20,二菱化學社製 )之管柱,逐次提升乙醇對於水之含量溶出(分別爲60L ),而得4個分離部份〔乙醇濃度=0% ( OHF3N ) 、20 % ( OHF4N ) ' 40% ( OHF5N ) ' 99.5% ( OHF6N )〕。 將該4個分離部份中,將抑制因DNFB所誘導而形成 耳殼浮腫之作用最強之OHF3N分離部份,濃縮及冷凍乾 燥(5 1 7g ),再進行水一正丁醇之逆流分佈(n = 7 ),將 移動次數7次之部份之減壓濃縮物(2. lg ),供予充塡 Sephadex LH-20 ( Pharmacia Biotech |± )之管柱,以甲 醇溶出,收集Kd (平衡分配係數)値爲1.9至2.2之分離 部份。該減壓濃縮物以HPLC分離。管柱爲SENSHU PAK DIOL-1251 ( SENSHU 化學社製,4.6x250mm),移動相 係使用己烷:甲醇:四氫呋喃=5 0 : 3 5 : 1 5之溶媒,以 流速1ml / min ( 30°C )溶出,分別取出保留時間爲5.8 分鐘所溶出之高峰(UV2 80nm )。減壓濃縮後,以使用 YMC-Pack ODS-A ( YMC 社製,4.6x150mm)之 HPLC 精 製。分別取得後,以減壓濃縮而得9 8 0 // g之淡黃色粉末 (12) 1308152 依據NMR及MS等之光譜及X射線分析,進行構造 解析的結果(表1及表2),確認本化合物係式(1 )之 異牡荆素(isovitexin)(參考圖3)之第7位置之OH及糖 鏈之第1位之OH爲分子內脫水聚合之化合物〔化合物( 1 ) ) ° -16 - (13) 1308152 表1 依據化合物(1 )之1H— NMR及13C- NMR決定構造 部份 配糖基 糖 C Η C Η 2 168.1 1 " 74.6 5.2 1 d 3 102.9 6.58s 2" 89.0 4.67t 4 184.8 3 " 73.9 3.98t 5 168.7 4 " 69.8 3.58t 6 112.6 5 " 80.6 3.3 3m 7 166.5 6" 63.5 3.62m,3.83m 8 91.8 6.64s 9 161.2 10 107.9 Γ 119.3 2' 1 3 0.2 7.8 0d 3' 1 1 9.3 6.8 0d 4' 168.1 5, 1 1 9.3 6.8 0d 6'_1 3 0.2 7.80d_ 依據化合物(1)之1H—NMR及]3C_NMR決定構造( ppm.in CD3OD) 17- 1308152 (14) ΎΙ yf ¢-.. 表2 f衣據化合物(1 )之X射線分析決定構造 妹曰播 '、生 示口曰日傅迎 0.10x0.05x0.20mm 晶格參數 a- 10.811 (6) A b = 26.270 ( 6 ) A c = 6.950 ( 1 ) A v= 1961.0 ( 9) A 3 Space Group P2,2i2! Z value 4 D c a 1 c 1.40 3 g/cm3 R value 0.078
化合物(1 )之精製過程中之OHF3N分離部份(517g ),進行水一正丁醇之逆流分佈(n = 7),將移動次數7 次之部份之減壓濃縮物(2.1 g ),供予充塡Sephadex LH-20 (Pharmacia Biotech社製)之管柱,以甲醇溶出,收集 Kd (平衡分配係數)値爲1.6至1.9之分離部份。該減壓 濃縮物以HPLC分離。管柱爲SENSHU PAK DIOL-1251 ( SENSHU化學社製,4.6 x25 0mm ),移動相係使用己烷: 甲醇:四氫呋喃=5 0 : 3 5 : 1 5之溶媒,以流速1ml/ min (3 (TC )溶出,分別取出保留時間爲5 . 8時所溶出之高峰 (UV2 80nm )。減壓濃縮後,以使用 YMC-Pack 〇DS-A( YMC社製,4.6x150mm)之HPLC精製。分別取出後,以 減壓濃縮而得1 47 // g之淡黃色粉末。 -18- (15) 1308152 依據NMR及MS等之光譜及X射線分析,進行構造 解析的結果(表3及表4 ),確認本化合物係式(2 )之 牡荆素(vi t ex in)(參考圖3)之第7位置之OH及糖鏈之 第1位之OH爲分子內脫水聚合之化合物〔化合物(2 ) -19 - (16) 1308152 表3 依據化合物(2 )之1Η — NMR及I3C — NMR決定構造 部份 配糖基 糖 C Η C H 2 166.8 1 " 75.1 5,47d 3 104.3 6.66s 2" 89.1 4.78t 4 184.4 3 " 73.8 4.05t 5 166.2 4" 69.8 3,62t 6 96.3 0.39s 5 " 80.5 3.47m 7 168.9 6" 63.4 3.65m,3.87m 8 108.5 9 15 5.1 10 106.7 1 ' 125.0 2' 130.2 7.90d 3, 118.0 6.93d 4' 164.9 5 ' 118.0 6.93d 6, 130.2 7.90 依據化合物(2)之1H—NMR及13C_NMR決定構造( ppm.in CD3OD) -20- (17) 1308152 表4 依據化合物(2 )之X射線分析決定構造 I吉晶構造 晶格參數
0.03x0.10x0.3 0mm a = 9.785 ( 2) A
b= 1 9.700 ( 5 ) A c= 4.93 57 ( 8 ) A
v= 950.1 ( 3 ) A
Space Group Z value D c a 1 c R value P2, 2 1 .5 60g/cm3 0.058 實施例1 :對於小鼠耳殻接觸性皮膚炎之抑制效果 使用動物係購自日本CREA (株)之7週大之 小鼠,預備飼育1週後,用於實驗。將實驗例1戶J 黃色粉末〔化合物(1)〕懸濁於0.5%之羧甲基_ /0.01N 鹽酸,投予量爲 〇.2、1.0 及 5.0#g/kg 濃度者,調製成投予量爲10ml/kg。小鼠係每1 ,於背部皮下注射100/il之1%之2,4 —二硝1 DNFB)之乙醇溶液,以5天使敏化成立。於第6 耳殻上塗佈1%之DNFB橄欖油溶液,引起耳殼g 膚炎。24小時後’將雨耳以直徑,χ 之穿孔器穿 定重量。化合物(】)係初次敏化的前1天至引起 曰之7天期間’進行連續經口投予。作爲對照組, ICR系 得到之 ;維素鈉 之3種 組6隻 :氟苯( 天,右 :觸性皮 _孔,測 浮腫當 則進行 -21 - 1308152 (18) 投予0.5%之羧甲基纖維素鈉/0.01N鹽酸。實驗 表示相對於左耳殼之右耳殼之浮腫率之平均値及標 ,組間之有意差檢測係使用S t u d e n t' s t _ t e s t。其結 1所示。由圖1顯示,與0 · 5 %之羧甲基纖維素鈉/ 鹽酸投予之對照組相比較,於1 .0及5.0 # g/ kg 物(1 )之投予組中,因DNFB之浮腫有意義地受 實施例2 :對於小鼠耳殼接觸性皮膚炎之抑制效果 使用動物係購自日本CREA (株)之7週大之 小鼠,預備飼育1週後,用於實驗。將實驗例1所 黃色粉末〔化合物(2 )〕懸濁於0 · 5 %之羧甲基纖 /0.01N鹽酸,投予量爲1.0、10及l〇〇;/g/kg之 度者’調製成投予量爲1 0 m 1 / k g。小鼠係每1組 於背部皮下注射之1%之2,4一二硝基 DNFB)之乙醇溶液’以5天使敏化成立。於第6 耳殻上塗佈1%之DNFB橄欖油溶液,引起耳殼接 膚炎。24小時後’將兩耳以直徑8mm之穿孔器穿 定重量。化合物(2 )係初次敏化的前1天至引起 曰之7天期間’進行連續經口投予。作爲對照組, 投予0.5%之之羧甲基纖維素鈉/ 0·01Ν鹽酸。實 係表示相對於左耳殼之右耳殼之浮腫率之平均値及 差,組間之有意差檢測係使用S t u d e nt's t-test。其 圖2所示。由圖2顯示’與〇·5%之之羧甲基纖維 結果係 準誤差 果如圖 7 0.0 1Ν 之化合 到抑制 ICR系 得到之 維素鈉 3種濃 6隻, 氟苯( 天,右 觸性皮 孔,測 浮腫當 則進行 驗結果 標準誤 結果如 素鈉/ -22- 1308152 (19) 0.01N鹽酸投予之對照組相比較,於1〇〇 v g/ kg之化合 物(2 )之投予組中,因DNfb之浮腫有意義地受到抑制 實施例3 :對於來自腹腔巨大細胞之游離組織胺之抑制效 果 使用動物係購自曰本CREA (株)之7週大之Wister 系大鼠’預備飼育1週後,用於實驗。將Wister系大鼠 於乙醚麻醉下,斷頭致死後,於腹腔內注入Tyrode液。 以常用方法離析出巨大細胞,懸濁於含有〇 . 1 %之牛血淸 球蛋白(BSA)之Tyrode液,使之成爲1至3xl08cell/ m 1 ’而調製成巨大細胞浮游液。將溶解於5 〇 %之甲醇之 化合物(1 )或化合物(2 ),加入上述之巨大細胞浮游液 ,於37C下’進fj培養5分鐘。之後,加入compound48 / 8 0 ’於3 7 °C下’進行培養1 0分鐘,冰冷後,將離心分 離之上清液,依據Onda等人之方法〔J. Med. Sci.,27, 93-97(1978)〕,依據使用鄰苯二甲醛(OPA)之柱後法之 高效能液體層析儀,測定游離組織胺量。實驗結果係以相 對於僅以溶媒處理時之游離組織胺量之以試樣處理時之游 離組織胺之抑制率表示。其結果如表5所示。 -23- 1308152 (20) 表5 抑制組織胺游.離之試驗結果 試料 濃度(# g/ml) 游離組織胺抑制率 化合物(1) 5.0 ----- 62.3 化合物(2 ) 50.0 5 1.2 實施例2 :類固醇劑及其他類黃酮效果的比較 使用與實驗例1及實驗例2相同的方法,將皮質類固 醇製劑(corticosteroids)及數種類黃酮(圖3)之抑制因 DNFB所誘發而形成耳殼浮腫之作用,與化合物(1)及 化合物(2 )比較。實驗結果係以抑制50%之因DNFB所 誘發而形成耳殼浮腫之投予量表示。其結果如表6所示。 投予化合物(1 )及化合物(2 )時,與皮質類固醇製 劑或其他類黃酮相比較,顯示以極少量即具有抑制耳殼浮 腫形成之作用。 -24 - 1308152 (21) 表6 殻浮腫形成之作用之評估結果 抑制5 0 %之耳殼浮腫之投予量 (m g / k ε Ρ . 0 . Ί 化合物(1 ) 0.05 化合物(2) 0.17 Dexamethasone 1 .5 序菜素 247 牡荆素 103 Rhamnosyl viiexin 146 槲黃素 265 芸香苷 123
實施例3 :錠劑之製造例 1 5 0 g之實施例1所得之化合物(1 )與同量之乳糖及 5 g之硬脂酸鎂混合,將此混合物以單發式打錠機打錠, 製造成直徑爲l〇mm,重量爲3 00mg之錠劑。 實施例4 :顆粒劑之製造例 將實施例2所得之錠劑粉碎、製粒及篩別,而得2 〇 至5 0網目之顆粒劑。 實施例5 :糖飴之製造例 使用下述之材料’依據常法製造。 -25- 1308152 (22) 山梨糖醇粉末 99.lg 香料 〇.2g 化合物(1 ) 0.05g 山梨糖醇晶種 0.05g 全量 1 〇〇g 實施例6: 口香糖之製造例
使用下述之材料1 |依據常法製造。 膠基質 2〇g 碳酸鈣 2g 蛇菊苷 〇.lg 化合物(1 ) 0.05g 乳糖 76.85g 香料 1 g 全量 1 〇〇g 實施例7 :橘子汁之製造例 使用下述之材料, '依據常法製造 冷凍濃縮橘子汁 5g 果糖葡萄糖液糖 log 檸檬酸 〇.2g L -抗壞血酸 〇.〇2g 化合物(1 ) 0.05g 香料 〇.2g -26- 1308152 (23) 色素 O.lg 水 剩餘量 全量 l〇〇g 實施例8 :果凍點心之製造例 使用下述之材料,依據常法製造。 砂糖 500g 麥芽糖 5 00g 果膠 13g 檸檬酸 4 g 檸檬酸鈉 1 . 5 g 香料 lg 食用色素 〇.2g 化合物(1 ) 0 · 5 g 於13g之果膠中,混合20g的砂糖後,加入3 3 0ml的 水,溶解至不成顆粒狀。再加入檸檬酸及檸檬酸鈉,使其 沸騰。加入麥芽糖於其中,加熱至1 〇〇°C後,加入剩餘的 砂糖,升溫至1 〇 9 °C。靜置數分鐘後,加入化合物(1 ) 、香料及色素後攪拌,充塡於澱粉模型,於5 (TC以下, 乾燥1 〇小時以上,而得果凍點心。 實施例9 :魚板之製造例 使用下述之材料,依據常法製造。 -27 - 1308152 (24) 助宗鳕魚漿 l〇〇g 食鹽 20g 調味料 2g 蛋白 l〇g 化合物(1 ) 〇.5g 於S u k e s 〇 u _魚漿中,加入食鹽、調味料及化合物( 1 )混煉及熟化後成型,以約90至95 °C預先加熱之蒸籠 中蒸煮,之後放冷而得魚板。 實施例1 〇 :滋潤乳霜之製造例 使用下述之材料,依據常法製造。 蜜蠟 2.0g 硬脂醇 5.0g 硬脂酸 8.0g 角鯊烷 10.〇g 自乳化型丙二醇 3.0g 硬脂酸酯 聚環氧乙烷十六烷醚 l〇.〇g 香料 〇.5g 防腐劑 適量 氧化防腐劑 適量 丙二醇 7.8 g 甘油 4.0 g -28 - 1308152 (25) 透明質酸鈉 〇.15g 化合物(1 ) 0.05g 三乙烷胺 1 -〇g 精製水 57.5g 實施例11 :洗髮精之製造例 使用下述之材料’ 依據常法製造。 烷基醚硫酸鈉 1 6.0g 月桂酸二乙醇醯胺 4.0g 丙二醇 1.95g 防腐劑、色素及香料 適量 氧化防腐劑 適量 化合物(1 ) 〇.〇5g 精製水 78.0g 產業上利用性 如上述之說明’依據本發明,發現烏龍茶中所含有之 新穎黃酮C一糖苷之衍生物或其鹽係具有顯著的抗過敏作 用’可提供以此等爲有效成份之醫藥組成物、食品組成物 或化粧材料。 【圖式簡單說明】 圖〗係表示於實驗例1所進行之以本發明之化合物( 1)之投予量成爲0.2' 1.0及5.0/zg/kg之3種濃度者與 -29 - (26) 1308152 作爲對照組之投予0.5 %之羧甲基纖維素鈉/ 0.0 1 N鹽酸時 ’對於小鼠耳殼接觸性皮膚炎之抑制效果之差異圖。 圖2係表示於實驗例2所進行之以本發明之化合物( 2)之投予量成爲1.0、10及l〇〇#g/kg之3種濃度者與 作爲對照組之投予0.5 %之羧甲基纖維素鈉/ 0 · 0 1 N鹽酸時 ’對於小鼠耳殻接觸性皮膚炎之抑制效果之差異圖。 圖3係表示類黃酮之構造。 -30 -
Claims (1)
- Λ1308152 Ύ1 K 拾、申請專利範圍 第92 1 1 8234號專利申請案 中文申請專利範圍修正本 民國97年8月25日修正 1. 一種黃酮C-糖苷之衍生物或其鹽,其特徵爲, 如式(1 )所示hoh2c 〇2. 一種黃酮C -糖苷之衍生物或其鹽,其特徵爲, 如式(2 )所示 化23 . —種過敏性疾病之預防及/或治療用醫藥組成物 ,其特徵爲,含有至少1種如申請專利範圍第1項或第2 1308152項之黃酮C一糖苷之衍生物或其鹽。 4.如申請專利範圍第3項之醫藥組成物,其中該過 敏性疾病係至少一種選自異位性皮膚炎、接觸性皮膚炎及 花粉症之疾病。 5 · —種食品組成物,其特徵爲,含有至少一種如申 專利fe圍第1項或第2項之黃酮c_糖苷之衍生物或其 鹽爲抗過敏性成份。 6 ·如申請專利範圍第5項之食品組成物,該食品組 成物係作爲特定保健用食品、特殊營養食品及營養補助食 品之飲料或其他之營養飲料、健康飮料、健康茶及其他飲 料。 7·如申請專利範圍第5項之食品組成物,該食品組 成物係點心類、麵包' S類、大豆加工品、乳製品、蛋加 工品、煉製品、油脂或調味料。 8. —種化粧材料,其特徵爲,含有至少一種如申請 專利範圍第1項或第2項之黃酮c_糖苷之衍生物或其鹽 爲抗過敏性成份。 9 ·如申請專利範圍第8項之化粧材料,該化粧材料 係皮膚保養品、彩粧製品、頭髮化粧材料及沐浴材料。 1 0 ·—種至少一種如申請專利範圍第1項或第2項之黃 酮C —糖苷之衍生物或其鹽之使用,其特徵爲用於製備具 有抗過敏性作用之醫藥組成物。 1 1 . 一種至少一種如申請專利範圍第1項或第2項之黃 酮0—糖苷之衍生物或其鹽之使用,其特徵爲用於製備具 -2- 1308152 有抗過敏性作用之食品組成物。 12. —種至少一種如申請專利範圍第1項或第2項之黃 酮C 一糖苷之衍生物或其鹽之使用,其特徵爲用於製備具 有抗過敏性作用之化粧材料。
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WO2010076879A1 (ja) | 2009-01-03 | 2010-07-08 | 静岡県公立大学法人 | 硫酸化c-配糖体及びその単離方法並びに合成方法 |
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CA2491027A1 (en) | 2004-01-15 |
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WO2004005296A1 (ja) | 2004-01-15 |
EP1533313A4 (en) | 2007-01-24 |
DE60321924D1 (de) | 2008-08-14 |
JP4549009B2 (ja) | 2010-09-22 |
KR20050016934A (ko) | 2005-02-21 |
US20050288237A1 (en) | 2005-12-29 |
EP1533313A1 (en) | 2005-05-25 |
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