TWI227661B - Water-soluble bean-based extracts - Google Patents
Water-soluble bean-based extracts Download PDFInfo
- Publication number
- TWI227661B TWI227661B TW089101038A TW89101038A TWI227661B TW I227661 B TWI227661 B TW I227661B TW 089101038 A TW089101038 A TW 089101038A TW 89101038 A TW89101038 A TW 89101038A TW I227661 B TWI227661 B TW I227661B
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- Taiwan
- Prior art keywords
- water
- extract
- soluble
- patent application
- isoflavone
- Prior art date
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Classifications
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- 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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- A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
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- A23L11/07—Soya beans, e.g. oil-extracted soya bean flakes
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- A—HUMAN NECESSITIES
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/20—Ingredients acting on or related to the structure
- A23V2200/218—Coagulant
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23V2250/00—Food ingredients
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- A23V2300/00—Processes
- A23V2300/14—Extraction
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
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Description
1227661 (2004年4月修正) 玖、發明說明: 發明所屬之技術領域 營養研究之-最新和最關心之領域包括所謂植物化學 品之植物成分。植物化學品如異黃酮和其衍生物只見於植 物,雖不歸類爲營養品,但深深影響我們之健康(H Bidlack等著:植物化學品,Techn〇mic出版社1998)。· 先前技術 植物化學品之發現引起營養上新時代之曙光。見於大 五等丑類之植物化學品特別重要。豆類和其製品,例如大 丑和大豆製品提供降低如癌等多數慢性疾病被害之特殊管 道(農業食品化學雜誌,42 1666(1994);和43, 1 184(1995)。 近年之研究顯示,每日一餐大豆食品足於獲得這些食品化 冬印之好處(M· Messina等著:單純大豆和我們之健康,Νγ, 花園城市公園Avery出版社出版,1994)。 但大豆食物因其臭味、粗質等而多數人不願食用,其 解決方式4以大豆異黃調爲飲食補助品,但不幸因其水 '夺|生低’故大豆異黃酮和其衍生物仍未被利用(R. Elkinsa 著·金雀異黃s同苷素,猶太州,快樂谷,Woodland出版社 出版,1998)。 發明内容 本發明之特徵爲一種水可溶豆類萃取物,含有一種以 上如下式異黃_衍生物 1227661 (2004年4月修正)
式中Rl爲氫或經基,R2爲氫或甲氧基,R3爲氫或C0如r4 爲甲基或叛甲基。此水可溶豆類萃取物乾燥型時含有約 約50重量%異黃酮衍生物, 於約25 c水中之溶解度爲約1〇〜 約1 000mg/ml。存在於水可唆5布茲 J /合旦類卒取物之異黃酮之例包括 大豆異黃酮苷、金雀異黃 ,^ ^ /、汽_苷、大旦苷、6”一〇—乙醯基大豆 異黃酮苷、6" -0-乙醯基全名s廿 丞金雀異頁酮苷、6,,—〇—乙醯基大豆 苷、6”-〇-丙二醯基大豆異音 田廿 、酮苷、6 ―0 一丙二元醯基金雀 異頁酮苷或6π-0-丙二醯基大豆苷。 本發明之水可溶豆類萃 私; ^ ^以上異黃酮衍生 物,例如-種異黃_普,與豆 地提高水溶性。 -他成分m合而意外 本發明之其他特徵爲水可溶豆類萃取物之製法,包括 將粉化粗製五類萃取物與 成縣浮液後,Λ劫 加熱、添加凝集劑而形 JL風味佳,#作 八π ,,侍水可溶豆類萃取物, ”風味佳,*作任何食品之成分時, 性能而可與如牛、# 、且之組成物和 干礼、余、清涼飲料、果汗丄 穀物、水、啤洒H, 、咖啡、調味料、 千涵、脆餅、口香糖、巧券六 $見力或湯等食品配合。 1227661 本發明之其他特徵和優 明白。 實施方式 (2004年4月修正) 點可由如下文和申請專利範圍 本發明爲有關一 下式異黃酮衍生物 種水可溶豆類萃取物 含有一以上如
式中R1爲氫或經基,R2爲氫或甲氧基,R3爲氯或c〇 — R4, R4 爲甲基缝甲基。存在於水可溶豆類萃取物之異黃酮之例 匕括大豆異兴酮苷、金雀異黃酮苷、大豆苷U—乙醯基 大豆異黃酮苷、6” +乙醯基金雀異黃酮苷、6”—0—乙醯基 大旦苷、6"-〇-丙二醯基大豆異黃酮苷、6,,—〇-丙二醯基金 雀異黃㈣或6” +丙二醯基大豆苦。如大豆異黃_芽、金 雀異κ酮芽素等異黃_普於胃腸被吸收而由人小腸内生産 鼠李糖普酶、夕Μ葡萄糖謂、内万葡萄醛糖鶴之微生 物經配糖基代謝爲異黃酮(Bi〇1. pharm. BuU,22( 1998);
Biol. Pharm. Bull, 17, 1369(1994); Arch. Pharm. Res·, 21, 17(1998) 〇 1227661 (2004年4月修正) 、本發明之水可溶豆類萃取物增進水溶性,用於食品時 增進異黃嗣衍生物之生理吸收。例如,金雀異㈣之溶解 ;C甲醇時約5mg/ml,水時約img/ml,而含有約1 異 黃酮衍生物之本發明水可溶豆類萃取物之水溶性爲約 300mg/ml。一般而t,本發明之水可溶豆類萃取物增加異 黃酮衍生物之溶解度約_。乾燥形態時,含有約.約5〇 重量%異黃酮衍生物,於約25t水溶性爲約1〇一約 l〇〇〇mg/ml ;宜含有約10_約20重量%異黃酮衍生物水溶性 爲約30-約30〇mg/ml ;尤宜含有約1〇'約2〇重量%異黃酮衍生 物,水溶性爲約50-約200mg/ml。當然,異黃酮衍生物之重 量%影響水可溶豆類萃取物之總溶解度。例如,異黃綱衍生 物較高重量%之萃取物之總溶解度低於異黃_衍生物較低 重量%之萃取物。 任何豆類皆可用以製造本發明之水可溶豆類萃取物, 不限於大豆、綠豆、黑豆、敏豆,尤宜大豆。通常可用二 種不同型大豆,例如食用豆和製油用豆,惟宜製油用豆, 蓋蛋白質含有量比食用豆少。-般’製油用豆先除油來製 成加工豆。此除油法可參見K. S· Liu著:大豆、技術和利 用,馬利蘭州,蓋滋堡,Aspen出版社出版,1999。 本發明水可溶豆類萃取物之製法包括混合約卜約“重 量份豆粉粗萃取物和約100重量份熱或冷水。豆粉粗萃取物 可由豆粉用約50-90%醇水溶液或1〇〇%有機溶劑,如乙醇、 甲酵或乙猜卒取來製造。丑粉粗卒取物之實例爲大—胚 芽,代表約1重量%大豆,仍比剩餘之大豆部分含較高異黃 1227661 (2004年4月修正) _濃度’南约6倍,參見K · S · L i u著··大豆、技術和利用, 馬利蘭州,蓋滋堡,Aspen出版社出版,1999。豆粉粗萃取 物如大豆胚芽可以SoyLi f el 50和SoyLi f e25購自美國 Schousten公司。豆粉粗萃取物則以N0VAS0Y購自美國 Archar Daniels Midland公司。 次將此水和豆粉粗萃取物之混合物加熱約6〇_10〇°c約 10 -12 0分後,每1 〇 〇重量份水添加約2 · 〇重量份凝集劑而形 成懸浮液,再加熱約30-100°C約1-120分後,以過濾或離心 來收集上清液,得增進溶解度之水可溶豆類萃取物。懸浮 液或上清液之pH可添加酸或域調節以免使異黃酮衍生物沈 澱。一般,pH調爲約6. 〇。 所得上清液可脫色來脫任何非所望顏色。脫色方法藉 助Ni觸媒之氫化和用於製造大豆油之漂白法。脫色法可參 見K· S· Liu著:大豆、技術和利用,馬利蘭州,蓋滋堡, Aspen出版社出版,1999,和ρ· j. Wan著:油脂技術,伊 利諾州,香擯,A0CS出版社出版。此上清液也可用包括分 子瘵餾或蒸發等周知之蒸餾系統來濃縮。分子蒸餾系統之 貫例爲購自美國 351N· Dekora Woods Blv. Saukville, WI53_,HOPE公司之Wiped-Film StiU。此上清液可用如 凍幹或噴幹等任何周知之乾燥方法乾燥(upS5,882, 7i7)。 本發明之水可溶豆類萃取物可由分批法或流動法,即 連項萃取和過濾法來製造。一般,用流動法以維持合理之 製造成本。 爲提高異黃酮苷之溶解度,於100重量%水添加約 10 1227661 (2004年4月修正) 〇· 0 01-3· 0重量%凝集劑,如氯化鈣、硫酸鈣、氯化鎂、硫 酸鎮、任何有機或無機酸(例如檸檬酸、富馬酸、乳酸、頻 果酸、酒石酸、硫酸、磷酸或鹽酸)、糖精、葡萄醛糖— 内酯,和木瓜酶。製造此萃取物時,添加凝集劑藉單純交 連或改質來形成豆蛋白或多醣之不溶性凝集物。凝集劑之 濃度直接影響萃取物中豆蛋白或多糖之量。例如,凝集劑 Ϊ越多,越形成不溶之凝集物。此效果容許萃取物中水溶 I*生蛋白和夕醣之總量之控制,和異黃酮衍生物之溶解度。 凝集劑之添加量藉測定所得豆類萃取物之脂肪、蛋白質和 …機自文a里來决疋。一般,添加足量凝集劑來生成約1 %以 下脂肪、約卜5%蛋白質、約〇·〇1—3·、約〇〇1一_和約 0.01-3%任何酸。水可溶豆類萃取物中這些之量可由任何周 知:分析法,例如食物藥品管理局⑽A)推薦之如下分析: 決定。-般,於萃取物添加㈣· 3重量%檸檬酸。若凝 添加太多’則由萃取物共析出水溶性豆蛋白質、多聽或1 黃嗣!:生物’而降低萃取物中異黃_衍生物之濃度或溶解 ::右破集劑添加太少,則豆混合物形成膠狀而難 離水可溶豆類萃取物。 77 本發明之水可溶豆類萃取物可以乾燥或濕型 品。食品可爲固體、膏狀或液體’如牛乳、茶飲 果汁、咖啡、調味料、榖铷,, I厅、飲枓、 ㈣毅物、水、啤酒、脆餅、 巧克力或湯。 货糖、 本發明之水可溶豆類萃取物也可由大麥、米、爽 其他穀物之共萃取物。例甘 夕牙專 種以上之其他穀物與豆類可 1227661 (2004年4月修正) 由上述方法製成本發明之水可溶豆類萃取物。此外,水可 溶豆類萃取物可用電解質、香料、保存劑和其他添加劑(例 如維生素補充劑和麥芽糊精)來增強。保存劑之實例有如抗 壞血酸和五倍子酸丙脂,電解質有如硫酸鎂和KC 1。 下面舉例詳述本發明,但本發明不限於此。所有包括 專利公報之引用刊物皆列入參考。 實施例1_ 用約90%乙醇水溶液萃取之豆粉粗萃取物1公斤(購自 美國Schousten公司入之SoyLi f el 50中加3公升70°C熱水, 於90°C30分和5(TC30分之攪拌後,於5〇tl〇,〇〇〇Xg離心粗 分離殘滓和溶液。傾析後,於上清液添加食品添加劑級氣 化鈣6克(約〇·〇2Μ),於3〇。〇攪拌3〇分後,上清液濾經丄“爪 微濾器,得黃色溶液2· 5公升。將此移入5-L玻璃燒瓶,有 觸媒量(約3克)5%pd/c存在之1〇大氣壓氫下氫化5小時。將 此脫色混合物濾經〇· 2 # m微濾器,得清澄水可溶豆類萃取 物溶液2· 3公升。 將此水可溶豆類萃取物溶液用HpLC特徵化。脱系購 自Waters么司之C18逆相柱ΐ5〇χ4· 6mm對稱掩蔽RP18,於30 °C依梯度溶析法,用15 —40%乙腈水溶液和〇·1%三氟乙酸以 lml/分溶出20分。HPLC測定器設定爲254nm。圖1表示實例1 水可溶豆類萃取物中主成分之肌⑽·其各峰、滯留時間、 峰面積和面積%如下表1。萃取物之若干成分由比較未知成 刀之π留時間和於同一實驗條件下HpLc分析之已知異黃酮 12 661 替 (2004年4月修正) <丨帶留時間來鑒定。 水可溶豆類萃取物溶液也測定萃取物成分之相對量來 特徵化。萃取物之樣品送美國,奥列岡州,波多蘭市,食 品實驗公司依FDA推薦之方法分析,結果含有<〇· 1 %脂肪、 5%蛋白質、65%碳水化物(多醣)、2〇%異黃酮、8%礦物質和 1%水分。 '
13 1227661 (2004年4月修正) 表1.例1中可溶性黃豆産物之HPLC分析 峰 滯留時間(分) 峰面積 面積% 化合物 1 6. 940 56. 95 0. 35 未測 2 7. 231 85. 42 0. 53 未測 3 7. 661 164.09 1. 02 未測 4 8. 090 5129·91 31. 85 大豆異黃酮苷 5 8. 507 2722.58 16. 90 大豆苷 6 10. 376 19. 68 0. 12 未測 7 10. 652 23. 89 0. 15 未測 8 11. 069 34. 82 0. 22 未測 9 11. 685 367.98 2. 28 未測 10 11.990 1378.49 8. 56 金雀異黃酮苷 11 12. 766 75. 19 0. 47 丙二醯大豆異黃酮苷 12 13. 048 52. 95 0. 33 丙二醯大豆苷 13 13. 461 3038. 54 18. 86 乙醯大豆異黃酮苷 14 13. 771 1421.88 8. 83 乙醯大豆苷素 15 15. 723 33. 08 0. 21 未測 16 15. 942 43. 63 0. 27 未測 17 17. 265 58. 45 0. 36 未測 18 17. 737 867.85 5. 39 乙醯大豆苷 19 18. 236 288· 12 1. 79 大豆苷素 20 18. 822 196.99 1. 22 大豆異黃酮素 21 25. 657 47. 89 0. 30 金雀異着酮素 合計 16108.41 100.00 14 1227661 (2004年4月修正) 實施例2 用約90%乙醇水溶液萃取之豆粉粗萃取物1公斤(購自 美國Schousten公司入之s〇yLifel50中加27公升70°C熱 水,於90°C攪拌15分後,注入90克檸檬酸水溶液公升。於 9 0°C攪拌15分後,真空濾經矽藻土床濾紙。濾液爲淡黃色 清澄溶液27公升。此用碳酸鉀5〇克調爲ρΗ6·〇真空濾經〇45 // m穴濾器(毫孔公司)除菌純化後,於7〇°c 2〇匪氣壓用2英 寸之Wiped-Film Still(HOPE科學公司)濃縮,得淡黃色水 可溶豆類萃取物溶18公升。 實施例3 仿實施例1得水可溶豆類萃取物溶液2公升後,用 Bertis公司製造之凍幹機於—85〇c 1〇_氣壓凍幹2日,得35〇 克淡黃色幹餅。此含有7〇克異黃酮衍生物,溶解度約 2〇〇mg/ml。溶解度系將1克乾燥萃取物於25°C純水lml攪拌5 分’若未完全溶解(視覺檢查),追加lml水而於25它攪拌5 分。次再視覺檢查是否完全溶解,若不,再追加lml水而於 25 e擾拌5分’如此至視覺檢查完全溶解爲止。 其他貫施例 本文揭示之所有特點可作任何配合。本文揭示之各特 可取代以具有同樣、相當或類似目的之別種特點。故除 了特別記述之外,各鬥千夕牲μ / ’、 h各開不之特點只爲了一系列相當或類似 15 1227661 (2004年4月修正) 特點之例。 由上所述’業者不難由本發明之重要特點,不離其精 神和範圍可作本發明之種種變化和修飾來適合不同用途和 條件。這些也包括於申請專利範圍。
k之水可溶豆類萃& 貝卒取物中主成分之HPLC 圖示簡單說明 圖1爲例1製 圖0
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Claims (1)
122 122 拾、申請專利範圍 ;r0修正I 補充i (2004年9月修正) S同衍生物 種水可溶豆類萃取物,含有一 種以上如下式異黃
式中Ri為氫或經基, 為甲基或羧甲基,此 重量份異黃酮衍生物 fflg/ml 〇 匕為氫或甲氧基,r3為氫或C〇 —r4,r4 水可溶豆類萃取物乾燥型時含有5 - 5 0 ’於25°C水中之溶解度為50 — 500 一 2·如申請專利範圍第1項之水可溶豆類萃取物,其中 且類萃取物基於大豆、綠豆、黑豆、或敏豆。 3.如申明專利範圍第1項之水可溶豆類萃取物,其中 豆類萃取物基於大豆。 4·如申請專利範圍第丨項之水可溶豆類萃取物,其中 良可溶豆類萃取物乾燥型時含有1 〇 — 2 〇重量份異黃酮衍生 物’於25°C水中之溶解度為50-30〇mg/ml。 17 1227661 (2004年9月修正) 5.如申吻專利範圍第1項之水可溶豆類萃取物,其中 :可溶豆類萃取物乾燥型時含有1〇_2〇重量份異黃酮衍生 物,於饥水中之溶解度為50-20—。 6.如申明專利靶圍第j項之水可溶豆類萃取物其中 二黃酮衍生物為大豆異黃酮*、金雀異黃酮普、大豆普、 〜〇-乙絲大豆異黃㈣、6,,1乙醯基金雀異黃崎、 0-乙醯基大豆苷、6"_〇_丙二醯基大豆異黃酮苷、6" + 二醯基金雀異黃酮普或6„♦丙二酿基大豆苦。 一乂如申請專利範圍第6項之水可溶豆類萃取物,其中 足類萃取物基於大豆。 8 ·如申請專利範圍第馆 . 弟項之水可溶豆類萃取物,其中 物可溶豆類萃取物乾燥料含有1g_2g重量份異黃嗣衍生 ’於25C水中之溶解度為5()侧mg/^。 9.如中請專利範圍第6項之水可溶豆類萃取物,其中 物可溶豆類萃取物乾燥型時含有MO重量%異黃嗣衍生 ’於25C水中之溶解度為50-200mg/na。 可溶豆類萃取物 1〇· 一種如申請專利範圍第1項之水 之製法,包括: 將粉化粗製豆類萃取物與水混合,每ι〇〇重量份水混合 18 1227661 (2004年9月修正) 1-50重量份丑粉粗萃取物; 將此混合物在6 0 -1 0 0 °C加熱1 〇 -1 2 0分; 於此混合物添加加凝集劑而形成懸浮液; 將此懸浮液在3 0 -1 〇 〇 °C加熱1 -1 2 0分;及 收集上清液,得水可溶豆類萃取物。 11·如申請專利範圍第10項之製法,其中豆類萃取物 基於大豆、綠豆、黑豆、或敏豆。 12 ·如申請專利範圍第丨〇項之製法,其中豆類萃取物 基於大豆。 13.如申請專利範圍第1〇項之製法,其中每ι〇〇重量份 水混合〇 · 〇 1 — 3重量份凝集劑。 14·如申請專利範圍第13項之製法,其中凝集劑為檸 檬酸。 15·如申請專利範圍第10項之製法,其中懸浮液藉過 濾來收集上清液。 、16 ·如申請專利範圍第1 〇項之製法,其中更將此上清 、乾蚝而得乾燥之水可溶豆類萃取物。
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AU783822B2 (en) | 2005-12-08 |
NZ520237A (en) | 2004-05-28 |
EP1239743B1 (en) | 2009-09-16 |
ATE442784T1 (de) | 2009-10-15 |
EP1239743A4 (en) | 2004-11-10 |
HK1051951A1 (en) | 2003-08-29 |
TW200305373A (en) | 2003-11-01 |
CN100366184C (zh) | 2008-02-06 |
US20020048627A1 (en) | 2002-04-25 |
KR20020075870A (ko) | 2002-10-07 |
US6616959B2 (en) | 2003-09-09 |
KR100733056B1 (ko) | 2007-06-27 |
CA2391247A1 (en) | 2001-06-21 |
WO2001043566A1 (en) | 2001-06-21 |
CA2391247C (en) | 2010-07-20 |
CN1411345A (zh) | 2003-04-16 |
JP2009278986A (ja) | 2009-12-03 |
DE60042980D1 (zh) | 2009-10-29 |
JP4413464B2 (ja) | 2010-02-10 |
AU2970500A (en) | 2001-06-25 |
US6458406B1 (en) | 2002-10-01 |
JP2003516739A (ja) | 2003-05-20 |
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