TW202017583A - 柑橘幼果的萃取物及其用途 - Google Patents
柑橘幼果的萃取物及其用途 Download PDFInfo
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Abstract
本發明提供一種柑橘幼果的萃取物及其用於降低脂肪堆積的用途。本發明的柑橘幼果萃取物包含四甲基異高山黃芩素,其中四甲基異高山黃芩素具有下列化學式(I):
Description
本發明是有關於一種柑橘(Citrus reticulata)幼果的萃取物及其用於降低脂肪堆積的用途。
根據統計,肥胖與心血管疾病、第二型糖尿病、高血脂症、脂肪肝、及精神健康息息相關。因此,肥胖為影響身體健康的因素之一。其中,肥胖所觀察到的現象不外乎是體重增加及/或脂肪堆積。當長時間熱量吸收多於熱量消耗,將導致體重增加;且對於成年人而言,體重增加的一部分原因是由於體內的脂肪組織增多及體脂肪增加。
除了肥胖以外,肝臟中三酸甘油酯的累積,也為影響身體健康的因素之一。當血液中三酸甘油酯量過高時,也會導致高血脂症;而高血脂症除會導致心臟疾病之外,也與腦中風、高血壓、糖尿病、腎病等慢性疾病息息相關。
現代人對於健康議題日漸重視,目前各廠商無不積極開發可降低脂肪堆積之醫藥品及保健食品等。然而,習知的醫藥品及保健食品大多由化學成分所製成,長期使用不但對人體健康有害無益,且這些產品往往價格昂貴,並非為一般使用者所能負擔。
為了解決上述問題,本領域的技術人員亟需研發出具有降低脂肪堆積之功效的新穎天然醫藥品或食品產品以造福有此需求的廣大族群。
有鑑於此,本發明之目的為提供一種柑橘(Citrus reticulata)幼果的萃取物,係藉由一包含下列步驟之方法而製得:(a)以一萃取溶劑對該柑橘幼果進行萃取而得到一粗萃取物;(b)令粗萃取物進行一使用一由乙酸乙酯與水所構成之溶劑混合物的分配處理,俾以形成一乙酸乙酯層以及一水層;以及(c)收集乙酸乙酯層,繼而移除乙酸乙酯,藉此而得到柑橘幼果的萃取物。
在本發明的一實施例中,萃取的溫度介於70℃至100℃。
在本發明的一實施例中,萃取溶劑與柑橘幼果的體積比介於1~15:1~5。
在本發明的一實施例中,在步驟(b)中,溶劑混合物中乙酸乙酯與水的體積比為1:1。
在本發明的一實施例中,萃取溶劑是水、醇類、含水醇類或其組合。
在本發明的一實施例中,四甲基異高山黃芩素是藉由一管柱層析方法而純化出。
本發明之另一目的為提供一種如前所述的柑橘幼果的萃取物用於製備一降低脂肪堆積之醫藥品或食品產品的用途。
在本發明的一實施例中,醫藥品包含一醫藥上可接受的載劑。
在本發明的一實施例中,醫藥品是呈一供非經腸道投藥的劑型。
在本發明的一實施例中,醫藥品是呈一供口服投藥的劑型。
綜上所述,本發明柑橘幼果的萃取物之功效在於:抑制脂肪堆積進而達到減脂的功效。
以下將進一步說明本發明的實施方式,下述所列舉的實施例係用以闡明本發明,並非用以限定本發明之範圍,任何熟習此技藝者,在不脫離本發明之精神和範圍內,當可做些許更動與潤飾,因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
圖1是化合物TCI-CR-03的核磁共振氫光譜圖。
圖2是本發明柑橘幼果的萃取物在降低脂肪堆積上的功效之數據圖。
圖3是四甲基異高山黃芩素在降低脂肪堆積上的功效之數據圖。
本文中所使用數值為近似值,所有實驗數據皆表示在20%的範圍內,較佳為在10%的範圍內,最佳為在5%的範圍內。
使用Excel軟體進行統計分析。個此之間的差異以學生t檢驗(student's t-test)分析。
依據本發明,柑橘(Citrus reticulata)是芸香科(Rutaceae)柑橘屬(Citrus)的寬皮柑橘類,幼果外皮肥厚,內藏瓤瓣,由汁泡和種子構成。產區主要分佈於中國、西班牙、巴西及日本。柑橘中的維生素A可增強人體在黑暗環境中的視力和治療夜盲症。柑橘不宜食用過量,吃太多會患有胡蘿蔔素血症,皮膚呈深黃色,如同黃疸一般。
如本文中所使用的,用語「柑橘幼果(Citrus reticulata fruitlet)」意指柑橘花開花後60~90天且直徑在3~5cm的柑橘果實。
依據本發明,柑橘幼果的萃取物可以使用新鮮的柑橘幼果而被製備,或者可使用預先經過一選自於由下列所構成之群組中的加工處理的柑橘幼果而被製備:乾燥處理、研磨處理、切碎處理,及其組合。
如本文中所使用的,用語「四甲基異高山黃芩素(tetramethylisoscutellarein)」又被稱為5784’-四甲氧黃酮(5784’-tetramethoxyflavone),是一種8-o-甲基化類黃酮(8-o-methylated flavonoids)化合物的成員。四甲基異高山黃芩素具有以下化學式(I):
依據本發明,醫藥品可利用熟習此技藝者所詳知的技術而被製造成一適合於非經腸道地(parenterally)或口服地(orally)投藥的劑型(dosage form),這包括,但不限於:注射品(injection)[例如,無菌的水性溶液(sterile aqueous solution)或分散液(dispersion)]、無菌的粉末(sterile powder)、錠劑(tablet)、片劑(troche)、口含錠(lozenge)、丸劑(pill)、膠囊(capsule)、分散性粉末(dispersible
powder)或細顆粒(granule)、溶液、懸浮液(suspension)、乳劑(emulsion)、糖漿(syrup)、酏劑(elixir)、濃漿(slurry)以及類似之物。
依據本發明的醫藥品可以一選自於由下列所構成的群組中的非經腸道途徑(parenteral routes)來投藥:腹膜內注射(intraperitoneal injection)、皮下注射(subcutaneous injection)、肌肉內注射(intramuscular injection)以及靜脈內注射(intravenous injection)。
依據本發明的醫藥品可包含有一被廣泛地使用於藥物製造技術之藥學上可接受的載劑。例如,該藥學上可接受的載劑可包含一或多種選自於由下列所構成之群組中的試劑:溶劑(solvent)、乳化劑(emulsifier)、懸浮劑(suspending agent)、分解劑(decomposer)、黏結劑(binding agent)、賦形劑(excipient)、安定劑(stabilizing agent)、螯合劑(chelating agent)、稀釋劑(diluent)、膠凝劑(gelling agent)、防腐劑(preservative)、潤滑劑(lubricant)、吸收延遲劑(absorption delaying agent)、脂質體(liposome)以及類似之物。有關這些試劑的選用與數量是落在熟習此項技術之人士的專業素養與例行技術範疇內。
依據本發明,該藥學上可接受的載劑包含有一選自於由下列所構成之群組中的溶劑:水、生理鹽水(normal saline)、磷酸鹽緩衝生理鹽水(phosphate buffered saline,PBS)、含糖溶液、含有醇的水性溶液(aqueous solution containing alcohol),以及它們的組合。
依據本發明,食品產品可被當作食品添加物(food additive),藉由習知方法於原料製備時添加,或是於食品的製作過程中添加,而與任一種可食性材料配製成供人類與非人類動物攝食的食品產品。
依據本發明,食品產品的種類包括但不限於:飲料(beverages)、發酵食品(fermented foods)、烘培產品(bakery products)、健康食品(health foods)以及膳食補充品(dietary supplements)。
1.1 柑橘幼果的萃取物之製備
首先,將柑橘幼果粉碎為約1~2cm的大小,繼而以水、醇類、含水醇類或其組合作為萃取溶劑對經粉碎處理的柑橘幼果進行萃取,其中萃取的溫度介於70℃至100℃,萃取溶劑與柑橘幼果的體積比介於1~15:1~5。接著,將所得到的粗萃取物進行離心,接而取離心後的上清液並將之過濾而得到一濾液。之後,將濾液於45℃至70℃進行減壓濃縮而得到一濃縮產物(以下稱為柑橘幼果的原萃取物)。接著,取2L的柑橘幼果的原萃取物並使用乙酸乙酯(ethyl acetate)與水等比例1:1(v/v)的液相分配處理共3次,俾以形成一乙酸乙酯層以及一水層(以下稱為柑橘幼果的水層萃取物)。之後,收集乙酸乙酯層,繼而移除乙酸乙酯,並進行減壓濃縮及乾燥處理,藉此而得到本發明柑橘幼果的萃取物。另外,本發明亦以大致相同於本發明柑橘幼果的萃取物的製備方式製備柑橘幼果的正丁醇層萃取物,不同之處在於:以正丁醇取代乙酸乙酯。
1.2 四甲基異高山黃芩素(tetramethylisoscutellarein)的純化
首先,依據生物活性導引分離方法(bioassay guided fractionation),將5.4g之本發明柑橘幼果的萃取物以二氯甲烷與甲醇(15:1)混合溶劑系統,矽膠管柱層析方法(column chromatography)(填充材料包括Sephadex LH-20(Amersham Biosciences)、Diaion HP-20(Mitsubishi Chemical)、Merck Kieselgel 60(40-63μm,Art.9385)、及Merck LiChroprep® RP-18(40-63μm,Art.0250))分離得到10個劃分層(F-1~F-10)。接著,將第二個劃分層(F-2)以水與甲醇(1:1)混合溶劑系統,C18管柱層析方法分離得到5個劃分層(F-2-1~F-2-5)。之後,將劃分層(F-2-4)以水與甲醇(1.5:1)混合溶劑系統,C18管柱層析方法分離得到5.3mg的化合物TCI-CR-03。
化合物TCI-CR-03為一個淡黃色油狀物,並將之進行核磁共振氫光譜(1H nuclear magnetic resonance spectrometer,1H NMR)分析(1D與2D光譜使用400MHz Varian 400 FT-NMR;以δ表示化學位移(chemical shift),單位為ppm;以TMS(tetramethylsilane;δ=0)作為內部標準品;偶合常數(J)以Hz為單位,並以s表單峰(singlet),d表二重峰(doublet),t表三重峰(triplet),q表四重峰(quartet),p表五重峰,m表多重峰(multiplet),brs表寬峰),結果顯示於圖1。圖1是化合物TCI-CR-03的核磁共振氫光譜圖。由圖1可見,有兩組芳香環區域互相耦合質子δ H 7.10(2H,d,J=8.4Hz),δ H 7.99(1H,d,J=8.4Hz),以及兩支單峰的質子訊
號在δ H 6.6(1H,s),δ H 6.7(1H,s),另外發現有四支甲氧基的訊號分別在δ H 3.89,δ H 3.92,δ H 3.96,δ H 4.04。綜合以上光譜資訊與文獻比對,確認化合物TCI-CR-03為四甲基異高山黃芩素。
2.1 柑橘幼果的萃取物在降低脂肪堆積上的效用評估
首先,將8×104小鼠骨髓基質細胞(bone marrow stromal cell)OP9(ATCC® CRL-2749TM)與500μL的脂肪前細胞擴增培養基(pre-adipocyte expansion medium)(添加有90%最低必需培養基Alpha培養基(minimum essential medium alpha medium)(Gibco)、20%胎牛血清(fetal bovine serum)(Gibco)及1%青黴素/鏈黴素(penicillin/streptomycin)(Gibco))接種於24孔培養盤中,並於37℃下培養7天,每3天更換新鮮的分化培養基(differentiation medium)(添加有90%最低必需培養基Alpha培養基、20%胎牛血清及1%青黴素/鏈黴素)。接著,使用顯微鏡(ZEISS)觀察油滴(lipid droplet)形成以確認細胞完全分化。
之後,將OP9細胞分成5組,其中包括1個對照組、3個比較組(亦即比較組1~比較組3)及1個實驗組。將1mg/mL柑橘幼果的原萃取物、1mg/mL柑橘幼果的正丁醇層萃取物及1mg/mL柑橘幼果的水層萃取物分別添加至比較組1~比較組3的細胞中,將1mg/mL本發明柑橘幼果的萃取物添加至實驗組的細胞中,至於對照組的細胞則不做任何處理。接著,將各組細胞培養7~10天,每3天更換培養基。
接著,移除培養基並以1mL的PBS對每孔潤洗2次,繼而添加1mL的10%甲醛(formaldehyde)(ECHO)以固定細胞並於室溫下培養30分鐘。之後,移除甲醛並以1mL的PBS對每孔潤洗2次,繼而添加1mL的60%異丙醇(isopropanol)(ECHO)至每孔並作用1分鐘。在移除異丙醇之後,添加1mL的油-紅O工作溶液(oil-red O working solution)(將60%油-紅O染色試劑的儲備溶液(stock solution)(Sigma;3mg/mL配於100%異丙醇)以ddH2O製備)並於室溫下作用1小時。接著,移除油-紅O工作溶液並以1mL的60%異丙醇快速退染5秒,接而使用顯微鏡拍照。
之後,使用100%異丙醇溶解油滴,接而將培養盤置於振盪器(shaker)上並培育10分鐘,然後取100μL的體積至96-孔培養盤並於510nm的波長下以ELISA讀取儀(BioTek)來讀取各孔的吸光值(OD510)。
各組之間的統計學顯著差異是藉由學生t檢驗來決定。本實施例的結果顯示於圖2。
圖2是本發明柑橘幼果的萃取物在降低脂肪堆積上的功效之數據圖。由圖2可見,與對照組及比較組1~3相較之下,實驗組的油紅相對百分比有降低的情形。本實施例的結果顯示,本發明柑橘幼果的萃取物具有降低脂肪堆積的功效。
2.2 四甲基異高山黃芩素在降低脂肪堆積上的效用評估
首先,將8×104小鼠骨髓基質細胞OP9(ATCC® CRL-2749TM)與500μL的脂肪前細胞擴增培養基(添加有90%最低必需培養基Alpha培養基、20%胎牛血清及1%青黴素/鏈黴素)接種於24孔培養盤中,並於37℃下培養7天,每3天更換新鮮的分化培養基(添加有90%最低必需培養基Alpha培養基、20%胎牛血清及1%青黴素/鏈黴素)。接著,使用顯微鏡(ZEISS)觀察油滴形成以確認細胞完全分化。
之後,將OP9細胞分成2組,其中包括1個對照組及1個實驗組。將10μg/mL四甲基異高山黃芩素添加至實驗組的細胞中,至於對照組的細胞則不做任何處理。接著,將各組細胞培養7~10天,每3天更換培養基。
接著,移除培養基並以1mL的PBS對每孔潤洗2次,繼而添加1mL的10%甲醛以固定細胞並於室溫下培養30分鐘。之後,移除甲醛並以1mL的PBS對每孔潤洗2次,繼而添加1mL的60%異丙醇至每孔並作用1分鐘。在移除異丙醇之後,添加1mL的油-紅O工作溶液(將60%油-紅O染色試劑的儲備溶液(Sigma;3mg/mL配於100%異丙醇)以ddH2O製備)並於室溫下作用1小時。接著,移除油-紅O工作溶液並以1mL的60%異丙醇快速退染5秒,接而使用顯微鏡拍照。
之後,使用100%異丙醇溶解油滴,接而將培養盤置於振盪器上並培育10分鐘,然後取100μL的體積至96-孔培養盤並於510nm的波長下以ELISA讀取儀來讀取各孔的吸光值(OD510)。
各組之間的統計學顯著差異是藉由學生t檢驗來決定。本實施例的結果顯示於圖3。
圖3是四甲基異高山黃芩素在降低脂肪堆積上的功效之數據圖。由圖3可見,與對照組相較之下,實驗組的油紅相對百分比有降低的情形(與對照組比較,降低28%)。本實施例的結果顯示,從本發明柑橘幼果的萃取物中分離出的四甲基異高山黃芩素亦具有降低脂肪堆積的功效。
綜上所述,本發明柑橘幼果的萃取物及由其分離出的四甲基異高山黃芩素確實具有降低脂肪堆積進而達到減脂的功效。
以上所述僅為舉例性,而非為限制性者。任何未脫離本發明之精神與範疇,而對其進行之等效修改或變更,均應包含於後附之申請專利範圍中。
Claims (12)
- 一種柑橘(Citrus reticulata)幼果的萃取物,係藉由一包含下列步驟之方法而製得:(a)以一萃取溶劑對該柑橘幼果進行萃取而得到一粗萃取物;(b)令該粗萃取物進行一使用一由乙酸乙酯與水所構成之溶劑混合物的分配處理,俾以形成一乙酸乙酯層以及一水層;以及(c)收集該乙酸乙酯層,繼而移除乙酸乙酯,藉此而得到該柑橘幼果的萃取物。
- 如申請專利範圍第1項所述的柑橘幼果的萃取物,其中該萃取的溫度介於70℃至100℃。
- 如申請專利範圍第1項所述的柑橘幼果的萃取物,其中該萃取溶劑與該柑橘幼果的體積比介於1~15:1~5。
- 如申請專利範圍第1項所述的柑橘幼果的萃取物,其中在步驟(b)中,該溶劑混合物中乙酸乙酯與水的體積比為1:1。
- 如申請專利範圍第1項所述的柑橘幼果的萃取物,其中該萃取溶劑是水、醇類、含水醇類或其組合。
- 如申請專利範圍第6項所述的柑橘幼果的萃取物,其中該四甲基異高山黃芩素是藉由一管柱層析方法而純化出。
- 一種如申請專利範圍第1項所述的柑橘幼果的萃取物用於製備一降低脂肪堆積之醫藥品或食品產品的用途。
- 如申請專利範圍第9項所述的用途,其中該醫藥品包含一醫藥上可接受的載劑。
- 如申請專利範圍第9項所述的用途,其中該醫藥品是呈一供非經腸道投藥的劑型。
- 如申請專利範圍第9項所述的用途,其中該醫藥品是呈一供口服投藥的劑型。
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TW107139205A TW202017583A (zh) | 2018-11-05 | 2018-11-05 | 柑橘幼果的萃取物及其用途 |
CN201910443271.7A CN111135221B (zh) | 2018-11-05 | 2019-05-24 | 柑橘果实的萃取物及其用途 |
US16/533,865 US11052124B2 (en) | 2018-11-05 | 2019-08-07 | Method for reducing fat accumulation by using early-harvested citrus reticulata fruit extract |
US17/324,130 US11622988B2 (en) | 2018-11-05 | 2021-05-19 | Method for reducing fat accumulation by using tetramethylisoscutellarein |
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CN115772145A (zh) * | 2022-11-29 | 2023-03-10 | 三峡大学 | 一种柑橘属果实提取物及其制备方法与应用 |
CN116267603B (zh) * | 2023-01-13 | 2023-09-08 | 中国科学院华南植物园 | 白肋朱顶红丛芽增殖和体细胞发生混合途径快速繁殖方法 |
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CN100345566C (zh) * | 2005-04-11 | 2007-10-31 | 成都华高药业有限公司 | 一种用于减肥的药物组合物及其制备方法和用途 |
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