CN111135221B - 柑橘果实的萃取物及其用途 - Google Patents
柑橘果实的萃取物及其用途 Download PDFInfo
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- CN111135221B CN111135221B CN201910443271.7A CN201910443271A CN111135221B CN 111135221 B CN111135221 B CN 111135221B CN 201910443271 A CN201910443271 A CN 201910443271A CN 111135221 B CN111135221 B CN 111135221B
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- citrus fruit
- citrus
- ethyl acetate
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Abstract
本发明涉及植物提取物领域,尤其是关于一种柑橘果实的萃取物及其用途。所述柑橘果实的萃取物,通过以下方法制得:(a)以一萃取溶剂对该柑橘果实进行萃取而得到一粗萃取物;(b)令该粗萃取物进行一使用一由乙酸乙酯与水所构成的溶剂混合物的分配处理,形成一乙酸乙酯层以及一水层;以及(c)收集该乙酸乙酯层,继而移除乙酸乙酯,得到所述柑橘果实的萃取物。本发明提供所述的柑橘果实的萃取物用于制备一降低脂肪堆积的医药品或食品产品的用途。本发明的柑橘果实萃取物包含四甲基异高山黄芩素,其中四甲基异高山黄芩素具有下列化学式(I):
Description
技术领域
本发明涉及植物提取物领域,尤其是关于一种柑橘(Citrus reticulata)果实的萃取物及其用途。
背景技术
根据统计,肥胖与心血管疾病、第二型糖尿病、高血脂症、脂肪肝、及精神健康息息相关。因此,肥胖为影响身体健康的因素之一。其中,肥胖所观察到的现象不外乎是体重增加及/或脂肪堆积。当长时间热量吸收多于热量消耗,将导致体重增加;且对于成年人而言,体重增加的一部分原因是由于体内的脂肪组织增多及体脂肪增加。
除了肥胖以外,肝脏中三酸甘油酯的累积,也为影响身体健康的因素之一。当血液中三酸甘油酯量过高时,也会导致高血脂症;而高血脂症除会导致心脏疾病之外,也与脑中风、高血压、糖尿病、肾病等慢性疾病息息相关。
现代人对于健康议题日渐重视,目前各厂商无不积极开发可降低脂肪堆积的医药品及保健食品等。然而,习知的医药品及保健食品大多由化学成分所制成,长期使用不但对人体健康有害无益,且这些产品往往价格昂贵,并非为一般使用者所能负担。
为了解决上述问题,本领域的技术人员亟需研发出具有降低脂肪堆积的功效的新颖天然医药品或食品产品以造福有此需求的广大族群。
发明内容
有鉴于此,本发明的目的为提供一种柑橘(Citrus reticulata)果实的萃取物,是通过一包含下列步骤的方法而制得:(a)以一萃取溶剂对该柑橘果实进行萃取而得到一粗萃取物;(b)令粗萃取物进行一使用一由乙酸乙酯与水所构成的溶剂混合物的分配处理,俾以形成一乙酸乙酯层以及一水层;以及(c)收集乙酸乙酯层,继而移除乙酸乙酯,得到柑橘果实的萃取物。
在本发明的一实施例中,萃取的温度介于70℃至100℃。
在本发明的一实施例中,萃取溶剂与柑橘果实的体积比介于1~15:1~5。
在本发明的一实施例中,在步骤(b)中,溶剂混合物中乙酸乙酯与水的体积比为1:1。
在本发明的一实施例中,萃取溶剂是水、醇类、含水醇类或其组合。
在本发明的一实施例中,柑橘果实的萃取物包含四甲基异高山黄芩素(tetramethylisoscutellarein),其中四甲基异高山黄芩素具有下列化学式(I):
在本发明的一实施例中,四甲基异高山黄芩素是由一管柱层析方法而纯化出。
本发明的另一目的为提供一种如前所述的柑橘果实的萃取物用于制备一降低脂肪堆积的医药品或食品产品的用途。
本发明的另一目的为提供一种四甲基异高山黄芩素用于制备一降低脂肪堆积的医药品或食品产品的用途,其中四甲基异高山黄芩素具有下列化学式 (I):
在本发明的一实施例中,医药品包含一医药上可接受的载剂。
在本发明的一实施例中,医药品是呈一供非经肠道投药的剂型。
在本发明的一实施例中,医药品是呈一供口服投药的剂型。
综上所述,本发明柑橘果实的萃取物的功效在于:抑制脂肪堆积进而达到减脂的功效。
以下将进一步说明本发明的实施方式,下述所列举的实施例是用以阐明本发明,并非用以限定本发明的范围,任何熟习此技艺者,在不脱离本发明的精神和范围内,当可做些许更动与润饰,因此本发明的保护范围当视后附的申请专利范围所界定者为准。
附图说明
图1是化合物TCI-CR-03的核磁共振氢光谱图;
图2是本发明柑橘果实的萃取物在降低脂肪堆积上的功效的数据图;
图3是四甲基异高山黄芩素在降低脂肪堆积上的功效的数据图。
具体实施方式
定义
本文中所使用数值为近似值,所有实验数据皆表示在20%的范围内,较佳为在10%的范围内,最佳为在5%的范围内。
使用Excel软件进行统计分析。个此之间的差异以学生t检验(student's t-test)分析。
依据本发明,柑橘(Citrus reticulata)是芸香科(Rutaceae)柑橘属(Citrus)的宽皮柑橘类,果实外皮肥厚,内藏瓤瓣,由汁泡和种子构成。产区主要分布于中国、西班牙、巴西及日本。柑橘中的维生素A可增强人体在黑暗环境中的视力和治疗夜盲症。柑橘不宜食用过量,吃太多会患有胡萝卜素血症,皮肤呈深黄色,如同黄疸一般。
如本文中所使用的,用语「柑橘果实(Citrus reticulata fruitlet)」意指柑橘花开花后60~90天且直径在3~5cm的柑橘果实。
依据本发明,柑橘果实的萃取物可以使用新鲜的柑橘果实而被制备,或者可使用预先经过一选自于由下列所构成的群组中的加工处理的柑橘果实而被制备:干燥处理、研磨处理、切碎处理,及其组合。
如本文中所使用的,用语「四甲基异高山黄芩素(tetramethylisoscutellarein)」又被称为5784’-四甲氧黄酮(5784’-tetramethoxyflavone),是一种8-o-甲基化类黄酮(8-o-methylated flavonoids)化合物的成员。四甲基异高山黄芩素具有以下化学式(I):
依据本发明,医药品可利用熟习此技艺者所详知的技术而被制造成一适合于非经肠地道(parenterally)或口服地(orally)投药的剂型(dosage form),这包括,但不限于:注射品(injection)[例如,无菌的水性溶液(sterile aqueous solution)或分散液(dispersion)]、无菌的粉末(sterile powder)、锭剂(tablet)、片剂(troche)、口含锭(lozenge)、丸剂(pill)、胶囊(capsule)、分散性粉末(dispersible powder)或细颗粒(granule)、溶液、悬浮液(suspension)、乳剂(emulsion)、糖浆(syrup)、酏剂(elixir)、浓浆(slurry)以及类似物。
依据本发明的医药品可以一选自于由下列所构成的群组中的非经肠道途径(parenteral routes)来投药:腹膜内注射(intraperitoneal injection)、皮下注射(subcutaneous injection)、肌肉内注射(intramuscular injection)以及静脉内注射(intravenous injection)。
依据本发明的医药品可包含有一被广泛地使用于药物制造技术的药学上可接受的载剂。例如,该药学上可接受的载剂可包含一或多种选自于由下列所构成的群组中的试剂:溶剂(solvent)、乳化剂(emulsifier)、悬浮剂(suspending agent)、分解剂(decomposer)、黏结剂(binding agent)、赋形剂(excipient)、安定剂(stabilizingagent)、螯合剂(chelating agent)、稀释剂(diluent)、胶凝剂(gelling agent)、防腐剂(preservative)、润滑剂(lubricant)、吸收延迟剂(absorption delaying agent)、脂质体(liposome)以及类似物。有关这些试剂的选用与数量是落在熟习此项技术的人士的专业素养与例行技术范畴内。
依据本发明,该药学上可接受的载剂包含有一选自于由下列所构成的群组中的溶剂:水、生理盐水(normal saline)、磷酸盐缓冲生理盐水(phosphate buffered saline,PBS)、含糖溶液、含有醇的水性溶液(aqueous solution containing alcohol),以及它们的组合。
依据本发明,食品产品可被当作食品添加物(food additive),由习知方法于原料制备时添加,或是于食品的制作过程中添加,而与任一种可食性材料配制成供人类与非人类动物摄食的食品产品。
依据本发明,食品产品的种类包括但不限于:饮料(beverages)、发酵食品(fermented foods)、烘培产品(bakery products)、健康食品(health foods)以及膳食补充品(dietary supplements)。
实施例1.柑橘果实的萃取物及其化合物的制备与纯化
1.1柑橘果实的萃取物的制备
首先,将柑橘果实粉碎为约1~2cm的大小,继而以水、醇类、含水醇类或其组合作为萃取溶剂对经粉碎处理的柑橘果实进行萃取,其中萃取的温度介于70℃至100℃,萃取溶剂与柑橘果实的体积比介于1~15:1~5。接着,将所得到的粗萃取物进行离心,接而取离心后的上清液并将的过滤而得到一滤液。之后,将滤液于45℃至70℃进行减压浓缩而得到一浓缩产物(以下称为柑橘果实的原萃取物)。接着,取2L的柑橘果实的原萃取物并使用乙酸乙酯(ethyl acetate)与水等比例1:1(v/v)的液相分配处理共3次,俾以形成一乙酸乙酯层以及一水层(以下称为柑橘果实的水层萃取物)。之后,收集乙酸乙酯层,继而移除乙酸乙酯,并进行减压浓缩及干燥处理,得到本发明柑橘果实的萃取物。另外,本发明亦以大致相同于本发明柑橘果实的萃取物的制备方式制备柑橘果实的正丁醇层萃取物,不同之处在于:以正丁醇取代乙酸乙酯。
1.2四甲基异高山黄芩素(tetramethylisoscutellarein)的纯化
首先,依据生物活性导引分离方法(bioassay guided fractionation),将5.4g的本发明柑橘果实的萃取物以二氯甲烷与甲醇(15:1)混合溶剂系统,硅胶管柱层析方法(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MerckRP-18(40-63μm,Art.0250))分离得到10个划分层(F-1~F-10)。接着,将第二个划分层(F-2)以水与甲醇(1:1)混合溶剂系统, C18管柱层析方法分离得到5个划分层(F-2-1~F-2-5)。之后,将划分层(F-2-4) 以水与甲醇(1.5:1)混合溶剂系统,C18管柱层析方法分离得到5.3mg的化合物 TCI-CR-03。
化合物TCI-CR-03为一个淡黄色油状物,并将其进行核磁共振氢光谱(1H nuclearmagnetic resonance spectrometer,1H NMR)分析(1D与2D光谱使用 400MHz Varian400FT-NMR;以δ表示化学位移(chemical shift),单位为ppm;以TMS(tetramethylsilane;δ=0)作为内部标准品;偶合常数 (J)以Hz为单位,并以s窗体峰(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表宽峰),结果显示于图1。图1是化合物TCI-CR-03的核磁共振氢光谱图。由图1可见,有两组芳香环区域互相耦合质子δH 7.10(2H,d,J=8.4Hz),δH 7.99(1H,d,J=8.4Hz),以及两支单峰的质子讯号在δH 6.6(1H,s),δH 6.7(1H,s),另外发现有四支甲氧基的讯号分别在δH 3.89,δH 3.92,δH 3.96,δH 4.04。综合以上光谱信息与文献比对,确认化合物TCI-CR-03为四甲基异高山黄芩素。
实施例2.柑橘果实的萃取物及其化合物在降低脂肪堆积上的效用评估
2.1柑橘果实的萃取物在降低脂肪堆积上的效用评估
首先,将8×104小鼠骨髓基质细胞(bone marrow stromal cell)OP9(CRL-2749TM)与500μL的脂肪前细胞扩增培养基(pre-adipocyte expansion medium)(添加有90%最低必需培养基Alpha培养基(minimum essential medium alpha medium)(Gibco)、20%胎牛血清(fetal bovine serum)(Gibco)及1%青霉素/ 链霉素(penicillin/streptomycin)(Gibco))接种于24孔培养盘中,并于37℃下培养7天,每3天更换新鲜的分化培养基(differentiation medium)(添加有90%最低必需培养基Alpha培养基、20%胎牛血清及1%青霉素/链霉素)。接着,使用显微镜(ZEISS)观察油滴(lipiddroplet)形成以确认细胞完全分化。
之后,将OP9细胞分成5组,其中包括1个对照组、3个比较组(亦即比较组1~比较组3)及1个实验组。将1mg/mL柑橘果实的原萃取物、1mg/mL 柑橘果实的正丁醇层萃取物及1mg/mL柑橘果实的水层萃取物分别添加至比较组1~比较组3的细胞中,将1mg/mL本发明柑橘果实的萃取物添加至实验组的细胞中,至于对照组的细胞则不做任何处理。接着,将各组细胞培养7~10 天,每3天更换培养基。
接着,移除培养基并以1mL的PBS对每孔润洗2次,继而添加1mL的 10%甲醛(formaldehyde)(ECHO)以固定细胞并于室温下培养30分钟。之后,移除甲醛并以1mL的PBS对每孔润洗2次,继而添加1mL的60%异丙醇 (isopropanol)(ECHO)至每孔并作用1分钟。在移除异丙醇之后,添加1mL的油-红O工作溶液(oil-red O working solution)(将60%油-红O染色试剂的储备溶液(stock solution)(Sigma;3mg/mL配于100%异丙醇)以ddH2O制备)并于室温下作用1小时。接着,移除油-红O工作溶液并以1mL的60%异丙醇快速退染5秒,接而使用显微镜拍照。
之后,使用100%异丙醇溶解油滴,接而将培养盘置于振荡器(shaker)上并培育10分钟,然后取100μL的体积至96-孔培养盘并于510nm的波长下以 ELISA读取仪(BioTek)来读取各孔的吸光值(OD510)。
各组之间的统计学显著差异是由学生t检验来决定。本实施例的结果显示于图2。
图2是本发明柑橘果实的萃取物在降低脂肪堆积上的功效的数据图。由图 2可见,与对照组及比较组1~3相较之下,实验组的油红相对百分比有降低的情形。本实施例的结果显示,本发明柑橘果实的萃取物具有降低脂肪堆积的功效。
2.2四甲基异高山黄芩素在降低脂肪堆积上的效用评估
首先,将8×104小鼠骨髓基质细胞OP9(CRL-2749TM)与500μL的脂肪前细胞扩增培养基(添加有90%最低必需培养基Alpha培养基、20%胎牛血清及1%青霉素/链霉素)接种于24孔培养盘中,并于37℃下培养7天,每3 天更换新鲜的分化培养基(添加有90%最低必需培养基Alpha培养基、20%胎牛血清及1%青霉素/链霉素)。接着,使用显微镜(ZEISS)观察油滴形成以确认细胞完全分化。
之后,将OP9细胞分成2组,其中包括1个对照组及1个实验组。将10 μg/mL四甲基异高山黄芩素添加至实验组的细胞中,至于对照组的细胞则不做任何处理。接着,将各组细胞培养7~10天,每3天更换培养基。
接着,移除培养基并以1mL的PBS对每孔润洗2次,继而添加1mL的 10%甲醛以固定细胞并于室温下培养30分钟。之后,移除甲醛并以1mL的 PBS对每孔润洗2次,继而添加1mL的60%异丙醇至每孔并作用1分钟。在移除异丙醇之后,添加1mL的油-红O工作溶液(将60%油-红O染色试剂的储备溶液(Sigma;3mg/mL配于100%异丙醇)以ddH2O制备)并于室温下作用1 小时。接着,移除油-红O工作溶液并以1mL的60%异丙醇快速退染5秒,接而使用显微镜拍照。
之后,使用100%异丙醇溶解油滴,接而将培养盘置于振荡器上并培育10 分钟,然后取100μL的体积至96-孔培养盘并于510nm的波长下以ELISA读取仪来读取各孔的吸光值(OD510)。
各组之间的统计学显著差异是由学生t检验来决定。本实施例的结果显示于图3。
图3是四甲基异高山黄芩素在降低脂肪堆积上的功效的数据图。由图3 可见,与对照组相较之下,实验组的油红相对百分比有降低的情形(与对照组比较,降低28%)。本实施例的结果显示,从本发明柑橘果实的萃取物中分离出的四甲基异高山黄芩素亦具有降低脂肪堆积的功效。
综上所述,本发明柑橘果实的萃取物及由其分离出的四甲基异高山黄芩素确实具有降低脂肪堆积进而达到减脂的功效。
以上所述仅为举例性,而非为限制性者。任何未脱离本发明的精神与范畴,而对其进行的等效修改或变更,均应包含于后附的申请专利范围中。
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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 |
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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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TW202017583A (zh) | 2020-05-16 |
US20210308205A1 (en) | 2021-10-07 |
US20200138893A1 (en) | 2020-05-07 |
CN111135221A (zh) | 2020-05-12 |
US11052124B2 (en) | 2021-07-06 |
US11622988B2 (en) | 2023-04-11 |
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