CN105189526B - 用于制备香豆雌酚或香豆雌甙的方法 - Google Patents
用于制备香豆雌酚或香豆雌甙的方法 Download PDFInfo
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- CN105189526B CN105189526B CN201480011366.7A CN201480011366A CN105189526B CN 105189526 B CN105189526 B CN 105189526B CN 201480011366 A CN201480011366 A CN 201480011366A CN 105189526 B CN105189526 B CN 105189526B
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- coumestrol
- chitosan
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- extract
- leguminous
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- ZZIALNLLNHEQPJ-UHFFFAOYSA-N coumestrol Chemical compound C1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C12 ZZIALNLLNHEQPJ-UHFFFAOYSA-N 0.000 title claims abstract description 214
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- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了一种用于制备香豆雌酚的方法和用于制备香豆雌甙的方法,其中在豆类生长期用壳聚糖进行预设时间量的处理。此外,本发明公开了通过对由制备方法制备的香豆雌甙进行酶处理或酸处理等等来制备香豆雌酚的方法。
Description
技术领域
本发明涉及用于制备香豆雌酚或香豆雌甙(coumestrin)的方法。
背景技术
由于USFDA禁止在对绝经女性的雌激素疗法中使用具有强大的雌激素影响的便宜的合成雌激素,例如己烯雌酚(DES),因此可替代女性荷尔蒙的天然植物雌激素已囊括了研究兴趣。但是,由于这些物质是以微量形式存在于自然界,所以非常困难获得大量的这些物质。由于对大规模合成这些物质的不冷不热的态度,导致超过半个世纪也没有显著进步。虽然已经报道了少量的合成方法,但是它们都仅仅是实验室规模,而且目前没有一种用于大规模生产的容易的方法。香豆雌酚是至今知道的最强大的植物雌激素,主要发现于豆科和菊科植物的种子、根和叶中。香豆雌酚是一种异黄酮,通常分类为香豆草醚类化合物(coumestan-based compound)。在植物的伤口部位分泌高浓度的香豆雌酚,已知它能够通过抗氧化、抗炎症、抗毒素的作用防止细菌、真菌和病毒的感染(Darbarwar, M., et al.,J. Sci. Ind. Res., 35, 297, 1982; Jeffrey, B. H., et al., PhytochemicalDictionary, Taylor & Francis, London, pp 418, 1933)。因为各种细菌、真菌、病毒等的感染导致包括香豆雌酚的各种芳香类化合物的合成。已知香豆雌酚的抗菌作用的原因在于酚醛骨架结构,其通过防止自由基氧化剂的流入而抑制过氧化合物在体内的产生。此外,在各种天然香豆草醚类衍生物中,已知仅仅香豆雌酚具有雌激素作用。通过对幼龄大鼠口服给药香豆雌酚,然后监控子宫重量的变化来评估雌激素作用。应该注意到的是,香豆雌酚对年轻雌性大鼠表现出雌激素作用,而对成熟雄性大鼠没有作用,而且没有表现出任何毒性(Darbarwar, M., et al., J. Sci. Ind. Res., 35, 297, 1982)。但是,因为香豆雌酚以微量形式存在于豆科植物中,所以它非常昂贵。鉴于这个原因,已经有一些通过合成来获得香豆雌酚的尝试。但是,由于其具有几个芳香稠环的相当复杂的化学结构,至今还没有报道简单的合成方法。虽然已经报道了一些合成方法,但是它们有很多问题,且不适于商业应用。目前,在天然衍生的物质比化学合成的物质更安全的方面,正积极地研究通过天然途径进行大规模生产的方法。
发明内容
技术问题
一方面,本发明涉及提供一种从豆科植物制备香豆雌酚或香豆雌甙的方法。另一方面,本发明涉及提供通过香豆雌甙的脱糖基化制备大批量的香豆雌酚的方法。
技术方案
一方面,本发明提供一种制备香豆雌甙的方法,包括在豆科植物的营养生长期,用壳聚糖处理豆科植物或土壤。
另一方面,本发明提供一种制备香豆雌甙的方法,其中用壳聚糖处理豆科植物的根。
另一方面,本发明提供一种制备香豆雌甙的方法,其中在营养生长期的VE至V4期中的任一期用壳聚糖处理豆科植物。
另一方面,本发明提供用于制备香豆雌甙的方法,其中使用低分子量、水溶性壳聚糖。
另一方面,本发明提供用于制备香豆雌甙的方法,其中每隔4-6天进行一次壳聚糖处理。
另一方面,本发明提供用于制备香豆雌甙的方法,其进一步包括制备豆科植物的提取物。
另一方面,本发明提供用于制备香豆雌甙的方法,其中使用所述豆科植物的根部提取物。
另一方面,本发明提供一种制备香豆雌酚的方法,包括在豆科植物的营养生长期,用壳聚糖处理豆科植物或土壤。
另一方面,本发明提供一种制备香豆雌酚的方法,其中用壳聚糖处理豆科植物的根。
另一方面,本发明提供一种制备香豆雌酚的方法,其中在营养生长期的VE至V4期中的任一期用壳聚糖处理豆科植物。
另一方面,本发明提供用于制备香豆雌酚的方法,其中使用低分子量、水溶性壳聚糖。
另一方面,本发明提供用于制备香豆雌酚的方法,其中每隔4-6天进行一次壳聚糖处理。
另一方面,本发明提供用于制备香豆雌酚的方法,其进一步包括制备豆科植物的提取物。
另一方面,本发明提供用于制备香豆雌酚的方法,其中使用所述豆科植物的根部提取物。
另一方面,本发明提供一种制备香豆雌酚的方法,包括:根据上述方法制备香豆雌甙和香豆雌酚;通过利用选自酸、碱、酶和微生物中的一种或多种物质来处理所述香豆雌甙,对香豆雌甙脱糖基化。
另一方面,本发明提供一种制备香豆雌酚的方法,其中利用选自酸、碱、酶和微生物中的一种或多种物质处理含有香豆雌甙的豆科植物的提取物。
有益效果
一方面,一种用于制备香豆雌酚或香豆雌甙的方法,其中使用豆科植物,通过增加制备的香豆雌酚或香豆雌甙的含量,使得大批量生产高产率的香豆雌酚。制得的香豆雌酚或香豆雌甙可用于各种应用,例如药物、食品或化妆品。
附图说明
图1展示了根据诱导处理和营养生长期,豆科植物的根部提取物中的香豆雌酚的含量;
图2展示了在将豆科植物的根部提取物溶解在水中之后,利用β-葡糖糖苷酶进行酶促反应,并利用HPLC分析酶促反应产生的沉淀物的结果;
图3对比了在进行酶促反应之前和之后,所述豆科植物的根部提取物中的香豆雌酚的含量。
具体实施方式
香豆雌酚(CMS, 3,9-二羟基-6H-苯并呋喃(3,2-c)(1)苯并吡喃-6-酮 C15H8O5,MW: 268.2)是香豆素类化合物,其结构与天然雌激素雌二醇或己烯雌酚类似,具有以下化学式1:
化学式1
香豆雌甙由化学式2表示。
化学式2
本发明提供一种制备香豆雌甙的方法,该方法在豆科植物播种后的预设营养生长期,用壳聚糖处理豆科植物或土壤。本发明还提供一种制备香豆雌酚的方法,该方法在豆科植物播种后的预设营养生长期,用壳聚糖处理豆科植物或土壤。壳聚糖可用于处理所述豆科植物的整个植物或其部分,例如种子、叶、茎、果实等。具体地,壳聚糖可用于处理根部。
根据本发明的一方面,豆科植物不作具体限定,只要是产生香豆雌甙和/或香豆雌酚的豆科植物即可。例如,可用于本发明的所述豆科植物可以是用于制作豆酱、豆腐或豆芽的豆科植物,用于煮饭的豆科植物,或者按其自身现状使用的豆科植物。 用于豆酱和豆腐的种类包括大豊(韩国品种名称登记(下文中省略) 申请公开号2003-940)、湖酱(申请公开号2003-950)、壮元(申请公开号2002-76)、 大潢(申请公开号2000-379)、sodam (sodam,申请公开号1999-933)、松鹤(申请公开号1999-936)、大元(韩国国家品种清单 (下文中省略)清单号01-0003-1997-38)、眞品(清单号01-0003-1997-26)、蛋白(清单号01-0003-1997-18)、豆油(清单号01-0003-1997-22)、新八达(清单号01-0003-1997-15)、太光(清单号01-0003-1997-12)、万里(清单号01-0003-1997-11)、长寿(清单号01-0003-1997-9)、无限(清单号01-0003-1997-7)、白云(清单号01-0003-1997-2)、saeal (清单号10-0003-1997-3)、黄金(清单号01-0003-1997-1)、长叶(清单号01-0003-1997-41)等等。用于豆芽的品种包括shinhwa-kong (申请公开号2009-982)、sowon-kong (申请公开号2000-376)、安平(申请公开号2003-939)、西南(申请公开号2003-948)、多彩(申请公开号2003-930)、小绿、小湖(申请公开号2002-78)、疏明(申请公开号1999-932)、多元(清单号01-0003-1997-40)、豊产(清单号01-0003-1997-34)、益山(清单号01-0003-1997-29)、小白(清单号01-2003-1997-31)、光安(清单号01-0003-1997-19)、短叶、银河(清单号01-0003-1997-6)等等。用于煮饭的品种包括靑磁(申请公开号2002-80)、黑靑(申请公开号2000-381)、褐味(申请公开号2000-380)、鲜黑(申请公开号1999-934)、geomjeong-kong (清单号01-2003-1997-17), 一品geomjeong-kong (清单号01-0003-1997-42)等等。按其自身现状使用的品种包括daol (申请公开号2003-931)、新绿(申请公开号2002-77)、saeol (申请公开号1999-938)、geomjeongol (清单号01-2003-1997-37)、seokyang-putkong (清单号01-0003-1997-25)、hwaeom-putkong (清单号01-0003-1997-21)、keunol (清单号01-2003-1997-14)等等。
根据本发明的一方面,在营养生长期的VE、VC、V1、V2、V3和V4期中的一个或多个期中,可用壳聚糖处理豆科植物。具体地,可以从VE至V3期用壳聚糖进行处理,更具体地从VE至V4期。VE期是发芽期,其中种子叶从土壤中长出,VC期为子叶期,其中初级幼苗叶子长出。V1期是初级幼苗期,其中初级幼苗叶子完全长出,V2期为第一复叶期,其中第一复叶完全长出,V3为第二复叶期,其中第二复叶完全长出。V4期为第三复叶期,其中第三复叶完全长出。
此外,可隔4-6天的间隔用壳聚糖处理豆科植物和/或土壤。
根据本发明的一方面,用于制备香豆雌酚或香豆雌甙的方法中使用的所述壳聚糖具体可以为低分子量、水溶性壳聚糖,更具体地为具有分子量为20000或更低、15000或更低、10000或更低、或者5000或更低的低分子量、水溶性壳聚糖。具体地,所述低分子量、水溶性壳聚糖的分子量可以是500或更大、1000或更大、2000或更大、或者5000或更大。壳聚糖的最重要的性质在于它溶于中性水,同时具有小分子量。壳聚糖是一种部分脱乙酰甲壳素,且是无毒的。虽然壳聚糖的浓度没有限定,但是具体地其浓度为0.01%或更高、更具体地0.3%或更高。对于和壳聚糖一起使用的溶剂是没有限制的,只要它能够很好地且安全地溶解壳聚糖即可。具体地,可以使用水(H2O)。
根据本发明的一方面,用于制备香豆雌甙的方法还可以包括制备所述豆科植物的提取物的步骤,具体地包括制备所述豆科植物的根部提取物的步骤。根据本发明的另一方面,所述用于制备香豆雌酚的方法还可以包括制备所述豆科植物的提取物的步骤,具体地制备所述豆科植物的根部提取物的步骤。
根据本发明的另一方面,所述用于制备香豆雌酚的方法可以包括制备香豆雌甙和香豆雌酚的步骤:在播种后的所述豆科植物的预设营养生长期,用壳聚糖处理所述豆科植物或土壤;以及对香豆雌甙脱糖基化的步骤:用选自酸、碱、酶和微生物中的一种或多种物质处理所述香豆雌甙。通过用壳聚糖处理所述豆科植物或土壤,可同时制备香豆雌甙和香豆雌酚,通过香豆雌甙的脱糖基化将香豆雌甙转化为香豆雌酚使得制备的香豆雌酚的产率得以显著提高。也就是说,根据本发明,与用壳聚糖处理所述豆科植物或土壤来单独制备香豆雌酚的方法相比,通过加入香豆雌甙的脱糖基化的步骤,可大规模制备香豆雌酚。
通过本领域通常使用的方法,例如热水提取、高压提取、回流提取、超声波提取等可获得所述提取物。
具体地,为了利用水或有机溶剂从所述豆科植物制备含有香豆雌甙的植物提取物,首先将1-6倍、具体约3倍的水,选自乙醇、甲醇、丁醇、乙醚、乙酸乙酯和氯仿中的一种或多种有机溶剂,或者所述有机溶剂和水的混合溶剂加入至所述豆科植物,例如所述豆科植物的根。然后,通过在室温下,伴随搅拌进行1-5次提取以去除油之后,将大约1-8倍、具体约4倍的水或所述有机溶剂加入至所得提取物,然后进行1-5次的回流提取。然后,在10-20℃下沉淀1-3天之后,进行过滤和离心,将滤出液与残渣分离。减压浓缩分离出的滤出液,将所得提取物悬浮于水中,利用例如乙醚去除色素。然后,用所述有机溶剂提取水层1-5次,减压浓缩所得有机溶剂层,以获得溶解于少量例如甲醇中的有机溶剂提取物。然后,干燥通过加入大量的例如乙酸乙酯产生的沉淀物,以获得本发明的所述豆科植物的含香豆雌甙的提取物。
然后,利用酸、碱、酶或产生酶的微生物通过水解由含有糖苷的提取物制备香豆雌酚。
当使用酸时,在将0.1-2N,具体的1N酸或酸和醇(具体地为40-60%的乙醇混合物)的混合物加入至所述提取物之后,在50-100℃、具体的80℃的水浴中加热回流所得混合物0.5-2小时,以获得水解产物。
所述酸可以是选自盐酸、硫酸和硝酸中的一种或多种酸,或者是所述酸与选自乙醇、甲醇和丁醇中的一种或多种醇的混合物。
当使用碱时,在溶解所述提取物,并加入0.1-2N,具体的1N碱或碱和醇(具体地为40-60%的丁醇混合物)之后,在50-100℃、具体的100℃的水浴中加热回流所得混合物1-12小时,以获得水解产物。
所述碱可以是选自氢氧化钠和氢氧化钾中的一种或多种碱,或者所述碱与选自乙醇、甲醇和丁醇中的一种或多种醇的混合物。
当使用酶时,在将所述提取物溶解于5-20倍,具体的约10倍的酸性缓冲液中之后,加入酶,将所得混合物在约35-40℃的水浴中加热搅拌约1-60小时。在薄层色谱确认底层完全消耗之后,将混合物在热水中(80-100℃)加热5-15分钟,以终止水解反应。
当使用产生所述酶的微生物时,在将所述提取物溶解于5-10倍、具体的约为10倍的离子水中之后,在110-130℃下进行30分钟的杀菌,将所得混合物冷却至25-35℃,然后根据所述混合物的体积接种5-10%的预培养的微生物。在25-35℃下培养2-5天之后,进行5000-10000rpm的离心处理,用蒸馏水洗涤几次回收的沉淀物,然后离心。
与酶或产生酶的微生物一样,也可以使用糖苷外切酶或产生糖苷外切酶的微生物。所述酶可以通过对糖苷进行脱糖基化分离香豆雌酚。
在利用所述酸、碱、酶或产生酶的微生物进行如上所述的水解之后,减压浓缩所述反应液,以去除溶剂。在将1-5倍的醇加入至残渣中并搅拌之后,通过过滤去除沉淀的盐,并减压浓缩滤出液,以获得香豆雌酚的粗产品,其经受硅胶柱色谱法(例如氯仿:甲醇=8:1)。
例如,可进行如下表1所描述的脱糖基化。
表1
利用选自酸、碱、酶或微生物中的一种或多种物质对含有香豆雌甙的物质的处理实际上也可以对所述豆科植物的提取进行。或者,在过滤或提纯所述豆科植物的提取物之后可进行所述处理,以制备香豆雌酚。
下面,本发明将详细地描述实验实施例。但是,以下实验实施例仅用作示例说明的目的,本领域技术人员可以理解本发明的保护范围并不限于此。
实验实施例1 在营养生长期用诱导剂对豆科植物的处理
培养豆科植物(大豆,Glycine max),同时在营养生长期的初始(VE)至V4期用低分子量、水溶性壳聚糖或米曲霉(Aspergillus oryzae)处理所述豆科植物和土壤。所述低分子量、水溶性壳聚糖适于处理土壤,因为它很好地溶解于水中,并且与其他诱导剂相比对人类没毒害。所述低分子量、水溶性壳聚糖(YWCTS-100)由Youngchipharm(KR)处购得。该壳聚糖溶解于水中,浓度为0.3%,隔5天的间隔喷洒在茎和土壤的周围。
米曲霉是一种食品发酵真菌,通过很多研究已知它具有优越的诱导效果,其对人类无毒害。干的米曲霉由Mediogen(KR)处购得。在用米曲霉处理的前一天,将10g糖溶解于1L水中,并与10g的干的米曲霉很好地混合。然后,在30℃的振荡培养箱中培养12小时之后,将所述混合物喷洒在豆类的茎和土壤周围。隔5天的间隔进行米曲霉的处理。对照组喷洒相同体积的纯化水。
实验实施例2 豆类根提取物的制备
在不同的营养成长期(从VE至V4期的6个期)收割用或不用壳聚糖和米曲霉处理的豆类的根,用纯化水洗涤,干燥,然后粉碎。将所得豆类根粉末(100g)添加至1L的70%乙醇水溶液中,并在室温下提取24小时。在用300目的滤布过滤后,利用配备有冷凝器的蒸馏装置在50℃下减压浓缩该滤出液,然后干燥以获得豆类根提取物。
实验实施例3 豆类根提取物中的香豆雌酚含量的分析
利用HPLC定量分析在实验实施例2中不同营养生长期获得的豆类根提取物中的香豆雌酚的含量。为了比较所述豆类根提取物中的香豆雌酚的含量,使用由Indofine 化学处购得的香豆雌酚作为标准物质。
图1展示了根据诱导剂处理和营养生长期的豆类根提取物中香豆雌酚的含量。可以看出,与没有用诱导剂处理的对照组相比,用诱导剂处理的豆类根提取物中的香豆雌酚的含量显著增加。具体地,香豆雌酚的含量在营养生长期的V3和V4期增加迅速。直至V4期,对于诱导剂处理的对照组,制得的香豆雌酚的含量为1.6mg/g提取物,当用米曲霉处理时该含量约增加了1.6倍至2.6mg/g,而当用壳聚糖处理时约增加了2倍至约3.2mg/g。
实验实施例4 通过香豆雌甙的脱糖基化增加香豆雌酚的含量
从实验实施例1中确定,在壳聚糖处理的豆类根中制备香豆雌甙,香豆雌甙是一种香豆雌酚糖苷。通过对壳聚糖处理的豆类根提取物中的香豆雌甙进行脱糖基化,可进一步增加提取物中香豆雌酚的含量。
为了脱糖基化,利用β-葡萄糖苷酶进行酶促反应,利用HPLC分析从酶促反应制得的沉淀物。从表2中可见,发现由于提取物中的香豆雌甙通过脱糖基化被转化为香豆雌酚,豆类根提取物中的香豆雌酚的含量得到显著增加。具体地,与豆类根提取物相比,豆类根提取物酶促反应沉淀物中的香豆雌酚在57.00分钟周围的HPLC峰约增加了15倍,而44.00分钟周围的香豆雌甙峰轻微减少。
图3中比较了在酶促反应之前和之后豆类根提取物中的香豆雌酚的含量。作为酶促反应的结果,通过壳聚糖的处理,豆类根提取物中的香豆雌酚的含量约增加了3.5倍。
Claims (2)
1.一种用于制备香豆雌酚的方法,该方法包括:
在土壤中培养豆科植物;
在豆科植物的营养生长期的VE至V4期的任一期,用壳聚糖处理所述豆科植物的茎或土壤,以获得香豆雌甙或香豆雌酚;
制备所述豆科植物的提取物;和
利用酶处理所述香豆雌甙,来进行香豆雌甙的脱糖基化,
其中所述豆科植物为大豆,
其中所述壳聚糖为分子量5,000或更小的水溶性壳聚糖,
其中每隔4-6天进行一次壳聚糖处理。
2.根据权利要求l所述的方法,其特征在于,所述豆科植物的提取物为所述豆科植物的根部提取物。
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