CN105837647A - 酚类化合物及其应用 - Google Patents
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Abstract
本发明公开了一种酚类化合物及其应用,化合物结构为其中R为其中R1、R2为H、OH、‑O‑CH3、‑O‑CH3‑CH3或‑O‑CH3‑CH3‑CH3。本发明的酚类化合物具有很好的抗炎作用,具有高效、低毒的优点,有望开发为新的抗炎药物。
Description
技术领域
本发明属于医药及保健食品领域,具体涉及一种酚类化合物及其应用。
背景技术
炎症(inflammation):具有血管***的活体组织对损伤因子所发生的防御反应为炎症。它是机体对于刺激的一种防御反应,表现为红、肿、热、痛和功能障碍。炎症,可以是感染引起的感染性炎症,也可以不是由于感染引起的非感染性炎症。
炎症是常见疾病,在各方面影响着我们的健康。一系列的医学研究表明炎症与动脉硬化、心脏病、中风、癌症、糖尿病、老年性痴呆、牙周炎、骨关节炎、哮喘、偏头疼、肠易激综合征、慢性疲劳综合征等都密切相关。由此可见,炎症影响着整个身体。
天然药物尤其是来源于植物的药物具有化学结构多样性和生物活性多样性,一直是人类预防和治疗疾病的主要来源。临床上应用的许多药物都直接或间接来源于天然产物,天然产物不仅可以作为药物半合成的前体物,而且可以作为药物化学合成的的模板,为新药设计提供新思路。天然产物已成为发现新药物或先导化合物的主要源泉之一。
榴莲(Durio zibethinus Murr.)为木棉科(Bombacaceae)榴莲属(Durio)植物。榴莲原产于马来西亚,后传入菲律宾、斯里兰卡、泰国、越南和缅甸等国,中国海南也有少量栽种。榴莲具有丰富的营养价值,被称为亚洲“水果之王”。传统药理研究表明,榴莲可以缓解老年人皮肤瘙痒,对于妇女痛经也有一定的改善作用。现代药理作用研究表明,榴莲乙醇粗提物具有抗氧化和抗炎作用。榴莲化学成分研究较少,因而其化学成分值得进一步研究和开发利用。同时,榴莲果皮在大多数情况下被当成有机垃圾处理,所以本发明在环保方面有一定的价值。
发明内容
本发明的目的在于提供一种酚类化合物。
本发明的目的在于提供上述酚类化合物在炎症预防和治疗中的应用。
本发明所采取的技术方案是:
酚类化合物,其结构通式为:
其中R为
进一步的,所述R1为H、OH、-O-CH3、-O-CH3-CH3或-O-CH3-CH3-CH3。
进一步的,所述R2为H、OH、-O-CH3、-O-CH3-CH3或-O-CH3-CH3-CH3。
进一步的,所述R1为-O-CH3。
进一步的,所述R2为-O-CH3。
上述酚类化合物在制备抗炎药物中的应用。
上述酚类化合物在制备抗炎保健品中的应用。
上述酚类化合物在制备抗炎化妆品中的应用。
本发明的有益效果是:
本发明的酚类化合物对小鼠RAW264.7细胞具有较好的抗炎作用,该化合物具有高效、低毒的优点,有望开发为新的抗炎药物;或者用于制备预防和治疗炎症的保健食品及化妆品。
附图说明
图1为本发明化合物1的1H-NMR图谱;
图2为本发明化合物1的13C-NMR图谱;
图3为本发明化合物1的HMQC图谱;
图4为本发明化合物1的HMBC图谱;
图5为本发明化合物1的1H-1H COSY图谱;
图6为本发明化合物2的1H-NMR图谱;
图7为本发明化合物2的HMBC图谱;
图8为本发明化合物3的1H-NMR图谱;
图9为本发明化合物3的HMBC图谱。
具体实施方式
下面结合具体实施例对本发明作进一步的说明,但并不局限于此。
实施例1酚类化合物的提取
1)取榴莲果皮20kg,用70%乙醇加热回流提取5次,每次3小时,合并提取液减压回收溶剂,得总浸膏;
2)将总浸膏用水混悬,用环己烷等体积萃取4次,除去脂溶性杂质,然后经氯仿,乙酸乙酯等体积萃取5次,有机层减压蒸馏得到粗提物。
3)取乙酸乙酯萃取层50g,通过采用硅胶柱色谱、ODS中低压柱色谱、反相高效液相色谱等分离方法,分离得到本发明化合物2和3。
本发明通过理化常数和现代波谱学技术手段(HR-ESI-MS,1D-NMR,2D-NMR)鉴定以上3个化合物的结构,化合物1为Durianol A,化合物2为Durianol B,化合物3为DurianolC,化合物1~3的结构鉴定过程如下所述。
实施例2酚类化合物的鉴定
(1)化合物1(Durianol A)的鉴定
化合物1为白色无定形粉末;其HR-ESI-MS m/z 461.1407[M+Na]+(calcd.forC21H26O10,461.1424),确定分子式为C20H18O9。在1H-NMR(图1)中,化学位移δH 6.32和δH 7.95为一组相互耦合的质子信号,耦合常数为9.5Hz,由此推测结构中含有香豆素母核。同时,氢谱中含有一组糖的质子信号和一组脂肪链质子信号,结合13C-NMR(图2),可以进一步验证结构推测。化合物经过酸水解,糖衍生,GC分析,确定糖为D-葡萄糖。化合物平面结构经HMQC(图3)、HMBC(图4)和1H-1H COSY(图5)可以进一步确认。与糖六位碳上羟基相连的脂肪链信号经HMQC和HMBC确定为2-甲基丁酸的片段,化合物经过水解,衍生化,与标准品S-2-甲基丁酸衍生化产物经HPLC分析对照,确定为S-2-甲基丁酸。由此化合物被确定为Durianol A,其结构见表1,核磁数据见表2。
(2)化合物2(Durianol B)的鉴定
化合物2为白色针状晶体;其HR-ESI-MS m/z 437.1443[M+Na]+(calcd.forC19H26O10,437.1424),确定分子式为C19H26O10。在1H-NMR(图6)中,高场区的质子信号与化合物1一致,由此推测化合物2中含有2-甲基丁酸,其绝对构型经同样方法确定为S-构型。同时在1H-NMR中,可以明显看到一组1,3,4三取代苯环的质子信号。化合物糖信号,同样经过酸水解,衍生化,GC分析,确定为D-葡萄糖。三个结构片段经HMBC谱图(图7)找到对应的连接位置。化合物被确定为Durianol B,其结构见表1,化合物2的1H-NMR和13C-NMR数据见表2。
(3)化合物3(Durianol C)的鉴定
化合物3为白色片状晶体;其HR-ESI-MS m/z 411.1684[M+H]+(calcd.forC20H26O9,411.1655),确定分子式为C20H26O9。同化合物2的1H-NMR比较,发现化合物3的1H-NMR(图8)的质子信号只有在芳香区有差别,故推测化合物中含有葡萄糖和2-甲基丁酸的片段信号。在1H-NMR中,芳香区有一组相互耦合的质子信号,根据耦合常数和峰积分面积推测为苯环上对位取代后的两组对称的质子信号,结合碳谱,推测含有一个反式肉桂酸的片段。由HMBC谱图(图9)得到三个片段的连接位置,确定化合物为Durianol C。其结构见表1,化合物3的1H-NMR和13C-NMR数据见表2。
表1本发明3个化合物的结构
表2本发明的3个化合物的1H-NMR和13C-NMR数据(DMSO-d6)
下面对本发明提取鉴定的化合物1~3作进一步药理活性检测。
细胞毒性试验
实验方法:MTT法
将小鼠RAW264.7细胞接种于96孔板中,培养24h后加入待测试样品,再培养48h后用MTT法测定样品对细胞生长的抑制率。细胞生长抑制率按下述公式计算,并用CalcuSyn软件计算被测试样品的半数抑制浓度(IC50)
细胞生长抑制率(%)=[(空白对照-样品组)/空白对照]×100%。
实验结果见表3
表3:本发明化合物对小鼠RAW264.7细胞的生长抑制作用
样品名称 | 半数抑制浓度IC50(μM) |
化合物1 | >50.00 |
化合物2 | >50.00 |
化合物3 | >50.00 |
实验结果:从表3的实验数据可知,化合物1~3对小鼠RAW264.7细胞的生长抑制作用小,其IC50值均大于50.00μM,说明本发明酚类化合物1~3具有低毒的优点。
抗炎试验
实验方法:将RAW264.7细胞接种于96孔板中,培养24h后加入LPS(脂多糖)。接着不同组分别加入不同浓度的样品(本发明化合物1~3、阳性药物吲哚美辛),空白组加入等体积溶剂。50μL细胞培养液混合等体积Griess reagent I加入上诉96孔板,接着加入Griessreagent II。酶标仪测定各组样品在546nm波长下的吸收值,带入如下公式计算NO抑制率,并用CalcuSyn软件计算被测试样品的半数抑制浓度(IC50)。
NO抑制率(%)=[1-(样品组/空白组)]×100%。
表4本发明化合物1~3对LPS刺激细胞RAW264.7产生NO的抑制作用
样品名称 | 半数抑制浓度IC50(μM) |
化合物1 | 36.32±1.39 |
化合物2 | 38.07±2.40 |
化合物3 | 41.26±0.44 |
阳性药物(吲哚美辛) | 47.40±4.50 |
实验结果:从表4的实验数据可知,化合物1~3对脂多糖LPS刺激小鼠RAW264.7细胞产生NO具有较好的抑制作用,其半数抑制浓度IC50分别为36.32±1.39μM、38.07±2.40μM、41.26±0.44μM,均优于阳性药物吲哚美辛的47.40±4.50μM。说明本发明酚类化合物1~3具有较好的抗炎作用。
结合以上实验及其实验结果,表明本发明酚类化合物1~3具有高效、低毒的优点,有望开发为新的抗炎药物;或者用于制备预防和治疗炎症的保健食品及化妆品。
上述实施例为本发明较佳的实施方式,但本发明的实施方式并不受上述实施例的限制,其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本发明的保护范围之内。
Claims (8)
1.酚类化合物,其结构通式为:
其中R为
2.根据权利要求1所述的酚类化合物,其特征在于:所述R1为H、OH、-O-CH3、-O-CH3-CH3或-O-CH3-CH3-CH3。
3.根据权利要求1所述的酚类化合物,其特征在于:所述R2为H、OH、-O-CH3、-O-CH3-CH3或-O-CH3-CH3-CH3。
4.根据权利要求2所述的酚类化合物,其特征在于:所述R1为-O-CH3。
5.根据权利要求3所述的酚类化合物,其特征在于:所述R2为-O-CH3。
6.权利要求1~5任一所述酚类化合物在制备抗炎药物中的应用。
7.权利要求1~5任一所述酚类化合物在制备抗炎保健品中的应用。
8.权利要求1~5任一所述酚类化合物在制备抗炎化妆品中的应用。
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CN103599145A (zh) * | 2013-10-29 | 2014-02-26 | 贵阳中医学院 | 铁筷子提取物及其中有效成分的分离方法和所得化合物 |
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