CN117510453A - 一种土坛树树皮提取物的制备方法及分离的杜松烷型倍半萜类化合物与应用 - Google Patents
一种土坛树树皮提取物的制备方法及分离的杜松烷型倍半萜类化合物与应用 Download PDFInfo
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Abstract
本发明提供一种土坛树树皮提取物的制备方法及分离的杜松烷型倍半萜类化合物与应用,本发明以土坛树树皮为原料,以乙酸乙酯为提取溶剂制得土坛树树皮乙酸乙酯提取部位,土坛树树皮乙酸乙酯提取部位通过石油醚‑乙酸乙酯溶剂、甲醇溶剂洗脱制得土坛树提取物,土坛树树皮提取物具有抗炎、抗肿瘤、治疗糖尿病的功效,本发明从土坛树树皮提取物中分离出两个新的高度氧化的杜松烷型倍半萜类化合物A1‑A2和已知化合物A3‑A5,新化合物A1和化合物A2具有抗肿瘤功效,化合物A3具有抗炎功效,化合物A4和化合物A5显示抑制α‑葡萄糖苷酶活性的功效。
Description
技术领域
本发明涉及天然植物提取物领域,特别涉及一种土坛树树皮提取物的制备方法及分离的杜松烷型倍半萜类化合物与应用。
背景技术
土坛树(Alangium salviifolium),又名割舍罗,是八角枫科(Alangiaceae)八角枫属(Alangium)植物。在我国,主要分布于广东、广西南部沿海地区及海南省。主治祛风活血,解毒催吐,消炎止痛。黎族民间用土坛树的根皮作呕吐剂和解毒剂,对麻风病、皮肤病、痔疮、痢疾、蛇咬伤和湿疹具有一定疗效;土坛树的果实呈鲜红色,味道甜美,可直接食用,可用于泌尿和结石等治疗。
国内外对于土坛树的化学成分研究较少,其化学成分主要包括生物碱、三萜、倍半萜、黄酮(苷)等,且都具有较好的生物活性。Nobuo Yagi(Isolation and biologicalactivity of a novel cadinane-type sesquiterpenoid from the essential oil ofAlangium salviifolium,J.Oleo Sci.2014,63(12):1223-1229.)一文中报道了土坛树中倍半萜的抗氧化作用Phanruethai Pailee(Bioactive Cardinane Sesquiterpenes fromthe Stems of Alangium salviifolium,Chem-Asian J,2015,10:910-914.)一文中报道了土坛树中倍半萜的抗肿瘤作用。但目前从土坛树中发现的具有抗肿瘤作用的倍半萜类化合物较少。本发明旨在对土坛树化学成分进一步分离研究,以期得到新的具有抗肿瘤作用的倍半萜类化合物。
发明内容
鉴于此,本发明提出一种土坛树树皮提取物的制备方法及分离的杜松烷型倍半萜类化合物与应用,解决上述问题。
本发明的技术方案是这样实现的:
一种土坛树树皮提取物的制备方法,包括以下步骤:
(1)将干燥的土坛树树皮粉碎制得土坛树树皮粉末,土坛树树皮粉末用乙酸乙酯浸提,合并浸提液,减压浓缩得到土坛树树皮乙酸乙酯提取部位浸膏;
(2)将步骤(1)得到的土坛树树皮乙酸乙酯提取部位浸膏采用石油醚-乙酸乙酯溶剂体系经过硅胶柱层析,制得土坛树树皮粗提物1;
(3)将土坛树树皮粗提物1采用ODS柱层析分离,洗脱剂为甲醇-水溶剂,按照5∶95~100∶0(V/V)的梯度进行洗脱,根据极性大小共得12个组分,即Fr.1-Fr.12,合并Fr.1-Fr.18得到土坛树树皮提取物。
进一步的,所述的土坛树树皮提取物的制备方法,还包括以下步骤:
S1:将Fr.4经高效液相色谱分析,发现其在240nm,280nm,340nm有强的吸收峰,符号高度氧化杜松烷型倍半萜类化合物的特征,使用正相硅胶柱层析,洗脱剂为石油醚-丙酮=10:1~1:0的混合溶剂,洗脱3~6个柱体积,收集流分,根据极性大小得到9个组分,即Fr.4A-Fr.4I;
S2:将Fr.4E经高效液相色谱分离制备,得到杜松烷型倍半萜类化合物A1;
S3:将Fr.2经高效液相色谱分离制备,得到杜松烷型倍半萜类化合物A2和化合物A5;
S4:Fr.4A经凝胶柱纯化,用甲醇洗脱得到杜松烷型倍半萜类化合物A3;
S5:Fr.4C经凝胶柱纯化,用甲醇洗脱,再经重结晶得到杜松烷型倍半萜类化合物4。
进一步的,所述的土坛树树皮提取物的制备方法,步骤(1)中,所述土坛树树皮粉末和乙酸乙酯的质量比为6-8kg:1L,浸提次数为2-4次,浸提时间为1-3h/次,在35~40℃下超声浸提。
进一步的,所述的土坛树树皮提取物的制备方法,步骤(2)中,采用石油醚-乙酸乙酯溶剂体系,按照100∶0~0∶100(V/V)的梯度进行洗脱,每2000mL收集流分,浓缩石油醚-乙酸乙酯溶剂体系为70∶30(V/V)的组分,制得土坛树树皮粗提物1。
进一步的,所述的土坛树树皮提取物的制备方法,步骤(3)中,土坛树树皮粗提物1进行ODS柱层析分离,洗脱剂为MeOH-H2O溶剂,按照5:95~100:0(V/V)的梯度进行洗脱,每500mL收集流分,浓缩各流分,通过TLC检测,合并相同组分后得到12个组分Fr.1-Fr.12。
进一步的,所述的土坛树树皮提取物的制备方法,步骤S2中,所述高效液相色谱分离的色谱条件为:色谱柱为Waters C18,流速为2-3mL/min,流动相为体积比为70:30的MeCN:H2O。
进一步的,所述的土坛树树皮提取物的制备方法,步骤S3中,所述高效液相色谱分离的色谱条件为:色谱柱为Waters C18,流速为2-3mL/min,流动相为体积比为58:42的MeCN:H2O。
进一步的,杜松烷型倍半萜类化合物A1-A5的结构式如式A1-A5所示:
进一步的,所述土坛树树皮提取物在制备抗炎、抗肿瘤、糖尿病药物中的应用。
进一步的,所述土坛树树皮提取物制备的抗肿瘤的药物为抑制人慢性髓系白血病细胞、人胃癌、人肝癌细胞和人肺癌细胞。
进一步的,所述杜松烷型倍半萜类化合物A1和化合物A2在制备抑制人慢性髓系白血病细胞、人胃癌、人肝癌细胞和人肺癌细胞药物中的应用。
进一步的,所述杜松烷型倍半萜类化合物A3在制备治疗和/或预防抗炎药物中的应用。
进一步的,所述杜松烷型倍半萜类化合物A4和化合物A5在制备治疗糖尿病药物中的应用。
与现有技术相比,本发明的有益效果是:
本发明以土坛树树皮为原料,以乙酸乙酯为提取溶剂制得土坛树树皮乙酸乙酯提取部位,土坛树树皮乙酸乙酯提取部位通过石油醚-乙酸乙酯溶剂、甲醇-水溶剂洗脱经硅胶、ODS分级制得土坛树提取物,土坛树树皮提取物具有抗炎、抗肿瘤、治疗糖尿病的功效。
本发明从土坛树树皮提取物中分离出两个新的高度氧化的杜松烷型倍半萜类化合物A1和化合物A2,经过试验验证,新化合物A1和化合物A2具有抑制人慢性髓系白血病细胞、人胃癌、人肝癌细胞和人肺癌细胞的功效。
本发明从土坛树树皮提取物分离出杜松烷型倍半萜类化合物A3、化合物A4、和化合物A5,经过试验验证,化合物A3具有抗炎功效,化合物A4和化合物A5抑制α-葡萄糖苷酶活性的功效,发现了杜松烷型倍半萜类化合物A3-A5新的应用价值。
附图说明
图1:化合物A1的1H-NMR谱(CDCl3)
图2:化合物A1的13C-NMR谱(CDCl3)
图3:化合物A1的DEPT(135°)谱(CDCl3)
图4:化合物A1的1H-1H COSY谱(CDCl3)
图5:化合物A1的HSQC谱(CDCl3)
图6:化合物A1的HMBC谱(CDCl3)
图7:化合物A1的HRESIMS谱
图8:化合物A2的1H-NMR谱(CD3OD-d4)
图9:化合物A2的13C-NMR谱(CD3OD-d4)
图10:化合物A2的DEPT(135°)谱(CD3OD-d4)
图11:化合物A2的1H-1H COSY谱(CD3OD-d4)
图12:化合物A2的HSQC谱(CD3OD-d4)
图13:化合物A2的HMBC谱(CD3OD-d4)
图14:化合物A2的HRESIMS谱
具体实施方式
为了更好理解本发明技术内容,下面提供具体实施例,对本发明做进一步的说明。
本发明实施例所用的实验方法如无特殊说明,均为常规方法。
本发明实施例所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
实施例1土坛树树皮提取物的制备方法
(1)将30kg干燥的土坛树树皮粉碎后,加入4L的乙酸乙酯升温至40℃超声浸提4次,每次2h,合并提取液,减压浓缩制得土坛树树皮乙酸乙酯提取部位浸膏。
(2)将步骤①得到的土坛树树皮乙酸乙酯提取部位浸膏经过硅胶柱层析,采用石油醚-乙酸乙酯溶剂体系,按照洗脱梯度分别为100:0、90:10、80:20、70:30、60:40、50:50、40:60、30:70、20:80、10:90、0:100的梯度进行洗脱,每2000mL收集流分,浓缩各流分,通过TLC检测,浓缩石油醚-乙酸乙酯溶剂体系70∶30(V/V)的流分,制得土坛树树皮粗提物1;
(3)土坛树树皮粗提物1进行ODS柱层析分离,洗脱剂为MeOH-H2O溶剂,按照5:95、10:90、20:80、30:70、40:60、50:50、60:40、70:30、80:20、90:10、100:0(V/V)的梯度进行洗脱,每500mL收集流分,浓缩各流分,通过TLC检测,合并相同组分后得到12个组分Fr.1-18,合并Fr.1-Fr.12得到土坛树树皮提取物。
实施例2杜松烷型倍半萜类化合物A1-A5的制备方法
(1)将实施例1得到的Fr.4先经正相硅胶柱层析,洗脱剂为石油醚-丙酮的混合体系,按照10:0、9:1、8:2、7:3、6:4、5:5(V/V)的梯度进行洗脱,洗脱4个柱体积,收集流分,合并相同组分后得到9个组分Fr.4A-Fr.4I;
(2)Fr.4E经高效液相色谱HPLC分离制备,色谱柱为Waters C18(9.4×250mm,4.6μm),流速为2mL/min,流动相为MeCN:H2O=70:30得到化合物A1。
(3)实施例1中Fr.2经高效液相色谱HPLC分离制备,色谱柱为Waters C18(9.4×250mm,4.6μm),流速为2mL/min,流动相为MeCN:H2O=58:42得到化合物A2(3.0mg),得到化合物A2和化合物A5。
(4)Fr.4A经凝胶柱纯化,用甲醇洗脱得到化合物3。
(5)Fr.4C经凝胶柱纯化,用甲醇洗脱,再经重结晶得到化合物5。
试验例1
运用波谱(1H NMR,13C NMR,HSQC,HMBC)和MS等现代结构鉴定技术,确定实施例2所得化合物A1和A2的化学结构。
结构鉴定数据如下:
化合物A1:淡黄色粉末,易溶于甲醇或氯仿。经高分辨质谱HRESI(-)MS(m/z381.2980[M+Na]+,理论值381.2984)确定其分子式为C19H18O7;根据1H,13C 及二维核磁共振数据确定其结构,骨架类型为杜松烷型倍半萜,将其命名为alansalene A,其1H和13C NMR数据归属见表1。[400MHz(1H),100MHz(13C),溶剂:CDCl3]。
化合物A2:为黄色固体粉末,易溶于甲醇。经高分辨质谱HRESI(-)MS(m/z243.1021[M-H]-,理论值243.1021)确定其分子式为C15H16O3;根据1H,13C及二维核磁共振数据确定其结构,骨架类型为杜松烷型倍半萜,将其命名为2,7-dihydroxy-4-isopropyl-1-methyl-6-naphthaldehyde。其1H和13C NMR数据归属见表1。[400MHz(1H),100MHz(13C),溶剂:CD3OD-d4]。
表1化合物的1H-NMR和13C-NMR数据[δ(ppm),J(Hz)]
试验例2杜松烷型倍半萜类化合物A1和化合物A2抗肿瘤活性试验
1.1实验材料细胞:SGC-7901(人胃癌癌细胞)、K562(人白血病细胞)、A-549(人肺癌细胞),BEL(人肝癌细胞)。
细胞培养液:含10%胎牛血清(FBS)的DMEM培养基,MTT。
阳性对照:盐酸阿霉素。
1.2实验方法
(1)接种细胞:将10%新生牛血清的培养液(DMEM)配成单个细胞悬液,加100μL(每孔约5×103个细胞)细胞液到96孔板内,培养12小时,待其贴壁。
(2)加药:加100μL待测样,设定加6孔,以40μg/ml浓度为初筛浓度,根据初筛结果设定5个梯度浓度进行复筛,每种设定3个平行复孔。
(3)显色:将完成上述加药步骤的96孔板在37℃条件下培养48小时,取出给每孔加20μL的MTT溶液。继续培养后弃去上层清液,给每孔加150μL的DMSO溶液,使结晶物完全融解。
(4)比色:在490nm波长下用酶标仪读取各孔的吸光值,记录数值。
(5)数据处理:细胞的抑制率%=[(对照组的OD值-样品组的OD值)/对照组OD的值]×100%,代入数值算出IC50值。
表2化合物A1和A2抑制肿瘤细胞增殖结果
杜松烷型倍半萜类化合物A1和化合物A2的抗肿瘤结果如表2所示,从结果可知,化合物A1对A-549(人肺癌细胞)表现出一定的体外抑制作用,化合物A2对K562(人白血病细胞)表现出较好的体外抑制作用。
试验例3杜松烷型倍半萜类化合物A3抗炎试验
实验仪器与材料
(1)实验仪器
全波长多功能酶标仪,化学发光检测仪(Analytik Jena、美国),电子天平、高温灭菌锅、96孔板、移液枪、移液枪吸头、恒温培养箱。
(2)实验材料
细胞:RAW264.7巨噬细胞。
细胞培养液:DMEM(10%胎牛血清和1%青霉素链霉素)培养基。
试剂:LPS(美国Sigma公司);FBS(美国Gibco公司);DMEM(美国Gibco公司);NO试剂盒(上海碧云天公司);MTT(美国Sigma公司);地塞米松(美国Sigma公司)
5.1.2实验方法
(1)MTT法测定细胞活力
用MTT法测定化合物对RAW264.7细胞的细胞毒性作用,RAW 264.7巨噬细胞在含10%胎牛血清和1%青霉素链霉素的DMEM培养基中培养,培养环境为空气含量为95%、CO2含量为5%的加湿培养箱,37℃。将RAW 264.7细胞以每孔1×105细胞的密度接种于96孔板中。细胞在37℃培养12h后,用化合物A3和Fr.4组分处理细胞24h。随后向孔中加入20μL MTT原液(5μg/mL)。孵育4h后,吸除上清液。最后,将每个孔中的甲晶体溶解在DMSO(150μL)中,并使用酶标仪(BD,Bioscience USA)在570nm波长下测量吸光度。这些数据表示为与各自对照相比的活细胞的平均百分比。
细胞存活率(%)=测定孔OD值/空白孔OD值×100%
(2)NO抑制活性测试
采用Griess法,测试分离得到的部分化合物对脂多糖(LPS)诱导的RAW264.7细胞上清液中一氧化氮(NO)释放,地塞米松(DEX)作为阳性对照。将RAW 264.7细胞以每孔2×105细胞的密度接种于96孔板中,37℃培养12h后,用化合物A3、土坛树树皮提取物和DEX(50μg/mL)预处理细胞1h,然后用LPS(1μg/mL)刺激细胞24h。24h后,测定培养基中NO的积累量。将细胞上清液(50μL)加入等体积的Griess试剂Ⅰ和试剂Ⅱ。用酶标仪在540nm波长处测定吸光度。
表3杜松烷型倍半萜类化合物A3抗炎试验结果
名称 | IC50(μM)b |
化合物A3 | 2.98±0.11 |
土坛树树皮提取物 | 42.72±0.56 |
地塞米松 | 39.62±0.12 |
实验结果表明,从土坛树树皮中分离出来的杜松烷型倍半萜类化合物A3具有抗炎作用。
试验例4杜松烷型倍半萜类化合物A4和化合物A5抑制α-葡萄糖苷酶活性试验
实验仪器与试剂:
96孔板、电子天平、移液枪、恒温培养箱、酶标仪(ELx800)、恒温振荡器、阿卡波糖、α-葡萄糖苷酶、PNPG、无水碳酸钠、0.1mol/L pH 6.8磷酸盐缓冲液(PBS)。
实验方法:
α-葡萄糖苷酶经0.1mol/L缓冲液(pH=6.8)稀释为0.2U/mL待用,PNPG浓度为2.5mmol/L,样品及阿卡波糖用0.1mol/L缓冲液(pH=6.8)配制得1.0mmol/L,0.5mmol/L,0.25mmol/L和0.1mmol/L待用。
本实验通过96孔那培养板进行测定,总反应体系为200μL,测定时依次加入50μL磷酸缓冲液(0.1mol/L,pH=6.8)和10μLα-葡萄糖苷酶(0.2U/mL),随后加入20μL抑制剂,于37℃水浴静置15min,再加入20μL浓度为2.5mmol/LPNPG,于37℃反应15min后,然后加入100μLNa2CO3溶液(2.5mmol/L)使反应终止,混合均匀后在405nm波长处测定吸光度(A)值。平行测定3次,取平均值。计算样品对α-葡萄糖苷酶的抑制率:抑制率(%)=[1-(A405nm样品-A405nm空白)/A405nm对照]×100%。(A405nm样品表示样品的A值,A405nm空白表示空白的A值,A405nm对照表示排除样品干扰的A值)。
阿卡波糖,Genistein均为阳性对照。
表4杜松烷型倍半萜类化合物A4和化合物A5抑制α-葡萄糖苷酶活性试验结果
名称 | IC50(μM)b |
化合物A4 | 111.85±1.80 |
化合物A5 | 18.55±0.68 |
土坛树树皮提取物 | 88.43±2.15 |
阿卡波糖 | 478.75±27.14 |
Genisteinc | 17.14±0.77 |
实验结果表明,从土坛树树皮中分离出来的杜松烷型倍半萜类化合物A4和化合物A5具有抑制α-葡萄糖苷酶活性的功效。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (10)
1.一种土坛树树皮提取物的制备方法,其特征在于:包括以下步骤:
(1)将干燥的土坛树树皮粉碎制得土坛树树皮粉末,土坛树树皮粉末用乙酸乙酯浸提,合并浸提液,减压浓缩制得土坛树树皮乙酸乙酯提取部位浸膏;
(2)将步骤(1)得到的土坛树树皮乙酸乙酯提取部位浸膏采用石油醚-乙酸乙酯溶剂体系经过硅胶柱层析,制得土坛树树皮粗提物1;
(3)将土坛树树皮粗提物1采用ODS柱层析分离,洗脱剂为甲醇-水溶剂,按照5∶95~100∶0(V/V)的梯度进行洗脱,根据极性大小共得12个组分,即Fr.1-Fr.12,合并Fr.1-Fr.12得到土坛树树皮提取物。
2.如权利要求1所述的土坛树树皮提取物的制备方法,其特征在于,还包括以下步骤:
S1:将Fr.4使用正相硅胶柱层析,洗脱剂为体积比为10:1~1:0的石油醚-丙酮混合溶剂,洗脱3~6个柱体积,收集流分,根据极性大小得到9个组分,即Fr.4A-Fr.4I;
S2:将Fr.4E经高效液相色谱分离制备,得到杜松烷型倍半萜类化合物A1;
S3:将Fr.2经高效液相色谱分离制备,得到杜松烷型倍半萜类化合物A2和化合物A5;
S4:Fr.4A经凝胶柱纯化,用甲醇洗脱得到杜松烷型倍半萜类化合物A3;
S5:Fr.4C经凝胶柱纯化,用甲醇洗脱,再经重结晶得到杜松烷型倍半萜类化合物4。
3.如权利要求1所述的土坛树树皮提取物的制备方法,其特征在于,步骤(1)中,所述土坛树树皮粉末和乙酸乙酯的料液比为1kg∶1-1.2L,浸提次数为2-4次,浸提时间为1-3h/次,在35~40℃下超声浸提,步骤(2)中,采用石油醚-乙酸乙酯溶剂体系,按照100∶0~0∶100(V/V)的梯度进行洗脱,每2000mL收集流分,浓缩石油醚-乙酸乙酯溶剂体系为70∶30(V/V)的组分,制得土坛树树皮粗提物1,步骤(3)中,土坛树树皮粗提物1采用ODS柱层析分离,洗脱剂为MeOH-H2O溶剂,按照5∶95~100∶0(V/V)的梯度进行洗脱,每500mL收集流分,浓缩各流分,根据极性大小共得12个组分,即Fr.1-Fr.12。
4.如权利要求2所述的土坛树树皮提取物的制备方法,其特征在于,步骤S2中,所述高效液相色谱分离的色谱条件为:色谱柱为Waters C18,流速为2-3mL/min,流动相为体积比为70:30的MeCN:H2O,步骤S3中,所述高效液相色谱分离的色谱条件为:色谱柱为Waters C18,流速为2-3mL/min,流动相为体积比为58:42的MeCN:H2O。
5.权利要求2所述杜松烷型倍半萜类化合物,其特征在于,所述杜松烷型倍半萜类化合物A1-A5的结构式如式A1-A5所示:
6.权利要求1所述土坛树树皮提取物在制备抗炎、抗肿瘤、糖尿病药物中的应用。
7.如权利要求6所述的应用,其特征在于,所述抗肿瘤的药物包括抑制人慢性髓系白血病细胞、人胃癌、人肝癌细胞和人肺癌细胞。
8.权利要求5所述杜松烷型倍半萜类化合物A1和化合物A2在制备抑制人慢性髓系白血病细胞、人胃癌、人肝癌细胞和人肺癌细胞活性的药物中的应用。
9.权利要求5所述杜松烷型倍半萜类化合物A3在制备治疗和/或预防抗炎药物中的应用。
10.权利要求5所述杜松烷型倍半萜类化合物A4和化合物A5在制备治疗糖尿病药物中的应用。
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