CN1081192C - 一种鞘类脂糖苷化合物及其提取方法 - Google Patents
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Abstract
本发明涉及一种从中国南海海绵Iotrochota ridley中提取、分离的新鞘类脂糖苷化合物。本发明所述化合物的化学名为:1-(β-D-吡喃葡糖氧基)-3,4-二羟基-2-[(4’Z)-2’-羟基二十四碳烯酰胺基-4’]-十八烷。命名为:Iotroridoside A,其化学结构式如下:该化合物是以工业乙醇从中国南海海绵Iotrochota ridley中提取、浓缩,并以正丁醇等溶剂萃取,经硅胶柱层析和适当溶剂淋洗,再以葡聚糖凝胶柱层析得白色粉状物。该化合物具有新型骨架结构,即其支链二十四碳烯酰胺基具有独特的双键片段,这是以往所获得的此类天然产物所没有的。同时该化合物还具有极强的肿瘤细胞毒活性。因此,具有良好的应用前景。
Description
本发明涉及一种从中国南海海绵Iotrochota ridley中分离、提取的新鞘类脂糖苷化合物。
海绵是一种低等的多细胞动物,种类繁多,分布极广,以海产为主。自七十年代以来,人们已从海绵中发现了许多结构独特的萜类、生物碱、大环内酯和糖苷等化合物。近几年来,由于有效成分的分离、纯化技术的显著改进,尤其是600兆核磁共振仪等现代先进分析仪器的出现以及各种二维谱技术的迅猛发展,使海洋天然产物中的一些结构较复杂的化合物,特别是鞘类脂糖苷化合物的结构鉴定工作在九十年代才取得一些重要进展。经药理试验表明,鞘类脂糖苷化合物大多具有抗真菌和抗肿瘤等生理活性。因而,它们是一类具有广阔应用前景的天然产物。本发明所涉及的化合物经IR、EIMS、FABMS、1HNMR、13CNMR、GCOSY、TOCSY、HMQC和HMBC等现代物理手段和化学方法确定结构如下:
该化合物的化学名称为::1-(B-D-吡喃葡糖氧基)-3,4-二羟基-2-[(4′Z)-2′-羟基二十四碳烯酰胺基-4′]-十八烷。命名为:Iotroridoside A,其物理常数如下:
vKBr max(cm-1):3363,2919,2850,2287,1629,1536,1465,1376,1168,1035,898,721,605;δ1H(C3D5N,TMS)ppm:8.54(1H,d,J=9Hz,NH),5.90(1H,dt,J=10.2,7.2Hz,H4’),5.60(1H,dt,J=10.8,7.2Hz,H5’),5.24(1H,m,H2),4.93(1H,d,J=8.4Hz,H1”),4.68(1H,dd,J=10.2,4.2Hz,H1a),4.62(1H,m,H2’),4.50(1H,dd,J=10.8,4.2Hz,H1b),4.45(1H,dd,J=12,2.4Hz,H6”a),4.31(1H,dd,J=12,5.4Hz,H6”b),4.27(1H,dd,J=12,4.8Hz,H3),4.19(1H,m,H4”),4.16(1H,m,H4),4.15(1H,m,H3”),3.97(1H,m,H2”),3.84(1H,m,H5”),3.00(1H,m,H3’a),2.82(1H,m,H3’b),2.22(1H,m,H5a),2.17(2H,m,H6’),1.88(2H,m,H5b,H6a),1.66(1H,m,H6b),1.42(2H,m,H7),1.35(2H,m,H7’),1.34~1.20(26CH2),1.25(H17,H23’),1.24(H16,H22’),0.86(6H,t,J=6.6Hz,18-CH3,24’-CH3);δ13C(C5D5N,TMS)ppm:174.98(Cl’),132.39(C5’),126.27(C4’),105.53(C1”),78.52(C3”),78.43(C5”),75.85(C3),75.13(C2”),72.57(C4”),72.48(C2’),71.51(C4),70.42(C1),72.57(C4”),72.48(C2’),71.51(C4),70.42(C1),62.65(C6”),51.80(C2),34.22(C5),33.56(C3’),32.14(C16,C22’),30.37~29.90(23CH2),29.70(C7),27.90(C6’),26.54(C6),22.94(C17,C23’),14.28(C18,C24’);FABMS得分子量843,EIMS(m/z):568,490,458,406,370,356,328,307,265,225,179,145,123,111,97,83,70(100%),57,55,43
该化合物的提取方法如下:以中国南海海绵为原料,将晒干的海绵用酒精浸泡、抽提,将抽提物浓缩至浆状物,然后将其分散在适量的水中,再以等量的乙酸乙酯和正丁醇依次萃取,将所获得的正丁醇可溶物进行三次硅胶柱层析和两次葡聚糖凝胶LH-20柱层析得白色粉状物,即该化合物。
生理活性试验表明,该化合物对小鼠L1210白血病细胞的细胞毒作用EC50值为80ng/ml。
本发明所述的化合物,不但具有新型双键片段的酰胺骨架结构,而且具有极强的肿瘤细胞的细胞毒活性。因此,本发明所涉及的新化合物具有十分重要的理论价值和应用价值。
实施例:一、分离提纯:
中国南海海绵Iotrochota ridley,晒干(2.2g)切碎后用95%工业酒精(5kg)于室温下浸泡提取三次,合并提取物并减压浓缩至浆状物,将此浆状物均匀分散于500ml水中,分别用等量的乙酸乙酯和正丁醇萃取三次,正丁醇萃取物经减压浓缩得黑色浆状物23g。
上述浆状物经硅胶(150g,Merk 70~230目)柱层析(φ=4.6×35cm),以500ml不同比例的氯仿-甲醇(100%,90%,85%,80%,70%)梯度洗脱,获得A、B、C、D、E五个初组分。C组分(1g)经两次硅胶(80g,30g,青岛海洋化工分厂,300~400目)柱层析(φ2.4×48,φ1.6×48,洗脱剂:90%氯仿-甲醇)得粗产物45mg。将此粗产物再经二次葡聚糖凝胶LH-20(30%氯仿-甲醇)柱层析,得白色粉状物29.6mg。二、结构鉴定1.红外3363cm-1处的宽峰说明分子含羟基,1629、1536cm-1等处的中等偏弱吸收峰显示分子可能含仲酰胺片段。2.1HNMR、13CNMR(C5D5N,ppm)显示分子含有一根邻二取代双键(δH5.90,dt,J=10.2,7.2Hz,δC126.7和δH5.60,dt,J=10.8,7.2Hz,δC132.39),因两烯氢间的偶合常数小于12Hz,故双键的立体构型为顺式。另有10个连氧或氮的亚甲基(或次甲基)及两个甲基(δH0.86,6H,t,J=6.6Hz,δC14.28)。δH4.93(1H,d,J=8.4Hz)以及δC105.53是特征的葡萄糖异头碳氢信号,暗示分子可能含葡糖环。δH8.54(1H,d,J=9Hz,NH)以及δC174.98(酰胺羰基)指明分子含有一个仲酰胺片段,恰与红外提供的信息吻合。另外,δH1.34~1.20,δC30.37~29.90都有一个巨大的亚甲基信号峰,说明分子含一根或一根以上的长脂肪链。3.GCOSY同核相关谱显示分子有三个偶合体系:①从异头氢(1″)出发找偶合点可连接出一个六元糖环结构(1″→6″),再由HMQC异核相关谱可找出其相应的δC值(105.53,75.13,78.52,72.57,78.43和62.65ppm),将其δC值与文献值对照,可知是β-D-吡哺葡糖环。②从仲酰胺氢出发可推导出一个植物鞘氨醇(phytosphingosine)片段(1→6),同样可由HMQC定出相应的δC值。③从双键氢(4′,5′)出发可推出一不饱和脂肪长链(1′→mCH2),其中有一连氧亚甲基,可能与酰胺羰基相连。HMBC指出,NH与C=O、C=O与H2′有2JCH远程偶合,C1与H1″有3JCH远程偶合,由此可将三个偶合体系连成一片,得到如下初步结构:
上述结构与文献报导的一些鞘类脂糖苷化合物类似,但结构上又有独特的地方,即4′位有双键,这是以前所没出现过的,因此是新化合物。该化合物的TOCSY、HMBC等相关谱则进一步证实了这一结构,见表1。表1 IotroridosideA的δ1H,δ13C,TOCSY和HMBC数据表
4.根据FABMS得分子量843,推算出m+n=25,同时由1HNMR的氢积分面积也可推得m+n=25,但m,n仍需进一步确定。我们应用如下化学方法解决了这一问题。5.取样品5mg,在6.5ml82%的甲醇水溶液(含1NHCl)中进行酸解反应。常压下85℃左右回流12小时。产物用石油醚萃取三次(5ml×3),合并石油醚层,用去离子水洗二遍,Na2SO4干燥,过夜。浓缩石油醚溶液,得产物3.5mg。TLC显示此产物仍混有少量反应物,因此再对产物进行硅胶(10克,青岛海洋化工分厂,300~400目)柱层析(φ1.2×43,洗脱剂:80%石油醚-乙酸乙酯)得纯产物2.0mg。作EIMS,得数据如下:396(M+),378(M-H2O),337(M-COOCH3),304,139,125,111,103(γ裂解),90(100%,β裂解),83,69,57,55,43。由该质谱数据及实施例二(3)中所提供的信息综合推得水解产物的结构式如下:6.因n=15,则m=25-15=10,由此我们便可确定该化合物的结构式如下:
序号 | δ1H,ppm | δ13C,ppm | 1H-1HGCOSY | TOCSY | HMBC |
1a | 4.68 | 70.42 | 1b,2 | 1b,2,3,NH | 3,1″ |
1b | 4.50 | 1a,2 | 1a,2,3,NH | ||
2 | 5.24 | 51.80 | 1,3,NH | 1,3,NH,4 | 1,3 |
3 | 4.27 | 75.85 | 2,4 | 1,2,4,5,6 | 4 |
4 | 4.16 | 71.51 | 3,5 | 2,3,5,6,7,(CH2)n | 4,3 |
5a | 2.22 | 34.22 | 5b,4,6 | 3,4,5b,6,7,(CH2)n | 3 |
5b | 1.88 | 5a,4,6 | 3,4,5a,6,7,(CH2)n |
6a | 1.88 | 26.54 | 6b,5,7 | 3,4,5,6b,7,(CH2)n | |
6b | 1.66 | 6a,5,7 | 3,4,5,6a,7,(CH2)n | ||
16 | 1.24 | 32.14 | 17,18 | ||
17 | 1.25 | 22.94 | 18 | ||
18 | 0.86 | 14.28 | 16,17 | ||
1′ | / | 174.98 | / | / | NH,2′ |
2′ | 4.62 | 72.48 | 3′ | 3′,4′,5′ | 3′ |
3′a | 3.00 | 33.56 | 3′b,2′,4′ | 2′,3′b,4′,5′,6′ | 5′ |
3′b | 2.82 | 3′a,2′,4′ | 2,3′a,4′,5′,6′ | ||
4′ | 5.90 | 126.27 | 3′,5′,6′ | 2′,3′,5′,6′,7′,(CH2)n | 3′,6′ |
5′ | 5.60 | 132.39 | 4′,6′ | 2′,3′,4′,6′,7′,(CH2)n | 3′,6′ |
6′ | 2.17 | 27.90 | 5′,7′ | 3′,4′,5′,7′,(CH2)n | 4′,7′ |
22′ | 1.24 | 32.14 | 23′,24′ | ||
23′ | 1.25 | 22.94 | 24′ | ||
24′ | 0.86 | 14.28 | 22′,23′ | ||
1″ | 4.93 | 105.53 | 2″ | 2″,3″,4″,5″ | 2″,1 |
2″ | 3.97 | 75.13 | 1″,3″ | 1″,3″,4″,5″,6″ | 3″ |
3″ | 4.15 | 78.52 | 2″,4″ | 1″,2″,4″,5″,6″ | 2″,4″ |
4″ | 4.19 | 72.57 | 3″,5″ | 1″,2″,3″,5″,6″ | 6″ |
5″ | 3.84 | 78.43 | 4″,6″ | 1″,2″,3″,4″,6″ | 4″ |
6″a | 4.45 | 62.65 | 6″b,5″ | 2″,3″,4″,5″,6″b | |
6″b | 4.31 | 6″a,5″ | 2″,3″,4″,5″,6″a | ||
NH | 8.54 | / | 2 | 1,2,3,4 | / |
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