黑桑化学成分及生物活性研究
摘要
黑桑(Morus nigra)为桑科(Moraceae)桑属(Morus)植物,分布于新疆等地。桑(M.alba)始载于《神农本草经》,为传统中药,树皮、枝叶、果实等皆可入药,具有降压、抗菌、降糖、抗病毒等作用。桑科桑属植物全世界约16种,我国有11种,包括桑M.alba,蒙桑M.mongolica,光叶桑M.macroura,鸡桑M.australis,华桑M.cathayanna,长穗桑M.wittioru,川桑M.notabilis,裂叶桑M.trlobata,荔波桑M.liboensis,吉隆桑M.sorrata,黑桑M.nigra。国内外对桑属植物的研究主要集中于桑(M.alba),黑桑(M.nigra)研究较少。本组近年开展了光叶桑、蒙桑、鸡桑、华桑的研究,研究发现桑属植物主要含有黄酮、二苯乙烯、苯骈呋喃等酚性成分。
为了寻找黑桑中的抗炎抗氧化活性成分,我们对黑桑(M.nigra.)95%乙醇提取物的化学成分进行了系统研究,共得到31个化合物,其中8个新化合物(带有*的化合物)。Mornigrol A(1)*,Mornigrol B(2)*,Mornigrol C(3)*,Mornigrol D(4)*,Mornigrol E(5)*,Mornigrol F(6)*,Mornigrol G(7)*,Mornigrol H(8)*,Oleanolic acid(9),Ursolic acid(10),Methyloleanolate(11),Octadecyl(E)-Ferulate(12),Octacosyl(E)-Ferulate(13),β-sitosterol(14),Morusin(15),Cylomurosin(16),Kuwanon C(17),Cyclocommunol(18),Dihydrokaempferol(19),Norartocarpetin(20),Apingenin(21),Quercetin(22),Albafuran A(23),Albanin A(24),Albanin E(25),Oxyresveratrol(26),Moracin M(27),Albafuran B(28),Mulberofuran L(29),Albafuran C(30),Daucosterol(31)。已知化合物中12,13为首次从桑属植物中得到;13个化合物为首次从黑桑中分离得到,分别是化合物9,11,18,19,21-25,27-29,31通过质谱、核磁、紫外、红外等光谱手段及化学方法确定了它们的结构。
药理筛选表明:黑桑茎皮95%乙醇提取物的氯仿＼乙酸乙酯部分显示一定的抗氧化活性。在10~(-5)mol/L时,化合物Albafuran A、Albafuran B、Mornigrol D、AlbafuranC、Mulberofuran L对Fe~(2+)-半胱氨酸诱导的肝微粒体脂质过氧化物的抑制率均大于50%。在抗炎活性筛选中,采用抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放的模型,Albanin A、Mornigrol C、Mornigrol D均明显抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放,抑制率大于50%(P＜0.05),显示一定的抗炎活性。
Morus nigra belonds to the genus Morus of the family Moraceae, distributed in the XinJiang Province.M.alba is a kind of Chinese traditional medicine,which was first recorded in Shengnong Bencao Jing, and its barks,branches,leaves and fruit can be used as traditional Chinese medicine.The genus Morushas sixteen species in the world,eleven of them grow in many provinces of China.The chemical constituents of morus were focus on M.alba,M.australis,M.mongolica,M.bombycis,M.lhou,M. insignis et al.Until now,there were no such reports on M.nigra.Its constituents were main]y flavone,stilbene and benzofuran derivatives and these compounds had hypotensive,antibiotics,hypoglycemic and antivirus activities.
In order to search antihypertension,antivirus,antibacterial, antifungi,antioxidation,antiinflammation,and anticancer activities compounds,the chemical constituents of the barks of M.nigra were carefully studied.About 31 compounds were isolated,they were Mornigrol A(1)*, Mornigrol B(2)*,Mornigrol C(3)*,Mornigrol D(4)*,Mornigrol E (5)*,Mornigrol F(6)*,Mornigrol G(7)*,Mornigrol H(8)*,Oleanolic acid(9),Ursolic acid(10),Methyl Oleanolate(11),Octadecyl(E)-Ferulate (12),Octacosyl(E)-Ferulate(13),β-sitosterol(14),Morusin(15), Cyclomurosin(16),Kuwanon C(17),Cyclocommunol(18),Dihydrokaempferol (19),Norartocarpetin(20),Apingenin(21),Quercetin(22),Albafuran A(23), Albanin A(24),Albanin E(25),Oxyresveratrol(26),Moracin M(27), Albafuran B(28),Mulberofuran L(29),Albafuran C(30),Daucosterol(31).1-8 were the new compounds.12 and 13 were isolated from the genus Morus and the plant for the first time.Other thirtyteen compounds(9,11,18,19, 21-25,27-29,31) were isolated from M.nigra for the first time.Their structures were mainly elucidated by spectroscopic evidence,such as MS, NMR,UV,IR and chemical methods.
The results of bioassays displayed;(1) Albafuran A,Albafuran B, Mornigrol D,Albafuran C,Mulberofuran L from the EtOAc soluble part of nigra,inhibited the production of the lipid peroxide induced by Fe~(2+)-Cys system in the Liver microsomes LPO obviously,with inhibitory rates more than 50%at a concentrate of 10~(-5)mol/L.(2) On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF,three compounds Albanin A,Mornigrol C and Mornigrol D,isolated from K nigra,were revealed the anti-inflammation activity with the inhibitory rates more than 50%at a concentration of 10~(-5)mol/L.
为了寻找黑桑中的抗炎抗氧化活性成分,我们对黑桑(M.nigra.)95%乙醇提取物的化学成分进行了系统研究,共得到31个化合物,其中8个新化合物(带有*的化合物)。Mornigrol A(1)*,Mornigrol B(2)*,Mornigrol C(3)*,Mornigrol D(4)*,Mornigrol E(5)*,Mornigrol F(6)*,Mornigrol G(7)*,Mornigrol H(8)*,Oleanolic acid(9),Ursolic acid(10),Methyloleanolate(11),Octadecyl(E)-Ferulate(12),Octacosyl(E)-Ferulate(13),β-sitosterol(14),Morusin(15),Cylomurosin(16),Kuwanon C(17),Cyclocommunol(18),Dihydrokaempferol(19),Norartocarpetin(20),Apingenin(21),Quercetin(22),Albafuran A(23),Albanin A(24),Albanin E(25),Oxyresveratrol(26),Moracin M(27),Albafuran B(28),Mulberofuran L(29),Albafuran C(30),Daucosterol(31)。已知化合物中12,13为首次从桑属植物中得到;13个化合物为首次从黑桑中分离得到,分别是化合物9,11,18,19,21-25,27-29,31通过质谱、核磁、紫外、红外等光谱手段及化学方法确定了它们的结构。
药理筛选表明:黑桑茎皮95%乙醇提取物的氯仿＼乙酸乙酯部分显示一定的抗氧化活性。在10~(-5)mol/L时,化合物Albafuran A、Albafuran B、Mornigrol D、AlbafuranC、Mulberofuran L对Fe~(2+)-半胱氨酸诱导的肝微粒体脂质过氧化物的抑制率均大于50%。在抗炎活性筛选中,采用抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放的模型,Albanin A、Mornigrol C、Mornigrol D均明显抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放,抑制率大于50%(P＜0.05),显示一定的抗炎活性。
Morus nigra belonds to the genus Morus of the family Moraceae, distributed in the XinJiang Province.M.alba is a kind of Chinese traditional medicine,which was first recorded in Shengnong Bencao Jing, and its barks,branches,leaves and fruit can be used as traditional Chinese medicine.The genus Morushas sixteen species in the world,eleven of them grow in many provinces of China.The chemical constituents of morus were focus on M.alba,M.australis,M.mongolica,M.bombycis,M.lhou,M. insignis et al.Until now,there were no such reports on M.nigra.Its constituents were main]y flavone,stilbene and benzofuran derivatives and these compounds had hypotensive,antibiotics,hypoglycemic and antivirus activities.
In order to search antihypertension,antivirus,antibacterial, antifungi,antioxidation,antiinflammation,and anticancer activities compounds,the chemical constituents of the barks of M.nigra were carefully studied.About 31 compounds were isolated,they were Mornigrol A(1)*, Mornigrol B(2)*,Mornigrol C(3)*,Mornigrol D(4)*,Mornigrol E (5)*,Mornigrol F(6)*,Mornigrol G(7)*,Mornigrol H(8)*,Oleanolic acid(9),Ursolic acid(10),Methyl Oleanolate(11),Octadecyl(E)-Ferulate (12),Octacosyl(E)-Ferulate(13),β-sitosterol(14),Morusin(15), Cyclomurosin(16),Kuwanon C(17),Cyclocommunol(18),Dihydrokaempferol (19),Norartocarpetin(20),Apingenin(21),Quercetin(22),Albafuran A(23), Albanin A(24),Albanin E(25),Oxyresveratrol(26),Moracin M(27), Albafuran B(28),Mulberofuran L(29),Albafuran C(30),Daucosterol(31).1-8 were the new compounds.12 and 13 were isolated from the genus Morus and the plant for the first time.Other thirtyteen compounds(9,11,18,19, 21-25,27-29,31) were isolated from M.nigra for the first time.Their structures were mainly elucidated by spectroscopic evidence,such as MS, NMR,UV,IR and chemical methods.
The results of bioassays displayed;(1) Albafuran A,Albafuran B, Mornigrol D,Albafuran C,Mulberofuran L from the EtOAc soluble part of nigra,inhibited the production of the lipid peroxide induced by Fe~(2+)-Cys system in the Liver microsomes LPO obviously,with inhibitory rates more than 50%at a concentrate of 10~(-5)mol/L.(2) On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF,three compounds Albanin A,Mornigrol C and Mornigrol D,isolated from K nigra,were revealed the anti-inflammation activity with the inhibitory rates more than 50%at a concentration of 10~(-5)mol/L.
引文
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