长穗桑化学成分和生物活性研究
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摘要
长穗桑为桑科桑属植物,又名黔鄂桑、黄蚕桑、花桑,是重要农作物栽培桑的野生近缘种,产于我国南部地区。其根、枝、叶、果实均可作药用。对长穗桑茎皮95%乙醇提取物和水提取物分别进行抗氧化和降糖活性筛选,结果表明,95%乙醇提取物的乙酸乙酯部位有显著的抗氧化活性;95%乙醇提取物的丙酮、甲醇部位以及水提取物有明显的降糖活性。
本论文运用多种色谱技术和波谱技术,并结合化学方法,对长穗桑茎皮的乙醇提取物和水提取物分别进行了系统的化学成分研究,并对其中的单体化合物进行了生物活性筛选。长穗桑茎皮采自广西壮族自治区金秀县,由广西中医学院刘寿养教授鉴定。
从长穗桑茎皮中共分离鉴定了74个化合物,包括乙醇提取物中得到63个,以及水提取物中得到11个。其中31个化合物(1-31)为新化合物,其余均为首次从该植物中分离得到。从乙醇提取物中分离并鉴定的63个化合物中,包括24个Diels-Alder型加合物,30个2-苯基苯并呋喃类衍生物,6个黄酮类化合物,3个二苯乙烯类化合物,分别为:wittiorumin A(1),wittiorumin B(2),wittiorumin C(3),wittiorumin D(4),wittiorumin E(5),wittiorumin F(6),wittiorumin G(7),wittifuran A(8),wittifuran B(9),wittifuran C(10),wittifuran D(11),wittifuran E(12),wittifuran F(13),wittifuran G(14),wittifuran H(15),wittifuran I(16),wittifuran J(17),wittifuran K(18),wittifuran L(19),wittifuran M(20),wittifuran N(21),wiuifuran O(22),wittifuranP(23),wittifuran Q(24),wittifuran R(25),wittifuran S(26),wittifuran T(27),wittifuranU(28),wittifuran V(29),wittifuran W(30),wittifuran X(31),chalcomoracin(32),mongolicin F(33),mulberrofuran J(34),mulberrofuran K(35),mulberrofuran G(36),guangsangon L(37),kuwanon J(38),kuwanon X(39),guangsangon G(40),guangsangon B(41),guangsangon D(42),kuwanon P(43),albafuran C(44),sorocein A(45),mulberrofuran E(46),mulberrofuran F(47),mulberrofuran O(48),moracin M(49),moracin C(50),2-(3,5-dihydroxyphenyl)-5,6-dihydroxybenzofuran(51),moracin P(52),mulberroside C(53),austrafuran C(54),quercetin(55),5,7,3',4'-tetrahydroxy-3-metho-xyflavone(56),norartocarpanone(57),dihydrokaempferol(58),euchrenone a_7(59),morachalcone A(60),resveratrol(61),oxyresveratrol(62),4'-prenyloxyresveratrol(63).
从长穗桑茎皮水提取物中分离并鉴定的11个化合物中,包括7个多羟基生物碱类化合物,2个酰胺类化合物,1个氨基酸,以及甜菜碱,分别为:1-deoxynoiirimycin(64),fagomine(65),3-epi-fagomine(66),1,4-dideoxy-1,4-imino-D-arabinitol(67),2-O-α-D-galactopyranosyl-1-deoxynojirimycin(68),4-O-β-D-glucopyranosyl-fagomine(69),1,4-dideoxy-1,4-imino-(2-O-β-D-glucopyranosyl)-D-arabinitol(70),(2S)-citrullina-mide(71),grateloupinamide(72),asparagic acid(73),betaine(74)。
另外,结合降糖活性筛选,分别对95%乙醇提取物的丙酮、甲醇部位进行分离后发现,具有抑制α-葡萄糖苷酶活性部分的物质基础均为多羟基生物碱类化合物。
通过对长穗桑茎皮乙醇提取物中分离到的15个2-苯基苯并呋喃类化合物(化合物8-11,13-14,17-18,21-27)的正离子ESI-MS/MS~n质谱进行分析后发现,化合物中含有异戊烯基,栊牛儿基等取代基,一般发生苄基裂解。此外,这些取代基往往与邻位羟基环合形成六元氧环,此类化合物的ESI-MS/MS~n质谱裂解因六元氧环部分的差异而有所不同。而且,不同结构类型的2-苯基苯并呋喃类化合物裂解后产生特征离子,可用于此类化合物的快速检测以及在线鉴定。
长穗桑茎皮乙醇提取物乙酸乙酯部分中分离到的29个化合物(化合物1-3,8,10,12-14,16-17,21-23,25-26,33-36,39-41,43,45,47,49-51,56),浓度为10~(-5)M时,对Fe~(2+)-半胱氨酸诱导的肝微粒体脂质过氧化有抑制活性(抑制率>50%)。在抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放的模型上,11个化合物(化合物10-11,16,32,34,49-51,54,60,62)具有抗炎活性(抑制率大于50%,P<0.05)。
采用MTT法测定了长穗桑茎皮中分离得到的56个化合物对五种人肿瘤细胞(A549:人肺腺癌细胞;Bel-7402:人肝癌细胞;BGC-823:人胃癌细胞;HCT-8:人结肠癌细胞;A2780:人卵巢癌细胞)的抑制作用。结果显示26个化合物(化合物8,10-11,13-14,16,21-26,29,32-36,39,47,50-52,56,61,62),对人癌细胞有抑制作用;水提取物中得到的单体化合物(化合物64-73)均无抗肿瘤活性(超过10μg/mL,认为无活性)。
对长穗桑茎皮水提取物中得到的10个化合物进行α-葡萄糖苷酶抑制活性(蔗糖底物)筛选,测试结果显示7个多羟基生物碱(化合物64-70)以及1个酰胺类化合物(化合物72)有较强的抑制α-葡萄糖苷酶的活性,40μg/mL时抑制率均大于80%。其中化合物64的IC_(50)为0.07μM;化合物68的IC_(50)为0.39μM,与阳性对照阿卡波糖(Acarbose)(IC_(50)=0.52μM)相当;化合物69,70,72的IC_(50)值在1-5μM。
Morus wittiorum is the species belonging to the genus Morus of Moraceae.As the relative of the cultivated mulberry,it mostly distributes in the southern area of China.Its roots,twigs,leaves and fruits as well are used as the folk medicine.The bioactive screening on the 95%ethanol extract and water extract of the stem bark of M.wittiorum resulted in:the ethyl acetate fraction from the 95%ethanol extract displayed significant anti-oxidative activity;the acetone fraction and methanol fraction of the 95%ethanol extract and the water extract as well showed remarkable inhibitory activity againstα-glucosidase.
The 95%ethanol extract and water extract of the stem bark of M.wittiorum were investigated respectively on their chemical constituents systematically by various kinds of chromatographic methods.The isolates were elucidated on the basis of spectroscopic analysis and chemical methods as well.Some of them in sufficient amount were assayed for their bioactivities.The stem bark of M.wittiorum were collected from Jinxiu county of Guangxi province and identified by professor Shou-Yang Liu,Guangxi College of Traditional Chinese Medicine.
Among the seventy-four compounds isolated from the stem bark of M.wittiorum, thirty-one compounds(1-31) are new compounds,and the rest were isolated from this plant for the first time.Sixty-three compounds were isolated and identified from the 95% ethanol extract of the stem bark of M.wittiorum,including twenty-four Diels-Alder type adducts,thirty 2-arylbenzofuran derivatives,six flavonoids,three stilbenes.These compounds are listed as follows:wittiorumin A(1),wittiorumin B(2),wittiorumin C(3), wittiorumin D(4),wittiorumin E(5),wittiorumin F(6),wittiorumin G(7),wittifuran A (8),wittifuran B(9),wittifuran C(10),wittifuran D(11),wittifuran E(12),wittifuran F (13),wittifuran G(14),wittifuran H(15),wittifuran I(16),wittifuran J(17),wittifuran K (18),wittifuran L(19),wittifuran M(20),wittifuran N(21),wittifuran O(22),wittifuran P(23),wittifuran Q(24),wittifuran R(25),wittifuran S(26),wittifuran T(27),wittifuran U(28),wittifuran V(29),wittifuran W(30),wittifuran X(31),chalcomoracin(32), mongolicin F(33),mulberrofuran J(34),mulberrofuran K(35X mulberrofuran G(36), guangsangon L(37),kuwanon J(38),kuwanon X(39),guangsangon G(40), guangsangon B(41),guangsangon D(42),kuwanon P(43),albafuran C(44),sorocein A (45),mulberrofuran E(46),mulberrofuran F(47),mulberrofuran O(48),moracin M(49), moracin C(50),2-(3,5-dihydroxyphenyl)-5,6-dihydroxybenzofuran(51),moracin P(52), mulberroside C(53),austrafuran C(54),quercetin(55),5,7,3',4'-tetrahydroxy-3-metho-xyflavone (56),norartocarpanone(57),dihydrokaempferol(58),euchrenone a_7(59), morachalcone A(60),resveratrol(61),oxyresveratrol(62),4'-prenyloxyresveratrol(63).
Eleven compounds were obtained and identified from the water extract of the stem bark of M.wittiorum,including seven polyhydroxyalkalines,two acylamides,one amino acid and betaine.The corresponding compounds are displayed as 1-deoxynojirimycin (64),fagomine(65),3-epi-fagomine(66),1,4-dideoxy-1,4-imino-D-arabinitol(67), 2-O-α-D-galactopyranosyl-1 -deoxynojirimycin(68),4-O-β-D-glucopyranosyl-fagomine (69),1,4-dideoxy-1,4-imino-(2-O-β-D-glucopyranosyl)-D-arabinitol(70),(2S)-citrullina-mide (71),grateloupinamide(72),asparagic acid(73),betaine(74).
In addition,the investigations under the guiding of bioassay on the acetone fraction and methanol fraction of 95%ethanol extract respectively indicated that polyhydroxyalkalines were bioactive substances possessing inhibitory activity againstα-glucosidase.
The positive ESI-MS/MS~n spectra of fifteen 2-arylbenzofuran derivatives (compounds 8-11,13-14,17-18,21-27) were studied.Based on the data analysis,some fragmentation patterns were found.2-arylbenzofuran derivatives with substituents such as isoprenyls,geranyls and so on,usually performed the benzyl fragmentation.Moreover, the substituents often formed the pyran or dihydropyran ring with vicinal hydoxy,which resulted in different fragmentation.In addition,different fragmentation pathway produced various diagnostic ions,which were found for the first time in this thesis,could be used to detect or characterize 2-arylbenzofuran derivatives rapidly.
Within the compounds isolated from the stem bark of M.wittiorum,twenty-nine compounds(compounds 1-3,8,10,12-14,16-17,21-23,25-26,33-36,39-41,43,45,47, 49-51,56) inhibited the production of the lipid peroxide induced by Fe~(2+)-Cys system in the liver microsomal obviously,with inhibitory rates more than 50%at a concentration of 10~(-5) M.On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF,eleven compounds(compounds 10-11,16,32,34,49-51,54,60,62) displayed antiinflammatory activity with the inhibitory rates more than 50%at a concentration of 10~(-5) M.
Twenty-six compounds(compounds 8,10-11,13-14,16,21-26,29,32-36,39,47, 50-52,56,61-62) obtained from the stem bark of M.wittiorum displayed moderate inhibitory activity against five human tumor cells(A549,Bel-7402,BGC-823,HCT-8 and A2780) by MTT method.However,compounds isolated from water extract (compounds 64-73) did not show inhibitory activity against any of the five tumor cells (IC_(50)>10μg/ml).
The inhibition againstα-glucosidase was performed for ten compounds isolated from water extract of the stem bark of M.wittiorum.The resulst showed that seven polyhydroxyalkalines(compounds 64-70) and one acylamide(compound 72) possessed significant inhibition agaistα-glucosidase,with inhibitory rates over 80%at a concentration of 40μg/mL.Especially for compound 64,IC_(50)= 0.07μM;the IC_(50) values of compound 68 was 0.39μM,which was comparative to the positive control acarbose (IC_(50) = 0.52μM).And the IC_(50) values of compounds 69,70,72 were within 1-5μM.
本论文运用多种色谱技术和波谱技术,并结合化学方法,对长穗桑茎皮的乙醇提取物和水提取物分别进行了系统的化学成分研究,并对其中的单体化合物进行了生物活性筛选。长穗桑茎皮采自广西壮族自治区金秀县,由广西中医学院刘寿养教授鉴定。
从长穗桑茎皮中共分离鉴定了74个化合物,包括乙醇提取物中得到63个,以及水提取物中得到11个。其中31个化合物(1-31)为新化合物,其余均为首次从该植物中分离得到。从乙醇提取物中分离并鉴定的63个化合物中,包括24个Diels-Alder型加合物,30个2-苯基苯并呋喃类衍生物,6个黄酮类化合物,3个二苯乙烯类化合物,分别为:wittiorumin A(1),wittiorumin B(2),wittiorumin C(3),wittiorumin D(4),wittiorumin E(5),wittiorumin F(6),wittiorumin G(7),wittifuran A(8),wittifuran B(9),wittifuran C(10),wittifuran D(11),wittifuran E(12),wittifuran F(13),wittifuran G(14),wittifuran H(15),wittifuran I(16),wittifuran J(17),wittifuran K(18),wittifuran L(19),wittifuran M(20),wittifuran N(21),wiuifuran O(22),wittifuranP(23),wittifuran Q(24),wittifuran R(25),wittifuran S(26),wittifuran T(27),wittifuranU(28),wittifuran V(29),wittifuran W(30),wittifuran X(31),chalcomoracin(32),mongolicin F(33),mulberrofuran J(34),mulberrofuran K(35),mulberrofuran G(36),guangsangon L(37),kuwanon J(38),kuwanon X(39),guangsangon G(40),guangsangon B(41),guangsangon D(42),kuwanon P(43),albafuran C(44),sorocein A(45),mulberrofuran E(46),mulberrofuran F(47),mulberrofuran O(48),moracin M(49),moracin C(50),2-(3,5-dihydroxyphenyl)-5,6-dihydroxybenzofuran(51),moracin P(52),mulberroside C(53),austrafuran C(54),quercetin(55),5,7,3',4'-tetrahydroxy-3-metho-xyflavone(56),norartocarpanone(57),dihydrokaempferol(58),euchrenone a_7(59),morachalcone A(60),resveratrol(61),oxyresveratrol(62),4'-prenyloxyresveratrol(63).
从长穗桑茎皮水提取物中分离并鉴定的11个化合物中,包括7个多羟基生物碱类化合物,2个酰胺类化合物,1个氨基酸,以及甜菜碱,分别为:1-deoxynoiirimycin(64),fagomine(65),3-epi-fagomine(66),1,4-dideoxy-1,4-imino-D-arabinitol(67),2-O-α-D-galactopyranosyl-1-deoxynojirimycin(68),4-O-β-D-glucopyranosyl-fagomine(69),1,4-dideoxy-1,4-imino-(2-O-β-D-glucopyranosyl)-D-arabinitol(70),(2S)-citrullina-mide(71),grateloupinamide(72),asparagic acid(73),betaine(74)。
另外,结合降糖活性筛选,分别对95%乙醇提取物的丙酮、甲醇部位进行分离后发现,具有抑制α-葡萄糖苷酶活性部分的物质基础均为多羟基生物碱类化合物。
通过对长穗桑茎皮乙醇提取物中分离到的15个2-苯基苯并呋喃类化合物(化合物8-11,13-14,17-18,21-27)的正离子ESI-MS/MS~n质谱进行分析后发现,化合物中含有异戊烯基,栊牛儿基等取代基,一般发生苄基裂解。此外,这些取代基往往与邻位羟基环合形成六元氧环,此类化合物的ESI-MS/MS~n质谱裂解因六元氧环部分的差异而有所不同。而且,不同结构类型的2-苯基苯并呋喃类化合物裂解后产生特征离子,可用于此类化合物的快速检测以及在线鉴定。
长穗桑茎皮乙醇提取物乙酸乙酯部分中分离到的29个化合物(化合物1-3,8,10,12-14,16-17,21-23,25-26,33-36,39-41,43,45,47,49-51,56),浓度为10~(-5)M时,对Fe~(2+)-半胱氨酸诱导的肝微粒体脂质过氧化有抑制活性(抑制率>50%)。在抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放的模型上,11个化合物(化合物10-11,16,32,34,49-51,54,60,62)具有抗炎活性(抑制率大于50%,P<0.05)。
采用MTT法测定了长穗桑茎皮中分离得到的56个化合物对五种人肿瘤细胞(A549:人肺腺癌细胞;Bel-7402:人肝癌细胞;BGC-823:人胃癌细胞;HCT-8:人结肠癌细胞;A2780:人卵巢癌细胞)的抑制作用。结果显示26个化合物(化合物8,10-11,13-14,16,21-26,29,32-36,39,47,50-52,56,61,62),对人癌细胞有抑制作用;水提取物中得到的单体化合物(化合物64-73)均无抗肿瘤活性(超过10μg/mL,认为无活性)。
对长穗桑茎皮水提取物中得到的10个化合物进行α-葡萄糖苷酶抑制活性(蔗糖底物)筛选,测试结果显示7个多羟基生物碱(化合物64-70)以及1个酰胺类化合物(化合物72)有较强的抑制α-葡萄糖苷酶的活性,40μg/mL时抑制率均大于80%。其中化合物64的IC_(50)为0.07μM;化合物68的IC_(50)为0.39μM,与阳性对照阿卡波糖(Acarbose)(IC_(50)=0.52μM)相当;化合物69,70,72的IC_(50)值在1-5μM。
Morus wittiorum is the species belonging to the genus Morus of Moraceae.As the relative of the cultivated mulberry,it mostly distributes in the southern area of China.Its roots,twigs,leaves and fruits as well are used as the folk medicine.The bioactive screening on the 95%ethanol extract and water extract of the stem bark of M.wittiorum resulted in:the ethyl acetate fraction from the 95%ethanol extract displayed significant anti-oxidative activity;the acetone fraction and methanol fraction of the 95%ethanol extract and the water extract as well showed remarkable inhibitory activity againstα-glucosidase.
The 95%ethanol extract and water extract of the stem bark of M.wittiorum were investigated respectively on their chemical constituents systematically by various kinds of chromatographic methods.The isolates were elucidated on the basis of spectroscopic analysis and chemical methods as well.Some of them in sufficient amount were assayed for their bioactivities.The stem bark of M.wittiorum were collected from Jinxiu county of Guangxi province and identified by professor Shou-Yang Liu,Guangxi College of Traditional Chinese Medicine.
Among the seventy-four compounds isolated from the stem bark of M.wittiorum, thirty-one compounds(1-31) are new compounds,and the rest were isolated from this plant for the first time.Sixty-three compounds were isolated and identified from the 95% ethanol extract of the stem bark of M.wittiorum,including twenty-four Diels-Alder type adducts,thirty 2-arylbenzofuran derivatives,six flavonoids,three stilbenes.These compounds are listed as follows:wittiorumin A(1),wittiorumin B(2),wittiorumin C(3), wittiorumin D(4),wittiorumin E(5),wittiorumin F(6),wittiorumin G(7),wittifuran A (8),wittifuran B(9),wittifuran C(10),wittifuran D(11),wittifuran E(12),wittifuran F (13),wittifuran G(14),wittifuran H(15),wittifuran I(16),wittifuran J(17),wittifuran K (18),wittifuran L(19),wittifuran M(20),wittifuran N(21),wittifuran O(22),wittifuran P(23),wittifuran Q(24),wittifuran R(25),wittifuran S(26),wittifuran T(27),wittifuran U(28),wittifuran V(29),wittifuran W(30),wittifuran X(31),chalcomoracin(32), mongolicin F(33),mulberrofuran J(34),mulberrofuran K(35X mulberrofuran G(36), guangsangon L(37),kuwanon J(38),kuwanon X(39),guangsangon G(40), guangsangon B(41),guangsangon D(42),kuwanon P(43),albafuran C(44),sorocein A (45),mulberrofuran E(46),mulberrofuran F(47),mulberrofuran O(48),moracin M(49), moracin C(50),2-(3,5-dihydroxyphenyl)-5,6-dihydroxybenzofuran(51),moracin P(52), mulberroside C(53),austrafuran C(54),quercetin(55),5,7,3',4'-tetrahydroxy-3-metho-xyflavone (56),norartocarpanone(57),dihydrokaempferol(58),euchrenone a_7(59), morachalcone A(60),resveratrol(61),oxyresveratrol(62),4'-prenyloxyresveratrol(63).
Eleven compounds were obtained and identified from the water extract of the stem bark of M.wittiorum,including seven polyhydroxyalkalines,two acylamides,one amino acid and betaine.The corresponding compounds are displayed as 1-deoxynojirimycin (64),fagomine(65),3-epi-fagomine(66),1,4-dideoxy-1,4-imino-D-arabinitol(67), 2-O-α-D-galactopyranosyl-1 -deoxynojirimycin(68),4-O-β-D-glucopyranosyl-fagomine (69),1,4-dideoxy-1,4-imino-(2-O-β-D-glucopyranosyl)-D-arabinitol(70),(2S)-citrullina-mide (71),grateloupinamide(72),asparagic acid(73),betaine(74).
In addition,the investigations under the guiding of bioassay on the acetone fraction and methanol fraction of 95%ethanol extract respectively indicated that polyhydroxyalkalines were bioactive substances possessing inhibitory activity againstα-glucosidase.
The positive ESI-MS/MS~n spectra of fifteen 2-arylbenzofuran derivatives (compounds 8-11,13-14,17-18,21-27) were studied.Based on the data analysis,some fragmentation patterns were found.2-arylbenzofuran derivatives with substituents such as isoprenyls,geranyls and so on,usually performed the benzyl fragmentation.Moreover, the substituents often formed the pyran or dihydropyran ring with vicinal hydoxy,which resulted in different fragmentation.In addition,different fragmentation pathway produced various diagnostic ions,which were found for the first time in this thesis,could be used to detect or characterize 2-arylbenzofuran derivatives rapidly.
Within the compounds isolated from the stem bark of M.wittiorum,twenty-nine compounds(compounds 1-3,8,10,12-14,16-17,21-23,25-26,33-36,39-41,43,45,47, 49-51,56) inhibited the production of the lipid peroxide induced by Fe~(2+)-Cys system in the liver microsomal obviously,with inhibitory rates more than 50%at a concentration of 10~(-5) M.On the pharmacological model of release ofβ-glucuronidase from rat PMNs induced by PAF,eleven compounds(compounds 10-11,16,32,34,49-51,54,60,62) displayed antiinflammatory activity with the inhibitory rates more than 50%at a concentration of 10~(-5) M.
Twenty-six compounds(compounds 8,10-11,13-14,16,21-26,29,32-36,39,47, 50-52,56,61-62) obtained from the stem bark of M.wittiorum displayed moderate inhibitory activity against five human tumor cells(A549,Bel-7402,BGC-823,HCT-8 and A2780) by MTT method.However,compounds isolated from water extract (compounds 64-73) did not show inhibitory activity against any of the five tumor cells (IC_(50)>10μg/ml).
The inhibition againstα-glucosidase was performed for ten compounds isolated from water extract of the stem bark of M.wittiorum.The resulst showed that seven polyhydroxyalkalines(compounds 64-70) and one acylamide(compound 72) possessed significant inhibition agaistα-glucosidase,with inhibitory rates over 80%at a concentration of 40μg/mL.Especially for compound 64,IC_(50)= 0.07μM;the IC_(50) values of compound 68 was 0.39μM,which was comparative to the positive control acarbose (IC_(50) = 0.52μM).And the IC_(50) values of compounds 69,70,72 were within 1-5μM.
引文
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