金银花和鸡桑的化学成分与生物活性研究
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摘要
本文运用色谱和波谱技术相结合的方法,对忍冬科(Caprifoliaceae)忍冬属(Lonicera Linn)植物忍冬(Lonicera japonica Thunb)的花蕾金银花和桑科(Moraceae)桑属(Morus)植物鸡桑(Morus aus tralis)的化学成分进行了研究,并对其粗提物及单体成分进行了相关生物活性筛选。
金银花采自山东平邑,由中国医学科学院马林副研究员鉴定。鸡桑采自江西省,由江西九江森林植物研究所谭策铭教授鉴定。
从金银花的水提取物中分离并鉴定了40个化合物,分别是：Lonijapospiroside A (1*), L-phenylalaninosecologanin B (2*), L-phenylalaninosecologanin C (3*), Dehydroprolinoylloganin A (4*), loganin(5), secologanin (6), Secoxyloganin (7), Dimethyl-secoxyloganin (8), vogeloside (9),7-epi-vogeloside (10), Sweroside (11),7-ethyl-epi-vogeloside (12),(E)-aldosecologanin (13), Loniceracycloside (14), urceolide (15), abscisic acid (16),(1S,6R)-8-(-hydroxyabscisic acid)-β-D-glu copynaloside)(17), Limonin (18), Loniceroside A (19) Scopoletin (20), Xanthotoxin (21), isopimpinellin(22), oroseol(23), emodin(24),1-O-β-D-glucopyranosyl-emodin (25),3-O-ca ffeoylquinic acid (26),4,5-di-O-caffeoyl isoquinic acid (27),3,4-di-O-caffeoyl quinic acid(28),3,4-di-O-caffeoyl quinic acid methyl ester(29),4,5-di-O-caffeoyl quinic acid methyl ester (30),3,4-di-O-caffeoyl quinic acid ethyl ester (31),3,5-di-O-caffeoyl quinic acid ethyl ester (32), luteolin-7-O-β-D-glucop yranoside (33), chrysoeriol-7-O-β-D-glucopyranoside (34), Lonicerin (35),5,4'-d ihydroxy-3',5'-dimethoxy-7-β-D-glucosyloxy-flavone (36), Quercetin(37),(E-2-Hex enyl-a-L-arabin-opyranosyl-(1→>6)-β-D-glucopyranoside (38), Benzylalcohol-O-a-L-ar abinopyranosyl-(1→O-β-D-glucopyranoside (39), Eugenyl-β-D-xylopyranosyl-(1→6)-β-D-glucopyr anoside (40)。
其中1-4为新化合物,均为含氮环烯醚萜类化合物。已知化合物包括9个环烯醚萜类化合物(5-13),两个单萜环苷类(14-15),两个倍半萜类(16-17),两个三萜类(18-19),四个香豆素类(20-23),两个蒽醌类(24-25),7个咖啡酰喹宁酸类(26-32),五个黄酮类(33-37),3个其他类(38-40)。其中12个化合物(15,16,17,18,21,22,23,24,25,38,39,40)为忍冬属中首次分离得到。
从鸡桑中分离得到14个黄酮类化合物,分别是Benzokuwanon E (MA-1), Hydroxymorusin(MA-2), Dicyclokuwanon EA(MA-3), Dicyclokuwanon EB(MA-4), Kuwanon E(MA-5), Kuwanon U(MA-6), Kuwanon S(MA-7), Morusignin L(MA-8), Oxydihydromorusin(MA-9), Morusin(MA-10), Kuwanon C (MA-11), cyclomorusin (MA-12), mulberranol (MA-13), Hydroxymorusin (MA-14).其中MA-1～MA-4为四个新化合物,MA-14为新天然产物。
金银花药理活性筛选：1抗炎活性：金银花提取物大孔树脂D10115%,30%7,醇洗脱部分对巴豆油引起的小鼠耳炎有一定的作用；单体化合物活性筛选表明,10-5M时,化合物14、30对小鼠腹腔巨噬细胞分泌NO抑制率为44.6%、25.4%、,且无细胞毒活性,化合物2抑制率为25.7%,但有细胞毒作用。10-5M时,化合物15对小鼠腹腔巨噬细胞分泌TNF-α抑制率45.9%,化合物14、27、32抑制率约为20%。采用MCF7GFP-Bax细胞凋亡影响模型,所测化合物均未显示明显细胞凋亡诱导作用。
2.抗病毒活性：采用水泡性口膜炎病毒的糖蛋白外壳(VSV-G)包裹HIV核心,以荧光素酶为报告基因的VSVG/HIV-luc伪病毒系统。10-5M时,所测化合物均未表现出明显抗病毒活性。
3.抗肿瘤活性：金银花的粗提物和单体化合物对五种人癌细胞(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)均未表现出抗肿瘤活性。
鸡桑的药理活性：在10-5M时,化合物MA-2对Fe2+-半胱氨酸诱导的肝微粒体脂质过氧化物的抑制率约11%,显示微弱的抗氧化活性。
This dissertation focused on an investigation of main constituents of Lonicera japo nica Thunb belonging to the genus Lonicera Linn of Caprifoliaceae and Morus australia belonging to the gesus of Morus of Moraceae. Totally54compounds were isolated and their structure were elucidated by spectroscopic and chemical methods. The bioassays of their extract and pure compounds were also carried out on various pharm cological mode-ls.
The buds of Lonicera japonica was collected in Shandong province and identified by Professor Lin Ma, the Institute of Materia Medica, Chinese Academy of Medical Sci-ences&Peking Union Medical College. The barks of Morus australis was collected in Jiangxi province and identified by Professor Ce-ming Tan, the Jiujiang Botany Institute of Forest, Jiangxi province.
Forty compounds were isolated from Lonicera japonica Thunb, they were identifi ed as follows:Lonijapospiroside A(l*), L-phenylalaninosecologanin B (2*), L-phenyla laninosecologanin C(3*), Dehydroprolinoylloganin A (4*), loganin (5), secologanin (6), Secoxyloganin(7), Dimethyl-secoxyloganin(8), vogeloside(9),7-epi-vogeloside(10), Sweroside(11),7-ethyl-epi-vogeloside(12),(E)-aldosecologanin (13), Loniceracyclo side(14), urceolide(15), abscisic acid(16),(1S,6R)-8-(-hydroxya bscisic acid)-β-D-glucopynaloside)(17), Limonin(18), Loniceroside A (19), Scopole tin(20), Xanth-otoxin(21), isopimpinellin(22), oroseol(23), emodin(24),1-O-β-D-glucopyranosyl-emodin(25),3-O-caffeoylquinic acid(26),4,5-di-O-caffeoyl isoquinic acid(27),3,4-di-O-caff-eoyl quinic acid(28),3,4-di-O-caffeoyl quinic acid methyl ester(29),4,5-di-O-c-affeoyl quinic acid methyl ester(30),3,4-di-O-caffeoyl quinic acid ethyl ester(31),3,5-di-O-caffeoyl quinic acid ethyl ester (32), luteolin-7-O-β-D-gluco pyranoside(33), chrysoeriol-7-O-β-D-glucopyranoside (34), Lonicerin (35),5,4'-dihydr oxy—3',5'-dimethoxy-7-p-D-glucosyloxy-flavone (36), quercetin(37),(E)-2-Hexen yl-α-L-arabino pyranosyl-(1→6)-p-D-glucopyranoside (38), Benzylalcohol-O-a-L-arabi nopyranosyl-(1→6)-O-β-D-glucopyranoside (39), Eugenyl-β-D-xylopyranosyl-(1→6)-β-D-glucopyr anoside (40). Among these compounds, there were four new compounds belong to secoiri-doid with nitrogen, and12known compounds from the genus Lonicera for the first time. The structure types of the compounds included iridoid, monoterpenoid, sesquiterpenoid, triterpenoid, coumarin, anthraquinone, caferoylquinic acid, flavonoid, most of which were in glycoside.
Fourteen compounds isolated from Morus Australia, were listed as follows:Benzo-kuwanon E (MA-1), Hydroxymorusin(MA-2), Dicyclokuwanon EA(MA-3), Dicyclo-kuwanon EB(MA-4), Kuwanon E(MA-5), Kuwanon U(MA-6), Kuwanon S(MA-7), Morusignin L(MA-8), Oxydihydromorusin(MA-9), Morusin(MA-10), Kuwanon C (MA-11), cyclomorusin(MA-12), mulberranol(MA-13), Hydroxymorusin(MA-14). MA-1-MA-4were four new flavonoids.
The fraction D15, D30(eluting from macropore resin D101with ethanol15%,30%respectively) showed anti-flammatory activity on croton oil ear in mice. Within the compouds from Lonicera japonica Thunb, compounds2,14,30showed inhibitory activities against the release of NO in mice by Gibbs reduction method with inhibition rate of25.7%,44.6%,25.4%at10-5M, respectively. The later two showed no cytoxity but the former showed significant cytoxity on the same pharmacological mod-el. Compound15exhibited inhibitive activities against TNF-a in mouse macrophage wi-th inhibition rates of45.9%at10-5M, while compound27,32with inhibition rates about20%in the same condition. All of the compounds tested had no apoptosis activities on MCF7GFP-Bax model.
Compounds tested showed no antivirus activities on VSVG-HIV model at10-5M.
All the extracts and compounds from Lonicera japonica Thunb were inactive against human cancer cell lines(A549, Bel-7402, BGC-823, HCT-8and A2780) at10-5M on MTT model.
Among compounds isolated from Morus Australia, only MA-2inhibited the producti-on of the lipid peroxide induced by Fe2+-Cys system in the liver microsomal, with inhibi-tory rates10%at10-5M.
金银花采自山东平邑,由中国医学科学院马林副研究员鉴定。鸡桑采自江西省,由江西九江森林植物研究所谭策铭教授鉴定。
从金银花的水提取物中分离并鉴定了40个化合物,分别是：Lonijapospiroside A (1*), L-phenylalaninosecologanin B (2*), L-phenylalaninosecologanin C (3*), Dehydroprolinoylloganin A (4*), loganin(5), secologanin (6), Secoxyloganin (7), Dimethyl-secoxyloganin (8), vogeloside (9),7-epi-vogeloside (10), Sweroside (11),7-ethyl-epi-vogeloside (12),(E)-aldosecologanin (13), Loniceracycloside (14), urceolide (15), abscisic acid (16),(1S,6R)-8-(-hydroxyabscisic acid)-β-D-glu copynaloside)(17), Limonin (18), Loniceroside A (19) Scopoletin (20), Xanthotoxin (21), isopimpinellin(22), oroseol(23), emodin(24),1-O-β-D-glucopyranosyl-emodin (25),3-O-ca ffeoylquinic acid (26),4,5-di-O-caffeoyl isoquinic acid (27),3,4-di-O-caffeoyl quinic acid(28),3,4-di-O-caffeoyl quinic acid methyl ester(29),4,5-di-O-caffeoyl quinic acid methyl ester (30),3,4-di-O-caffeoyl quinic acid ethyl ester (31),3,5-di-O-caffeoyl quinic acid ethyl ester (32), luteolin-7-O-β-D-glucop yranoside (33), chrysoeriol-7-O-β-D-glucopyranoside (34), Lonicerin (35),5,4'-d ihydroxy-3',5'-dimethoxy-7-β-D-glucosyloxy-flavone (36), Quercetin(37),(E-2-Hex enyl-a-L-arabin-opyranosyl-(1→>6)-β-D-glucopyranoside (38), Benzylalcohol-O-a-L-ar abinopyranosyl-(1→O-β-D-glucopyranoside (39), Eugenyl-β-D-xylopyranosyl-(1→6)-β-D-glucopyr anoside (40)。
其中1-4为新化合物,均为含氮环烯醚萜类化合物。已知化合物包括9个环烯醚萜类化合物(5-13),两个单萜环苷类(14-15),两个倍半萜类(16-17),两个三萜类(18-19),四个香豆素类(20-23),两个蒽醌类(24-25),7个咖啡酰喹宁酸类(26-32),五个黄酮类(33-37),3个其他类(38-40)。其中12个化合物(15,16,17,18,21,22,23,24,25,38,39,40)为忍冬属中首次分离得到。
从鸡桑中分离得到14个黄酮类化合物,分别是Benzokuwanon E (MA-1), Hydroxymorusin(MA-2), Dicyclokuwanon EA(MA-3), Dicyclokuwanon EB(MA-4), Kuwanon E(MA-5), Kuwanon U(MA-6), Kuwanon S(MA-7), Morusignin L(MA-8), Oxydihydromorusin(MA-9), Morusin(MA-10), Kuwanon C (MA-11), cyclomorusin (MA-12), mulberranol (MA-13), Hydroxymorusin (MA-14).其中MA-1～MA-4为四个新化合物,MA-14为新天然产物。
金银花药理活性筛选：1抗炎活性：金银花提取物大孔树脂D10115%,30%7,醇洗脱部分对巴豆油引起的小鼠耳炎有一定的作用；单体化合物活性筛选表明,10-5M时,化合物14、30对小鼠腹腔巨噬细胞分泌NO抑制率为44.6%、25.4%、,且无细胞毒活性,化合物2抑制率为25.7%,但有细胞毒作用。10-5M时,化合物15对小鼠腹腔巨噬细胞分泌TNF-α抑制率45.9%,化合物14、27、32抑制率约为20%。采用MCF7GFP-Bax细胞凋亡影响模型,所测化合物均未显示明显细胞凋亡诱导作用。
2.抗病毒活性：采用水泡性口膜炎病毒的糖蛋白外壳(VSV-G)包裹HIV核心,以荧光素酶为报告基因的VSVG/HIV-luc伪病毒系统。10-5M时,所测化合物均未表现出明显抗病毒活性。
3.抗肿瘤活性：金银花的粗提物和单体化合物对五种人癌细胞(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)均未表现出抗肿瘤活性。
鸡桑的药理活性：在10-5M时,化合物MA-2对Fe2+-半胱氨酸诱导的肝微粒体脂质过氧化物的抑制率约11%,显示微弱的抗氧化活性。
This dissertation focused on an investigation of main constituents of Lonicera japo nica Thunb belonging to the genus Lonicera Linn of Caprifoliaceae and Morus australia belonging to the gesus of Morus of Moraceae. Totally54compounds were isolated and their structure were elucidated by spectroscopic and chemical methods. The bioassays of their extract and pure compounds were also carried out on various pharm cological mode-ls.
The buds of Lonicera japonica was collected in Shandong province and identified by Professor Lin Ma, the Institute of Materia Medica, Chinese Academy of Medical Sci-ences&Peking Union Medical College. The barks of Morus australis was collected in Jiangxi province and identified by Professor Ce-ming Tan, the Jiujiang Botany Institute of Forest, Jiangxi province.
Forty compounds were isolated from Lonicera japonica Thunb, they were identifi ed as follows:Lonijapospiroside A(l*), L-phenylalaninosecologanin B (2*), L-phenyla laninosecologanin C(3*), Dehydroprolinoylloganin A (4*), loganin (5), secologanin (6), Secoxyloganin(7), Dimethyl-secoxyloganin(8), vogeloside(9),7-epi-vogeloside(10), Sweroside(11),7-ethyl-epi-vogeloside(12),(E)-aldosecologanin (13), Loniceracyclo side(14), urceolide(15), abscisic acid(16),(1S,6R)-8-(-hydroxya bscisic acid)-β-D-glucopynaloside)(17), Limonin(18), Loniceroside A (19), Scopole tin(20), Xanth-otoxin(21), isopimpinellin(22), oroseol(23), emodin(24),1-O-β-D-glucopyranosyl-emodin(25),3-O-caffeoylquinic acid(26),4,5-di-O-caffeoyl isoquinic acid(27),3,4-di-O-caff-eoyl quinic acid(28),3,4-di-O-caffeoyl quinic acid methyl ester(29),4,5-di-O-c-affeoyl quinic acid methyl ester(30),3,4-di-O-caffeoyl quinic acid ethyl ester(31),3,5-di-O-caffeoyl quinic acid ethyl ester (32), luteolin-7-O-β-D-gluco pyranoside(33), chrysoeriol-7-O-β-D-glucopyranoside (34), Lonicerin (35),5,4'-dihydr oxy—3',5'-dimethoxy-7-p-D-glucosyloxy-flavone (36), quercetin(37),(E)-2-Hexen yl-α-L-arabino pyranosyl-(1→6)-p-D-glucopyranoside (38), Benzylalcohol-O-a-L-arabi nopyranosyl-(1→6)-O-β-D-glucopyranoside (39), Eugenyl-β-D-xylopyranosyl-(1→6)-β-D-glucopyr anoside (40). Among these compounds, there were four new compounds belong to secoiri-doid with nitrogen, and12known compounds from the genus Lonicera for the first time. The structure types of the compounds included iridoid, monoterpenoid, sesquiterpenoid, triterpenoid, coumarin, anthraquinone, caferoylquinic acid, flavonoid, most of which were in glycoside.
Fourteen compounds isolated from Morus Australia, were listed as follows:Benzo-kuwanon E (MA-1), Hydroxymorusin(MA-2), Dicyclokuwanon EA(MA-3), Dicyclo-kuwanon EB(MA-4), Kuwanon E(MA-5), Kuwanon U(MA-6), Kuwanon S(MA-7), Morusignin L(MA-8), Oxydihydromorusin(MA-9), Morusin(MA-10), Kuwanon C (MA-11), cyclomorusin(MA-12), mulberranol(MA-13), Hydroxymorusin(MA-14). MA-1-MA-4were four new flavonoids.
The fraction D15, D30(eluting from macropore resin D101with ethanol15%,30%respectively) showed anti-flammatory activity on croton oil ear in mice. Within the compouds from Lonicera japonica Thunb, compounds2,14,30showed inhibitory activities against the release of NO in mice by Gibbs reduction method with inhibition rate of25.7%,44.6%,25.4%at10-5M, respectively. The later two showed no cytoxity but the former showed significant cytoxity on the same pharmacological mod-el. Compound15exhibited inhibitive activities against TNF-a in mouse macrophage wi-th inhibition rates of45.9%at10-5M, while compound27,32with inhibition rates about20%in the same condition. All of the compounds tested had no apoptosis activities on MCF7GFP-Bax model.
Compounds tested showed no antivirus activities on VSVG-HIV model at10-5M.
All the extracts and compounds from Lonicera japonica Thunb were inactive against human cancer cell lines(A549, Bel-7402, BGC-823, HCT-8and A2780) at10-5M on MTT model.
Among compounds isolated from Morus Australia, only MA-2inhibited the producti-on of the lipid peroxide induced by Fe2+-Cys system in the liver microsomal, with inhibi-tory rates10%at10-5M.
引文
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