黄花紫玉盘、陵水暗罗的化学成分及生物活性研究
摘要
为了从植物中寻找新的生物活性物质,充分开发利用我国丰富的植物资源,本论文对产于我国云南的紫玉盘属植物黄花紫玉盘Uvaria kurzii(King)P.T.Li和产于我国海南的暗罗属植物陵水暗罗(Polyalthia nemoralis A.DC)进行了化学成分和生物活性的研究。
从黄花紫玉盘枝、叶的95%EtOH提取物中分离、鉴定了34个化合物,包括5个贝壳杉烷型二萜类化合物,5个阿朴菲生物碱类化合物,4个蒽醌类化合物,3个黄酮苷类化合物,9个甾体类化合物,8个其他类化合物。这些化合物经鉴定为:bis(4-octanoylphenyl)-methane(1),ent-kaur-16-en-19-oic acid(2),grandifloric acid(3),ent-kaur-15-en-17-ol-19-oic acid(4),ent-16α,17-dihydroxykauran-19-oic acid(5),ent-16β,17-dihydroxykauran-19-oic acid(6),bidebiline A(7),annobraine(8),oxoputerine(9),atherospermidine(10),liriodenine(11),allantoin(12),physcion(13),questin(14),rubiadin 3-methyl ether(15),emodin(16),kaempferol-3- O-β-D-(6″-O-p-coumaryoyl)galactopyrannoside(17),kaempferol-3-O-rutinoide(18),rutin(19),vanillic acid(20),protocatechuicacid(21),N-(p-trans-coumaroyl)tyramine(22),β-sitosterol hexadecanoate(23),stigmasterol hexadecanoate(24),β-acetylsitosterol(25),β-acetylstigmasterol(26),β-sitosterol(27),stigmasterol(28),5α-stigmast-3,6-dione(29),5α-stigmast-22-ene-3,6-dione(30),daucosterol(31),L-quebrachitol(32),tetratriacontanol(33),dotriacontanoic acid(34)。其中,化合物1为新化合物;12-16,22-26,29,30,32-34为本科中首次分到;2-10,17-19为本属中首次分到:11,20,21,27,28,31为本种植物中首次分到。
从陵水暗罗枝、叶的95%EtOH提取物中分离、鉴定了38个化合物,包括8个阿朴菲类生物碱,7个2-巯基吡啶类化合物,3个苄基异喹啉季铵生物碱,4个酚酸,4个多元醇,2个甾醇类化合物,8个其他类型化合物。这些化合物经鉴定为:polynemoraline A(35),polynemoraline B(36),polynemoraline C(37),polynemoraline D(38),zincpolyanemine(39),nickel bis(pyridine-N-oxide-2-thiolate)(40),cupric bis(pyridine-N-oxide-2thiolate)(41),2-methanesulfonyl-pyridine(42),2-pyridinethiolate N-oxide(43),2-thiohydroxy-pyridin-N-oxide-2-S-β-D-gluco-pyranoside(44),2,2'-dithiodipyridine(45),bidebiline A(46),annobraine(47),lanuginosine(48),liriodenine(49),oxostephanosine(50),(+)-magnoflorine(51),(+)-xylopinidine(52),(+)-oblongine(53),(+)-tembetarine(54),stepharanine(55),pyridine-N-oxide(56),syringic acid(57),3-methoxy-4-hydroxycinnamicacid(58),vanillic acid(59),4-hydroxybenzoic acid(60),mauritianin(61),3-amino-3-deoxy-D-glucose(62),eythritol(63),D-mannitol(64),glycerol(65),ethyl-β-D-glucopyranoside(66),myo-inositol(67),β-sitosterol(68),daucosterol(69),(2S,4R)-4-hydroxy-2-piperidinecarboxylic acid(70),stearic acid(71)。其中,化合物35-38为新化合物:40,42,43,45,56为新天然产物:50,53-55,61,62,70为本科中首次分到;47,51,52,57-59,60,63,64,65为本属中首次分到:46,48,49,71为本种植物中首次分到。
药理筛选表明,陵水暗罗中的4个2-巯基吡啶类化合物细胞毒作用很强,IC_(50)一般在0.05μg/ml。另外黄花紫玉盘和陵水暗罗中的氧化阿朴菲生物碱也具有细胞毒作用,IC_(50)一般在1μg/ml。
新化合物bis(4-octanoylphenyl)methane(1)经初步药理筛选,结果显示能够明显增加冠脉流量及心肌收缩力。为进一步探讨构效关系,和提供药理筛选,寻找新的活性先导物,合成了9个类似化合物,其中2个为新化合物。
In order to discover bio-active compounds from rich Chinese plant sources and make full use of them,the chemical constituents of Uvaria kurzii(King) P.T.and Polyalthia nemoralis A.DC.were systematically separated with various chromatographic techniques and the structures were elucidated by means of spectra and chemical methods.Furthermore,the isolates were screened for biological activities.
34 compounds were isolated,purified and identified from the EtOH extract of Uvaria kurzii(King) P.T.branches and leaves,including 5 ent-kaurane diterpenoids,5 aporphine alkaloids,4 anthraquinones,3 flavonoids,9 steroids,and 7 other type compounds.These compounds are identified as follows:bis(4-octanoylphenyl)methane (1),ent-kaur-16-en-19-oic acid(2),grandifloric acid(3), ent-kaur-15-en-17-ol-19-oic acid(4),ent-16a,17-dihydroxykauran-19-oic acid(5), ent-16β,17-dihydroxykauran-19-oic acid(6),bidebiline A(7),annobraine(8), oxoputerine(9),atherospermidine(10),liriodenine(11),allantoin(12),physcion (13),questin(14),rubiadin 3-methyl ether(15),emodin(16),kaempferol-3-O-β-D-(6"-O-p-coumaryoyl)galactopyrannoside(17),kaempferol-3-O-rutinoide (18),rutin(19),vanillic acid(20),protocatechuic acid(21),N-(p-trans-coumaroyl) tyramine(22),β-sitosterol hexadecanoate(23),stigmasterol hexadecanoate(24),β-acetylsitosterol(25),13-acetylstigmasterol(26),13-sitosterol(27),stigmasterol (28),5a-stigmast-3,6-dione(29),5a-stigmast-22-ene-3,6-dione(30),daucosterol (31),L-quebrachitol(32),tetratriacontanol(33),dotdacontanoic.Among them, 1 is a new compound,and 12-16,22-26,29,30,32-34 were isolated from Annonaceae for the first time,2-10,17-19 were firstly found from genus Uvaria,as well as 11,20,21,27,28,31 firstly found from Uvaria kurzii(King) P.T..
38 compounds were isolated from the EtOH extract of Polyalthia nemoralis A.DC. branches and leaves,including 8 aporphine alkaloids,7 2-thiopyridines,3 quaternary benzyltetrahydronisoquinolines,4 simple phenols,4 polyols,2 steroids,and 10 other type compounds.These compounds were identified as follows:polynemoraline A (35),polynemoraline B(36),polynemoraline C(37),polynemoraline D(38), zincpolyanemine(39),nickel bis(pyridine-N-oxide-2-thiolate)(40),cupric bis-(pyridine-N-oxide-2thiolate) (41),2-methanesulfonyl-pyridine(42), 2-pyridinethiolate N-oxide(43),2-thiohydroxy-pyridin-N-oxide-2-S-β-D-glucopyranoside (44),2,2'-dithiodipyridine(45),bidebiline A(46),annobraine (47),lanuginosine(48),liriodenine(49),oxostephanosine(50),(+)-magnoflorine (51),(+)-xylopinidine(52),(+)-oblongine(53),(+)-tembetarine(54), stepharanine(55),pyridine-N-oxide(56),syringic acid(57),3-methoxy-4-hydroxycinnamic acid(58),vanillic acid(59),4-hydroxybenzoic acid(60), mauritianin(61),3-amino-3-deoxy-D-glucose(62),eythritol(63),D-mannitol (64),ethyl-β-D-glucopyranoside(65),myo-inositol(66),glycerol(67),β-sitosterol(68),daucosterol(69),(2S,4R)-4-hydroxy-2-piperidinecarboxylic acid(70),stearic acid(71)。Among them,35-38 are identified to be novel compounds,40,42,43,45,56 were new natural products,50,53-55,61,62, 70were isolated for the first time from Annonaceae,47,51,52,57-59,60,63, 64,65were isolated for the first time from genus Polyalthia,and 46,48,49,71 are found from Polyalthia neraoralis A.DC.。
Bio-activity test in vitro against human tumor cell lines with MTT method showed potent cytotoxic activity of 39-,40,41,43(IC_(50) 0.05μg/ml),which were isolated from Polyalthia nemoralis A.DC.In addition,the oxoaporphines isolated from these two plants showed moderate cytotoxic activity(IC_(50) 1μg/ml).
The new compound,bis(4-octanoylphenyl)methane(1),showed significantly to increase the coronary flow and the contractile force.Thus 9 analogues of 1 were designed and synthesized for the bioactivity test and the QSR study,among them,2 compounds were new.
从黄花紫玉盘枝、叶的95%EtOH提取物中分离、鉴定了34个化合物,包括5个贝壳杉烷型二萜类化合物,5个阿朴菲生物碱类化合物,4个蒽醌类化合物,3个黄酮苷类化合物,9个甾体类化合物,8个其他类化合物。这些化合物经鉴定为:bis(4-octanoylphenyl)-methane(1),ent-kaur-16-en-19-oic acid(2),grandifloric acid(3),ent-kaur-15-en-17-ol-19-oic acid(4),ent-16α,17-dihydroxykauran-19-oic acid(5),ent-16β,17-dihydroxykauran-19-oic acid(6),bidebiline A(7),annobraine(8),oxoputerine(9),atherospermidine(10),liriodenine(11),allantoin(12),physcion(13),questin(14),rubiadin 3-methyl ether(15),emodin(16),kaempferol-3- O-β-D-(6″-O-p-coumaryoyl)galactopyrannoside(17),kaempferol-3-O-rutinoide(18),rutin(19),vanillic acid(20),protocatechuicacid(21),N-(p-trans-coumaroyl)tyramine(22),β-sitosterol hexadecanoate(23),stigmasterol hexadecanoate(24),β-acetylsitosterol(25),β-acetylstigmasterol(26),β-sitosterol(27),stigmasterol(28),5α-stigmast-3,6-dione(29),5α-stigmast-22-ene-3,6-dione(30),daucosterol(31),L-quebrachitol(32),tetratriacontanol(33),dotriacontanoic acid(34)。其中,化合物1为新化合物;12-16,22-26,29,30,32-34为本科中首次分到;2-10,17-19为本属中首次分到:11,20,21,27,28,31为本种植物中首次分到。
从陵水暗罗枝、叶的95%EtOH提取物中分离、鉴定了38个化合物,包括8个阿朴菲类生物碱,7个2-巯基吡啶类化合物,3个苄基异喹啉季铵生物碱,4个酚酸,4个多元醇,2个甾醇类化合物,8个其他类型化合物。这些化合物经鉴定为:polynemoraline A(35),polynemoraline B(36),polynemoraline C(37),polynemoraline D(38),zincpolyanemine(39),nickel bis(pyridine-N-oxide-2-thiolate)(40),cupric bis(pyridine-N-oxide-2thiolate)(41),2-methanesulfonyl-pyridine(42),2-pyridinethiolate N-oxide(43),2-thiohydroxy-pyridin-N-oxide-2-S-β-D-gluco-pyranoside(44),2,2'-dithiodipyridine(45),bidebiline A(46),annobraine(47),lanuginosine(48),liriodenine(49),oxostephanosine(50),(+)-magnoflorine(51),(+)-xylopinidine(52),(+)-oblongine(53),(+)-tembetarine(54),stepharanine(55),pyridine-N-oxide(56),syringic acid(57),3-methoxy-4-hydroxycinnamicacid(58),vanillic acid(59),4-hydroxybenzoic acid(60),mauritianin(61),3-amino-3-deoxy-D-glucose(62),eythritol(63),D-mannitol(64),glycerol(65),ethyl-β-D-glucopyranoside(66),myo-inositol(67),β-sitosterol(68),daucosterol(69),(2S,4R)-4-hydroxy-2-piperidinecarboxylic acid(70),stearic acid(71)。其中,化合物35-38为新化合物:40,42,43,45,56为新天然产物:50,53-55,61,62,70为本科中首次分到;47,51,52,57-59,60,63,64,65为本属中首次分到:46,48,49,71为本种植物中首次分到。
药理筛选表明,陵水暗罗中的4个2-巯基吡啶类化合物细胞毒作用很强,IC_(50)一般在0.05μg/ml。另外黄花紫玉盘和陵水暗罗中的氧化阿朴菲生物碱也具有细胞毒作用,IC_(50)一般在1μg/ml。
新化合物bis(4-octanoylphenyl)methane(1)经初步药理筛选,结果显示能够明显增加冠脉流量及心肌收缩力。为进一步探讨构效关系,和提供药理筛选,寻找新的活性先导物,合成了9个类似化合物,其中2个为新化合物。
In order to discover bio-active compounds from rich Chinese plant sources and make full use of them,the chemical constituents of Uvaria kurzii(King) P.T.and Polyalthia nemoralis A.DC.were systematically separated with various chromatographic techniques and the structures were elucidated by means of spectra and chemical methods.Furthermore,the isolates were screened for biological activities.
34 compounds were isolated,purified and identified from the EtOH extract of Uvaria kurzii(King) P.T.branches and leaves,including 5 ent-kaurane diterpenoids,5 aporphine alkaloids,4 anthraquinones,3 flavonoids,9 steroids,and 7 other type compounds.These compounds are identified as follows:bis(4-octanoylphenyl)methane (1),ent-kaur-16-en-19-oic acid(2),grandifloric acid(3), ent-kaur-15-en-17-ol-19-oic acid(4),ent-16a,17-dihydroxykauran-19-oic acid(5), ent-16β,17-dihydroxykauran-19-oic acid(6),bidebiline A(7),annobraine(8), oxoputerine(9),atherospermidine(10),liriodenine(11),allantoin(12),physcion (13),questin(14),rubiadin 3-methyl ether(15),emodin(16),kaempferol-3-O-β-D-(6"-O-p-coumaryoyl)galactopyrannoside(17),kaempferol-3-O-rutinoide (18),rutin(19),vanillic acid(20),protocatechuic acid(21),N-(p-trans-coumaroyl) tyramine(22),β-sitosterol hexadecanoate(23),stigmasterol hexadecanoate(24),β-acetylsitosterol(25),13-acetylstigmasterol(26),13-sitosterol(27),stigmasterol (28),5a-stigmast-3,6-dione(29),5a-stigmast-22-ene-3,6-dione(30),daucosterol (31),L-quebrachitol(32),tetratriacontanol(33),dotdacontanoic.Among them, 1 is a new compound,and 12-16,22-26,29,30,32-34 were isolated from Annonaceae for the first time,2-10,17-19 were firstly found from genus Uvaria,as well as 11,20,21,27,28,31 firstly found from Uvaria kurzii(King) P.T..
38 compounds were isolated from the EtOH extract of Polyalthia nemoralis A.DC. branches and leaves,including 8 aporphine alkaloids,7 2-thiopyridines,3 quaternary benzyltetrahydronisoquinolines,4 simple phenols,4 polyols,2 steroids,and 10 other type compounds.These compounds were identified as follows:polynemoraline A (35),polynemoraline B(36),polynemoraline C(37),polynemoraline D(38), zincpolyanemine(39),nickel bis(pyridine-N-oxide-2-thiolate)(40),cupric bis-(pyridine-N-oxide-2thiolate) (41),2-methanesulfonyl-pyridine(42), 2-pyridinethiolate N-oxide(43),2-thiohydroxy-pyridin-N-oxide-2-S-β-D-glucopyranoside (44),2,2'-dithiodipyridine(45),bidebiline A(46),annobraine (47),lanuginosine(48),liriodenine(49),oxostephanosine(50),(+)-magnoflorine (51),(+)-xylopinidine(52),(+)-oblongine(53),(+)-tembetarine(54), stepharanine(55),pyridine-N-oxide(56),syringic acid(57),3-methoxy-4-hydroxycinnamic acid(58),vanillic acid(59),4-hydroxybenzoic acid(60), mauritianin(61),3-amino-3-deoxy-D-glucose(62),eythritol(63),D-mannitol (64),ethyl-β-D-glucopyranoside(65),myo-inositol(66),glycerol(67),β-sitosterol(68),daucosterol(69),(2S,4R)-4-hydroxy-2-piperidinecarboxylic acid(70),stearic acid(71)。Among them,35-38 are identified to be novel compounds,40,42,43,45,56 were new natural products,50,53-55,61,62, 70were isolated for the first time from Annonaceae,47,51,52,57-59,60,63, 64,65were isolated for the first time from genus Polyalthia,and 46,48,49,71 are found from Polyalthia neraoralis A.DC.。
Bio-activity test in vitro against human tumor cell lines with MTT method showed potent cytotoxic activity of 39-,40,41,43(IC_(50) 0.05μg/ml),which were isolated from Polyalthia nemoralis A.DC.In addition,the oxoaporphines isolated from these two plants showed moderate cytotoxic activity(IC_(50) 1μg/ml).
The new compound,bis(4-octanoylphenyl)methane(1),showed significantly to increase the coronary flow and the contractile force.Thus 9 analogues of 1 were designed and synthesized for the bioactivity test and the QSR study,among them,2 compounds were new.
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