赤雹与侧扁软柳珊瑚化学成分的研究
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摘要
赤雹Thladiantha dubia Bunge属葫芦科赤雹属植物,以果实及块根入药,其果实用于跌打损伤,嗳气吐酸,黄疸,肠炎,痢疾,肺结核咯血;其块根应用于治乳汁不下,乳房胀痛,在满族民间沿用已久,疗效显著。主要分布于华北、东北、内蒙古等地区。赤雹的化学成分和药理作用被报道的较少,据文献记载赤雹的根茎中含有三萜皂苷,三萜类化合物是葫芦科植物中一类主要的成分,葫芦科药用植物的许多功效都与三萜类化合物有关。本文将研究赤雹Thladiantha dubia Bunge.茎化学成分,采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、中压柱色谱和薄层制备色谱等方法对赤雹茎进行分离纯化,利用理化性质和波谱数据鉴定化合物结构。
侧扁软柳珊瑚Subergorgia suberosa(Pallas)属于八放珊瑚亚纲(Octocorallia)软珊瑚目(Alcyonacea)软柳珊瑚科(Subergorgiidae)软柳珊瑚属Subergorgia动物,在广东沿海及海南岛附近水域可常见。我们课题组为寻找具有较好抗肿瘤、抗污损活性成分,以侧扁软柳珊瑚为研究对象,采用中压制备色谱、硅胶柱色谱、Sephadex LH-20凝胶柱色谱、ODS和薄层制备色谱等方法对侧扁软柳珊瑚的提取物进行分离纯化,运用质谱法(MS)、核磁共振波谱法(NMR)等现代波谱学方法鉴定单一化合物结构。
从上述两种材料共分离得到38个化合物,鉴定了33个化合物,其中3个化合物为新化合物。从赤雹茎乙醇提取物中分离了13个化合物并鉴定了10个化合物,分别为山奈酚-7-O-α-L-鼠李糖苷(1)、山奈酚-3-O-(6″-O-α-L-鼠李糖苷)-β-D-葡萄糖苷(2)、咖啡酸乙酯(3)、3,4-二甲氧基苯乙酮(4)、豆甾醇(5)、胆甾醇(6)、α-菠甾醇(7)、(2R,3S,2′S,4E,8E)-Δ~(4(5)),Δ~(8(9))-鞘氨醇-2′-羟基-十六碳酰胺(8)、1-(17Z-二十四碳稀基)-甘油醚(9)、邻苯二甲酸二-(2-乙基)己酯(10)。化合物3、9、10首次从葫芦科中分离得到;化合物1、2首次从赤雹属分离得到;4、5、6、8首次从该植物中分离得到。
从侧扁软柳珊瑚分离25个化合物,鉴定了23个化合物:4-羟甲基-5β-孕甾-3,20-二酮(11),SC3-8(12),SC2-27(13),孕甾-4-烯-3,20-二酮(14),3β-羟基-5β-孕甾-20-酮(15),3β-羟基-5-烯-孕甾-20-酮(16),3β-羟基-5α-孕甾-20-酮(17),3α-羟基-5β-孕甾-20-酮(18),胆甾醇(19),麦角甾-6,22-二烯-5α,8α-环二氧-3-醇(20),柳珊瑚酸甲酯(21),柳珊瑚酸(22),2β-羟基柳珊瑚酸甲酯(23),suberosanone(24),suberosenol A(25),suberosenol B(26),suberosenone(27),鲨肝醇(28),N-正十六碳酰胺基-正十八碳-9-甲基-4(E),8(E)-二烯鞘胺醇(29),邻苯二甲酸二-(2-乙基)己酯(30),邻苯二甲酸正丁异丁酯(31),正十七醇(32), 5(E), 8(E), 11(E), 14(E)-二十碳四烯酸甲酯(33),其中化合物11、12、13三个为新化合物。
上述研究为赤雹和侧扁柳珊瑚进一步开发利用,提供了科学依据。为同属不同种其他物种化学成分研究提供了重要参考。
Thladiantha dubia Bunge is a species of genus Thladiantha of cucurbitaceae, It’s fruit and root were used as medicine, It’s fruit was used for traumatic injury, belching vomit acid, jaundice, enteritis, dysentery, hemoptysis of pulmonarytuberculosis; It’s root was used for curing lack of mother's milk and acute mastitis, It was well known in the Manchu people to cure disease and effective in treatment. Thladiantha dubia Bunge mainly distributes in north China, northeast China, Inner Mongolia ect. the chemical constituents and pharmacological activities of Thladiantha dubia Bunge were reported less. triterpenoid saponins were reported from literature, it is a kind of main compound in the cucurbitaceae. the medicinal effect is concerned with triterpene compounds in medicinal plants of cucurbitaceae. The paper will study the chemical constituents of the stem of Thladiantha dubia Bunge. , The compounds were isolated with silica gel, Sephadex LH-20 gel column, medium pressure liquid chromatography and preparative thin-layer chromatography (PTLC). Their structures were identified on the basis of spectroscopic evidence (MS, NMR ect) and physiochemical properties.
Subergorgia suberosa(Pallas) is a marine animal of the genus of Subergorgia (Subergorgiidae, Alcyonacea, Octocorallia), It is always found in the coastal areas of guangdong and hainan island. For looking for compounds of better antitumor and fouling, we investigated Subergorgia suberosa(Pallas). The compounds were isolated with medium pressure liquid chromatography, silica gel, Sephadex LH-20 gel column, ODS and preparative thin-layer chromatography(PTLC). Their structures were identified on the basis of spectroscopic evidence and physiochemical properties.
38 compounds were obtained from the two materials, among which 32 compounds were identified , including 3 new compounds. 13 compounds were isolated from stem of Thladiantha dubia Bunge.. Ten compounds were identified as: kaempferol-7-O-α-L-rhamnoside(1),
kaempferol-3-O-β-D-(6″-O-α-L-RhamnopyRa-nosyl)glucopyranoside (2), ethyl caffeate(3), 3′, 4′-dimethoxyaceophone(4), stigmasterol(5) , cholesterol(6),α-spinasterol(7), (2R, 3S, 2′S, 4E, 8E)-Δ4(5),Δ8(9)-sphingosine-2′-hydroxyhexa-decanoylamideo(8), 3-(17Z-tetracosenyloxy)-1, 2-propanediol(9), phthalic acid bis-(2-ethylhexyl) ester(10). Compounds 3, 9, 10 were obtained from Cucurbitaceae for the first time; Compounds 1, 2 were obtained from Thladiantha for the first time; Compounds 4, 5, 6, 8 were obtained from this plant for the first time.
25 compounds were obtained from the Subergorgia suberosa(Pallas), among which 23 compounds were identified as: 4-hydroxymethyl-5β-pregn-4-ene-3, 20-dione(11), SC3-8(12), SC2-27(13), pregn-4-ene-3, 20-dione (14), 3β, 5β-pregn-20-one-3-ol (15), 3β-Pregn-5-ene-20-one-3-ol (16), 3β, 5α-Pregn-20-one-3-ol (17), 3α-hydroxy-5β-pregnan-20-one (18), cholesterol (19), (22E,24S)-5α, 8α-epidioxy-24-methyl-cholesta-6, 22-dien-3β-ol (20), subergorgic acid methyl ester (21), subergorgic acid (22), 2β-hydroxy subergorgic acid methyl ester(23), suberosanone (24), suberosenol A(25), suberosenol B (26), suberosenone (27), Batyl alcohol (28), N-hexadecanoyl-octadecasphinga-9-methy-4(E) , 8(E)-dienin (29), phthalic acid bis-(2-ethylhexyl)ester (30), phthalic acid butyl isobutyl esterm (31), 1-heptadecanol(32), 5(E), 8(E), 11(E), 14(E)-Twenty carbon arachidonic acid methyl ester (33). Compound11, 12 and 13 are new compounds.
The above researches will provide scientific basis for Thladiantha dubia Bunge and Subergorgia suberosa(Pallas) in further development and utilization. They also provide important reference for the research of chemical composition of the same genera’s other species.
侧扁软柳珊瑚Subergorgia suberosa(Pallas)属于八放珊瑚亚纲(Octocorallia)软珊瑚目(Alcyonacea)软柳珊瑚科(Subergorgiidae)软柳珊瑚属Subergorgia动物,在广东沿海及海南岛附近水域可常见。我们课题组为寻找具有较好抗肿瘤、抗污损活性成分,以侧扁软柳珊瑚为研究对象,采用中压制备色谱、硅胶柱色谱、Sephadex LH-20凝胶柱色谱、ODS和薄层制备色谱等方法对侧扁软柳珊瑚的提取物进行分离纯化,运用质谱法(MS)、核磁共振波谱法(NMR)等现代波谱学方法鉴定单一化合物结构。
从上述两种材料共分离得到38个化合物,鉴定了33个化合物,其中3个化合物为新化合物。从赤雹茎乙醇提取物中分离了13个化合物并鉴定了10个化合物,分别为山奈酚-7-O-α-L-鼠李糖苷(1)、山奈酚-3-O-(6″-O-α-L-鼠李糖苷)-β-D-葡萄糖苷(2)、咖啡酸乙酯(3)、3,4-二甲氧基苯乙酮(4)、豆甾醇(5)、胆甾醇(6)、α-菠甾醇(7)、(2R,3S,2′S,4E,8E)-Δ~(4(5)),Δ~(8(9))-鞘氨醇-2′-羟基-十六碳酰胺(8)、1-(17Z-二十四碳稀基)-甘油醚(9)、邻苯二甲酸二-(2-乙基)己酯(10)。化合物3、9、10首次从葫芦科中分离得到;化合物1、2首次从赤雹属分离得到;4、5、6、8首次从该植物中分离得到。
从侧扁软柳珊瑚分离25个化合物,鉴定了23个化合物:4-羟甲基-5β-孕甾-3,20-二酮(11),SC3-8(12),SC2-27(13),孕甾-4-烯-3,20-二酮(14),3β-羟基-5β-孕甾-20-酮(15),3β-羟基-5-烯-孕甾-20-酮(16),3β-羟基-5α-孕甾-20-酮(17),3α-羟基-5β-孕甾-20-酮(18),胆甾醇(19),麦角甾-6,22-二烯-5α,8α-环二氧-3-醇(20),柳珊瑚酸甲酯(21),柳珊瑚酸(22),2β-羟基柳珊瑚酸甲酯(23),suberosanone(24),suberosenol A(25),suberosenol B(26),suberosenone(27),鲨肝醇(28),N-正十六碳酰胺基-正十八碳-9-甲基-4(E),8(E)-二烯鞘胺醇(29),邻苯二甲酸二-(2-乙基)己酯(30),邻苯二甲酸正丁异丁酯(31),正十七醇(32), 5(E), 8(E), 11(E), 14(E)-二十碳四烯酸甲酯(33),其中化合物11、12、13三个为新化合物。
上述研究为赤雹和侧扁柳珊瑚进一步开发利用,提供了科学依据。为同属不同种其他物种化学成分研究提供了重要参考。
Thladiantha dubia Bunge is a species of genus Thladiantha of cucurbitaceae, It’s fruit and root were used as medicine, It’s fruit was used for traumatic injury, belching vomit acid, jaundice, enteritis, dysentery, hemoptysis of pulmonarytuberculosis; It’s root was used for curing lack of mother's milk and acute mastitis, It was well known in the Manchu people to cure disease and effective in treatment. Thladiantha dubia Bunge mainly distributes in north China, northeast China, Inner Mongolia ect. the chemical constituents and pharmacological activities of Thladiantha dubia Bunge were reported less. triterpenoid saponins were reported from literature, it is a kind of main compound in the cucurbitaceae. the medicinal effect is concerned with triterpene compounds in medicinal plants of cucurbitaceae. The paper will study the chemical constituents of the stem of Thladiantha dubia Bunge. , The compounds were isolated with silica gel, Sephadex LH-20 gel column, medium pressure liquid chromatography and preparative thin-layer chromatography (PTLC). Their structures were identified on the basis of spectroscopic evidence (MS, NMR ect) and physiochemical properties.
Subergorgia suberosa(Pallas) is a marine animal of the genus of Subergorgia (Subergorgiidae, Alcyonacea, Octocorallia), It is always found in the coastal areas of guangdong and hainan island. For looking for compounds of better antitumor and fouling, we investigated Subergorgia suberosa(Pallas). The compounds were isolated with medium pressure liquid chromatography, silica gel, Sephadex LH-20 gel column, ODS and preparative thin-layer chromatography(PTLC). Their structures were identified on the basis of spectroscopic evidence and physiochemical properties.
38 compounds were obtained from the two materials, among which 32 compounds were identified , including 3 new compounds. 13 compounds were isolated from stem of Thladiantha dubia Bunge.. Ten compounds were identified as: kaempferol-7-O-α-L-rhamnoside(1),
kaempferol-3-O-β-D-(6″-O-α-L-RhamnopyRa-nosyl)glucopyranoside (2), ethyl caffeate(3), 3′, 4′-dimethoxyaceophone(4), stigmasterol(5) , cholesterol(6),α-spinasterol(7), (2R, 3S, 2′S, 4E, 8E)-Δ4(5),Δ8(9)-sphingosine-2′-hydroxyhexa-decanoylamideo(8), 3-(17Z-tetracosenyloxy)-1, 2-propanediol(9), phthalic acid bis-(2-ethylhexyl) ester(10). Compounds 3, 9, 10 were obtained from Cucurbitaceae for the first time; Compounds 1, 2 were obtained from Thladiantha for the first time; Compounds 4, 5, 6, 8 were obtained from this plant for the first time.
25 compounds were obtained from the Subergorgia suberosa(Pallas), among which 23 compounds were identified as: 4-hydroxymethyl-5β-pregn-4-ene-3, 20-dione(11), SC3-8(12), SC2-27(13), pregn-4-ene-3, 20-dione (14), 3β, 5β-pregn-20-one-3-ol (15), 3β-Pregn-5-ene-20-one-3-ol (16), 3β, 5α-Pregn-20-one-3-ol (17), 3α-hydroxy-5β-pregnan-20-one (18), cholesterol (19), (22E,24S)-5α, 8α-epidioxy-24-methyl-cholesta-6, 22-dien-3β-ol (20), subergorgic acid methyl ester (21), subergorgic acid (22), 2β-hydroxy subergorgic acid methyl ester(23), suberosanone (24), suberosenol A(25), suberosenol B (26), suberosenone (27), Batyl alcohol (28), N-hexadecanoyl-octadecasphinga-9-methy-4(E) , 8(E)-dienin (29), phthalic acid bis-(2-ethylhexyl)ester (30), phthalic acid butyl isobutyl esterm (31), 1-heptadecanol(32), 5(E), 8(E), 11(E), 14(E)-Twenty carbon arachidonic acid methyl ester (33). Compound11, 12 and 13 are new compounds.
The above researches will provide scientific basis for Thladiantha dubia Bunge and Subergorgia suberosa(Pallas) in further development and utilization. They also provide important reference for the research of chemical composition of the same genera’s other species.
引文
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