中华卷柏、长梗千里光及樗白皮化学成分研究
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摘要
天然产物的提取、分离、结构鉴定及理化性能与生物活性测定，即是基础研究，有重要的理论意义；同时也是应用研究，有很强的现实意义。随着科技与社会的不断发展，对传统中医药现代化的要求越来越迫切，人们既想知道中药所包含的化学成分及其生物、药理活性，也想从其所含化学成分中获得性能更优异的新药母体。这使得中药化学成分的研究越来越受到重视，尤其在我们这个中医药大国，是重要且迫切的研究课题。
本论文主要研究了三种中草药中华卷柏、长梗千里光、樗白皮的化学成分。
第一部分中华卷柏
介绍了卷柏属Selaginella及中华卷柏Selaginella sinensis的植物特征及药用性能。综述了卷柏属植物化学成分的研究进展，详细总结了主要化学成分黄酮类化合物的研究进展。总结了中华卷柏化学成分的研究概况；采用溶剂萃取、色谱层析及各种波谱分析手段，从中华卷柏的丙酮提取液中分离鉴定了7个化合物，一个新化合物selaginellin(1)，5个已知化合物阿曼托双黄酮(Amentoflavone，2)，扁柏双黄酮(Hinokiflavone，3)，银杏双黄酮(4)，β-谷甾醇(β-Sitosterol，5)，1-单取代亚油酸甘油酯(6)及一个未完全鉴定的双黄酮(7)。对selaginellin(1)及其甲基化衍生物selaginellin(1a)的结构及理化性能研究表明，化合物selaginellin(1)是一个具有新骨架的外消旋化合物(RS)-selaginellin(1)，selaginellin(1)及其衍生物1a所具有的独特物理化学性质，使其可能作为色素或酸碱指示剂或发光材料得到应用。这一成果发表在美国化学会The Journal of Organic Chemistry(2007)，72(10)，3921-3924。
第二部分长梗千里光
介绍了千里光属Senecio及长梗千里光Senecio kaschkarovii的植物特征及药用性能。综述了千里光属植物化学成分的研究进展，详细总结了主要化学成分倍半萜类化合物的研究进展，介绍了吡咯里西啶类生物碱pyrrolizidine alkaloids(PA)的特点及2000年至今的研究概况。总结了长梗千里光的研究概况：对长梗千里光的石油醚—乙醚2：1提取物(脂溶性化学成份)进行了深入研究，分离并鉴定出4个呋喃雅槛兰型倍半萜，其中化合物1、2、3为已知化合物，化合物3为首次从长梗千里光中分离得到，化合物4为一新化合物。通过CD谱及NMR、NOE差谱研究了化合物4的立体化学，并按Dreiding models构筑了该化合物分子的立体化学结构，确定该化合物应为Non-steroid型构象。这一成果发表在《高等学校化学学报》，2006，27(7)，1286-1288。
第三部分樗白皮
介绍了臭椿属Ailanthus、臭椿Ailanthus altissima及樗白皮the root bark of Ailanthus altissima的植物特征及药用性能。综述了臭椿属植物化学成分的研究进展，详细总结了主要化学成分生物碱及2000年至今所发现的三萜类化合物的研究进展。采用色谱层析及各种波谱分析手段，从樗白皮的甲醇提取液中分离鉴定了9个化合物，β-谷甾醇(β-sitosterol)(1)、β-胡萝卜甙(2)、一个苦木素类化合物shinjulactone A(3)、一个异香豆素(4)、一个异香豆素甙(5)、葡萄糖glucose(6)、生物碱1-hydroxycanthin-6-one (7)、两个生物碱糖甙canthin-6-one-5-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (8)和canthin-6-one-1-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside(9)，其中(8)、(9)为两个新化合物。这一成果发表在Journal of Asian Natural Products Research，Vol．9，No．3，April-May 2007，255-261。
The extraction, isolation and structure elucidation of natural products, as well as their physicochemical properties research and biological activity determination, are not only fundamental research but also applied research, and are very significant both for theory and for reality. With the technological progress and social development, the modernization of Traditional Chinese Medicine (TCM) will become more and more significant. We want not only to know chemical constituents, biological and pharmacological activity of TCM, but also to get new drugs from it. These all make natural products research more and more important, especially for our country.
The chemical constituents of Chinese Herbal Medicine Selaginella sinensis, Senecio kaschkarovii and the root bark of Ailanthus altissima were studied in this thesis.
Part I Selaginella sinensis
Plant characteristic and pharmacological activity of Selaginella and Selaginella sinensis are introduced. Progress on Research of chemical constituents of Selaginella, especially biflavones is reviewed. A survey of research on chemical constituents of Selaginella sinensis is summarized and, from the acetone extract of Selaginella sinensis, seven compounds were isolated and elucidated, a new compound selaginellin (1), five known compounds, Amentoflavone (2), Hinokiflavone (3), Ginkgetin (4),β-Sitosterol (5), 2,3-dihydroxypropyl-octadeca-9,12-dienoate (6) and a biflavone which is not completely determined. Study on structure and physicochemical properties of selaginellin (1) and its methoxy derivative selaginellin (la) shows that selaginellin (1) is a new, unusual racemic natural product with a novel carbon framework which has distinctive physical and chemical properties as does its derivative. Both 1 and its derivative la may be used as pigments, 1 as an acid-base indicator and la in luminescent material fields. The research achievement was published in The Journal of Organic Chemistry (2007), 72(10), 3921-3924.
Part II Senecio kaschkarovii
Characteristic and pharmacological activity of Senecio and Senecio kaschkarovii are introduced. Progress on Research of chemical constituents of Senecio, especially sesquiterpenes and pyrrolizidine alkaloids (PA) is reviewed. A survey of research on chemical constituents of Senecio kaschkarovii is summarized and, from the petroleum ether-ether extract of Senecio kaschkarovii, four compounds were isolated and elucidated, three known compounds, 1α-acetoxy-6β-angeloyloxy-10β-hydroxy-9-oxofuroeremophilane (1), 1α-methacryloyloxy-6β-Acetoxy-10β-hydroxyl-9-oxofuroeremophilane (2), 6β-isobutyloxy-10(1)-en-9-oxofuroeremophilane (3) and a new compound, 1β-acetoxy-6β-acetoxy-10β-H-9-oxofuroeremophilane (4). Compound 3 was obtained from Senecio kaschkarovii for the first time and, Compound 4 is a new compound. Compound 4's absolute configuration had been determined by CD, NMR and NOE. The research achievement was published in Chemical Journal of Chinese Universities 2006,27(7), 1286-1288.
Part III the root bark of Ailanthus altissima
Plant characteristic and pharmacological activity of Ailanthus, Ailanthus altissima and the root bark of Ailanthus altissima are introduced. Progress on Research of chemical constituents of Ailanthus, especially alkaloids and triterpenes is reviewed. From the root bark of Ailanthus altissima, nine compounds were isolated and elucidated, seven known compounds,β-sitosterol (1),β-daucosterol (2), shinjulactone A (3), 4,5-(benze-1',2')-6-hydroxy-1H-2-benzopyran-1-one (4), 4,5-(benze-1',2')-6-[O-β-D-glucopyranosyl-(1→5)-α-L-arabino-furanoside]-1H-2-benzopyran-1-one (5), glucose (6), and 1-hydroxycanthin-6-one (7), Two new alkaloidal glycosides: canthin-6-one-5-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (8) and canthin-6-one-1-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (9) named ailantcanthinosides A and B. The new compounds' structures were elucidated by one-and two-dimensional ~1H, ~(13)C NMR, FABMS, HRESIMS spectra and chemical methods. The research achievement will be published in Journal of Asian Natural Products Research (July, 2007).
本论文主要研究了三种中草药中华卷柏、长梗千里光、樗白皮的化学成分。
第一部分中华卷柏
介绍了卷柏属Selaginella及中华卷柏Selaginella sinensis的植物特征及药用性能。综述了卷柏属植物化学成分的研究进展，详细总结了主要化学成分黄酮类化合物的研究进展。总结了中华卷柏化学成分的研究概况；采用溶剂萃取、色谱层析及各种波谱分析手段，从中华卷柏的丙酮提取液中分离鉴定了7个化合物，一个新化合物selaginellin(1)，5个已知化合物阿曼托双黄酮(Amentoflavone，2)，扁柏双黄酮(Hinokiflavone，3)，银杏双黄酮(4)，β-谷甾醇(β-Sitosterol，5)，1-单取代亚油酸甘油酯(6)及一个未完全鉴定的双黄酮(7)。对selaginellin(1)及其甲基化衍生物selaginellin(1a)的结构及理化性能研究表明，化合物selaginellin(1)是一个具有新骨架的外消旋化合物(RS)-selaginellin(1)，selaginellin(1)及其衍生物1a所具有的独特物理化学性质，使其可能作为色素或酸碱指示剂或发光材料得到应用。这一成果发表在美国化学会The Journal of Organic Chemistry(2007)，72(10)，3921-3924。
第二部分长梗千里光
介绍了千里光属Senecio及长梗千里光Senecio kaschkarovii的植物特征及药用性能。综述了千里光属植物化学成分的研究进展，详细总结了主要化学成分倍半萜类化合物的研究进展，介绍了吡咯里西啶类生物碱pyrrolizidine alkaloids(PA)的特点及2000年至今的研究概况。总结了长梗千里光的研究概况：对长梗千里光的石油醚—乙醚2：1提取物(脂溶性化学成份)进行了深入研究，分离并鉴定出4个呋喃雅槛兰型倍半萜，其中化合物1、2、3为已知化合物，化合物3为首次从长梗千里光中分离得到，化合物4为一新化合物。通过CD谱及NMR、NOE差谱研究了化合物4的立体化学，并按Dreiding models构筑了该化合物分子的立体化学结构，确定该化合物应为Non-steroid型构象。这一成果发表在《高等学校化学学报》，2006，27(7)，1286-1288。
第三部分樗白皮
介绍了臭椿属Ailanthus、臭椿Ailanthus altissima及樗白皮the root bark of Ailanthus altissima的植物特征及药用性能。综述了臭椿属植物化学成分的研究进展，详细总结了主要化学成分生物碱及2000年至今所发现的三萜类化合物的研究进展。采用色谱层析及各种波谱分析手段，从樗白皮的甲醇提取液中分离鉴定了9个化合物，β-谷甾醇(β-sitosterol)(1)、β-胡萝卜甙(2)、一个苦木素类化合物shinjulactone A(3)、一个异香豆素(4)、一个异香豆素甙(5)、葡萄糖glucose(6)、生物碱1-hydroxycanthin-6-one (7)、两个生物碱糖甙canthin-6-one-5-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (8)和canthin-6-one-1-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside(9)，其中(8)、(9)为两个新化合物。这一成果发表在Journal of Asian Natural Products Research，Vol．9，No．3，April-May 2007，255-261。
The extraction, isolation and structure elucidation of natural products, as well as their physicochemical properties research and biological activity determination, are not only fundamental research but also applied research, and are very significant both for theory and for reality. With the technological progress and social development, the modernization of Traditional Chinese Medicine (TCM) will become more and more significant. We want not only to know chemical constituents, biological and pharmacological activity of TCM, but also to get new drugs from it. These all make natural products research more and more important, especially for our country.
The chemical constituents of Chinese Herbal Medicine Selaginella sinensis, Senecio kaschkarovii and the root bark of Ailanthus altissima were studied in this thesis.
Part I Selaginella sinensis
Plant characteristic and pharmacological activity of Selaginella and Selaginella sinensis are introduced. Progress on Research of chemical constituents of Selaginella, especially biflavones is reviewed. A survey of research on chemical constituents of Selaginella sinensis is summarized and, from the acetone extract of Selaginella sinensis, seven compounds were isolated and elucidated, a new compound selaginellin (1), five known compounds, Amentoflavone (2), Hinokiflavone (3), Ginkgetin (4),β-Sitosterol (5), 2,3-dihydroxypropyl-octadeca-9,12-dienoate (6) and a biflavone which is not completely determined. Study on structure and physicochemical properties of selaginellin (1) and its methoxy derivative selaginellin (la) shows that selaginellin (1) is a new, unusual racemic natural product with a novel carbon framework which has distinctive physical and chemical properties as does its derivative. Both 1 and its derivative la may be used as pigments, 1 as an acid-base indicator and la in luminescent material fields. The research achievement was published in The Journal of Organic Chemistry (2007), 72(10), 3921-3924.
Part II Senecio kaschkarovii
Characteristic and pharmacological activity of Senecio and Senecio kaschkarovii are introduced. Progress on Research of chemical constituents of Senecio, especially sesquiterpenes and pyrrolizidine alkaloids (PA) is reviewed. A survey of research on chemical constituents of Senecio kaschkarovii is summarized and, from the petroleum ether-ether extract of Senecio kaschkarovii, four compounds were isolated and elucidated, three known compounds, 1α-acetoxy-6β-angeloyloxy-10β-hydroxy-9-oxofuroeremophilane (1), 1α-methacryloyloxy-6β-Acetoxy-10β-hydroxyl-9-oxofuroeremophilane (2), 6β-isobutyloxy-10(1)-en-9-oxofuroeremophilane (3) and a new compound, 1β-acetoxy-6β-acetoxy-10β-H-9-oxofuroeremophilane (4). Compound 3 was obtained from Senecio kaschkarovii for the first time and, Compound 4 is a new compound. Compound 4's absolute configuration had been determined by CD, NMR and NOE. The research achievement was published in Chemical Journal of Chinese Universities 2006,27(7), 1286-1288.
Part III the root bark of Ailanthus altissima
Plant characteristic and pharmacological activity of Ailanthus, Ailanthus altissima and the root bark of Ailanthus altissima are introduced. Progress on Research of chemical constituents of Ailanthus, especially alkaloids and triterpenes is reviewed. From the root bark of Ailanthus altissima, nine compounds were isolated and elucidated, seven known compounds,β-sitosterol (1),β-daucosterol (2), shinjulactone A (3), 4,5-(benze-1',2')-6-hydroxy-1H-2-benzopyran-1-one (4), 4,5-(benze-1',2')-6-[O-β-D-glucopyranosyl-(1→5)-α-L-arabino-furanoside]-1H-2-benzopyran-1-one (5), glucose (6), and 1-hydroxycanthin-6-one (7), Two new alkaloidal glycosides: canthin-6-one-5-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (8) and canthin-6-one-1-o-β-D-xylopyranosyl-(1→6)-β-D-glucopyranoside (9) named ailantcanthinosides A and B. The new compounds' structures were elucidated by one-and two-dimensional ~1H, ~(13)C NMR, FABMS, HRESIMS spectra and chemical methods. The research achievement will be published in Journal of Asian Natural Products Research (July, 2007).
引文
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[1] 华东师范大学，上海师范学院，南京师范大学编．植物学 下册，北京：人民教育出版社，1982，289-293．
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