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题名: 三种药用植物的化学成分和生物活性研究
作者: 雷春
学位类别: 博士
答辩日期: 2008-01-22
授予单位: 中国科学院昆明植物研究所
授予地点: 昆明植物研究所
导师: 孙汉董
关键词: 五味子属 ; 南五味子属 ; 黄花棯属 ; 三萜 ; 木脂素 ; 植物蜕皮激素 ; 抗HBV活性 ; 生物合成
学位专业: 植物学
中文摘要: 本论文由三章组成。第一章详细论述了合蕊五味子(Schisandra propinqua var. propinqua)和冷饭藤(Kadsura oblongifolia Merr.)两种五味子科药用植物藤茎的化学成分研究情况,并对其中的部分化合物进行了相关生物活性的测定。第二章介绍了滇产拔毒散(Sida szechuensis Matsuda)的化学成分和相关生物活性的研究情况。论文第三章较为全面的综述了植物三萜的生物合成途径及其关键酶的研究进展。 利用各种色谱技术,波谱分析、以及晶体X-衍射分析等方法,从上述三种植物中共分离鉴定了112个化合物,化合物结构类型涉及三萜、木脂素、甾体、香豆素、脂肪酸和其它酚性成分等。其中新化合物37个,全部为来源于合蕊五味子藤茎的三萜类成分,共涉及11种三萜骨架,几乎涵盖了目前所有五味子属(Schisandra)三萜的骨架类型。这一研究也将目前从五味子属分离到的三萜骨架在生源上紧密地联系在一起,为五味子属植物中这些结构新奇的三萜类化合物存在的合理性从生源上提供了直接的证据,也极大地丰富了五味子属三萜的化学多样性。首次分离得到了2种高度氧化的含有复杂氧环的三萜类化合物和1个新颖的2,3-seco-lanostane 型骨架三萜。 对分离得到的部分化合物进行了体外细胞毒、抗HIV-1、抗HBV以及对心肌细胞缺氧的保护作用的活性测试,首次发现其中的一个高氧化三萜(26)初步显示了与对照3TC相当的抗HBV活性,有进一步研究的价值。 第一章 两种五味子科药用植物藤茎的化学成分和生物活性研究 第一节 合蕊五味子藤茎的化学成分和生物活性研究 合蕊五味子(Schisandra propinqua (Wall.) Baill. var. propinqua)为五味子科(Schisandraceae)五味子属(Schisandra)合蕊五味子(Schisandra propinqua (Wall.) Baill.)的原变种,产于云南西北部、西藏西部。生于海拔2000-2200m 的河谷、山坡常绿阔叶林中。其根、茎、叶、果实均可入药,根及茎称鸡血藤,治风湿骨痛、跌打损伤等症。从采自云南腾冲的合蕊五味子藤茎部分分离鉴定了80个化合物(包括37个新化合物),其中三萜类化合物54个,新三萜37个。 三萜的碳骨架涉及schisanartane(1-15, 39-48)、 schiartane(16-21, 38, 49)、 18(13→14)-abeo-schiartane(22-26, 50)、18-nor-schiartane(27-30, 51-52)、 pre-schisanartane(31-32)、 wuweiziartane(33-34)、3,4:9,10-seco-cycloartane(35)、3,4-seco-cycloartane(36)、2,3-seco-lanostane(37)以及常见的cycloartane(53)和lanostane(54)等11种结构类型。首次分离得到了2种高度氧化的含有复杂氧环的三萜类化合物(1, 24)和1个新颖的2,3-seco-lanostane 型骨架三萜(37)。合蕊五味子是迄今报道的五味子科中三萜类型最丰富的品种。部分化合物的体外细胞毒、抗HIV-1和抗HBV活性筛选表明,三萜化合物26显示了与对照3TC相当的抗HBV活性,值得进一步深入研究。 第二节 冷饭藤藤茎的化学成分和生物活性研究 冷饭藤(Kadsura oblongifolia Merr.)为五味子科(Schisandraceae)南五味子属(Kadsura)植物,又名饭团藤。生于250-1500米山坡疏林中、沟边湿润处。分布于云南、广东、广西、海南等地,中国福建和台湾以及越南首次记录。冷饭藤的藤或根为著名的中药吹风散,有治感冒、风湿痹痛、腹泻、呕吐、跌打损伤等功效。从购自昆明市菊花村药材市场的冷饭藤藤茎中分离鉴定了20个化合物,出乎意料的是该种的主要成分与五味子科(Schisandraceae)其它种的化合物类型差别较大,主要为β-sitoserol、1-octadecanol以及二苯基四氢呋喃并四氢呋喃型木脂素(1-9)。究其原因,除了可能因为种间、采收期导致的化学成分复杂外,更有可能是市场上所卖药材的混杂所致(相似种、不同采收期、不同采集地的混在一起销售)。所测化合物均没有显示抗HIV-1活性。 第二章 拔毒散的化学成分和生物活性研究 拔毒散(Sida szechuensis Matsuda)为锦葵科(Malvaceae)黄花棯属(Sida)植物的全草,生于灌木丛或山坡,分布四川、贵州、云南、广西等地。具有清热解毒,活血祛瘀、治急性乳腺炎,急性扁桃体炎,疔疮,肿毒,肠炎,菌痢,妇女经闭,跌打损伤的功效。已有的研究显示植物脱皮激素是它的主要成分。从采自云南大理的拔毒散全草的70%丙酮提取物中分离鉴定了12个化合物,大部分成分是植物脱皮激素,首次分得了一个芳香酰胺和一个三萜。体外抗HBV和对心肌细胞缺氧的保护作用的活性测试均没有发现活性化合物。 第三章 植物三萜的生物合成途径及其关键酶的研究进展 综述了起源于角鲨烯或环氧角鲨烯的植物三萜的生物合成途径,并对部分典型的三萜合成酶相关基因的克隆和酶学机制方面的研究进展做了简要介绍。
英文摘要: This dissertation comprises three chapters. Reports in the chapter 1 were about the investigations on the chemical constituents and bioactivities of two members in Schisandraceae family. In the second chapter, the isolation and identification of the chemical constituents from Sida szechuensis Matsuda of the family Malvaceae were described. In the last chapter, the research advance of the biosynthetic mechanism and releated key triterpene synthases of plant triterpenes derived from squalene or oxidosqualene were summarized. From the above three species, 112 compounds including triterpenoids, lignans, steroids, coumarins, fatty acids and other phenols were purified by means of chromatography methods and identified on spectral evidences. Among them, 37 compounds isolated from the stems of Schisandra propinqua var. propinqua were showed to be new ones. Two kinds of highly oxygenated triterpenoids possessing newly built oxygen rings and one novel 2,3-seco-lanostane skeleton were first discovered from this species. Up to now, it is unprecedented that so many new biogenetic closely related triterpenoids with great skeletal diversity were discovered in one species, which provided direct evidence for the existing rationality of novel skeleton triterpenoids from genus Schisandra . Some compounds were evaluated for their in vitro bioacitivies including cytotoxic activity against three kinds of human tumor cell lines, anti-HIV-1 activity, anti-HBV activity, and protecting effect of rat myocardial cells from injury induced by hydrogen peroxide. A new highly oxygenated triterpenoid, 26, was found to show potential of anti-HBV activity. Section 1 of chapter 1. Study on the Chemical Constituents and Bioactivitis of Schisandra propinqua var. propinqua Schisandra propinqua (Wall.) Baill. var. propinqua belongs to the genus Schisandra of the family Schisandraceae. It is a climbing plant widely distributed in the northwest of Yunnan and the western part of Tibet in China. The roots, stems, leaves, and fruits have all been used in folk medicine. And the stems can be used for the treatment of rheumatic lumbago, traumatic injury, and related diseases. Phytochemical investigation on the stems of this plant resulted in the isolation of 37 new compounds (1-37) together with 43 known ones (38-80). 54 of them are triterpenoids involving 11 skeletons including schisanartane (1-15, 39-48), schiartane (16-21, 38, 49), 18(13→14)-abeo-schiartan (22-26, 50), 18-nor-schiartane (27-30, 51-52), pre-schisanartane (31-32), wuweiziartane (33-34), 3,4:9,10-seco-cycloartane (35), 3,4-seco-cycloartane (36), 2,3-seco-lanostane (37), cycloartane (53) and lanostane (54). Four novel highly oxygenated triterpenoids (1and 24) with newly built oxygen rings and one novel 2,3-seco-lanostane skeleton (37) were first discovered from this genus. Evaluation of cytotoxic activity against three kinds of human tumor cell lines, anti-HIV-1 and anti-HBV activity showed that only 26 has potential of anti-HBV activity. 1. propindilactone A (1)* 2. propindilactone B (2)* 3. propindilactone C (3)* 4. propindilactone D (4)* 5. propindilactone E (5)* 6. propindilactone F (6) * 7. propindilactone G (7)* 8. propindilactone H (8)* 9. propindilactone I (9)* 10. propindilactone G (10)* 11. propindilactone K (11)* 12. propindilactone L (12)* 13. propindilactone M (13)* 14. propindilactone N (14)* 15. propindilactone O (15)* 16. propindilactone P (16)* 17. propindilactone Q (17)* 18. propindilactone R (18)* 19. propindilactone S (19)* 20. propindilactone T (20)* 21. propindilactone U (21)* 22. propindilactone V (22)* 23. propindilactone W (23)* 24. propindilactone X (24)* 25. propindilactone Y (25)* 26. propindilactone Z (26)* 27. schipropindilactone A (27)* 28. schipropindilactone B (28)* 29. schipropindilactone C (29)* 30. schipropindilactone D (30)* 31. pre-schisanartanin C (31)* 32. pre-schisanartanin D (32)* 33. propintrilactone A (33)* 34. propintrilactone B (34)* 35. propinic acid A (35)* 36. propinic acid B (36)* 37 lanopropic acid (37) * 38. micrandilactone B (38) 39. lancifodilactone C (39) 40. henridilactone D (40) 41. micrandilactone E (41) 42. micarndilactone D (42) 43. micrandilactone A (43) 44. rubriflordilactone C (44) 45. henridilactone A (45) 46. henridilactone B (46) 47. pubescendilactone B (47) 48. pubescendilactone A (48) 49. micrandilactone C (49) 50. wuweizidilactone D (50) 51. wuweizidilactone B (51) 52. wuweizidilactone H (52) 53. schizandronic acid (53) 54. 3β-hydroxy-lanost-9(11),24-dien-26-oic acid (54) 55. gomisin N (55) 56. angeloylgomisin O (56) 57. epigomisin O (57) 58. isogomisin O (58) 59. 6-O- benzoylgomisin O (59) 60. isogomisin O (60) 61. angeloylisogomisin O (61) 62. schisandrin C (62) 63. wuweilignan A (63) 64. angeloyl-(+)-gomisin K3 (64) 65. gomisin J (65) 66. gomisin E (66) 67. methylisogomisin O (67) 68. (+)-γ-Schizandrin (68) 69. (-)-Gomisin L1 (69) 70. gomisin K3 (70) 71. schisandrin A (71) 72. gomisin M2 (72) 73. pre-gomisin (73) 74. meso-dihydroguaiaretic acid (74) 75. isoanwulignan (75) 76. sphenanlignan (76) 77. prinsepiol (77) 78. (-)-epicatechin (78) 79. β-sitoserol (79) 80. daucosterol (80) Section 2 of chapter 1. Study on the Chemical Constituents and Bioactivity of Kadsura oblongifolia Merr. Kadsura oblongifolia Merr. is one member of Schisandraceae family, which mainly distributes in southwest China. The stems and roots of this plant are widely used as folk medicine to treat cold, rheumatic lumbago, traumatic injury, diarrhea, and vomiting. Instead of typical components of Schisandraceae family, 20 compounds, β-sitoserol and 1-octadecanol as the main components, were isolated from this plant purchased from Juhuacun Traditional Chinese Herbal market in Kunming. And none of them showed anti-HIV-1 activity. Confusion of the raw material may be attributed to this result. 1. (+)methylpluviatilol (1) 2. (-)-kobusin (2) 3. (+)-epimagnolin A (3) 4. (+)-magnolin (4) 5. (+)-syringaresinol(5) 6. (+)-episyringaresinol (6) 7. (+)-eudesmin (7) 8. yangambin (8) 9. (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0]-octane (9) 10. maslinic acid (10) 11. alphitolic acid (11) 12. ursolic acid (12) 13. 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (13) 14. 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (14) 15. 2,6-Dimethoxy-1-acetonylquinol (15) 16. 1-(4-hydroxy-3-methoxyphenyl)ethanone (16) 17. 4-hydroxy-3-methoxybenzoic acid (17) 18. 4-hydroxy-3-methoxybenzaldehyde (18) 19. β-sitoserol (19) 20. 1-octadecanol (20) Chapter 2. Study on the Chemical Constituents and Bioactivity of Sida szechuensis Matsuda Sida szechuensis Matsuda (Malvaceae) is a perennial shrub, widely spread throughout the highland of southwest China. The whole plant of Sida szechuensis used as crude drug is extremely effective on clearing away heat and drawing out poison. It is widely used in Chinese traditional medicine for treatments of blood stasis, disordered menses, acute mastitis, tonsil inflammation, enteritis, ulcers, furuncle, and dysentery. Previous phytochemical investigations on this species showed the main constituents were ecdysones. Investigation on this plant collected from Dali County in Yunnan province resulted in 12 compounds. In addition to the eight known phytoecdysones (2-9), one alkamide (1) and one triterpene, α-Onocerin (7) were first isolated from this species. None of them showed anti-HBV activity and protecting effect of rat myocardial cells from injury induced by hydrogen peroxide. 1. (E)-3-(3-hydroxy-4-methoxyphenyl)-N-(4-hydroxyphenethyl) acrylamide (1) 2. rubrosterone (2) 3. dihydrorubrosterone (3) 4. poststerone (4) 5. rubrosterone-2,3-monoacetonide (5) 6. α-ecdysone (6) 7. 20-hydroxyecdysone (7) 8. 25-hydroxyecdysone-20,22-monoacetonide (8) 9. 20-hydroxyecdysone-25-monoacetate (9) 10. α-onocerin (10) 11. β-sitoserol (11) 12. scopoletin(12) Chapter 3. Enzymatic cyclization of squalene and oxidosqualene to diverse plant triterpenes Plants produce a wealth of triterpenes that derived from squalene and oxidosqualene. This review covers recent advances in the chemistry and enzymatic mechanism of plant triterpenes biosynthesis.
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/242
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三种药用植物的化学成分和生物活性研究.雷春[d].中国科学院昆明植物研究所,2008.20-25
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