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Phytochemical studies on Aster pilosus and other medicinal plants.

机译:紫杉和其他药用植物的植物化学研究。

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摘要

The defatted MeOH extract of Aster pilosus Willd. (Asteraceae) was found to exhibit significant anti-inflammatory activity in rats at oral doses of 25, 50 and 100 mg/kg in the carrageenin-induced pedal edema and adjuvant-induced arthritis assays. Bioassay-guided fractionation of the active CHCl 3-soluble fraction resulted in the isolation of six new triterpenes, hop-17 (21)-en-3β-ol (1), hop-17 (21)-en-3β-ol ( 2), adianene-3β-ol (10), 23-hydroxymelaleucic acid (12), 24-acetoxyl-2α3α-dihydroxyurs-12-en-28-oic (13) and asterpilosin F (16). Also isolated from this fraction were the known compounds friedelin (3), epifriedelanol (4), friedelanol (5), friedelanol-3α-yl-acetate (6), α-spinasterol (7), α-spinasterol-3β-yl-acetate (8), α-spinasterol-3-O-β-D-glucopyranoside (9) and bauerenyl acetate (18). It is noteworthy that oleanolic acid (15), friedelin (3), friedelanol (5), epifriedelanol (4) and friedelanol-3α-yl-acetate (6) have previously been reported to be active in the carrageenin-induced rat pedal edema assay.; During the course of a large scale re-isolation of the cancer chemopreventive lignan secoisolariciresinol diglucoside (SDG, 23) from flaxseed [(Linus usitatissimum L. Linaceae], a new flavonoid glycoside, herbacetin 3,8-O-diglucopynanoside (26), the known flavonoids, herbacetin 3,7-O-dimethyl ether ( 28), kaempferol 3,7-O-diglucopynanoside (29 ), and the known lignan, (−)-pinoresinol diglucoside ( 30) were obtained. The stereochemistry of SDG (23) was defined for the first time by use of extensive 1D- and 2D-NMR spectral analyses and [α]D measurements. The isolates 26, 28, 29, 30, as well as the aglycone 27 of 26 were evaluated for antioxidant activity with the non-glycosylated herbacetin (27) and herbacetin 3,7- O-dimethyl ether (28) showing potent antioxidant activity.; A new ent-kaurene diterpene, megathyrin B (35 ), 1α,7β,11β,15β-tetrahydroxy- ent-7α,20-oxido-kaur-16-ene, was isolated from the cytotoxic MeOH extract prepared from the leaves of Isodon megathyrisus (Diels) H. W. Li (Labiatae).; A novel alkaloid, (1R, 2S)-(−)-mangochinine (38), possessing a rare dibenzopyrrocoline nucleus in its structure, was isolated from Manglietia chingii Dandy (Magnoliaceae). Its stereochemistry was determined on the basis of optical rotation measurements and extensive 1D- and 2D-NMR spectral analyses on its diacetylated derivative.; Finally, a unique inseparable epimeric diterpene pair was isolated from the stems and leaves of Isodon irrarata (Forrest) Hara (Labiatae) and was named irroralactone (39). Its structure in the crystalline state was unambiguously determined by X-ray crystallography. Compound 39 was shown to have very different epimeric ratios and conformation in MeOH-d4, C5D5N, DMSO- d6 and CDCl3 solutions.
机译: Aster pilosus Will的脱脂MeOH提取物。在角叉菜胶诱发的脚蹬水肿和佐剂诱发的关节炎试验中,发现口服菊苣(菊科)在大鼠中的口服,剂量分别为25、50和100 mg / kg时具有显着的抗炎活性。活性CHCl 3 可溶性级分的生物测定指导分馏导致分离出六个新的三萜,hop-17(21)-en-3β-ol( 1 ) ,蛇麻草(17)(21)-en-3β-ol( 2 ),腺嘌呤-3β-ol( 10 ),23-羟基美铝酸( 12 < / bold>),24-乙酰氧基-2α3α-dihydroxyurs-12-en-28-oic( 13 )和星菌素F( 16 )。从该馏分中还分离出已知化合物Friedelin( 3 ),Epifriedelanol( 4 ),Friedelanol( 5 ),Friedelanol-3α-yl -乙酸盐( 6 ),α-斯潘甾固醇( 7 ),α-斯潘那固醇-3β-乙酸基酯( 8 ),α-斯潘甾醇-3- O -β-D-吡喃葡萄糖苷( 9 )和醋酸鲍尔烯基乙酸酯( 18 )。值得注意的是齐墩果酸( 15 ),弗瑞德林( 3 ),弗瑞德罗醇( 5 ),表弗瑞德罗醇( 4 )和3-乙酸弗雷代诺醇( 6 )以前据报道在角叉菜胶诱导的大鼠脚踏板浮肿测定中具有活性。在从亚麻籽[( Linus usitatissimum L。Linaceae)](一种新的类黄酮)中化学预防性预防性木脂素木脂蛋白-花生四烯酸二糖苷(SDG, 23 )的大规模分离过程中糖苷,除草素3,8- <斜体> O -二葡萄糖基吡喃糖苷( 26 ),已知的类黄酮,草精3,7- <斜体> O -二甲醚(<粗体> 28 ),山emp酚3,7- O -二葡萄糖吡喃糖苷( 29 )和已知的木脂素(-)-松脂醇二葡萄糖苷(获得30 ),并通过广泛的1D和2D-NMR光谱分析以及[α] D <定义了SDG的立体化学( 23 )。 / sub>测量值。分离株 26 28 29 30 和糖苷配基 27 )和除草素3,7- O 评估 26 中的> 27 的抗氧化活性。 -二甲基醚( 28 )显示有效的抗氧化活性。一种新的 -月桂烯二萜,megathyrin B( 35 ),1α,7β,11β,15β-tetrahydroxy- ent -7α,20-从由Iitaldon megathyrisus(itals)(Diels)HW Li(Labiatae)的叶子制备的具有细胞毒性的MeOH提取物中分离出了氧化kaur-16-ene。一种新型生物碱,(1 R ,2 S )-(-)-芒果甜菜碱( 38 ),其结构中具有稀有的二苯并吡咯啉碱核是从 Manglietia chingii Dandy(木兰科)中分离出来的。根据其旋光度测量以及对其二乙酰化衍生物的广泛1D-和2D-NMR光谱分析,确定了其立体化学。最后,从 Isodon irrarata (Forrest)Hara(Labiatae)的茎和叶中分离出一个独特的不可分离的二萜对,并命名为irroralactone( 39 )。通过X射线晶体学明确地确定了其处于结晶状态的结构。化合物 39 在MeOH- d 4 ,C 5 D < sub> 5 N,DMSO- d 6 和CDCl 3 解决方案。

著录项

  • 作者

    Qiu, Sheng-Xiang.;

  • 作者单位

    University of Illinois at Chicago, Health Sciences Center.;

  • 授予单位 University of Illinois at Chicago, Health Sciences Center.;
  • 学科 Chemistry Pharmaceutical.; Health Sciences Pharmacy.; Chemistry Organic.
  • 学位 Ph.D.
  • 年度 1998
  • 页码 205 p.
  • 总页数 205
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 药物化学;药剂学;有机化学;
  • 关键词

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