鸦胆子抗肿瘤活性成分的化学研究

从苦木科植物鸦胆子[Brucea javanica(L.)Merr]干躁果实的硅胶干柱柱层析所得的活性部位中经层析分离得到7个四环三萜苦木内酯成份(A,B,C,D,E,F,G),经UV,IR,~1H-NMR,~(13)C-NMR等方法鉴定分别为鸦胆苦醇(Brusatol A),双氢鸦胆苦醇(Dihydrobrusatol,B),鸦胆因B(Bruceine B,C),鸦胆因D(Bruceine D,D),鸦胆因H(Bruceine H,E),鸦胆子甙A(Bruceoside A,F)和双氢鸦胆子甙A(Yadanzioside A,G)。据报道,鸦胆苦醇和鸦胆子甙A具有较强的抗肿瘤活性。     

Canthin-6-one,undulatone and two quassinoids from Hannoa klaineana roots

Canthin-6-one, scopoletin, undulatone and two new quassinoids, 15-desacetylundulatone and 6α-tigloyloxyglaucarubol were isolated from Hannoa klaineana roots; quassinoids were obtained in high yields from this plant material.     

Identification of an allelopathic compound from Ailanthus altissima (Simaroubaceae) and characterization of its herbicidal activity

Aqueous extracts of Ailanthus altissima bark and foliage were previously shown to be toxic to other plants. Using bioassay-directed fractionation, I isolated the phytotoxic compound from A. altissima root bark and identified it to be ailanthone, a quassinoid compound having molecular mass of 376. Ailanthone was highly phytotoxic, with concentrations of 0.7 ml/L causing 50% inhibition of radicle elongation in a standardized bioassay with garden cress (Lepidium sativum) seeds. Ailanthone exhibited potent pre- and postemergence herbicidal activity in greenhouse trials. Postcmergence activity was especially striking; even the lowest application rate (0.5 kg/ha) caused complete mortality of five of the seven plant species tested within 5 d of treatment. In contrast, the highest application rate (8 kg/ha) did not cause any detectable injury to A. altissima seedlings, indicating the presence of a protective mechanism in the producer species to prevent autotoxicity. Ailanthone was rapidly detoxified in field soil as a result of microbial activity. Applications of ailanthone equivalent to 0.5 and 4.0 kg/ha completely lost their phytotoxicity within ≤5 d when incubated in the presence of nonsterile soil. When incubated with sterile soil under identical conditions, however, ailanthone remained highly phytotoxic throughout the 21-d duration of the investigation. The high level of postemergence herbicidal activity in conjunction with its rapid biodegradation in soil suggest ailanthone may have potential for development as a natural-product herbicide.     

Herbicidal effects under field conditions of Ailanthus altissima bark extract,which contains ailanthone

Extracts of Ailanthus altissima stem bark were evaluated for herbicidal effects under field conditions in two outdoor trials. Previous investigations had shown A. altissima bark, extracted with methanol, yielded a strongly phytotoxic extract that contained ailanthone as one of the major herbicidal compounds. The first field trial investigated the level of activity and selectivity of the extract. A. altissima bark extract was sprayed post-emergence onto 17 species of weeds and crops at rates of 366, 177, 93, 47, 23, and 0 kg ha^–1. These application rates provided herbicidal activity equivalent to 4.5, 2.2, 1.1, 0.6, 0.3, and 0.0 kg of pure ailanthone per hectare, based on the results of a laboratory bioassay of extract and pure ailanthone. Strong herbicidal effects were observed within several days. Even the lowest rate caused mortality and injury in excess of 50% for nine of the 17 species, and a significant reduction in shoot biomass for 13 species. The second field trial tested the ability of bark extract to control weeds under field conditions with horticultural crops (bush bean, cauliflower, sweet corn, tomato). A. altissima bark extract was sprayed post-emergence at rates of 99, 50, 26, 13, and 0 kg ha^–1, providing herbicidal activity equivalent to 1.1, 0.6, 0.3, 0.14, and 0.0 kg of pure ailanthone per hectare. Extract treatment provided partial weed control (greatest reduction in weed biomass was 40%), but also caused serious crop injury. Bush bean was the only crop that showed a significant increase in shoot biomass and fruit yield, compared to the non-weeded control. None of the crops, regardless of application rate, showed a level of shoot biomass or fruit yield comparable to the hand-weeded control. The herbicidal effects of A. altissima bark extract declined within the first few weeks after application, supporting previous evidence that ailanthone is rapidly degraded under field conditions.     

鸦胆子化学成分及肿瘤细胞毒活性研究(英文)

从鸦胆子(Brucea javanica)种子的甲醇提取物中分离和鉴别得到11个化合物,经波谱数据分析分别鉴定为鸦胆子内酯A(1),鸦胆子素D(2),鸦胆子苷A(3),C(4),F(5),G(6),L(7),3β-羟基-孕甾-5-烯-20-酮(8),3β-羟基-5α-孕甾-20-酮(9),3-O-β-D-吡喃葡萄糖基-(1→2)-α-L-吡喃阿拉伯糖基-(20R)-孕甾-5-烯-3β,20-二醇(10)和6,22-二烯-3β-羟基5,8-过氧麦角甾(11)。其中化合物8、9和11为首次从该植物中分离得到。鸦胆子内酯A(1)和鸦胆子素D(2)对人类癌细胞株BGC-823,Huh-7,KE-97和Jurkat具有很好的细胞毒作用。     

Two quassinoid glycosides and a β-carboline-1-propionic acid from hannoa klaineana

Among the polar constituents of Hannoa klaineana roots, two new quassinoid glycosides, 15-O-β-D-glucopyranosyl-21-hydroxyglaucarubolone, 15-O-α-D-xylofuranosyl(1 → 6)-β-D-glucopyranosyl-21-hydroxy-glaucarubolone, an alkaloid, β-carboline-1-propionic acid and a coumarin glycoside, scopolin were isolated and their structures elucidated.     

Eurycomanone and eurycomanol,quassinoids from the roots of Eurycoma longifolia

From the roots of Eurycoma longifolia, used as an Indonesian folk medicine, two highly oxygenated quassinoids, named eurycomanone and eurycomanol were isolated. The structures of both new bitter principles were elucidated by NMR, MS, UV and IR.     

Chemical Constituents of the Branches and Leaves of Picrasma chinensis P.Y. Chen and Tyrosinase Inhibiting Activity

One new alkaloid, picrasine A, two new quassinoids, picralactones A−B, together with eleven known compounds were isolated from Picrasma chinensis P.Y. Chen. The structures of these compounds were determined using 1D and 2D NMR, HR-ESI-MS, and IR spectroscopic data, and by comparison with published data. Some compounds were tested for tyrosinase inhibiting activity, however, none of them exhibited strong inhibitory effects.