Studies On Chemical Constituents And Their Bioactivities Of Four Medicinal Plants

This dissertation basically consisted of four parts, respectively elaborated the phytochemical investigation of four medicinal plants including Liparis nervosa (Thunb.) Lindl., Senecio dianthus Franch., Daphne gracilis E. Pritz. and Zanthoxylum bungeanum Maxim. Eighty eight compounds including twenty nine new ones were isolated and identified. Complete1H-and13C-NMR spectral assignments were leading to revision of some13C NMR assignments previously made for one known compound of them.(1) The research on the chemical compositions and bioactivities of Liparis nervosaLiparis nervosa, a member of the Orchidaceae family, is a herbaceous plant that is widely distributed in China. Twenty nine compounds were isolated from the EtOH extract of the chole plant of L. nervosa by methods of column chromatography (silica gel, RP-18silica gel, Sephadex LH-20) and preparative HPLC. Their structure were identified on the basis of spectroscopic methods including IR, HR-ESI-MS, UV and NMR. Among them, twenty two new compound were determined as Nervosine I (1), Nervosine Ⅱ (2), Nervosine Ⅲ(5), Nervosine Ⅳ(6), Nervosine Ⅴ(7), Nervosine VI(8), Liparisnervoside A (9), Liparisnervoside B (10), Liparisnervoside C (11), Liparisnervoside D (12), Liparisnervoside E (14), Liparisnervoside F (15), Liparisnervoside G (16), Liparisnervoside H (17), Liparisnervoside I (18), Liparisnervoside J (19), Liparisnervoside K (20), Liparisnervoside L (21), Liparisnervoside N (22), Liparisnervoside M (23), Liparisnervoside O (24) and Liparisnervoside P (25).In this paper, all the alkaloids1-8were tested on their cytotoxic activities on RAW264.7macrophages, most of them showed no toxic, and then tested for inhibitory activities against LPS-induced NO production in this cell line under the concentration range from2.5to40μM, which suggested that all of these compounds significantly inhibited the NO production and these findings would provide significant information for the future design of anti-inflammatory agents.All the alkaloids1-8were evaluated for their cytotoxicity against human cancer cell lines including MCF-7, A549and HepG2by MTT method. However, all of them did not show obvious inhibitory activity against the tumor cells used (IC50>10μM, n=3).Liparisnervoside C (11), Liparisnervoside D (12), Liparisnervoside H (17), Liparisnervoside I (18) and Liparisnervoside J (19) were tested individually for their in vitro cytotoxicities against A549, H460, HeLa, MCF-7, Caco2, and HepG2human cell lines by the MTS method. None of these compounds showed significant inhibitory activity against the tumor cells used (IC50>10μM, n=3).(2) The research on the chemical compositions and bioactivities of Senecio dianthusFrom the aerial parts of Senecio dianthus Franch., five eremophilane glucosides (1,2,4-6), one new eremophilenolide (7) and one new furanoeremophilanen derivative (8) were isolated, together with twenty five known compounds by methods of column chromatography (silica gel, RP-18silica gel, Sephadex LH-20) and preparative HPLC. Their structures and relative configurations were elucidated on the basis of extensive spectroscopic analysis, including HR-ESI-MS, X-ray, CD,1D and2D NMR experiments. Seven new compounds were characterized as4S,5R,7S-12-O-β-D-glucopyranosyl-eremophil-9,11(12)(Z)-dien-8-one (1),4S,5R,7R-2-O-β-D-glucopyranosyl-eremophil-9,11(12)(E)-dien-8-one (2)、4S,5R-12-O-β-D-glucopyranosyl-eremophil-7(11)(Z)、9-dien-8-one (4),4S,5R-12-O-β-D-glucopyranosyl-eremophil-7(11)(E),9-dien-8-one (5),4S,5R-12-O-β-D-glucopyranosyl-eremophil-7(11)(Z),9-dien-8-one-12-oic acid (6),4S,5R-8β-ethoxy-eremophil-7(11),9-dien-8a,12-olide (7) and6-oxo-9a-angloyloxy-10βH-furanoeremophilane (8). All the compounds isolated were comprising flavonoids, sesquiterpenes, steroids and fatty acids.12-O-β-D-glucopyranosyl-eremophil-9,11(12)(E)-dien-8-one (3),4S,5R-12-O-β-D-glucopyranosyl-eremophil-7(11)(Z),9-dien-8-one (4),10β-hydroxy-eremophil-7(11)-en-8a,12-olide(10),8β,10β-dihydroxyeremophil-7(11)-en-8a,12-olide (15),1β-hydroxy-12-O-β-D-glucopyranosyl-eremophil-9,11(12)(E)-dien-8-one (17), farfugin A (18),farfugin B (19),(4aS,5S)-5,6,7,8-tetrahydro-3-hydroxy-4a,5-dimethylnaphthalen-2(4αH)-one (20), ligularenolide (22),6β-angeloyloxy-10β-hydroxy-eremophil-7(11)-en-8α,12-olide (25) and6β-hydroxy-eremophil-7(11)-en-8α,12-olide (26) were tested for their in vitro cytotoxicities against K562, MCF-7and Caco2human cell lines by the MTS method. However, all compounds did not show significant inhibitory activity against the tumor cells used. (3) The research on the chemical compositions of Daphne gracilisWe have studied on the EtOH extract of the whole plant Daphne gracilis E. Pritz. and obtained nineteen compounds by methods of column chromatography (silica gel, RP-18silica gel, Sephadex LH-20) and preparative HPLC. Their structures and relative configurations were elucidated on the basis of extensive spectroscopic analysis, including HR-ESI-MS, X-ray, CD,1D and2D NMR experiments. Compounds isolated were comprising triterpenes, bi-flavonoids, steroids, lignines and fatty acids, and all of them were isolated from this plant for the first time.(4) Study on the chemical compositions of Zanthoxylum bungeanumZanthoxylum bungeanum Maxim., a member of Rutaceae family, is widely distributed in the area of Sichuan, Hebei, Henan, Shandong and Shanxi provinces of China. As China’s traditional spices and herbs, which has a very long history. Eight known compound were isolated form the EtOAc extract of the pericarp of Z.bungeanum by methods of column chromatography (silica gel, RP-18silica gel, Sephadex LH-20). Their structures were elucidated on the basis of extensive spectroscopic analysis, including HR-ESI-MS, NMR experiments. Compound2has been isolated from this plant for the first time. Compound1is the one of important flavor substances of the Z.bungeanum Compounds3,4,5,7and8were pungent principles. All the compounds isolated were comprising acetophenones, diterpenes and aliphatic acid amides.