四种药用植物的化学成分及生物活性研究
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摘要
本论文分别对中药见血清、藏药双花千里光、川东特有植物小娃娃皮和“药食两用”的花椒果皮中化学成分进行研究,应用硅胶、RP-18反相硅胶、Sephadex LH-20葡聚糖凝胶等柱层析法并结合半制备HPLC对四种植物中的化学成分进行分离纯化,采用1D和2DNMR, HR-ESI-MS、IR、UV、CD、X-ray等光谱方法结合化学法对分离得到的化合物进行鉴定,共得到88个化合物,其中29个为新化合物,同时考察了部分化合物的抗肿瘤和抗炎活性。(1)中药见血清中生物活性成分的研究
见血清(Liparis nervosa (Thunb.) Lindl)为兰科羊耳蒜属植物,广泛分布于我国多个地方,如江西、湖南、福建、台湾、广东、广西及西南地区。见血清具有凉血止血,清热解毒等功效。本文对其化学成分进行系统的研究,从中分离并鉴定了29个化合物的结构,其中22个为新化合物,分别为：Nervosine Ⅰ(1)、Nervosine Ⅱ(2)、Nervosine Ⅲ(5)、Nervosine Ⅳ(6)、Nervosine Ⅴ(7)、Nervosine Ⅵ(8)、见血清苷A(9)、见血清苷B(10)、见血清苷C(11)、见血清苷D(12)、见血清苷E(14)、见血清苷F(15)、见血清苷G(16)、见血清苷H(17)、见血清苷Ⅰ(18)、见血清苷J(19)、见血清苷K(20)、见血清苷L(21)、见血清苷N(22)、见血清苷M(23)、见血清苷O(24)和见血清苷P(25)。7个已知化合物分别为Paludosine (3)、Auriculine (4)、Methyl3,5-bis (3-methyl-2-butenyl)-4-O-(β-D-glucopyranosyl) benzoate (13)、腺嘌呤核苷(26)、邻苯二甲酸二异丁酯(27)、对羟基苯甲醛(28)和植醇二十四烷酸酯(29),均为首次从该植物中分离得到。
本文考察了8个吡咯里西啶类生物碱：Nervosine Ⅰ(1)、Nervosine Ⅱ(2)、Paludosine (3)、Auriculine(4)、Nervosine Ⅲ(5)、Nervosine Ⅳ(6)、Nervosine Ⅴ(7)和Nervosine Ⅵ(8)对脂多糖(LPS)诱导的小鼠RAW264.7巨噬细胞产生一氧化氮(NO)的影响,与阳性对照一氧化氮合成酶抑制剂1400W相比,化合物1-8均具有很强的抗炎活性,有望开发成一种新的抗炎药物。
运用MTT法,考察了8个吡咯里西啶生物碱(化合物1-8)对乳腺癌MCF-7、肺癌A549细胞、肝癌HepG2细胞增殖的影响,研究结果表明以上8个吡咯里西啶类生物碱均无抗肿瘤活性。
运用MTS法,考察化合物见血清苷C(11),见血清苷D(12),见血清苷H(17),见血清苷Ⅰ(18)和见血清苷J(19)对体外培养的肺癌A549细胞,人肺癌H460细胞,宫颈癌HeLa细胞,乳腺癌MCF-7,结肠腺癌Caco2细胞和肝癌HepG2细胞增值的影响,结果表明以上化合物均无抗肿瘤活性。(2)藏药双花千里光中生物活性成分的研究
双花千里光(Senecio dianthus Franch.)为菊科(Asteraceae)千里光属的植物,藏药名为油苦兴嘎保,具有清热解毒,生肌愈伤及消炎的功效。本文采用多种分离方法对其化学成分进行分离纯化,共得到32个化合物,其中7个为新化合物,分别为：4S,5R,7S-12-O-β-D-glucopyranosyl-eremophil-9,11(12)(Z)-dien-8-one (1)、4S,5R,7R-12-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-8,12-olide(7)和6-oxo-9a-angloyloxy-10βH-furanoeremophilane (8)。结构涉及倍半萜、黄酮、甾体及脂肪酸类。
运用MTS法,考察化合物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-8α,12-olide(10)、8β,10β-dihydroxyeremophil-7(11)-en-8α,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-4α,5-dimethylnaphthalen-2(4aH)-one (20)、ligularenolide (22)、6β-angeloyloxy-10β-hydroxy-eremophil-7(11)-en-8α,12-olide (25)和6β-hydroxy-eremophil-7(11)-en-8α,12-olide (26)对乳腺癌MCF-7,结肠腺癌Caco2细胞和人红白血病K562细胞增值的影响,结果表明以上化合物均无抗肿瘤活性。(3)植物小娃娃皮中化学成分研究
小娃娃皮(Daphne gracilis E. Pritz.)是瑞香科瑞香属植物,产于四川东南部,生长在海拔1000-1300的灌木林中。瑞香属植物具有抗炎、免疫调节、镇痛、抑菌、抗肿瘤、抗白血病、抗HIV、降血压、抗血栓形成和抑制蛋白激酶等生物活性。至今未见小娃娃皮的相关研究报道。本文开展对小娃娃皮中生物活性成分的研究,从中分离得到19个化合物的结构,分别为β-谷甾醇(1)、木栓酮(2)、豆甾-4烯-3酮(3)、豆甾-4烯-3,6二酮(4)、羽扇豆醇(5)、豆甾醇(6)、1,3-二硬脂酸甘油酯(7)、1-二十二烷酸甘油酯(8)、2-硬脂酸甘油酯(9)、植物醇(10)、epoxyconiferyl alcohol (11)、epoxyconiferyl alcohol (12)、oleodaphnone (13)、3-Octadecanone,5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)(14)、 matairesinol (15)、neochamaejasmin A(16)、chamaejasmenin B (17)、sikokianin A(18)、 sikokianin B(19)。结构类型涉及三萜、黄酮、甾体、木脂素及脂肪酸类。以上化合物均为首次从该植物中分离得到。(4)花椒果皮中化学成分的研究
花椒(Zanthoxylum bungeanum Maxim)别名大花椒、青椒等,是芸香科花椒属植物,作为我国传统的调味品及中药材有着非常悠久的历史。本文开展对花椒果皮中化学成分的系统研究,从中分离得到8个化合物的结构,分别为花椒油素(1),hydroxy lycopersene (2),羟基-α-山椒素(3),羟基-β-山椒素(4),羟基-y-山椒素(5)和芳樟醇(6),(2E,7E,9E)-6,11-二酮-2'-羟基-N-异丁基-2,7,9-十二烷三烯酰胺(7)和(2E,6E,8E)-10-醛基-2'-羟基-N-异丁基-2,6,8十烷三烯酰胺(8)。其中化合物1为花椒中重要的风味物质之一,化合物2为首次从该植物中分离得到,化合物3、4、5、7和8为花椒中的主要麻味物质。化合物结构类型主要为苯乙酮类、萜类和脂肪酸酰胺类化合物。
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 nervosa
Liparis 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 dianthus
From 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 gracilis
We 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 bungeanum
Zanthoxylum 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.
见血清(Liparis nervosa (Thunb.) Lindl)为兰科羊耳蒜属植物,广泛分布于我国多个地方,如江西、湖南、福建、台湾、广东、广西及西南地区。见血清具有凉血止血,清热解毒等功效。本文对其化学成分进行系统的研究,从中分离并鉴定了29个化合物的结构,其中22个为新化合物,分别为：Nervosine Ⅰ(1)、Nervosine Ⅱ(2)、Nervosine Ⅲ(5)、Nervosine Ⅳ(6)、Nervosine Ⅴ(7)、Nervosine Ⅵ(8)、见血清苷A(9)、见血清苷B(10)、见血清苷C(11)、见血清苷D(12)、见血清苷E(14)、见血清苷F(15)、见血清苷G(16)、见血清苷H(17)、见血清苷Ⅰ(18)、见血清苷J(19)、见血清苷K(20)、见血清苷L(21)、见血清苷N(22)、见血清苷M(23)、见血清苷O(24)和见血清苷P(25)。7个已知化合物分别为Paludosine (3)、Auriculine (4)、Methyl3,5-bis (3-methyl-2-butenyl)-4-O-(β-D-glucopyranosyl) benzoate (13)、腺嘌呤核苷(26)、邻苯二甲酸二异丁酯(27)、对羟基苯甲醛(28)和植醇二十四烷酸酯(29),均为首次从该植物中分离得到。
本文考察了8个吡咯里西啶类生物碱：Nervosine Ⅰ(1)、Nervosine Ⅱ(2)、Paludosine (3)、Auriculine(4)、Nervosine Ⅲ(5)、Nervosine Ⅳ(6)、Nervosine Ⅴ(7)和Nervosine Ⅵ(8)对脂多糖(LPS)诱导的小鼠RAW264.7巨噬细胞产生一氧化氮(NO)的影响,与阳性对照一氧化氮合成酶抑制剂1400W相比,化合物1-8均具有很强的抗炎活性,有望开发成一种新的抗炎药物。
运用MTT法,考察了8个吡咯里西啶生物碱(化合物1-8)对乳腺癌MCF-7、肺癌A549细胞、肝癌HepG2细胞增殖的影响,研究结果表明以上8个吡咯里西啶类生物碱均无抗肿瘤活性。
运用MTS法,考察化合物见血清苷C(11),见血清苷D(12),见血清苷H(17),见血清苷Ⅰ(18)和见血清苷J(19)对体外培养的肺癌A549细胞,人肺癌H460细胞,宫颈癌HeLa细胞,乳腺癌MCF-7,结肠腺癌Caco2细胞和肝癌HepG2细胞增值的影响,结果表明以上化合物均无抗肿瘤活性。(2)藏药双花千里光中生物活性成分的研究
双花千里光(Senecio dianthus Franch.)为菊科(Asteraceae)千里光属的植物,藏药名为油苦兴嘎保,具有清热解毒,生肌愈伤及消炎的功效。本文采用多种分离方法对其化学成分进行分离纯化,共得到32个化合物,其中7个为新化合物,分别为：4S,5R,7S-12-O-β-D-glucopyranosyl-eremophil-9,11(12)(Z)-dien-8-one (1)、4S,5R,7R-12-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-8,12-olide(7)和6-oxo-9a-angloyloxy-10βH-furanoeremophilane (8)。结构涉及倍半萜、黄酮、甾体及脂肪酸类。
运用MTS法,考察化合物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-8α,12-olide(10)、8β,10β-dihydroxyeremophil-7(11)-en-8α,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-4α,5-dimethylnaphthalen-2(4aH)-one (20)、ligularenolide (22)、6β-angeloyloxy-10β-hydroxy-eremophil-7(11)-en-8α,12-olide (25)和6β-hydroxy-eremophil-7(11)-en-8α,12-olide (26)对乳腺癌MCF-7,结肠腺癌Caco2细胞和人红白血病K562细胞增值的影响,结果表明以上化合物均无抗肿瘤活性。(3)植物小娃娃皮中化学成分研究
小娃娃皮(Daphne gracilis E. Pritz.)是瑞香科瑞香属植物,产于四川东南部,生长在海拔1000-1300的灌木林中。瑞香属植物具有抗炎、免疫调节、镇痛、抑菌、抗肿瘤、抗白血病、抗HIV、降血压、抗血栓形成和抑制蛋白激酶等生物活性。至今未见小娃娃皮的相关研究报道。本文开展对小娃娃皮中生物活性成分的研究,从中分离得到19个化合物的结构,分别为β-谷甾醇(1)、木栓酮(2)、豆甾-4烯-3酮(3)、豆甾-4烯-3,6二酮(4)、羽扇豆醇(5)、豆甾醇(6)、1,3-二硬脂酸甘油酯(7)、1-二十二烷酸甘油酯(8)、2-硬脂酸甘油酯(9)、植物醇(10)、epoxyconiferyl alcohol (11)、epoxyconiferyl alcohol (12)、oleodaphnone (13)、3-Octadecanone,5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)(14)、 matairesinol (15)、neochamaejasmin A(16)、chamaejasmenin B (17)、sikokianin A(18)、 sikokianin B(19)。结构类型涉及三萜、黄酮、甾体、木脂素及脂肪酸类。以上化合物均为首次从该植物中分离得到。(4)花椒果皮中化学成分的研究
花椒(Zanthoxylum bungeanum Maxim)别名大花椒、青椒等,是芸香科花椒属植物,作为我国传统的调味品及中药材有着非常悠久的历史。本文开展对花椒果皮中化学成分的系统研究,从中分离得到8个化合物的结构,分别为花椒油素(1),hydroxy lycopersene (2),羟基-α-山椒素(3),羟基-β-山椒素(4),羟基-y-山椒素(5)和芳樟醇(6),(2E,7E,9E)-6,11-二酮-2'-羟基-N-异丁基-2,7,9-十二烷三烯酰胺(7)和(2E,6E,8E)-10-醛基-2'-羟基-N-异丁基-2,6,8十烷三烯酰胺(8)。其中化合物1为花椒中重要的风味物质之一,化合物2为首次从该植物中分离得到,化合物3、4、5、7和8为花椒中的主要麻味物质。化合物结构类型主要为苯乙酮类、萜类和脂肪酸酰胺类化合物。
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 nervosa
Liparis 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 dianthus
From 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 gracilis
We 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 bungeanum
Zanthoxylum 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.
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