1.有毒植物薄叶山柑和苦藤的化学成分及生物活性研究 2.当归化学成分及指纹图谱研究
摘要
薄叶山柑(Capparis tenera Dalz.)是白花菜科(Cappaddaceae)主要有毒属——槌果藤属(Capparis L.)的一种有毒植物。该属植物多为常绿灌木或小乔木,全世界约250-400种,我国约32种,除新疆、西藏西部各产一种外,其余分布西南至台湾。据报道其茎皮的氯仿提取物有神经毒性。目前,还没有关于该植物化学成分研究的报道。本所药理室筛选结果表明薄叶山柑(根)95%乙醇总提取物、石油醚部位、石油醚部位沉淀、乙酸乙酯部位和正丁醇部位都有较好的抗氧化活性。
苦藤(Neoalsomitra integrifoliola(Cogn.)Hutch.)是葫芦科(Cucurbitaceae)翅子瓜亚族(subtrib.Zanoninae)棒槌瓜属(Neoalsomitra)的一种有毒植物。该属植物多为攀援灌木或草质藤本,全世界共约12种,我国有2种,分别为棒槌瓜(苦藤)和藏棒槌瓜,产华南、西南和台湾。据报道苦藤的茎、叶和果实有毒,能引起剧烈腹泻,严重时手足抽搐。本所药理室筛选结果表明苦藤(叶)95%乙醇总提取物、乙酸乙酯部位和正丁醇部位都显示明显的抗炎活性和细胞毒活性。
为从天然产物中寻找生物活性成分,本论文运用多种色谱方法和波谱技术,在生物活性指导下,对上述2种有毒植物进行了系统的化学成分研究。从2种植物中共分离得到56个化合物,鉴定了49个化合物的结构,其中9个为新化合物。这9个新化合物分属于4种结构类型,包括4个新的木脂素苷类化合物(从薄叶山柑分离得到的化合物1,2,从苦藤分离得到的化合物2,3);2个新的生物碱苷类化合物(从薄叶山柑分离得到的化合物4,5);2个新的酚苷类化合物(从薄叶山柑分离得到的化合物7,10);和1个新的倍半萜苷类化合物(从苦藤分离得到的化合物1)。40个已知化合物,分属于9种结构类型。包括4个已知的木脂素苷类化合物,1个已知的木脂素类化合物,1个已知的生物碱苷类化合物,10个已知的酚苷类化合物,1个已知的酚类化合物,4个已知的黄酮苷类化合物,2个甾醇类化合物,3个芳香酸以及14个其它类化合物。
从薄叶山柑Capparis tenera Dalz.(Capparidaceae)(根)95%乙醇提取物的正丁醇及石油醚萃取部位中共分离鉴定了24个化合物,分别为:3个木脂素苷类化合物:(+)-lyoniresin-4'-ylβ-glucopyranoside(1),(-)-8'-epi-lyoniresin-4-ylβ-glucopyranoside(2),(+)-lyoniresin-4-ylβ-D-glucopyranoside(3);3个生物碱苷类化合物:1H-indole-3-acetamideβ-glucopyranoside(4),1H-indole-3-carbaldehydeβ-glucopyranoside(5),cappariloside A(6);11个酚苷类化合物:1-(2,6-dimethoxy-benzoic acid)-6-O-syringoyl-β-glucopyranoside(7),clemochinenosideA(8),clemochinenoside B(9),2,6-dimethoxy-p-hydroquinone1-O-β-6-O-(3-hydroxy-3-methylglutaryl)glucopyranoside(10),2,6-dimethoxy-phydroquinone1-O-β-D-glucopyranoside(11),erigeside C(12),glucosuringic acid(13),vanillic acid 4-O-β-D-glucoside(3-methoxy 4-glucosyl-benzoic acid)(14),4-O-β-D-glucopyranosylbenzoate(15),tachioside(16),3',5'-dimethoxy-4-O-β-D-glucopyranosyl-cinnamic acid(17);1个酚类化合物:2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(18);1个黄酮苷类化合物:金合欢素7-O-芸香糖苷(19);以及葡萄糖(20),蔗糖(21),硬脂酸(22),甘油单十八烷酸酯(23),β-谷甾醇(24)。化合物1,2为木脂素苷类新化合物,化合物4,5为生物碱苷类新化合物,化合物7,8为酚苷类新化合物。在得到的已知化合物中,有11个化合物为首次从白花菜科得到,分别为化合物3,8,9,11-18;黄酮苷类化合物19为首次从该属分离得到。
从苦藤Neoalso mitra integrifoliola(Cogn.)Hutch.(cucurbitaceae)(叶)95%乙醇提取物的正丁醇及乙酸乙酯萃取部位中共分离鉴定了25个化合物,分别为:1个倍半萜苷类化合物:(6R,9R)-blumenylα-L-rhamnopyranosyl-(1→6)-β-D-glupyranoside(1);5个木脂素苷类化合物:8,8'-E-7',8'-E-5,5'-dimethoxy-7-oxolariciresinol-9'-O-β-D-xylopyranoside(2),(7S,8R)-二氢化脱氢松柏醇9'-O-β-D-芹糖-(1→6)-O-β-D-葡萄糖苷(3),二氢化脱氢松柏醇9'-O-β-D-葡萄糖苷(4),nudiposide(5),9-O-β-D-xylopyranoside of icariol A_2和其差向异构体9-O-β-D-xylopyranoside of 8,8'-E-icariol A_2(6);1对木脂素类化合物:icariol A_2和其差向异构体8,8'-E-icariol A_2(7);1个酚苷类化合物:2-methoxy-4-trans-propenyl-phenolα-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(8);3个黄酮苷类化合物:芦丁(9),山柰酚-3-O-(6"-O-α-L-鼠李吡喃糖基)-β-D-葡萄吡喃糖苷(10),异鼠李素-3-O-(6"-O-α-L-鼠李吡喃糖基)-β-D-葡萄吡喃糖苷(11);2个甾醇及其苷类化合物:α-菠甾醇(12),α-菠甾醇3-O-β-D-葡萄吡喃糖苷(13);3个芳香酸:3,4-二羟基苯甲酸(14),4-羟基苯甲酸(15),没食子酸(16);以及绿原酸甲酯(17),2-苯基乙醇芸香糖苷(18),表木栓醇(19),asteruacerebrosided(20),柴胡神经酰胺(21),鸟苷(22),腺苷(23),肌-肌醇(24),硬脂酸(25)。化合物1为倍半萜苷类新化合物,化合物2,3为木脂素苷类新化合物,化合物8为酚苷类新天然产物。所得21个已知化合物均为从该属首次分离得到。
体外药理模型筛选结果表明:(1)薄叶山柑(根)95%乙醇提取物正丁醇部位4个化合物4,10,13,17有极弱的抗氧化活性,在浓度为1×10~(-6)mol/L时,抑制Fe~(2+)半胱氨酸诱导的肝微粒体脂质过氧化物产生率为12.0-19.0%;共6个化合物5,7,9,11,17,19有弱的抗炎活性,在浓度为1×10~(-5) mol/L时,抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放率为13.2-18.8%;共9个化合物4,5,6,7,8,9,11,13,17无细胞毒活性(IC_(50)＞50μg/ml)。(2)苦藤(叶)95%乙醇提取物正丁醇部位6个化合物1,12,14,20,21,23有极弱的抗氧化活性,在浓度为1×10~(-6)mol/L时,抑制Fe~(2+)半胱氨酸诱导的肝微粒体脂质过氧化物产生率为11.1-19.0%;共5个化合物1,5,11,12,14有弱的抗炎活性,在浓度为1×10~(-5) mol/L时,抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放率为16.7-25.0%;共3个化合物14,16,19,对A549(人肺腺癌细胞),Bel-7402(人肝癌细胞),BGC-823(人胃癌细胞),HCT-8(人结肠癌细胞),MCF-7(人乳腺癌细胞)细胞有中等的细胞毒活性(1μg/ml＜IC_(50)＜10μg/ml)。
Capparis tenera Dalz.is a toxic species of genus Capparis,which is one of the the main toxic genuses of family Capparidaceae.Capparis comprises about 250-400 species,most of them are bushes or arbores.About 32 species are distributed from southwest to Taiwan in China,excluding one in Xinjiang and west of Xizang respectively.It was reported that the chloroform extracts of its stem bark showed neural toxicity.However,no chemical investigations of this plant had been reported by now.The results of bioassay displayed that the crude extracts of 95%alcohol, petroleum ether,deposition of petroleum ether,ethyl acetate,and n-butanol showed good antioxidant activities。
Neoalsomitra integrifoliola(Cogn.) Hutch.is a toxic species of genus Neoalsomitra of subtrib.Zanoninae of cucurbitaceae.The genus Neoalsomitra comprises about 12 species,most of them are rosebush or herbaceous vine.Two species of them,N.integrifoliola and N.clavigera distributed in south,southwest and Taiwan in China.It was reported that the stems,leaves and fruits of N.integrifoliola are toxic and the toxin can cause severe diarrhea,and even tetany.The results of bioassay displayed that 95%alcohol crude extracts of leaves of Neoalsomitra integrifoliola,and fractions of ethyl acetate,n-butanol showed obvious anti-inflammatory activity and cytotoxity.
In order to find bioactive compounds from natural products,we studied systematically on chemical constituents of the two toxic plants mentioned above with guidance of bioactivities screening.Based on various chromatographic methods and spectral technologies,56 compounds were obtained from the two plants,among which 49 compounds were identified,including 9 new compounds.These new compounds belong to four structures:4 new lignan glycosides(compounds 1,2 obtained from C. tenera,compounds 2,3 obtained from N.integrifoliola);2 new alkaloid glycosides (compounds 4,5 obtained from C.tenera);2 new phenolic glycosides(compounds 7, 10 obtained from C.tenera);1 new sesquiterpene glycoside(compounds 1 obtained from N.integrifoliola).40 known compounds belong to nine structures:4 known lignan glycosides;1 known lignan compound;1 known alkaloid glycosides;10 known phenolic glycosides;1 known phenolic compound;4 known flavnoid glycosides;2 known sterol compounds;3 aromatic acid compounds;and 14 other compounds。
Twenty-four compounds were obtained and identified from 95%alcohol extracts (n-BuOH and petroleum ether extracts) of the roots of Capparis tenera.They are three lignan glucosides:(+)-lyoniresin-4'-ylβ-glucopyranoside(1), (-)-8'-epi-lyoniresin-4-ylβ-glucopyranoside(2),(+)-lyoniresin-4-ylβ-D-glucopyranoside(3);three indole alkaloid glucosides:1H-indole-3-acetamideβ-glucopyranoside(4),1H-indole-3-carbaldehydeβ-glucopyranoside(5), cappariloside A(6);eleven phenolic glucosides:1-(2,6-dimethoxy-benzoic acid)-6-O-syringoyl-β-glucopyranoside(7),clemochinenoside A(8), clemochinenoside B(9),2,6-dimethoxy-p-hydroquinone 1-O-β-6-O-(3-hydroxy-3-methylglutaryl) glucopyranoside(10),2,6-dimethoxy-p-hydroquinone 1-O-β-D-gluco pyranoside(11),erigeside C(12),glucosuringic acid(13),vanillic acid 4-O-β-D-glucoside(3-methoxy 4-glucosyl-benzoic acid)(14),4-O-β-D-gluco pyranosylbenzoate(15),tachioside(16),3',5'-dimethoxy-4-O-β-D-glucopyranosyl-cinnamic acid(17);one phenolic compound:2,3-dihydroxy-1-(4-hydroxy-3, 5-dimethoxyphenyl)-1-propanone(18);one flavnoid glucoside:acacetin 7-rutinoside (19);and glucose(20),sucrose(21),stearic acid(22),glyceryl monosterate(23),β-sitosterol(24).Among them,compounds 1,2 are new lignan glucosides,4,5 are new indole alkaloid glucosides,7,10 are new phenolic glucosides,and eleven known compounds 3,8,9,11-18 were isolated from this family for the first time,and flavnoid glucoside 19 was isolated from this genus for the first time.
Twenty-five compounds were obtained and identified from 95%alcohol extracts (n-BuOH and EtOAc extracts) of the leaves of Neoalsomitra integrifoliola.They are one sesquiterpene glycoside:(6R,9R)-blumenylα-L-rhamnopyranosyl-(1→6)-β-D-glupyranoside (1);five lignan glycosides:8,8'-E-7',8'-E-5,5'-dimethoxy-7-oxolariciresinol-9'-O-β-D-xylopyranoside(2),(7S,8R)-dihydrodehydrodiconiferyl alcohol-9'-O-β-D-apiofuranosyl-(1→6)-O-β-D-gluco pyranoside(3),dihydrodehydro diconiferyl alcohol 9'-O-β-D-glucopyranosides(4),nudiposide(5),9-O-β-D-xylopyranoside of icariol A_2 and its epimer 9-O-β-D-xylopyranoside of 8,8'-E-icariol A_2(6);a pair of lignan compounds:icariol A_2 and its epimer 8,8'-E-icariol A_2(7);one phenolic glycoside:2-methoxy-4-trans-propenyl-phenol α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(8);three flavnoid glycosides: rutin(9),kaempferol-3-O-α-L-rhamnopyranosyl(1→6)β-D-glucopyranoside(10), isorhamnetin-3-O-α-L-rhamnopyranosyl(1→6)β-D-glucopyranoside(11);two sterol compounds:α-spinasterol(12),α-spinasterol 3-O-β-D-glucopyranoside(13);three aromatic acid:3,4-dihydroxybenzoix acid(14),4-hydroxybenzoix acid(15),gallic acid(16);and methyl chlorogenate(17),2-phenylethyl rutinoside(18),epifriedelanol (19),asteruacerebrosided(20),saikoceramide(21),guanosine(22),adenosine(23), myo-inositol(24),stearic acid(25).Among them,compounds 1 is a new sesquiterpene glycoside,2,3 are new lignan glycosides,8 is a new nature product;and all twenty-one known compounds were isolated from this genus for the first time.
The results of bioassays in vitro displayed:(1) Obtained from 95%alcohol extracts of the roots of Capparis tenera,four compounds 4,10,13,17 showed marginal antioxidation activity,with the inhibitory rates of the liver microsomal lipid peroxidation induced by Fe~(2+)-Cys system from 12.0%to 19.0%respectively at concentration of 1×10~(-6) mol/L;six compounds 5,7,9,11,17,19 showed low-level anti-inflammation activity,with the inhibitory rates of release ofβ-glucuronidase from rat PMNs induced by PAF from 13.2%to 18.8%respectively at concentration of 1×10~(-5) mol/L;nine compounds(4,5,6,7,8,9,11,13,17) showed no cytotoxic.(2) Obtained from 95%alcohol extract of the roots of Neoalsomitra integrifoliola,four compounds showed marginal antioxidation activity,with the inhibitory rates of the liver microsomal lipid peroxidation induced by Fe~(2+)-Cys system from 11.1%to 19.0 %respectively at concentration of 1×10~(-6) mol/L;five compounds(1,5,11,12,14) showed low-level anti-inflammation activity,with the inhibitory rates of release ofβ-glucuronidase from rat PMNs induced by PAF from 16.7%to 25.0%respectively at concentration of 1×10~(-5)mol/L;three compounds(14,16,19) exhibited moderate cytotoxicity against five tumor cell lines(A549,Bel-7402,BGC-823,HCT-8,and MCF-7,1μg/ml＜IC_(50)＜10μg/ml).
苦藤(Neoalsomitra integrifoliola(Cogn.)Hutch.)是葫芦科(Cucurbitaceae)翅子瓜亚族(subtrib.Zanoninae)棒槌瓜属(Neoalsomitra)的一种有毒植物。该属植物多为攀援灌木或草质藤本,全世界共约12种,我国有2种,分别为棒槌瓜(苦藤)和藏棒槌瓜,产华南、西南和台湾。据报道苦藤的茎、叶和果实有毒,能引起剧烈腹泻,严重时手足抽搐。本所药理室筛选结果表明苦藤(叶)95%乙醇总提取物、乙酸乙酯部位和正丁醇部位都显示明显的抗炎活性和细胞毒活性。
为从天然产物中寻找生物活性成分,本论文运用多种色谱方法和波谱技术,在生物活性指导下,对上述2种有毒植物进行了系统的化学成分研究。从2种植物中共分离得到56个化合物,鉴定了49个化合物的结构,其中9个为新化合物。这9个新化合物分属于4种结构类型,包括4个新的木脂素苷类化合物(从薄叶山柑分离得到的化合物1,2,从苦藤分离得到的化合物2,3);2个新的生物碱苷类化合物(从薄叶山柑分离得到的化合物4,5);2个新的酚苷类化合物(从薄叶山柑分离得到的化合物7,10);和1个新的倍半萜苷类化合物(从苦藤分离得到的化合物1)。40个已知化合物,分属于9种结构类型。包括4个已知的木脂素苷类化合物,1个已知的木脂素类化合物,1个已知的生物碱苷类化合物,10个已知的酚苷类化合物,1个已知的酚类化合物,4个已知的黄酮苷类化合物,2个甾醇类化合物,3个芳香酸以及14个其它类化合物。
从薄叶山柑Capparis tenera Dalz.(Capparidaceae)(根)95%乙醇提取物的正丁醇及石油醚萃取部位中共分离鉴定了24个化合物,分别为:3个木脂素苷类化合物:(+)-lyoniresin-4'-ylβ-glucopyranoside(1),(-)-8'-epi-lyoniresin-4-ylβ-glucopyranoside(2),(+)-lyoniresin-4-ylβ-D-glucopyranoside(3);3个生物碱苷类化合物:1H-indole-3-acetamideβ-glucopyranoside(4),1H-indole-3-carbaldehydeβ-glucopyranoside(5),cappariloside A(6);11个酚苷类化合物:1-(2,6-dimethoxy-benzoic acid)-6-O-syringoyl-β-glucopyranoside(7),clemochinenosideA(8),clemochinenoside B(9),2,6-dimethoxy-p-hydroquinone1-O-β-6-O-(3-hydroxy-3-methylglutaryl)glucopyranoside(10),2,6-dimethoxy-phydroquinone1-O-β-D-glucopyranoside(11),erigeside C(12),glucosuringic acid(13),vanillic acid 4-O-β-D-glucoside(3-methoxy 4-glucosyl-benzoic acid)(14),4-O-β-D-glucopyranosylbenzoate(15),tachioside(16),3',5'-dimethoxy-4-O-β-D-glucopyranosyl-cinnamic acid(17);1个酚类化合物:2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(18);1个黄酮苷类化合物:金合欢素7-O-芸香糖苷(19);以及葡萄糖(20),蔗糖(21),硬脂酸(22),甘油单十八烷酸酯(23),β-谷甾醇(24)。化合物1,2为木脂素苷类新化合物,化合物4,5为生物碱苷类新化合物,化合物7,8为酚苷类新化合物。在得到的已知化合物中,有11个化合物为首次从白花菜科得到,分别为化合物3,8,9,11-18;黄酮苷类化合物19为首次从该属分离得到。
从苦藤Neoalso mitra integrifoliola(Cogn.)Hutch.(cucurbitaceae)(叶)95%乙醇提取物的正丁醇及乙酸乙酯萃取部位中共分离鉴定了25个化合物,分别为:1个倍半萜苷类化合物:(6R,9R)-blumenylα-L-rhamnopyranosyl-(1→6)-β-D-glupyranoside(1);5个木脂素苷类化合物:8,8'-E-7',8'-E-5,5'-dimethoxy-7-oxolariciresinol-9'-O-β-D-xylopyranoside(2),(7S,8R)-二氢化脱氢松柏醇9'-O-β-D-芹糖-(1→6)-O-β-D-葡萄糖苷(3),二氢化脱氢松柏醇9'-O-β-D-葡萄糖苷(4),nudiposide(5),9-O-β-D-xylopyranoside of icariol A_2和其差向异构体9-O-β-D-xylopyranoside of 8,8'-E-icariol A_2(6);1对木脂素类化合物:icariol A_2和其差向异构体8,8'-E-icariol A_2(7);1个酚苷类化合物:2-methoxy-4-trans-propenyl-phenolα-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(8);3个黄酮苷类化合物:芦丁(9),山柰酚-3-O-(6"-O-α-L-鼠李吡喃糖基)-β-D-葡萄吡喃糖苷(10),异鼠李素-3-O-(6"-O-α-L-鼠李吡喃糖基)-β-D-葡萄吡喃糖苷(11);2个甾醇及其苷类化合物:α-菠甾醇(12),α-菠甾醇3-O-β-D-葡萄吡喃糖苷(13);3个芳香酸:3,4-二羟基苯甲酸(14),4-羟基苯甲酸(15),没食子酸(16);以及绿原酸甲酯(17),2-苯基乙醇芸香糖苷(18),表木栓醇(19),asteruacerebrosided(20),柴胡神经酰胺(21),鸟苷(22),腺苷(23),肌-肌醇(24),硬脂酸(25)。化合物1为倍半萜苷类新化合物,化合物2,3为木脂素苷类新化合物,化合物8为酚苷类新天然产物。所得21个已知化合物均为从该属首次分离得到。
体外药理模型筛选结果表明:(1)薄叶山柑(根)95%乙醇提取物正丁醇部位4个化合物4,10,13,17有极弱的抗氧化活性,在浓度为1×10~(-6)mol/L时,抑制Fe~(2+)半胱氨酸诱导的肝微粒体脂质过氧化物产生率为12.0-19.0%;共6个化合物5,7,9,11,17,19有弱的抗炎活性,在浓度为1×10~(-5) mol/L时,抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放率为13.2-18.8%;共9个化合物4,5,6,7,8,9,11,13,17无细胞毒活性(IC_(50)＞50μg/ml)。(2)苦藤(叶)95%乙醇提取物正丁醇部位6个化合物1,12,14,20,21,23有极弱的抗氧化活性,在浓度为1×10~(-6)mol/L时,抑制Fe~(2+)半胱氨酸诱导的肝微粒体脂质过氧化物产生率为11.1-19.0%;共5个化合物1,5,11,12,14有弱的抗炎活性,在浓度为1×10~(-5) mol/L时,抑制PAF刺激的多形核白细胞β-葡萄糖苷酸酶释放率为16.7-25.0%;共3个化合物14,16,19,对A549(人肺腺癌细胞),Bel-7402(人肝癌细胞),BGC-823(人胃癌细胞),HCT-8(人结肠癌细胞),MCF-7(人乳腺癌细胞)细胞有中等的细胞毒活性(1μg/ml＜IC_(50)＜10μg/ml)。
Capparis tenera Dalz.is a toxic species of genus Capparis,which is one of the the main toxic genuses of family Capparidaceae.Capparis comprises about 250-400 species,most of them are bushes or arbores.About 32 species are distributed from southwest to Taiwan in China,excluding one in Xinjiang and west of Xizang respectively.It was reported that the chloroform extracts of its stem bark showed neural toxicity.However,no chemical investigations of this plant had been reported by now.The results of bioassay displayed that the crude extracts of 95%alcohol, petroleum ether,deposition of petroleum ether,ethyl acetate,and n-butanol showed good antioxidant activities。
Neoalsomitra integrifoliola(Cogn.) Hutch.is a toxic species of genus Neoalsomitra of subtrib.Zanoninae of cucurbitaceae.The genus Neoalsomitra comprises about 12 species,most of them are rosebush or herbaceous vine.Two species of them,N.integrifoliola and N.clavigera distributed in south,southwest and Taiwan in China.It was reported that the stems,leaves and fruits of N.integrifoliola are toxic and the toxin can cause severe diarrhea,and even tetany.The results of bioassay displayed that 95%alcohol crude extracts of leaves of Neoalsomitra integrifoliola,and fractions of ethyl acetate,n-butanol showed obvious anti-inflammatory activity and cytotoxity.
In order to find bioactive compounds from natural products,we studied systematically on chemical constituents of the two toxic plants mentioned above with guidance of bioactivities screening.Based on various chromatographic methods and spectral technologies,56 compounds were obtained from the two plants,among which 49 compounds were identified,including 9 new compounds.These new compounds belong to four structures:4 new lignan glycosides(compounds 1,2 obtained from C. tenera,compounds 2,3 obtained from N.integrifoliola);2 new alkaloid glycosides (compounds 4,5 obtained from C.tenera);2 new phenolic glycosides(compounds 7, 10 obtained from C.tenera);1 new sesquiterpene glycoside(compounds 1 obtained from N.integrifoliola).40 known compounds belong to nine structures:4 known lignan glycosides;1 known lignan compound;1 known alkaloid glycosides;10 known phenolic glycosides;1 known phenolic compound;4 known flavnoid glycosides;2 known sterol compounds;3 aromatic acid compounds;and 14 other compounds。
Twenty-four compounds were obtained and identified from 95%alcohol extracts (n-BuOH and petroleum ether extracts) of the roots of Capparis tenera.They are three lignan glucosides:(+)-lyoniresin-4'-ylβ-glucopyranoside(1), (-)-8'-epi-lyoniresin-4-ylβ-glucopyranoside(2),(+)-lyoniresin-4-ylβ-D-glucopyranoside(3);three indole alkaloid glucosides:1H-indole-3-acetamideβ-glucopyranoside(4),1H-indole-3-carbaldehydeβ-glucopyranoside(5), cappariloside A(6);eleven phenolic glucosides:1-(2,6-dimethoxy-benzoic acid)-6-O-syringoyl-β-glucopyranoside(7),clemochinenoside A(8), clemochinenoside B(9),2,6-dimethoxy-p-hydroquinone 1-O-β-6-O-(3-hydroxy-3-methylglutaryl) glucopyranoside(10),2,6-dimethoxy-p-hydroquinone 1-O-β-D-gluco pyranoside(11),erigeside C(12),glucosuringic acid(13),vanillic acid 4-O-β-D-glucoside(3-methoxy 4-glucosyl-benzoic acid)(14),4-O-β-D-gluco pyranosylbenzoate(15),tachioside(16),3',5'-dimethoxy-4-O-β-D-glucopyranosyl-cinnamic acid(17);one phenolic compound:2,3-dihydroxy-1-(4-hydroxy-3, 5-dimethoxyphenyl)-1-propanone(18);one flavnoid glucoside:acacetin 7-rutinoside (19);and glucose(20),sucrose(21),stearic acid(22),glyceryl monosterate(23),β-sitosterol(24).Among them,compounds 1,2 are new lignan glucosides,4,5 are new indole alkaloid glucosides,7,10 are new phenolic glucosides,and eleven known compounds 3,8,9,11-18 were isolated from this family for the first time,and flavnoid glucoside 19 was isolated from this genus for the first time.
Twenty-five compounds were obtained and identified from 95%alcohol extracts (n-BuOH and EtOAc extracts) of the leaves of Neoalsomitra integrifoliola.They are one sesquiterpene glycoside:(6R,9R)-blumenylα-L-rhamnopyranosyl-(1→6)-β-D-glupyranoside (1);five lignan glycosides:8,8'-E-7',8'-E-5,5'-dimethoxy-7-oxolariciresinol-9'-O-β-D-xylopyranoside(2),(7S,8R)-dihydrodehydrodiconiferyl alcohol-9'-O-β-D-apiofuranosyl-(1→6)-O-β-D-gluco pyranoside(3),dihydrodehydro diconiferyl alcohol 9'-O-β-D-glucopyranosides(4),nudiposide(5),9-O-β-D-xylopyranoside of icariol A_2 and its epimer 9-O-β-D-xylopyranoside of 8,8'-E-icariol A_2(6);a pair of lignan compounds:icariol A_2 and its epimer 8,8'-E-icariol A_2(7);one phenolic glycoside:2-methoxy-4-trans-propenyl-phenol α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside(8);three flavnoid glycosides: rutin(9),kaempferol-3-O-α-L-rhamnopyranosyl(1→6)β-D-glucopyranoside(10), isorhamnetin-3-O-α-L-rhamnopyranosyl(1→6)β-D-glucopyranoside(11);two sterol compounds:α-spinasterol(12),α-spinasterol 3-O-β-D-glucopyranoside(13);three aromatic acid:3,4-dihydroxybenzoix acid(14),4-hydroxybenzoix acid(15),gallic acid(16);and methyl chlorogenate(17),2-phenylethyl rutinoside(18),epifriedelanol (19),asteruacerebrosided(20),saikoceramide(21),guanosine(22),adenosine(23), myo-inositol(24),stearic acid(25).Among them,compounds 1 is a new sesquiterpene glycoside,2,3 are new lignan glycosides,8 is a new nature product;and all twenty-one known compounds were isolated from this genus for the first time.
The results of bioassays in vitro displayed:(1) Obtained from 95%alcohol extracts of the roots of Capparis tenera,four compounds 4,10,13,17 showed marginal antioxidation activity,with the inhibitory rates of the liver microsomal lipid peroxidation induced by Fe~(2+)-Cys system from 12.0%to 19.0%respectively at concentration of 1×10~(-6) mol/L;six compounds 5,7,9,11,17,19 showed low-level anti-inflammation activity,with the inhibitory rates of release ofβ-glucuronidase from rat PMNs induced by PAF from 13.2%to 18.8%respectively at concentration of 1×10~(-5) mol/L;nine compounds(4,5,6,7,8,9,11,13,17) showed no cytotoxic.(2) Obtained from 95%alcohol extract of the roots of Neoalsomitra integrifoliola,four compounds showed marginal antioxidation activity,with the inhibitory rates of the liver microsomal lipid peroxidation induced by Fe~(2+)-Cys system from 11.1%to 19.0 %respectively at concentration of 1×10~(-6) mol/L;five compounds(1,5,11,12,14) showed low-level anti-inflammation activity,with the inhibitory rates of release ofβ-glucuronidase from rat PMNs induced by PAF from 16.7%to 25.0%respectively at concentration of 1×10~(-5)mol/L;three compounds(14,16,19) exhibited moderate cytotoxicity against five tumor cell lines(A549,Bel-7402,BGC-823,HCT-8,and MCF-7,1μg/ml＜IC_(50)＜10μg/ml).
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