黔产白刺花、红叶木姜子、滇木姜子化学成分及生物活性研究
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摘要
本论文报道三种黔产植物,白刺花、红叶木姜子、滇木姜子的化学成分及其对植物病原菌的抑菌活性研究。利用多种层析手段进行分离和纯化,通过理化方法及光谱分析鉴定各化合物的结构。采用KB纸片法对粗提物及所分到的单体化合物进行植物病原菌初步抑菌活性筛选。从三种植物中共分离得到86个化合物,鉴定了其中的79个化合物。除BCH-4、BCH-10、BCH-11、BCH-12、BCH-13、BCH-14、BCHG-4、BCHG-7、BCHG-8、BCHG-15、BCHG-16外,其余化合物均首次从该三种植物中分离得到。化合物主要类型涉及生物碱类、黄酮类、香豆素类、蒽醌类、三萜和甾体类、脂肪酸类等。生物活性筛选表明有11个化合物对植物病原真菌有抑制活性,活性成分主要为生物碱、黄酮、苯醌及蒽醌类化合物。白刺花生物总碱、红叶木姜子生物总碱和滇木姜子生物总碱对乙酰胆碱酯酶有一定的抑制作用。
从白刺花种子的乙酸乙酯和正丁醇部分共分离得到15个化合物,鉴定了其中14个化合物。分别是β-谷甾醇(BCH-1)、高丽槐素(BCH-2)、7-羟基-3′,4′-亚甲基二氧异黄酮(BCH-3)、7,3′,4′-三羟基黄酮(BCH-4)、7,3′-二羟基-4′-甲氧基黄酮(BCH-5)、香叶木素(BCH-6)、毛蕊异黄酮(BCH-7)、红车轴草苷(BCH-8)、胡萝卜苷(BCH-9)、槐果碱(BCH-10)、苦参碱(BCH-11)、槐定碱(BCH-12)、氧化槐果碱(BCH-13)、氧化苦参碱(BCH-14)。除BCH-4、BCH-10、BCH-11、BCH-12、BCH-13、BCH-14外,其余化合物均首次从该植物中分离得到。从白刺花根茎的乙酸乙酯和正丁醇部分共分离得到20个化合物,鉴定了其中18个化合物。分别是正二十九烷醇(BCHG-1)、正三十烷醇(BCHG-2)、正二十六烷酸(BCHG-3)、β-谷甾醇(BCHG-4)、正三十烷酸(BCHG-5)、棕榈酸单甘酯(BCHG-6)、高丽槐素(BCHG-7)、7-羟基-3′,4′-亚甲基二氧异黄酮(BCHG-8)、正三十二烷酸(BCHG-9)、白藜芦醇(BCHG-10)、二十六烷酸甘油酯(BCHG-11)、伞形花内酯(BCHG-12)、赫尼亚林(BCHG-13)、东莨菪内酯(BCHG-14)、胡萝卜苷(BCHG-15)、红车轴草苷(BCHG-16)、皮契荔枝苷(BCHG-17)、蔗糖(BCHG-18)。除BCHG-4、BCHG-7、BCHG-8、BCHG-15、BCHG-16外,其余化合物均首次从该植物中分离得到。采用KB纸片法对白刺花粗提物及分离出的单体化合物进行初步抑菌活性筛选,结果表明白刺花种子醇提物对西瓜炭疽病菌(Colletotrichumorbiculare)、烟炭疽病菌(Colletotrichum micotianae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,乙酸乙酯萃取物对紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruansolanif)有抑制活性,正丁醇萃取物对绿色木霉(Trichoderma vride)、西瓜炭疽病菌(Colletotrichum orbiculare)和烟炭疽病菌(Colletotrichum micotianae)有抑制活性,白刺花根茎醇提物和乙酸乙酯萃取物对紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,正丁醇萃取物对绿色木霉(Trichoderma vride)有抑制活性,白刺花生物总碱对西瓜炭疽病菌(Colletotrichum orbiculare)、烟炭疽病菌(Colletotrichum micotianae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,白刺花种子正丁醇部分所分到的BCH-10、BCH-11对以上三种菌株也有抑制活性,化合物BCH-2、BCH-8对绿色木霉(Trichoderma vride)和紫菜腐霉(Pythium porphyrae)有抑制活性。
从红叶木姜子乙醇提取物中共分离得到33个化合物,鉴定了其中29个化合物,分别是正二十二烷(HMY-1)、正二十烷醇(HMY-2)、正二十七烷醇(HMY-3)、对羟基苯甲醛(HMY-4)、β-谷甾醇(HMY-5)、麦角甾醇(HMY-6)、十八烷酸甘油酯(HMY-7)、香豆酸甲酯(HMY-8)、羽扇豆醇(HMY-9)、白桦脂醇(HMY-10)、白桦脂酸(HMY-11)、萨拉子酸(HMY-12)、熊果酸(HMY-13)、脱镁叶绿素甲酯(HMY-14)、大黄素(HMY-15)、大黄素甲醚(HMY-16)、正二十八烷酸(HMY-17)、阿魏酸(HMY-18)、胡萝卜苷(HMY-19)、阿魏酸二十八烷酯(HMY-20)、芹菜素(HMY-21)、木犀草素(HMY-22)、木犀草素-7-O-β-D-葡萄糖苷(HMY-23)、山萘酚(HMY-24)、槲皮素(HMY-25)、山奈酚-3-O-α-L-鼠李糖甙(HMY-26)、槲皮苷(HMY-27)、波尔定(HMY-28)、异波尔定(HMY-29)。所有化合物均首次从该植物中分离得到。此外,用水蒸气蒸馏法提取红叶木姜子鲜叶的挥发性成分,并通过气相色谱-质谱联用技术对挥发油进行了鉴定。从红叶木姜子鲜叶挥发油中共鉴定出31个化学成分,其中含量较高的组分有:w(香桧烯)=17.18%、w(1,8-桉叶素)=14.01%、w(α-蒎烯)=6.56%、w(α-松油醇)=5.71%。对红叶木姜子各粗提物及所分到的单体化合物进行初步抑菌活性筛选,发现红叶木姜子鲜叶挥发油对紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,红叶木姜子醇提物对绿色木霉(Trichoderma vride)和紫菜腐霉(Pythium porphyrae)有抑制活性,乙酸乙酯萃取物对茄病镰刀菌(Fusaruan solanif)有抑制活性,红叶木姜子水部分和生物总碱都对小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性,化合物HMY-15对绿色木霉(Trichoderma vride)和茄病镰刀菌(Fusaruan solanif)有抑制活性,HMY-16对绿色木霉(Trichoderma vride)有抑制活性,HMY-25和HMY-27对绿色木霉(Trichoderma vride)和小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性,HMY-28对小麦全蚀病菌Gaeumannomyces graminis)有抑制活性。
从滇木姜子乙醇提取物中共分离得到20个化合物,鉴定了其中18个化合物,分别是16-三十一烷酮(DMY-1)、正二十五烷醇(DMY-2)、正二十四烷酸(DMY-3)、β-谷甾醇(DMY-4)、没食子酸(DMY-5)、β-香树酯醇(DMY-6)、菠菜甾醇(DMY-7)、2,6-二甲氧基苯醌(DMY-8)、没食子酸乙酯(DMY-9)、正二十六烷醇(DMY-10)、正三十烷酸(DMY-11)、棕榈酸单甘酯(DMY-12)、脱镁叶绿素甲酯(DMY-13)、胡萝卜苷(DMY-14)、β-香树酯醇乙酸酯(DMY-15)、山豆根黄烷酮A(DMY-16)、木犀草素-7-O-β-D-葡萄糖苷(DMY-17)、波尔定(DMY-18)。所有化合物均首次从该植物中分离得到。此外,用水蒸气蒸馏法分别提取滇木姜子鲜叶和果实挥发性成分,并通过气相色谱-质谱联用技术对挥发油进行了鉴定。从滇木姜子鲜叶挥发油中共鉴定出30个化学成分,其中含量较高的组分有:w(1,8-桉叶素)=49.59%、w(α-松油醇)=9.31%、w(桧烯)=9.01%、w(β-石竹烯)=4.03%。从滇木姜子果实挥发油中共鉴定出10个化学成分,其中含量较高的组分有:w(柠檬烯)=40.36%、w(桉油精)=18.11%。采用KB纸片法对滇木姜子粗提物及所分到的单体化合物进行初步抑菌活性筛选,结果表明滇木姜子鲜叶挥发油和果实挥发油都对绿色木霉(Trichoderma vride)和紫菜腐霉(Pythium porphyrae)有抑制活性,此外,果实挥发油还对茄病镰刀菌(Fusaruan solanif)和小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性,滇木姜子醇提物对绿色木霉(Trichodermavride)和紫菜腐霉(Pythium porphyrae)有抑制活性,乙酸乙酯萃取物对绿色木霉(Trichoderma vride)有抑制活性,滇木姜子水部分对小麦全蚀病菌(Gaeumannomycesgraminis)有抑制活性,滇木姜子生物总碱对茄病镰刀菌(Fusaruan solanif)有抑制活性,化合物DMY-8对绿色木霉(Trichoderma vride)、紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,DMY-16和DMY-18对小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性。
This thesis reports the studies on chemical constituents and antifungal activities of three medicainal plants Sophora davidii(Franch.) Kom.ex Pavol.,Litsea rubescens Lee. var.rubescens and Litsea rubescens Lec.var.yunnanesis,distributed in Guizhou province. The constituents were isolated by chromatographic methods,and their structures were elucidated by physicochemical and spectroscopic data,and their antifungal activities against phytopathogens were evaluated by the KB disk diffusion test.86 compounds were isolated from three chinese traditional herb drugs,out of which 79 compounds were identified from these plants for the first time except for compound BCH-4,BCH-10, BCH-11,BCH-12,BCH-13,BCH-14,BCHG-4,BCHG-7,BCHG-8,BCHG-15 and BCHG-16.The compounds resembled with typical alkaloid,flavone,coumarin, anthraquinone,triterpene,steroid and fatty acid structures.11 compounds belonging to alkaloids,flavonoids,benzoquinone and anthraquinone displayed antifungal activities. Total alkaoids from the Sophora davidii(Franch.) Kom.ex Pavol.,Litsea rubescens Lec. var.rubescens and Litsea rubescens Lec.var.rubescens could inhibit acetylcholi-nesterase. 101391 15 compounds were isolated from the seeds of Sophora davidii(Franch.) Kom.ex Pavol.,in which 14 compounds were identified asβ-sitosterol(BCH-1),maackiain (BCH-2),7-hydroxy-3′,4′-methylenedioxyisoflavone(BCH-3),7,3′,4′-trihydroxyflavone (BCH-4),7,3′-dihydroxy-4′-methoxfiavone(BCH-5),diosmetin(BCH-6),calycosin (BCH-7),trifolirhizin(BCH-8),daucosterol(BCH-9),sophocarpine(BCH-10),matrine (BCH-11),sophoridine(BCH-12),oxysophocarpine(BCH-13) and oxymatrine(BCH-14). Besides compound BCH-4,BCH-10,BCH-11,BCH-12,BCH-13 and BCH-14,the others were obtained from this plant for the first time.20 compounds were isolated from the roots and stems of Sophora davidii,in which 18 compounds were identified as nonacosan-1-o1 (BCHG-1),tfiacontanol(BCHG-2),hexacosanoic acid(BCHG-3),β-sitosterol(BCHG-4), triacontanie acid(BCHG-5),1-mono-palmitin(BCHG-6),maackiain(BCHG-7),7-hydroxy -3′,4′-methylenedioxyisoflavone(BCHG-8),dotriacontanic acid(BCHG-9),resveratrol (BCHG-10),slyceryl hexacosanoate(BCHG-11),umbelliferone(BCHG-12),hemiarin (BCHG-13),scopoletin(BCHG-14),daucosterol(BCHG-15),trifolirhizin(BCHG-16), fabiatrin(BCHG-17),sucrose(BCHG-18) by spectral studies.All compound but for BCHG-4,BCHG-7,BCHG-8,BCHG-15 and BCHG-16 were obtained from this plant for the first time.The preliminary screenings on antifungal activities of the extracts and pure compounds from S.davidii were evaluated by the KB disk diffusion test.The results showed that the ethyl alcohol extraction of the seeds inhibited the development of Colletotrichum orbiculare,Colletotrichum micotianae and Fusaruan solanif.The ethyl acetate extract fraction showed antifungal activities against Pythium porphyrae and Fusaruan solanif,while butanol extraction exhibited activities against Trichoderma vride, Colletotrichum orbiculare and Colletotrichum micotianae.The ethyl alcohol extract of the stems and roots have antifungal activities against Pythium porphyrae and Fusaruan solanif, although Pythium porphyrae and Fusaruan solanif were inhibited by the ethyl acetate extract fraction.The butanol extraction showed effect against Pythium porphyrae and the total alkaoids showed inhibition effects on the growth of Colletotrichum orbiculare, Colletotrichum micotianae and Fusaruan solanif.The fact that compound BCH-10 and BCH-11 showed inhibition effects on the growth of Colletotrichum orbiculare, Colletotrichum micotianae and Fusaruan solanif,BCH-2 and BCH-8,control of the growth of Trichoderma vride and Pythium porphyrae was understanden.
33 compounds were isolated from Litsea rubescens Lec.var.rubescens,in which 29 compound.s were identified as docosane(HMY-1),eicosanol(HMY-2),heptacosanol (HMY-3),p-hydroxybenzacdehyde(HMY-4),β-sitosterol(HMY-5),erogosterol(HMY-6), glycerol-1-alkanoates(HMY-7),methyl p-coumarate(HMY-8),lupeol(HMY-9),betulin (HMY-10),betulinic acid(HMY-11),salaspermic acid(HMY-12),ursolic acid(HMY-13), methyl phaeophorbidea,3″-meester(HMY-14),emodin(HMY-15),physcion(HMY-16), n-octacosanoic acid(HMY-17),ferulic acid(HMY-18),daucosterol(HMY-19), octacosanyl ferucate(HMY-20),apigenin(HMY-21),luteolin(HMY-22),luteolin-7-O-β-D -glucopyranoside(HMY-23),kaempferol(HMY-24),quercetin(HMY-25),kaempferol-3-O -α-L-rhamnoside(HMY-26),quercitrin(HMY-27),boldine(HMY-28) and isoboldine (HMY-29).All of them were obtained from this plant for the first time.The leaves essential oil of L.rubescens was obtained by the method of hydrodistillation,and its chemical constituents were determined by analyses of GC/MS spectral data.31 components were checked out from the essential oil,in which the major compounds eudesm-11-en-4-ol (11.5%),myrcene(11.3%),β-caryophyllene(8.4%),α-phellandrene(7.1%) were cleared. The preliminary screening on antifungal activities of the extracts and compounds from L. rubescens were evaluated by the KB disk diffusion test.The results indicated that the essential oil of L.rubescens can inhibit the growth of Pythium porphyraeand Fusaruan solanif.The ethyl alcohol extraction had effect on Trichoderma vride and Pythium porphyrae.The ethyl acetate extraction can control the development of Fusaruan solanif Gaeumannomyces graminis was inhibited by water extraction and total alkaoids. Compound HMY-15 showed inhibitory effect on Trichoderma vride and Fusaruan solanif. The HMY-16 can control the growth of Trichoderma vride.The HMY-25 and HMY-27 were found effective against Trichoderma vride and Gaeumannomyces graminis.The HMY-28 had antifungal activities against Gaeumannomyces graminis.
20 compounds were isolated from Litsea rubescens Lec.var.yunnanesis,in which 18 compounds were identified as 16-hentriacontanone(DMY-1),pentacosanol(DMY-2), isoselachoceric acid(DMY-3),β-sitosterol(DMY-4),gallic acid(DMY-5),β-amyrin (DMY-6),chondrillasterol(DMY-7),2,6-dimethoxybenzoquinone(DMY-8),ethylgallate (DMY-9),hexxacosanol(DMY-10),triacontanoic acid(DMY-11),1-mono-palmitin (DMY-12),methyl phaeophorbidea,3″-meester(DMY-13),daucosterol(DMY-14),β-amyrin acetate(DMY-15),euchrestaflavanone A(DMY-16),luteolin-7-O-β-D-glucopy-ranoside (DMY-17) and boldine(DMY-18).All of them were obtained from this plant for the first time.The oils of this species,obtained by hydrodistillation from the fresh fruits and leaves,were examined by GC/MS.30 components were analysized in the oils from leaves and 10 components from fruits.The leaves oil was mainly composed ofβ-pinene,β-myrcene,1,8-cineole,L-linalool,terpinen-4-ol and a-terpineol.The major components of the fruits oil were limonenem and eucalyptol.The preliminary evaluations on antifungal activities of the extracts and compounds from L.rubescens were developped by the KB disk diffusion test.The results showed that the volatile oil from fruits exhibited activities against Trichoderma vride,Pythium porphyrae,Fusaruan solanif and Gaeumannomyces graminis,the leaves oils and ethyl alcohol extraction against Trichoderma vride and Pythium porphyrae.The ethyl acetate extraction can control the development of Trichoderma vride.The total alkaoids can inhibit the growth of Fusaruan solanif,while water extraction was effective against Gaeumannomyces graminis.Compound DMY-8 showed inhibition effects on the growth of Trichoderma vride,Pythium porphyrae and Fusaruan solanif.The DMY-16 and DMY-18 had antifungal activities against Gaeumannomyces graminis.
从白刺花种子的乙酸乙酯和正丁醇部分共分离得到15个化合物,鉴定了其中14个化合物。分别是β-谷甾醇(BCH-1)、高丽槐素(BCH-2)、7-羟基-3′,4′-亚甲基二氧异黄酮(BCH-3)、7,3′,4′-三羟基黄酮(BCH-4)、7,3′-二羟基-4′-甲氧基黄酮(BCH-5)、香叶木素(BCH-6)、毛蕊异黄酮(BCH-7)、红车轴草苷(BCH-8)、胡萝卜苷(BCH-9)、槐果碱(BCH-10)、苦参碱(BCH-11)、槐定碱(BCH-12)、氧化槐果碱(BCH-13)、氧化苦参碱(BCH-14)。除BCH-4、BCH-10、BCH-11、BCH-12、BCH-13、BCH-14外,其余化合物均首次从该植物中分离得到。从白刺花根茎的乙酸乙酯和正丁醇部分共分离得到20个化合物,鉴定了其中18个化合物。分别是正二十九烷醇(BCHG-1)、正三十烷醇(BCHG-2)、正二十六烷酸(BCHG-3)、β-谷甾醇(BCHG-4)、正三十烷酸(BCHG-5)、棕榈酸单甘酯(BCHG-6)、高丽槐素(BCHG-7)、7-羟基-3′,4′-亚甲基二氧异黄酮(BCHG-8)、正三十二烷酸(BCHG-9)、白藜芦醇(BCHG-10)、二十六烷酸甘油酯(BCHG-11)、伞形花内酯(BCHG-12)、赫尼亚林(BCHG-13)、东莨菪内酯(BCHG-14)、胡萝卜苷(BCHG-15)、红车轴草苷(BCHG-16)、皮契荔枝苷(BCHG-17)、蔗糖(BCHG-18)。除BCHG-4、BCHG-7、BCHG-8、BCHG-15、BCHG-16外,其余化合物均首次从该植物中分离得到。采用KB纸片法对白刺花粗提物及分离出的单体化合物进行初步抑菌活性筛选,结果表明白刺花种子醇提物对西瓜炭疽病菌(Colletotrichumorbiculare)、烟炭疽病菌(Colletotrichum micotianae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,乙酸乙酯萃取物对紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruansolanif)有抑制活性,正丁醇萃取物对绿色木霉(Trichoderma vride)、西瓜炭疽病菌(Colletotrichum orbiculare)和烟炭疽病菌(Colletotrichum micotianae)有抑制活性,白刺花根茎醇提物和乙酸乙酯萃取物对紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,正丁醇萃取物对绿色木霉(Trichoderma vride)有抑制活性,白刺花生物总碱对西瓜炭疽病菌(Colletotrichum orbiculare)、烟炭疽病菌(Colletotrichum micotianae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,白刺花种子正丁醇部分所分到的BCH-10、BCH-11对以上三种菌株也有抑制活性,化合物BCH-2、BCH-8对绿色木霉(Trichoderma vride)和紫菜腐霉(Pythium porphyrae)有抑制活性。
从红叶木姜子乙醇提取物中共分离得到33个化合物,鉴定了其中29个化合物,分别是正二十二烷(HMY-1)、正二十烷醇(HMY-2)、正二十七烷醇(HMY-3)、对羟基苯甲醛(HMY-4)、β-谷甾醇(HMY-5)、麦角甾醇(HMY-6)、十八烷酸甘油酯(HMY-7)、香豆酸甲酯(HMY-8)、羽扇豆醇(HMY-9)、白桦脂醇(HMY-10)、白桦脂酸(HMY-11)、萨拉子酸(HMY-12)、熊果酸(HMY-13)、脱镁叶绿素甲酯(HMY-14)、大黄素(HMY-15)、大黄素甲醚(HMY-16)、正二十八烷酸(HMY-17)、阿魏酸(HMY-18)、胡萝卜苷(HMY-19)、阿魏酸二十八烷酯(HMY-20)、芹菜素(HMY-21)、木犀草素(HMY-22)、木犀草素-7-O-β-D-葡萄糖苷(HMY-23)、山萘酚(HMY-24)、槲皮素(HMY-25)、山奈酚-3-O-α-L-鼠李糖甙(HMY-26)、槲皮苷(HMY-27)、波尔定(HMY-28)、异波尔定(HMY-29)。所有化合物均首次从该植物中分离得到。此外,用水蒸气蒸馏法提取红叶木姜子鲜叶的挥发性成分,并通过气相色谱-质谱联用技术对挥发油进行了鉴定。从红叶木姜子鲜叶挥发油中共鉴定出31个化学成分,其中含量较高的组分有:w(香桧烯)=17.18%、w(1,8-桉叶素)=14.01%、w(α-蒎烯)=6.56%、w(α-松油醇)=5.71%。对红叶木姜子各粗提物及所分到的单体化合物进行初步抑菌活性筛选,发现红叶木姜子鲜叶挥发油对紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,红叶木姜子醇提物对绿色木霉(Trichoderma vride)和紫菜腐霉(Pythium porphyrae)有抑制活性,乙酸乙酯萃取物对茄病镰刀菌(Fusaruan solanif)有抑制活性,红叶木姜子水部分和生物总碱都对小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性,化合物HMY-15对绿色木霉(Trichoderma vride)和茄病镰刀菌(Fusaruan solanif)有抑制活性,HMY-16对绿色木霉(Trichoderma vride)有抑制活性,HMY-25和HMY-27对绿色木霉(Trichoderma vride)和小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性,HMY-28对小麦全蚀病菌Gaeumannomyces graminis)有抑制活性。
从滇木姜子乙醇提取物中共分离得到20个化合物,鉴定了其中18个化合物,分别是16-三十一烷酮(DMY-1)、正二十五烷醇(DMY-2)、正二十四烷酸(DMY-3)、β-谷甾醇(DMY-4)、没食子酸(DMY-5)、β-香树酯醇(DMY-6)、菠菜甾醇(DMY-7)、2,6-二甲氧基苯醌(DMY-8)、没食子酸乙酯(DMY-9)、正二十六烷醇(DMY-10)、正三十烷酸(DMY-11)、棕榈酸单甘酯(DMY-12)、脱镁叶绿素甲酯(DMY-13)、胡萝卜苷(DMY-14)、β-香树酯醇乙酸酯(DMY-15)、山豆根黄烷酮A(DMY-16)、木犀草素-7-O-β-D-葡萄糖苷(DMY-17)、波尔定(DMY-18)。所有化合物均首次从该植物中分离得到。此外,用水蒸气蒸馏法分别提取滇木姜子鲜叶和果实挥发性成分,并通过气相色谱-质谱联用技术对挥发油进行了鉴定。从滇木姜子鲜叶挥发油中共鉴定出30个化学成分,其中含量较高的组分有:w(1,8-桉叶素)=49.59%、w(α-松油醇)=9.31%、w(桧烯)=9.01%、w(β-石竹烯)=4.03%。从滇木姜子果实挥发油中共鉴定出10个化学成分,其中含量较高的组分有:w(柠檬烯)=40.36%、w(桉油精)=18.11%。采用KB纸片法对滇木姜子粗提物及所分到的单体化合物进行初步抑菌活性筛选,结果表明滇木姜子鲜叶挥发油和果实挥发油都对绿色木霉(Trichoderma vride)和紫菜腐霉(Pythium porphyrae)有抑制活性,此外,果实挥发油还对茄病镰刀菌(Fusaruan solanif)和小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性,滇木姜子醇提物对绿色木霉(Trichodermavride)和紫菜腐霉(Pythium porphyrae)有抑制活性,乙酸乙酯萃取物对绿色木霉(Trichoderma vride)有抑制活性,滇木姜子水部分对小麦全蚀病菌(Gaeumannomycesgraminis)有抑制活性,滇木姜子生物总碱对茄病镰刀菌(Fusaruan solanif)有抑制活性,化合物DMY-8对绿色木霉(Trichoderma vride)、紫菜腐霉(Pythium porphyrae)和茄病镰刀菌(Fusaruan solanif)有抑制活性,DMY-16和DMY-18对小麦全蚀病菌(Gaeumannomyces graminis)有抑制活性。
This thesis reports the studies on chemical constituents and antifungal activities of three medicainal plants Sophora davidii(Franch.) Kom.ex Pavol.,Litsea rubescens Lee. var.rubescens and Litsea rubescens Lec.var.yunnanesis,distributed in Guizhou province. The constituents were isolated by chromatographic methods,and their structures were elucidated by physicochemical and spectroscopic data,and their antifungal activities against phytopathogens were evaluated by the KB disk diffusion test.86 compounds were isolated from three chinese traditional herb drugs,out of which 79 compounds were identified from these plants for the first time except for compound BCH-4,BCH-10, BCH-11,BCH-12,BCH-13,BCH-14,BCHG-4,BCHG-7,BCHG-8,BCHG-15 and BCHG-16.The compounds resembled with typical alkaloid,flavone,coumarin, anthraquinone,triterpene,steroid and fatty acid structures.11 compounds belonging to alkaloids,flavonoids,benzoquinone and anthraquinone displayed antifungal activities. Total alkaoids from the Sophora davidii(Franch.) Kom.ex Pavol.,Litsea rubescens Lec. var.rubescens and Litsea rubescens Lec.var.rubescens could inhibit acetylcholi-nesterase. 101391 15 compounds were isolated from the seeds of Sophora davidii(Franch.) Kom.ex Pavol.,in which 14 compounds were identified asβ-sitosterol(BCH-1),maackiain (BCH-2),7-hydroxy-3′,4′-methylenedioxyisoflavone(BCH-3),7,3′,4′-trihydroxyflavone (BCH-4),7,3′-dihydroxy-4′-methoxfiavone(BCH-5),diosmetin(BCH-6),calycosin (BCH-7),trifolirhizin(BCH-8),daucosterol(BCH-9),sophocarpine(BCH-10),matrine (BCH-11),sophoridine(BCH-12),oxysophocarpine(BCH-13) and oxymatrine(BCH-14). Besides compound BCH-4,BCH-10,BCH-11,BCH-12,BCH-13 and BCH-14,the others were obtained from this plant for the first time.20 compounds were isolated from the roots and stems of Sophora davidii,in which 18 compounds were identified as nonacosan-1-o1 (BCHG-1),tfiacontanol(BCHG-2),hexacosanoic acid(BCHG-3),β-sitosterol(BCHG-4), triacontanie acid(BCHG-5),1-mono-palmitin(BCHG-6),maackiain(BCHG-7),7-hydroxy -3′,4′-methylenedioxyisoflavone(BCHG-8),dotriacontanic acid(BCHG-9),resveratrol (BCHG-10),slyceryl hexacosanoate(BCHG-11),umbelliferone(BCHG-12),hemiarin (BCHG-13),scopoletin(BCHG-14),daucosterol(BCHG-15),trifolirhizin(BCHG-16), fabiatrin(BCHG-17),sucrose(BCHG-18) by spectral studies.All compound but for BCHG-4,BCHG-7,BCHG-8,BCHG-15 and BCHG-16 were obtained from this plant for the first time.The preliminary screenings on antifungal activities of the extracts and pure compounds from S.davidii were evaluated by the KB disk diffusion test.The results showed that the ethyl alcohol extraction of the seeds inhibited the development of Colletotrichum orbiculare,Colletotrichum micotianae and Fusaruan solanif.The ethyl acetate extract fraction showed antifungal activities against Pythium porphyrae and Fusaruan solanif,while butanol extraction exhibited activities against Trichoderma vride, Colletotrichum orbiculare and Colletotrichum micotianae.The ethyl alcohol extract of the stems and roots have antifungal activities against Pythium porphyrae and Fusaruan solanif, although Pythium porphyrae and Fusaruan solanif were inhibited by the ethyl acetate extract fraction.The butanol extraction showed effect against Pythium porphyrae and the total alkaoids showed inhibition effects on the growth of Colletotrichum orbiculare, Colletotrichum micotianae and Fusaruan solanif.The fact that compound BCH-10 and BCH-11 showed inhibition effects on the growth of Colletotrichum orbiculare, Colletotrichum micotianae and Fusaruan solanif,BCH-2 and BCH-8,control of the growth of Trichoderma vride and Pythium porphyrae was understanden.
33 compounds were isolated from Litsea rubescens Lec.var.rubescens,in which 29 compound.s were identified as docosane(HMY-1),eicosanol(HMY-2),heptacosanol (HMY-3),p-hydroxybenzacdehyde(HMY-4),β-sitosterol(HMY-5),erogosterol(HMY-6), glycerol-1-alkanoates(HMY-7),methyl p-coumarate(HMY-8),lupeol(HMY-9),betulin (HMY-10),betulinic acid(HMY-11),salaspermic acid(HMY-12),ursolic acid(HMY-13), methyl phaeophorbidea,3″-meester(HMY-14),emodin(HMY-15),physcion(HMY-16), n-octacosanoic acid(HMY-17),ferulic acid(HMY-18),daucosterol(HMY-19), octacosanyl ferucate(HMY-20),apigenin(HMY-21),luteolin(HMY-22),luteolin-7-O-β-D -glucopyranoside(HMY-23),kaempferol(HMY-24),quercetin(HMY-25),kaempferol-3-O -α-L-rhamnoside(HMY-26),quercitrin(HMY-27),boldine(HMY-28) and isoboldine (HMY-29).All of them were obtained from this plant for the first time.The leaves essential oil of L.rubescens was obtained by the method of hydrodistillation,and its chemical constituents were determined by analyses of GC/MS spectral data.31 components were checked out from the essential oil,in which the major compounds eudesm-11-en-4-ol (11.5%),myrcene(11.3%),β-caryophyllene(8.4%),α-phellandrene(7.1%) were cleared. The preliminary screening on antifungal activities of the extracts and compounds from L. rubescens were evaluated by the KB disk diffusion test.The results indicated that the essential oil of L.rubescens can inhibit the growth of Pythium porphyraeand Fusaruan solanif.The ethyl alcohol extraction had effect on Trichoderma vride and Pythium porphyrae.The ethyl acetate extraction can control the development of Fusaruan solanif Gaeumannomyces graminis was inhibited by water extraction and total alkaoids. Compound HMY-15 showed inhibitory effect on Trichoderma vride and Fusaruan solanif. The HMY-16 can control the growth of Trichoderma vride.The HMY-25 and HMY-27 were found effective against Trichoderma vride and Gaeumannomyces graminis.The HMY-28 had antifungal activities against Gaeumannomyces graminis.
20 compounds were isolated from Litsea rubescens Lec.var.yunnanesis,in which 18 compounds were identified as 16-hentriacontanone(DMY-1),pentacosanol(DMY-2), isoselachoceric acid(DMY-3),β-sitosterol(DMY-4),gallic acid(DMY-5),β-amyrin (DMY-6),chondrillasterol(DMY-7),2,6-dimethoxybenzoquinone(DMY-8),ethylgallate (DMY-9),hexxacosanol(DMY-10),triacontanoic acid(DMY-11),1-mono-palmitin (DMY-12),methyl phaeophorbidea,3″-meester(DMY-13),daucosterol(DMY-14),β-amyrin acetate(DMY-15),euchrestaflavanone A(DMY-16),luteolin-7-O-β-D-glucopy-ranoside (DMY-17) and boldine(DMY-18).All of them were obtained from this plant for the first time.The oils of this species,obtained by hydrodistillation from the fresh fruits and leaves,were examined by GC/MS.30 components were analysized in the oils from leaves and 10 components from fruits.The leaves oil was mainly composed ofβ-pinene,β-myrcene,1,8-cineole,L-linalool,terpinen-4-ol and a-terpineol.The major components of the fruits oil were limonenem and eucalyptol.The preliminary evaluations on antifungal activities of the extracts and compounds from L.rubescens were developped by the KB disk diffusion test.The results showed that the volatile oil from fruits exhibited activities against Trichoderma vride,Pythium porphyrae,Fusaruan solanif and Gaeumannomyces graminis,the leaves oils and ethyl alcohol extraction against Trichoderma vride and Pythium porphyrae.The ethyl acetate extraction can control the development of Trichoderma vride.The total alkaoids can inhibit the growth of Fusaruan solanif,while water extraction was effective against Gaeumannomyces graminis.Compound DMY-8 showed inhibition effects on the growth of Trichoderma vride,Pythium porphyrae and Fusaruan solanif.The DMY-16 and DMY-18 had antifungal activities against Gaeumannomyces graminis.
引文
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