海洋细菌Bacillaceae sp.v107和真菌zp6次级代谢产物及滇南苦刺花化学成分的研究
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摘要
本论文主要分为三个部分:第一部分为海洋细菌Bacillaceae sp. v107次级代谢产物的研究。第二部分为海洋真菌zp6次级代谢产物及其抑菌活性的研究。第三部分为滇南苦刺花化学成分的研究。
综合运用薄层层析(TLC),硅胶柱层析(CC),凝胶色谱(Sephadex LH-20)、反相硅胶柱层析(ODS)和高效液相色谱(HPLC)等色谱分离方法,从海洋细菌Bacillaceae sp v107代谢产物中分离得到4个化合物,采用现代波谱技术核磁共振谱1D-NMR(~1H-NMR, 13C-NMR, DEPT)和2D-NMR (~1H-~1HCOSY, HMBC, HMQC, NOESY)波谱、质谱(EIMS, ESIMS)和红外光谱(IR)手段鉴定了它们的结构,分别为:辅酶Q10(1),β-谷甾醇(2),邻苯二甲酸二辛脂(3),十六烷酸甘油酯(4)。
从海洋真菌zp6代谢产物中分离得到14个化合物,分别为:(22E)-3β, 5α, 9α-三羟基-麦角甾-7, 22-二烯-6-酮(1),5α, 8α-环二氧-24-甲基麦角甾-6, 22-二烯-3β-醇(2),邻苯二甲酸二异丁酯(3),1, 3 ,5三甲基-尿嘧啶(4),赤藓糖醇(Erythrito) (5),4-乙酰氧基苯甲酸(6),丁二酸(7),邻苯二甲酸二辛脂(8),腺嘌呤核苷(adenosine) (9),(24R)-麦角甾-7, 22-二烯-3β, 5α, 6β-三醇(10),十八碳-9-烯酸(11),阿拉伯醇(12),4-氨基吡唑[3, 4-d]嘧啶(13),尿嘧啶核苷(14)。在对海洋真菌zp6代谢产物中分离所得到的化合物进行的抑菌活性实验中,化合物1对植物病原真菌大丽轮枝菌(Verticillium dahliae )和尖刀镰孢菌(Fusarium oxysporum)有抑菌活性;化合物10对植物病原真菌大丽轮枝菌(Verticillium dahliae ),黄瓜尖镰孢(Fusarium oxysporum f.sp.cucumarinum) ,尖刀镰孢菌(Fusarium oxysporum) ,辣椒疫霉(Phytophthora capsici )有抑菌活性。对其它化合物的抗菌活性研究,结果未显出抗菌活性。
从滇南苦刺花乙酸乙酯部分分离得到8个化合物,鉴定了其中的4个,分别为:高丽槐素(1),β-谷甾醇(2),白藜芦醇(3),正二十九醇(4)。
The thesis is divided into three parts: The first Part is the secondary metabolites of maritime bacterium Bacillaceae sp. v107. The second part is the secondary metabolites of maritime eumycete zp6 and the reseach about antibacterial activity. The third part is the research about chemical constituents of Sophora davidii.
A detailed separation and purification by using thin-layer chromatography (TLC), Sigel column chromatography (CC), gel column chromatography (Sephadex LH-20), reverse phase column chromatography (ODS) and high pressure liquid chromatography (HPLC). Four compounds were isolated from the secondary metabolites of maritime bacterium Bacillaceae sp. v107, and their structures were determined by extensive spectroscopic analysis including 1D-NMR (~1H-NMR, 13C-NMR, DEPT), 2D-NMR (~1H-~1HCOSY, HMBC, HMQC, NOESY), EIMS, ESIMS and IR. The structures of compounds were identified as following: coenzymeQ10 (1),β-sitosterol (2), Bis(2-ethylhexyl)phthalate (3), 1-O-hexadecanolenin (4).
Fourteen compounds were isolated from the secondary metabolites of maritime eumycete zp6, and their structures were identified as following: (22E)-3β, 5α, 9α-trihydroxy-ergosta-7, 22-dien-6-one(1), 5α, 8α-epidioxy-ergosta-6, 22-dien-3β-ol (2), Bis(2-methylpropyl)ester (3), 1, 3, 5-trimethyl-2, 4(~1H, 3H)-pyrimidinedione (4), Erythrito (5), 4-acetoxybenozic acid (6), succinic acid (7), Bis(2-ethylhexyl)phthalate (8), adenosine (9), (24R)-ergosta-7, 22-diene-3β, 5α, 6β-trio1 (10), 9-Octadecenoic acid (11), arabinitol (12), 4-aminopyrazolo (3, 4-d) pyrimidine (13), uridine (14).
In the experiment of antibacterial activity, compound 1 show the active in antibacterial, suppressing Verticillium dahliae and Fusarium oxysporum growth; compound 10 also show the active in antibacterial, suppressing Verticillium dahliae, Fusarium oxysporum f.sp.cucumarinum, Fusarium oxysporum and Phytophthora capsici growth.
Eight compounds were isolated from the ethylacetate-solved portion of Sophora davidii, and four compounds were identified as: maackiain (1),β-sitosterol (2), resveratrol (3), 1-nonacosanol (4).
综合运用薄层层析(TLC),硅胶柱层析(CC),凝胶色谱(Sephadex LH-20)、反相硅胶柱层析(ODS)和高效液相色谱(HPLC)等色谱分离方法,从海洋细菌Bacillaceae sp v107代谢产物中分离得到4个化合物,采用现代波谱技术核磁共振谱1D-NMR(~1H-NMR, 13C-NMR, DEPT)和2D-NMR (~1H-~1HCOSY, HMBC, HMQC, NOESY)波谱、质谱(EIMS, ESIMS)和红外光谱(IR)手段鉴定了它们的结构,分别为:辅酶Q10(1),β-谷甾醇(2),邻苯二甲酸二辛脂(3),十六烷酸甘油酯(4)。
从海洋真菌zp6代谢产物中分离得到14个化合物,分别为:(22E)-3β, 5α, 9α-三羟基-麦角甾-7, 22-二烯-6-酮(1),5α, 8α-环二氧-24-甲基麦角甾-6, 22-二烯-3β-醇(2),邻苯二甲酸二异丁酯(3),1, 3 ,5三甲基-尿嘧啶(4),赤藓糖醇(Erythrito) (5),4-乙酰氧基苯甲酸(6),丁二酸(7),邻苯二甲酸二辛脂(8),腺嘌呤核苷(adenosine) (9),(24R)-麦角甾-7, 22-二烯-3β, 5α, 6β-三醇(10),十八碳-9-烯酸(11),阿拉伯醇(12),4-氨基吡唑[3, 4-d]嘧啶(13),尿嘧啶核苷(14)。在对海洋真菌zp6代谢产物中分离所得到的化合物进行的抑菌活性实验中,化合物1对植物病原真菌大丽轮枝菌(Verticillium dahliae )和尖刀镰孢菌(Fusarium oxysporum)有抑菌活性;化合物10对植物病原真菌大丽轮枝菌(Verticillium dahliae ),黄瓜尖镰孢(Fusarium oxysporum f.sp.cucumarinum) ,尖刀镰孢菌(Fusarium oxysporum) ,辣椒疫霉(Phytophthora capsici )有抑菌活性。对其它化合物的抗菌活性研究,结果未显出抗菌活性。
从滇南苦刺花乙酸乙酯部分分离得到8个化合物,鉴定了其中的4个,分别为:高丽槐素(1),β-谷甾醇(2),白藜芦醇(3),正二十九醇(4)。
The thesis is divided into three parts: The first Part is the secondary metabolites of maritime bacterium Bacillaceae sp. v107. The second part is the secondary metabolites of maritime eumycete zp6 and the reseach about antibacterial activity. The third part is the research about chemical constituents of Sophora davidii.
A detailed separation and purification by using thin-layer chromatography (TLC), Sigel column chromatography (CC), gel column chromatography (Sephadex LH-20), reverse phase column chromatography (ODS) and high pressure liquid chromatography (HPLC). Four compounds were isolated from the secondary metabolites of maritime bacterium Bacillaceae sp. v107, and their structures were determined by extensive spectroscopic analysis including 1D-NMR (~1H-NMR, 13C-NMR, DEPT), 2D-NMR (~1H-~1HCOSY, HMBC, HMQC, NOESY), EIMS, ESIMS and IR. The structures of compounds were identified as following: coenzymeQ10 (1),β-sitosterol (2), Bis(2-ethylhexyl)phthalate (3), 1-O-hexadecanolenin (4).
Fourteen compounds were isolated from the secondary metabolites of maritime eumycete zp6, and their structures were identified as following: (22E)-3β, 5α, 9α-trihydroxy-ergosta-7, 22-dien-6-one(1), 5α, 8α-epidioxy-ergosta-6, 22-dien-3β-ol (2), Bis(2-methylpropyl)ester (3), 1, 3, 5-trimethyl-2, 4(~1H, 3H)-pyrimidinedione (4), Erythrito (5), 4-acetoxybenozic acid (6), succinic acid (7), Bis(2-ethylhexyl)phthalate (8), adenosine (9), (24R)-ergosta-7, 22-diene-3β, 5α, 6β-trio1 (10), 9-Octadecenoic acid (11), arabinitol (12), 4-aminopyrazolo (3, 4-d) pyrimidine (13), uridine (14).
In the experiment of antibacterial activity, compound 1 show the active in antibacterial, suppressing Verticillium dahliae and Fusarium oxysporum growth; compound 10 also show the active in antibacterial, suppressing Verticillium dahliae, Fusarium oxysporum f.sp.cucumarinum, Fusarium oxysporum and Phytophthora capsici growth.
Eight compounds were isolated from the ethylacetate-solved portion of Sophora davidii, and four compounds were identified as: maackiain (1),β-sitosterol (2), resveratrol (3), 1-nonacosanol (4).
引文
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