红树植物内生真菌抗肿瘤次生代谢产物的研究
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摘要
在抗肿瘤活性(MTT法)筛选指导下,综合运用硅胶柱色谱、Sephadex LH-20柱色谱等多种色谱学分离手段,对两株具有细胞毒活性的真菌桔青霉(Penicillium citrinum)和灰黄青霉(Penicillium griseofulvum)的次生代谢产物进行了研究,共分离得到30个化合物。通过分析化合物的理化性质和利用现代波谱学手段(UV,IR,MS,1D NMR,2D NMR)鉴定了其中的23个化合物的结构,分别为:桔霉素(1),decarboxydihydrocitrinone(2),(3R~*,4S~*)-6,8-dihydroxy-3,4,7-trimethylisocoumarin(3),phenol A(4),3,4,5-trimethyl-1,2-benzenediol(5),threo-4-(3-hydroxybutan-2-yl)-3,6-dimethylbenzene-1,2-diol(6),threo-4-(3-hydroxybutan-2-yl)-3-methyl-6-acetylbenzene-1,2-diol(7),cyclocitrinol(8),neocyclocitrinol(9),尿苷(10),(3β,22E)-麦角甾-5,7,22-三烯-3-醇(11),(3β,5α,8α,22E)-5,8-过氧麦角甾-6,22-二烯-3-醇(12),(3β,5α,6α,7α,22E)-5,6-环氧麦角甾-8,22-二烯-3,7-二醇(13),(3β,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇(14),soyasapogenol B(15),citrinin H2(16),glycerol 1-9′,12′-octadecadienoate(17),胡萝卜苷(18),1-呋喃基-1,2-乙二醇(19),6,8-dihydroxy-3,4,5,7-tetramethylisochroman(20),(S)-3-(3,5-dihydroxy-2,4-methylphenyl)butan-2-one(21),scalusamide A(22),7,8,4′-trihydroxyisoflavone(23)。
其中化合物3,6,7为新化合物,化合物5为首次以天然产物的形式分离得到。化合物9为首次从桔青霉(Penicillium citrinum)中分离得到。
对部分化合物的抗肿瘤活性测试结果显示,化合物1、3和4具有中等强度的细胞毒活性。
本次研究结果为从海洋来源的真菌中寻找抗肿瘤药物的研究提供了科学依据。
In our study on the chemical constituents from endophytic fungi of mangrove plants,30 compounds were isolated from mangrove fungi Penicillium citrinum and Penicillium griseofulvum.So far 23 compounds were elucidated by the means of spectroscopic method(UV, IR,MS,1D and 2D NMR) and comparison of their physiccochemical properties with references: citrinin(1),decarboxydihydrocitrinone(2),(3R~*,4S~*)-6,8-dihydroxy-3,4,7-trimethyliso coumarin(3),phenol A(4),3,4,5-trimethyl-1,2-benzenediol(5),threo-4-(3-hydroxybutan-2-yl) -3,6-dimethylbenzene-1,2-diol(6),threo-4-(3-hydroxybutan-2-yl)-3-methyl-6-acetylbenzene-1, 2-diol(7),cyclocitrinol(8),neocyclocitrinol(9),uridine(10),ergosterol(11),ergosterol peroxide(12),(3β,5α,6α,7α,22E)-5,6-epoxyergosta-8,22-diene-3,7-diol(13),(3β,5α,6β,22E)-ergosta-7, 22-diene-3,5,6-triol(14),soyasapogenol B(15),citrinin H2(16),glycerol 1-9',12'-octadecadienoate (17),daucosterol(18),1-(2-furanyl)-1,2-ethanediol(19),6,8-dihydroxy-3, 4,5,7-tetramethylisochroman(20),(S)-3-(3,5-dihydroxy-2,4-methyl-phenyl)butan-2-one(21), scalusamide A(22),7,8,4'-trihydroxyisoflavone(23).Among them,compounds 3,6 and 7 were new compounds,compound 5 was a new natrual product,and compound 9 was isolated from Penicillium citrinum for the first time.
Cytotoxic activities of some compounds were evaluated by MTT method in vitro,and the results showed that compounds 1,3,and 4 were active components.
其中化合物3,6,7为新化合物,化合物5为首次以天然产物的形式分离得到。化合物9为首次从桔青霉(Penicillium citrinum)中分离得到。
对部分化合物的抗肿瘤活性测试结果显示,化合物1、3和4具有中等强度的细胞毒活性。
本次研究结果为从海洋来源的真菌中寻找抗肿瘤药物的研究提供了科学依据。
In our study on the chemical constituents from endophytic fungi of mangrove plants,30 compounds were isolated from mangrove fungi Penicillium citrinum and Penicillium griseofulvum.So far 23 compounds were elucidated by the means of spectroscopic method(UV, IR,MS,1D and 2D NMR) and comparison of their physiccochemical properties with references: citrinin(1),decarboxydihydrocitrinone(2),(3R~*,4S~*)-6,8-dihydroxy-3,4,7-trimethyliso coumarin(3),phenol A(4),3,4,5-trimethyl-1,2-benzenediol(5),threo-4-(3-hydroxybutan-2-yl) -3,6-dimethylbenzene-1,2-diol(6),threo-4-(3-hydroxybutan-2-yl)-3-methyl-6-acetylbenzene-1, 2-diol(7),cyclocitrinol(8),neocyclocitrinol(9),uridine(10),ergosterol(11),ergosterol peroxide(12),(3β,5α,6α,7α,22E)-5,6-epoxyergosta-8,22-diene-3,7-diol(13),(3β,5α,6β,22E)-ergosta-7, 22-diene-3,5,6-triol(14),soyasapogenol B(15),citrinin H2(16),glycerol 1-9',12'-octadecadienoate (17),daucosterol(18),1-(2-furanyl)-1,2-ethanediol(19),6,8-dihydroxy-3, 4,5,7-tetramethylisochroman(20),(S)-3-(3,5-dihydroxy-2,4-methyl-phenyl)butan-2-one(21), scalusamide A(22),7,8,4'-trihydroxyisoflavone(23).Among them,compounds 3,6 and 7 were new compounds,compound 5 was a new natrual product,and compound 9 was isolated from Penicillium citrinum for the first time.
Cytotoxic activities of some compounds were evaluated by MTT method in vitro,and the results showed that compounds 1,3,and 4 were active components.
引文
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