亚稀褶黑菇等四种高等真菌的化学成分及共生菌根信号分子研究
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摘要
自然界的有毒蘑菇种类繁多,全球估计达1000种以上,我国的毒蘑菇(包括怀疑有毒的)多达400余种。至今为止,前人共分离了并鉴定的蘑菇毒素有70多个化合物,其结构类型主要有肽类、氨基酸、生物碱、萜类、联苯类、蛋白质等。在我国南方,近几年频频发生蘑菇中毒事件,但很多有毒蘑菇的毒性成分不清楚。弄清毒蘑菇的化学成分及其毒性成分,可为临床治疗提供可行的证据和药物开发提供理论依据。本文采用柱层析、薄层层析、高效液相色谱、质谱、核磁共振技术和化学反应等手段,对3种常被误食的有毒蘑菇的化学成分进行了研究。
从采自湖南湘阴的亚稀褶黑菇中分离并鉴定了8个化合物:5α,8α-epidioxy-(22E,24R)-ergosta-6,22-dien-3β-ol(1),(22E,24R)-ergosta-7,22-dien-3β,5α,6α-triol(cerevisterol)(2),(22E,24R)-7,22-diene-3β,5α,6β,9α-tetraol(3),3β,5α,9α-Trihydroxy-ergosta-7,22-dien-6-one(4),4-Methylcholest-7-en-3-ol(5),3β-linoleyloxyergost-7-ene(6),Catalpinic acid(7),(2S,3R,4E,8E)-1-(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2'-hydroxyheptadecanoyl]amino-9-methyl-4,8-octadecadiene(8)。其中化合物3和化合物4据文献报道,它们在肝细胞毒理实验中的LD_(50)分别为8μg/ml和63μg/ml,被确认为有细胞毒活性化合物。
从光盖伞子实体中分离鉴定了6个化合物:3β-羟基-5α,8α-过氧化麦角甾-6,22-二烯(1)、3β-linoleyloxyergost-7-ene(2)、胡萝卜苷(3)、神经酰胺(4)、5α,6α-过氧化麦角甾-8,22-二烯-3β,7α-二醇(5)、色氨酸(6)。
对采自湖南衡阳的大青褶伞子实体进行分离,获得纯菌丝。对大青褶伞的菌丝生长的培养条件及其发酵菌丝化学成分进行了研究。结果表明:大青褶伞菌丝生长的最适碳源为葡萄糖,最适氮源为蛋白胨,最佳培养温度是在25～30℃之间;在其发酵菌丝得到了4个化合物:5α,8α过氧化麦角甾-6,22-二烯-3β-醇(1)、麦角甾-7,22-二烯-3β,5α,6β-醇(2)、5α,6α-过氧化麦角甾-8(14),22-二烯-3β,70α-醇(3)、麦角甾-7,22-二烯-3β-醇(4)。
黑柄炭角菌(Xylaria nigripes)是一种名贵药用真菌,其菌核具有除湿、镇静安神、造血以及提高机体免疫功能等功效。其发酵菌丝作为一保健品已经投放市场,但目前对于黑柄炭角菌发酵菌丝中的化学成分和药理有效成分研究得还很少。为此,本文采用柱层析、薄层层析、质谱、核磁共振技术和化学反应等手段,对黑柄炭角菌发酵菌丝的化学成分及其活性进行了研究。从发酵菌丝的乙酸乙酯部分分离得到了9个化合物,经理化性质和波谱数据分析分别鉴定为:5-羟基-7-甲氧基-2-甲基-4-二氢色原酮(1),5,7-二羟基-2-甲基-4-二氢色原酮(2),5-羟基-2-甲基-4-二氢色原酮(3),1-(2,6-二羟基苯)-3-羟基-丁酮(4),5α,8α-过氧化麦角甾-6,22-二烯-3β-醇(5),麦角甾-7,22-二烯-3β-醇(6),大戟醇(7),β-谷甾醇(8)和2-(4-羟基苯)-乙醇(9)。这些化合物均为首次从该菌分离得到,其中化合物1和2为首次从天然产物中分离得到。在DPPH抗氧化试验中表明化合物4具有明显的抗氧化活性。
共生真菌要与植物产生菌根,才能完成其生活史,所以目前能人工栽培的共生菌类不多,而很多共生真菌是美味的食用菌。本文开展了红汁乳菇(Lactarius hatsutake)-马尾松(Pinus massoniana)产生共生菌根的信号分子研究。采用柱层析、薄层层析、质谱和核磁共振技术等手段,对马尾松的化学成分进行分离鉴定,用其化学成分进行菌丝培养,寻求得到马尾松刺激红汁乳菇生长的信号分子。从马尾松乙酸乙酯部分分离得到了10个化合物:松脂素(1),Matairesinol(2),(-)-nortrachelogenin(3),Balanophonin(4),1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(5),tanegool(6),Cedrusin(7),(-)-threo(8),(+)-threo(9),pinosylvin(10)。从马尾松石油醚部分分离得到了20个化合物:8(14),15-Pimaradien-19-oic acid(11),15-甲氧基-松香酯(12),海松酸(13),罗汉松酸(14),12-羟基脱氢松香酸(15),脱氢松香酸(16),15-羟基-脱氢松香酯(17),3β-methoxyserrat-14-en-21-one(18),3β-hydroxyserrat-14-en-21-one(19),3β-methoxyserrat-14-en-21-one-30-al(20),(24R)-stigmast-4-ene-3-one(21),β-谷甾醇(22),(E)-3-hydroxy-5-methoxy-stilbene(23),4-hydroxy-3-methoxycinn-amaldehyde(24),(E)-ferulic acidtetracosylester(25),alkylferulates(26),pinocembin(27),coniferaldehyde(28),3-hydroxy-1,7,7-trimrthyl bicycle(29),4-hydroxy-1,7,7-trimrthylbicycle(30)。其中松脂素、Balanophonin、Cedrusin对红汁乳菇菌丝的生长有促进作用。
It has been estimated that there are about 1000 poisonous mushroom in the world and more than 400 species in China.To now then, about 70 toxic compounds have been isolated and identified from poisonous mushroom.Poisoning cases occurred by poisonous mushroom had been occurred frequently in recent years in Southern China.But the toxic compounds haven't been known in many poisonous mushroom.For understanding the toxins of some poisonous mushrooms,the chemical constituents of Russula subigricans Hongo,Psilocybe spp and Chlorophyllum molybdites have been isolated and identified by the means of column chromatography,TLC and spectrum technology.
Eight compounds have been islolated and identified on the basis of the spectroscopic data from the Russula subigricans Hongo:5α,8α-epidioxy -(22E,24R)-ergosta-6,22-dien-3β-ol(1),(22E,24R)-ergosta-7 ,22-dien-3β,5α,6α-triol(cerevisterol)(2),(22E,24R)-7,22-diene-3β, 5α,6β,9α-tetraol(3),3β,5α,9α-trihydroxy-ergosta-7,22-dien-6-one (4),4-Methylcholest-7-en-3-ol(5),3β-linoleyloxyergost-7-ene(6), Catalpinic acid(7),(2S,3R,4E,8E)-1-(β-D-glucopyranosyl)-3-hydroxy-2 -[(R) -2'-hydroxyheptadecanoyl]amino-9-methyl-4,8-octadecadiene (8)。Compound 3 and compound 4 exhibited cytotoxic activity according to references.
Six compounds have been islolated and identified for the first time on the basis of the spectroscopic data from the Psilocybe spp.5α,8α-epidioxy-(22E,24R)-ergosta-6,22-dien-3β-ol(1),3β-linoleyloxyergost-7 -ene(2),β-Carotene(3),5α,6α-epoxyergosta-8(14),22-diene-3β,7β-diol (5)、tryptophan(6)。
The optimal culture condition of Chlorophyllum molybdites and chemical constituents of its mycelium have been studied.The results showed that the optimal carbon-source and nitrogen-source were sucrose and peptone respectively.The optimal culture temperature was 25～30℃. Four compounds have been isolated and identified on the basis of the spectroscopic data from the Chlorophyllum,molybdites:5α,8α-epidioxy -(22E,24R)-ergosta-6,22-dien-3β-ol(1),(22E,24R)-ergosta-7,22-dien-3β,5α6α-triol(2),poxyergosta-8(14),22- diene-3β,7α-ol(3),3β-linoleyloxyergost -7-ene(4)。
Xylaria nigripes(KI.) Sacc,a rare fungus,had also been known as wulingshen,it was a well-known nutritious medicinal fungus,which have the benefit spirit,key brain,keep blood and tranquilize the nerves effect. Although the fermented mycelium as a medicinal product had come into market,the bioactive compounds have been understood little.So the chemical constituents of the fermented mycelium of X.nigripes were investigated.Nine known compounds:5-hydroxy-7-methoxy-2-methyl-4 -chromanone(1),5,7-dihydroxy-2-methyl-4-chromanone(2),5-hydroxyl -2-methyl-4-chromanone(3),1-(2,6-dihydroxyphenyl)-3-hydroxybutan -one(4),5α,8α-epidioxyergosta -6,22-dien-3β-ol(5), ergost-7,22-dien -3,5,6-triol(6),euphorbol(7),β-sitosterol(8) and 2-(4-hydroxyphenyl )-ethanol(9) were isolated and identified from Xylaria nigripes for the first time,and their structures were mainly determined by MS and NMR methods.Compounds 1 and 2 were isolated for the first time as the natural product.Compound 4 exhibited the strongest radical-scavenging activity according to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.
Without the symbiosis,mycorrhizal fungi cann't complete its life history.Signalling molecules secreted by plant in low concentrations promote the mycorrhizal fungi to grow.For finding out the signalling molecules released by Pinus massoniana Lamb which can promote the growth of Lactarius deliciosus.This dissertation studies on chemical constituents of Pinus massoniana by the means of column chromatography,TLC and spectrum technology to isolate and identify the structure.31 compounds have been isolated and identified from Pinus massoniana Lamb.10 compounds:pinoresinol(1),Matairesinol(2),(-)-nortrachelogenin (3),Balanophonin(4),1,2-bis-(4-hydroxy-3-methoxyphenyl )-propane-1,3-diol(5),tanegoo(6),Cedrusin(7),(-)-threo (8),(+)-threo(9),pinosylvin(10),had been isolated from EtOH fraction of Pinus massoniana.20 compounds:8(14),15-Pimaradien-19-oic acid(11),15-methoxy-abietic(12),pimaric(13),podocarpic(14),12-hydroxydehydroabietic acid(15),dehydroabietic acid(16),15-hydroxydehydroabietic (17),3β-methoxyserrat-14-en-21-one(18),3β-hydroxyserrat -14-en-21-one(19),3β-methoxyserrat-14-en-21-one -30-al (20),(24R)-stigmast -4-ene-3-one(21),β-sitosterol(22),(E)-3-hydroxy-5 -methoxy-stilbene(23),4-hydroxy-3-methoxycinn-amaldehyde(24), (E)-ferulic acidtetracosyl ester(25),alkylferulates(26),pinocembin(27), coniferaldehyde(28),3-hydroxy-1,7,7-trimrthyl bicycle(29),4- hydroxy-1 ,7,7-trimrthyl bicycle(30),had been isolated from butanol fraction of Pinus massoniana Lamb.Among these compounds,three compounds: pinoresinol,Balanophonin,Cedrusin can promote the growth of Lactarius deliciosus.
从采自湖南湘阴的亚稀褶黑菇中分离并鉴定了8个化合物:5α,8α-epidioxy-(22E,24R)-ergosta-6,22-dien-3β-ol(1),(22E,24R)-ergosta-7,22-dien-3β,5α,6α-triol(cerevisterol)(2),(22E,24R)-7,22-diene-3β,5α,6β,9α-tetraol(3),3β,5α,9α-Trihydroxy-ergosta-7,22-dien-6-one(4),4-Methylcholest-7-en-3-ol(5),3β-linoleyloxyergost-7-ene(6),Catalpinic acid(7),(2S,3R,4E,8E)-1-(β-D-glucopyranosyl)-3-hydroxy-2-[(R)-2'-hydroxyheptadecanoyl]amino-9-methyl-4,8-octadecadiene(8)。其中化合物3和化合物4据文献报道,它们在肝细胞毒理实验中的LD_(50)分别为8μg/ml和63μg/ml,被确认为有细胞毒活性化合物。
从光盖伞子实体中分离鉴定了6个化合物:3β-羟基-5α,8α-过氧化麦角甾-6,22-二烯(1)、3β-linoleyloxyergost-7-ene(2)、胡萝卜苷(3)、神经酰胺(4)、5α,6α-过氧化麦角甾-8,22-二烯-3β,7α-二醇(5)、色氨酸(6)。
对采自湖南衡阳的大青褶伞子实体进行分离,获得纯菌丝。对大青褶伞的菌丝生长的培养条件及其发酵菌丝化学成分进行了研究。结果表明:大青褶伞菌丝生长的最适碳源为葡萄糖,最适氮源为蛋白胨,最佳培养温度是在25～30℃之间;在其发酵菌丝得到了4个化合物:5α,8α过氧化麦角甾-6,22-二烯-3β-醇(1)、麦角甾-7,22-二烯-3β,5α,6β-醇(2)、5α,6α-过氧化麦角甾-8(14),22-二烯-3β,70α-醇(3)、麦角甾-7,22-二烯-3β-醇(4)。
黑柄炭角菌(Xylaria nigripes)是一种名贵药用真菌,其菌核具有除湿、镇静安神、造血以及提高机体免疫功能等功效。其发酵菌丝作为一保健品已经投放市场,但目前对于黑柄炭角菌发酵菌丝中的化学成分和药理有效成分研究得还很少。为此,本文采用柱层析、薄层层析、质谱、核磁共振技术和化学反应等手段,对黑柄炭角菌发酵菌丝的化学成分及其活性进行了研究。从发酵菌丝的乙酸乙酯部分分离得到了9个化合物,经理化性质和波谱数据分析分别鉴定为:5-羟基-7-甲氧基-2-甲基-4-二氢色原酮(1),5,7-二羟基-2-甲基-4-二氢色原酮(2),5-羟基-2-甲基-4-二氢色原酮(3),1-(2,6-二羟基苯)-3-羟基-丁酮(4),5α,8α-过氧化麦角甾-6,22-二烯-3β-醇(5),麦角甾-7,22-二烯-3β-醇(6),大戟醇(7),β-谷甾醇(8)和2-(4-羟基苯)-乙醇(9)。这些化合物均为首次从该菌分离得到,其中化合物1和2为首次从天然产物中分离得到。在DPPH抗氧化试验中表明化合物4具有明显的抗氧化活性。
共生真菌要与植物产生菌根,才能完成其生活史,所以目前能人工栽培的共生菌类不多,而很多共生真菌是美味的食用菌。本文开展了红汁乳菇(Lactarius hatsutake)-马尾松(Pinus massoniana)产生共生菌根的信号分子研究。采用柱层析、薄层层析、质谱和核磁共振技术等手段,对马尾松的化学成分进行分离鉴定,用其化学成分进行菌丝培养,寻求得到马尾松刺激红汁乳菇生长的信号分子。从马尾松乙酸乙酯部分分离得到了10个化合物:松脂素(1),Matairesinol(2),(-)-nortrachelogenin(3),Balanophonin(4),1,2-bis-(4-hydroxy-3-methoxyphenyl)-propane-1,3-diol(5),tanegool(6),Cedrusin(7),(-)-threo(8),(+)-threo(9),pinosylvin(10)。从马尾松石油醚部分分离得到了20个化合物:8(14),15-Pimaradien-19-oic acid(11),15-甲氧基-松香酯(12),海松酸(13),罗汉松酸(14),12-羟基脱氢松香酸(15),脱氢松香酸(16),15-羟基-脱氢松香酯(17),3β-methoxyserrat-14-en-21-one(18),3β-hydroxyserrat-14-en-21-one(19),3β-methoxyserrat-14-en-21-one-30-al(20),(24R)-stigmast-4-ene-3-one(21),β-谷甾醇(22),(E)-3-hydroxy-5-methoxy-stilbene(23),4-hydroxy-3-methoxycinn-amaldehyde(24),(E)-ferulic acidtetracosylester(25),alkylferulates(26),pinocembin(27),coniferaldehyde(28),3-hydroxy-1,7,7-trimrthyl bicycle(29),4-hydroxy-1,7,7-trimrthylbicycle(30)。其中松脂素、Balanophonin、Cedrusin对红汁乳菇菌丝的生长有促进作用。
It has been estimated that there are about 1000 poisonous mushroom in the world and more than 400 species in China.To now then, about 70 toxic compounds have been isolated and identified from poisonous mushroom.Poisoning cases occurred by poisonous mushroom had been occurred frequently in recent years in Southern China.But the toxic compounds haven't been known in many poisonous mushroom.For understanding the toxins of some poisonous mushrooms,the chemical constituents of Russula subigricans Hongo,Psilocybe spp and Chlorophyllum molybdites have been isolated and identified by the means of column chromatography,TLC and spectrum technology.
Eight compounds have been islolated and identified on the basis of the spectroscopic data from the Russula subigricans Hongo:5α,8α-epidioxy -(22E,24R)-ergosta-6,22-dien-3β-ol(1),(22E,24R)-ergosta-7 ,22-dien-3β,5α,6α-triol(cerevisterol)(2),(22E,24R)-7,22-diene-3β, 5α,6β,9α-tetraol(3),3β,5α,9α-trihydroxy-ergosta-7,22-dien-6-one (4),4-Methylcholest-7-en-3-ol(5),3β-linoleyloxyergost-7-ene(6), Catalpinic acid(7),(2S,3R,4E,8E)-1-(β-D-glucopyranosyl)-3-hydroxy-2 -[(R) -2'-hydroxyheptadecanoyl]amino-9-methyl-4,8-octadecadiene (8)。Compound 3 and compound 4 exhibited cytotoxic activity according to references.
Six compounds have been islolated and identified for the first time on the basis of the spectroscopic data from the Psilocybe spp.5α,8α-epidioxy-(22E,24R)-ergosta-6,22-dien-3β-ol(1),3β-linoleyloxyergost-7 -ene(2),β-Carotene(3),5α,6α-epoxyergosta-8(14),22-diene-3β,7β-diol (5)、tryptophan(6)。
The optimal culture condition of Chlorophyllum molybdites and chemical constituents of its mycelium have been studied.The results showed that the optimal carbon-source and nitrogen-source were sucrose and peptone respectively.The optimal culture temperature was 25～30℃. Four compounds have been isolated and identified on the basis of the spectroscopic data from the Chlorophyllum,molybdites:5α,8α-epidioxy -(22E,24R)-ergosta-6,22-dien-3β-ol(1),(22E,24R)-ergosta-7,22-dien-3β,5α6α-triol(2),poxyergosta-8(14),22- diene-3β,7α-ol(3),3β-linoleyloxyergost -7-ene(4)。
Xylaria nigripes(KI.) Sacc,a rare fungus,had also been known as wulingshen,it was a well-known nutritious medicinal fungus,which have the benefit spirit,key brain,keep blood and tranquilize the nerves effect. Although the fermented mycelium as a medicinal product had come into market,the bioactive compounds have been understood little.So the chemical constituents of the fermented mycelium of X.nigripes were investigated.Nine known compounds:5-hydroxy-7-methoxy-2-methyl-4 -chromanone(1),5,7-dihydroxy-2-methyl-4-chromanone(2),5-hydroxyl -2-methyl-4-chromanone(3),1-(2,6-dihydroxyphenyl)-3-hydroxybutan -one(4),5α,8α-epidioxyergosta -6,22-dien-3β-ol(5), ergost-7,22-dien -3,5,6-triol(6),euphorbol(7),β-sitosterol(8) and 2-(4-hydroxyphenyl )-ethanol(9) were isolated and identified from Xylaria nigripes for the first time,and their structures were mainly determined by MS and NMR methods.Compounds 1 and 2 were isolated for the first time as the natural product.Compound 4 exhibited the strongest radical-scavenging activity according to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical.
Without the symbiosis,mycorrhizal fungi cann't complete its life history.Signalling molecules secreted by plant in low concentrations promote the mycorrhizal fungi to grow.For finding out the signalling molecules released by Pinus massoniana Lamb which can promote the growth of Lactarius deliciosus.This dissertation studies on chemical constituents of Pinus massoniana by the means of column chromatography,TLC and spectrum technology to isolate and identify the structure.31 compounds have been isolated and identified from Pinus massoniana Lamb.10 compounds:pinoresinol(1),Matairesinol(2),(-)-nortrachelogenin (3),Balanophonin(4),1,2-bis-(4-hydroxy-3-methoxyphenyl )-propane-1,3-diol(5),tanegoo(6),Cedrusin(7),(-)-threo (8),(+)-threo(9),pinosylvin(10),had been isolated from EtOH fraction of Pinus massoniana.20 compounds:8(14),15-Pimaradien-19-oic acid(11),15-methoxy-abietic(12),pimaric(13),podocarpic(14),12-hydroxydehydroabietic acid(15),dehydroabietic acid(16),15-hydroxydehydroabietic (17),3β-methoxyserrat-14-en-21-one(18),3β-hydroxyserrat -14-en-21-one(19),3β-methoxyserrat-14-en-21-one -30-al (20),(24R)-stigmast -4-ene-3-one(21),β-sitosterol(22),(E)-3-hydroxy-5 -methoxy-stilbene(23),4-hydroxy-3-methoxycinn-amaldehyde(24), (E)-ferulic acidtetracosyl ester(25),alkylferulates(26),pinocembin(27), coniferaldehyde(28),3-hydroxy-1,7,7-trimrthyl bicycle(29),4- hydroxy-1 ,7,7-trimrthyl bicycle(30),had been isolated from butanol fraction of Pinus massoniana Lamb.Among these compounds,three compounds: pinoresinol,Balanophonin,Cedrusin can promote the growth of Lactarius deliciosus.
引文
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