层孔菌属药用真菌阿里红和木蹄的化学成分与生物活性研究
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摘要
阿里红(Fomes officinalis Ames)是新疆维吾尔医常用的民族药,为多孔菌科(Polyporaceace)层孔菌属(Fomes)真菌,主要分布在我国西部和东北。药理实验表明具有止咳化痰、抗氧化、增强免疫力作用。为维吾尔药复方阿里红片的主要成分之一,主要用于祛痰平喘。由于真菌代谢产物具有多种结构类型和生理活性,是寻找新的天然药物的重要来源。作为疗效显著的大型真菌类民族药,有关阿里红化学成分和药理活性的研究较少,对质量标准控制方面的研究更为鲜有。因此本研究以阿里红为对象,在前期研究工作的基础上,对其化学成分、药理活性和质量控制等方面进行了系统的研究,并对部分单体成分进行了药理活性筛选。同时以阿里红中分离的到的二十余个羊毛甾烷型三萜为对象进行ESI-MS/MS多级裂解规律研究。另外对阿里红中主要化合物类型-羊毛甾烷三萜化学成分和药理作用的研究现状进行了综述。本研究取得了一定的进展,现归纳总结如下。
从阿里红子实体的乙醇提取物中,利用现代制备色谱技术和分离方法对阿里红子实体的石油醚、氯仿、乙酸乙酯等部分进行系统分离,得到34个化合物。综合应用红外光谱(IR)、质谱(EIMS、ESIMS)及核磁共振光谱(谱(HNMR、13CNMR、1H-1HCOSY、HMBC、HSQC、DEPT)等现代波谱学方法和X光衍射技术,并辅以化学方法鉴定了其中的32个,它们分别属于三萜类、倍半萜类、氨基酸类、甾醇类,其中有3个为新化合物,4个为首次从该真菌中分得。
新化合物分别为锥满烷型倍半萜类化合物,命名为：阿红酸(3,7-dihydroxy-driman-11-oic acid),羊毛甾烷型三萜类化合物,命名为：阿里红素(18,23-epoxy-9a-ethoxy-3a-carbohydroxyacetyloxy-24a-methyl-lanost-8-en-26,23-olide),氨基酸类化合物命名为：阿里红氨酸[2-(1-carboxyhexadecylamino)-2-aminosuccinic acid]。
已知化合物鉴定为：fomitopsins C, albicanic acid,齿孔醇,3-酮基-去氢硫色多孔菌酸,去氢齿孔酸,齿孔酸,硫色多孔菌酸,去氢硫色多孔菌酸,去氢齿孔酮酸,变孔绚孔菌酸D,变孔绚孔菌酸C,阿里红酸,fomlactone A, fomlactone B, fomlactone C,阿里红醇A,阿里红醇B,阿里红酸A,阿里红酸B,阿里红酸C,阿里红酸D,阿里红酸E,阿里红酸F,阿里红酸G,落叶松酸,麦角甾醇,麦角甾-7,22烯-3β醇,麦角甾-5,22烯-3β醇,正十二烷。
在本室前期对阿里红的化学成分初步探索基础上,我们继续分离纯化工作对各单体化合物进行一定量的积累,以部分单体化合物通过乙酰胆碱酯酶模型筛选,反应系统中终浓度为5μg/mL和50μg/mL的乙酰胆碱酯酶抑制活性。结果表明,尽管与阳性药相比,活性相对较弱,但大部分化合物的活性具有浓度依赖性,抑制率随浓度升高而增加。同时我们还以MTT法和SRB法对得到的化合物进行了抗肿瘤的活性研究,对部分化合物进行了6个体外细胞模型的筛选,发现新化合物阿红酸对HL-60和BGC-823在较高浓度具有一定的抑制活性,而其他化合物作用不明显,但有一定浓度和活性的依赖性。
对分离得到羊毛甾烷三萜化合物标品进行ESI/MSn多级裂解规律研究,利用LC-ESI/MSn技术在优化指纹图谱条件的基础上,结合得到的裂解规律对阿里红原药材中的化学成分进行鉴别和结构推断,该裂解规律可帮助羊毛甾烷型三萜的鉴别和深入研究阿里红化学成分。对不同产地的16批阿里红样品的甲醇提取物进行5个特征成分的同时定量分析,为阿里红药材的质量控制提供科学依据。
木蹄层孔菌[Fomes fomentarius(L.Ex.Fr.)]为多孔菌科(Polyporaceae)层孔菌属(Fomes)大型真菌,又称木蹄。多年生,多生于阔叶树干上。广泛分布于我国东北、西南和西部等地区。药用有消积化瘀作用,其味微苦,性平。木蹄作为民间药物历史悠久,用于治疗食道癌、胃癌、子宫癌等。其药用部位为子实体,现代药理研究表明,木蹄粗提物具有抗肿瘤,抗氧化,增强免疫功能等活性。为了进一步阐明其药效物质基础,寻找新的有效部位及有效成分,我们对木蹄层孔菌的化学成分进行了研究,部分单体化合物进行了活性筛选。
从木蹄的95%乙醇提取物中分离得到了16个化合物,鉴定了其中的14个化合物,分别为fomentarinin (I),泡桐素(Ⅱ),原儿茶醛(Ⅲ),4-(3,4-二羟苯基)-3-丁烯-2-酮(Ⅳ),丁香酸(Ⅴ),丁香醇(Ⅵ),香草醛(Ⅶ),5α,8α-过氧化麦角甾-6,22-二烯-3β醇(Ⅷ),麦角甾-7,22-二烯-3β-醇(Ⅸ),麦角甾-7,22-二烯-3,6-二酮(Ⅹ),麦角甾-7,22-二烯-3-酮(Ⅺ),麦角甾醇(Ⅻ),β-谷甾醇(ⅩⅢ),2-羟基-蜡酸乙酯(ⅩⅣ)。
化合物Ⅰ为新化合物,命名为：木蹄素(ethyl tetrahydro-5-tridecylfuran-2-carboxylate)。化合物Ⅱ-Ⅷ、Ⅹ、ⅩⅢ、ⅩⅣ均为首次从该种真菌中分离得到。通过体外抗肿瘤活性筛选,结果表明进行测试的化合物在浓度较高时对不同细胞株有一定抑制作用,为进一步研究木蹄中有效成分的药理活性提供依据。
综上,本文主要系统地研究了层孔菌属的两个大型药用真菌阿里红和木蹄的化学成分和药理活性,以及阿里红的ESI-MS/MS多级裂解规律和成分定量分析等方面的研究,建立了阿里红药材的质量控制标准,为进一步的开发和利用这两个药用真菌提供了物质基础和理论依据。
Fomes officinalis, a fungus of Fomes genus in Polyporaceace family, is a wood rotting fungus which is found on the trunks of living or dead coniferous trees in the northern regions of China and in the Pacific Northwest United States, Canada and in Europe. It is traditionally used in Chinese Uigur prescription to treat cough and asthma. As a folk medicine, the fruit body of F. officinialis is traditionally used in the treatment of coughs, gastric cancer, rheumatism and hydropsia. Modern pharmacological studies have shown that the extract of A-Li-Hong have a variety of pharmacological action including:anti-tumor, eliminating phlegm, scavenging hydroxyl radical and enhancement of anti-stress. However, there have been no quantitative method to control the quality of crude drug in the Drug Specifications Promulgated by the Ministry of Public Health, PR China. Therefore, a simple and accurate HPLC-DAD-ESI/MS method was developed in this study for the simultaneous quantification and identification of the main bioactive constituents in F. officinalis. In order to obtain a more comprehensive understanding of its effective physiological constituents, in this doctoral dissertation, the systematic phytochemical and pharmacological studies have been carried out.
Thirty-four compounds were isolated from the ethanol extracts of its dried sclerotium. On the basis of various modern spectroscopic analysis(IR, UV, MS,'HNMR,13CNMR, 'H-'HCOSY, HMBC, HSQC, DEPT) and classical chemical methods, thirty-twor compounds were determined, of which three were new, seven were isolated from this fungus for the first time.
The new compounds'structures were determined as follows:fomic acid(3, 7-dihydroxy-driman-l 1-oic acid), fomefficinin(18,23-epoxy-9a-ethoxy-3a-carbohydroxy acetyloxy-24a-methyl-lanost-8-en-26,23-olide),2-(1-carboxyhexadecylamino)-2-amino-succinic acid.
The known compounds were identified as albicanic acid, fomitopsins C, eburicol,3-keto-dehydrosulfurenic acid, dehydroeburicoic acid, eburicoic acid, sulphurenic acid, dehydrosulphurenic acid, dehydroeburiconic acid, versisponic acid D, versisponic acid C, fomefficinic acid A, fomefficinic acid B, fomefficinic acid C, fomefficinic acid D, fomefficinic acid E, fomefficinic acid F, fomefficinic acid G, fomefficinol A, fomefficinol B, officinalic acid, fomlactone B, fomlactone A, fomlactone C, laricinolic acid, ergosterol, ergosta-7,22,dien-3(3-ol, ergosta-5,22,dien-3β-ol, dodecane.
A simple and accurate HPLC-UV method was developed for the simultaneous quantification of bioactive triterpenes in the fruit bodies of F. officinalis. The developed assay could be considered as a suitable quality control method for this folk medicine. Fragmentation study of isolated lanostane type triterpenes in F. officinalis by LC-ESI could help to identify the constituents with skeleton of lanostane triterpene.
We tested 12 compounds by acetylcholinesterase activity model, with the minimum and maximum concentration of 5μg/mL and 50μg/mL. The results show that major of the comounds performed weak activity compared with the positive control and they showed inhibition activity with a concentration-dependent.At the same time,Some of the compounds were tested for cytotoxicity against six human cancer lines in vitro.We found that the new sesquiterpene named fomic acid showed inhibitory activity to HL-60 and BGC-823 cell lines at a high concentration, otherwise, the other compounds do not have obvious activity but concentration-dependent.HL-60, Bel-7402 and KB cancer lines in vitro, and they appeared to be modestly active.
Fomes fomentarius(L.Ex.Fr.), is a folk medicinal fungus of Polyporaceae in family. It has the function of anti-tumor, eliminating phlegm, scavenging hydroxyl radical and enhancement of anti-stress. In order to find its effective compounds, we made a systematic research on this fungus.
Using kinds of chromatography technique,16 compounds were isolated from the seeds alcohol extract of F. fomentarius. On the basis of various modern spectroscopic analyzing,14 compounds were determined, The new compound's structure was determined as:fomentarinin (ethyl tetrahydro-5-tridecylfuran-2-carboxylate) (Ⅰ). The known compounds were identified as paulownin (II), protocatechualdehyde (Ⅲ), 4-(3,4-dihydroxyphenyl)-but-3-en-2-one (IV), syringic acid (V), syringyl alcohol(VI), vanillin(VII),5α,8a-epidioxyergosta-6,22-dien-3β-ol(VIII), ergosta-7,22-dien-3β-ol (IX), ergosta-7,22-diene-3,6-dione (X), ergosta-7,22-dien-3-one(XI), ergosterol(XII), P-sitosterol (XIII),2-hydroxy-hexacosanoic acid ethyl ester(XIV). Compound II-Ⅷ、X、XIII and XIV were isolated from F. fomentarius for the first time.
Some of the compounds were tested for cytotoxicity against four human cancer lines in vitro. We found that protocatechualdehyde and 4-(3,4-dihydroxyphenyl)-but-3-en-2-one showed inhibitory activity to BGC-823 and Bel-7402 cell lines at a high concentration.
从阿里红子实体的乙醇提取物中,利用现代制备色谱技术和分离方法对阿里红子实体的石油醚、氯仿、乙酸乙酯等部分进行系统分离,得到34个化合物。综合应用红外光谱(IR)、质谱(EIMS、ESIMS)及核磁共振光谱(谱(HNMR、13CNMR、1H-1HCOSY、HMBC、HSQC、DEPT)等现代波谱学方法和X光衍射技术,并辅以化学方法鉴定了其中的32个,它们分别属于三萜类、倍半萜类、氨基酸类、甾醇类,其中有3个为新化合物,4个为首次从该真菌中分得。
新化合物分别为锥满烷型倍半萜类化合物,命名为：阿红酸(3,7-dihydroxy-driman-11-oic acid),羊毛甾烷型三萜类化合物,命名为：阿里红素(18,23-epoxy-9a-ethoxy-3a-carbohydroxyacetyloxy-24a-methyl-lanost-8-en-26,23-olide),氨基酸类化合物命名为：阿里红氨酸[2-(1-carboxyhexadecylamino)-2-aminosuccinic acid]。
已知化合物鉴定为：fomitopsins C, albicanic acid,齿孔醇,3-酮基-去氢硫色多孔菌酸,去氢齿孔酸,齿孔酸,硫色多孔菌酸,去氢硫色多孔菌酸,去氢齿孔酮酸,变孔绚孔菌酸D,变孔绚孔菌酸C,阿里红酸,fomlactone A, fomlactone B, fomlactone C,阿里红醇A,阿里红醇B,阿里红酸A,阿里红酸B,阿里红酸C,阿里红酸D,阿里红酸E,阿里红酸F,阿里红酸G,落叶松酸,麦角甾醇,麦角甾-7,22烯-3β醇,麦角甾-5,22烯-3β醇,正十二烷。
在本室前期对阿里红的化学成分初步探索基础上,我们继续分离纯化工作对各单体化合物进行一定量的积累,以部分单体化合物通过乙酰胆碱酯酶模型筛选,反应系统中终浓度为5μg/mL和50μg/mL的乙酰胆碱酯酶抑制活性。结果表明,尽管与阳性药相比,活性相对较弱,但大部分化合物的活性具有浓度依赖性,抑制率随浓度升高而增加。同时我们还以MTT法和SRB法对得到的化合物进行了抗肿瘤的活性研究,对部分化合物进行了6个体外细胞模型的筛选,发现新化合物阿红酸对HL-60和BGC-823在较高浓度具有一定的抑制活性,而其他化合物作用不明显,但有一定浓度和活性的依赖性。
对分离得到羊毛甾烷三萜化合物标品进行ESI/MSn多级裂解规律研究,利用LC-ESI/MSn技术在优化指纹图谱条件的基础上,结合得到的裂解规律对阿里红原药材中的化学成分进行鉴别和结构推断,该裂解规律可帮助羊毛甾烷型三萜的鉴别和深入研究阿里红化学成分。对不同产地的16批阿里红样品的甲醇提取物进行5个特征成分的同时定量分析,为阿里红药材的质量控制提供科学依据。
木蹄层孔菌[Fomes fomentarius(L.Ex.Fr.)]为多孔菌科(Polyporaceae)层孔菌属(Fomes)大型真菌,又称木蹄。多年生,多生于阔叶树干上。广泛分布于我国东北、西南和西部等地区。药用有消积化瘀作用,其味微苦,性平。木蹄作为民间药物历史悠久,用于治疗食道癌、胃癌、子宫癌等。其药用部位为子实体,现代药理研究表明,木蹄粗提物具有抗肿瘤,抗氧化,增强免疫功能等活性。为了进一步阐明其药效物质基础,寻找新的有效部位及有效成分,我们对木蹄层孔菌的化学成分进行了研究,部分单体化合物进行了活性筛选。
从木蹄的95%乙醇提取物中分离得到了16个化合物,鉴定了其中的14个化合物,分别为fomentarinin (I),泡桐素(Ⅱ),原儿茶醛(Ⅲ),4-(3,4-二羟苯基)-3-丁烯-2-酮(Ⅳ),丁香酸(Ⅴ),丁香醇(Ⅵ),香草醛(Ⅶ),5α,8α-过氧化麦角甾-6,22-二烯-3β醇(Ⅷ),麦角甾-7,22-二烯-3β-醇(Ⅸ),麦角甾-7,22-二烯-3,6-二酮(Ⅹ),麦角甾-7,22-二烯-3-酮(Ⅺ),麦角甾醇(Ⅻ),β-谷甾醇(ⅩⅢ),2-羟基-蜡酸乙酯(ⅩⅣ)。
化合物Ⅰ为新化合物,命名为：木蹄素(ethyl tetrahydro-5-tridecylfuran-2-carboxylate)。化合物Ⅱ-Ⅷ、Ⅹ、ⅩⅢ、ⅩⅣ均为首次从该种真菌中分离得到。通过体外抗肿瘤活性筛选,结果表明进行测试的化合物在浓度较高时对不同细胞株有一定抑制作用,为进一步研究木蹄中有效成分的药理活性提供依据。
综上,本文主要系统地研究了层孔菌属的两个大型药用真菌阿里红和木蹄的化学成分和药理活性,以及阿里红的ESI-MS/MS多级裂解规律和成分定量分析等方面的研究,建立了阿里红药材的质量控制标准,为进一步的开发和利用这两个药用真菌提供了物质基础和理论依据。
Fomes officinalis, a fungus of Fomes genus in Polyporaceace family, is a wood rotting fungus which is found on the trunks of living or dead coniferous trees in the northern regions of China and in the Pacific Northwest United States, Canada and in Europe. It is traditionally used in Chinese Uigur prescription to treat cough and asthma. As a folk medicine, the fruit body of F. officinialis is traditionally used in the treatment of coughs, gastric cancer, rheumatism and hydropsia. Modern pharmacological studies have shown that the extract of A-Li-Hong have a variety of pharmacological action including:anti-tumor, eliminating phlegm, scavenging hydroxyl radical and enhancement of anti-stress. However, there have been no quantitative method to control the quality of crude drug in the Drug Specifications Promulgated by the Ministry of Public Health, PR China. Therefore, a simple and accurate HPLC-DAD-ESI/MS method was developed in this study for the simultaneous quantification and identification of the main bioactive constituents in F. officinalis. In order to obtain a more comprehensive understanding of its effective physiological constituents, in this doctoral dissertation, the systematic phytochemical and pharmacological studies have been carried out.
Thirty-four compounds were isolated from the ethanol extracts of its dried sclerotium. On the basis of various modern spectroscopic analysis(IR, UV, MS,'HNMR,13CNMR, 'H-'HCOSY, HMBC, HSQC, DEPT) and classical chemical methods, thirty-twor compounds were determined, of which three were new, seven were isolated from this fungus for the first time.
The new compounds'structures were determined as follows:fomic acid(3, 7-dihydroxy-driman-l 1-oic acid), fomefficinin(18,23-epoxy-9a-ethoxy-3a-carbohydroxy acetyloxy-24a-methyl-lanost-8-en-26,23-olide),2-(1-carboxyhexadecylamino)-2-amino-succinic acid.
The known compounds were identified as albicanic acid, fomitopsins C, eburicol,3-keto-dehydrosulfurenic acid, dehydroeburicoic acid, eburicoic acid, sulphurenic acid, dehydrosulphurenic acid, dehydroeburiconic acid, versisponic acid D, versisponic acid C, fomefficinic acid A, fomefficinic acid B, fomefficinic acid C, fomefficinic acid D, fomefficinic acid E, fomefficinic acid F, fomefficinic acid G, fomefficinol A, fomefficinol B, officinalic acid, fomlactone B, fomlactone A, fomlactone C, laricinolic acid, ergosterol, ergosta-7,22,dien-3(3-ol, ergosta-5,22,dien-3β-ol, dodecane.
A simple and accurate HPLC-UV method was developed for the simultaneous quantification of bioactive triterpenes in the fruit bodies of F. officinalis. The developed assay could be considered as a suitable quality control method for this folk medicine. Fragmentation study of isolated lanostane type triterpenes in F. officinalis by LC-ESI could help to identify the constituents with skeleton of lanostane triterpene.
We tested 12 compounds by acetylcholinesterase activity model, with the minimum and maximum concentration of 5μg/mL and 50μg/mL. The results show that major of the comounds performed weak activity compared with the positive control and they showed inhibition activity with a concentration-dependent.At the same time,Some of the compounds were tested for cytotoxicity against six human cancer lines in vitro.We found that the new sesquiterpene named fomic acid showed inhibitory activity to HL-60 and BGC-823 cell lines at a high concentration, otherwise, the other compounds do not have obvious activity but concentration-dependent.HL-60, Bel-7402 and KB cancer lines in vitro, and they appeared to be modestly active.
Fomes fomentarius(L.Ex.Fr.), is a folk medicinal fungus of Polyporaceae in family. It has the function of anti-tumor, eliminating phlegm, scavenging hydroxyl radical and enhancement of anti-stress. In order to find its effective compounds, we made a systematic research on this fungus.
Using kinds of chromatography technique,16 compounds were isolated from the seeds alcohol extract of F. fomentarius. On the basis of various modern spectroscopic analyzing,14 compounds were determined, The new compound's structure was determined as:fomentarinin (ethyl tetrahydro-5-tridecylfuran-2-carboxylate) (Ⅰ). The known compounds were identified as paulownin (II), protocatechualdehyde (Ⅲ), 4-(3,4-dihydroxyphenyl)-but-3-en-2-one (IV), syringic acid (V), syringyl alcohol(VI), vanillin(VII),5α,8a-epidioxyergosta-6,22-dien-3β-ol(VIII), ergosta-7,22-dien-3β-ol (IX), ergosta-7,22-diene-3,6-dione (X), ergosta-7,22-dien-3-one(XI), ergosterol(XII), P-sitosterol (XIII),2-hydroxy-hexacosanoic acid ethyl ester(XIV). Compound II-Ⅷ、X、XIII and XIV were isolated from F. fomentarius for the first time.
Some of the compounds were tested for cytotoxicity against four human cancer lines in vitro. We found that protocatechualdehyde and 4-(3,4-dihydroxyphenyl)-but-3-en-2-one showed inhibitory activity to BGC-823 and Bel-7402 cell lines at a high concentration.
引文
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