披针观音座莲和半边铁角蕨的化学成分及生物活性研究
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摘要
蕨类植物是一群最古老的高等植物,现存约有12 000种,广泛分布于世界各地,尤以热带亚热带最为丰富。中国分布的蕨类植物有2 600多种,占总数的1/5强。多种蕨类植物自古以来就被人类食用或作药用,《神农本草经》、《本草纲目》和《中药大辞典》中均有药用蕨类植物的记载。作为药用,主要包括清热解毒、消肿散瘀、抗菌消炎、解毒、驱虫、抗病毒、抗过敏、增强记忆力及增加冠脉血流量等作用。药用蕨类植物的化学成分研究,主要是针对鳞毛蕨科、凤尾蕨科、水龙骨科及骨碎补科等的部分植物。因此,大量药用蕨类植物有待阐明其化学成分并开发利用。我们选取了两种民间应用广泛,缺乏化学成分研究的两种蕨类植物:披针观音座莲(Angiopteris caudatiformis)和半边铁角蕨(Aspleniumunilaterale)作为研究对象。
披针观音座莲(Angiopteris caudatiformis)为云南傣族及土族民间草药,使用历史悠久。其根茎作为傣药称为“季马”,主要用于治疗传染性疾病如肠炎,痢疾和肺结核等病症。其根茎和须根作为土家族民间草药可用于治疗肺热咳喘,毒蛇咬伤,疔疮疖肿及外伤出血等病症。但是,至今未见有对其化学和药理活性研究报道。
本文首次对披针观音座莲根茎的化学成分和生物活性进行了研究。从披针观音座莲根茎95%乙醇提取物中分离鉴定了21个化合物,包括:酯类化合物6个:观音座莲内酯A(angiopterlactone A,CP1),观音座莲内酯B(angiopterlactoneB,CP2),紫萁内酯(osmundalactone,CP3),紫萁内酯苷(osmundalin,CP4),3,5-二羟基-γ-己内酯(3,5-dihydroxy-γ-caprolactone,CP5),和巯基乙酸乙酯(ethylthioglycolate,CP6)。甾体类化合物5个:胡萝卜苷(daucosterol,CP7),β-谷甾醇(β-sitosterol,CP8),豆甾-5,17(20)-二烯-3-醇(stigmasta-5,17(20)-dien-3-ol,CP9),豆甾-3-O-β-D-吡喃葡萄糖苷(stigmast-3-O-β-D-glucopyranoside,CP10),和7-羟基豆甾-4烯-3-酮(7-hydroxystigmast-4-en-3-one,CP11)。糖及其苷类化合物4个:麦芽酚-β-D-吡喃葡萄糖甙(maltol-β-D-glucopyranoside,CP12),α-葡萄糖(α-glucose,CP13),麦芽糖(maltose,CP14),和乙基-α-D-葡萄糖苷(ethyl-α-D-glucoside,CP15)。脂肪酸类化合物2个:棕榈酸(palmic acid,CP16)和硬脂酸(stearic acid,CP17)。其他类4个:丁烯二醛(malealdehyde,CP18),5-羟甲基糠醛(5-hydroxy-methyl-2-furaldehyde,CP19),1-O-α-D-glucopyranosyl-(2S,3R,4E,8Z)-2-N-palmitoyloctade-casphinga-4,8-dienine(CP20),和2,4-二羟基嘧啶(2,4-dihydroxy-pyrimidine,CP21)。其中,CP1和CP2为2个具有双内酯骨架的新化合物,除化合物CP4和CP8外,其余化合物均为首次从该属植物中分离得到,所有化合物均为首次从该植物中分离得到。
对披针观音座莲中分离得到的5个内酯类化合物进行了体外抗肿瘤活性和昆虫拒食活性的初筛,结果显示新化合物观音座莲内酯A(CP1)对宫颈癌传代(HeLa cell)细胞具有细胞毒活性,其IC_(50)值为68.8μM。化合物紫其内酯(CP3),紫萁内酯苷(CP4)在浓度分别为500ppm和1000ppm时,对两种受试幼虫Plutella xylostella和Heliothis virescens显示拒食活性。
半边铁角蕨(Asplenium unilaterale)为维吾尔族民间草药,具有清热解毒、止血等功效。利用多种色谱技术分别对披针观音座莲和半边铁角蕨的化学成分进行了系统的分离,从半边铁角蕨全草的甲醇提取物中分离鉴定了28个化合物,包括:紫罗兰酮类5个:(Z)-4-(2,6,6-三甲基亚环己-2-烯基)丁-2-醇((Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol,CPS4),淫羊藿次苷Ⅱ(icariside B_2,CPS5),citroside A(CPS6),6R,9R-3-酮-α-紫罗兰醇-9-O-β-D-吡喃葡萄糖苷((6R,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside,CPS7),和(6S,9R)-6-羟基-3-酮-α-紫罗兰醇-9-O-β-D-葡萄糖苷((6S,9R)-roseoside,CPS8)。香豆素类3个:6-甲基-2H-香豆-2-酮(6-methyl-2H-chromen-2-one,CPS9),6,7-二羟基-香豆素(6,7-dihydroxy-2H-1-benzopyran-2-one,CPS10),和gibepyrone D(CPS11)。三萜类2个:铁角蕨酸(asplenic acid,CPS1),和羽扇豆烷-3-酮(lupan-3-one,CPS12)。黄酮类1个:芹菜素-6-C-β-D-吡喃葡萄糖-7-C-6-鼠李糖吡喃糖苷(violanthin,CPS13)。甾醇类5个:β-谷甾醇(β-sitosterol,CPS14),胡萝卜苷(daucosterol,CPS15),22,23-二甲基胆甾-S-烯-3-醇(22,23-dimethylcholest-S-en-3-ol,CPS16),豆甾-3,5-二烯(stigmasta-3,5-diene,CPS17),和铁角蕨甾醇(asplenilol,CPS2)。脂肪族类6个:正三十四醇(1-tetratriacontanol,CPS18),正三十二醇(1-laccerol,CPS19),正二十四酸(carnaubic acid,CPS20),棕榈酸(palmitic acid,CPS21),硬脂酸(palmiticacid,CPS22),和花生酸甲酯(methyl arachidate,CPS23)。酯类3个:铁角蕨内酯(aspleniloide,CPS3),5-己烷呋喃-2(5H)-(5-hexylfuran-2(5H)-one,CPS24),和4,5-二羟基戊-异丁酯(4,5-dihydroxypentyl-isobutyrate,CPS25)。其他类3个:托可醌(tocopherylquinone,CPS26),2,4(1H,3H)-嘧啶二酮(2,4-(1H,3H)-pyrimidinedione,CPS27),和水苏糖(stachyose,CPS28)。其中,CPS1,CPS2和CPS3为新化合物,所有化合物均为首次从该属植物中分离得到。
本论文还对观音座莲属植物和铁角蕨属植物的国内外研究进展进行了归纳总结,为这两属蕨类植物资源的进一步研究与开发提供参考。
Ferns widely distributed in various areas throughout the world,particularly abundant in tropical and subtropical zones,belong to the oldest group of higher plants. Among them,more than 2,600 species exist in China,some of them are used as food or medicine since ancient times and recorded in "Shen Nong's Herbal Classic", "Compendium of Materia Medica" and "Traditional Chinese Medicine Dictionary" as herbal medicines with effects of clearing away heat and toxic materials,reducing edema,dispersing blood stasis,inhibiting bacteria,diminishing inflammation, detoxicating,expelling worms,treating allergy,improving memory and increasing coronary blood flow.However,most of ferns have not been subjected to chemical investigations except some of the species of Dryopteridaceae,Pteridaceae and Polypodiaceae.The chemical constituents of Angiopteris caudatiformis and Asplenium unilaterale,used as folk medicines in China,were investigated in this thesis.
The rhizome of Angiopteris caudatiformis has been used as medicine for a long time in Dai and Tujia nationalities in China for the treatment of infectious diseases, such as enteritis,diarrhea and pulmonary tuberculosis.The fibrous roots are also used as medicine for the treatment of cough caused by lung-heat,venomous snake bite, furuncle,and traumatic hemorrhage.However,no phytochemical and pharmacological researches have been reported on this species.
The chemical constituents of Angiopteris caudatiformis were investigated for the first time in this thesis and 21 compounds were isolated and identified by modern chromatography and spectral analysis,including 6 esters:angiopterlactone A(CP1), angiopterlactone B(CP2),osmundalactone(CP3),osmundalin(CP4),3,5- dihydroxy-γ-caprolactone(CPS),and ethyl thioglycolate(CP6);5 sterols:daucosterol (CP7),β-sitosterol(CPS),stigmasta-5,17(20)-dien-3-ol(CP9),stigmast-3-O-β-D-glucopyranoside (CP10),and 7-hydroxystigmast-4-en-3-one(CP11);4 sugars and glucosides:maltolβ-D-glucopyranoside(CP12),α-glucose(CP13),maltose(CP14) and ethyl-α-D-glucoside(CP15);2 fatty acids:palmic acid(CP16) and stearic acid (CP17);and 4 other compounds:malealdehyde(CP18),5-hydroxymethyl -2-furaldehyde(CP19),1-O-α-D-glucopyranosyl-(2S,3R,4E,8Z)-2-N-palmitoyloctadecasphinga -4,8-dienine(CP20) and 2,4-dihydroxypyrimidine(CP21).
Among them,CP1 and CP2 are new compounds possessing unique dual-lactone skeletons,the others except compound CP4 and CP8 are isolated for the first time from the genus Angiopteris,and all compounds are isolated from this species for the first time.
The antitumor and insect-antifeedant activities of the 5 lactones(CP1,CP2,CP3, CP4 and CP5) from Angiopteris caudatiformis were screened,with the result that CP1 exhibited good inhibiting effects for HeLa cells with IC_(50)=68.8μM.CP3(500 ppm) and CP4(1,000 ppm) showed moderate insect-antifeedant effects towards the larva of Plutella xylostella and Heliothis virescens.
The whole herb of Asplenium unilaterale is a Uygur medicine in China with the effects of clearing away heat and toxic materials,inducing astringency,expelling wind, removing damness,invigorating and regulating Qi.It has been used for the treatment of diarrhea.However,few researches have been reported on its chemical constituents. In this thesis,systematical studies have been reported on the chemical constituents of A.unilaterale,and 29 compounds were isolated and identified by applying modern chromatography and spectral analysis,including 5 megastigmane glucosides: (Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol(CPS4),icariside B_2(CPS5) and citroside A(CPS6),(6R,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside(CPS7), and 6S,9R-roseoside(CPSS);4 cumarins:6-methyl-2H-chromen-2-one(CPS9), 6,7-dihydroxy-2H-1-benzopyran-2-one(CPS10),gibepyrone D(CPS11);2 triterpenes:asplenic acid(CPS1) and lupan-3-one(CPS12);1 flavone:violanthin (CPS13);5 sterols:β-sitosterol(CPS14),daucosterol(CPS15),22,23-dimethylcholest-S-en-3-ol(CPS16),stigmasta-3,5-diene(CPS17) and asplenilol (CPS2);6 fatty alcohol or fatty acid compounds,1-tetratriacontanol(CPS18), 1-triacontanol(CPS19),carnaubic acid(CPS20),palmitic acid(CPS21),palmitic acid(CPS22),and methyl arachidate(CPS23);3 lactones:aspleniloide(CPS3), 5-hexylfuran-2(5H)-one(CPS24) and 4,5-dihydroxypentyl isobutyrate(CPS25);and 3 other compounds:tocopherylquinone(CPS26),2,4-(1H,3H)-pyrimidinedione (CPS27) and stachyose(CPS28).Among which,compounds CPS1,CPS2 and CPS3 were new and all of the compounds were isolated from the genus Asplenium for the first time.
In addition,research advances about the genera Angiopteris and Asplenium were summarized in this thesis,which provide evidence for the further research and application of plants from the two genera.
披针观音座莲(Angiopteris caudatiformis)为云南傣族及土族民间草药,使用历史悠久。其根茎作为傣药称为“季马”,主要用于治疗传染性疾病如肠炎,痢疾和肺结核等病症。其根茎和须根作为土家族民间草药可用于治疗肺热咳喘,毒蛇咬伤,疔疮疖肿及外伤出血等病症。但是,至今未见有对其化学和药理活性研究报道。
本文首次对披针观音座莲根茎的化学成分和生物活性进行了研究。从披针观音座莲根茎95%乙醇提取物中分离鉴定了21个化合物,包括:酯类化合物6个:观音座莲内酯A(angiopterlactone A,CP1),观音座莲内酯B(angiopterlactoneB,CP2),紫萁内酯(osmundalactone,CP3),紫萁内酯苷(osmundalin,CP4),3,5-二羟基-γ-己内酯(3,5-dihydroxy-γ-caprolactone,CP5),和巯基乙酸乙酯(ethylthioglycolate,CP6)。甾体类化合物5个:胡萝卜苷(daucosterol,CP7),β-谷甾醇(β-sitosterol,CP8),豆甾-5,17(20)-二烯-3-醇(stigmasta-5,17(20)-dien-3-ol,CP9),豆甾-3-O-β-D-吡喃葡萄糖苷(stigmast-3-O-β-D-glucopyranoside,CP10),和7-羟基豆甾-4烯-3-酮(7-hydroxystigmast-4-en-3-one,CP11)。糖及其苷类化合物4个:麦芽酚-β-D-吡喃葡萄糖甙(maltol-β-D-glucopyranoside,CP12),α-葡萄糖(α-glucose,CP13),麦芽糖(maltose,CP14),和乙基-α-D-葡萄糖苷(ethyl-α-D-glucoside,CP15)。脂肪酸类化合物2个:棕榈酸(palmic acid,CP16)和硬脂酸(stearic acid,CP17)。其他类4个:丁烯二醛(malealdehyde,CP18),5-羟甲基糠醛(5-hydroxy-methyl-2-furaldehyde,CP19),1-O-α-D-glucopyranosyl-(2S,3R,4E,8Z)-2-N-palmitoyloctade-casphinga-4,8-dienine(CP20),和2,4-二羟基嘧啶(2,4-dihydroxy-pyrimidine,CP21)。其中,CP1和CP2为2个具有双内酯骨架的新化合物,除化合物CP4和CP8外,其余化合物均为首次从该属植物中分离得到,所有化合物均为首次从该植物中分离得到。
对披针观音座莲中分离得到的5个内酯类化合物进行了体外抗肿瘤活性和昆虫拒食活性的初筛,结果显示新化合物观音座莲内酯A(CP1)对宫颈癌传代(HeLa cell)细胞具有细胞毒活性,其IC_(50)值为68.8μM。化合物紫其内酯(CP3),紫萁内酯苷(CP4)在浓度分别为500ppm和1000ppm时,对两种受试幼虫Plutella xylostella和Heliothis virescens显示拒食活性。
半边铁角蕨(Asplenium unilaterale)为维吾尔族民间草药,具有清热解毒、止血等功效。利用多种色谱技术分别对披针观音座莲和半边铁角蕨的化学成分进行了系统的分离,从半边铁角蕨全草的甲醇提取物中分离鉴定了28个化合物,包括:紫罗兰酮类5个:(Z)-4-(2,6,6-三甲基亚环己-2-烯基)丁-2-醇((Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol,CPS4),淫羊藿次苷Ⅱ(icariside B_2,CPS5),citroside A(CPS6),6R,9R-3-酮-α-紫罗兰醇-9-O-β-D-吡喃葡萄糖苷((6R,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside,CPS7),和(6S,9R)-6-羟基-3-酮-α-紫罗兰醇-9-O-β-D-葡萄糖苷((6S,9R)-roseoside,CPS8)。香豆素类3个:6-甲基-2H-香豆-2-酮(6-methyl-2H-chromen-2-one,CPS9),6,7-二羟基-香豆素(6,7-dihydroxy-2H-1-benzopyran-2-one,CPS10),和gibepyrone D(CPS11)。三萜类2个:铁角蕨酸(asplenic acid,CPS1),和羽扇豆烷-3-酮(lupan-3-one,CPS12)。黄酮类1个:芹菜素-6-C-β-D-吡喃葡萄糖-7-C-6-鼠李糖吡喃糖苷(violanthin,CPS13)。甾醇类5个:β-谷甾醇(β-sitosterol,CPS14),胡萝卜苷(daucosterol,CPS15),22,23-二甲基胆甾-S-烯-3-醇(22,23-dimethylcholest-S-en-3-ol,CPS16),豆甾-3,5-二烯(stigmasta-3,5-diene,CPS17),和铁角蕨甾醇(asplenilol,CPS2)。脂肪族类6个:正三十四醇(1-tetratriacontanol,CPS18),正三十二醇(1-laccerol,CPS19),正二十四酸(carnaubic acid,CPS20),棕榈酸(palmitic acid,CPS21),硬脂酸(palmiticacid,CPS22),和花生酸甲酯(methyl arachidate,CPS23)。酯类3个:铁角蕨内酯(aspleniloide,CPS3),5-己烷呋喃-2(5H)-(5-hexylfuran-2(5H)-one,CPS24),和4,5-二羟基戊-异丁酯(4,5-dihydroxypentyl-isobutyrate,CPS25)。其他类3个:托可醌(tocopherylquinone,CPS26),2,4(1H,3H)-嘧啶二酮(2,4-(1H,3H)-pyrimidinedione,CPS27),和水苏糖(stachyose,CPS28)。其中,CPS1,CPS2和CPS3为新化合物,所有化合物均为首次从该属植物中分离得到。
本论文还对观音座莲属植物和铁角蕨属植物的国内外研究进展进行了归纳总结,为这两属蕨类植物资源的进一步研究与开发提供参考。
Ferns widely distributed in various areas throughout the world,particularly abundant in tropical and subtropical zones,belong to the oldest group of higher plants. Among them,more than 2,600 species exist in China,some of them are used as food or medicine since ancient times and recorded in "Shen Nong's Herbal Classic", "Compendium of Materia Medica" and "Traditional Chinese Medicine Dictionary" as herbal medicines with effects of clearing away heat and toxic materials,reducing edema,dispersing blood stasis,inhibiting bacteria,diminishing inflammation, detoxicating,expelling worms,treating allergy,improving memory and increasing coronary blood flow.However,most of ferns have not been subjected to chemical investigations except some of the species of Dryopteridaceae,Pteridaceae and Polypodiaceae.The chemical constituents of Angiopteris caudatiformis and Asplenium unilaterale,used as folk medicines in China,were investigated in this thesis.
The rhizome of Angiopteris caudatiformis has been used as medicine for a long time in Dai and Tujia nationalities in China for the treatment of infectious diseases, such as enteritis,diarrhea and pulmonary tuberculosis.The fibrous roots are also used as medicine for the treatment of cough caused by lung-heat,venomous snake bite, furuncle,and traumatic hemorrhage.However,no phytochemical and pharmacological researches have been reported on this species.
The chemical constituents of Angiopteris caudatiformis were investigated for the first time in this thesis and 21 compounds were isolated and identified by modern chromatography and spectral analysis,including 6 esters:angiopterlactone A(CP1), angiopterlactone B(CP2),osmundalactone(CP3),osmundalin(CP4),3,5- dihydroxy-γ-caprolactone(CPS),and ethyl thioglycolate(CP6);5 sterols:daucosterol (CP7),β-sitosterol(CPS),stigmasta-5,17(20)-dien-3-ol(CP9),stigmast-3-O-β-D-glucopyranoside (CP10),and 7-hydroxystigmast-4-en-3-one(CP11);4 sugars and glucosides:maltolβ-D-glucopyranoside(CP12),α-glucose(CP13),maltose(CP14) and ethyl-α-D-glucoside(CP15);2 fatty acids:palmic acid(CP16) and stearic acid (CP17);and 4 other compounds:malealdehyde(CP18),5-hydroxymethyl -2-furaldehyde(CP19),1-O-α-D-glucopyranosyl-(2S,3R,4E,8Z)-2-N-palmitoyloctadecasphinga -4,8-dienine(CP20) and 2,4-dihydroxypyrimidine(CP21).
Among them,CP1 and CP2 are new compounds possessing unique dual-lactone skeletons,the others except compound CP4 and CP8 are isolated for the first time from the genus Angiopteris,and all compounds are isolated from this species for the first time.
The antitumor and insect-antifeedant activities of the 5 lactones(CP1,CP2,CP3, CP4 and CP5) from Angiopteris caudatiformis were screened,with the result that CP1 exhibited good inhibiting effects for HeLa cells with IC_(50)=68.8μM.CP3(500 ppm) and CP4(1,000 ppm) showed moderate insect-antifeedant effects towards the larva of Plutella xylostella and Heliothis virescens.
The whole herb of Asplenium unilaterale is a Uygur medicine in China with the effects of clearing away heat and toxic materials,inducing astringency,expelling wind, removing damness,invigorating and regulating Qi.It has been used for the treatment of diarrhea.However,few researches have been reported on its chemical constituents. In this thesis,systematical studies have been reported on the chemical constituents of A.unilaterale,and 29 compounds were isolated and identified by applying modern chromatography and spectral analysis,including 5 megastigmane glucosides: (Z)-4-(2,6,6-trimethylcyclohex-2-enylidene)butan-2-ol(CPS4),icariside B_2(CPS5) and citroside A(CPS6),(6R,9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside(CPS7), and 6S,9R-roseoside(CPSS);4 cumarins:6-methyl-2H-chromen-2-one(CPS9), 6,7-dihydroxy-2H-1-benzopyran-2-one(CPS10),gibepyrone D(CPS11);2 triterpenes:asplenic acid(CPS1) and lupan-3-one(CPS12);1 flavone:violanthin (CPS13);5 sterols:β-sitosterol(CPS14),daucosterol(CPS15),22,23-dimethylcholest-S-en-3-ol(CPS16),stigmasta-3,5-diene(CPS17) and asplenilol (CPS2);6 fatty alcohol or fatty acid compounds,1-tetratriacontanol(CPS18), 1-triacontanol(CPS19),carnaubic acid(CPS20),palmitic acid(CPS21),palmitic acid(CPS22),and methyl arachidate(CPS23);3 lactones:aspleniloide(CPS3), 5-hexylfuran-2(5H)-one(CPS24) and 4,5-dihydroxypentyl isobutyrate(CPS25);and 3 other compounds:tocopherylquinone(CPS26),2,4-(1H,3H)-pyrimidinedione (CPS27) and stachyose(CPS28).Among which,compounds CPS1,CPS2 and CPS3 were new and all of the compounds were isolated from the genus Asplenium for the first time.
In addition,research advances about the genera Angiopteris and Asplenium were summarized in this thesis,which provide evidence for the further research and application of plants from the two genera.
引文
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