麻黄根及羊齿天门冬化学成分研究
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摘要
中药是我国人民数千年来与疾病斗争的结晶,其疗效在中医药的临床实践中不断得到验证,在治疗肿瘤、肝纤维化、免疫系统等重大疾病及疑难杂症方面显示出独特的效果。植物化学成分是天然药物防病治病的物质基础,天然药物的发展在很大程度上取决于新的活性先导化合物的发现与优化。选用中药材作为原料资源,从中提取、分离和鉴定有活性的单体化合物,经过广泛的药理筛选开发成新药,可以大大缩短新药开发周期,降低成本,克服了合成上设计的盲目性和毒副作用较大的缺点,是现代医学研制高效低毒创新药物最佳方式。
麻黄根为麻黄科(Ephedtaceae)麻黄属(Ephedra)植物草麻黄(Ephedra sinica Stapf)的干燥根及根茎,主要分布于我国的吉林、辽宁、内蒙古等省区,生长在沙丘、干草原、丘陵山地、荒滩等干燥地区。据药典记载,麻黄以干燥草质茎入药,具有发汗平喘宣肺之功效,麻黄根亦可入药,性平、味甘,功能止汗。迄今,有关该植物化学成分研究主要对地上部分报道较多,而对地下部分研究较少。其活性研究更相当薄弱,严重遏制了麻黄根的开发利用。为了充分利用我国丰富的麻黄资源,进一步开发麻黄新的药用价值,寻找其新的活性成分,本论文选取麻黄的地下根作为研究对象,对其化学成分进行了系统的研究,希望为发现新的天然药物奠定良好的资源、理论及技术基础。
本论文对麻黄根化学成分进行了系统的研究,从麻黄根的乙酸乙酯部位中分离出42个化合物,通过理化性质分析和现代波谱技术解析鉴定了其中37个化合物的结构,其中新化合物9个,另有15个化合物为首次从该属植物中分离得到。通过对部分化合物进行体外抗肿瘤活性筛选,得到一个具有较强体外抗肿瘤活性的化合物。
本论文还对百合科(Liliaceae)天门冬属(Asparagus)植物中具有较强抗肿瘤活性的羊齿天门冬(Asparagus filicinus Buchu.- Ham)进行了深入的化学成分研究。利用现代色谱技术和波谱技术,我们从羊齿天门冬的干燥块根中分离鉴定化合物37个,其中5个化合物为首次从天门冬属植物中分离得到,15个化合物为首次从羊齿天门冬植物中分离得到。本研究为阐明该植物的抗肿瘤机制提供化学依据。
此外,我们对麻黄属植物和天门冬属植物的化学成分和生物活性研究概况进行了综述,这对于合理开发利用这两属药用植物资源提供了依据。
The roots of Ephedra sinica Stapf and Asparagus filicinus Buch.-Ham were selected for phytochemical and bioactive investigations. Main results were obtained as follows:
Thirty-seven compounds have been isolated from the root of Ephedra sinica Stapf on the basis of modern isolation chromatography methods and were elucidated by many kinds of spectroscopic and chemical evidences. These compounds included twelve biflavones, eleven flavonoids, three terpenoids, one lignan, as well as ten miscellanrous compounds, among them nine compounds were identified as new and fifteen were first isolated from the genus. New compounds were ephedrannin B (1), mahuannin E (3), mahuannin F (7), mahuannin G (8), mahuannin H (9), mahuannin I (10), mahuannin J (11), mahuannin K (12), ephedrate A (29). Other known compounds were ephedrannin A (2), mahuannin D (4), mahuannin A (5), mahuannin B (6), apigenin (13), quercetin (14), kaempferol (15), dihydroquercetin (16), 3-hydroxynaringenin (17), 3′,4′,5,7-tetrahydroxy flavanone (18), naringenin (19), (+)-catechin (20), (-)-epi-catechin (21), afzelechin (22), (-)-epi-afzelechin (23), (?)-α-terpineol-8-O-β-D- gluco pyranoside (24), (+)-α-terpineol-8-O-β-D-glucopyranoside (25), geranyl -β-D-glucopyranoside (26), sesquipinsapol B(27), (10E, 9S, 12S, 13S)- trihydroxy-10-octadecenoate (28), (E)-hexadecyl-ferulate B(30), 3-(hexadecyloxy)propane-1,2-diol (31), bis(2-ethylhexyl) phthalate (32), vanillic acid (33), protocatechuic acid (34), ferulic acid (35), daucosterol (36) andβ-sitosterol (37). The cytotoxicity of biflavones was tested in the HeLa (human ovarian cancer), SGC-7901 (human stomach cancer), and HepG2 (human liver cancer) using the MTT method. Ephedrannin B (1) showed strong cytotoxicity against HeLa, SGC-7901, and HepG2cells with IC50 values of 8.5, 10.0, and 10.2μg/mL, respectively.
Asparagus filicinus Buch.-Ham was also investigated for chemical constituents. From the underground parts of this plant, thirty-seven compounds were isolated and identified including eight steroidal saponins , seven ecdysones, five lignans, three acetylene derivatives, one alkaloid, as well as twelve miscellaneous compounds, among which fifteen compounds were isolated from this plants for the first time. Based on spectral analyses and comparison with reported in the literatures, the isolates were characterized as follows: aspafilioside A (A1), asparosede A (A2), filiasparoside C (A3), aspafiliosede B (A4), asparagusin A (A5), 22-methoxy ASP-IV (A6), aspafiliosede C(A7), aspafiliosede D (A8), calonysterone (A9), 5-deoxykaladasterone (A10), 25-hydroxy dacryhainansterone (A11), stachysterone C (A12), stachysterone B (A13), ecdysone (A14),β-ecdysterone (A15), 20-hydroxyecdysine-20,22- monocetonide (A16), 3′-methoxynyasin (A17), (+)-nyasol (A18), (-)4′-O-methyl-nyasol (A19), iso-agatharesinol (A20), gobicusin A (A21), 4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl]phenol (A22), 1-methoxy-2- hydroxy-4-[5-(4-hydroxy phenoxy)-3-penten-1-ynyl]phenol (A23), gobicusin B (A24), 1-O-p-coumaroyl-3-O-feruloylglycerol (A25), 1,3-di- O-feruloylglycerol (A26), 9,12-Octadecadienoic acid (9Z,12Z)-2- [(1-oxooctadecyl) oxy]-1,3- propanediyl ester (A27), n-hexadecane acid monoglyceride (A28), lycoperodine-1 (A29), syringic acid (A30), 4-hydroxybenzoic acid (A31), fumalic acid (A32), caffeic acid (A33), trans-coniferyl alcohol (A34), vanillic acid (A35) , daucosterol (36),β-sitosterol (37). Pharmacological activity of these compounds is still in testing.
In addition, the thesis also reviewed the phytochemical and biological investigations on the genera of ephedra and asparagus.
麻黄根为麻黄科(Ephedtaceae)麻黄属(Ephedra)植物草麻黄(Ephedra sinica Stapf)的干燥根及根茎,主要分布于我国的吉林、辽宁、内蒙古等省区,生长在沙丘、干草原、丘陵山地、荒滩等干燥地区。据药典记载,麻黄以干燥草质茎入药,具有发汗平喘宣肺之功效,麻黄根亦可入药,性平、味甘,功能止汗。迄今,有关该植物化学成分研究主要对地上部分报道较多,而对地下部分研究较少。其活性研究更相当薄弱,严重遏制了麻黄根的开发利用。为了充分利用我国丰富的麻黄资源,进一步开发麻黄新的药用价值,寻找其新的活性成分,本论文选取麻黄的地下根作为研究对象,对其化学成分进行了系统的研究,希望为发现新的天然药物奠定良好的资源、理论及技术基础。
本论文对麻黄根化学成分进行了系统的研究,从麻黄根的乙酸乙酯部位中分离出42个化合物,通过理化性质分析和现代波谱技术解析鉴定了其中37个化合物的结构,其中新化合物9个,另有15个化合物为首次从该属植物中分离得到。通过对部分化合物进行体外抗肿瘤活性筛选,得到一个具有较强体外抗肿瘤活性的化合物。
本论文还对百合科(Liliaceae)天门冬属(Asparagus)植物中具有较强抗肿瘤活性的羊齿天门冬(Asparagus filicinus Buchu.- Ham)进行了深入的化学成分研究。利用现代色谱技术和波谱技术,我们从羊齿天门冬的干燥块根中分离鉴定化合物37个,其中5个化合物为首次从天门冬属植物中分离得到,15个化合物为首次从羊齿天门冬植物中分离得到。本研究为阐明该植物的抗肿瘤机制提供化学依据。
此外,我们对麻黄属植物和天门冬属植物的化学成分和生物活性研究概况进行了综述,这对于合理开发利用这两属药用植物资源提供了依据。
The roots of Ephedra sinica Stapf and Asparagus filicinus Buch.-Ham were selected for phytochemical and bioactive investigations. Main results were obtained as follows:
Thirty-seven compounds have been isolated from the root of Ephedra sinica Stapf on the basis of modern isolation chromatography methods and were elucidated by many kinds of spectroscopic and chemical evidences. These compounds included twelve biflavones, eleven flavonoids, three terpenoids, one lignan, as well as ten miscellanrous compounds, among them nine compounds were identified as new and fifteen were first isolated from the genus. New compounds were ephedrannin B (1), mahuannin E (3), mahuannin F (7), mahuannin G (8), mahuannin H (9), mahuannin I (10), mahuannin J (11), mahuannin K (12), ephedrate A (29). Other known compounds were ephedrannin A (2), mahuannin D (4), mahuannin A (5), mahuannin B (6), apigenin (13), quercetin (14), kaempferol (15), dihydroquercetin (16), 3-hydroxynaringenin (17), 3′,4′,5,7-tetrahydroxy flavanone (18), naringenin (19), (+)-catechin (20), (-)-epi-catechin (21), afzelechin (22), (-)-epi-afzelechin (23), (?)-α-terpineol-8-O-β-D- gluco pyranoside (24), (+)-α-terpineol-8-O-β-D-glucopyranoside (25), geranyl -β-D-glucopyranoside (26), sesquipinsapol B(27), (10E, 9S, 12S, 13S)- trihydroxy-10-octadecenoate (28), (E)-hexadecyl-ferulate B(30), 3-(hexadecyloxy)propane-1,2-diol (31), bis(2-ethylhexyl) phthalate (32), vanillic acid (33), protocatechuic acid (34), ferulic acid (35), daucosterol (36) andβ-sitosterol (37). The cytotoxicity of biflavones was tested in the HeLa (human ovarian cancer), SGC-7901 (human stomach cancer), and HepG2 (human liver cancer) using the MTT method. Ephedrannin B (1) showed strong cytotoxicity against HeLa, SGC-7901, and HepG2cells with IC50 values of 8.5, 10.0, and 10.2μg/mL, respectively.
Asparagus filicinus Buch.-Ham was also investigated for chemical constituents. From the underground parts of this plant, thirty-seven compounds were isolated and identified including eight steroidal saponins , seven ecdysones, five lignans, three acetylene derivatives, one alkaloid, as well as twelve miscellaneous compounds, among which fifteen compounds were isolated from this plants for the first time. Based on spectral analyses and comparison with reported in the literatures, the isolates were characterized as follows: aspafilioside A (A1), asparosede A (A2), filiasparoside C (A3), aspafiliosede B (A4), asparagusin A (A5), 22-methoxy ASP-IV (A6), aspafiliosede C(A7), aspafiliosede D (A8), calonysterone (A9), 5-deoxykaladasterone (A10), 25-hydroxy dacryhainansterone (A11), stachysterone C (A12), stachysterone B (A13), ecdysone (A14),β-ecdysterone (A15), 20-hydroxyecdysine-20,22- monocetonide (A16), 3′-methoxynyasin (A17), (+)-nyasol (A18), (-)4′-O-methyl-nyasol (A19), iso-agatharesinol (A20), gobicusin A (A21), 4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl]phenol (A22), 1-methoxy-2- hydroxy-4-[5-(4-hydroxy phenoxy)-3-penten-1-ynyl]phenol (A23), gobicusin B (A24), 1-O-p-coumaroyl-3-O-feruloylglycerol (A25), 1,3-di- O-feruloylglycerol (A26), 9,12-Octadecadienoic acid (9Z,12Z)-2- [(1-oxooctadecyl) oxy]-1,3- propanediyl ester (A27), n-hexadecane acid monoglyceride (A28), lycoperodine-1 (A29), syringic acid (A30), 4-hydroxybenzoic acid (A31), fumalic acid (A32), caffeic acid (A33), trans-coniferyl alcohol (A34), vanillic acid (A35) , daucosterol (36),β-sitosterol (37). Pharmacological activity of these compounds is still in testing.
In addition, the thesis also reviewed the phytochemical and biological investigations on the genera of ephedra and asparagus.
引文
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