山豆根和苦参化学成分的比较研究
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摘要
山豆根和苦参均为豆科槐属植物来源的常用中药,其中山豆根为越南槐
Sophora tonkinensis Gapnep. 的干燥根及根茎,苦参为苦参 Sophora flavescens
Ait.的干燥根。两者药用部位相仿,而且成分相似,都含有喹诺里西啶类生物
碱、异戊烯基类黄酮和齐墩果烯型三萜等成分,但两种药材的临床应用却有
明显不同,山豆根主要用于治疗咽喉疾病,而苦参主要用于皮肤病和妇科疾
病的治疗。另外,在药材的质量标准方面,山豆根和苦参都以苦参碱型生物
碱(苦参碱、氧化苦参碱或槐定碱)作为定性指标缺乏专属性,且苦参药材
仅以含量相对较小的苦参碱为质控指标,不尽合理。为了阐明山豆根和苦参
药材的化学组成差异,以完善山豆根和苦参药材的质量标准并为两者药效物
质基础的阐明奠定基础,同时也为了寻找新的抗病毒活性成分,以更好地利
用槐属药用植物资源,本文采用天然药化和分析化学等手段对山豆根和苦参
的化学成分进行了系统地比较研究,建立了其有效部位的 HPLC 指纹图谱,
并对不同来源药材的多种有效成分进行了含量测定,同时结合国家“九五”
攻关课题的要求对山豆根的化学对照品进行了研究。
一、山豆根和苦参的化学成分
1、 山豆根的化学成分:采用柱层析和制备薄层色谱等方法从山豆根(Sophora
tonkinensis Gapnep.)的生物碱部位分离得到 10 个化合物,从其乙醇提取
物的乙醚萃取部位分离得到 22 个化合物。经波谱学分析以及与对照品比
较的方法,鉴定了其中的 30 个化合物,它们分别是:生物碱类成分(+)-
苦参碱(T1)、(+)-氧化苦参碱(T2)、(+)-槐花醇(T3)、(-)-14β-羟基苦
参碱(T4)、(-)-14β-羟基氧化苦参碱(T5)、(-)-槐果碱(T6)、(-)-5α-羟
基槐果碱(T7)、(-)-金雀花碱(T8)和 (-)-N-甲基金雀花碱(T9),黄酮
类成分山豆根色满二氢黄酮 A(T10)、山豆根色满二氢黄酮 B(T11)、山
豆根色满二氢黄酮 C(T12)、山豆根色满二氢黄酮 D(T13)、山豆根色满
查耳酮 B(T14)、山豆根色满查耳酮 A(T15)、山豆根色满查耳酮 C(T16)、
芒柄花素(T17)、8-甲雷杜辛(T18)和(-)-三叶豆紫檀苷(T19),三萜类
i
成分(+)-羽扇豆醇(T20)和(+)-槐花二醇(T21),小分子酚性成分番石榴
酸乙酯(T22)、麦芽酚(T23)、香草酸(T24)、对羟基苯甲酸(T25)和
咖啡酸十二醇酯(T26)以及大黄素甲醚(T27)、大黄素(T28)、
flemichapparin(T29)和β-谷甾醇(T30)。其中化合物 T5、T10、T11、
T12、T13、T14 和 T16 为新化合物,化合物 T22、T23、T27 和 T28 为首
次由槐属植物中分离得到,化合物 T17、T18、T24、T25 和 T29 为首次
由该种植物中分离得到。
2、 苦参的化学成分:采用柱层析和制备薄层色谱等方法从苦参(Sophora
flavescens Ait.)的生物碱部位分离得到 11 个化合物,从其乙醇提取物的
乙醚萃取部位分离得到 22 个化合物。经波谱学分析,结合单晶 X-衍射实
验,鉴定了其中的 29 个化合物,它们分别是:生物碱类成分(+)-氧化苦参
碱(F1)、(+)-别苦参碱(F2)、(-)-9α-羟基苦参碱(F3)、(-)-槐果碱(F4)、
(+)-氧化槐果碱(F5)、(+)-莱蔓碱(F6)、(-)-13,14-去氢槐定碱(F7)、
(-)-9α-羟基槐果碱(F8)、(+)-12α-羟基槐果碱(F9)和(-)-臭豆碱(F10),
黄酮类成分苦参色满二氢黄酮 B(F11)、苦参色满二氢黄酮 C(F12)、苦
参色满二氢黄酮 D(F13)、苦参色满二氢黄酮 A(F14)、苦参色满黄酮 A
(F15)、苦参色满黄酮 B(F16)、苦参色满黄酮 C(F17)、5-去羟山柰素
(F18)、7,4′-二羟基-3′-甲氧基异黄酮(F19)、毛蕊异黄酮(F20)、鹰
嘴豆素甲(F21)、大豆素(F22)和芒柄花素(F23),三萜类成分大豆皂
醇 B(F24),小分子酚性成分番石榴酸二乙酯(F25)、对羟基苯甲酸乙酯
(F26)和麦芽酚(F27)以及大黄酚(F28)和β-谷甾醇(F29)。其中化
合物 F9、F11、F12、F13、F15、F16 和 F17 为新化合物,化合物 F25、
F27 和 F28 为首次由槐属植物中分离得到,化合物 F18、F19、F20、F21、
F22、F24 和 F26 为首次由该种植物中分离得到。
3、 抗病毒活性试验:对实验中分离得到的生物碱类成分进行抗乙肝病毒活性
筛选,结果表明苦参碱、氧化苦参碱、槐花醇、槐果碱、氧化槐果碱、莱
蔓碱、9α-羟基苦参碱、13,14-去氢槐定碱、12α-羟基槐果碱和金雀花碱
在 0.2μmol/mL 时,臭豆碱在 0.4μmol/mL 时对 HBsAg 的抑制率高于阳性
对照拉米呋啶(1.0μmol/mL 时抑制率为 29.6%),其中槐果碱、莱蔓碱和
13,14-去氢槐定碱抑制作用较明显,在 0.2μmol/mL 时抑制率均大于 50%。
槐果碱在 0.2μmol/mL 时对 HBeAg 亦有一定的抑制作用,抑制率为 34.6%,
和拉米呋啶相当(1.0μmol/mL 时抑制率为 35.4%)。槐果碱、氧化槐果碱、
ii
莱蔓碱和 13,14-去氢槐定碱对 HBsAg 和 HBeAg 的抑制率均较目前临床
用于治疗乙肝疾病的药物苦参碱和氧化苦参碱的相应抑制率高,值得深入
研究。
4、 部分异戊烯基黄酮类化合物的定性检测:采用 HPLC-DAD-MS 的方法对
实验中分离得到的部分异戊烯基黄酮类化合物进行了定性检测,发现本人
分离得到的具有 2,2-二甲基苯并二氢吡喃环取代的黄酮类?
“Shandougen” and “Kushen” are the commonly used traditional Chinese
medicines derived from Sophora plants. “Shandougen” is the dried roots and
rhizomes of Sophora tonkinensis Gapnep. and “Kushen” is the dried roots of
Sophora flavescens Ait.. The two crude drugs are so similar in the chemical
constituents that they were both stated to contain quinolizidine alkaloids,
prenylated flavonoids and oleanene triterpenoids. But their clinical applications
are quite different, “Shandougen” is mainly used to treat acute pharyngolaryngeal
infections and sore throat, while “Kushen” is mostly used to treat the skin diseases
and the gynaecological diseases such as eczema, dermatitis and colpitis. In the
Chinese Pharmacopoeia (CP), the TLC tests given for the identification of
“Shandougen” and “Kushen” lack specificity, in which the alkaloids matrine,
oxymatrine and sophoridine are chosen as the qualitative markers. And in CP, it
seems unsuitable to assess the quality of “Kushen” by determining the content of
the minor compound matrine, the content of which is much lower than those of the
other two active constituents oxymatrine and oxysophocarpine in this drug. And
the discrepancy between the theory and the practice of traditional Chinese
medicine requires to assess the quality of the crude drugs with multiple indicators.
Therefore, in order to specify “Shandougen” from “Kushen” effectively, to
assess the quality of these two crude drugs comprehensively, to supply useful
information for the further understanding on the relationships between the
chemical constituents and the unique medicinal properties claimed for
“Shandougen” and “Kushen”, and also to search for antiviral agents from natural
products as well, the chemical constituents of “Shandougen” and “Kushen” were
investigated systemically. Their alkaloid and flavonoid compositions were
compared comprehensively by HPLC fingerprinting, and the contents of several
active quinolizidine alkaloids in the commercial drugs from different sources were
determined by HPCE method. In addition, a study on the chemical reference
substances of Sophora tonkinensis was also carried out.
vii
Part One: The Chemical Constituents of S. tonkinensis and S. flavescens
Ten compounds were isolated from the acid water-soluble part and
twenty-two compounds were isolated from the ether-soluble fraction of the ethanol
extracts of the roots and rhizomes of S. tonkinensis, respectively, by repeated
column chromatography and preparative TLC method. The structures of thirty
compounds were elucidated by spectroscopic methods as follows: the alkaloids
(+)-matrine (T1), (+)-oxymatrine (T2), (+)-sophoranol (T3), (-)-14β-hydroxymatr-
ine (T4), (-)-14β-hydroxyoxymatrine (T5), (-)-sophocarpine (T6),
(-)-5α-hydroxysophocarpine (T7), (-)-cytisine (T8), (-)-N-methylcytisine (T9); the
flavonoids sophoratonkinochromane A (T10), sophoratonkinochromane B (T11),
sophoratonkinochromane C (T12), sophoratonkinochromane D (T13),
sophoratonkidochromane B (T14), sophoratonkidochromane A (T15),
sophoratonkidochromane C (T16), formononetin (T17), 8-methylretusin (T18),
(-)-trifolirhizin (T19); the triterpenoids (+)-lupeol (T20), (+)-sophoradiol (T21);
the phenolic components piscidic acid monoethyl ester (T22), maltol (T23),
venillic acid (T24), p-hydroxybenzoic acid (T25), docosyl caffeate (T26); the other
compounds physcion (T27), emodin (T28), flemichapparin (T29) and β-sitosterol
(30). Among them, T5, T10, T11, T12, T13, T14 and T16 were new compounds,
T22, T23, T27 and T28 were isolated from genus Sophora and T17, T18, T24,
T25 and T29 were isolated from this species for the first time.
Eleven compounds were isolated from the acid water-soluble part and
twenty-two compounds were isolated from the ether-soluble fraction of the ethanol
extracts of the roots of S. flavescens, respectively, by repeated column
chromatography a
Sophora tonkinensis Gapnep. 的干燥根及根茎,苦参为苦参 Sophora flavescens
Ait.的干燥根。两者药用部位相仿,而且成分相似,都含有喹诺里西啶类生物
碱、异戊烯基类黄酮和齐墩果烯型三萜等成分,但两种药材的临床应用却有
明显不同,山豆根主要用于治疗咽喉疾病,而苦参主要用于皮肤病和妇科疾
病的治疗。另外,在药材的质量标准方面,山豆根和苦参都以苦参碱型生物
碱(苦参碱、氧化苦参碱或槐定碱)作为定性指标缺乏专属性,且苦参药材
仅以含量相对较小的苦参碱为质控指标,不尽合理。为了阐明山豆根和苦参
药材的化学组成差异,以完善山豆根和苦参药材的质量标准并为两者药效物
质基础的阐明奠定基础,同时也为了寻找新的抗病毒活性成分,以更好地利
用槐属药用植物资源,本文采用天然药化和分析化学等手段对山豆根和苦参
的化学成分进行了系统地比较研究,建立了其有效部位的 HPLC 指纹图谱,
并对不同来源药材的多种有效成分进行了含量测定,同时结合国家“九五”
攻关课题的要求对山豆根的化学对照品进行了研究。
一、山豆根和苦参的化学成分
1、 山豆根的化学成分:采用柱层析和制备薄层色谱等方法从山豆根(Sophora
tonkinensis Gapnep.)的生物碱部位分离得到 10 个化合物,从其乙醇提取
物的乙醚萃取部位分离得到 22 个化合物。经波谱学分析以及与对照品比
较的方法,鉴定了其中的 30 个化合物,它们分别是:生物碱类成分(+)-
苦参碱(T1)、(+)-氧化苦参碱(T2)、(+)-槐花醇(T3)、(-)-14β-羟基苦
参碱(T4)、(-)-14β-羟基氧化苦参碱(T5)、(-)-槐果碱(T6)、(-)-5α-羟
基槐果碱(T7)、(-)-金雀花碱(T8)和 (-)-N-甲基金雀花碱(T9),黄酮
类成分山豆根色满二氢黄酮 A(T10)、山豆根色满二氢黄酮 B(T11)、山
豆根色满二氢黄酮 C(T12)、山豆根色满二氢黄酮 D(T13)、山豆根色满
查耳酮 B(T14)、山豆根色满查耳酮 A(T15)、山豆根色满查耳酮 C(T16)、
芒柄花素(T17)、8-甲雷杜辛(T18)和(-)-三叶豆紫檀苷(T19),三萜类
i
成分(+)-羽扇豆醇(T20)和(+)-槐花二醇(T21),小分子酚性成分番石榴
酸乙酯(T22)、麦芽酚(T23)、香草酸(T24)、对羟基苯甲酸(T25)和
咖啡酸十二醇酯(T26)以及大黄素甲醚(T27)、大黄素(T28)、
flemichapparin(T29)和β-谷甾醇(T30)。其中化合物 T5、T10、T11、
T12、T13、T14 和 T16 为新化合物,化合物 T22、T23、T27 和 T28 为首
次由槐属植物中分离得到,化合物 T17、T18、T24、T25 和 T29 为首次
由该种植物中分离得到。
2、 苦参的化学成分:采用柱层析和制备薄层色谱等方法从苦参(Sophora
flavescens Ait.)的生物碱部位分离得到 11 个化合物,从其乙醇提取物的
乙醚萃取部位分离得到 22 个化合物。经波谱学分析,结合单晶 X-衍射实
验,鉴定了其中的 29 个化合物,它们分别是:生物碱类成分(+)-氧化苦参
碱(F1)、(+)-别苦参碱(F2)、(-)-9α-羟基苦参碱(F3)、(-)-槐果碱(F4)、
(+)-氧化槐果碱(F5)、(+)-莱蔓碱(F6)、(-)-13,14-去氢槐定碱(F7)、
(-)-9α-羟基槐果碱(F8)、(+)-12α-羟基槐果碱(F9)和(-)-臭豆碱(F10),
黄酮类成分苦参色满二氢黄酮 B(F11)、苦参色满二氢黄酮 C(F12)、苦
参色满二氢黄酮 D(F13)、苦参色满二氢黄酮 A(F14)、苦参色满黄酮 A
(F15)、苦参色满黄酮 B(F16)、苦参色满黄酮 C(F17)、5-去羟山柰素
(F18)、7,4′-二羟基-3′-甲氧基异黄酮(F19)、毛蕊异黄酮(F20)、鹰
嘴豆素甲(F21)、大豆素(F22)和芒柄花素(F23),三萜类成分大豆皂
醇 B(F24),小分子酚性成分番石榴酸二乙酯(F25)、对羟基苯甲酸乙酯
(F26)和麦芽酚(F27)以及大黄酚(F28)和β-谷甾醇(F29)。其中化
合物 F9、F11、F12、F13、F15、F16 和 F17 为新化合物,化合物 F25、
F27 和 F28 为首次由槐属植物中分离得到,化合物 F18、F19、F20、F21、
F22、F24 和 F26 为首次由该种植物中分离得到。
3、 抗病毒活性试验:对实验中分离得到的生物碱类成分进行抗乙肝病毒活性
筛选,结果表明苦参碱、氧化苦参碱、槐花醇、槐果碱、氧化槐果碱、莱
蔓碱、9α-羟基苦参碱、13,14-去氢槐定碱、12α-羟基槐果碱和金雀花碱
在 0.2μmol/mL 时,臭豆碱在 0.4μmol/mL 时对 HBsAg 的抑制率高于阳性
对照拉米呋啶(1.0μmol/mL 时抑制率为 29.6%),其中槐果碱、莱蔓碱和
13,14-去氢槐定碱抑制作用较明显,在 0.2μmol/mL 时抑制率均大于 50%。
槐果碱在 0.2μmol/mL 时对 HBeAg 亦有一定的抑制作用,抑制率为 34.6%,
和拉米呋啶相当(1.0μmol/mL 时抑制率为 35.4%)。槐果碱、氧化槐果碱、
ii
莱蔓碱和 13,14-去氢槐定碱对 HBsAg 和 HBeAg 的抑制率均较目前临床
用于治疗乙肝疾病的药物苦参碱和氧化苦参碱的相应抑制率高,值得深入
研究。
4、 部分异戊烯基黄酮类化合物的定性检测:采用 HPLC-DAD-MS 的方法对
实验中分离得到的部分异戊烯基黄酮类化合物进行了定性检测,发现本人
分离得到的具有 2,2-二甲基苯并二氢吡喃环取代的黄酮类?
“Shandougen” and “Kushen” are the commonly used traditional Chinese
medicines derived from Sophora plants. “Shandougen” is the dried roots and
rhizomes of Sophora tonkinensis Gapnep. and “Kushen” is the dried roots of
Sophora flavescens Ait.. The two crude drugs are so similar in the chemical
constituents that they were both stated to contain quinolizidine alkaloids,
prenylated flavonoids and oleanene triterpenoids. But their clinical applications
are quite different, “Shandougen” is mainly used to treat acute pharyngolaryngeal
infections and sore throat, while “Kushen” is mostly used to treat the skin diseases
and the gynaecological diseases such as eczema, dermatitis and colpitis. In the
Chinese Pharmacopoeia (CP), the TLC tests given for the identification of
“Shandougen” and “Kushen” lack specificity, in which the alkaloids matrine,
oxymatrine and sophoridine are chosen as the qualitative markers. And in CP, it
seems unsuitable to assess the quality of “Kushen” by determining the content of
the minor compound matrine, the content of which is much lower than those of the
other two active constituents oxymatrine and oxysophocarpine in this drug. And
the discrepancy between the theory and the practice of traditional Chinese
medicine requires to assess the quality of the crude drugs with multiple indicators.
Therefore, in order to specify “Shandougen” from “Kushen” effectively, to
assess the quality of these two crude drugs comprehensively, to supply useful
information for the further understanding on the relationships between the
chemical constituents and the unique medicinal properties claimed for
“Shandougen” and “Kushen”, and also to search for antiviral agents from natural
products as well, the chemical constituents of “Shandougen” and “Kushen” were
investigated systemically. Their alkaloid and flavonoid compositions were
compared comprehensively by HPLC fingerprinting, and the contents of several
active quinolizidine alkaloids in the commercial drugs from different sources were
determined by HPCE method. In addition, a study on the chemical reference
substances of Sophora tonkinensis was also carried out.
vii
Part One: The Chemical Constituents of S. tonkinensis and S. flavescens
Ten compounds were isolated from the acid water-soluble part and
twenty-two compounds were isolated from the ether-soluble fraction of the ethanol
extracts of the roots and rhizomes of S. tonkinensis, respectively, by repeated
column chromatography and preparative TLC method. The structures of thirty
compounds were elucidated by spectroscopic methods as follows: the alkaloids
(+)-matrine (T1), (+)-oxymatrine (T2), (+)-sophoranol (T3), (-)-14β-hydroxymatr-
ine (T4), (-)-14β-hydroxyoxymatrine (T5), (-)-sophocarpine (T6),
(-)-5α-hydroxysophocarpine (T7), (-)-cytisine (T8), (-)-N-methylcytisine (T9); the
flavonoids sophoratonkinochromane A (T10), sophoratonkinochromane B (T11),
sophoratonkinochromane C (T12), sophoratonkinochromane D (T13),
sophoratonkidochromane B (T14), sophoratonkidochromane A (T15),
sophoratonkidochromane C (T16), formononetin (T17), 8-methylretusin (T18),
(-)-trifolirhizin (T19); the triterpenoids (+)-lupeol (T20), (+)-sophoradiol (T21);
the phenolic components piscidic acid monoethyl ester (T22), maltol (T23),
venillic acid (T24), p-hydroxybenzoic acid (T25), docosyl caffeate (T26); the other
compounds physcion (T27), emodin (T28), flemichapparin (T29) and β-sitosterol
(30). Among them, T5, T10, T11, T12, T13, T14 and T16 were new compounds,
T22, T23, T27 and T28 were isolated from genus Sophora and T17, T18, T24,
T25 and T29 were isolated from this species for the first time.
Eleven compounds were isolated from the acid water-soluble part and
twenty-two compounds were isolated from the ether-soluble fraction of the ethanol
extracts of the roots of S. flavescens, respectively, by repeated column
chromatography a
引文
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