雷公藤叶的化学成分及生物活性研究
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摘要
雷公藤(Tripterygium wilfordii HooK. F.)是卫矛科(Celastraceae)雷公藤属植物,夏、秋季节采集,以根、叶、花及果入药,性凉,味苦、辛,有大毒,具有祛风除湿、活血通络、消肿止痛、杀虫解毒等功效。以根为原料的药物制剂已经广泛应用于临床治疗类风湿性关节炎等疾病,但是关于叶的化学成分及生物活性研究报道较少。
本文利用80%乙醇对雷公藤叶50Kg进行回流提取,提取液经乙酸乙酯萃取后得到提取物。采用聚酰胺柱层析、硅胶柱层析、凝胶柱层析、中压柱色谱、高效液相柱色谱等色谱方法对乙酸乙酯萃取物进行分离纯化后得到了73个化合物。通过ESIMS. HRESIMS、UV、IR、ID、2D NMR等光谱方法鉴定了所得到的73个化合物的结构,发现新化合物28个。其中1*-20*为新的二氢沉香呋哺型倍半萜多醇酯,分别命名为Triptersinine A (1*). Triptersinine B (2*)、 Triptersinine C (3*)、 Triptersinine D (4). Triptersinine E (5)、Triptersinine F (6)、Triptersinine G (7)、Triptersinine H (8)、 Triptersinine I (9)、Triptersinine J (10、Triptersinine K (11*)、 Triptersinine L (12)、 Triptersinine M (13).Triptersinine N (14)、Triptersinine O (15)、Triptersinine P (16)、 Triptersinine Q (17*)、 Triptersinine R (18*)、 Triptersinine S (19*)、Triptersinine T (20*)；30*-35*为新的二萜内酯类,其中30*-33*为具有6/6/5坏稠合骨架的新颖二萜内酯类化合物,分别命名为Tripterlide A、Tripterlide B、Tripterlide C、Tripterlide D,34*为芳香化的18(4→3)abeo-松香烷型二萜内酯醇,命名为Tripterlide E.35*为降碳芳香化的18(4→3)abeo-松香烷型二萜内酯醇,命名为Tripterlide F;42*为新的降碳异戊二烯类,鉴定为3,9,10-Trihydroxymegastigman-5-ene;65*为新的苯丙素类化合物,鉴定为2,6-Dimethoxy-4-[(1E)-3-hydroxy-1-propen-1-yl]Benzenemethanol。通过文献对照鉴定21-29为倍半萜生物碱类化合物；37-41为18(4→3)abeo-松香烷型二萜内酯醇；43-56为降碳异戊二烯萜；57-61为木脂素类化合物；62-64、66-73为其他类型的化合物。
本文对所分离得到的化合物进行了神经胶质瘤细胞缺氧诱导因子-1(HIF-1)抑制活性,5种人肿瘤细胞毒活性的筛选、评价。结果显示二萜类化合物35、36、38-40具有HIF-1抑制活性,其中尤以38活性最强(IC500.02μM)；14、15、65显示了针对人结肠癌细胞株HCT-8的抑制活性；38、39显示了对5种人肿瘤细胞株(HCT-8、Bel-7402. BGC-823. A549. A2780)的抑制活性。对部分倍半萜多醇酯类化合物进行了抑制小鼠腹腔巨噬细胞NO释放的活性评价,1、11、21、22、27对巨噬细胞产生NO的抑制率均在45%以上,其中22对NO产生的抑制率达到了59%。
上述雷公藤叶的化学成分及抗肿瘤活性研究表明雷公藤叶中的主要活性成分为松香烷型二萜内酯。本文以从雷公藤叶中分离得到的二萜化合物雷公藤内酯醇(Triptolide,38)为原料,通过一系列的酯化、氧化、还原等反应制备了24个衍生物。
本文通过芳香酰氯与雷公藤内酯醇14位羟基的酯化反应得到了系列衍生物A1-A16,以及3个副产物A6-2、A6-3、A15-2。抗肿瘤活性评价显示A8、A9、A11、 A12、A13、A16具有显著的HIF-1抑制活性(IC50<10μM)；除了A6-3、A14外均具有较强的肿瘤细胞毒活性。以上述活性筛选以及文献调研为指导,本文对雷公藤内酯醇进行C-5与14-OH的结构改造,得到了目标产物A20、A21以及中间产物A17-A19、A22-A24,此外还得到了副产物A20-2。抗肿瘤活性评价显示A23具有较显著的HIF-1抑制活性(IC500.04μM),A18显示了肿瘤细胞毒活性。
Tripterygium wilfordii Hook. F.(Celastraceae) is a traditional Chinese medicine distributed in the southern part of China, the roots of which have been used to treat cancer and inflammation. Recently, a traditional Chinese medicine preparation derived from a water/chloroform extract of the roots of T. wilfordii (the so-called "total multi-glycoside") has been employed in the clinical treatment of rheumatoid arthritis, skin disorders, male-fertility control, and other inflamatory and autoimmune diseases. Compared with the investigations of the roots of T. wilfordii, few chemical studies have been conducted on the leaves, although the leaves exhibited marked anti-inflammatory activity.
Air-dried leaves of T. wilfordii (50kg) were extracted with80%ethanol. After evaporation of EtOH in vacuo, the aqueous residue was diluted with water and then partitioned with EtOAc. Seventy three compounds were isolated from the EtOAc extract by a variety of chromatographic techniques such as silica gel, sephadex LH-20, MPLC, and HPLC. Their structures were elucidated on the basis of UV, IR, HRESIMS,1D-and2D-NMR. Compounds1-20were new dihydroagarofuran sesquiterpene polyol esters, named Triptersinine A-T. Compounds30*-33*were new diterpenoids possessing a6/6/5tricyclic ring system, named Tripterlide A-D.34and35were new18(4→3) abeo-abietane diterpenoids.42*was new C13nor-isoprenoid.65was new phenylpropanoids. The other compounds were determined as known compounds on the basis of literatures.
The anti-tumor activities of all the compounds were evaluated in vitro. Compounds35,36,38-40exhibited inhibitory activity on the HIF-1target. Among them,38showed most inhibitory activity with an IC50value of0.02μM.14,15, and65showed cytotoxicit yagainst HCT-8(human colon carcinoma) cell lines.38and39showed significant cytotoxicityagainst A549(human lung carcinoma), Bel-7402(human livercarcinoma), BGC-823(human stomach carcinoma), HCT-8(human colon carcinoma), and A2780(human ovarian carcinoma) cell lines. Compounds1,11,21,22, and27showed moderate inhibitory effects onnitric oxide production in LPS-induced macrophages at5μM.
It is obviously that abietane diterpenoids were the bioactive substance of T. wilfordii. Based on triptolide (38), twenty four derivatives were prepared by the chemical reactions. The modification of14-OH of triptolide afforded derivatives A1-A16, and three by-products (A6-2, A6-3, A15-2). The anti-tumor effects evaluation exhibited that A8, A9, All, A12, A13, and A16inhibited the HIF-1target significantly; all derivatives inhibited the proliferation of five human cancer cell lines except A6-3, A14. As a result of the modification and bioassay of the derivatives of the14-OH of triptolide, we designed and prepared the derivatives A17-A24based on the modification of the C-5,14-OH of triptolide. A23showed significant inhibitory effect on the HIF-1target. A18exhibited moderate cytotoxicity against five human cancer cell lines.
本文利用80%乙醇对雷公藤叶50Kg进行回流提取,提取液经乙酸乙酯萃取后得到提取物。采用聚酰胺柱层析、硅胶柱层析、凝胶柱层析、中压柱色谱、高效液相柱色谱等色谱方法对乙酸乙酯萃取物进行分离纯化后得到了73个化合物。通过ESIMS. HRESIMS、UV、IR、ID、2D NMR等光谱方法鉴定了所得到的73个化合物的结构,发现新化合物28个。其中1*-20*为新的二氢沉香呋哺型倍半萜多醇酯,分别命名为Triptersinine A (1*). Triptersinine B (2*)、 Triptersinine C (3*)、 Triptersinine D (4). Triptersinine E (5)、Triptersinine F (6)、Triptersinine G (7)、Triptersinine H (8)、 Triptersinine I (9)、Triptersinine J (10、Triptersinine K (11*)、 Triptersinine L (12)、 Triptersinine M (13).Triptersinine N (14)、Triptersinine O (15)、Triptersinine P (16)、 Triptersinine Q (17*)、 Triptersinine R (18*)、 Triptersinine S (19*)、Triptersinine T (20*)；30*-35*为新的二萜内酯类,其中30*-33*为具有6/6/5坏稠合骨架的新颖二萜内酯类化合物,分别命名为Tripterlide A、Tripterlide B、Tripterlide C、Tripterlide D,34*为芳香化的18(4→3)abeo-松香烷型二萜内酯醇,命名为Tripterlide E.35*为降碳芳香化的18(4→3)abeo-松香烷型二萜内酯醇,命名为Tripterlide F;42*为新的降碳异戊二烯类,鉴定为3,9,10-Trihydroxymegastigman-5-ene;65*为新的苯丙素类化合物,鉴定为2,6-Dimethoxy-4-[(1E)-3-hydroxy-1-propen-1-yl]Benzenemethanol。通过文献对照鉴定21-29为倍半萜生物碱类化合物；37-41为18(4→3)abeo-松香烷型二萜内酯醇；43-56为降碳异戊二烯萜；57-61为木脂素类化合物；62-64、66-73为其他类型的化合物。
本文对所分离得到的化合物进行了神经胶质瘤细胞缺氧诱导因子-1(HIF-1)抑制活性,5种人肿瘤细胞毒活性的筛选、评价。结果显示二萜类化合物35、36、38-40具有HIF-1抑制活性,其中尤以38活性最强(IC500.02μM)；14、15、65显示了针对人结肠癌细胞株HCT-8的抑制活性；38、39显示了对5种人肿瘤细胞株(HCT-8、Bel-7402. BGC-823. A549. A2780)的抑制活性。对部分倍半萜多醇酯类化合物进行了抑制小鼠腹腔巨噬细胞NO释放的活性评价,1、11、21、22、27对巨噬细胞产生NO的抑制率均在45%以上,其中22对NO产生的抑制率达到了59%。
上述雷公藤叶的化学成分及抗肿瘤活性研究表明雷公藤叶中的主要活性成分为松香烷型二萜内酯。本文以从雷公藤叶中分离得到的二萜化合物雷公藤内酯醇(Triptolide,38)为原料,通过一系列的酯化、氧化、还原等反应制备了24个衍生物。
本文通过芳香酰氯与雷公藤内酯醇14位羟基的酯化反应得到了系列衍生物A1-A16,以及3个副产物A6-2、A6-3、A15-2。抗肿瘤活性评价显示A8、A9、A11、 A12、A13、A16具有显著的HIF-1抑制活性(IC50<10μM)；除了A6-3、A14外均具有较强的肿瘤细胞毒活性。以上述活性筛选以及文献调研为指导,本文对雷公藤内酯醇进行C-5与14-OH的结构改造,得到了目标产物A20、A21以及中间产物A17-A19、A22-A24,此外还得到了副产物A20-2。抗肿瘤活性评价显示A23具有较显著的HIF-1抑制活性(IC500.04μM),A18显示了肿瘤细胞毒活性。
Tripterygium wilfordii Hook. F.(Celastraceae) is a traditional Chinese medicine distributed in the southern part of China, the roots of which have been used to treat cancer and inflammation. Recently, a traditional Chinese medicine preparation derived from a water/chloroform extract of the roots of T. wilfordii (the so-called "total multi-glycoside") has been employed in the clinical treatment of rheumatoid arthritis, skin disorders, male-fertility control, and other inflamatory and autoimmune diseases. Compared with the investigations of the roots of T. wilfordii, few chemical studies have been conducted on the leaves, although the leaves exhibited marked anti-inflammatory activity.
Air-dried leaves of T. wilfordii (50kg) were extracted with80%ethanol. After evaporation of EtOH in vacuo, the aqueous residue was diluted with water and then partitioned with EtOAc. Seventy three compounds were isolated from the EtOAc extract by a variety of chromatographic techniques such as silica gel, sephadex LH-20, MPLC, and HPLC. Their structures were elucidated on the basis of UV, IR, HRESIMS,1D-and2D-NMR. Compounds1-20were new dihydroagarofuran sesquiterpene polyol esters, named Triptersinine A-T. Compounds30*-33*were new diterpenoids possessing a6/6/5tricyclic ring system, named Tripterlide A-D.34and35were new18(4→3) abeo-abietane diterpenoids.42*was new C13nor-isoprenoid.65was new phenylpropanoids. The other compounds were determined as known compounds on the basis of literatures.
The anti-tumor activities of all the compounds were evaluated in vitro. Compounds35,36,38-40exhibited inhibitory activity on the HIF-1target. Among them,38showed most inhibitory activity with an IC50value of0.02μM.14,15, and65showed cytotoxicit yagainst HCT-8(human colon carcinoma) cell lines.38and39showed significant cytotoxicityagainst A549(human lung carcinoma), Bel-7402(human livercarcinoma), BGC-823(human stomach carcinoma), HCT-8(human colon carcinoma), and A2780(human ovarian carcinoma) cell lines. Compounds1,11,21,22, and27showed moderate inhibitory effects onnitric oxide production in LPS-induced macrophages at5μM.
It is obviously that abietane diterpenoids were the bioactive substance of T. wilfordii. Based on triptolide (38), twenty four derivatives were prepared by the chemical reactions. The modification of14-OH of triptolide afforded derivatives A1-A16, and three by-products (A6-2, A6-3, A15-2). The anti-tumor effects evaluation exhibited that A8, A9, All, A12, A13, and A16inhibited the HIF-1target significantly; all derivatives inhibited the proliferation of five human cancer cell lines except A6-3, A14. As a result of the modification and bioassay of the derivatives of the14-OH of triptolide, we designed and prepared the derivatives A17-A24based on the modification of the C-5,14-OH of triptolide. A23showed significant inhibitory effect on the HIF-1target. A18exhibited moderate cytotoxicity against five human cancer cell lines.
引文
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