Chemical Compounds Isolated from Pleione maculata and Their Bioactive Activity
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摘要:
目的 研究秋花独蒜兰化学成分,发现其活性成分。 方法 秋花独蒜兰经95%乙醇提取、硅胶柱层析、半制备HPLC和Sephadex LH-20柱层析进行分离纯化,波谱分析(核磁共振氢谱、碳谱、和质谱)确定结构;应用MTT法,对部分化合物进行体外抗肿瘤活性筛选。 结果 从秋花独蒜兰分离鉴定10个化合物,分别为:1,7-dihydroxy-2,5-dimethoxyphenanthrene ( 1 ),2,7-dihydroxy-1,5-dime-thoxyphenanthrene ( 2 ),confusarin ( 3 ),4,7-dihydroxy-2-dimethoxy-9,10-dihydrophe-nanthrene ( 4 ),pleionesin B ( 5 ),pleionesin C ( 6 ),flavanthrin ( 7 ),2,2′-dihydroxy-5,5′,7,7′-tetramethoxy-9,9′,10,10′-tetrahydro-3,3′-biphenanthrene ( 8 ),6,6′,7,7′-tetrahy--droxy-2,2′,4,4′-tetramethoxy -8,8′-biphenanthrene ( 9 ),1,3′,5′,7-tetrahydroxy-4,7′-dimethoxy-9,9′,10,10′-tetrahydro-2,2′-biphenanthrene (1 0 );对化合物3,7~10 A549、MCF-7/S和SKOV-3进行肿瘤细胞株抑制活性测试,发现化合物10对3种细胞株活性较好。 结论 所有化合物为首次从本植物中分离得到,研究结果表明化合物10对3种肿瘤细胞株具有很好的抑制活性,其IC50分别为2.45,6.83,4.23 μM。 Abstract:Objective To study the chemical compounds from the medicinal plants of Pleione maculata and find its bioactive compounds. Methods The compounds were extracted by alcohol (95%) and isolated by column chromatography on silica gel and Sephadex LH-20. Their structures were identified by spectroscopic analysis (1H NMR, 13CNMR and EIMS). The antitumor activity of the compounds was studied by MTT assay in vitro. Results Ten compounds were obtained and identified as 1, 7-dihydroxy-2, 5 -dimethoxyphenanthrene ( 1 ), 2, 7-dihydroxy-1, 5-dimethoxyphenanthrene ( 2 ), confusarin ( 3 ), 4, 7-dihydroxy-2-dimethoxy-9, 10-dihydrophenanthrene ( 4 ), pleionesin B ( 5 ), pleionesin C ( 6 ), flavanthrin ( 7 ), 2, 2′-dihydroxy-5, 5′, 7, 7′-tetramethoxy-9, 9′, 10, 10′-tetrahydro-3, 3′-biphenanthrene ( 8 ), 6, 6′, 7, 7′-tetrahy- -droxy-2, 2′, 4, 4′-tetramethoxy -8, 8′-biphenanthrene ( 9 ), 1, 3′, 5′, 7-tetrahydroxy-4, 7′ -dimethoxy-9, 9′, 10, 10′-tetrahydro-2, 2′- biphenanthrene (1 0 ); Compounds 3, 7~10 were tested for the inhibitory activity of human lung cancer cell lines (A549), human breast cancer drug-sensitive cell lines (MCF-7/S), and human ovarian cancer cell lines (SKOV-3). The results of anti-tumor activity test of compounds showed that 10 showed good inhibitory activity on three cell lines. Conclusion All compounds were isolated from this plant for the first time. Compound 10 has good inhibitory activity against three tumor cell lines, and with IC50 of 2.45, 6.83, 4.23 μM, respectively. -
Key words:
- Pleione maculata /
- Chemical constituents /
- Bioactive activity
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表 1 化合物3,7~10对3种细胞株的细胞毒活性IC50 (μM)
Table 1. Cytotoxic activities of compounds 3,7~10 on three cell lines IC50 (μM)
化合物 A549 MCF-7/S SKOV-3 3 163.6 33.42 98.49 7 106.8 112.2 76.08 8 91.2 41.5 22.4 9 38.91 102.2 56.92 10 2.45 6.83 4.23 DDP 22.02 10.02 14.15 -
[1] 中国科学院中国植物志编辑委员会. 中国植物志 [M], 第18卷, 北京: 科学出版社, 1999: 366-367. [2] 国家药典委员会. 中华人民共和国药典·一部[S]. 北京: 中国医药科技出版社, 2015: 32 -33. [3] Takamiya T,Kitamura S,Suzuki S,et al. Identification of two phenanthrene derivatives from Australasian allied species in genus Dendrobium[J]. Chemical & Pharmaceutical Bulletin,2018,66(6):642-650. [4] Majumder P L,Kar A. Confusarin and confusaridin two phenanthrene derivatives of the orchid Eria Confusa[J]. Phytochemistry,1987,26(4):1127-1129. doi: 10.1016/S0031-9422(00)82363-8 [5] Nanik S A,Ratih H,Mulyadi T. Confusarin and nudol,two phenathrene group compounds,from Dioscorea esculenta L. and their antioxidant activities[J]. Journal of Chemical Technology and Metallurgy,2017,52(6):1135-1139. [6] Li C B,Wang C,Fan W W,et al. Chemical components of Dendrobium crepidatum and their neurite outgrowth enhancing activities[J]. Natural Products & Bioprospecting,2013,3(2):70-73. [7] Pornprom K,Kesarin B,Pithi C,et al. Cytotoxic and antimigratory activities of phenolic compounds from Dendrobium brymerianum[J]. Evidence-Based Complementary and Alternative Medicine,2015,15(1):1-9. doi: 10.1186/s12906-015-0520-z [8] Majumder P L,Lahiri S. Lusianthrin and lusianthridin,two stilbenoids from the orchid Lusia indivisa[J]. Phytochemistry,1990,29(2):621-624. doi: 10.1016/0031-9422(90)85129-4 [9] Dong H L,Wang C,Li Y,et al. Complete assignments of 1H and 13C NMR data of three new dihydrophenanthrofurans from Pleione yunnanensis[J]. Magnetic Resonance in Chemistry,2011,48(3):256-260. [10] Majumder P L,Banerjee S. Structure of flavanthrin,the first dimeric 9,10-dihydro -phenanthrene derivative from the orchid Eria flava[J]. Tetrahedron,1988,44(23):7303-7308. doi: 10.1016/S0040-4020(01)86102-0 [11] Li C Y,Liu J,Su X H,et al. New dimeric phenanthrene and flavone from Spiranthes sinensis[J]. Journal of Asian Natural Products Research,2013,15(4):1-5. [12] Majumder P L,Lahiri S. Volucrin,a new dimeric phenanthrene derivative from the orchid lusia volucris[J]. Tetrahedron,1990,46(10):3621-3626. doi: 10.1016/S0040-4020(01)81531-3 [13] Xu J J,Yu H,Qing C,et al. Two new biphenanthrenes with cytotoxic activity from Bulbophyllum odoratissimum[J]. Fitoterapia,2009,80(7):381-384. doi: 10.1016/j.fitote.2009.05.007 [14] Shao S Y,Wang C,Han S W,et al. Phenanthrenequinone enantiomers with cytotoxic activities from the tubers of Pleione bulbocodioides[J]. Organic & Biomolecular Chemistry,2019,17(3):567-572. [15] Shao S Y,Wang C,Han S W,et al. Two new phenanthrenequinones with cytotoxic activity from the tubers of Pleione bulbocodioides[J]. Phytochemistry Letters,2020,35(6):6-9. [16] 李媛,李玉鹏,郑金蓉,等. 云南独蒜兰菲和联苄类化学成分的研究(英文)[J]. 昆明医科大学学报,2021,42(2):29-32. [17] 王静,肖秋肖,周祖英,等. 基原为云南独蒜兰的山慈菇的化学成分鉴定与分析[J]. 中国药房,2022,33(10):1165-1171. [18] Li Y P,Chen Y P,Chen X L,et al. A new phenanthrene derivative with α-Glucosidase inhibitory activity from Pleione maculata[J]. Chemistry of Natural Compounds,2022,58(1):6-8. [19] Li Y P,Shao Y T,Zhang R P. A new phenanthrene derivative from Pleione praecox[J]. Chemistry of Natural Compounds,2021,57(3):409-441. [20] 张伟,王继华,范泽鑫,等. 独蒜兰属植物杂交育种研究进展[J]. 北方园艺,2020,461(14):136-144. [21] 王中煊,张豪,陈蕾,等. 15种独蒜兰属植物叶表皮微形态特征及分类学意义研究[J]. 西北植物学报,2020,40(9):1527-1538. [22] 沈立明,戴中武,钟惠,等. 3种独蒜兰属植物的光合特性[J]. 热带作物学报,2021,42(5):1355-1360. [23] 王跃华,陈芳,鲜俊贤,等. 独蒜兰优质种苗快速培育研究[J]. 成都大学学报(自然科学版),2021,40(3):242-246.