Chemical Composition and Biological Activity of Dendrobium primulinum
-
摘要:
目的 研究报春石斛化学成分,发现其活性成分。 方法 报春石斛经溶剂提取、硅胶和凝胶柱色谱分离,波谱分析确定结构。部分化合物体外活性筛选采用MTT法。 结果 从报春石斛中分离鉴定了7个化合物,分别为7-dihydroxy-2,4-methoxyphenanthrene (1)、densiflorol B (2)、3,4,7-trihydroxy-2-methoxy-9,10-dihydrophenanthrene (3)、thunalbene (4)、phillygenin (5)、3β-hydroxy-5α,8α-epidioxyergosta-6,22-diene (6)、4-hydroxy-3,5-dimethoxycinnamaldehyde (7),对化合物1~5进行抗肿瘤活性测试,结果显示化合物1对MCF-7/S细胞株抑制活性较强。 结论 化合物1~6为首次从本植物中分离得到,化合物7为首次从本属植物中分离得到,1对MCF-7/S细胞株IC50为5.13 μM。 Abstract:Objective To study the chemical composition of and identify its active components. Methods The chemical constituents of Dendrobium Primulinum were extracted using solvents, followed by separation through silica gel and gel column chromatography, with structural identification performed via spectral analysis. The in vitro activity screening of some compounds was conducted using the MTT assay. Results Seven compounds were isolated and identified from Dendrobium primulinum, namely 7-dihydroxy-2, 4-methoxyphenanthrene(1), densiflorol B (2), 3, 4, 7-trihydroxy-2-methoxy-9, 10-dihydrophenanthrene (3), thunalbene (4), phillygenin (5), 3β-hydroxy-5α, 8α-epidioxyergosta-6, 22-diene (6)、4-hydroxy-3, 5-dimethoxy--cinnamaldehyde (7) . Antitumor activity tests were performed on compounds 1 to 5, revealing that compound 1 exhibited strong inhibitory activity against the MCF-7/S cell line, with an IC50 of 5.13 μM. Conclusion Compounds 1 to 6 are reported for the first time from Dendrobium primulinum, while compound 7 is reported for the first time from this genus. -
Key words:
- Dendrobium primulinum /
- Chemical constituents /
- Bioactive activity
-
表 1 化合物1~5对3种细胞株的细胞毒活性IC50(μmol/L)
Table 1. Cytotoxic activity IC50 (μmol/L) of compounds 1~5 against three cell lines
化合物 A549 MCF-7/S SKOV-3 1 23.25 5.13 45.43 2 23.95 34.73 15.35 3 59.31 32.20 13.81 4 69.15 66.95 29.35 5 41.65 54.75 21.75 DDP 22.02 10.02 14.15 -
[1] 余乐 流苏、金钗、报春石斛种子非共生萌发以及流苏石斛离体保存的研究 [D]. 重庆: 西南大学,2009. [2] Björn L,Kurt L,Jakob G N,et al. Studies on Orchidaceae Alkaloids. III. The Alkaloids in Dendrobium primulinumLindl. and Dendrobium chrysanthum Wall[J]. Acta Chemica Scandinavica,1965,19:1607-1611. doi: 10.3891/acta.chem.scand.19-1607 [3] 周晓蓉,杨梅君,杨玥娜,等. 独蒜兰的化学成分及其生物活性[J]. 昆明医科大学学报,2023,44(5):1-5. doi: 10.12259/j.issn.2095-610X.S20230528 [4] Stoessl A,Stothers J. Carbon‐13 NMR studies. 96—carbon‐13 spectra of several polyhydroxylated 9,10‐dihydrophenanthrene and phenanthrene derivatives[J]. Organic Magnetic Resonance,1982,20(3):166-169. doi: 10.1002/mrc.1270200311 [5] Yan X,Tang B,Liu M. Phenanthrenes from Arundina graminifolia and in vitro evaluation of their antibacterial and anti-haemolytic properties[J]. Natural Product Research,2018,32(6):707-710. doi: 10.1080/14786419.2017.1332606 [6] Leong Y W,Kang C C,Harrison L J,et al. Phenanthrenes,dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum[J]. Phytochemistry,1997,44(1):157-165. doi: 10.1016/S0031-9422(96)00387-1 [7] Majumder P,Roychowdhury M,Chakraborty S. Thunalbene,a stilbene derivative from the Orchid Thunia alba[J]. Phytochemistry,1998,49(8):2375-2378. doi: 10.1016/S0031-9422(98)00433-6 [8] Ferreira A G,Motidome M,Gottlieb O R,et al. Farnesyl-homogentisic acid derivatives from Otobaparvifolia[J]. Phytochemistry,1989,28(2):579-583. doi: 10.1016/0031-9422(89)80055-X [9] 麻兵继,刘吉开. 密褶红菇化学成分研究[J]. 天然产物研究与开发,2005,17(1):29-32. doi: 10.3969/j.issn.1001-6880.2005.01.008 [10] 黄艳萍,吴学谦,胡玲,等. 三叶青内生真菌Phomopsis sp. YK-7的化学成分研究[J]. 中草药,2017,48(15):3032-3036. [11] 李玖慧,陈光英,韩长日,等. 青梅茎的化学成分[J]. 中国药科大学学报,2012,43(1):25-27. [12] 刘莎莎,李红锐,孙静贤,等. 流苏石斛乙醇提取物的化学成分研究[J]. 云南民族大学学报(自然科学版),2022,31(4):375-380. doi: 10.3969/j.issn.1672-8513.2022.04.001 [13] 王亚兰,张笑,韩邦兴,等. 石斛碱和石斛酚对小鼠细胞色素P450表达与活性作用研究[J]. 中国野生植物资源,2022,41(6):23-30. doi: 10.3969/j.issn.1006-9690.2022.06.005 [14] 刘婵,刘娟,商黔惠. 石斛碱抑制高钠盐诱导的心脏成纤维细胞增殖[J]. 中国动脉硬化杂志,2017,25(7):649-654. doi: 10.3969/j.issn.1007-3949.2017.07.001 -