Thant May Thazin, Bhummaphan Narumol, Wuttiin Jittima, Puttipanyalears Charoenchai, Chaichompoo Waraluck, Rojsitthisak Pornchai, Punpreuk Yanyong, Böttcher Chotima, Likhitwitayawuid Kittisak, Sritularak Boonchoo
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand.
College of Public Health Sciences, Chulalongkorn University, Bangkok 10330, Thailand.
ACS Omega. 2024 Feb 9;9(7):7679-7691. doi: 10.1021/acsomega.3c07048. eCollection 2024 Feb 20.
The phytochemical investigation of the whole plants of Lindl. var. led to the discovery of three new phenolic glycosides, i.e., coelofusides A-C () and 12 known compounds (). For the first time, we reported the nuclear magnetic resonance (NMR) data of 4--(6'--glucosyl-4″-hydroxybenzoyl)-4-hydroxybenzyl alcohol () in this study. The identification of the structures of newly discovered compounds was done through the analysis of their spectroscopic data [NMR, mass spectrometry, ultraviolet, Fourier transform infrared, optical rotation, and circular dichroism (CD)]. In comparison to anticancer drugs (i.e., etoposide and carboplatin), we evaluated anticancer potential of the isolated compounds on two different breast cancer cell lines, namely, T47D and MDA-MB-231. Human fibroblast HaCaT cells were used as the control cells. After a 48 h incubation, flavidin (), coelonin (), 3,4-dihydroxybenzaldehyde (), and oxoflavidin () showed significant cytotoxic effects against breast cancer cells. Among them, oxoflavidin () exhibited the most potent cytotoxicity on MDA-MB-231 with an IC value of 26.26 ± 4.33 μM. In the nuclear staining assay, oxoflavidin induced apoptosis after 48 h in both T47D and MDA-MB-231 cells in a dose-dependent manner. Furthermore, oxoflavidin upregulated the expression of apoptotic genes, such as p53, Bax, poly(ADP-ribose) polymerase, caspase-3, and caspase-9 genes while significantly decreasing antiapoptotic protein (Bcl-2) expression levels.
对Lindl. var.全株植物进行的植物化学研究发现了三种新的酚苷,即coelofusides A - C()和12种已知化合物()。在本研究中,我们首次报道了4 - (6'-葡萄糖基 - 4″ - 羟基苯甲酰基)-4 - 羟基苄醇()的核磁共振(NMR)数据。通过对新发现化合物的光谱数据[核磁共振、质谱、紫外、傅里叶变换红外、旋光和圆二色性(CD)]进行分析来鉴定其结构。与抗癌药物(即依托泊苷和顺铂)相比,我们评估了分离出的化合物对两种不同乳腺癌细胞系,即T47D和MDA - MB - 231的抗癌潜力。人成纤维细胞HaCaT细胞用作对照细胞。孵育48小时后,flavidin()、coelonin()、3,4 - 二羟基苯甲醛()和oxoflavidin()对乳腺癌细胞显示出显著的细胞毒性作用。其中,oxoflavidin()对MDA - MB - 231表现出最强的细胞毒性,IC值为26.26±4.33μM。在细胞核染色试验中,oxoflavidin在48小时后以剂量依赖性方式诱导T47D和MDA - MB - 231细胞凋亡。此外,oxoflavidin上调了凋亡基因如p53、Bax、聚(ADP - 核糖)聚合酶、caspase - 3和caspase - 9基因的表达,同时显著降低抗凋亡蛋白(Bcl - 2)的表达水平。