Flavone constituents of Phlomis bruguieri Desf. with cytotoxic activity against MCF-7 breast cancer cells

Abstract

Phlomis bruguieri (P. bruguieri) is a large genus in the Lamiaceae family, with a wide variety distributed in Euro-Asia, Central Asia, Iran, and China. Phlomis flowers have been used as herbal tea for gastrointestinal disturbances, protection of liver and cardiovascular systems. The aim of this study was to analyse phytochemical of flavonoid constituents in semi polar fraction of P. bruguieri. Methanol extract of plant material (4 kg) yielded 361 g dark green concentrated extract gum. After preliminary fractionation by normal column chromatography on silica gel, Fr. 2 eluted with chloroform: methanol (90:10) selected as semi polar fraction and was more purified using different chromatography columns on silica gel, polyamide SC6 and Sephadex LH-20 adsorbents. Finally one new and three known flavonoids (1-4) were characterized in semi polar fraction. Isolated structures were identified using 1H-NMR, 13C-NMR, 31P-NMR, HSQC, HMBC, negative ESI mass, and UV spectra using different shift reagents. Using standard MTT assay, cytotoxicity of isolated new compound was done against michigan cancer foundation-7 (MCF-7) breast cancer cells. Phytochemical analysis of P. bruguieri resulted in identification of one new 4’-methoxy-luteolin-7-phosphate and three known flavones including luteolin, apigenin, and tricin for the first time in this plant. In MTT cytotoxicity test, 4’-methoxy-luteolin-7-phosphate showed cytotoxicity with IC50 value of 43.65 ± 8.56 μM agasint MCF-7 breast cancer cells.

Chemical Constituents and Anticancer Activities of the Extracts from Phlomis × commixta Rech. f. (P. cretica × P. lanata)

“…Both compound ( 6) and ( 8) are phenylpropanoids, which suggests that the plant can biosynthesize these kinds of secondary metabolites in each plant part. The compounds were identified as brassicasterol (4) (see Supplementary Data Table S2) [44,45], stigasterol (5) (see Supplementary Data Table S3) [46,47], verbascoside (6) (see Supplementary Data Table S4) [48], martynoside (7) (see Supplementary Data Table S5) [48], forsythoside B (8) (see Supplementary Data Table S6) [49], allysonoside (9) (see Supplementary Data Table S7) [50], echinacoside (10) (see Supplementary Data Table S8) [51], p-coumaric acid (11) (see Supplementary Data Note S1) [52], caffeic acid (12) (see Supplementary Data Note S2) [53], chlorogenic acid (13) (see Supplementary Data Table S9) [54], chlorogenic acid methyl ester (14) (see Supplementary Data Table S10) [55], 5,7-dihydroxychromone (15) (see Supplementary Data Note S3) [56], p-hydroxybenzoic acid (16) (see Supplementary Data Table S11) [57], gallic acid (17) (see Supplementary Data Note S4) [58], vanillic acid (18) (See Supplementary Data Note S5) [57], naringenin …”

“…Over the last few years, there has been a rapid increase in the information available on the structures and pharmacological activities of new compounds isolated and identified from Phlomis species [6][7][8][9][10][11][12][13].…”

“…Phlomis species contain a diverse range of compounds, including iridoid glucosides [14][15][16], phenylpropanoid glycosides [17], flavonoid glycosides [18], lignans [19], neolignan glycosides [20], monoterpene glycosides [21], megastigmanes [22], diterpene glycosyl esters [23,24], nortriterpenes [25,26] and essential oils [5], which were reported to be responsible for various biological and pharmacological properties. Among them are the antinociceptive, anti-inflammatory [27][28][29], antioxidant [30][31][32][33][34], antimicrobial [35,36], wound-healing, antidiabetic [37,38] and antihemoroidal activity [39], as well as the antiplasmodial and anticancer activities [12,38,[40][41][42][43].…”

The Combined Therapeutic Effect of Capecitabine and Naringin on HER2+ (SK-BR-3) and HER2- (MCF-7) Human Breast Cancer Cells Lines

“…Then, the culture medium was removed, and 150 µl of DMSO was added. The absorbance was measured at 545 nm using an ELISA reader (Awareness, USA) (29). Finally, the IC 50 value was calculated for each compound, and these concentrations were used in the following.…”

Lamiaceae: An Insight on Their Anti-Allergic Potential and Its Mechanisms of Action

“…All these chemical constituents contribute to multidirectional pharmacological activities. Some of the remarkable bioactivities reported within this plant family are anti-allergic (Malik et al, 2003; Makino et al, 2003; Kim et al, 2009), anti-inflammatory (Borges et al, 2018), antimicrobial (Khoury et al, 2016; Cocan et al, 2018), free radical scavenging (Khaled-Khodja et al, 2014; Politeo et al, 2018), antinociceptive (Hwang et al, 2018; Uritu et al, 2018), anti-cancer activities (Nguyen et al, 2018; Sajjadi et al, 2018), etc. Many pharmacological activities of the Lamiaceae family have been widely studied and investigated.…”