ABSTRACT
Investigation of the chemical constituents of Salvia judaica growing wild in Jordan led to the isolation and identification of 15 known compounds. These included: luteolin-3'-methyl ether (1), indole-3-carboxyaldehyde (2), p-hydroxybenzaldehyde (3), tricin (4), apigenin (5), methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (6), methyl rosmarinate (7), rosmarinic acid (8), salvigenin (9), ß-sitosterol (10), 3ß, 28-dihydroxyurs-12-ene (11), cirsilineol (12), 2,3-dihydroxyurs-12-en-28-oic acid (13), ß-sitosteryl glucoside (14), and tormentic acid (15). Compounds 6 and 7 exhibited strong radical scavenging and chelating activities as compared to α-tocopherol and ascorbic acid, compound 7 showed a 2-fold greater antioxidant activity as compared to compound 6. Furthermore, low doses of compounds 6 and 7 were able to inhibit the growth of leukemic (HL-60, Jurkat, K562 and CCRF-SB) and solid tumor cells (MCF-7, MDA-MB-231 and Caco-2). Compound 7 showed a ca. 3-4-fold stronger cytotoxicity against the tested cells as compared to compound 6.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Chelating Agents/pharmacology , Salvia/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Caco-2 Cells , Cell Line, Tumor , Chelating Agents/chemistry , Cinnamates/chemistry , Cinnamates/pharmacology , Depsides/chemistry , Depsides/pharmacology , Drug Screening Assays, Antitumor , Flavones/chemistry , Flavones/pharmacology , Flavonoids/chemistry , Flavonoids/pharmacology , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Humans , Jordan , Molecular Structure , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Plants, Medicinal/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Rosmarinic AcidABSTRACT
Chemical investigation of Gynandriris sisyrinchium (L.) Parl growing in Jordan resulted in the isolation and characterization of a total of twelve compounds two of which are reported here for the first time in nature. These new compounds included the isoflavones; 3'-methyl tenuifone (2) and gynandrinone (5). In addition, ten known compounds including; ß-sitosterol (1), 7,3'-dimethoxy-5,6,4'-trihydroxyisoflavone (3), iristectorigenin (4), hispidulin (6), galangustin (7), 6-hydroxybiochanin A (8), ursolic acid (9), ladanetin (10), 4'-O-methylgenistein (11) and ß-sitosterol glucoside (12) are also reported here for the first time from G. sisyrinchium. The isolated compounds were characterized by different spectroscopic methods including NMR (1D and 2D), UV, IR and MS (HRESIMS and EIMS). The antioxidant and cytotoxic activities of isoflavones 2, 3 and 5 were investigated. Compound 3 showed the highest antioxidant activity (IC50=17.3µg/mL), as compared to compounds 5 and 2 (IC50=26.7 and 51.7µg/mL, respectively). The cytotoxic activity against the human promyelocytic leukemia HL-60 cells revealed that compound 2 was the most active (40µM). The results indicate that the cytotoxicity of compound 2 is mediated by apoptosis.
