title: New isoflavones from Gynandriris sisyrinchium and their antioxidant and cytotoxic activities.
abstract: 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; β-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 β-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.
authors.affiliation: Department of Chemistry, Faculty of Science, Yarmouk University, Irbid, Jordan. Electronic address: mahmoud.qudah@yu.edu.jo.
authors.forename: Mahmoud A
authors.initials: MA
authors.lastname: Al-Qudah
authors.affiliation: Department of Basic Medical Sciences, King Saud Bin Abdulaziz University for Health Sciences, and King Abdullah International Medical Research Center (KAIMRC), Riyadh, Saudi Arabia.
authors.forename: Ayman M
authors.initials: AM
authors.lastname: Saleh
authors.affiliation: Department of Applied Sciences, Faculty of Engineering Technology, Al-Balqa Applied University, Marka, Jordan. Electronic address: rhhjaber@yahoo.com.
authors.forename: Hala I
authors.initials: HI
authors.lastname: Al-Jaber
authors.affiliation: Department of Chemistry, Faculty of Science, Yarmouk University, Irbid, Jordan.
authors.forename: Hasan I
authors.initials: HI
authors.lastname: Tashtoush
authors.affiliation: Department of Biological Sciences, Faculty of Science, Yarmouk University, Irbid, Jordan.
authors.forename: Jamil N
authors.initials: JN
authors.lastname: Lahham
authors.affiliation: Department of Chemistry, Faculty of Science, The University of Jordan, Amman, Jordan.
authors.forename: Musa H
authors.initials: MH
authors.lastname: Abu Zarga
authors.affiliation: Department of Pharmaceutical Sciences, Faculty of Pharmacy, The University of Jordan, Amman, Jordan.
authors.forename: Fatma U
authors.initials: FU
authors.lastname: Afifi
authors.affiliation: Department of Chemistry, Faculty of Science, Yarmouk University, Irbid, Jordan.
authors.forename: Sultan T
authors.initials: ST
authors.lastname: Abu Orabi
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology*; D000975:Antioxidants / Q000302:isolation & purification / Q000494:pharmacology*; D017209:Apoptosis; D018922:HL-60 Cells; D006801:Humans; D027621:Iridaceae / Q000737:chemistry*; D007529:Isoflavones / Q000302:isolation & purification / Q000494:pharmacology*; D007597:Jordan; D015394:Molecular Structure
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D007529:Isoflavones
keywords: 3′-methyl tenuifone; Antioxidant; Bis-isoflavones; Cytotoxicity; Gynandriris sisyrinchium; Iridaceae