title: Two new dihydroamentoflavone glycosides from Cycas revoluta.
abstract: Phytochemical investigation of the ethyl acetate extract of Cycas revoluta Thunb. leaflets afforded five compounds including two new dihydroamentoflavone glucosides, (2S)-I-(2,3)-dihydro-I-7-O-β-D-glucopyranosylamentoflavone (1) and (2S)-I-(2,3)-dihydro-I-7,II-7-di-O-β-D-glucopyranosylamentoflavone (2), in addition to the known compounds prunin (3), vitexin-2″-rhamnoside (4) and protocatechuic acid (5). Compounds (3) and (4) being reported for the first time in this plant. The structures of these compounds were established by the detailed analysis of their spectroscopic data, mainly 1D NMR, 2D NMR, CD and HR-MSD-TOF. The ethyl acetate extract showed weak cytotoxicity against HepG2 (IC50 = 207.6 μg/mL) and RAW 264.2 cells (IC50 = 160.8 μg/mL). Compound 4 showed significant activity towards Leishmania donavani (IC50 = 13.8 μM, IC90 = 34.6 μM). The isolated compounds showed weak antimicrobial activity (IC50>10 μg/mL).
authors.affiliation: a Department of Pharmacognosy , School of Pharmacy, Beni Suef University , Beni Suef , 62514 , Egypt.
authors.forename: Abeer
authors.initials: A
authors.lastname: Moawad
authors.forename: Mona
authors.initials: M
authors.lastname: Hetta
authors.forename: Jordan K
authors.initials: JK
authors.lastname: Zjawiony
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Mohamed
authors.initials: M
authors.lastname: Hifnawy
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047310:Apigenin / Q000737:chemistry / Q000302:isolation & purification*; D001232:Aspergillus fumigatus / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D029784:Cycas / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D047309:Flavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D062385:Hydroxybenzoates; D007893:Leishmania donovani / Q000187:drug effects; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D015269:Mycobacterium avium Complex / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D010695:Phlorhizin / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D011550:Pseudomonas aeruginosa / Q000187:drug effects
chemical_list: C000590580:(2S)-I-(2,3)-dihydro-I-7,II-7-di-O-beta-D-glucopyranosylamentoflavone; C000590579:(2S)-I-(2,3)-dihydro-I-7-O-beta-D-glucopyranosylamentoflavone; D000981:Antiprotozoal Agents; D047309:Flavones; D005960:Glucosides; D062385:Hydroxybenzoates; C506622:prunin; C021329:vitexin rhamnoside; C009091:protocatechuic acid; D047310:Apigenin; D010695:Phlorhizin