title: Scillapersicene: a new homoisoflavonoid with cytotoxic activity from the bulbs of Scilla persica HAUSSKN.
abstract: The phytochemical investigation of Scilla persica HAUSSKN bulbs led to the isolation of a novel homoisoflavonoid that named Scillapersicene (1) and identified as 3-(3',4'-dihydroxybenzylidene)-8-hydroxy-5,7-dimethoxychroman-4-one along with five known homoisoflavonoids 2-6, whose structures were elucidated using HRFAB-MS, 1D and 2D NMR spectroscopic data. The known compounds were identified as 3-(3',4'-dihydroxybenzyl)-5,8-dihydroxy-7-methoxychroman-4-one (2), 3,9-dihydro-autumnalin (3), autumnalin (4), 3-(3',4'-dihydroxybenzylidene)-5,8-dihydroxy-7-methoxychroman-4-one (5) and scillapersicone (6). All compounds obtained, expect 2 and 4, showed strong cytotoxic activity against AGS cell line. The toxicity on AGS cell line was measured by 1, 3, 5 and 6 with IC50 values of 8.4, 30.5, 10.7 and 24.2 μM, respectively. In addition, the physico-chemical properties of these natural compounds were optimised using density functional method (B3LYP) with standard 6-311+G* basis set. These natural products have low-energy gaps between the first ionisation potentials and highest occupied molecular orbital. In conclusion, the low-energy gap could cause reason for cytotoxic activity of homoisoflavonoids.
authors.affiliation: a Faculty of Basic Sciences, Department of Chemistry , Golestan University , Gorgan 4913815739 , Iran.
authors.forename: Salar
authors.initials: S
authors.lastname: Hafez Ghoran
authors.affiliation: b Faculty of Pharmacy, Medicinal Plants Research Center , Tehran University of Medical Sciences , Tehran 1417614411 , Iran.
authors.forename: Soodabeh
authors.initials: S
authors.lastname: Saeidnia
authors.affiliation: c Department of Animal Biology, School of Natural Sciences , University of Tabriz , Tabriz , Iran.
authors.forename: Esmaeil
authors.initials: E
authors.lastname: Babaei
authors.affiliation: d Faculty of Pharmacy, Department of Pharmaceutical Sciences , Keio University , Tokyo , Japan.
authors.forename: Fumiyuki
authors.initials: F
authors.lastname: Kiuchi
authors.affiliation: e UoN Chair of Oman's Medicinal Plants and Marine Natural Products , University of Nizwa , Nizwa , Sultanate of Oman.
authors.forename: Hidayat
authors.initials: H
authors.lastname: Hussain
mesh_terms: D001688:Biological Products / Q000032:analysis; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D004583:Electrons; D006801:Humans; D020128:Inhibitory Concentration 50; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology / Q000633:toxicity*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D031445:Scilla / Q000737:chemistry*
chemical_list: D001688:Biological Products; D007529:Isoflavones; C000619261:scillapersicene
keywords: AGS; B3LYP; Liliaceae; Scilla persica; Scillapersicene; cytotoxic activity; homoisoflavonoid