Scillapersicene: a new homoisoflavonoid with cytotoxic activity from the bulbs of Scilla persica HAUSSKN

Salar Hafez Ghoran, Soodabeh Saeidnia, Esmaeil Babaei, Fumiyuki Kiuchi, Hidayat Hussain

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

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 IC<inf>50</inf> 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.

Original languageEnglish
JournalNatural Product Research
DOIs
Publication statusAccepted/In press - 2015 Jun 30

Keywords

  • AGS
  • B3LYP
  • cytotoxic activity
  • homoisoflavonoid
  • Liliaceae
  • Scilla persica
  • Scillapersicene

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Analytical Chemistry
  • Organic Chemistry

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