Biochemical and biophysical properties of a novel homoisoflavonoid extracted from Scilla persica HAUSSKN

Scillapersicene: a new homoisoflavonoid with cytotoxic activity from the bulbs ofScilla persicaHAUSSKN

“…Previous investigations have illustrated that homoisoflavonoids are efficient cytotoxic agents (Nguyen et al 2006;Yen et al 2010;Hafez Ghoran et al 2014). The cellular mutability control by natural antimutagens can provide ways for preventing mutations that conceivably result in cancer as well as diseases caused by genotoxic agents.…”

“…The homoisoflavonoids showed the spots with orange, dark orange and red-orange colours on TLC by spraying anisaldehyde-H 2 SO 4 reagent followed by heating. The known compounds (2-6) were identified as 3-(3′,4′-dihydroxybenzyl)-5,8-dihydroxy-7-methoxychroman-4-one (2) (Adinolfi et al 1986), 3-(4′-hydroxybenzyl)-5,7-dihydroxy-6-methoxy-chroman-4-one or 3,9-dihydro-autumnalin (3) (Silayo et al 1999;Mutanyatta et al 2003;Nishida et al 2008), 3-(4′-hydroxybenzylidene)-5,7-dihydroxy-6-methoxychroman-4-one or autumnalin (4) (Silayo et al 1999), 3-(3′,4′-dihydroxybenzylidene)-5,8-dihydroxy-7-methoxychroman-4-one (5) (Mašterov et al 1991) and scillapersicone (6) (Hafez Ghoran et al 2014) based on the comparison of their spectroscopic data with those described in the literature. The known compounds (2-6) had previously been reported from Muscari armeniacum (2), S. nervosa and S. socialis (3 and 4), Muscari Racemosum (5) and S. persica (6).…”

“…The MEP, plotted in Supplementary Figure S2, show that oxygen atoms are negatively charged (red colour) while the hydrogen atoms of hydroxyl groups are positively charged (blue colour) in the molecule. In Supplementary Table S3, the quantum molecular descriptors for 1-6 such as amount of HOMO, LUMO, the energy gaps, Fermi energy level (E F ), global softness (S), hardness (η), electrophilicity index (ω), electronegativity (χ) and the maximum amount of electronic charge (∆N max ) were determined (Hafez Ghoran et al 2014). …”

“…According to previous studies on Scilla species, they contain alkaloids (Kato et al 2007), cardiac glycosides (Kamano & Petit 1974), triterpenoids (Mimaki et al 1993;Nishida et al 2008), triterpenoid glycosides (Arjune & Klar 2011;Ono et al 2011), nortriterpenoid glycosides (Ono et al 2011(Ono et al , 2013, eucosterol oligoglycosides (Lee et al 2002), stilbenoids (Bangani et al 1999;Nishida et al 2008), xanthone, lignin and phenylpropanoid glycoside (Nishida et al 2008), as well as homoisoflavanones (Heller & Tamm 1981;Bangani et al 1999;Silayo et al 1999;Mutanyatta et al 2003;Shim et al 2004;Nishida et al 2008;Hafez Ghoran et al 2014). These compounds possess antibacterial and antiangiogenic activities, and inhibit in vitro the growth of several microorganisms (Heller & Tamm 1981;Srinivas et al 2003;Shim et al 2004).…”

“…These compounds were mainly discovered from plants belonging to the Liliaceae family and a few other plant species (Sievänen et al 2010). Homoisoflavonoids have been reported to display multiple biological properties such as antioxidant activity (Siddaiah et al 2006;Zhou et al 2008), cytotoxic activity (Nguyen et al 2006;Yan et al 2012;Hafez Ghoran et al 2014), inhibition of platelet aggregation (Kou et al 2006), cough sedative (Ishibashi et al 2001), hyperglycemia (Choi et al 2004), anti-angiogenic (Shim et al 2004), anti-fungal (Srinivas et al 2003), anti-inflammatory, antiallergic, antihistaminic, angioprotective activities, and have been detected as potent phosphodiesterase inhibitors (Della Loggia et al 1989;Amschler et al 1996;Shim et al 2004). Many natural products have traditionally played a prominent role in drug discovery and were the basis of most early medicines (Grabley & Thiericke 1999;Buss et al 2003).…”