A new bioactive monoterpene-flavonoid from Satureja khuzistanica

Abstract

A new monoterpene-flavonoid, saturejin (3'-(2,5-dihydroxy-p-cymene) 5,7,4'-trihydroxy flavone) (4), together with twelve known flavonoids consist of two flavanonols (aromadendrin (8) and taxifolin (12)), two flavanones (naringenin (3) and 5,7,3',5'-tetrahydroxy flavanone (9)) and eight flavones (xanthomicrol (1), acacetin (2), cirsimaritin (5), 7-methoxy luteolin (6), apigenin (7), cirsilineol (10), diosmetin (11) and 6-hydroxyluteolin 7,3'-dimethyl ether (13)), were isolated from an ethyl acetate extract and identified for the first time in the dried aerial parts of Satureja khuzistanica Jamzad, an endemic medicinal plant traditionally used as dental anesthetic, oral antiseptic and anti-inflammatory among the nomadic inhabitants of southwestern Iran. The structures of these compounds were determined using the usual spectroscopic methods including 2D-NMR and MS analyses. Saturejin showed a significant β-glucosidase inhibitory activity at concentration of 10 μg as well as positive antioxidant activity at the amount of 1 μg. These results could be correlated with the in vitro and in vivo anti-inflammatory, anti-oxidant and anti-diabetic properties reported from this medicinal plant. Similar activities were also described for some of the other isolated compounds.

Keywords: 3′-(2,5-dihydroxy-p-cymene)5,7,4′-trihydroxyflavone; 6-hydroxyluteolin 7 3′-dimethyl ether (PubChem CID: 10359254); Acacetin (PubChem CID:5280442); Antioxidant activity; Apigenin (PubChem CID: 5280443); Aromadendrin (PubChem CID: 122850); Cirsilineol (PubChem CID: 162464); Cirsimaritin (PubChem CID: 188323); Diosmetin (PubChem CID: 5281612); Monoterpene–flavonoid; Naringenin (PubChem CID: 932); Satureja khuzistanica; Saturejin; Taxifolin (PubChem CID: 439533); Xanthomicrol (PubChem CID:73207); β-Glucosidase inhibitory activity.