Alpha-pyrone glycosides fromScutellaria salviifoliaBenth

Abstract

Scutellaria salviifolia Benth. is an endemic species growing in Turkey that belongs to the family Lamiaceae. As a result of a phytochemical study on the aerial parts of S. salviifolia Benth., two new and 10 known compounds were isolated from the aqueous fraction of methanolic extract. The new compounds are methylα-pyrone glucosides, 3,4-dihydroxy-6-methylpyran-2-one 3-Oβ-glucopyranoside (=scusalvioside A, 1), and 3,4-dihydroxy-6-methylpyran-2-one 3-Oβ-(6 ′-O-E-caffeoyl) glucopyranoside (=scusalvioside B, 2) with new skeletal structures. Along with them, 3 phloroglucinol glucosides [phlorin (3), tadehaginoside (4), and 6 ′′-O-Zp-coumaroyl phloroglucinol-1-Oβglucopyranoside (5)], 6 flavonoids [apigenin (6), apigenin 5-Oβ-glucopyranoside (7), isoschaftoside (8), luteolin 7-Oβ-glucuronide (9), luteolin 4 ′-Oβ-glucopyranoside (10), and hispidulin (11)], and one phenylethanoid glycoside [martynoside (12)] were also isolated as known compounds. Compounds 2 and 8 were isolated as a mixture. Structure elucidations of the isolated compounds were carried out using UV, 1 H NMR, 13 C NMR, 2D NMR, and HR-ESI-MS analyses. Moreover, the phenylethanoid glycosides acteoside (13) and leucosceptoside A (14) were also detected in the plant by HPLC-DAD study. Tadehaginoside, 6 ′′-O-Zp-coumaroyl phloroglucinol-1-Oβ-glucopyranoside, and luteolin 4 ′-Oβ-glucopyranoside were reported for the first time from a Scutellaria species with this study.

Acta Biologica Cracoviensia s. Botanica

“…Subsequently, the identified compounds were attributed to apigenin and its derivatives, namely apigenin-O-neohesperidoside, apigenin-O-rutinoside, apigenin-O-glucoside, apigenin-dimethyl ether, glucopyranosyl-methylapigenin, vitexin and vitexin-O-rhamnoside, isovitexin, vicenin-2, and isoschaftoside. These findings are consistent with the approved reports on S. salvifolia Benth., S. hastifolia L., S. baicalensis, and S. incana (Nurul Islam et al, 2013;Lin et al, 2013;Xu et al, 2018;Dogan et al, 2019;Bardakci et al, 2019;massbank. eu;mona.fiehnlab.ucdavis.edu).…”

Biological evaluation of Stachys iberica subsp. stenostachya (Boiss.) Rech.f. and Scutellaria orientalis subsp. sosnowskyi (Takht.) Fed. growing in eastern Anatolia

“…In Turkish traditional medicine, the infusion and decoctions of the Scutellaria species are utilized as a tonic, hemostatic, and wound healing agent (Baytop, 1999;İçen et al, 2016). In regard to the phytochemical analysis of the species, over 300 compounds were identified, which showed the presence of different kinds of substances such as alkaloids, flavonoids, polysaccharides, phytosterols, iridoid glycosides, phenylethanoid glycosides, terpenes, and essential oil (Formisano et al, 2011;Mamadalieva et al, 2017;Doğan et al, 2019;Yılmaz et al, 2019;Zhao et al, 2019). A wide range of biological activities were observed in Scutellaria extracts, which was attributed to their diverse chemical composition (Zengin et al, 2019).…”