Alpha-pyrone glycosides from Scutellaria salviifolia Benth

Authors : Zeynep Doğan, Kan’ichiro Ishiuchi, Toshiaki Makino, Iclal Saraçoğlu

Pages : 972-981

View : 25 | Download : 15

Publication Date : 9999-12-31

Article Type : Makaleler

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 methyl- -pyrone glucosides, 3,4-dihydroxy-6-methylpyran-2-one 3-O- -glucopyranoside (=scusalvioside A, 1), and 3,4-dihydroxy-6-methylpyran- 2-one 3-O- -(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-Z -p-coumaroyl phloroglucinol-1-O- - glucopyranoside (5)], 6 flavonoids [apigenin (6), apigenin 5-O- -glucopyranoside (7), isoschaftoside (8), luteolin 7- O- -glucuronide (9), luteolin 4′ -O- -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-Z -p-coumaroyl phloroglucinol-1-O- -glucopyranoside, and luteolin 4′ -O- -glucopyranoside were reported for the first time from a Scutellaria species with this study.
Keywords : Scutellaria species, methyl- -pyrone glucosides, scusalviosides A and B, phloroglucinol derivatives, flavonoids