Glycosides from the Aerial Parts of Patrinia villosa

Joo Young Lee, Ju Sun Kim, Yeong Shik Kim, Sam Sik Kang
2013 Chemical and pharmaceutical bulletin  
An investigation of the Korean medicinal plant Patrinia villosa (THUNB.) JUSS. (Valerianaceae) led to the isolation of two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds including three flavonoid glycosides and three iridoid glycosides. The structures of the new compounds were elucidated based on analysis of their one dimensional (1D)-and 2D-NMR
more » ... tra along with their mass spectrometric data and the results of acid hydrolysis. The genus Patrinia (Valerianaceae) consists of about 20 species, four of which, P. scabiosaefolia FISCH., P. saniculaefolia HEMSL., P. rupestris JUSS. and P. villosa (THUNB.) JUSS. are distributed throughout Korea. 1) The whole plants have traditionally been used for inflammation, wound healing, ascetics, and abdominal pain after childbirth. 2,3) Previous phytochemical research on Patrinia villosa showed dominant presence of various types of iridoids, 4-6) and flavonoids 7-18) as well as steroids and triterpenoids, 8, 18, 19) and saponins. 8) Our previous phytochemical research on the genus mainly focused on P. scabiosaefolia and P. saniculaefolia and led to the isolation of a series of iridoids 2) and saponins. 3) Modern pharmacological research has demonstrated that P. villosa has broad pharmacological activity, including antitumor, anti-inflammatory, and antioxidant effects. 7,20-22) Therefore, we conducted phytochemical studies on P. villosa and resulted in the isolation of two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds. The structures were determined using spectroscopic methods including one dimensional (1D)and 2D-NMR spectra along with their mass spectroscopic data and the results of acid hydrolysis. Here, we describe the structure elucidation of the new compounds 1-5. The dried aerial parts of P. villosa were crushed and extracted with MeOH. The concentrated extract was suspended in H 2 O and successively extracted with hexane, EtOAc and BuOH. The BuOH extract was subjected to sequential column chromatography over silica gel, Sephadex LH-20 and RP-18 gel to yield two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds that included three iridoid glycosides, loganin (6), 23) valerosidate (7), 24,25) and loganic acid (11), 23) and three flavonoid glycosides, kaempferol 3-O-4‴acetylrhamninoside (8), 26) catharticin (9), 26) and kaempferol 3-O-rhamninoside (10). 8,26) Known compounds were identified by detailed 1D-and 2D-NMR analyses, comparison of their FAB-MS and spectral data with those reported in literature. Patriviloside 1 (1) was isolated as a yellow amorphous powder and its molecular formula was established as C 36 H
doi:10.1248/cpb.c13-00306 pmid:23800854 fatcat:ipnavfxlanh2hmvzldycyiytza