Parisvaniosides A–E, five new steroidal saponins from Paris vaniotii.

[Display omitted] • The rhizomes of Paris vaniotii were studied chemically for the first time. • Four new spirostanol saponins and one new furostanol saponin were obtained. • The first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B was isolated. • The saponins were evaluated for their inhibitory effects on the LPS-induced NO production in RAW264.7 macrophages. The species of Paris genus is a prolific source of structurally diverse steroidal saponins responsible for multivarious biological properties. The first phytochemical investigation on the steroidal saponin constituents from the rhizomes of Paris vaniotii Lévl. led to the discovery and structural characterization of four new spirostanol saponins, named parisvaniosides A-D (1 – 4), and one new furostanol glycoside, named parisvanioside E (5), along with eleven known analogues (6 – 16). Their structures were unambiguously established on the basis of extensive spectroscopic analysis and comparison with the reported spectroscopic data. Compound 1 is a rare spirostanol saponin sharing with a C-9/C-11 double bond and a peroxy group located between C-5 and C-8 of the aglycone, whereas 3 and 4 are unusual C-27 steroidal sapoins with hydroxyl/methoxyl at both C-5 and C-6. Furthermore, 5 is the first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B. All isolated saponins were evaluated for their anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW 264.7 macrophages. [ABSTRACT FROM AUTHOR]