ABSTRACT
Three new spirostanol saponins were isolated from the EtOAc fraction of methanol extract from Tupistra chinensis rhizomes. Based on the detailed analysis of their 1D and 2D NMR spectra and chemical evidence, their structures were determined as 1ß-O-acetyl-spirost-5,25(27)-dien-3α-yl-O-ß-D-glucopyranoside (1), (25S)-1ß,2ß,5ß-trihydroxy-spirostane-3ß-yl-O-ß-D-glucopyranoside (2) and (25S)-1ß,2ß-dihydroxy-5ß-spirostane-3ß-yl-O-ß-D-xylopyranoside (3), respectively.
Subject(s)
Liliaceae/chemistry , Saponins/isolation & purification , Spirostans/isolation & purification , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Rhizome/chemistry , Saponins/chemistry , Spirostans/chemistry , TaiwanABSTRACT
A new pregnane glycoside, a dibenzylbutyrolactone lignan, 5-hydroxymatairesinol dimethyl ether, and three new flavonoids, including one 8-methylflavan-3-ol, and two 8-methylflavones, together with five known flavonoids and two known alkaloids were isolated from the rhizomes of Tupistra chinensis. The structures of all compounds were elucidated by spectral studies.
Subject(s)
Liliaceae/chemistry , Rhizome/chemistry , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Seven new compounds, including three new flavans [tupichinol A-C (1-3)], three new spirostanol sapogenins [tupichigenin D-F (4-6)], and one new pregnane genin [tupipregnenolone (7)], together with 18 known compounds, were isolated from the underground parts of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. The structures and relative stereochemistry of 1 and 9 were further confirmed by single-crystal X-ray crystallographic analysis. Compounds Delta(25(27))-pentrogenin, 10, and ranmogenin A showed 100%, 96%, and 80% inhibition, respectively, against human gastric tumor (NUGC) cells at a concentration of 50 microM. Delta(25(27))-pentrogenin showed 100% inhibition against human nasopharyngeal carcinoma (HONE-1) cells at a concentration of 50 microM.
