title: New steroidal saponins from the bulbs of Lilium brownii var. viridulum.
abstract: Phytochemical investigation of the bulbs of Lilium brownii var. viridulum led to the isolation of seven new steroidal saponins (1-7), along with eight known analogues (8-15). The new steroidal saponins were identified as 27-O-[(3S)-3-O-β-D-glucopyranosyl 3-methylglutaroyl]isonarthogenin 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (1), (24S,25S)-3β,17α,24-trihydroxy-5α-spirostan-6-one 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (2), tenuifoliol 3-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (3), 26-O-β-D-glucopyranosylnuatigenin (4), 26-O-β-D-glucopyranosylnuatigenin 3-O-β-D-glucopyranoside (5), 26-O-β-D-glucopyranosylnuatigenin 3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]}-β-D-glucopyranoside (6), 26-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranosylnuatigenin 3-O-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (7), using a combination of spectroscopic evidence and chemical methods. The carbohydrate chain of a sugar linked to C-3 of the HMG group (3-hydroxy-3-methylglutarate) in compound 1 is rarely found in nature. Compound 2 possesses a new (24S,25S)-3β,17α,24-trihydroxy-5α-spirostan-6-one aglycon moiety. The disaccharide chain linked to C-26 hydroxy group of the furospirostanol in compound 7 has not been observed from natural sources.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China.
authors.forename: Xiao-Xiao
authors.initials: XX
authors.lastname: Hong
authors.forename: Jian-Guang
authors.initials: JG
authors.lastname: Luo
authors.forename: Chao
authors.initials: C
authors.lastname: Guo
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
mesh_terms: D000818:Animals; D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D006868:Hydrolysis; D027762:Lilium / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D018517:Plant Roots / Q000737:chemistry*; D012503:Saponins / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013256:Steroids / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D008070:Lipopolysaccharides; D012503:Saponins; D013256:Steroids; D009569:Nitric Oxide