ABSTRACT
Five previously undescribed lanostane-type triterpenoids, including two triterpenoids with a rearranged side chain (applanoic acids E and F), one C21 nortriterpenoid (16,17-dehydroapplanone E), as well as two highly oxygenated lanostane triterpenoids (methyl applaniate B and applanoic acid G), were isolated from the fruiting bodies of Ganoderma applanatum (Pers.) Pat. Their structures were elucidated on the basis of spectroscopic analysis, X-ray crystallography and ECD data. Applanoic acid E, 16,17-dehydroapplanone E, and methyl applaniate B showed inhibitory effects on the release of NO by LPS-induced BV-2 cells.
Subject(s)
Ganoderma , Triterpenes , Fruiting Bodies, Fungal , Lipopolysaccharides , Molecular StructureABSTRACT
Twenty-nine lanostane triterpenoids (1-29) were obtained from the EtOH extract of fruiting bodies of the Ganoderma curtisii. Among them, compound 1 was a new lanostane triterpenoid and compounds 2-5 were isolated from the genus Ganoderma for the first time and their structures were unambiguously identified in this work. The NMR data of the four known lanostane triterpenoids (2-5) were reported for the first time because their structures were all tentatively characterized by interpreting the MS data from the methanol extract of Ganoderma lucidum or from the metabolites in rat bile after oral administration of crude extract of the fruiting bodies of G. lucidum using fragmentation rules. Their anti-inflammatory activities were tested by measuring their inhibitory effects on nitric oxide (NO) production in BV-2 microglia cells activated by lipopolysaccharide. Their IC50 values were in a range from 3.65±0.41 to 28.04±2.81µM.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Ganoderma/chemistry , Lipopolysaccharides/antagonists & inhibitors , Microglia/drug effects , Nitric Oxide/antagonists & inhibitors , Triterpenes/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Cell Line , Cell Survival/drug effects , Dose-Response Relationship, Drug , Lipopolysaccharides/pharmacology , Mice , Molecular Structure , Nitric Oxide/biosynthesis , Rats , Structure-Activity Relationship , Triterpenes/chemistry , Triterpenes/isolation & purificationABSTRACT
Two new flavonoid glycosides were isolated from the aerial parts of Nervilia fordii by various chromatographies such as D101 macroporous resin, ODS and preparative HPLC chromatographic techniques. Their structures were elucidated as rhamnocitrin-3-O-ß-glucopyranosyl-4'-O-ß-galactosyl-(1â3)-glucopyranoside(1) and 7,3'-di-O-methylquercetin-4'-O-[ß-galactosyl-(1â3)-ß-glucopyranosyl]-3-O-ß-glucopyranoside(2) on the basis of extensive spectroscopic analyses, including 1D-, 2D-NMR, HR-ESI-MS and analytical hydrolysis.
Subject(s)
Flavonoids/isolation & purification , Glycosides/isolation & purification , Orchidaceae/chemistry , Chromatography, High Pressure Liquid , Drugs, Chinese Herbal/chemistry , Hydrolysis , Molecular StructureABSTRACT
To study the chemical constituents of Nervilia fordii (Hance) Schltr., various chromatographic methods were used, including D101 macroporous resin, silica gel, ODS and preparative HPLC chromatographic techniques. A new labdane diterpenoid glycoside named as nervilifordoside A was isolated from 60% EtOH extract of Nerviliafordii. The structure of compound 1 was elucidated as 12, 17-epoxy-3-hydroxy-17-methoxy-labdan-13-en-16, 15-olide 3-O-alpha-rhamnopyranosyl-(1 --> 2)-O-beta-glucopyranoside on the basis of HR-MS, 1D and 2D NMR spectroscopic data as well as chemical methods.
