title: New triterpenic acids from Uncaria rhynchophylla: chemistry, NO-inhibitory activity, and tandem mass spectrometric analysis.
abstract: Five new oleanane and ursane type triterpenes, namely uncarinic acids F-J (1-5), together with six known triterpenic acids (6-11) were isolated from the stems and hooks of Uncaria rhynchophylla. Structure elucidation of 1-5 was based on the integrated analyses of high-resolution MS data, 1D ((1)H NMR, (13)C NMR, DEPT) and 2D (HSQC, HMBC, ROESY) NMR spectra. Compounds 4, 10, and 11 exhibited weak inhibitory effects on LPS-induced NO production in RAW264.7 cells (with IC50 1.48, 7.01, and 1.89 μM, respectively) with dexamethasone (IC50 0.04 μM) and quercetin (IC50 0.86 μM) as the positive controls. 19-OH substituted oleanane triterpenic acids (1, 2, 5, 8) were prone to eliminate CH2O3, whereas those ursane-type encompassing 19-OH (3, 6, 7, 9, 4) were featured by preferred cleavage of H2O while performing the negative collision-induced MS/MS fragmentation on an LTQ/Orbitrap mass spectrometer.
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China.
authors.forename: Yi-bei
authors.initials: YB
authors.lastname: Zhang
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China.
authors.forename: Wen-zhi
authors.initials: WZ
authors.lastname: Yang
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China.
authors.forename: Chang-liang
authors.initials: CL
authors.lastname: Yao
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China.
authors.forename: Rui-hong
authors.initials: RH
authors.lastname: Feng
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China.
authors.forename: Min
authors.initials: M
authors.lastname: Yang
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China.
authors.forename: De-an
authors.initials: DA
authors.lastname: Guo
authors.affiliation: Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, PR China. Electronic address: wanyingwu@simm.ac.cn.
authors.forename: Wan-ying
authors.initials: WY
authors.lastname: Wu
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism; D009828:Oleanolic Acid / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D053719:Tandem Mass Spectrometry / Q000379:methods*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D032070:Uncaria / Q000737:chemistry*
chemical_list: D008070:Lipopolysaccharides; D014315:Triterpenes; D009569:Nitric Oxide; D009828:Oleanolic Acid
keywords: NO-inhibitory effect; Tandem mass spectrometric fragmentation; Uncaria rhynchophylla; Uncarinic acid