β-Carboline alkaloids from the stems of Picrasma quassioides

College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
Magnetic Resonance in Chemistry (Impact Factor: 1.18). 06/2010; 48(6):490-5. DOI: 10.1002/mrc.2602
Source: PubMed


Five new beta-carboline alkaloids, 6,12-dimethoxy-3-(2-hydroxylethyl)-beta-carboline (1), 3,10-dihydroxy-beta-carboline (2), 6,12-dimethoxy-3-(1-hydroxylethyl)-beta-carboline (3), 6,12-dimethoxy-3-(1,2-dihydroxylethyl)-beta-carboline (4), and 6-methoxy-3-(2-hydroxyl-1-ethoxylethyl)-beta-carboline (5), and two new natural products, 6-methoxy-12-hydroxy-3-methoxycarbonyl-beta-carboline (6) and 3-hydroxy-beta-carboline (7) were isolated from the stems of Picrasma quassioides along with 16 known beta-carboline alkaloids (8-23). The structures of new compounds were determined by extensive spectroscopic analyses, and the 1D and 2D NMR data of compounds 6, 7 and 10 were reported for the first time. The bioassays showed that only compounds 14 and 16 could enhance the differentiation of 3T3-L1 preadiocytes accompanied by secretion of adiponectin proteins among these 23 compounds.

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    ABSTRACT: A new dihydrobenzofuran-type neolignan, picrasmalignan A (1), and a new sesterterpene lactone, 2'-isopicrasin A (4), were isolated from the stems of Picrasma quassioides Bennet, along with four known compounds, comprising two neolignans, 2 and 3, a sesterterpene lactone, 5, and a flavonol, 6. The structures of these compounds were determined by detailed analysis of NMR and MS data, and comparison with the literature data. Compounds 1-6 were tested for their anti-inflammatory activity, and 1-3 and 6 showed potent inhibitory activities on nitric oxide, tumor necrosis factor-α, and interleukin-6 production in mouse monocyte-macrophage RAW 264.7 stimulated by lipopolysaccharide (LPS).
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    ABSTRACT: During further chemical and biological investigations of Picrasma quassioides BENNET, four new bis-β-carboline alkaloids, quassidines E-H (1-4), and three new β-carboline alkaloids, canthin-16-one-14-butyric acid (5), 3-(1,1-dimethoxylmethyl)-β-carboline (6), and 6,12-dimethoxy-3-formyl-β-carboline (7), were isolated from its anti-inflammatory CHCl(3)-soluble fraction. Structures of new compounds were elucidated and characterized by MS and NMR analysis. A plausible biogenetic pathway for quassidine E (1), the first bis-β-carboline alkaloid in which a canthin-6-one moiety and a β-carboline moiety were connected together by a single carbon-carbon bond from the nature, was proposed. Quassidines E-G (1-3) showed potent inhibitory activity on the production of nitric oxide (NO), tumor necrosis factor α (TNF-α), or interleukin 6 (IL-6) in mouse monocyte-macrophage RAW264.7 cells stimulated by lipopolysaccharide (LPS). Analysis of anti-inflammatory activity of all β-carboline and bis-β-carboline alkaloids from P. quassioides showed that the carbonyl groups or double carbon-carbon bonds at C-14 for β-carbolines and C-14' for bis-β-carbolines were bioactive groups for their in vitro anti-inflammatory activity. Structure-activity relationship of these compounds on inhibitory activity of the three inflammatory cytokines was discussed.
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    ABSTRACT: A simple and sensitive method was developed and validated for profiling and simultaneous quantitation of seven alkaloids (6-hydroxy-β-carboline-1-carboxylic acid, β-carboline-1-carboxylic acid, β-carboline-1-propanoic acid, 3-methylcanthin-5,6-dione, 5-hydroxy-4-methoxycanthin-6-one, 1-methoxycarbony-β-carboline, and 4,5-dimethoxycanthin-6-one) in Picrasma quassioide grown in different locations by high-performance liquid chromatography with photodiode array detection. The analysis was conducted on a Phenomenex Gemini C(18) column at 35°C with mobile phase of 25 mM aqueous ammonium acetate (pH 4.0, adjusted by glacial acetate acid) and acetonitrile. A common fingerprint chromatograph under 254 nm consisting of 27 peaks was constructed for the evaluation of the similarities among 31 P. quassioide samples. Samples from Guangdong and Guangxi Provinces were found to be within group linkage and showed significant difference from that of Jiangxi Province origin by using principal component analysis and hierarchical clustering analysis. In addition, the seven alkaloids were identified by electrospray ionization mass spectrometry and comparing with reference standards and literature data. All of them were determined simultaneously using the established HPLC method. This rapid and effective analytical method could be employed for quality assessment of P. quassioide, as well as pharmaceutical products containing this herbal material.
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