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1.
Chem Biodivers ; 16(2): e1800238, 2019 Feb.
Article in English | MEDLINE | ID: mdl-30176110

ABSTRACT

Zanthoxylum bungeanum extracts were prepared using seven solvents: water, methanol, ethanol, acetic acid, ethyl acetate, chloroform, and benzene. The volatile composition in the extracts was qualitatively analyzed using headspace solid-phase microextraction coupled with gas chromatography mass spectrometry detection, and the alkylamide composition was determined using high-performance liquid chromatography. The extract compositions differed with respect to the solvents. A total of 49 volatile components belonging to four groups, terpenoids, alcohols, esters, and ketones, were identified in the extracts. The Z. bungeanum extracts were either ester or terpenoid type, dominated by linalyl acetate. The extracts were divided into three distinct groups based on principal component analysis and hierarchical clustering analysis. Water, methanol, and ethanol extracts could be applied in the food and pharmaceutical industries.


Subject(s)
Antioxidants/isolation & purification , Plant Extracts/chemistry , Zanthoxylum/chemistry , Antioxidants/pharmacology , Cluster Analysis , Esters/analysis , Monoterpenes/analysis , Principal Component Analysis , Solvents/pharmacology , Terpenes/analysis , Volatilization
2.
Appl Plant Sci ; 6(6): e01157, 2018 Jun.
Article in English | MEDLINE | ID: mdl-30131899

ABSTRACT

PREMISE OF THE STUDY: The genus Zanthoxylum in the Rutaceae family of trees and shrubs has a long history of domestication and cultivation in Asia for both economic and medicinal purposes. However, many Zanthoxylum species are morphologically similar and are easily confused. This often leads to false authentication of source materials and confusion in herbal markets, hindering their safe utilization and genetic resource conservation. DNA barcoding is a promising tool for identifying plant taxa. METHODS: We used three candidate DNA barcoding regions (ITS2, ETS, and trnH-psbA) to identify 69 accessions representing 13 Chinese Zanthoxylum species. The discriminatory capabilities of these regions were evaluated in terms of PCR amplification success, intra- and interspecific divergence, DNA barcoding gaps, and identification efficiency using the BLAST and tree-building methods. RESULTS: ITS2 proved the most useful for discriminating Chinese Zanthoxylum species, with a correct identification rate of 100%, and this region also exhibited significantly higher intra- and interspecific divergence. DISCUSSION: Phylogenetic analysis confirmed that ITS2 has a powerful discriminatory ability both at and below the species level. We confirmed that ITS2 is a powerful barcoding region for identifying Chinese Zanthoxylum species, and will be useful for analyzing and managing Chinese Zanthoxylum germplasm collections.

3.
Mitochondrial DNA B Resour ; 3(1): 26-27, 2017 Dec 20.
Article in English | MEDLINE | ID: mdl-33474053

ABSTRACT

The Chinese pepper (Zanthoxylum simulans) is a flowering plant in the family Rutaceae, native to eastern China and Taiwan. Like many other members of the Rutaceae, it is an economically important aromatic crop known for its volatile oil and nutrition. We determined the complete chloroplast genome sequences for Z. simulans using IIumina sequencing. The Z. simulans chloroplast has a total length of 158,461 bp; it consists of a large single copy (LSC) region of 85,568 bp, a small single copy region (SSC) length of 17,603 bp, and an inverted region (IR) of 27,645 bp. The genome encodes 132 annotated genes, including 87 protein-coding genes, 37 tRNA, and 8 rRNA. The overall GC content of the Z. simulans chloroplast genome was 38.5%. A phylogenomic analysis revealed that Z. simulans are clustered with Z. bungeanum within the genus Zanthoxylum.

4.
Molecules ; 21(10)2016 Oct 23.
Article in English | MEDLINE | ID: mdl-27782100

ABSTRACT

Four new unsaturated aliphatic acid amides, named zanthoamides A-D (1-4), and eight known ones-tetrahydrobungeanool (5), ZP-amide A (6), ZP-amide B (7), ZP-amide C (8), ZP-amide D (9), ZP-amide E (10), bugeanumamide A (11), and (2E,7E,9E)-N-(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9-dodecatrienamide (12)-were isolated from the pericarps of Zanthoxylum bungeanum. The structures of these compounds were elucidated by extensive use of spectroscopic methods, including HRESIMS, 1D and 2D NMR analyses and comparison with previously reported data. Compound 4 contained a rare C6 fatty acid unit with an acetal group. Results revealed that compounds 1, 5, 6, and 12 showed inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages, with IC50values of 48.7 ± 0.32, 27.1 ± 1.15, 49.8 ± 0.38, and 39.4 ± 0.63 µM, respectively, while the other compounds were inactive (IC50 > 60 µM). They could contribute to the anti-inflammatory effects of Z. bungeanum by suppression of NO production.


Subject(s)
Amides/chemistry , Amides/pharmacology , Nitric Oxide/metabolism , Zanthoxylum/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Fatty Acids, Unsaturated/chemistry , Fatty Acids, Unsaturated/pharmacology , Lipopolysaccharides/pharmacology , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , RAW 264.7 Cells/drug effects
5.
Bioorg Med Chem Lett ; 26(2): 338-342, 2016 Jan 15.
Article in English | MEDLINE | ID: mdl-26707398

ABSTRACT

Eight isobutylhydroxyamides, including three new (1-3), qinbunamides A-C, and five known sanshools (4-8), ZP-amide A (4), ZP-amide B (5), ZP-amide E (6), ZP-amide C (7), and ZP-amide D (8), were isolated from the pericarps of cultivated Zanthoxylum bungeanum Maxim, cultivated in Qinling mountain area, Shaanxi, China. The structures of all compounds were determined on the basis of spectroscopic techniques, including 1D and 2D NMR analysis and comparison with previously reported data. Compounds 1 and 2 are the first example of isobutylhydroxyamides containing an ethoxy group, and compound 3 is a rare C11 fatty acid-containing sanshool existing in genus Zanthoxylum. The tested compounds enhanced nerve growth factor (NGF)-mediated neurite outgrowth (neurotrophic activity) in rat pheochromocytoma (PC12) cells, but were inactive in the inhibitory effects on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and growth of HCT116 cells at concentrations of 50µM.


Subject(s)
Amides/pharmacology , Fatty Acids, Unsaturated/pharmacology , Nerve Growth Factor/metabolism , Zanthoxylum/chemistry , Amides/chemistry , Amides/isolation & purification , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Fatty Acids, Unsaturated/chemistry , Fatty Acids, Unsaturated/isolation & purification , HCT116 Cells , Humans , Mice , PC12 Cells , Rats
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