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New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of Panax notoginseng.

ABSTRACT: Background:Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China. Methods:The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities. Results and Conclusion:Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3?,6?,12?,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6?,12?,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3?,6?,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12?,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6?-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12-16 and 19-25) were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13, and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.

SUBMITTER: Shang JH

PROVIDER: S-EPMC7195571 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of <i>Panax notoginseng</i>.

Shang Jia-Huan JH Sun Wen-Jie WJ Zhu Hong-Tao HT Wang Dong D Yang Chong-Ren CR Zhang Ying-Jun YJ

Journal of ginseng research 20190206 3

<h4>Background</h4>Root rot is a serious destructive disease of <i>Panax notoginseng</i>, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China.<h4>Methods</h4>The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic ac ...[more]

PMID: 32372862

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Project description:MicroRNAs (miRNAs) are small, non-coding RNAs that are important regulators of gene expression, and play major roles in plant development and their response to the environment. Root extracts from Panax notoginseng contain triterpene saponins as their principal bioactive constituent, and demonstrate medicinal properties. To investigate the novel and conserved miRNAs in P. notoginseng, three small RNA libraries constructed from 1-, 2-, and 3-year-old roots in which root saponin levels vary underwent high-throughput sequencing.P. notoginseng roots, purified from 1-, 2-, and 3-year-old roots, were extracted for RNA, respectively. Three small libraries were constructed and subjected to next generation sequencing.Sequencing of the three libraries generated 67,217,124 clean reads from P. notoginseng roots. A total of 316 conserved miRNAs (belonging to 67 miRNA families and one unclassified family) and 52 novel miRNAs were identified. MIR156 and MIR166 were the largest miRNA families, while miR156i and miR156g showed the highest abundance of miRNA species. Potential miRNA target genes were predicted and annotated using Cluster of Orthologous Groups, Gene Ontology, and Kyoto Encyclopedia of Genes and Genomes. Comparing these miRNAs between root samples revealed 33 that were differentially expressed between 2- and 1-year-old roots (8 increased, 25 decreased), 27 differentially expressed between 3- and 1-year-old roots (7 increased, 20 decreased), and 29 differentially expressed between 3- and 2-year-old roots (8 increased, 21 decreased). Two significantly differentially expressed miRNAs and four miRNAs predicted to target genes involved in the terpenoid backbone biosynthesis pathway were selected and validated by quantitative reverse transcription PCR. Furthermore, the expression patterns of these six miRNAs were analyzed in P. notoginseng roots, stems, and leaves at different developmental stages.This study identified a large number of P. notoginseng miRNAs and their target genes, functional annotations, and gene expression patterns. It provides the first known miRNA profiles of the P. notoginseng root development cycle.

Dataset Information

New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of Panax notoginseng.

Publications

New hydroperoxylated and 20,24-epoxylated dammarane triterpenes from the rot roots of <i>Panax notoginseng</i>.

Similar Datasets

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