Browse
Submit Data
Databases
API
Help

Dataset Information

13 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Linderaggrenolides A-N, Oxygen-Conjugated Sesquiterpenoid Dimers from the Roots of Lindera aggregata.

ABSTRACT: Linderaggrenolides A-N (1-14), 14 new lindenane sesquiterpenoid dimers with oxygen bridges were isolated from the roots of Lindera aggregata. Their structures were elucidated on the basis of comprehensive spectroscopic data analysis, with the absolute configurations established by empirical approaches, electronic circular dichroism calculations, and X-ray crystallography. Compounds 8 and 9 were found to exhibit significant transforming growth factor-? inhibitory activity, with IC₅₀ values of 25.91 and 21.52 ?M, respectively.

SUBMITTER: Liu X

PROVIDER: S-EPMC7931382 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Linderaggrenolides A-N, Oxygen-Conjugated Sesquiterpenoid Dimers from the Roots of Lindera aggregata.

Liu Xin X Fu Jing J Yang Ji J Huang Ancheng C AC Li Run-Feng RF Bai Li-Ping LP Liu Liang L Jiang Zhi-Hong ZH Zhu Guo-Yuan GY

ACS omega 20210216 8

Linderaggrenolides A-N (1-14), 14 new lindenane sesquiterpenoid dimers with oxygen bridges were isolated from the roots of Lindera aggregata. Their structures were elucidated on the basis of comprehensive spectroscopic data analysis, with the absolute configurations established by empirical approaches, electronic circular dichroism calculations, and X-ray crystallography. Compounds 8 and 9 were found to exhibit significant transforming growth factor-β inhibitory activ ...[more]

PMID: 33681628

Similar Datasets

Lindera cyclopentenedione intermediates from the roots of Lindera aggregata.

Project description:Chromatographic fractionation of the roots of Lindera aggregata has led to the isolation of three new monomers of Lindera cyclopentenedione derivatives (1-3), a pair of new enantiomers of bi-linderone derivatives (4a/4b), and six known Lindera cyclopentenediones (5-8 and 9a/9b). Their structures were determined by NMR and MS data. The absolute configurations of the new bi-linderone derivative enantiomers (4a/4b) were determined by ECD calculation. (±)-Lindepentone A (1) presents the novel skeleton of 3,5-dioxocyclopent-1-enecarboxylate. Lindoxepines A (2) and B (3) present an unprecedented oxepine-2,5-dione derivative skeleton, which may be enlightening for the in vivo biosynthesis of the monomers of Lindera cyclopentenediones. A possible biosynthetic pathway for 1 and a plausible biosynthetic pathway from stilbenes to Lindera cyclopentenediones via the key intermediates 2 and 3 were postulated. The inhibitory activity of these compounds against three microorganisms was also evaluated.

| S-EPMC9080501 | biostudies-literature

Lindera aggregata

Project description:Plastome sequences help to improve the systematic position of trinerved Lindera species in the family Lauraceae

| PRJNA559765 | ENA

Lindera aggregata

Project description:Lindera aggregata Genome sequencing and assembly

| PRJNA728200 | ENA

Lindera aggregata

Project description:Lindera aggregata overview

| PRJNA656337 | ENA

Development of 20 chloroplast microsatellite primers in wuyao (Lindera aggregata, Lauraceae).

Project description:Premise of the studyTo investigate the population genetics and evolutionary history of wuyao (Lindera aggregata, Lauraceae) and other Lindera species, polymorphic chloroplast microsatellite (cpSSR) primers were developed.Methods and resultsThe complete chloroplast genome of L. glauca was used to design 74 primers for L. aggregata. Agarose gel electrophoresis and Sanger sequencing were used to select 20 polymorphic primers. These primers were then tested in 70 individuals from three populations of L. aggregata. The number of alleles ranged from two to four, and the unbiased haploid diversity index ranged from 0.457 to 0.685. Up to 17 primers successfully amplified in four other Lindera species: L. prattii, L. chunii, L. lungshengensis, and L. pulcherrima var. hemsleyana.ConclusionsThe 20 primers reported here can potentially be used for future genetic studies of L. aggregata and other Lindera species.

| S-EPMC6711346 | biostudies-literature

WUYAO-Lindera aggregata (Sims) Kosterm.

Project description:WUYAO-Lindera aggregata (Sims) Kosterm. For analysis the raw and processed Lindera aggregata (Sims) Kosterm. 2022.10.17

2023-02-06 | MSV000091210 | MassIVE

A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers.

Project description:The dimeric lindenane sesquiterpenoids are mainly isolated from the plants of Chloranthaceae family. Structurally, they have a crowded molecular scaffold decorated with more than 11 stereogenic centers. Here we report divergent syntheses of eight dimeric lindenane sesquiterpenoids, shizukaols A, C, D, I, chlorajaponilide C, multistalide B, sarcandrolide J and sarglabolide I. In particular, we present a unified dimerization strategy utilizing a base-mediated thermal [4 + 2] cycloaddition between a common furyl diene, generated in situ, and various types of dienophiles. Accordingly, all the three types of lindenane [4 + 2] dimers with versatile biological activities are accessible, which would stimulate future probing of their pharmaceutical potential.

| S-EPMC6478710 | biostudies-literature

New guaiane-type sesquiterpenoid dimers from Artemisia atrovirens and their antihepatoma activity.

Project description:Leading by cytotoxicity against HepG2 cells, bioactivity-guided fractionation of the EtOAc fraction from Artemisia atrovirens led to the isolation of 18 new guaianolide dimers, artematrolides A-R and lavandiolides A, B, C, H, and J. Eight compounds (1, 4, 10, 12, 13, and 19-21) were unambiguously confirmed by the single-crystal X-ray diffraction analyses, and the others were elucidated based on IR, UV, HRESIMS, 1D and 2D NMR experiments, and comparison of the experimental and calculated ECD data. Structurally, all of them were [4 + 2] Diels-Alder adducts of two monomeric guaianolides. The isolates were evaluated for their cytotoxicity against three human hepatoma cell lines, and 19 compounds demonstrated cytotoxicity against HepG2, SMMC-7721, and Huh7 cell lines. Especially, compounds 1, 12, 14, and 15 exhibited cytotoxicity with IC50 values of 4.4, 3.8, 7.6, and 6.7 μmol/L (HepG2), 9.6, 4.6, 6.6, and 6.0 μmol/L (SMMC-7721), and 7.6, 4.5, 6.9, and 5.6 μmol/L (Huh7), respectively. Notably, compound 12 showed the most promising activity against three human hepatoma cell lines and dose-dependently inhibited cell migration and invasion, induced G2/M cell cycle arrest and cell apoptosis in HepG2 cells, down-regulated the expression of BCL-2 and PARP-1, and activated PARP-1 to up-regulate the expression of cleaved-PARP-1.

| S-EPMC8245908 | biostudies-literature

Xyloplains A-F, six new guaiane-type sesquiterpenoid dimers from Xylopia vielana.

Project description:Six new guaiane dimers, xyloplains A-F (1-6), with connecting patterns through two direct C-C bonds (C-1 to C-3', C-2 to C-1'), were isolated from the roots of Xylopia vielana. Their structures were elucidated clearly using extensive analysis of 1D NMR and 2D NMR, combined with Cu-Kα X-ray diffraction and circular dichroism (CD) experiments. In additon, all of the isolates were tested for anti-inflammatory activity by measuring the amount of nitric oxide produced. To our delight, compounds 2 and 6 exhibited moderate inhibitory activity against the production of nitric oxide with IC50 value of 34.5 and 31.1 μM, respectively, in RAW264.7 cells stimulated by LPS.

| S-EPMC9082531 | biostudies-literature

Phytotoxicity, Morphological, and Metabolic Effects of the Sesquiterpenoid Nerolidol on Arabidopsis thaliana Seedling Roots.

Project description:Natural herbicides that are based on allelopathy of compounds, can offer effective alternatives to chemical herbicides towards sustainable agricultural practices. Nerolidol, a sesquiterpenoid alcohol synthesized by many plant families, was shown to be the most effective allelopathic compound in a preliminary screening performed with several other sesquiterpenoids. In the present study, Arabidopsis thaliana seedlings were treated for 14 d with various cis-nerolidol concentrations (0, 50, 100, 200, 400, and 800 µM) to investigate its effects on root growth and morphology. To probe the underlying changes in root metabolome, we conducted untargeted gas chromatography mass spectrometry (GC-MS) based metabolomics to find out the specificity or multi-target action of this sesquiterpenoid alcohol. Oxidative stress (measured as levels of H2O2 and malondialdehyde (MDA) by-product) and antioxidant enzyme activities, i.e., superoxide dismutase (SOD) and catalase (CAT) were also evaluated in the roots. Nerolidol showed an IC50 (120 µM), which can be considered low for natural products. Nerolidol caused alterations in root morphology, brought changes in auxin balance, induced changes in sugar, amino acid, and carboxylic acid profiles, and increased the levels of H2O2 and MDA in root tissues in a dose-dependent manner. Several metabolomic-scale changes induced by nerolidol support the multi-target action of nerolidol, which is a positive feature for a botanical herbicide. Though it warrants further mechanistic investigation, nerolidol is a promising compound for developing a new natural herbicide.

| S-EPMC7650555 | biostudies-literature