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Selagintamarlin A: A Selaginellin Analogue Possessing a 1H-2-Benzopyran Core from Selaginella tamariscina.

ABSTRACT: Selagintamarlin A (1), a novel selaginellin analogue featuring the unique motif of 1H-2-benzopyran, a new selaginpulvilin E (2), together with eight known analogues were isolated from Selaginella tamariscina. Their structures were elucidated by extensive spectroscopic analyses. A plausible biosynthetic pathway of 1 was also postulated. Compound 1 showed remarkable inhibitory activity against phosphodiesterase-4 (PDE4D2), with an IC₅₀ value of 40 nM, which is 20-fold higher than that of the positive control (rolipram). Furthermore, compound 1 significantly inhibited tubulin polymerization.

SUBMITTER: Yao WN

PROVIDER: S-EPMC6044830 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Selaginella tamariscina

Project description:Selaginella tamariscina overview

| PRJNA532258 | ENA

Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring.

Project description:A new selaginellin named selaginellin O (1), along with three other known selaginellins (2-4) were isolated from Selaginella tamariscina (Beauv.) Spring. On the basis of spectroscopic analysis, the structure of selaginellin O was demonstrated to be 4-[(4'-hydroxy-4-formyl-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one. Compound 1, 2 and 3 exhibited appreciable cytotoxic activity against cultured HeLa cells (human cervical carcinoma cells), as well as significant antioxidant activity.

| S-EPMC3511026 | biostudies-literature

Haemostatic Nanoparticles-Derived Bioactivity of from Selaginella tamariscina Carbonisata.

Project description:High-temperature carbonisation is used to prepare many traditional Chinese medicine charcoal drugs, but the bioactive haemostatic substances of these medicines and their mechanisms are still unknown. This study developed and evaluated nanoparticles (NPs) derived from Selaginella pulvinate Carbonisata (STC) for the first time. The haemostatic effect of STC-NPs prepared at 300, 350, and 400 °C were investigated in mouse tail amputation and liver scratch experiments. STC-NPs obtained at 400 °C had the strongest haemostatic effect, and were accordingly characterised by ultraviolet-visible spectroscopy, fluorescence spectroscopy, Fourier transform infrared spectroscopy, transmission electron microscopy, high resolution transmission electron microscopy, X-ray diffractometry, and X-ray photoelectron spectroscopy. STC-NPs averaged 1.4-2.8 nm and exhibited a quantum yield of 6.06% at a maximum excitation wavelength of 332 nm and emission at 432 nm. STC-NPs displayed low toxicity against mouse monocyte macrophage RAW 264.7 cells by CCK-8 assay, and STC-NP treatment significantly shortened bleeding time in rat and mouse models. Coagulation assays showed that the haemostatic effects of STC-NPs were related to improving the fibrinogen and platelet contents, as well as decreasing the prothrombin time that resulted from stimulating extrinsic blood coagulation and activating the fibrinogen system. The STC-NPs had remarkable haemostatic effects in the tail amputation and liver scratch models; these effects may be associated with the exogenous coagulation pathway and activation of the brinogen system, according to the evaluation of the mouse coagulation parameters. This novel evaluation supports the material basis of STC use in traditional Chinese medicine, and this article is worthy of study by authors of clinical pharmacy.

| S-EPMC7036756 | biostudies-literature

Soluble Epoxide Hydrolase Inhibitory Activity of Selaginellin Derivatives from Selaginella tamariscina.

Project description:Selaginellin derivatives 1-3 isolated from Selaginella tamariscina were evaluated for their inhibition of soluble epoxide hydrolase (sEH) to demonstrate their potential for the treatment of cardiovascular disease. All selaginellin derivatives (1-3) inhibited sEH enzymatic activity and PHOME hydrolysis, in a dose-dependent manner, with IC50 values of 3.1 ± 0.1, 8.2 ± 2.2, and 4.2 ± 0.2 ?M, respectively. We further determined that the derivatives function as non-competitive inhibitors. Moreover, the predicted that binding sites and interaction between 1-3 and sEH were solved by docking simulations. According to quantitative analysis, 1-3 were confirmed to have high content in the roots of S. tamariscina; among them, selaginellin 3 exhibited the highest content of 189.3 ± 0.0 ?g/g.

| S-EPMC6331899 | biostudies-literature

Isolation, Structural Assignment of Isoselagintamarlin A from Selaginella tamariscina and Its Biomimetic Synthesis.

Project description:Isoselagintamarlin A (1), a selaginellin analogue featured a rare benzofuran unit, was isolated from Selaginella tamariscina. Its complete structural assignment was established through a combination of high-field NMR technique and biomimetic synthesis. Notably, isoselagintamarlin A (1) was successfully synthesized via sequential oxidations and intramolecular cyclization.

| S-EPMC6328423 | biostudies-literature

Ultrasonic-Assisted Ionic Liquid Extraction of Two Biflavonoids from <i>Selaginella tamariscina</i>.

Project description:Selaginella tamariscina, a traditional Chinese medicine, contains a variety of bioactive components, among which biflavonoids are the main active ingredients and have antioxidant, antitumor, and anti-inflammatory properties. In this study, ultrasonic-assisted ionic liquid extraction (UAILE) is used for the first time to extract two main biflavonoids (amentoflavone (AME) and hinokiflavone (HIN)) from S. tamariscina. A high-performance liquid chromatography method is used for the simultaneous determination of AME and HIN in S. tamariscina. Then, three novel ILs are synthesized for the first time by a one-step method using benzoxazole and three acids or acid salts as raw materials, and the structures of the synthesized ILs are characterized by elemental analysis, infrared spectroscopy, and NMR spectroscopy, as well as the thermal stability of the ILs is evaluated by thermogravimetric analysis. After screening the extraction effects of three benzoxazole ILs, three pyridine ILs, and three imidazole ILs, it is found that [Bpy]BF4 is the best and therefore selected as the extractant. The optimal extraction process is explored in terms of the yields of AME and HIN from S. tamariscina by a single-factor experiments and response surface analysis. Under the optimal level of each influencing factor (IL concentration of 0.15 mol/L, solid-liquid ratio of 1:12 g/mL, ultrasonic power of 280 W, ultrasonic time of 30 min, and three extraction cycles), the extraction rates of AME and HIN from S. tamariscina are 13.51 and 6.74 mg/g, respectively. Moreover, the recovery experiment of [Bpy]BF4 on the extraction of biflavonoids shows that the recovered IL can repeatedly extract targets six times and the extraction rate is about 90%, which indicates that the IL can be effectively reused. UAILE can effectively and selectively extract AME and HIN, laying the foundation for the application of S. tamariscina.

| S-EPMC7774283 | biostudies-literature

Identifying resurrection genes through the differentially expressed genes between Selaginella tamariscina (Beauv.) spring and Selaginella moellendorffii Hieron under drought stress.

Project description:Selaginella tamariscina (Beauv.) spring, a primitive vascular resurrection plant, can survive extreme drought and recover when water becomes available. To identify drought-inducible genes and to clarify the molecular mechanism of drought tolerance, a comparative transcriptional pattern analysis was conducted between S. tamariscina and Selaginella moellendorffii Hieron (drought sensitive). 133 drought related genes were identified, including 72 functional genes and 61 regulatory genes. And several drought responsive reactions, such as antioxidant activity, osmotic balance, cuticle defense and signal transduction were highlighted in S. tamariscina under drought. Notably, besides peroxidase, catalase and L-ascorbate oxidase genes, DEGs associated with phenylalanine metabolism and polyamine catabolism could be alternative ways to enhance antioxidant ability in S. tamariscina. DEGs related to soluble carbohydrate metabolism, late embryogenesis abundant protein (LEA) and aquaporin protein (AQP) confirmed that osmotic adjustment could resist drought during desiccation. DEGs involved in xyloglucan metabolic process, pectin metabolic process and cutin biosynthesis may also contribute to drought tolerance of S. tamariscina by cuticle defense. Drought-responsive genes encoding protein kinases, calcium sensors, transcription factors (TFs) and plant hormones also help to drought resistance of S. tamariscina. The preliminary validation experiments were performed and the results were consistent with our hypothetical integrated regulatory network. The results of this study provide candidate resurrection genes and an integrated regulatory network for further studies on the molecular mechanisms of stress tolerance in S. tamariscina.

| S-EPMC6853609 | biostudies-literature

Selaginella tamariscina isolate:ZC-2017

Project description:Selaginella tamariscina isolate:ZC-2017 Genome sequencing and assembly

| PRJNA416064 | ENA

A biomimetic semisynthesis enables structural elucidation of selaginellin U: a tautomeric cyclic alkynylphenol from Selaginella tamariscina.

Project description:Two new lactone-containing selaginellins T and U (1 and 2) together with eleven known selaginellin derivatives (3 and 7-16) were isolated from the whole plant of Selaginella tamariscina. The structure of tautomeric selaginellin U along with its biogenetic pathway was confirmed and proposed by a cross-validation of the semisynthesis of compound 4 from selaginellin (3) and derivation from 2 to 4. Additionally, compounds 3, 13 and 16 exhibited good inhibitory activities against ?-site amyloid precursor protein cleaving enzyme 1 (BACE1) with IC50 values of 81.17, 51.13 and 48.89?µM, respectively.

| S-EPMC5541560 | biostudies-literature

Data on the anti-tumor effects of <i>Selaginella tamariscina</i> extract and amentoflavone combined with doxorubicin in mice.

Project description:Here, we report animal experimental data associated with the article entitled "AKR1B10-inhibitory Selaginella tamariscina extract and amentoflavone decrease the growth of A549 human lung cancer cells in vitro and in vivo" (Jung et al., 2017) [1]. We tested the synergistic anti-tumor effects of Selaginella tamariscina extract and amentoflavone combined with doxorubicin hydrochloride in a nude mouse xenograft model of A549 human lung cancer cells. In our experiment, Selaginella tamariscina extract and amentoflavone were administered orally; and doxorubicin hydrochloride was injected intraperitoneally. We expect our preliminary data will be helpful to the development of the anticancer agent using Selaginella tamariscina extract or amentoflavone.

| S-EPMC5451183 | biostudies-literature

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