Three new guaianolides, 10alpha-hydroxy-3-oxoguaia-4(15),11(13)-dieno-12,6alpha-lactone (1), 10alpha-hydroxy-3-oxo-4betaH-guaia-11(13)-eno-12,6alpha-lactone (2), and 10alpha-hydroxy-3-oxoguaia-4,11(13)-dieno-12,6alpha-lactone (3), named chinensiolides A, B, and C were isolated from the whole plant of Siyekucai (Ixeris chinensis). The structures were determined by HREIMS, UV, IR, and one- and two-dimensional NMR techniques ((1)H and (13)C NMR, COSY, HMQC, HMBC, and NOE difference and NOESY experiments). Compounds 1 and 2 were indicated to be a mixture of flexible conformers by analyses of their 1D NOE and NOESY spectra as well as the temperature dependence of their (1)H and (13)C NMR spectra. Chinensiolide B (2) was transformed to chinensiolide C (3) in a three-step conversion.
Two new guaianolides, named chinensiolides D (5) and E (6), were isolated from Ixeris chinensis Nakai, and their structures were determined to be 10alpha-hydroxy-3-oxoguaia-11(13)-eno-12,6alpha-lactone (5) and 10alpha-hydroxy-3beta-O-[2,6-di(p-hydroxyphenylacetyl)-beta-glucopylanosyl]guaia-4(15),11(13)-dieno-12,6alpha-lactone (6). The first isolation of (11S)-10alpha-hydroxy-3-oxoguaia-4-eno-12,6alpha-lactone (4) from natural sources and its characterization are also reported. Chinenciolide E (6) showed significant growth inhibitory activity toward VA-13 malignant lung tumor cells (IC50 = 0.72 microM).
In this study, the second-order model, Fick’s second law of diffusion, and the Peleg model were used to evaluate the extraction kinetic model of polysaccharide (CPP) from
Codonopsis pilosula
. The characteristic functional groups, surface structure, and physical and chemical properties of CPP were analyzed by multi-spectroscopic and microscopic techniques. The results showed that the extraction process agreed well with the second-order model, Fick’s second diffusion law, and Peleg model. Rheological tests showed that CPP exhibited different viscosity changes under different conditions (Solution viscosity was inversely proportional to temperature, time, etc.; proportional to polysaccharide concentration, Na
+
content, etc.). CPP was composed of molecular aggregates composed of small particles, with more pore structure and basically completely decomposed at 130 °C. The hypoglycemic study showed that CPP had a strong inhibitory effect on α-glycosidase than α-amylase. The morphology and subsequent structural features, anti-diabetic potential, and rheological properties of CPP were revealed to provide a theoretical basis for the development of pharmaceutical preparations or health food and functional food for the treatment of diabetes.
Graphic Abstract
Supplementary Information
The online version contains supplementary material available at 10.1007/s13399-022-02518-w.
In this study, the extraction conditions of Nostoc commune Vauch polysaccharide (NCVP) were optimized by single factor and orthogonal experiments. Then, the NCVP microcapsules (NCVPM) were prepared. After analyzing the microcapsule structural and thermal characteristics, the skin wound healing ability was studied by establishing back trauma rat models. Results showed that the NCVP yield was 10.37% under the following optimum conditions: 210 min extraction time, solid–liquid ratio of 1:50 and extraction temperature of 90 °C. The overall performance of the microcapsule was the best when the concentration of sodium alginate, calcium chloride and chitosan was 2%, 3% and 0.3%, respectively. NCVPM had spherical morphology, typical microcapsule structural characteristics and good thermal stability, and NCVP was dispersed in the microcapsules. NCVPM showed good biocompatibility and biodegradability, which met the requirements for slow-release polymer materials. After 14 days of treatment, the wound healing rate was 92.4%, the cells were arranged neatly and regularly, the cell nucleus became large and elliptical, the cell had a tendency to divide, and the fibers and microvessel were significantly more. By evaluating the mechanism, NCVPM could increase the content of hydroxyproline and glutathione to protect cells from oxidative damage, leading in turn to accelerated wound healing and shorter wound healing times. It could also accelerate cell division, collagen and microvascular production by increasing transcription levels of vascular endothelial growth factor mRNA and miRNA-21.
The crude polysaccharide (CPNP) of Codonopsis pilosula was obtained by hot-water extraction technology. The extraction kinetic model established according to Fick’s first law of diffusion and related parameters of polysaccharide was studied. CPNP microcapsules were prepared by blending with sodium alginate, Ca2+ ions and crude CPNP. The quality control (Drug loading rate, embedding rate and release rate, etc) of CPNP microcapsules were analyzed by pharmacopeas standards. The structure feature of CPNP microcapsules also were determined with various methods. The wound healing ability of CPNP microcapsules loading with different concentration of CPNP was evaluated using the rat wound model. The activity of various enzymes and the expression levels of pro-inflammatory factors in the model skin tissue also were determined by enzyme linked immunosorbent assay (ELISA). Hematoxylin-eosin staining (HE), Masson, immunohistochemistry were used to investigate the external application effect of CPNP microcapsules on skin wound repair. The extraction kinetics of CPNP was established with the linear correlation coefficient (R2) of 0.83-0.93, implied that the extraction process was fitted well with the Fick’s first law of diffusion. The CPNP has good compatibility with sodium alginate and Ca2+ ions by SEM and TEM observation, and the particle size of CPNP microcapsules was 21.25±2.84 μm with the good degradation rate, loading rate (61.59%) and encapsulation rate (55.99%), maximum swelling rate (397.380 ±25.321%). Compared with control group, the redness, and swelling, bleeding, infection, and exudate of the damaged skin decreased significantly after CPNP microcapsules treatment, and the CPNP microcapsules groups exhibited good wound healing function with less inflammatory cell infiltration. The pathological structure showed that in the CPNP microcapsules group, more newborn capillaries, complete skin structure, and relatively tight and orderly arrangement of collagen fibers were observed in the skin of rats. CPNP microcapsules could effectively inhibit the high expression of pro-inflammatory factors in damaged skin, and significantly increase the contents of related enzymes (GSH-Px, T-AOC, LPO) and collagen fibers. The relative expression levels of genes (VEGF and miRNA21) in the CPNP microcapsules group were higher than those in the model group and the negative group. The above results suggested that the CPNP microcapsules could controlled-release the CPNP to the wound surface, and then played a better role in antibacterial, anti-inflammatory and skin wound repair.
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