Evaluation and enzyme-aided enhancement of anti-photoaging properties of Camellia japonica in UVA-irradiated keratinocytes.

Exposure to ultraviolet (UV) radiation is the main reason behind extrinsic skin aging. Changes due to chronic UV exposure are called photoaging. Natural products are effective ingredients against UV-mediated skin damage. Present study investigated the anti-photoaging properties of Camellia japonica flowers which possess various bioactivities. To enrich the extracts of C. japonica flowers, pectinase and beta-glucosidase treatment was employed. Anti-photoaging effect was screened using the changes in MMP-1 and collagen levels in UVA-irradiated human HaCaT keratinocytes. The crude extract of C. japonica flowers (CE) was shown to decrease the UVA-induced MMP-1 secretion while attenuating the collagen levels. Pectinase and beta-glucosidase treated CE (ECE) showed increased anti-photoaging effects against UVA-induced changes in MMP-1 and collagen production. Camellenodiol (CMD), a known triterpenoid from C. japonica, isolated as the active ingredient of ECE and its anti-photoaging effect was screened. Results showed that CMD ameliorated the UVA-induced deterioration in collagen levels by suppressing MMP-1 production in transcriptional level. CMD treatment downregulated the phosphorylation of p38, ERK, and JNK MAPKs along their downstream effectors, c-Fos, and c-Jun. In conclusion, enzyme-assisted extraction of C. japonica flowers was suggested to enhance the anti-photoaging properties suggestively through high bioactive content such as CMD.

Chemical Structure and Biological Activities of Secondary Metabolites from Salicornia europaea L.

Salicornia europaea L. is a halophyte that grows in salt marshes and muddy seashores, which is widely used both as traditional medicine and as an edible vegetable. This salt-tolerant plant is a source of diverse secondary metabolites with several therapeutic properties, including antioxidant, antidiabetic, cytotoxic, anti-inflammatory, and anti-obesity effects. Therefore, this review summarizes the chemical structure and biological activities of secondary metabolites isolated from Salicornia europaea L.

Panax ginseng-Derived Extracellular Vesicles Facilitate Anti-Senescence Effects in Human Skin Cells: An Eco-Friendly and Sustainable Way to Use Ginseng Substances.

Ginseng is a traditional herbal medicine in eastern Asian countries. Most active constituents in ginseng are prepared via fermentation or organic acid pretreatment. Extracellular vesicles (EVs) are released by most organisms from prokaryotes to eukaryotes and play central roles in intra- and inter-species communications. Plants produce EVs upon exposure to microbes; however, their direct functions and utility for human health are barely known, except for being proposed as delivery vehicles. In this study, we isolated EVs from ginseng roots (GrEVs) or the culture supernatants of ginseng cells (GcEVs) derived from Panax ginseng C.A. Meyer and investigated their biological effects on human skin cells. GrEV or GcEV treatments improved the replicative senescent or senescence-associated pigmented phenotypes of human dermal fibroblasts or ultraviolet B radiation-treated human melanocytes, respectively, by downregulating senescence-associated molecules and/or melanogenesis-related proteins. Based on comprehensive lipidomic analysis using liquid chromatography mass spectrometry, the lipidomic profile of GrEVs differed from that of the parental root extracts, showing significant increases in 70 of 188 identified lipid species and prominent increases in diacylglycerols, some phospholipids (phosphatidylcholine, phosphatidylethanolamine, lysophosphatidylcholine), and sphingomyelin, revealing their unique vesicular properties. Therefore, our results imply that GEVs represent a novel type of bioactive and sustainable nanomaterials that can be applied to human tissues for improving tissue conditions and targeted delivery of active constituents.

Camellioside A, isolated from Camellia japonica flowers, attenuates UVA-induced production of MMP-1 in HaCaT keratinocytes via suppression of MAPK activation.

Ultraviolet (UV) radiation is responsible for various damages to the skin, collectively referred to as photoaging. A key UV-induced effect on the skin is excessive degradation of collagen and related structural abnormalities. Camellia japonica is a flowering plant with cosmeceutical properties. In the present study, Camellioside A (CMDA), a triterpene saponin, was investigated for its effects against UVA-induced photoaging in HaCaT keratinocytes. CMDA was analyzed to determine its attenuating effects against UVA-induced overproduction of the collagen degradation enzyme, matrix metalloproteinase-1 (MMP-1), in UVA-irradiated immortalized human HaCaT keratinocytes. UVA irradiation significantly increased MMP-1 release from keratinocytes in addition to suppressing type Iα1 pro-collagen production. Treatment with CMDA reversed the effects of UVA irradiation on the production of MMP-1 and type Iα1 pro-collagen. UVA irradiation also stimulated the activation of p38, ERK and JNK mitogen-activated protein kinases (MAPKs) and their downstream transcription factor activator protein 1 (a heterodimer of c-Fos and c-Jun). MAPK activation and consequent phosphorylation of c-Fos and c-Jun were also inhibited by CMDA treatment. In conclusion, the present study indicated that CMDA may have potential antiphotoaging properties due to suppression of UVA-mediated MMP-1 production.

Comparative Lipidomic Analysis of Extracellular Vesicles Derived from Lactobacillus plantarum APsulloc 331261 Living in Green Tea Leaves Using Liquid Chromatography-Mass Spectrometry.

Lactobacillus plantarum is a popular probiotic species due to its safe and beneficial effects on humans; therefore, novel L. plantarum strains have been isolated and identified from various dietary products. Given that bacteria-derived extracellular vesicles (EVs) have been considered as efficient carriers of bioactive materials and shown to evoke cellular responses effectively, L. plantarum-derived EVs are expected to efficiently elicit health benefits. Herein, we identified L. plantarum APsulloc 331261 living in green tea leaves and isolated EVs from the culture medium. We performed quantitative lipidomic analysis of L. plantarum APsulloc 331261 derived EVs (LEVs) using liquid chromatography-mass spectrometry. In comparison to L. plantarum APsulloc 331261, in LEVs, 67 of 320 identified lipid species were significantly increased and 19 species were decreased. In particular, lysophosphatidylserine(18:4) and phosphatidylcholine(32:2) were critically increased, showing over 21-fold enrichment in LEVs. In addition, there was a notable difference between LEVs and the parent cells in the composition of phospholipids. Our results suggest that the lipidomic profile of bacteria-derived EVs is different from that of the parent cells in phospholipid content and composition. Given that lipids are important components of EVs, quantitative and comparative analyses of EV lipids may improve our understanding of vesicle biogenesis and lipid-mediated intercellular communication within or between living organisms.

Separation of nine novel triterpene saponins from Camellia japonica seeds using high-performance countercurrent chromatography and reversed-phase high-performance liquid chromatography.

INTRODUCTION: Camellia japonica L. (Theaceae) is an evergreen shrub, which is cultivated as a popular ornamental tree in Korea, China, and Japan and its seeds have been used as a source of cooking oil, in cosmetics and as a traditional medicine. Intensive phytochemical works have revealed that oleanane-type saponins are the characteristic compounds of the seeds of C. japonica. OBJECTIVE: The purpose of the present study is to isolate and determine oleanane-type saponins from C. japonica using high-performance countercurrent chromatography (HPCCC) coupled with reversed-phase high-performance liquid chromatography (RP-HPLC) and spectroscopic evidences, respectively. METHODOLOGY: HPLC electrospray ionisation quadrupole time-of-flight mass spectrometry (ESI-Q-TOF-MS) was applied to profile the saponin composition of an enriched saponin extract of C. japonica seeds. The enriched saponin extract was separated by HPCCC using a dichloromethane/methanol/isopropanol/water (9:6:1:4, v/v/v/v) system and RP-HPLC. The structures of the isolates were determined utilising ESI-Q-TOF-MS, one-dimensional and two-dimensional NMR and optical rotation. RESULTS: HPCCC on enriched saponin extract of C. japonica yielded four saponin fractions in the order of the number of sugars attached to the triterpene aglycone, and preparative RP-HPLC on each saponin fraction led to the isolation of nine novel saponins, namely camoreoside A-I, along with six known ones. CONCLUSIONS: This study indicates that combination of HPLC-ESI-Q-TOF-MS analysis and HPCCC coupled with RP-HPLC are excellent tools for discovering saponins from natural sources.

Scalalactams A⁻D, Scalarane Sesterterpenes with a γ-Lactam Moiety from a Korean Spongia Sp. Marine Sponge.

Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams A⁻D (1⁻4). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams A⁻D (1⁻4) possess a scalarane carbon skeleton with a rare structural feature of a γ-lactam moiety within the molecules. Scalalactams A and B (1 and 2) have an extended isopropanyl chain at the lactam ring, and scalalactams C and D (3 and 4) possess a phenethyl group at the lactam ring moiety. Scalalactams A⁻D (1⁻4) did not show FXR antagonistic activity nor cytotoxicity up to 100 µM.

Identification of Major Flavone C-Glycosides and Their Optimized Extraction from Cymbidium kanran Using Deep Eutectic Solvents.

Cymbidium kanran, an orchid exclusively distributed in Northeast Asia, has been highly valued as a decorative plant and traditional herbal medicine. Here, C. kanran extracts were prepared in 70% aqueous methanol using ultrasound-assisted extraction (UAE) and subjected to liquid chromatography-photodiode array detection and ultra-high performance liquid chromatography-quadrupole-time-of-flight-mass spectrometry analysis, which were used for quantitative and qualitative analysis, respectively. It was found that the extracts were rich in flavone C-glycosides including vicenin-2, vicenin-3, schaftoside, vitexin, and isovitexin. Ten deep eutectic solvents (DESs) were synthesized by combining choline chloride (hydrogen bond acceptor) with various polyols and diols (hydrogen bond donors) and were tested as a medium for the efficient production of extracts enriched with potentially bioactive flavone C-glycosides from C. kanran. A DES named ChCl:DPG, composed of choline chloride and dipropylene glycol at a 1:4 molar ratio, exhibited the best extraction yields. Then, the effects of extraction conditions on the extraction efficiency were investigated by response surface methodology. Lower water content in the extraction solvent and longer extraction time during UAE were desirable for higher extraction yields. Under the statistically optimized conditions, in which 100 mg of C. kanran powder were extracted in 0.53 mL of a mixture of ChCl:DPG and water (74:26, w/w) for 86 min, a total of 3.441 mg g-1 flavone C-glycosides including 1.933 mg g-1 vicenin-2 was obtained. This total yield was 196%, 131%, and 71% more than those obtained using 100% methanol, water, and 70% methanol, respectively.

Flavokawains B and C, melanogenesis inhibitors, isolated from the root of Piper methysticum and synthesis of analogs.

The ethanolic extract of the root of Piper methysticum was found to inhibit melanogenesis in MSH-activated B16 melanoma cells. Flavokawains B and C were isolated from this extract based on their anti-melanogenesis activity and found to inhibit melanogenesis with IC50 values of 7.7µM and 6.9µM, respectively. Flavokawain analogs were synthesized through a Claisen-Schmidt condensation of their corresponding acetophenones and benzaldehydes and were evaluated in terms of their tyrosinase inhibitory and anti-melanogenesis activities. Compound 1b was the most potent of these with an IC50 value of 2.3µM in melanogenesis inhibition assays using MSH-activated B16 melanoma cells.

Application of high-performance countercurrent chromatography for the isolation of steroidal saponins from Liriope plathyphylla.

High-performance countercurrent chromatography (HPCCC) with electrospray light-scattering detection was applied for the first time to isolate a spirostanol and a novel furostanol saponin from Liriope platyphylla. Due to the large differences in KD values between the two compounds, a two-step HPCCC method was applied in this study. The primary HPCCC employed methylene chloride/methanol/isopropanol/water (9:6:1:4 v/v, 4 mL/min, normal-phase mode) conditions to yield a spirostanol saponin (1). After the primary HPCCC run, the solute retained in the stationary phase (SP extract) in HPCCC column was recovered and subjected to the second HPCCC on the n-hexane/n-butanol/water system (1:9:10 v/v, 5 mL/min, reversed-phase mode) to yield a novel furostanol saponin (2). The isolated spirostanol saponin was determined to be 25(S)-ruscogenin 1-O-ß-D-glucopyranosyl (1→2)-[ß-D-xylopyranosyl (1→3)]-ß-D-fucopyranoside (spicatoside A), and the novel furostanol saponin was elucidated to be 26-O-ß-D-glucopyranosyl-25(S)-furost-5(6)-ene-1ß-3ß-22α-26-tetraol-1-O-ß-D-glucopyranosyl (1→2)-[ß-D-xylopyranosyl-(1→3)]-ß-D-fucopyranoside (spicatoside D).

21-O-angeloyltheasapogenol E3, a novel triterpenoid saponin from the seeds of tea plants, inhibits macrophage-mediated inflammatory responses in a NF-κB-dependent manner.

21-O-Angeloyltheasapogenol E3 (ATS-E3) is a triterpenoid saponin recently isolated from the seeds of the tea tree Camellia sinensis (L.) O. Kuntze. ATS-E3 has several beneficial properties including anti-inflammatory, antidiabetic, antiatherosclerotic, and anticancer effects. Unlike other phenolic compounds isolated from tea plants, there are no studies reporting the pharmacological action of ATS-E3. In this study, we therefore aimed to explore the cellular and molecular inhibitory activities of ATS-E3 in macrophage-mediated inflammatory responses. ATS-E3 remarkably diminished cellular responses of macrophages such as FITC-dextran-induced phagocytic uptake, sodium nitroprusside- (SNP-) induced radical generation, and LPS-induced nitric oxide (NO) production. Analysis of its molecular activity showed that this compound significantly suppressed the expression of inducible NO synthase (iNOS), nuclear translocation of nuclear factor- (NF-) κB subunits (p50 and p65), phosphorylation of inhibitor of κB kinase (IKK), and the enzyme activity of AKT1. Taken together, the novel triterpenoid saponin compound ATS-E3 contributes to the beneficial effects of tea plants by exerting anti-inflammatory and antioxidative activities in an AKT/IKK/NF-κB-dependent manner.

Selective peroxisome proliferator-activated receptor δ isosteric selenium agonists as potent anti-atherogenic agents in vivo.

We report the synthesis and in vivo activity of a novel anti-atherogenic agent, isosteric selenium PPARδ-selective ligand. This ligand did not cause significant body or liver weight changes and did not have obvious adverse effects on intestinal polyp formation. Our overall results clearly demonstrate that PPARδ is a viable drug candidate for targeting and treating atherosclerosis.