RESUMEN
Although melanin protects against ultraviolet radiation, its overproduction causes freckles and senile lentigines. Recently, various biological effects of metabolites derived from marine microorganisms have been highlighted due to their potential for biological and pharmacological applications. In this study, we discovered the anti-melanogenic effect of Bacillus sp. APmarine135 and verified the skin-whitening effect. Fractions of APmarine135 showed the melanin synthesis inhibition effect in B16 melanoma cells, and 2,4,6-triphenyl-1-hexene was identified as an active compound. The melanogenic capacity of 2,4,6-triphenyl-1-hexene (1) was investigated by assessing the intracellular melanin content in B16 cells. Treatment with 5 ppm of 2,4,6-triphenyl-1-hexene (1) for 72 h suppressed the α-melanocyte-stimulating hormone (α-MSH)-induced intracellular melanin increase to the same level as in the untreated control group. Additionally, 2,4,6-triphenyl-1-hexene (1) treatment suppressed the activity of tyrosinase, the rate-limiting enzyme for melanogenesis. Moreover, 2,4,6-triphenyl-1-hexene (1) treatment downregulated tyrosinase, Tyrp-1, and Tyrp-2 expression by inhibiting the microphthalmia-associated transcription factor (MITF). Furthermore, 2,4,6-triphenyl-1-hexene (1) treatment decreased the melanin content in the three-dimensional (3D) human-pigmented epidermis model MelanoDerm and exerted skin-whitening effects. Mechanistically, 2,4,6-triphenyl-1-hexene (1) exerted anti-melanogenic effects by suppressing tyrosinase, Tyrp-1, and Tyrp-2 expression and activities via inhibition of the MITF. Collectively, these findings suggest that 2,4,6-triphenyl-1-hexene (1) is a promising anti-melanogenic agent in the cosmetic industry.
Asunto(s)
Alquenos , Bacillus , Melaninas , Compuestos de Terfenilo , Humanos , Monofenol Monooxigenasa/metabolismo , Bacillus/metabolismo , Rayos Ultravioleta/efectos adversos , Línea Celular Tumoral , Factor de Transcripción Asociado a Microftalmía/metabolismo , alfa-MSH/farmacologíaRESUMEN
An ubiquinone derivative, pseudoalteromone A (1), has been isolated from two marine-derived Pseudoalteromonas spp., APmarine002 and ROA-050, and its anti-melanogenesis activity was investigated. The anti-melanogenic capacity of pseudoalteromone A was demonstrated by assessing the intracellular and extracellular melanin content and cellular tyrosinase activity in the B16 cell line, Melan-a mouse melanocyte cell line, and MNT-1 human malignant melanoma cell line. Treatment with pseudoalteromone A (40 µg/mL) for 72 h reduced α-melanocyte-stimulating hormone (α-MSH)-induced intracellular melanin production by up to 44.68% in B16 cells and 38.24% in MNT-1 cells. Notably, pseudoalteromone A induced a concentration-dependent reduction in cellular tyrosinase activity in B16 cell, and Western blot analyses showed that this inhibitory activity was associated with a significant decrease in protein levels of tyrosinase and tyrosinase-related protein 1 (Tyrp-1), suggesting that pseudoalteromone A exerts its anti-melanogenesis activity through effects on melanogenic genes. We further evaluated the skin-whitening effect of pseudoalteromone A in the three-dimensional (3D) pigmented-epidermis model, MelanoDerm, and visualized the 3D distribution of melanin by two-photon excited fluorescence imaging in this human skin equivalent. Collectively, our findings suggest that pseudoalteromone A inhibits tyrosinase activity and expression and that this accounts for its anti-melanogenic effects in melanocytes.
Asunto(s)
Antineoplásicos , Melanocitos , Pseudoalteromonas , Ubiquinona , Animales , Humanos , Antineoplásicos/química , Antineoplásicos/farmacología , Organismos Acuáticos , Línea Celular Tumoral/efectos de los fármacos , Melanocitos/efectos de los fármacos , Monofenol Monooxigenasa/metabolismo , Ubiquinona/química , Ubiquinona/farmacologíaRESUMEN
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.
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Chenopodiaceae/química , Animales , Humanos , Fitoquímicos/química , Plantas Tolerantes a la Sal/químicaRESUMEN
Many bioactive materials have been isolated from marine microorganisms, including alkaloids, peptides, lipids, mycosporine-like amino acids, glycosides, and isoprenoids. Some of these compounds have great potential in the cosmetic industry due to their photo-protective, anti-aging, and anti-oxidant activities. In this study, sarmentosamide (1) was isolated from marine-derived Streptomyces sp. APmarine042, after which its capacity to decrease skin aging was examined in-vitro. Sarmentosamide (1) was found to significantly reduce UVB-induced matrix metalloproteinase-1 (MMP-1) expression in normal human dermal fibroblasts (NHDFs) by inhibiting the extracellular signal-regulated kinase (ERK) and the c-Jun N-terminal kinase (JNK) phosphorylation, which are regulatory pathways upstream of MMP-1 transcription. Additionally, we confirmed that sarmentosamide (1) decreased tumor necrosis factor-alpha (TNF-α), induced MMP-1 secretion in NHDFs, and exhibited free-radical scavenging activity, as demonstrated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Therefore, our study suggests that sarmentosamide (1) could be a promising anti-aging agent that acts via the downregulation of MMP-1 expression.
Asunto(s)
Fibroblastos/efectos de los fármacos , Metaloproteinasa 1 de la Matriz/metabolismo , Inhibidores de la Metaloproteinasa de la Matriz/farmacología , Envejecimiento de la Piel/efectos de los fármacos , Piel/efectos de los fármacos , Streptomyces/metabolismo , Línea Celular , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Fibroblastos/metabolismo , Fibroblastos/patología , Fibroblastos/efectos de la radiación , Depuradores de Radicales Libres/química , Depuradores de Radicales Libres/aislamiento & purificación , Depuradores de Radicales Libres/farmacología , Sedimentos Geológicos/microbiología , Proteínas Quinasas JNK Activadas por Mitógenos/metabolismo , Metaloproteinasa 1 de la Matriz/genética , Inhibidores de la Metaloproteinasa de la Matriz/química , Inhibidores de la Metaloproteinasa de la Matriz/aislamiento & purificación , Estructura Molecular , Fosforilación , Piel/metabolismo , Piel/patología , Piel/efectos de la radiación , Envejecimiento de la Piel/efectos de la radiación , Factor de Necrosis Tumoral alfa/metabolismoRESUMEN
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.
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Vesículas Extracelulares/metabolismo , Lactobacillus plantarum/metabolismo , Lipidómica/métodos , Lípidos/análisis , Hojas de la Planta/microbiología , Probióticos/análisis , Té/microbiología , Cromatografía Liquida/métodos , Espectrometría de Masas en Tándem/métodosRESUMEN
Ultraviolet (UV) irradiation induces detrimental changes in human skin which result in photoaging. UV-induced intracellular changes cause degradation of extracellular matrix (ECM). UV-stimulated cleavage of collagen in ECM occurs via matrix metalloproteinases (MMPs). (±)-syringaresinol (SYR), a phytochemical which belongs to the lignan group of polyphenols, was investigated for its ability to reverse the UVA-induced changes in human HaCaT keratinocytes and dermal fibroblasts (HDFs) in vitro. Effect of SYR on UVA-induced changes was investigated by production and activation of MMPs and its transcriptional upstream effectors; mitogen-activated protein kinases (MAPKs) and pro-inflammatory mediators. Levels of expression were determined using ELISA, RT-PCR and immunoblotting. UVA irradiation stimulated the production of MMP-1 and inhibited collagen production. SYR treatment suppressed MMP-1 and enhanced collagen production in UVA-irradiated HaCaT keratinocytes and HDFs. SYR repressed the UV-induced phosphorylation of p38, ERK and JNK MAPKs in HaCaT keratinocytes while only suppressing JNK phosphorylation in HDFs. In addition, SYR was able to inhibit UVA-induced production of inflammatory cytokines; TNF-α, COX-2, IL-1ß and IL-6. Moreover, SYR suppressed the activator protein-1 (AP-1), a heterodimer of phosphorylated transcription factors c-Jun and c-Fos. SYR-treatment decreased nuclear levels of activated c-Fos and c-Jun as a mechanism to inhibit UVA-induced transcriptional activities leading to MMP-1 production. In conclusion, current results demonstrated that SYR could inhibit UVA-induced upregulation of MMP-1 by suppressing MAPK/AP-1 signaling in HaCaT keratinocytes and HDFs. Therefore, SYR was suggested as a potential compound with antiphotoaging properties against UVA-induced skin aging.
Asunto(s)
Fibroblastos/efectos de los fármacos , Furanos/farmacología , Queratinocitos/efectos de los fármacos , Lignanos/farmacología , Sistema de Señalización de MAP Quinasas , Metaloproteinasa 1 de la Matriz/metabolismo , Factor de Transcripción AP-1/metabolismo , Rayos Ultravioleta , Colágeno/metabolismo , Ensayo de Inmunoadsorción Enzimática , Fibroblastos/efectos de la radiación , Células HaCaT , Humanos , Inflamación , Queratinocitos/efectos de la radiación , Lignanos/metabolismo , Fosforilación , Piel/efectos de los fármacos , Piel/efectos de la radiación , Envejecimiento de la Piel , Proteínas Quinasas p38 Activadas por Mitógenos/metabolismoRESUMEN
A cytotoxic alkaloidal meroterpenoid, saccharoquinoline (1), has been isolated from the fermentation broth of the marine-derived bacterium Saccharomonospora sp. CNQ-490. The planar structure of 1 was elucidated by 1D, 2D NMR, and MS spectroscopic data analyzes, while the relative configuration of 1 was defined through the interpretation of NOE spectroscopic data. Saccharoquinoline (1) is composed of a drimane-type sesquiterpene unit in combination with an apparent 6,7,8-trihydroxyquinoline-2-carboxylic acid. This combination of biosynthetic pathways was observed for the first time in natural microbial products. Saccharoquinoline (1) was found to have cytotoxicity against the HCT-116 cancer cell line by inducing G1 arrest, which leads to cell growth inhibition.
Asunto(s)
Actinobacteria/metabolismo , Antineoplásicos/farmacología , Terpenos/química , Terpenos/farmacología , Actinobacteria/química , Antineoplásicos/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Humanos , Modelos Moleculares , Estructura MolecularRESUMEN
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.
Asunto(s)
Camellia/embriología , Cromatografía Líquida de Alta Presión/métodos , Cromatografía de Fase Inversa/métodos , Distribución en Contracorriente/métodos , Saponinas/aislamiento & purificación , Semillas/química , Triterpenos/aislamiento & purificación , Estructura Molecular , Extractos Vegetales/química , Espectroscopía de Protones por Resonancia Magnética , Saponinas/química , Espectrometría de Masa por Ionización de Electrospray , Triterpenos/químicaRESUMEN
Antartin (1), a new zizaane-type sesquiterpene, was isolated from Streptomyces sp. SCO736. The chemical structure of 1 was assigned from the interpretation of 1D and 2D NMR in addition to mass spectrometric data. The relative stereochemistry of 1 was determined by analysis of NOE data, while the absolute stereochemistry was decided based on a comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Antartin (1) showed cytotoxicity against A549, H1299, and U87 cancer cell lines by causing cell cycle arrest at the G1 phase.
Asunto(s)
Citotoxinas/química , Sesquiterpenos/química , Streptomyces/química , Células A549 , Regiones Antárticas , Línea Celular Tumoral , Dicroismo Circular , Citotoxinas/farmacología , Fase G1/efectos de los fármacos , Sedimentos Geológicos/microbiología , Humanos , Espectroscopía de Resonancia Magnética/métodos , Sesquiterpenos/farmacologíaRESUMEN
Intensive study on the chemical components of a Korean marine sponge, Spongia sp., has led to the isolation of four new scalarane sesterterpenes, scalalactams Aâ»D (1â»4). Their chemical structures were elucidated from the analysis of spectroscopic data including 1D-and 2D-NMR as well as MS data. Scalalactams Aâ»D (1â»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 Aâ»D (1â»4) did not show FXR antagonistic activity nor cytotoxicity up to 100 µM.
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Poríferos/química , Sesterterpenos/química , Sesterterpenos/farmacología , Animales , Organismos Acuáticos/química , Evaluación Preclínica de Medicamentos/métodos , Humanos , Lactamas/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Receptores Citoplasmáticos y Nucleares/antagonistas & inhibidoresRESUMEN
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.
Asunto(s)
Flavonas/química , Monosacáridos/química , Orchidaceae/química , Extractos Vegetales/química , Solventes/química , Apigenina/química , Glucósidos/química , GlicósidosRESUMEN
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.
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Flavonoides/química , Flavonoides/farmacología , Kava/química , Melaninas/antagonistas & inhibidores , Animales , Flavonoides/síntesis química , Humanos , Melaninas/biosíntesis , Melaninas/síntesis química , Melanoma Experimental/tratamiento farmacológico , Ratones , Relación Estructura-ActividadRESUMEN
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 (1â2)-[ß-D-xylopyranosyl (1â3)]-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 (1â2)-[ß-D-xylopyranosyl-(1â3)]-ß-D-fucopyranoside (spicatoside D).
Asunto(s)
Distribución en Contracorriente/métodos , Liriope (Planta)/química , Extractos Vegetales/aislamiento & purificación , Saponinas/aislamiento & purificación , Esteroides/aislamiento & purificación , Extractos Vegetales/análisis , Saponinas/análisis , Esteroides/análisisRESUMEN
In this study, we aimed to examine the cellular and molecular mechanisms of lancemaside A from Codonopsis lanceolata (Campanulaceae) in the inflammatory responses of monocytes (U937 cells) and macrophages (RAW264.7 cells). Lancemaside A significantly suppressed the inflammatory functions of lipopolysaccharide- (LPS-) treated RAW264.7 cells by suppressing the production of nitric oxide (NO), the expression of the NO-producing enzyme inducible NO synthase (iNOS), the upregulation of the costimulatory molecule CD80, and the morphological changes induced by LPS exposure. In addition, lancemaside A diminished the phagocytic activity of RAW264.7 cells and boosted the neutralizing capacity of these cells when treated with the radical generator sodium nitroprusside (SNP). Interestingly, lancemaside A strongly blocked the adhesion activity of RAW264.7 cells to plastic culture plates, inhibited the cell-cell and cell-fibronectin (FN) adhesion of U937 cells that was triggered by treatment with an anti-ß1-integrin (CD29) antibody and immobilized FN, respectively. By evaluating the activation of various intracellular signaling pathways and the levels of related nuclear transcription factors, lancemaside A was found to block the activation of inhibitor of κB kinase (IKK) and p65/nuclear factor- (NF-) κB. Taken together, our findings strongly suggest that the anti-inflammatory function of lancemaside A is the result of its strong antioxidative and IKK/NF-κB inhibitory activities.
Asunto(s)
Codonopsis/química , Macrófagos/efectos de los fármacos , Monocitos/efectos de los fármacos , Saponinas/química , Animales , Antioxidantes/química , Adhesión Celular , Línea Celular , Supervivencia Celular , Humanos , Quinasa I-kappa B/metabolismo , Inflamación , Integrina beta1/metabolismo , Lipopolisacáridos , Macrófagos/citología , Ratones , Monocitos/citología , Óxido Nítrico/metabolismo , Nitroprusiato/química , Fagocitosis , Células U937RESUMEN
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.
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Antiinflamatorios/farmacología , Macrófagos/efectos de los fármacos , Saponinas/farmacología , Triterpenos/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Camellia sinensis , Línea Celular , Células HEK293 , Humanos , Inflamación/inmunología , Inflamación/metabolismo , Inflamación/prevención & control , Macrófagos/inmunología , Macrófagos/metabolismo , Ratones , FN-kappa B/metabolismo , Óxido Nítrico/biosíntesis , Saponinas/aislamiento & purificación , Semillas , Transducción de Señal/efectos de los fármacos , Triterpenos/aislamiento & purificaciónRESUMEN
Jasmonic acid (JA) plays pivotal roles in diverse plant biological processes, including wound response. Chloroplast lipid hydrolysis is a critical step for JA biosynthesis, but the mechanism of this process remains elusive. We report here that DONGLE (DGL), a homolog of DEFECTIVE IN ANTHER DEHISCENCE1 (DAD1), encodes a chloroplast-targeted lipase with strong galactolipase and weak phospholipase A(1) activity. DGL is expressed in the leaves and has a specific role in maintaining basal JA content under normal conditions, and this expression regulates vegetative growth and is required for a rapid JA burst after wounding. During wounding, DGL and DAD1 have partially redundant functions for JA production, but they show different induction kinetics, indicating temporally separated roles: DGL plays a role in the early phase of JA production, and DAD1 plays a role in the late phase of JA production. Whereas DGL and DAD1 are necessary and sufficient for JA production, phospholipase D appears to modulate wound response by stimulating DGL and DAD1 expression.
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Arabidopsis/genética , Hidrolasas de Éster Carboxílico/genética , Ciclopentanos/metabolismo , Genes de Plantas , Variación Genética , Oxilipinas/metabolismo , Arabidopsis/enzimología , Arabidopsis/crecimiento & desarrollo , Arabidopsis/ultraestructura , Proteínas de Arabidopsis/genética , Proteínas de Arabidopsis/metabolismo , Cloroplastos/metabolismo , Regulación de la Expresión Génica de las Plantas , Especificidad de Órganos , Fenotipo , Fosfolipasa D/metabolismo , Fosfolipasas A/metabolismo , Fosfolipasas A1/metabolismo , Hojas de la Planta/crecimiento & desarrollo , Hojas de la Planta/metabolismo , Tallos de la Planta/crecimiento & desarrollo , Tallos de la Planta/metabolismo , Plantones/ultraestructura , Activación Transcripcional/genéticaRESUMEN
A five-step transformation of D-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of L-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, "two-headed" sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.
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Productos Biológicos/química , Glucosamina/química , Glicoesfingolípidos/síntesis química , Rhizoctonia/química , Esfingosina/análogos & derivados , Glicoesfingolípidos/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Esfingosina/síntesis química , Esfingosina/químicaRESUMEN
A rapid and efficient high-performance counter-current chromatography (HPCCC) method was developed to separate five oligostilbenes from the roots of Vitis amurensis. An n-hexane/ethyl acetate/methanol/water system (4:8:4:10, v/v/v/v) was selected as an optimal two-phase solvent system of which the upper phase was used as the stationary phase and the lower phase was used as the mobile one. Partition coefficient values for the target compounds under these optimized conditions were 0.28 (1, ampleosin A), 7.12 (2, (+)-g-viniferin), 2.26 (3, vitisin A), 5.38 (4, wilsonol C), and 11.23 (5, vitisin B). Flow-rate gradient HPCCC (4 mL/min in 0-70 min, 8 mL/min in 70-250 min) was applied to isolate the target compounds in as high purity as possible within the shortest possible run time. Under these conditions, ampelopsin A (12.1 mg), (+)-g-viniferin (10.4 mg), vitisin A (2.8 mg), wilsonol C (3.2 mg), and vitisin B (37 mg) were isolated with >95% purity from 150 mg of enriched oligostilbene extract. Although the KD of the last eluted compound, vitisin B (KD = 11.23), was relatively large, it was eluted in 115-145 min using the two-phase solvent system. This study shows that HPCCC is an efficient tool for the isolation and purification of natural products.
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Estilbenos/aislamiento & purificación , Vitis/química , Cromatografía Líquida de Alta Presión , Distribución en Contracorriente , Conformación Molecular , Estilbenos/químicaRESUMEN
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.
Asunto(s)
Camellia , Queratinocitos , Extractos Vegetales , Envejecimiento de la Piel , Camellia/química , Colágeno , Flores/química , Humanos , Queratinocitos/efectos de los fármacos , Queratinocitos/efectos de la radiación , Metaloproteinasa 1 de la Matriz/química , Extractos Vegetales/farmacología , Poligalacturonasa/química , Piel/efectos de la radiación , Envejecimiento de la Piel/efectos de los fármacos , Rayos Ultravioleta/efectos adversosRESUMEN
Skin aging is a major risk factor for the dermal diseases, and interventions to attenuate cellular senescence are expected to reduce the risk for age-related diseases involving skin atrophy. However, blocking cell death or extending proliferation causally results in side effects and an increased cancer risk. For identification of a safer approach, we focused on PDK1 inhibition, which could revert cellular senescence and reduce senescence factors in skin in vitro, in a human skin equivalent model and in an exploratory, placebo-controlled, interventional trial. Natural phytochemical kaempferol tetrasaccharides resulted in a significant reduction in cellular senescence, and an increase in collagen fiber was observed in the skin cell and human skin equivalent. Clinical enhancement in skin appearance was noted in multiple participants, and an immunohistochemical study revealed improvement in the histological appearance of skin tissue and extracellular matrix. This change was associated with relative improvement in histological markers of senescence and clinical appearance of the aged skin and an increase in collagen fiber, an essential factor for preventing skin atrophy and consistency of the basement membrane. These results indicate that PDK1 inhibition is a potentially effective antiaging intervention, suggesting a diagnostic role and preventive actions of PDK1 in senescence-associated skin atrophy.