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1.
J Chromatogr A ; 1730: 465105, 2024 Aug 16.
Artículo en Inglés | MEDLINE | ID: mdl-38908999

RESUMEN

Pseudobulbus Cremastrae seu Pleiones (PCsP), a traditional Chinese medicine known as ‶Shan-Ci-Gu″, possesses properties for clearing heat, counteracting toxicity, dissipating phlegm, and resolving masses. As a TCM with multiple bases, the dried pseudobulbs of Pleione bulbocodioides (PB), Pleione yunnanensis (PY) and Cremastra appendiculata (CA) are considered to be the official sources of PCsP. Additionally, several unofficial substitutes are also available in the market. To enhance the quality control of PCsP, an integrated strategy based on Q-marker was proposed. Initially, a study of integrating plant metabolomics, target isolation, structure identification, and activity testing afforded five Q-markers, including three new compounds. Furthermore, a quality evaluation method using a single standard to determine multi-components (SSDMC) based on Q-marker was established, which could effectively distinguish PB from CA and the counterfeit herbs. Finally, the transitivity of Q-markers was explored through a representative Chinese compound prescription containing PCsP. The results indicated that the identified Q-markers together with the established analysis methods could be effectively applied for quality control of PCsP and its preparations.


Asunto(s)
Medicamentos Herbarios Chinos , Control de Calidad , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/análisis , Medicamentos Herbarios Chinos/normas , Cromatografía Líquida de Alta Presión/métodos , Metabolómica/métodos , Medicina Tradicional China/normas , Cupressaceae/química
2.
J AOAC Int ; 106(5): 1295-1304, 2023 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-37243686

RESUMEN

BACKGROUND: Platycladus orientalis leaves (POL), as the source of the traditional Chinese medicine (TCM) Platycladi Cacumen, has frequently been found to be misused with five adulterants including Chamaecyparis obtusa leaves (COL), Cupressus funebris leaves (CFL), Juniperus virginiana leaves (JVL), Sabina chinensis leaves (SCL), and Juniperus formosana leaves (JFL). OBJECTIVE: The purpose of this study was to distinguish POL (fresh leaves) from its five adulterants (fresh leaves). METHODS: The micromorphological features in terms of transection and microscopic characteristics of POL and adulterants were captured and compared using the an microscope. Both HPLC and TLC methods for the simultaneous determination of six bioactive flavonoids (myricitrin, isoquercitrin, quercitrin, amentoflavone, afzelin, and hinokiflavone) have been developed. RESULTS: There were significant differences in microscopic features of transverse section and powders. The TLC results suggested that the spots of myricitrin in POL were more obvious than those in the five adulterants. The contents of myricitrin and quercitrin, or the total content of flavonoids in POL, determined by HPLC, were significantly higher than those in the adulterants. CONCLUSION: POL was successfully distinguished from its five adulterants by the comparison of morphology, microscopic characteristics, and chemical profiles. HIGHLIGHTS: This research provides a comprehensive morphology, microscopic identification, TLC, and HPLC analysis for authenticating POL and its five adulterants.


Asunto(s)
Cupressaceae , Medicamentos Herbarios Chinos , Cromatografía Líquida de Alta Presión/métodos , Flavonoides/análisis , Cupressaceae/química , Medicamentos Herbarios Chinos/análisis , Medicina Tradicional China
3.
Chem Biodivers ; 20(2): e202201067, 2023 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-36598403

RESUMEN

Taiwania cryptomerioides Hayata is an endangered relict plant belonging to Taxodiaceae, and it is also an endemic plant to China. The decay-resistant of Taiwania timber can provide highly quality wood for building and furniture. Plenty of regenerative of leaves of T. cryptomerioides also has been used as a resource for the discovery of new dimeric diterpenoids. In a search for structurally diverse dimeric diterpenoids and potent bioactive isolates, ten new heterodimeric diterpenoids, taiwaniadducts K-T (1-4, 6, 8-11, and 14), along with five known ones (5, 7, 12, 13, and 15), were isolated from the leaves of T. cryptomerioides. These new compounds were defined by comprehensive spectroscopic analyses, putative biosynthetic pathways, and the values of optical. Biologically, anti-multidrug resistance (MDR) activities of compounds were evaluated. Compounds 4 and 10 exerted a 9.18-fold potentiation effect on bortezmib (BTZ) susceptibility at a tested concentration (20 µM) better than the positive control verapamil. The research of the leaves of T. cryptomerioides not only added the new data to the structural diversity and activities of dimeric diterpenoids but also could provide support for the medical and industrial application of the leaves of this endangered relict plant.


Asunto(s)
Cupressaceae , Diterpenos , Diterpenos/química , Extractos Vegetales/química , Madera , Análisis Espectral , Cupressaceae/química , Estructura Molecular
4.
Phytochemistry ; 206: 113520, 2023 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-36544302

RESUMEN

Forest operations and wood industry generate large amounts of residues that are discarded in the field and cause environmental pollution. However, these biomass residues are still raw materials to obtain value-added products, such as essential oils, organic/aqueous extracts and resins that are among the great natural sources of bioactive metabolites. Thus, in recent years, the scientific community is giving special attention to their valorization. To date, different uses of biomass residues have been proposed, such as a source of renewable energy, fertilizers, animal feed and bioactive molecules. In this context, Cryptomeria japonica biomass residues (e.g., bark and its exudate, heartwood, sapwood, leaves, cones and roots) represent a source of diverse specialized metabolites (e.g., sesqui-, di-, tri- and sesquarterpenes, flavonoids, lignans and norlignans) with potential application in different fields, particularly in the agrochemical, food, cosmeceutical, pharmaceutical, phytomedicine and esthetic, due to their valuable multi-bioactivities determined over the last decades. Thus, this review provides an overview of the reported biological activities of organic extracts/fractions and their specialized metabolites obtained from different parts of C. japonica, in order to encourage the alternative uses of C. japonica wastes/byproducts, and implement a sustainable and circular bioeconomy.


Asunto(s)
Cryptomeria , Cupressaceae , Lignanos , Aceites Volátiles , Animales , Cupressaceae/química , Cryptomeria/química , Cryptomeria/metabolismo , Lignanos/metabolismo , Aceites Volátiles/química , Madera/metabolismo
5.
Chem Pharm Bull (Tokyo) ; 70(10): 720-725, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-36184455

RESUMEN

Five podophyllotoxin derivatives (1-5), two diterpenoids (6 and 7), three diterpenoid xylosides (8-10), a flavanonol glycoside (11), flavonol (12), and biflavonoid (13) were isolated from the leaves of Thujopsis dolabrata (Cupressaceae). Compounds 1, 6, and 8 were named (-)-ß-isopeltatin, epi-nootkastatin 2, and acetoxyanticopalol 15-O-ß-D-xylopyranoside, respectively. The structures of the isolated compounds were determined based on a detailed analysis of NMR spectroscopic data and through chromatographic and spectroscopic analyses following specific chemical transformations. The isolated compounds (1-5 and 7-11) were evaluated for their cytotoxicity toward HL-60 human promyelocytic leukemia cells and Caki-1 human kidney carcinoma cells. The podophyllotoxin derivatives (1-5) exhibited cytotoxicity against both HL-60 and Caki-1 cells with IC50 values ranging from 0.00069 to 5.4 µM, and the diterpenoid derivatives (7-10) demonstrated cytotoxicity against HL-60 cells with IC50 values ranging from 4.5 to 11 µM. HL-60 cells treated with 8 exhibited apoptosis characteristics, such as accumulation of sub-G1 cells and nuclear chromatin condensation.


Asunto(s)
Antineoplásicos Fitogénicos , Biflavonoides , Cupressaceae , Diterpenos , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cromatina , Cupressaceae/química , Diterpenos/farmacología , Flavonoles , Glicósidos/análisis , Células HL-60 , Humanos , Hojas de la Planta/química , Podofilotoxina/análisis
6.
Molecules ; 27(2)2022 01 10.
Artículo en Inglés | MEDLINE | ID: mdl-35056749

RESUMEN

Five new dimer compounds, namely Taiwaniacryptodimers A-E (1-5), were isolated from the methanol extract of the roots of Taiwania cryptomerioides. Their structures were established by mean of spectroscopic analysis and comparison of NMR data with those of known analogues. Their antifungal activities were also evaluated. Our results indicated that metabolites 1, 2, 4, and 5 displayed moderate antifungal activities against Aspergillus niger, Penicillium italicum, Candida albicans, and Saccharomyces cerevisiae.


Asunto(s)
Antifúngicos/química , Antifúngicos/farmacología , Cupressaceae/química , Raíces de Plantas/química , Antifúngicos/aislamiento & purificación , Aspergillus niger/efectos de los fármacos , Candida albicans/efectos de los fármacos , Dimerización , Evaluación Preclínica de Medicamentos , Espectroscopía de Resonancia Magnética , Metanol/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Penicillium/efectos de los fármacos , Extractos Vegetales/química
7.
Molecules ; 26(22)2021 Nov 17.
Artículo en Inglés | MEDLINE | ID: mdl-34834029

RESUMEN

Haematobia irritans is a cosmopolitan obligate blood-feeding ectoparasite of cattle and is the major global pest of livestock production. Currently, H. irritans management is largely dependent on broad-spectrum pesticides, which has led to the development of insecticide resistance. Thus, alternative control methods are needed. Essential oils have been studied as an alternative due to their wide spectrum of biological activities against insects. Thus, the main aim of this study was to evaluate the insecticidal, repellent and antifeedant activity of the essential oils from Blepharocalyx cruckshanksii leaves and Pilgerodendron uviferum heartwood against horn flies in laboratory conditions. The composition of the essential oils was analyzed using gas chromatography coupled to mass spectrometry. Accordingly, α-pinene (36.50%) and limonene (20.50%) were the principal components of the B. cruckchanksii essential oil, and δ-cadinol (24.16%), cubenol (22.64%), 15-copaenol (15.46%) and δ-cadinene (10.81%) were the most abundant compounds in the P. uviferum essential oil. Mortality of flies and feeding behavior were evaluated by non-choice tests, and olfactory response was evaluated using a Y-tube olfactometer. Both essential oils were toxic to horn flies, with LC50 values for B. cruckchanksii essential oil of 3.58 µL L-1 air at 4 h, and for P. uviferum essential oil of 9.41 µL L-1 air and 1.02 µL L-1 air at 1 and 4 h, respectively. Moreover, the essential oils exhibited spatial repellency in the olfactometer using only 10 µg of each oil, and these significantly reduced the horn fly feeding at all doses evaluated. Although further laboratory and field studies related to the insectistatic and insecticide properties of these essential oils against H. irritans are necessary, B. cruckshanksii leaves and P. uviferum heartwood essential oils are promising candidates for horn fly management.


Asunto(s)
Cupressaceae/química , Repelentes de Insectos , Muscidae/metabolismo , Myrtaceae/química , Aceites Volátiles , Hojas de la Planta/química , Animales , Bovinos , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Insecticidas/química , Insecticidas/farmacología , Aceites Volátiles/química , Aceites Volátiles/farmacología
8.
Anal Bioanal Chem ; 413(23): 5789-5798, 2021 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-34322736

RESUMEN

In recent years, the invasive cypress bark beetle (Phloeosinus aubei) has caused extensive damage to Platycladus orientalis plants in China, but its infestation is hard to monitor in the early stages. In this study, gas chromatography-mass spectrometry (GC-MS) was initially employed to investigate the volatile organic compound (VOC) emissions of P. aubei-infested P. orientalis saplings. The emissions of total sesquiterpenes were dominating (84-86% of total VOCs) and increased by 3.09-fold in P. aubei-damaged P. orientalis samples compared to undamaged samples, and the monoterpenes, aromatic compounds, and ketone emissions also had varying degrees of increase between 1.39-fold and 5.65-fold. Based on this variation, gas chromatography-ion mobility spectrometry (GC-IMS) was applied, as an untargeted analytical approach, to discriminate P. orientalis samples with different invasive severity. Two different features derived from GC-IMS data were adopted as the input information for classification and prediction models. Results showed that grid search support vector machine (GS-SVM) combined with multilinear principal component analysis (MPCA) based on spectral fingerprint achieved the best classification performances (> 88.98%), and partial least squares discriminant analysis (PLSR) method can accurately predict the pest numbers (R2 > 0.9423 and RMSE < 0.9827). In a word, the VOC profiling-based approach had the potential for evaluating P. aubei invasive severity and pest management.


Asunto(s)
Escarabajos/efectos de los fármacos , Cupressaceae/química , Cromatografía de Gases y Espectrometría de Masas/métodos , Especies Introducidas , Control de Plagas/métodos , Compuestos Orgánicos Volátiles/farmacología , Animales , China
9.
Molecules ; 26(4)2021 Feb 19.
Artículo en Inglés | MEDLINE | ID: mdl-33669825

RESUMEN

The aim of the present research was to determine the chemical composition and the cytotoxic effects of Tetraclinis articulata trunk bark essential oil (HEE) obtained by steam distillation and five fractions obtained by normal phase silica chromatographic separation. Chemical analysis allowed the identification of 54 known compounds. Relatively high amounts of oxygenated sesquiterpenes (44.4-70.2%) were detected, mainly consisting of caryophyllene oxide (13.1-26.6%), carotol (9.2-21.2%),14-hydroxy-9-epi-(E)-caryophyllene (3.2-15.5%) and humulene epoxide II (2.6-7.2%). The cytotoxic activity against human mammary carcinoma cell lines (MDA-MB-231) and colorectal carcinoma cell lines (SW620) of the essential oil and its fractions were assessed. All the samples displayed moderate to weak activity compared to 5-fluorouracil. The colorectal carcinoma cell line was relatively more sensitive to the essential oil and its fractions compared to the breast cancer cell line, showing IC50 values from 25.7 to 96.5 µg/mL. In addition, the essential oil and its fraction E.2 revealed a cytotoxic activity against colorectal carcinoma cell line, with IC50 values lower than 30 µg/mL. This is the first report on the chemical composition and cytotoxic activity of the trunk bark essential oil of T. articulata.


Asunto(s)
Cupressaceae/química , Cupressaceae/crecimiento & desarrollo , Aceites Volátiles/química , Aceites Volátiles/farmacología , Corteza de la Planta/química , Muerte Celular/efectos de los fármacos , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Fraccionamiento Químico , Humanos , Concentración 50 Inhibidora , Túnez
10.
J Food Drug Anal ; 29(4): 606-621, 2021 12 15.
Artículo en Inglés | MEDLINE | ID: mdl-35649142

RESUMEN

Eight new diterpenes, 6α,7ß-dihydroxyferruginol (1), 6α,7α-dihydroxyferruginol (2), 6α-hydroxyhinokiol (3), 4α-hydroxy-7-oxo-18-norabieta-8,11,13-trien-4α-ol (4a), 15,16-dehydrosugiol (5), 7-methoxy-6,7-secoabieta-8,11,13-triene-6,12-diol (6), 7α-acetoxyabieta-8,12-diene-11,14-dione (7), 7α-butyloxyethyloxyabieta-8,12-diene-11,14-dione (8), along with four known compounds, 6,7-dehydroferruginol (9), 12-hydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial (10), 7α-11-dihydroxy-12-methoxy-8,11,13-abietatriene (11), and 11,14-dihydroxy-8,11,13-abietatrien-7-one (12) were successfully isolated from the bark of Calocedrus macrolepis var. formosana. The structures of all isolates were elucidated by physical data (appearance, UV, IR, optical rotation) and spectroscopic data (1D, 2D NMR, and HREIMS). Compounds 9, 10, 11, and 12 showed promising growth-inhibitory effect on human lymphatic endothelial cells (LECs). Among these compounds, compound 10 exerted the most potent anti-lymphangiogenesis property by suppressing cell growth and tube formation of LECs. In conclusion, the results revealed the anti-lymphangiogenic potentials of Formosan C. macrolepis var. formosana.


Asunto(s)
Cupressaceae , Diterpenos , Cupressaceae/química , Diterpenos/análisis , Diterpenos/química , Diterpenos/farmacología , Células Endoteliales , Humanos , Espectroscopía de Resonancia Magnética , Corteza de la Planta/química
11.
Molecules ; 25(4)2020 Feb 20.
Artículo en Inglés | MEDLINE | ID: mdl-32093424

RESUMEN

Taiwania flousiana (T. flousiana) Gaussen is a precious wood in the family Taxodiaceae. This study investigated the chemical components of the essential oil from the stem bark of T. flousiana and its algicidal, antifungal, and antioxidant properties. Sixty-nine compounds representing 89.70% of the stem bark essential oil were identified by GC-MS. The essential oil showed strong anti-algae, anti-bacteria, and anti-fungus activities against the tested species, and antioxidant activities. The IC50 values of the essential oil against chlorophyll a, chlorophyll b, and the total chlorophyll of Spirogyra communis (a species of algae), 24-96 h after the treatment, ranged from 31.77 to 84.92 µg/mL, while the IC50 values of butachlor ranged from 40.24 to 58.09 µg/mL. Ultrastructure changes revealed by the transmission electron microscopy indicated that the main algicidal action sites were the chloroplast and cell wall. The essential oil showed antifungal activities on Rhizoctonia solani (EC50 = 287.94 µg/mL) and Colletotrichum gloeosporioiles (EC50 = 378.90 µg/mL). It also showed bactericidal activities on Ralstonia solanacearum and Staphylococcus aureus, with zones of inhibition (ZOIs) being 18.66 and 16.75 mm, respectively at 40 µg/disk. Additionally, the essential oil possessed antioxidant activity estimated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) method (IC50 = 33.51 µg/mL; IC50 value of the positive control ascorbic acid was 7.98 µg/mL). Thus, the essential oil of this plant might be used as a possible source of natural bioactive molecules in agrochemical industry as well as in food and cosmetic industries.


Asunto(s)
Antioxidantes , Cupressaceae/química , Aceites Volátiles , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Colletotrichum/crecimiento & desarrollo , Aceites Volátiles/química , Aceites Volátiles/farmacología , Ralstonia solanacearum/crecimiento & desarrollo , Rhizoctonia/crecimiento & desarrollo , Spirogyra/crecimiento & desarrollo , Staphylococcus aureus/crecimiento & desarrollo
12.
Nat Prod Res ; 34(12): 1763-1771, 2020 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-30600693

RESUMEN

Investigation of Platycladus orientalis yielded five flavonoids, including aglycone flavone 1 (apigenin), flavone glycoside 2 (apigenin 7-O-ß-D-glucopyranoside), new gernaylated flavone glycoside 3 (apigenin 8-gernayl-4'-O-α-gluco pyranoside) and two new pernylated flavonoid glycosides 4 & 5 (apigenin 8-pernyl-4'-glucopyranosyl-7-O-α-glucopyranoside and apigenin 5-pernyl-7-glucopyranosyl-4'-O-ß-D-glucopyranoside). Their structures were elucidated on the basis of spectroscopic evidence. The cytotoxicity of compounds 1-5 were tested against Lung adenocarcinoma (A549), human hepatocellular liver carcinoma (HepG2), human breast carcinoma (MCF-7) cell lines and mouse fibroblast cell line NIH/3T3 as normal cells. This assay gave spot on structure activity relationship which, showed that cytotoxicity of compounds (1) and (2) against three cell lines was weak as IC50 > 15. Compounds (4) and (5) had moderate cytotoxic and no toxic effect on normal cell. Compound (3) showed high cytotoxic activity against tested three cell lines with no toxic effect of normal cells.[Formula: see text].


Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Cupressaceae/química , Flavonoides/aislamiento & purificación , Glicósidos/aislamiento & purificación , Componentes Aéreos de las Plantas/química , Animales , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular , Línea Celular Tumoral , Flavonoides/química , Flavonoides/toxicidad , Glicósidos/química , Glicósidos/farmacología , Humanos , Ratones , Estructura Molecular , Extractos Vegetales/química , Relación Estructura-Actividad
13.
J Cosmet Dermatol ; 19(5): 1254-1259, 2020 May.
Artículo en Inglés | MEDLINE | ID: mdl-31486569

RESUMEN

BACKGROUND: Fitzroya cupressoides, commonly known as alerce, is an endemic conifer unique to southern South America. Alerce wood is renowned for its durability and resistance to biological degradation due to the presence of a particular class of secondary metabolite. Alerce extracts have been used in traditional medicine for different skin lesion treatments. AIMS: To develop a cell culture system to produce alerce extract and evaluate its cytotoxicity and effects on in vitro wound healing. METHODS: Cell cultures and aqueous extracts were prepared from alerce needles. Cytotoxicity was evaluated in keratinocytes (HaCaT line) and melanocites (C32 line) using the XTT assay. Wound healing was assayed with the scratch test in HaCaT cells, using mitomycin C to evaluate the role of cell division in the wound closure. RESULTS: Alerce cell culture extract has a significant effect on wound healing at different concentrations. No positive effects on the viability of normal and cancerous skin cells were observed. These results suggest that alerce extracts stimulate cell division in human skin epidermal cells in the context of wound repair. CONCLUSIONS: Bioactive compounds extracted from alerce cell cultures show promise as ingredients in dermocosmetic formulations, but further clinical studies are required to support these findings at the tissue level.


Asunto(s)
Extractos Celulares/farmacología , Cosmecéuticos/farmacología , Cupressaceae/química , Extractos Vegetales/farmacología , Cicatrización de Heridas/efectos de los fármacos , Técnicas de Cultivo de Célula , Extractos Celulares/aislamiento & purificación , Línea Celular , Supervivencia Celular/efectos de los fármacos , Cosmecéuticos/aislamiento & purificación , Cupressaceae/citología , Humanos , Queratinocitos , Melanocortinas , Extractos Vegetales/aislamiento & purificación , Pruebas de Toxicidad Aguda
14.
Molecules ; 24(17)2019 Aug 21.
Artículo en Inglés | MEDLINE | ID: mdl-31438610

RESUMEN

The resins bled from stems and in seed cones and leaves of Cryptomeria japonica, Glyptostrobus pensilis, Taxodium distichum, and T. mucronatum were characterized to provide an overview of their major natural product compositions. The total solvent extract solutions were analyzed as the free and derivatized products by gas chromatography-mass spectrometry to identify the compounds, which comprised minor mono- and sesquiterpenoids, and dominant di- and triterpenoids, plus aliphatic lipids (e.g., n-nonacosan-10-ol). Ferruginol, 7α-p-cymenylferruginol, and chamaecydin were the major characteristic markers for the Taxodioideae conifer subfamily. The mass spectrometric data can aid polar compound elucidation in environmental, geological, archeological, forensic and pharmaceutical studies.


Asunto(s)
Cupressaceae/química , Cromatografía de Gases y Espectrometría de Masas/métodos , Taxodium/química , Terpenos/análisis
15.
J Nat Prod ; 82(8): 2087-2093, 2019 08 23.
Artículo en Inglés | MEDLINE | ID: mdl-31347365

RESUMEN

Two uncommon C37 heterodimeric diterpenoids, taicrypnacids A (1) and B (2), and a known labdane-type diterpenoid (3) were isolated from the leaves of Taiwania cryptomerioides. Several techniques, such as comprehensive spectroscopic analysis, chemical conversion, X-ray crystallography, and ECD data, were employed to define the structures. The two new compounds displayed cytotoxicity against human breast cancer (MCF-7), osteosarcoma (U-2 OS), and human colon carcinoma (HCT-116) cell lines, while the methyl ester 1a showed no activity. Compound 1 induced Ca2+-ROS pathway-mediated endoplasmic reticulum stress, and excessive stress led to cell death by activating apoptosis and autophagy.


Asunto(s)
Cupressaceae/química , Diterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Dimerización , Diterpenos/química , Ensayos de Selección de Medicamentos Antitumorales , Células HCT116 , Humanos , Células MCF-7 , Estructura Molecular , Análisis Espectral/métodos , Estereoisomerismo
16.
Carbohydr Polym ; 213: 276-285, 2019 Jun 01.
Artículo en Inglés | MEDLINE | ID: mdl-30879670

RESUMEN

The structure and bioactivity of a novel polysaccharide from Platycladus orientalis (L.) Franco leaves (POP2) were investigated in the present study. Structure characterization demonstrated that the average molecular weight of POP2 was 9.69 kDa and consisted of arabinose (14.39%), mannose (10.24%), glucose (63.95%) and galactose (11.42%). The main linkage types of POP2 consisted of (1→4)-linked α-d-Glc and (1→6)-linked α-d-Glc based on methylation and NMR analysis. Bioactivity evaluation showed that POP2 could effectively promote the secretion of inflammatory cytokines (IL-6 and TNF-α), as well as the anti-inflammatory cytokines (IL-10) in LPS-induced cells. Besides, the secretion of NO was significantly inhibited by POP2 in M1 model. POP2 could enhance the level of inflammatory cytokines (NO, IL-6 and TNF-α), while the secretion of the anti-inflammatory cytokine TGF-ß was markedly suppressed in IL-4 induced cells. Our work attempted to elucidate the regulation of macrophage polarization and support the potential application of POP2 as bioactive ingredient for functional foods.


Asunto(s)
Cupressaceae/química , Macrófagos/efectos de los fármacos , Polisacáridos/farmacología , Animales , Polaridad Celular/efectos de los fármacos , Células Cultivadas , Macrófagos/metabolismo , Ratones , Hojas de la Planta/química , Polisacáridos/química , Polisacáridos/aislamiento & purificación , Células RAW 264.7
17.
Phytochemistry ; 161: 86-96, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-30822624

RESUMEN

A phytochemical study on the stem bark of Metasequoia glyptostroboides led to the isolation of sixty-one diterpenoids and sesquiterpenoids, including seventeen previously undescribed compounds, metaglyptins A-Q. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, and 1H, 13C and 2D NMR). The absolute configurations of metaglyptins I, J, and O were determined by the ECD data and single-crystal X-ray diffraction analysis. The undescribed compounds were evaluated for their cytotoxicity against HeLa, AGS, and MDA-MB-231 cancer cell lines. The results revealed that metaglyptin A exhibited moderate cytotoxicity against MDA-MB-231 cell line with IC50 value of 20.02 µM.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Cupressaceae/química , Diterpenos/farmacología , Corteza de la Planta/química , Tallos de la Planta/química , Sesquiterpenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Cristalografía por Rayos X , Diterpenos/química , Diterpenos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Células HeLa , Humanos , Modelos Moleculares , Conformación Molecular , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Relación Estructura-Actividad
18.
J Food Sci ; 84(3): 667-677, 2019 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-30779137

RESUMEN

The polyphenols (PF) from Platycladus Orientalis (L.) Franco leaves were purified by using 10 different macroporous adsorption resins. HPD-722 resin showed the best adsorption and desorption capacities. The static and dynamic adsorption and desorption of PF on HPD-722 resin were studied and the total polyphenols were separated into two fractions, PF-A and PF-B. PF-A and PF-B demonstrated similar scavenging activity of free radical (DPPH, ABTS, hydroxyl radical, superoxide anion). The scavenging activity of PF-A and PF-B on hydroxyl radical and superoxide anion radical reached the equal levels of vitamin C and gallic acid. The IC50 value of PF-A for hydroxyl radical scavenging activity and superoxide anion radical scavenging activity were 0.50 and 0.56 mg/mL, while those of PF-B were 0.61 and 0.64 mg/mL. PF-A and PF-B could reduce the overproduction of inflammatory cytokines (TNF-α, Pro-IL-1ß, and IL-6) induced by lipopolysaccharide and their protein expression in THP-1 cells. PF-B exhibited better anti-inflammatory effect than PF-A in the dosage range of 1.0-4.0 µg/mL. Structural identification of PF-A and PF-B were conducted by HPLC-MS/MS. Ten polyphenol compounds were identified in PF-A and PF-B, respectively, by HPLC-MS/MS, including quercetin, apigenin, myricetin, and so on. Molecular docking studies indicated that apigenin, myricetin, luteolin, kaempferol, and quercetin effectively inhibit xanthine oxidase by forming hydrogen bonds with the amino acid residues and binding to the active site of the enzyme. The results might supply useful information for better understanding the chemical structure, antioxidant, and anti-inflammatory activities of Platycladuso (L.) Franco leaves polyphenols. PRACTICAL APPLICATION: This study demonstrated that polyphenols from P. orientalis (L.) Franco leaves have the potential applications as functional food ingredient for the prevention and treatment of gout and inflammation, hyperuricemia and gout.


Asunto(s)
Cupressaceae/química , Polifenoles/química , Antioxidantes , Línea Celular Tumoral , Cromatografía Líquida de Alta Presión , Citocinas/genética , Citocinas/metabolismo , Depuradores de Radicales Libres , Regulación de la Expresión Génica/efectos de los fármacos , Humanos , Simulación del Acoplamiento Molecular , Extractos Vegetales , Hojas de la Planta/química , Superóxidos , Espectrometría de Masas en Tándem
19.
Phytomedicine ; 56: 57-63, 2019 Mar 15.
Artículo en Inglés | MEDLINE | ID: mdl-30668354

RESUMEN

BACKGROUND: Tetraclinis articulata is used in traditional medicine and has been reported to possess antibacterial, antifungal, cytotoxic, anti-inflammatory and antioxidant properties. PURPOSE: This study investigated the effects of T. articulata essential oil on memory and brain oxidative stress in amyloid-ß peptide 1-42 (Aß1-42)-induced an Alzheimer's disease amyloidosis model. Moreover, the underlying mechanism for memory enhancement and antioxidant activity was investigated, thus supporting its traditional use with scientific evidence for further studies. METHODS: T. articulata essential oil was administered by inhalation to male Wistar rats once daily for 15 min period at doses of 1% and 3% for 21 days after the intracerebroventricular administration of Aß1-42 right-unilaterally to induce memory deficits. The chemical composition of the essential oil was done by GC-MS and GC-FID. Spatial memory of rats was tested using Y-maze and radial arm maze tests. The possible underlying mechanism for memory improvement exhibited by T. articulata essential oil was investigated by in vivo brain antioxidant effect and acetylcholinesterase (AChE) inhibitory effect. In vitro, experimental evaluations were assessed through DPPH and ABTS tests. RESULTS: The GC-MS and GC-FID data showed that the essential oil has a high percent of monoterpene hydrocarbons. Also, we demonstrated the essential oil reversed the Aß1-42-induced decreasing of the spontaneous alternation in the Y-maze test and the Aß1-42-induced increasing of the working and reference memory errors in the radial arm maze test. Furthermore, the Aß1-42-decreased the acetylcholinesterase activity and the oxidant-antioxidant status in the rat hippocampus was retrieved by the treatment with the essential oil. CONCLUSION: The study demonstrates that the essential oil could be a potent pharmacological agent against dementia by modulating cholinergic activity and promoting antioxidant action in the rat hippocampus.


Asunto(s)
Enfermedad de Alzheimer/tratamiento farmacológico , Encéfalo/efectos de los fármacos , Trastornos del Conocimiento/tratamiento farmacológico , Cupressaceae/química , Aceites Volátiles/farmacología , Enfermedad de Alzheimer/metabolismo , Enfermedad de Alzheimer/fisiopatología , Péptidos beta-Amiloides/toxicidad , Amiloidosis/inducido químicamente , Animales , Antioxidantes/farmacología , Encéfalo/metabolismo , Encéfalo/fisiopatología , Inhibidores de la Colinesterasa/farmacología , Trastornos del Conocimiento/metabolismo , Disfunción Cognitiva/tratamiento farmacológico , Modelos Animales de Enfermedad , Masculino , Trastornos de la Memoria/tratamiento farmacológico , Aceites Volátiles/química , Estrés Oxidativo/efectos de los fármacos , Fragmentos de Péptidos/toxicidad , Ratas Wistar , Memoria Espacial/efectos de los fármacos
20.
Molecules ; 23(12)2018 Dec 19.
Artículo en Inglés | MEDLINE | ID: mdl-30572688

RESUMEN

The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species (Cupressaceae) based on gas chromatography-mass spectrometry have not been reported. Results show that diterpenoids were the most abundant components and callitrisic acid was present in the resin extracts of all Callitris species analyzed. Significant amounts of 4-epi-pimaric and sandaracopimaric acids, with lesser communic, ozic, and lambertianic acids, were also in the mixtures. Phenolic diterpenoids, for example, ferruginol, hinokiol, were found in trace quantities in some samples. Thus, callitrisic acid and 4-epi-pimaric acid are the characteristic diterpenoids of Callitris species that are amenable to molecular biomarker analyses in geological or environmental applications.


Asunto(s)
Cupressaceae/química , Resinas de Plantas/química , Terpenos/química , Cromatografía de Gases y Espectrometría de Masas
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