Seven drimane-type sesquiterpenoids from an earwig-associated Aspergillus sp / 中国天然药物

Drimane-type sesquiterpenoids are widely distributed in fungi. From the ethyl acetate extract of the earwig-derived Aspergillus sp. NF2396, seven new drimane-type sesquiterpenoids, named drimanenoids A-G (1-7), were isolated. Their structures were elucidated by diverse spectroscopic analysis including high-resolution ESI-MS, one- and two-dimensional NMR spectroscopy. Drimanenoids A-F (1-6) are new members of drimane-type sesquiterpenoid esterified with unsaturated fatty acid side chain at C-6. Drimanenoids C (3), D (4) and F (6) showed antibacterial activity against five types of bacteria with different inhibition diameters. Drimanenoid D (4) exhibited moderate cytotoxicity against human myelogenous leukemia cell line K562 with an IC50 value of 12.88 ± 0.11 μmol·L-1.

Anti-inflammatory effects and acute oral toxicity of Copaifera spp. essential oil-loaded nanoemulsion / Efectos antiinflamatorios y toxicidad oral aguda de nanoemulsión cargada de aceite esencial de Copaifera spp

Copaifera spp. essential oil (EOC) was extracted by hydrodistillation of Copaifera oleoresin (COR). The EOC was characterized by GC/MS and a novel EOC-loaded nanoemulsion was developed to enhance the EOC solubility and to evaluate its utility as antinflammatory. EOC contain 14 volatile compounds (including ß-caryophyllene: 51.52%) having a required HLB of 11. The Surfactant: EOC: Water ratio of 13:15:75 (%, w:w:w) produced the optimal formulation (particle size: 94.47 nm). The EOC-loaded nanoemulsion presented a pseudoplastic/thixotropic behavior with excellent shelf stability for 6 months. The anti-inflammatory effect of the nanoemulsion was more potent than that of the EOC, and statistically equal to diclofenac (50 mg/kg). The EOC-loaded nanoemulsion showed no oral acute toxicity (in mice) at 2000 mg/kg; hence, it is considered a nontoxic product. The development of the EOC-loaded nanoemulsion added value to both the COR and the EOC by providinga suitable formulation that could be used as an anti-inflammatory product.

El aceite esencial (EOC) fue extraído por hidrodestilación de oleoresina de Copaifera spp. El EOC fue caracterizado químicamente por GC/MS. Se formuló una nanoemulsión con EOC para mejorar la solubilidad del EOC y evaluar su utilidad como antiinflamatorio. El EOC contiene 14 compuestos volátiles (incluido el ß-cariofileno: 51,52%) con un HLB requerido de 11. La relación Tensioactivo: EOC: Agua de 13:15:75 (%, p:p:p) produjo la formulación óptima (tamaño de partícula: 94,47 nm).. La nanoemulsión cargada con EOC presentó un comportamiento pseudoplástico/tixotrópico con una excelente estabilidad en almacenamiento durante 6 meses. El efecto antiinflamatorio de la nanoemulsión fue más potente que el del EOC y estadísticamente igual al diclofenaco (50 mg/kg). La nanoemulsión cargada con COE no mostró toxicidad aguda oral (en ratones) a 2000 mg/kg; por lo tanto, se considera un producto no tóxico. El desarrollo de la nanoemulsión cargada con EOC agregó valor tanto al COR como al EOC al proporcionar una formulación adecuada que podría usarse como un producto antiinflamatorio.

Sesquiterpenoids from the leaves of Sarcandra glabra / 中国天然药物

Sarglanoids A-F, six new sesquiterpenoids belonging to eudesmane (1-5) and eremophilane (6) types, were isolated from the leaves of Sarcandra glabra, a famous traditional Chinese medicine (TCM). Their structures including absolute configurations were elucidated through extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. Compounds 1-2 were rare N-containing eudesmane-type sesquiterpenoids. Compound 3 exhibited inhibitory activity against nitric oxide (NO) production in lipopolysaccharides (LPS)-induced RAW 264.7 cells with IC50 values at 20.00 ± 1.30 μmol·L-1. These findings provide scientific evidence for sesquiterpenoids as the material foundation of S. glabra.

Seasonal variation in the essential oil from Varronia curassavica jacq. accessions / Variación estacional en el aceite esencial de accesiones de Varronia curassavica Jacq

Varronia curassavica has anti-inflammatory properties because of the terpenes, α-humulene and ß-caryophyllene, present in the essential oil. The objective of this study was to evaluate the influence of seasonality on the essential oil of V. curassavica accessions. Leaves from six accessions were collected from the Germplasm Bank of the Federal University of Minas Gerais over 12 months. Correlations between the essential oil content and meteorological factors were determined. Gas chromatography analysis coupled with mass spectrometry was conducted to determine the chemical composition of the essential oil. The content and chemical composition of the oil varied throughout the year. Relative humidity was correlated with accessions ICA-VC2 (-0.64) and ICA-VC4 (0.68). ß-bourbonene, ß-elemene, spathulenol, germacrene, caryophyllene oxide, α-humulene, and ß-caryophyllene occurred in all accessions. Accession ICA-VC3 exhibited lower variation (22.17%), higher average (0.97%) essential oil, and maintained an average abundance of α-humulene greater than 2.6%, which is the amount necessary for phytotherapeutics.

Varronia curassavica tiene propiedades antiinflamatorias debido a los terpenos, α-humuleno y ß-cariofileno, presentes en el aceite esencial. El objetivo de este estudio fue evaluar la influencia de la estacionalidad en el aceite esencial de las accesiones de V. curassavica. Se recolectaron hojas de seis accesiones del Banco de Germoplasma de la Universidad Federal de Minas Gerais durante 12 meses. Se determinaron las correlaciones entre el contenido de aceite esencial y los factores meteorológicos. Se realizó un análisis de cromatografía de gases junto con espectrometría de masas para determinar la composición química del aceite esencial. El contenido y la composición química del aceite varió a lo largo del año. La humedad relativa se correlacionó con las accesiones ICA-VC2 (-0,64) e ICA-VC4 (0,68). En todas las accesiones aparecieron ß-bourboneno, ß-elemeno, espatulenol, germacreno, óxido de cariofileno, α-humuleno y ß-cariofileno. La accesión ICA-VC3 mostró una menor variación (22,17%), un promedio más alto (0,97%) de aceite esencial y mantuvo una abundancia media de α-humuleno superior al 2,6%, que es la cantidad necesaria para los fitoterápicos.

Advances in biosynthesis of cadinane sesquiterpenes / 生物工程学报

Cadinanes are a class of bicyclic sesquiterpenes with complex stereochemistry and broad pharmacological activities, such as antibacterial, anti-inflammatory, and hypoglycemic activities. To date, structurally diverse and bioactive cadinane sesquiterpenes have been isolated and identified from a variety of plants and microorganisms. Moreover, deeper understandings on cadinane sesquiterpene synthases have been made. This article categorized the 124 new cadinanes which were published in the literatures in the past four years (2017-2020) into five structural types, and presented their pharmacological activities. We also illustrated the elucidation of the biosynthetic pathways for typical cadinanes, summarized the research progress on cadinane sesquiterpene synthases. Finally, current challenges and future prospects were proposed and discussed.

Antibacterial and antiproliferative activities of the fresh leaf essential oil of Psidium guajava L. (Myrtaceae) / Atividades antibacteriana e antiproliferativa do óleo essencial das folhas frescas de Psidium guajava L. (Myrtaceae)

Abstract This study evaluated the antibacterial and antiproliferative activities of the essential oil of Psidium guajava leaves (PG-EO), traditionally used in folk medicine. The essential oil was obtained from fresh leaves by hydrodistillation, using a modified Clevenger apparatus. The major PG-EO chemical constituents were identified by GC-MS and GC-FID as being β-caryophyllene (16.1%), α-humulene (11.9%), aromadendrene oxide (14.7%), δ-selinene (13.6%), and selin-11-en-4α-ol (12.5%). The antibacterial activity of the essential oil of P. guajava leaves was determined in terms of its minimum inhibitory concentrations (MIC) using the broth microdilution method in 96-well microplates. PG-EO had moderate activity against Streptococcus mutans (MIC = 200 µg/mL), S. mitis (MIC = 200 µg/mL), S. sanguinis (MIC = 400 µg/mL), S. sobrinus (MIC = 100 µg/mL), and S. salivarius (MIC = 200 µg/mL). The antiproliferative activity was evaluated against different tumor cell lines: breast adenocarcinoma (MCF-7), human cervical adenocarcinoma (HeLa), and human gliobastoma (M059J). A normal human cell line (GM07492A, lung fibroblasts) was included. The antiproliferative activity was evaluated using the XTT assay and the results were expressed as IC50. The essential oil showed significantly lower IC50 values against MCF-7 and M059J lines than that obtained for the normal line, showing selectivity. Our results suggest that the essential oil of Psidium guajava L. has promising biological activities and can be considered a new source of bioactive compounds.

Resumo Este estudo avaliou as atividades antibacteriana e antiproliferativa do óleo essencial das folhas frescas de Psidium guajava (PG-OE), tradicionalmente utilizadas na medicina popular. O óleo essencial foi obtido por hidrodestilação das folhas frescas, utilizando aparelho do tipo Clevenger. Os principais constituintes químicos de PG-OE identificados por CG-EM e CG-DIC foram: β-cariofileno (16,1%), α-humuleno (11,9%), óxido de aromadendreno (14,7%), δ-selineno (13,6%) e selin-11-en-4α-ol (12,5%). A atividade antibacteriana do óleo essencial das folhas de P. guajava foi determinada em termo de sua concentração inibitória mínima (CIM) utilizando o método de microdiluição de caldo em microplacas de 96 poços. PG-OE apresentou moderada atividade contra Streptococcus mutans (CIM = 200 μg/mL), S. mitis (CIM = 200 μg/mL), S. sanguinis (CIM = 400 μg/mL), S. sobrinus (CIM = 100 μg/mL) e S. salivarius (CIM = 200 μg/mL). A atividade antiproliferativa foi avaliada frente a diferentes linhagens de células tumorais como: adenocarcinoma de mama (MCF-7), adenocarcinoma cervical humano (HeLa) e gliobastoma humano (M059J). Foi incluída uma linhagem celular humana normal (GM07492A, fibroblastos pulmonares). A atividade antiproliferativa foi avaliada utilizando o ensaio XTT e os resultados foram expressos como CI50. As linhagens MCF-7 e M059J mostraram valores significativamente mais baixos de CI50 do que os obtidos para a linhagem normal, mostrando seletividade. Nossos resultados sugerem que o óleo essencial das folhas frescas de Psidium guajava L. possui atividades biológicas promissoras e pode ser considerado como uma nova fonte de compostos bioativos.

Chemical Composition and Antibacterial Activity of the Essential Oil of Vitex agnus-castus L. (Lamiaceae)

ABSTRACT Abnormal multiplication of oral bacteria causes dental caries and dental plaque. These diseases continue to be major public health concerns worldwide, mainly in developing countries. In this study, the chemical composition and antimicrobial activity of the essential oil of Vitex agnus-castus leaves (VAC‒EO) collected in the North of Brazil against a representative panel of cariogenic bacteria were investigated. The antimicrobial activity of VAC-EO was evaluated in terms of its minimum inhibitory concentration (MIC) values by using the broth microdilution method in 96-well microplates. The chemical constituents of VAC-EO were identified by gas chromatography (GC‒FID) and gas chromatography‒mass spectrometry (GC‒MS). VAC‒EO displayed some activity against all the investigated oral pathogens; MIC values ranged from 15.6 to 200 μg/mL. VAC-EO had promising activity against Streptococcus mutans (MIC= 15.6 μg/mL), Lactobacillus casei (MIC= 15.6 μg/mL), and Streptococcus mitis (MIC= 31.2 μg/mL). The compounds 1,8-cineole (23.8%), (E)-β-farnesene (14.6%), (E)-caryophyllene (12.5%), sabinene (11.4%), and α-terpinyl acetate (7.7%) were the major chemical constituents of VAC‒EO. VAC-EO displays antimicrobial activity against cariogenic bacteria. The efficacy of VAC-EO against S. mutans is noteworthy and should be further investigated.

Antifungal activities of the essential oil and its fractions rich in sesquiterpenes from leaves of Casearia sylvestris Sw

ABSTRACT Casearia genus (Salicaceae) is found in sub-tropical and tropical regions of the world and comprises about 160-200 species. It is a medicinal plant used in South America, also known as "guaçatonga", "erva-de-tiú", "cafezinho-do-mato". In Brazil, there are about 48 species and 12 are registered in the State of Rio de Janeiro, including Casearia sylvestris Sw. There are many studies related to the chemical profile and cytotoxic activities of extracts from these plants, although few studies about the antifungal potential of the essential oil have been reported. In this work, we have studied the antifungal properties of the essential oil of C. sylvestris leaves, as well as of their fractions, against four yeasts (Saccharomyces cerevisae, Candida albicans, C. glabrata and C. krusei) for the first time. The chemical analysis of the essential oil revealed a very diversified (n = 21 compounds) volatile fraction composed mainly of non-oxygenated sesquiterpenes (72.1%). These sesquiterpenes included α-humulene (17.8%) and α-copaene (8.5%) and the oxygenated sesquiterpene spathulenol (11.8%) were also identified. Monoterpenes were not identified. The fractions are mainly composed of oxygenated sesquiterpenes, and the most active fraction is rich in the sesquiterpene 14-hydroxy -9-epi-β-caryophyllene. This fraction was the most effective in inhibiting the growth of three yeast strains.

Chemical composition, antimicrobial and antioxidant activities of Echinophora platyloba essential oil / Composición química y actividades antimicrobianas y antioxidantes del aceite esencial de Echinophora platyloba

Objetivo: Echinophora platyloba se utiliza tradicionalmente como agente antimicrobiano con el fin de preservar los productos caseros de deterioro. El objetivo de este estudio fue evaluar la composición química del aceite esencial, actividad antimicrobiana y antioxidante del aceite esencial de E. platyloba de la provincia de Shahr-e-Kord. Materiales y métodos: la composición química del aceite esencial de E. platyloba mediante técnicas de GC-MS y GC y evaluar su efecto antibacteriano frente a Staphylococcus aureus, Salmonella enterica y Helicobacter pylori por ensayos de difusión en disco y de micro dilución en caldo. La actividad antioxidante del aceite esencial de E. platyloba se evaluó por los radicales ABST. β-ocimeno y α-cariofileno eran los componentes principales del aceite esencial de E. platyloba. El aceite esencial mostró la actividad antibacteriana prometido contra S. aureus, seguido de S. enterica y H. pylori. El aceite esencial presenta actividad antioxidante del aceite esencial mostró la IC50 de 0. 32 mg/ml que fue mayor que la IC50 de ácido ascórbico (0.20 mg/ml). En conclusión : Aceite esencial de E. platyloba ha se recomienda ß-ocimeno y quimiotipo α-cariofileno y su uso como agentes antioxidantes y antibacterianas como sus usos tradicionales.

Objective: Echinophora platyloba is traditionally used as antimicrobial agent in order to preserve the home-made products from deterioration. The aim of this study was to evaluate chemical composition of essential oil, antimicrobial and antioxidant activity of E. platyloba essential oil from Shahr-E-Kord city, Chaharmahal and Bakhtiari Province. Materials and methods: chemical composition of E. platyloba essential oil by GC and GC-MS techniques and evaluate its antibacterial effect against Staphylococcus aureus, Salmonella enterica and Helicobacter pylori by disc diffusion and micro broth dilution assays. The antioxidant activity of E. platyloba essential oil was evaluated by ABST radicals. β-ocimene and α-caryophyllene were the main components of E. platyloba essential oil. The essential oil showed the promised antibacterial activity against S. aureus, followed by S. enterica and H. pylori. The antioxidant activity evaluation of essential oil showed the IC50 of 0.32 mg/ml that was higher than the IC50 of ascorbic acid (0.20 mg/ml). In conclusion , E. platyloba essential oil has β-ocimene and α-caryophyllene chemotype and its use as antioxidant and antibacterial agents is recommended as its traditional uses.

Chemical composition, antimicrobial, insecticidal, phytotoxic and antioxidant activities of Mediterranean Pinus brutia and Pinus pinea resin essential oils / 中国天然药物

Essential oils of the resins of Pinus brutia and Pinus pinea were evaluated for their biological potential. Essential oils were characterized using GC-MS and GC/FID. in vitro antimicrobial, phytotoxic, antioxidant, and insecticidal activities were carried out using the direct contact and the fumigant assays, respectively. The chemical profile of the essential oils of the resins of P. pinea and P. brutia included mainly α-pinene (21.39% and 25.40%), β-pinene (9.68% and 9.69%), and caryophyllene (9.12% and 4.81%). The essential oils of P. pinea and P. brutia exerted notable antimicrobial activities on Micrococcus luteus and Bacillus subtilis, insecticidal activities on Ephestia kuehniella eggs, phytotoxic activities on Lactuca sativa, Lepidium sativum, and Portulaca oleracea, as well as antioxidant potential. Indications of the biological activities of the essential oils suggest their use in the formulation of ecofriendly and biocompatible pharmaceuticals.