Effect of Terpenes on the enhancement of skin permeation of lipophilic drugs: A systematic review

Objectives@#The stratum corneum (SC) remains an obstacle to the passage of drugs applied topically. Several investigations have focused on enhancing the penetration of drugs through the SC by integrating permeation enhancers (PE) into the drug formulation. Terpenes are among the PE utilized in formulations and are categorized by the regulatory bodies as generally recognized as safe (GRAS). This study aimed to comparatively analyze the skin permeation enhancing effect of terpenes on lipophilic drugs. @*Methods@#The present study reviewed the effects of terpenes on the permeation of lipophilic small-molecule drugs through the skin using original research published between 2000 - 2022 retrieved from PubMed®. The search phrase used was (lipophilic drug) AND (terpene) AND (permeation enhancer). @*Results@#Terpenes increase the percutaneous permeation of lipophilic small molecule drugs by 1.06 – 256.80-fold. Linear correlation analysis of terpenes’ cLog P with enhancement ratio (ER) revealed moderate and strong positive correlations in pig skin (r = 0.21) and mouse skin (r = 0.27), and rat skin (r = 0.41) and human skin (r = 0.67), respectively. Drug cLog P is a poor (r = -0.06) predictor of permeation enhancement. Terpenes with cLog P higher than 2.40 had ER greater than 10. Higher ERs (>30) were recorded for nerolidol, carvacrol, borneol, terpineol, limonene, menthone, pulegone, and menthol among the terpene-chemical penetration enhancers. @*Conclusion@#cLog P of terpene-based chemical permeation enhancers (CPE) is strongly correlated with ER of lipophilic drugs across human skin. Non-polar groups in terpenes and hydrogen bond interactions by terpenes with SC lipid enhance cutaneous drug penetration of lipophilic drugs.

Five new terpenoids from Viburnum odoratissimum var. sessiliflorum / 中国天然药物

Five new terpenoids, including two vibsane-type diterpenoids (1, 2) and three iridoid allosides (3-5), together with eight known ones, were isolated from the leaves and twigs of Viburnum odoratissimum var.sessiliflorum. Their planar structures and relative configurations were determined by spectroscopic methods, especially 2D NMR techniques. The sugar moieties of the iridoids were confirmed as β-D-allose by GC analysis after acid hydrolysis and acetylation. The absolute configurations of neovibsanin Q (1) and dehydrovibsanol B (2) were determined by quantum chemical calculation of their theoretical electronic circular dichroism (ECD) spectra and Rh2(OCOCF3)4-induced ECD analysis. The anti-inflammatory activities of compounds 1, 3, 4, and 5 were evaluated using an LPS-induced RAW264.7 cell model. Compounds 3suppressed the release of NO in a dose-dependent manner, with an IC50 value of 55.64 μmol·L-1. The cytotoxicities of compounds 1-5 on HCT-116 cells were assessed and the results showed that compounds 2 and 3 exhibited moderate inhibitory activities with IC50 values of 13.8 and 12.3 μmol·L-1, respectively.

Effect of acupuncture and moxibustion on intestinal flora in the rats with diarrhea-predominant irritable bowel syndrome based on 16S rDNA technique / 中国针灸

OBJECTIVES@#To explore the effect of acupuncture and moxibustion on intestinal flora in the rats with diarrhea-predominant irritable bowel syndrome (IBS-D) based on 16S rDNA technique.@*METHODS@#Ten rats were randomized from 58 SPF-grade male SD rats to be the blank group. The remained 48 rats were prepared to be IBS-D models by the modified method of acetic acid enema combined with binding tail-clip stress. Forty successfully-modeled rats were randomly divided into a model group, an acupuncture group, a moxibustion group and a western medication group, with 10 rats in each one. In the acupuncture group, the needle was inserted at bilateral "Zusanli" (ST 36) and remained for 15 min in each rat. In the moxibustion group, the suspending moxibustion was delivered at bilateral "Zusanli" (ST 36) for 15 min. The rats in the western medication group were given pinaverium bromide suspension (10 mL/kg) by intragastric administration. The above interventions were performed once daily for consecutive 14 days. The body mass and the score of fecal trait were compared before and after modeling, as well as after intervention in each group. Fecal water content, diarrhea index and colon transit time (CTT) were measured after modeling and intervention in the rats of each group separately. After intervention, the colonic morphology of rats in each group was observed, and using 16S rDNA technique, the intestinal flora was detected.@*RESULTS@#After modeling, compared with the blank group, the body mass and CTT were reduced (P<0.01); fecal trait scores, fecal water contents and diarrhea index increased (P<0.01) in the other 4 groups. After intervention, the body mass and CTT of the rats decreased (P<0.01), and fecal trait score, fecal water content and diarrhea index increased (P<0.01) in the model group compared with those in the blank group. In the acupuncture group, the moxibustion group and the western medication group, when compared with the model group, the body mass and CTT were elevated (P<0.01), while fecal trait scores, fecal water contents and diarrhea index declined (P<0.01). Compared with the western medication group, fecal water content decreased in the acupuncture group and the moxibustion group (P<0.05), while CTT increased in the acupuncture group (P<0.01), the body mass increased and fecal trait score was dropped in the moxibustion group (P<0.05). The colonic mucosa structure was clear and complete, and there was no obvious inflammatory cell infiltration in the blank group. The mild interstitial edema of intestinal mucosa was presented with the infiltration of few inflammatory cells in the model group. There was the infiltration of few inflammatory cells in the mucosa of the acupuncture group, the moxibustion group and the western medication group. Compared with the blank group, the indexes of Richness, Chao1, ACE and Shannon decreased in the model group (P<0.05). Indexes of Richness, Chao1 and ACE increased in the acupuncture group and the moxibustion group (P<0.05), and the Richness index in the western medication group increased (P<0.05) when compared with those in the model group. The relative abundance of Bacteroidetes, Proteobacteria and Prevotella increased (P<0.05), and that of Firmicutes and Muribaculaceae decreased (P<0.05) in the model group compared with those in the blank group. When compared with the model group, the relative abundance of Bacteroidetes, Proteobacteria and Prevotella was reduced (P<0.05), while that of Firmicutes and Muribaculaceae increased (P<0.05) in the acupuncture group, the moxibustion group and the western medication group; and that of Actinobacteria and Bifidobacterium increased in the acupuncture group and the moxibustion group (P<0.05). Compared with the blank group, the relative abundance of lipopolysaccharide (LPS) biosynthesis was elevated (P<0.05), and that of folate biosynthesis, lipoic acid metabolism, zeatin biosynthesis, ubiquinone and other terpenoid quinone biosynthesis decreased (P<0.05) in the model group. The relative abundance of LPS biosynthesis was dropped (P<0.05), and that of folate biosynthesis, lipoic acid metabolism, zeatin biosynthesis, ubiquinone and other terpenoid quinone biosynthesis increased (P<0.05) in the acupuncture group, the moxibustion group and the western medication group compared with those of the model group.@*CONCLUSIONS@#Either acupuncture or moxibustion can relieve the symptoms of IBS-D and protect intestinal mucosa, which may be associated with regulating the structure of intestinal flora and promoting nutrient metabolism and biosynthesis.

Research progress on chemical constituents and pharmacological activities of Viola plants / 中国中药杂志

There are 500 species of Viola(Violaceae) worldwide, among which 111 species are widely distributed in China and have a long medicinal history and wide varieties. According to the authors' statistics, a total of 410 compounds have been isolated and identified from plants of this genus, including flavonoids, terpenoids, phenylpropanoids, organic acids, nitrogenous compounds, sterols, saccharides and their derivatives, volatile oils and cyclotides. The medicinal materials from these plants boast anti-microbial, anti-viral, anti-oxidant and anti-tumor activities. This study systematically reviewed the chemical constituents and pharmacological activities of Viola plants to provide a basis for further research and clinical application.

Eleven new sesquiterpenoids from peeled stems of Syringa pinnatifolia / 中国中药杂志

The peeled stems of Syringa pinnatifolia(SP) is a representative Mongolian folk medicine with the effects of anti-depression, heat clearance, pain relief, and respiration improvement. It has been clinically used for the treatment of coronary heart disease, insomnia, asthma, and other cardiopulmonary diseases. As part of the systematic study on pharmacological substances of SP, 11 new sesquiterpenoids were isolated from the terpene-containing fractions of the ethanol extract of SP by liquid chromatography-mass spectrometry(LC-MS) and proton nuclear magnetic resonance(~1H-NMR) guided isolation methods. The planar structures of the sesquiterpenoids were identified by MS, 1D NMR, and 2D NMR data analysis, and were named pinnatanoids C and D(1 and 2), and alashanoids T-ZI(3-11), respectively. The structure types of the sesquiterpenoids included pinnatane, humulane, seco-humulane, guaiane, carryophyllane, seco-erimolphane, isodaucane, and other types. However, limited to the low content of compounds, the existence of multiple chiral centers, the flexibility of the structure, or lack of ultraviolet absorption, the stereoscopic configuration remained unresolved. The discovery of various sesquiterpenoids enriches the understanding of the chemical composition of the genus and species and provides references for further analysis of pharmacological substances of SP.

Comparison of catalytic functions and expression patterns of two pinene synthases from Wurfbainia villosa / 中国中药杂志

Wurfbainia villosa fruit is rich in volatile terpenoids, among which pinene is one of the main components and has anti-inflammatory, antibacterial, anti-tumor, and other pharmacological activities. This research group found that W. villosa fruits were rich in α-pinene by GC-MS, and terpene synthase(WvTPS63, formerly known as AvTPS1) with β-pinene as the main product was cloned and identified, but α-pinene synthase had not been identified. In this study, based on the genome data of W. villosa, we screened and found WvTPS66 with highly similar sequences to WvTPS63, identified enzyme functions of WvTPS66 in vitro, and performed a comparative analysis of sequence, catalytic function, expression pattern, and promoter with WvTPS63. Multiple sequence alignment showed that the amino acid sequences of WvTPS63 and WvTPS66 were highly similar and the conservative motif of terpene synthase was almost identical. In vitro enzymatic experiments on catalytic functions showed that both could produce pinene, and the main product of WvTPS63 was β-pinene, while that of WvTPS66 was α-pinene. Expression pattern analysis showed that WvTS63 was highly expressed in flowers, WvTPS66 was expressed in the whole plant, and the highest expression level was found in the pericarp, which indicated that it might be mainly responsible for the synthesis of α-pinene in fruits. In addition, promoter analysis revealed the presence of multiple regulatory elements related to stress response in the promoter regions of both genes. The findings of this study can provide a reference for the functional study of terpene synthase genes and new genetic elements for pinene biosynthesis.

Research progress of occupational hazards in plywood manufacturing / 中华劳动卫生职业病杂志

Occupational disease hazards in plywood manufacturing mainly include wood dust, formaldehyde, phenol, ammonia, noise, terpene, microorganisms, etc. The exposure is complex with multiple factors accompanied or coexisted. In the production process, these factors are exceeded, and mass occupational disease hazard events occurred among workers. Exposure to wood dust, formaldehyde, terpene, etc., put workers at increased risk of cancer. This article provides a review of this issue in order to provide a scientific basis for the prevention and control of occupational disease hazards in plywood manufacturing.

Identification and analysis of terpene synthase (TPS) gene family in Schizonepeta tenuifolia / 中国中药杂志

Terpenoids are important secondary metabolites of plants that possess both pharmacological activity and economic value. Terpene synthases(TPSs) are key enzymes in the synthesis process of terpenoids. In order to investigate the TPS gene family members and their potential functions in Schizonepeta tenuifolia, this study conducted a systematic analysis of the TPS gene family of S. tenuifolia based on the whole genome data of S. tenuifolia using bioinformatics methods. The results revealed 57 StTPS members identified from the genome database of S. tenuifolia. The StTPS family members encoded 285-819 amino acids, with protein molecular weights ranging from 32.75 to 94.11 kDa, all of which were hydrophilic proteins. The StTPS family members were mainly distributed in the cytoplasm and chloroplasts, exhibiting a random and uneven physical localization pattern. Phylogenetic analysis showed that the StTPS genes family were divided into six subgroups, mainly belonging to the TPS-a and TPS-b subfamilies. Promoter analysis predicted that the TPS gene family members could respond to various stressors such as light, abscisic acid, and methyl jasmonate(MeJA). Transcriptome data analysis revealed that most of the TPS genes were expressed in the roots of S. tenuifolia, and qRT-PCR analysis was conducted on genes with high expression in leaves and low expression in roots. Through the analysis of the TPS gene family of S. tenuifolia, this study identified StTPS5, StTPS18, StTPS32, and StTPS45 as potential genes involved in sesquiterpene synthesis of S. tenuifolia. StTPS45 was cloned for the construction of an prokaryotic expression vector, providing a reference for further investigation of the function and role of the TPS gene family in sesquiterpene synthesis.

Genome-wide identification of bZIP family genes and screening of candidate AarbZIPs involved in terpenoid biosynthesis in Artemisia argyi / 中国中药杂志

Artemisia argyi is an important medicinal and economic plant in China, with the effects of warming channels, dispersing cold, and relieving pain, inflammation, and allergy. The essential oil of this plant is rich in volatile terpenoids and widely used in moxi-bustion and healthcare products, with huge market potential. The bZIP transcription factors compose a large family in plants and are involved in the regulation of plant growth and development, stress response, and biosynthesis of secondary metabolites such as terpenoids. However, little is known about the bZIPs and their roles in A. argyi. In this study, the bZIP transcription factors in the genome of A. argyi were systematically identified, and their physicochemical properties, phylogenetic relationship, conserved motifs, and promoter-binding elements were analyzed. Candidate AarbZIP genes involved in terpenoid biosynthesis were screened out. The results showed that a total of 156 AarbZIP transcription factors were identified at the genomic level, with the lengths of 99-618 aa, the molecular weights of 11.7-67.8 kDa, and the theoretical isoelectric points of 4.56-10.16. According to the classification of bZIPs in Arabidopsis thaliana, the 156 AarbZIPs were classified into 12 subfamilies, and the members in the same subfamily had similar conserved motifs. The cis-acting elements of promoters showed that AarbZIP genes were possibly involved in light and hormonal pathways. Five AarbZIP genes that may be involved in the regulation of terpenoid biosynthesis were screened out by homologous alignment and phylogenetic analysis. The qRT-PCR results showed that the expression levels of the five AarbZIP genes varied significantly in different tissues of A. argyi. Specifically, AarbZIP29 and AarbZIP55 were highly expressed in the leaves and AarbZIP81, AarbZIP130, and AarbZIP150 in the flower buds. This study lays a foundation for the functional study of bZIP genes and their regulatory roles in the terpenoid biosynthesis in A. argyi.

La Huamanripa (Senecio tephrosioides Turcz) como alternativa saludable para afecciones respiratorias durante la pandemia COVID-19 / Huamanripa (Senecio tephrosioides Turcz) as a healthy alternative for respiratory conditions during the COVID-19 pandemic / Huamanripa (Senecio tephrosioides Turcz) como alternativa saudável para problemas respiratórios durante a pandemia de COVID-19

Desde tiempo histórico las plantas medicinales se han empleado como ingrediente principal para preparación de diferentes recetas. Motivo que se investigó sobre la Huamanripa como alternativa saludable para afecciones respiratorias durante la pandemia COVID-19 en Barranca. Objetivo. El objetivo fue determinar la eficiencia de la Huamanripa como alternativa saludable para las afecciones respiratorias en la pandemia. Materiales y Método. La metodología se basa en investigación descriptiva con enfoque cuantitativo prospectivo, por lo que se cuestionó sobre la preparación, frecuencia de consumo y para que enfermedades se consumen. Obtenidos los datos se procesaron mediante estadísticas básicas y regresión. Resultados. Se determinó que la Huamanripa lo usan para tratamiento casero medicinal y consume con frecuencia 4 a 5 veces por semana para afecciones respiratorias y COVID-19, consumo de Huamanripa por mes con 23 % de la población, porcentaje de alivio de afecciones respiratorias con 84 %, correlación entre el consumo de Huamanripa y porcentaje de alivio r = 0.99 y en análisis de varianza del consumo de Huamanripa y el porcentaje de alivio no hubo significancia. Conclusiones. Concluye que la Huamanripa es una alternativa eficiente y se puede complementar con otros tratamientos para las afecciones respiratorias y síntomas de COVID-19; ya sea por sus propiedades como aceites especiales y terpenos que tienen efectos antimicrobiana, antiinflamatoria, aliviante, lo cual favorece a la salud.

Since historical times, medicinal plants have been used as the main ingredient for the preparation of different recipes. For this reason, Huamanripa was investigated as a healthy alternative for respiratory diseases during the COVID-19 pandemic in Barranca. Objective. The objective was to determine the efficiency of Huamanripa as a healthy alternative for respiratory diseases during the pandemic. Materials and Method. The methodology is based on descriptive research with a prospective quantitative approach, so that the preparation, frequency of consumption and the diseases for which it is consumed were questioned. Data were obtained and processed by means of basic statistics and regression. Results. It was determined that Huamanripa is used for medicinal home treatment and consumed 4 to 5 times a week for respiratory diseases and COVID-19, consumption of Huamanripa per month with 23% of the population, percentage of relief of respiratory diseases with 84%, correlation between consumption of Huamanripa and percentage of relief r = 0.99 and in variance analysis of Huamanripa consumption and percentage of relief there was no significance. Conclusions. It is concluded that Huamanripa is an efficient alternative and can be complemented with other treatments for respiratory conditions and symptoms of COVID-19; either by its properties such as special oils and terpenes that have antimicrobial, anti-inflammatory, relieving effects, which favors health.

Desde tempos históricos as plantas medicinais têm sido utilizadas como ingrediente principal para a preparação de diferentes receitas. Por esta razão, Huamanripa foi investigado como uma alternativa saudável para doenças respiratórias durante a pandemia da COVID-19 em Barranca. Objetivo. O objetivo era determinar a eficiência de Huamanripa como uma alternativa saudável para as doenças respiratórias durante a pandemia. Materiais e Método. A metodologia é baseada em pesquisa descritiva com uma abordagem quantitativa prospectiva, de modo que foram feitas perguntas sobre a preparação, a freqüência do consumo e para quais doenças é consumida. Os dados foram obtidos e processados utilizando estatísticas básicas e regressão. Resultados. Foi determinado que Huamanripa é usado para tratamento medicinal domiciliar e consumido 4 a 5 vezes por semana para doenças respiratórias e COVID-19, consumo de Huamanripa por mês com 23% da população, porcentagem de alívio de doenças respiratórias com 84%, correlação entre consumo de Huamanripa e porcentagem de alívio r = 0,99 e na análise de variância do consumo de Huamanripa e da porcentagem de alívio não houve significância. Conclusões. Conclui que Huamanripa é uma alternativa eficiente e pode ser complementada com outros tratamentos para condições respiratórias e sintomas da COVID-19; seja por suas propriedades como óleos especiais e terpenos que têm efeitos antimicrobianos, anti-inflamatórios, aliviadores, o que favorece a saúde.

Study of the interactions of di- and tri-terpenes from Stillingia loranthacea with the enzyme NSP16-NSP10 of SARS-CoV-2 / Estudo das interações de di- e tri-terpenos de Stillingia loranthacea com a enzima NSP16-NSP10 de SARS-CoV-2

Objective: This study aimed to evaluate the interactions of di- and tri-terpenes from Stillingia loranthacea with the enzyme NSP16-NSP10 of SARS-CoV-2, important for viral replication. Methods: The molecular docking technique was used to evaluate this interaction. Results: The analysis showed that the evaluated compounds obtained RMSD values of 0.888 to 1.944 Å and free energy of -6.1 to -9.4 kcal/mol, with the observation of hydrogen bonds, salt bridges, and pi-sulfur, pi-alkyl, and hydrophobic interactions. Conclusion: Thus, the results obtained show the potential of the compounds analyzed against the selected target. Since computer simulations are only an initial step in projects for the development of antiviral drugs, this study provides important data for future research.

Objetivo: avaliar as interações de di- e tri-terpenos de Stillingia loranthacea com a enzima NSP16-NSP10 de SARS-CoV-2, importante para a replicação viral. Métodos: A técnica de docking molecular foi utilizada para avaliar essa interação. Resultados: A análise mostrou que os compostos avaliados obtiveram valores de RMSD de 0,888 a 1,944 Å e energia livre de -6,1 a -9,4 kcal/mol, observando-se ligações de hidrogênio, pontes salinas e pi-enxofre, pi-alquil, e interações hidrofóbicas. Conclusão: Assim, os resultados obtidos mostram o potencial dos compostos analisados frente ao alvo selecionado. Como as simulações computacionais são apenas um passo inicial nos projetos de desenvolvimento de medicamentos antivirais, este estudo fornece dados importantes para pesquisas futuras.

Antibacterial and hemolytic activity of extracts and compounds obtained from epicarps and seeds of Garcinia madruno(Kunth) Hammel / Actividad antimicrobiana y hemolítica de extractos y compuestos obtenidos del epicarpio y las semillas de Garcinia madruno (Kunth) Hammel

This paper describes the evaluation of the antimicrobial and hemolytic activity of the hexane, dichloromethane, ethyl acetate and methanol extracts from seeds and epicarps of Garcinia madruno; as well garcinol, morelloflavone and volkensiflavone isolated from the same species. In the preliminary test of bacterial susceptibility, hexane extracts from seeds and epicarps and the three compounds tested only displayed inhibitory growth effect against Gram-positive bacteria. The minimum inhibitory concentrations of extract and compounds ranging from 86.6 to 1253.4 µg/mL. The hemolytic activity was assessed; however, except for the methanol extract from seeds, none of the samples studied induced hemolysis. Thus, our results suggest that extracts and compounds from G. madruno have the potential to be used in the control of pathologies associated to Gram-positive bacteria. This is the first report of the antimicrobial and hemolytic activity of extracts of different polarity obtained from seeds and epicarps of this edible species.

El presente artículo describe la evaluación de la actividad antimicrobiana y hemolítica de los extractos de hexano, diclorometano, acetato de etilo y metanol, obtenidos de la semilla y el epicarpio de Garcinia madruno; así como de garcinol, morelloflavona y volkensiflavona; aislados de la misma especie. En el ensayo de susceptibilidad bacteriana, tanto el extracto de hexano obtenido a partir de la semilla y el epicarpio, y los tres compuestos aislados, únicamente mostraron actividad inhibitoria del crecimiento contra bacterias Gram-positivas. La concentración mínima inhibitoria presentó valores entre 86.6 y 1253.4 µg/mL. También se estableció la actividad hemolítica; sin embargo, con excepción del extracto metanólico obtenido a partir de las semillas, ninguna de las muestras evaluadas indujo hemólisis. Por lo tanto, los resultados sugieren que los extractos y compuestos de G. madruno tienen el potencial de ser usados en el control de bacterias Gram-positivas asociadas a diversas patologías. Este es el primer reporte de actividad antimicrobiana y hemolítica de extractos de diferente polaridad obtenidos de las semillas y epicarpios de esta especie comestible.

Estudio comparativo de la actividad anti-fúngica de extractos secuenciales de Fuchsia lycioides contra Candida sp / comparative study of the antifungal activity of sequencial extracts of Fuchsia lycioides against Candida sp

The genus Fuchsia is generally used in herbal preparations to treat conditions caused by microorganisms. Based on the popular use of this type of plants, the objective of this study was to obtain sequential extracts of increasing polarity from the branches of Fuchsia lycioides by maceration at room temperature and by the Soxhlet method at 60ºC, to later evaluate the antifungal capacity of the extracts against different clinical isolates of the Candida genus. The ethyl acetate extract exhibited strong anti-fungal activity, selectively inhibiting C. albicans strains with MIC and CMF values of 10 and 15 µg/mL, respectively; comparable with the drug itraconazole®. The analysis of the extract by GC-MS showed a high concentration of terpenoids (mainly phytol) and phenylpropanoids (mainly cinnamic acid), possibly responsible for the antifungal activity of the ethyl acetate extract of F. lycioides.

El género Fuchsia se usa generalmente en preparaciones de hierbas para tratar afecciones provocadas por microorganismos. En base al uso popular de este tipo de plantas, el objetivo de este estudio fue obtener los extractos secuenciales de polaridad creciente de las ramas de Fuchsia lycioides por maceración a temperatura ambiente y por el método Soxhlet a 60ºC, para luego evaluar la capacidad antifúngica de los extractos frente a diferentes aislados clínicos del genero Candida. El extracto de acetato de etilo exhibió una fuerte actividad antifúngica inhibiendo en forma selectiva las cepas de C. albicans con valores de CMI y de CMF de 10 y 15 µg/mL, respectivamente; comparables con el fármaco itraconazol®. El análisis del extracto por CG-EM mostró una alta concentración de terpenoides (principalmente fitol) y fenilpropanoides (principalmente ácido cinámico), posibles responsables de la actividad antifúngica del extracto de acetato de etilo de F. lycioides.

Plant Pharmacophylogeny: Review and Future Directions / 中国结合医学杂志

Medicinal plants have provided numerous medicinal active ingredients for thousands of years and these ingredients have been used in Chinese medicine (CM) and traditional pharmacologies worldwide. Recently, the exploitation and utilisation of medicinal plant resources has increased significantly. The results of the studies have led to the identification of many active components, such as steroidal alkaloids, saponins, terpenoids, and glycosides, in various medicinal plants with different evolutionary levels. Moreover, research on the chemical classification, molecular phylogeny, and pharmacological activity of medicinal plants is increasing in popularity. Pharmacophylogeny is an interdisciplinary topic that studies the correlation between plant phylogeny, chemical composition, and curative effects (pharmacological activity and the traditional curative effect) of medicinal plants. In addition, it provides the basic tools to enable research and development of CM resources. This literature review, based on the genetic relationship between phytogroup and species, highlights the formation process, research content, applications, and future directions of pharmacophylogeny.

Research progress of Curcuma kwangsiensis root tubers and analysis of liver protection and anti-tumor mechanisms based on Q-markers / 中国中药杂志

Curcuma kwangsiensis root tuber is a widely used genuine medicinal material in Guangxi, with the main active components of terpenoids and curcumins. It has the effects of promoting blood circulation to relieve pain, moving Qi to relieve depression, clearing heart and cooling blood, promoting gallbladder function and anti-icterus. Modern research has proved its functions in liver protection, anti-tumor, anti-oxidation, blood lipid reduction and immunosuppression. Considering the research progress of C. kwangsiensis root tubers and the core concept of quality marker(Q-marker), we predicted the Q-markers of C. kwangsiensis root tubers from plant phylogeny, chemical component specificity, traditional pharmacodynamic properties, new pharmacodynamic uses, chemical component measurability, processing methods, compatibility, and components migrating to blood. Curcumin, curcumol, curcumadiol, curcumenol, curdione, germacrone, and β-elemene may be the possible Q-markers. Based on the predicted Q-markers, the mechanisms of the liver-protecting and anti-tumor activities of C. kwangsiensis root tubers were analyzed. AKT1, IL6, EGFR, and STAT3 were identified as the key targets, and neuroactive ligand-receptor interaction signaling pathway, nitrogen metabolism pathway, cancer pathway, and hepatitis B pathway were the major involved pathways. This review provides a basis for the quality evaluation and product development of C. kwangsiensis root tubers and gives insights into the research on Chinese medicinal materials.

Microbial synthesis of monoterpenoids: a review / 生物工程学报

Monoterpenoids that belong to the terpenoids family are usually volatile and have strong aroma. Some monoterpenoids also have antioxidant, antibacterial and anti-inflammatory activities, which make them important raw materials for medicine, food and cosmetics industry. In recent years, the heterologous synthesis of monoterpenoids by microorganisms has attracted extensive attention. However, its large-scale application is greatly hampered by the low yield and high production cost. Nowadays, the rapid development of synthetic biology provides new approaches for enhancing the production of monoterpenoids by microorganisms. Different kinds of recombinant strains can be obtained via engineering of microbial cells to produce a variety of monoterpenoids with different properties. This paper summarized the latest strategies and progress in the application of synthetic biology to produce monoterpenoids by microorganisms, including the design and modification of biosynthetic pathway, as well as the design and optimization of high-yield monoterpenoids producing chassis cells.

Phytotoxicity of plant extracts of Vismia japurensis cultivated in vivo and in vitro / Fitotoxicidade de extratos de plantas de Vismia japurensis cultivadas in vivo e in vitro

Plants that produce secondary metabolites with allelopathic activity or phytotoxicity can be biotechnologically important, serving as sources of allelochemicals, and thus contributing to the agroindustrial sector. Vismia japurensis (Hypericaceae) is an Amazonian species that grows in clumps called vismiais, from which most other plants are absent. Accordingly, the objective of this study was to identify possible phytotoxicity effects of hexane and methanol extracts of Vismia japurensis leaves and branches in vivo and from seedlings grown in vitro on Lactuca sativa. In addition, fresh and dry leaves were assayed by the sandwich method in order to determine their ability to release allelochemicals. The hexanic extract from in vitro seedlings reduced germination by 10%, while the methanol extract produced a 16% reduction in germination speed. Root growth of Lactuca sativa was inhibited by 64.7% when subjected to hexane leaf extract, by 39.3% under the influence of hexane branch extract, and by 96.09% for in vitro seedling hexanic extract. When analysed by thin layer chromatography and 1H nuclear magnetic resonance, extracts showed evidence of terpenes, anthraquinones and flavonoids, with greater intensity of signals in the aromatic region of in vitro seedling hexanic extract. Clearly, Vismia japurensis has a high biotechnological potential in terms of the production of substances of low polarity with capacity to interfere in plant development.

Plantas que produzem metabólitos secundários com atividade alelopática ou fitotóxica podem ser biotecnologicamente importantes, servindo como fontes de aleloquímicos e, assim, contribuindo para o setor agroindustrial. Vismia japurensis (Hypericaceae) é uma espécie amazônica que cresce em grupos, formando vismiais. Assim, o objetivo deste estudo foi identificar possíveis efeitos fitotóxicos de extratos hexânicos e metanólicos de folhas e ramos de Vismia japurensis in vivo e de plântulas cultivadas in vitro sobre Lactuca sativa. Além disso, folhas frescas e secas foram analisadas pelo método sanduíche, a fim de determinar sua capacidade de liberação de aleloquímicos. O extrato hexânico de plântulas in vitro reduziu a germinação em 10% e o extrato metanólico promoveu uma redução de 16% na velocidade de germinação. O crescimento radicular de Lactuca sativa foi inibido em 64,7% quando submetido ao extrato hexânico das folhas, em 39,3% sob influência do extrato hexânico dos galhos e em 96,09% para o extrato de hexânico das plântulas in vitro. Quando analisados por cromatografia em camada delgada e ressonância magnética nuclear de 1H, os extratos mostraram evidências de terpenos, antraquinonas e flavonoides, com maior intensidade de sinais na região aromática do extrato hexânico das plântulas in vitro. Assim, Vismia japurensis possui elevado potencial biotecnológico em termos de produção de substâncias de baixa polaridade com capacidade de interferência no desenvolvimento de plantas.

A novel approach to Cestrum intermedium (mata-boi): anatomical and physical-chemical characterization, in vitro biological activities, and metabolites of a Brazilian native species

Abstract The Brazilian native species Cestrum intermedium, known as mata-boi, induces hepatotoxicity and death when ingested by cattle. While most studies on this species focus on toxicological features, our study is the first to describe the anatomy and in vitro biological activities of Cestrum intermedium. We investigated adult leaves and stems by histochemistry, described their anatomy, performed physical-chemical analysis, determined in vitro antioxidant and antimicrobial activities, and identified secondary metabolites. A few noteworthy anatomical features were the anomocytic stomata on the abaxial surface and the absence of trichomes, in addition to the circular shaped petiole with two projections on the adaxial surface. Histochemical analysis showed chemical markers such as alkaloids, usually reported as toxic, and terpenoids. Potassium nitrate (ATR-FTIR) and lupeol palmitate (NMR) were detected on the crude stem extract. Thermogravimetric and physical-chemical analysis provided fingerprint parameters for the species. Minimal Inhibitory Concentration (MIC) assay revealed that Staphylococcus aureus, Staphylococcus epidermidis, and Candida albicans were weakly inhibited by extract samples. Chloroform and ethyl acetate fractions presented high phenolic content, which resulted in in vitro antioxidant activity. These novel features expand the knowledge about this species, considering that previous studies mainly focused on its toxicity. Our study also provided characteristics that may help in avoiding misidentification between Cestrum members, especially when taxonomic keys cannot be employed, as in the absence of flowers and fruits.

Evaluation of copaiba oil as enhancer of ibuprofen skin permeation

Abstract The administration of medications on the skin through transcutaneous routes is a practice that has been used by mankind for millennia. Some studies have been reporting the use of terpenes and natural oils rich in terpenes as an enhancer of cutaneous penetration. Copaiba oil, due to its rich content of terpenes, presents itself as a great choice of penetration enhancer for drugs administered on the skin. In this study, we developed two cream formulations containing 5% of ibuprofen (IBU) and copaiba oil: IBCO5 and IBCO10 with 5% and 10% of copaiba oil respectively. Ex vivo cutaneous penetration/permeation studies of IBU were performed using pig ear skin as biological membrane in the Franz-type diffusion cells. The steady-state flux of IBU samples, IBCO5 (35.72 ± 6.35) and IBCO10 (29.78 ± 2.41) were significantly higher when compared with control without copaiba oil (10.32 ±1.52) and with a commercial product (14.44 ± 2.39). In the penetration analysis, the amount of IBU found in the samples IBCO5 and IBCO10 was markedly higher in the dermis than epidermis. Our results showed that copaiba oil possesses attracting properties in promoting skin penetration and permeation of IBU when added into cream formulations.

Actividad antibacteriana del extracto etanólico de Plantago major frente a Streptococcus mutans / Antibacterial activity of Plantago major ethanolic extract against Streptococcus mutans

Introducción: Las propiedades antibacterianas de Plantago major frente a microorganismos orales no se ha estudiado ampliamente. Objetivo: Identificar los metabolitos secundarios presentes en el extracto etanólico de Plantago major y determinar su actividad antibacteriana frente a Streptococcus mutans. Métodos: Se prepararon concentraciones del 25 por ciento, 50 por ciento, 75 por ciento y 100 por ciento de extracto etanólico (EE) de Plantago major. Se cargaron seis discos de papel con 10 µL, 15 µL, 20 µL y 25 µL de cada concentración, haciendo un total de 96 discos. Los discos fueron colocados en placas Petri con agar cerebro-corazón inoculadas con Streptococcus mutans, se empleó clorhexidina al 0,12 por ciento como control positivo. Se calcularon seis repeticiones para cada concentración. Las placas fueron incubadas a 37 °C por 48 horas. La medición de los halos de inhibición se realizó con un compás digital. El análisis estadístico se realizó mediante la prueba ANOVA de un factor seguido por la prueba post hoc de Tukey. Resultados: El análisis químico del extracto etanólico de Plantago major identificó la presencia de terpenos, diterpenos, saponinas, terpenoidales y aceites esenciales. Las concentraciones del 25 por ciento y 50 por ciento no mostraron efecto antibacteriano, los volúmenes mayores de 20 µL de la concentración del 75 por ciento y todas los del 100 por ciento fueron efectivos para inhibir el crecimiento de Streptococcus mutans con halos de inhibición de 8,36 mm a 14,64 mm. La clorhexidina al 0,12 por ciento inhibió el crecimiento de Streptococcus mutans con halos de inhibición de 17,77 mm en promedio, presentando diferencias significativas con todas las concentraciones del extracto etanólico de Plantago major (P < 0,05). Conclusiones: El extracto etanólico de Plantago major presentó derivados de los terpenos y saponinas, y mostró actividad antibacteriana frente a Streptococcus mutans en volúmenes y concentraciones mayores a 20 µL/75 por ciento(AU)

Introduction: The antibacterial properties of Plantago major against oral microorganisms have not been widely studied. Objective: Identify the secondary metabolites present in an ethanolic extract of Plantago major and determine their antibacterial activity against Streptococcus mutans. Methods: The Plantago major ethanolic extract (EE) was prepared at concentrations of 25 percent, 50 percent, 75 percent and 100 percent. Six paper discs were loaded with 10 µl, 15 µl, 20 µl and 25 µl of each concentration, for a total 96 discs, which were then placed on Petri plates with brain heart agar inoculated with Streptococcus mutans. The positive control was 0.12 percent chlorhexidine. Six replicates were estimated for each concentration. The plates were incubated at 37ºC for 48 hours. Inhibition haloes were measured with a digital caliper. Statistical analysis was based on one-factor ANOVA testing followed by Tukey's post hoc test. Results: Chemical analysis of the Plantago major ethanolic extract identified the presence of terpenes, diterpenes, saponins, terpenoids and essential oils. The 25 percent and 50 percent concentrations did not display an antibacterial effect, whereas volumes above 20 µl of the 75 percent concentration and all 100 percent volumes were effective to inhibit Streptococcus mutans growth with inhibition haloes of 8.36 mm to 14.64 mm. 0.12 percent chlorhexidine inhibited Streptococcus mutans with inhibition haloes of 17.77 mm on average, presenting significant differences with all the concentrations of the Plantago major ethanolic extract (p < 0.05). Conclusions: The Plantago major ethanolic extract was found to contain terpene and saponin derivatives, and displayed antibacterial activity against Streptococcus mutans at volumes and concentrations above 20 µl / 75 percent(AU)