Potential of Tetradenia riparia leaf essential oil and its fractions in controlling Aedes aegypti and Rhipicephalus microplus larvae

Tetradenia riparia (Hochst.) Codd (Lamiaceae) is a shrub, commonly known as ginger bush or false myrrh, and several studies have shown that T. riparia exhibits a variety of biological properties. This study aimed to determine the chemical composition of T. riparia essential oil and its fractions, investigate their anticholinesterase activity, and assess their larvicidal activity against the cattle tick Rhipicephalus microplus and the mosquito Aedes aegypti. Eleven essential oil fractions were obtained by fractionation and analyzed by gas chromatography/mass spectrometry. Larvicidal activity against R. microplus and third-instar A. aegypti was assessed using a larval packet test and a larval immersion test, respectively. Anticholinesterase activity was determined by a bioautographic method. Forty-nine compounds were identified in the essential oil, of which the major classes were oxygenated sesquiterpenes (45.95%) and sesquiterpene hydrocarbons (35.20%) and the major components were isospathulenol (17.40%), ß-caryophyllene (15.61%), 14-hydroxy-9-epi-caryophyllene (10.07%), 14-hydroxy-α-muurolene (8.32%), and 9ß,13ß-epoxy-7-abietene (5.53%). Bioassays showed that T. riparia essential oil (LC50 = 1.56 µg/mL) and FR3 (LC50 = 0.30 µg/mL) were the most active against R. microplus and A. aegypti larvae, respectively. The essential oil and FR1, FR2, and FR3 exhibited acetylcholinesterase inhibitory activity. These results indicate that T. riparia essential oil and its fractions hold promise in the development of novel, environmentally safe agents for the control of R. microplus and A. aegypti larvae.

Estudo do potencial antiviral sobre o Sars-Cov-2 dos compostos identificados no extrato bruto das folhas de Tetradenia riparia / Study of antiviral potential on Sars-Cov-2 of compounds identified in Tetradenia riparia leaves crude extract / Estudio del potencial antiviral sobre el Sars-Cov-2 de los componentes identificados en el extracto crudo de las hojas de Tetradenia riparia

A COVID-19 surgiu de forma repentina, acometendo milhões de pessoas e causando muitas mortes no mundo todo. Diante disso, torna-se necessário a busca de substâncias bioativas com propriedades antivirais. No Brasil, a espécie Tetradenia riparia foi inserida como planta ornamental exótica, com aroma intenso e agradável, sendo cultivada em parques, jardins, residenciais e hortos. O objetivo deste estudo foi identificar compostos presentes no extrato bruto das folhas de Tetradenia riparia com interesse antiviral. O extrato bruto das folhas secas foi obtido por maceração dinâmica por esgotamento do solvente e após, concentrado em evaporador rotativo. A composição química do extrato bruto foi analisada por cromatografia líquida de ultra eficiência acoplada à espectrometria de massas de alta resolução (UHPLC-ESI/qTOF). Foram identificados 31 compostos que foram investigados por meio de levantamento bibliográfico quanto ao seu potencial anti- SARS-CoV-2. Os compostos rosmanol, procianidina, cianidina, betulina, ácido betulínico e o ácido sagerínico, apresentaram potencial atividade antiviral sobre o SARS-CoV-2. Esta investigação é promissora, indicando possivelmente que no extrato bruto das folhas de T. ripária existem compostos que podem combater o SARS-CoV-2. Neste sentido, estudos de ancoramento molecular (docking) e análises in silico sobre a proteína Mpro do vírus devem ser realizadas corroborando desta forma a ação dos compostos identificados.

COVID-19 appeared suddenly, affecting millions of people and causing many deaths worldwide. Therefore, it is necessary to search for bioactive substances with antiviral properties. In Brazil, Tetradenia riparia was inserted as an exotic ornamental plant, with an intense and pleasant aroma, cultivated in parks, residential and vegetable gardens. This study aimed to identify compounds present in the crude extract of Tetradenia riparia leaves with antiviral interest. The crude extract of the dried leaves was obtained by dynamic maceration with solvent exhaustion and then concentrated in a rotary evaporator. The chemical composition of the crude extract was analyzed by ultra- performance liquid chromatography coupled with high-resolution mass spectrometry (UHPLC- ESI/qTOF). We identified 31 compounds investigated through a literature review for their anti- SARS-CoV-2 potential. The compounds rosmanol, procyanidin, cyanidin, betulin, betulinic acid, and sagerinic acid showed potential antiviral activity against SARS-CoV-2. Therefore, this investigation is promising, possibly indicating that in the crude extract of T. riparia leaves, there are compounds that can fight SARS-CoV-2. In this sense, molecular docking studies and in silico analyzes on the virus Mpro protein must be carried out, thus corroborating the action of the identified compounds.

SARS-CoV-19 ha aparecido repentinamente, afectando a millones de personas y causando muchas muertes en todo el mundo. Por ello, se hace necesaria la búsqueda de sustancias bioactivas con propiedades antivirales. En Brasil, la especie Tetradenia riparia ha sido introducida como planta ornamental exótica, con un aroma intenso y agradable, siendo cultivada en parques, jardines, residencias y centros de jardinería. El objetivo de este estudio fue identificar los compuestos presentes en el extracto crudo de las hojas de Tetradenia riparia con interés antiviral. El extracto crudo de las hojas secas se obtuvo por maceración dinámica por agotamiento del disolvente y después, se concentró en el evaporador rotatorio. La composición química del extracto crudo se analizó mediante cromatografía líquida de ultra rendimiento acoplada a espectrometría de masas de alto rendimiento (UHPLC-ESI/qTOF). Se identificaron 31 compuestos y se investigó su potencial anti-SARS-CoV-2 mediante un estudio bibliográfico. Los compuestos rosmanol, procianidina, cianidina, betulina, ácido betulínico y ácido sagerínico, mostraron una potencial actividad antiviral sobre el SARS-CoV-2. Esta investigación es prometedora, pues posiblemente indica que en el extracto crudo de las hojas de T. riparia hay compuestos que pueden combatir el SARS-CoV-2. En este sentido, deben realizarse estudios de docking y análisis in silico sobre la proteína Mpro del virus para corroborar la acción de los compuestos identificados.

Mechanism of “ruxiang-moyao” herbal pair in the treatment of knee osteoarthritis based on network pharmacology / 中国组织工程研究

BACKGROUND: “Ruxiang-Moyao” is a common combination of traditional Chinese medicine in the clinical treatment of knee osteoarthritis. However, the pharmacological mechanism is not yet clear. OBJECTIVE: Using network pharmacology technology to explore the therapeutic target of “Ruxiang-Moyao” as a commonly used traditional Chinese medicine for clinical treatment of arthromyodynia in the treatment of knee osteoarthritis and the relevant mechanism. METHODS: The chemical constituents of “Ruxiang-Moyao” were collected by TCMSP pharmacology database and analysis platform, and the possible bioactive constituents of frankincense and myrrh were screened according to the biological oral availability ≥ 30% and class drug properties ≥ 0.18. The possible targets of each active constituent were screened out using the protein database (Uniprot). GeneCards, OMIM, TTD and DrugBank databases were consulted to mine knee osteoarthritis-associated gene targets. The disease-drug protein target genes were obtained after the intersection of the above-mentioned screening data. The STRING database calculation and analysis algorithm was used to screen out important key genes to build a protein-protein interaction network, and the key target genes were uploaded to the PPI network graph. Cytoscape software was used to map the drug-target and disease-target visualization network, and DAVID online tool was further used for gene ontology (GO) analysis and Kyoto Encyclopedia of Genes and Gnomes (KEGG) pathway enrichment analysis. RESULTS AND CONCLUSION: Eight bioactive constituents of frankincense and 45 bioactive constituents of myrrh were obtained. At the same time, 412 target proteins of “Ruxiang-Moyao,” 1889 genes related to knee osteoarthritis and 105 co-targets of drugs and diseases were detected. The protein-protein interaction network found that AKT1, TP53, IL6, TNF, JUN, and MAPK1 might be the key targets of “Ruxiang-Moyao” in the treatment of knee osteoarthritis. The GO enrichment analysis identified 66 GO items, which are involved in cell response to hypoxia, negative regulation of epithelial cell proliferation, immune response, insulin-stimulated cell response, and positive regulation of fibroblast proliferation. The enrichment analysis of KEGG pathway identified 95 related signaling pathways, which are involved in inflammation, cell apoptosis and cell senescence. David enrichment analysis showed that the key target of “Ruxiang-Moyao” intervention for knee osteoarthritis was mainly related to several biological processes such as inflammatory response, cell apoptosis and immune system. Overall, “Ruxiang-Moyao” has the characteristics of multi-pathway and multi-target action in the treatment of knee osteoarthritis, and mainly has anti-inflammatory and analgesic effects. The key targets of its action and the involved biological process and signaling pathway have been preliminarily revealed, providing a new idea for the clinical prescription treatment of knee osteoarthritis in the future.

Effects of Frankincense and Myrrh essential oil on transdermal absorption of ferulic acid in Chuanxiong / 中国中药杂志

The aim of this paper was to explore the effects of Frankincense and Myrrh essential oil on transdermal absorption, and investigate the mechanism of permeation on the microstructure and molecular structure of stratum corneum. Through the determination of stratum corneum/medium partition coefficient of ferulicacid in Chuanxiong influenced by Frankincense and Myrrh essential oil, the effects of volatile oil of frankincense and Myrrh on the the microscopic and molecular structure of stratum corneum were explored by observation of skin stratum corneum structure under scanning electron microscopy, and investigation of frankincense and myrrh essential oil effects on the molecular structure of keratin and lipids in stratum corneum under Fourier transform infrared spectroscopy. The results showed that the oil could enhance the distribution of ferulic acid in the stratum corneum and medium, and to a certain extent damaged the imbricate structure of stratum corneum which was originally regularly, neatly, and closely arranged; some epidermal scales turned upward, with local peeling phenomenon. In addition, frankincense and myrrh essential oil caused the relative displacement of CH2 stretching vibration peak of stratum corneum lipids and amide stretching vibration peak of stratum corneum keratin, indicating that frankincense and myrrh essential oil may change the conformation of lipid and keratin in the stratum corneum, increase the bilayer liquidity of the stratum corneum lipid, and change the orderly and compact structure to increase the skin permeability and reduce the effect of barrier function. It can be concluded that Frankincense and Myrrh essential oil can promote the permeation effect by increasing the distribution of drugs in the stratum corneum and changing the structure of the stratum corneum.

Effects of Frankincense and Myrrh essential oil on transdermal absorption in vitro of Chuanxiong and penetration mechanism of skin blood flow / 中国中药杂志

The aim of this paper was to explore the effects of Frankincense and Myrrh essential oil on transdermal absorption in vitro of Chuanxiong, and to investigate the possible penetration mechanism of their essential oil from the perspective of skin blood perfusion changes. Transdermal tests were performed in vitro with excised mice skin by improved Franz diffusion cells. The cumulative penetration amounts of ferulic acid in Chuanxiong were determined by HPLC to investigate the effects of Frankincense and Myrrh essential oil on transdermal permeation properties of Chuanxiong. Simultaneously, the skin blood flows were determined by laser flow doppler. The results showed that the cumulative penetration amount of ferulic acid in Chuanxiong was (8.13±0.76) μg•cm⁻² in 24 h, and was (48.91±4.87), (57.80±2.86), (63.34±4.56), (54.17±4.40), (62.52±7.79) μg•cm⁻² respectively in Azone group, Frankincense essential oil group, Myrrh essential oil, frankincense and myrrh singly extracted essential oil mixture group, and frankincense and myrrh mixed extraction essential oil group. The enhancement ratios of each essential oil groups were 7.68, 8.26, 7.26, 8.28, which were slightly greater than 6.55 in Azone group. In addition, as compared with the conditions before treatment, there were significant differences and obvious increasing trend in blood flow of rats in Frankincense essential oil group, Myrrh essential oil group, frankincense and myrrh singly extracted essential oil mixture group, and frankincense and myrrh mixed extraction essential oil group when were dosed at 10, 20, 30, 10 min respectively, indicating that the skin blood flows were increased under the effects of Frankincense and Myrrh essential oil to a certain extent. Thus, Frankincense and Myrrh essential oil had certain effect on promoting permeability of Chuanxiong both before and after drug combination, and may promote the elimination of drugs from epidermis to dermal capillaries through increase of skin blood flow, thus enhancing the transdermal permeation amounts of drugs.

Effect of myrrh and thyme on Trichinella spiralisenteral and parenteral phases with inducible nitric oxide expression in mice

Trichinellosis is a serious disease with no satisfactory treatment. We aimed to assess the effect of myrrh (Commiphora molmol) and, for the first time, thyme (Thymus vulgaris L.) against enteral and encysted (parenteral) phases of Trichinella spiralis in mice compared with albendazole, and detect their effect on inducible nitric oxide synthase (iNOS) expression. Oral administration of 500 mg/kg of myrrh and thyme led to adult reduction (90.9%, 79.4%), while 1,000 mg/kg led to larvae reduction (79.6%, 71.3%), respectively. Administration of 50 mg/kg of albendazole resulted in adult and larvae reduction (94.2%, 90.9%). Positive immunostaining of inflammatory cells infiltrating intestinal mucosa and submucosa of all treated groups was detected. Myrrh-treated mice showed the highest iNOS expression followed by albendazole, then thyme. On the other hand, both myrrh and thyme-treated groups showed stronger iNOS expression of inflammatory cells infiltrating and surrounding encapsulated T. spiralis larvae than albendazole treated group. In conclusion, myrrh and thyme extracts are highly effective against both phases of T. spiralis and showed strong iNOS expressions, especially myrrh which could be a promising alternative drug. This experiment provides a basis for further exploration of this plant by isolation and retesting the active principles of both extracts against different stages of T. spiralis.

Extraction Optimization of Volatile Oil in Myrrh by Uniform Design / 中国药师

Objective:To optimize the extraction technology of volatile oil in myrrh. Methods: Using the extraction quantity of volatile oil as the index, the volatile oil was extracted by an essential oil extractor, and U6 (64 ) uniform design was used to investigate the influencing factors such as the immersion time ( A) , the mesh number ( B) , the extraction time ( C) and the additive water amount ( D) . Results:The optimized extraction technology was as follows: myrrh was crushed to obtain 10 mesh powder, soaked for 10 mi-nutes with 8-fold amount of water, and then extracted 3 hours. Conclusion:The quantity of volatile oil extracted from myrrh is accu-rate, the technology is reasonable, and the research provides scientific basis for the extraction of volatile oil in myrrh.

Effect of Myrrh Essential Oil on Percutaneous Absorption of Ibuprofen / 中国药师

Objective:To study the transdermal characteristics of myrrh essential oil and its percutaneous penetration enhancement for ibuprofen. Methods:The content of ibuprofen was determined by HPLC. Ibuprofen was used as the model drug and mouse skin was used as the permeation barrier in vitro. The transdermal properties of myrrh essential oil and its effect on percutaneous absorption of ibuprofen were investigated using Franz diffusion cells. Results:Without myrrh essential oil or with 1%, 2% and 3% myrrh essential oil, the cumulative transdermal penetration amount in 12h of ibuprofen in vitro was (0. 427 05 ± 0. 069 82), (0. 315 04 ± 0. 032 24), (0.230 50 ±0.031 14) and (0.181 34 ±0.053 70) mg·cm-2, with Jss of(0.031 4 ±0.005 7), (0.020 8 ±0.002 8), (0.017 2 ±0.001 6) and (0.013 9 ±0.003 4) mg·(cm2·h) -1, respectively. Conclusion: Myrrh essential oil shows no transdermal en-hancement for ibuprofen in vitro, to the contrary, it shows inhibitory effect with positive correlation to the concentration.

Análises das propriedades físicas e antimicrobianas de filmes a base de amigo contendo óleo essencial de Tetradenia riparia (Hochst.) Codd e Rosmarinus officinalis L. - Lamiaceae / Analysis of physical and antimicrobial properties of films based on starch containing Tetradonia riparia (Hochst.) and Rosmarinus officinalis L Clodd - Lamiaceae essential oil / Análisis de las propiedades físicas y antimicrobianas de películas a base de almidón conteniendo aceite esencial de Tetradenia riparia (Hochst.) Codd e Rosmarinus officinalis L. - Lamiaceae

Objetivando reduzir os impactos ambientais decorrentes do acúmulo de plásticos sintéticos, estão sendo desenvolvidas embalagens derivadas de polímeros renováveis, os chamados filmes biodegradáveis. Empregados na cobertura de produtos desidratados e frescos são capazes de conservar suas características sensoriais, valor nutritivo e evitar o desenvolvimento de micro-organismos (MO). Com este intuito, foram produzidos filmes com amido acetilado, gelatina e plastificante impregnados com óleos essenciais de Tetradenia riparia (Hochst.) Codd e Rosmarinus officinalis nas concentrações de 0,25; 0,5; 1; 2 e 3% (em relação à massa total do filme). Os parâmetros avaliados foram a espessura, solubilidade, opacidade e a capacidade de inibição microbiana frente aos micro-organismos Escherichia coli, Staphylococcus aureus e Candida albicans. Após a adição do óleo, observou-se redução na espessura nos filmes contendo R. officinalis quando comparados ao controle negativo (CN). Já nos filmes com T. riparia, os valores foram semelhantes ao CN, indicando melhor compatibilidade entre reagentes dos filmes a esse óleo. As solubilidades desses filmes aumentaram ao incorporar os óleos, exceto nos filmes com 0,25 e 1% do óleo de T. riparia, em que os valores ficaram próximos ao CN. A opacidade dos filmes com óleo de R. officinalis aumentou com o aumento da concentração deste óleo na composição do filme, porém nos filmes com T. Riparia, ocorreu o contrário a opacidade diminuiu com o acréscimo deste óleo nos filmes. Quanto ao filme incorporado com cloranfenicol, nos três parâmetros não houve diferenças significativas ao compará-lo com o CN. No teste microbiológico, para todos os filmes analisados, os MO demonstraram resistência comparados aos halos formados pelo controle positivo. Portanto, novos estudos deverão ser realizados, objetivando aumentar a compatibilidade dos filmes com os óleos, bem como novos óleos poderão ser analisados.

In order to reduce the environmental impacts resulting from the accumulation of synthetic plastic, packaging derived from renewable polymers are being developed, which are known as biodegradable films. Used in dried and fresh products, they are able to retain their sensory characteristics and nutritional value, as well as preventing the development of microorganisms (MO). For this purpose, films with acetylated starch, gelatin and plasticizer impregnated with Tetradenia riparia (Hochst.) Codd and Rosmarinus officinalis essential oils at concentrations of 0.25, 0.5, 1, 2 and 3% (relative to the total weight of the film) have been developed. This paper assessed the thickness, solubility, opacity and the capacity to inhibit Escherichia coli, Staphylococcus aureus and Candida albicans in these films. After the addition of oil, a decrease in the thickness of film incorporated with R. officinalis could be observed when compared to the negative control (NC). However, the film incorporated with T. riparia, the values were similar to the NC, indicating better compatibility between the film reagents and this oil. The solubility of these films increased when the oils were incorporated, except for the films with concentration of 0.25 and 1% of T. riparia oil, in which the values were close to the NC. The opacity of the films with R. officinalis oil increased with the increase in the concentration of oil in the composition of the film. However, in the films with T. riparia, the opposite could be noticed, that is, the opacity decreased with the addition of this oil in the films. For the films with chloramphenicol, there were no significant differences for the three parameters measured when compared to the NC. In the microbiological test, for all films analyzed, the MO showed resistance compared to the inhibition formed by the positive control. Therefore, further studies should be conducted in order to increase the compatibility of the films with the oils, as well as analyzing new oils;

Tegumental histological effects of Mirazid? and myrrh volatile oil on adult Fasciola gigantica

To evaluated the histological changes within the tegument of adult Fasciola gigantica (F. gigantica) that led to the gross changes that were visible externally. Methods: The effects of oleoresin extract of myrrh (Mirazid ? ), myrrh volatile oil and triclabendazole sulphoxide (reference drug) on the tegumental structure of adult F. gigantica following treatment in vitro had been determined by light microscopy. Results: The internal changes in the tegument observed in this study were compatible with surface changes seen in the previous scanning electron microscopy study, using the same drugs. The swelling of tegumental syncytium was a particular feature of their action, but its level was much greater with myrrh volatile oil, in which vacuolization of the tegument and loss of spines were observed. Conclusions: The present study demonstrated the fasciocidal properties of Mirazid ? oleoresin extract, and it might be possible to reinforce its fasciocidal activity by increasing its content of myrrh volatile oil.

Therapeutic Potential of Myrrh and Ivermectin against Experimental Trichinella spiralis Infection in Mice

Trichinosis is a parasitic zoonosis caused by the nematode Trichinella spiralis. Anthelmintics are used to eliminate intestinal adults as well as tissue-migrating and encysted larvae. This study aimed to investigate the effects of ivermectin and myrrh obtained from the aloe-gum resin of Commiphora molmol on experimental trichinosis. Ninety albino mice were orally infected with 300 T. spiralis larvae. Drugs were tested against adult worms at day 0 and day 5 and against encysted larvae on day 15 and day 35 post-infection (PI). Mature worms and encysted larvae were counted in addition to histopathological examination of muscle specimens. Serum aspartate aminotransferase (AST), alanine aminotransferase (ALT), total protein, albumin, globulin, urea, and creatinine values were estimated. Significant reductions in mean worm numbers were detected in ivermectin treated mice at day 0 and day 5 PI achieving efficacies of 98.5% and 80.0%, while efficacies of myrrh in treated mice were 80.7% and 51.5%, respectively. At days 15 and 35 post-infection, ivermectin induced significant reduction in encysted larval counts achieving efficacies of 76.5% and 54.0%, respectively, while myrrh efficacies were 76.6% and 35.0%, respectively. AST, ALT, urea, and creatinine levels were reduced, while total proteins were increased in response to both treatments compared to their values in the infected non-treated mice. Ivermectin use for controlling T. spiralis could be continued. Myrrh was effective and could be a promising drug against the Egyptian strains of T. spiralis with results nearly comparable to ivermectin.

Effects of Mirazid? and myrrh volatile oil on adult Fasciola gigantica under laboratory conditions

Objective: To evaluate the effects of Mirazid? and myrrh volatile oil on adult Fasciola gigantica (F. gigantica ) under laboratory conditions. Methods: The effects of oleoresin extract of myrrh (Mirazid?) and myrrh volatile oil on the surface morphology of adult F. gigantica following treatment in vitro had been determined by scanning electron microscopy. The results were compared with those observed in the fluke tegument following incubation in triclabendazole sulphoxide (TCBZ-SO), active form, (Fasinex?, Ciba-Geigy). Results: Observations of the efficacy of Mirazid? oleoresin extract and myrrh volatile oil indicated that both products showed dose-dependent anthelmintic efficacy. The anterior half of the fluke was consistently more severely affected than the posterior half. The surface changes induced by Mirazid? oleoresin extract were less severe than those observed after exposure to either myrrh volatile oil or TCBZ-SO. Flukes showed swelling after these treatments, but its level and blebbing were much greater with myrrh volatile oil; in which patches of tegumental sloughing were observed in the apical cone and the posterior mid-body region of flukes. This was not observed after treatment with Mirazid? oleoresin extract. Conclusions: The comparatively more disruption, observed in myrrh volatile oil exposed specimens, compared to that exposed to Mirazid? oleoresin extract might suggest that the anthelmintic activity of Mirazid? oleo resin extract was attributed to its content of volatile oil. So, increasing the concentration of myrrh volatile oil in Mirazid? might possibly help to developing its anthelmintic activity.

A Case of Anal Erosion Treated with Chamomile and Myrrh Extracts / 대한피부과학회지

Anal disorders are common and more than one half of the population will experience one at some time during their lives. Anal erosion and fissures can cause discomfort, severe pain, bleeding and inflammation. In the acute phase of anal erosion, with bowel habit management and topical emollient, lesions can be improved. Chamomile and Myrrh are known for centuries to have several effects and have anti-inflammatory, sedative, antibacterial and antifugal properities. Here, We report a case of anal erosion treated with Chamomile and Myrrh extracts (Ad-Muc(R)). Our case indicates that Chamomile and Myrrh extracts might play a role in the management of anal erosion and fissure.