Aporphine alkaloids from Piper erecticaule and acetylcholinesterase inhibitory activity / Alcaloides de aporfina obtenida de Piper erecticaule y actividad inhibitoria de la acetilcolinesterasa

Chemical constituents and biological activities of the aerial parts of Piper erecticaule C.DC. have been studied for the first time. Fractionation and purification of the extracts afforded aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4), piperolactam D (5), together with terpenoids of ß-sitosterol, ß-sitostenone, taraxerol, and lupeol. The structures of these compounds were obtained by analysis of their spectroscopic data, as well as the comparison with that of reported data. Acetylcholinesterase inhibitory activity revealed that compounds 1 and 3 showed strong AChE inhibitory effects with the percentage inhibition of 75.8% and 74.8%, respectively.

Se estudiaron por primera vez los constituyentes químicos y actividad biológica de las partes aéreas de Piper erecticaule C.DC. El fraccionamiento y la purificación de los extractos proporcionaron aristolactama AII (1), aristolactama BII (2), piperolactama A (3), piperolactama C (4), piperolactama D (5), junto con terpenoides de ß-sitosterol, ß-sitostenona, taraxerol, y el lupeol. Las estructuras de estos compuestos se obtuvieron mediante el análisis de sus datos espectroscópicos, así como mediante la comparación con datos ya informados. La actividad inhibidora de la acetilcolinesterasa reveló que los compuestos 1 y 3 mostraron un potente efecto inhibidor de la AChE con un porcentaje de inhibición del 75.8% y 74.8%, respectivamente.

Comparative toxicity of essential oil and blends of selected terpenes of Ocotea species from Pernambuco, Brazil, against Tetranychus urticae Koch

ABSTRACT Essential oils from the leaves of two species of the genus Ocotea that occur in the Atlantic Forest in the state of Pernambuco, Brazil, were analyzed using gas chromatography-mass spectrometry. The acaricidal activity of these oils as well as 11 selected components and blends were evaluated in fumigation and residual contact tests against the two-spotted spider mite (Tetranychus urticae). Sixty-seven constituents were identified, totaling 97.3 ± 0.3% and 97.8 ± 0.5% of the oils from O. duckei and O. glomerata, respectively. Sesquiterpene was the dominant class. The compounds β-caryophyllene (18.6 ± 0.1%) and aromadendrene (17.3 ± 0.6%) were the main constituents of the oils from O. duckei and O. glomerata, respectively. Acaricidal action varied depending on the method employed, species and chemical nature of the selected constituents. The mites were susceptible to the oils and chemical constituents using the fumigation method. The O. duckei oil was respectively 2.5-fold and 1.5-fold more toxic than the O. glomerata oil using the fumigation and residual contact methods. Among the selected constituents, β-caryophyllene was the most toxic, independently of the method employed. The individual toxicity of the selected compounds and their blends as well as the role of these constituents in the overall toxicity of the essential oils are also discussed.

Chemical composition of the essential oil from Ageratina jocotepecana and its repellent effect on drywood termite incisitermes marginipennis / Composición química del aceite esencial de Ageratina jocotepecana y su efecto repelente en termitas de madera seca incisitermes marginipennis

Essential oils obtained from new plant species with metabolomes unexplored or poorly known are a natural resource to find molecules with deterrent (irritant) effect. The aim of this study was to evaluate the chemical composition and the termite repellent activity of the essential oils from Ageratina jocotepecana. The repellent effect was determined by the pine drywood termite Incisitermes marginipennis behavior of to sense the contact of the tunnel wall in the wooden colony in the presence of an irritant obstacle caused by essential oils. Gas chromatographic analysis of the essential oils from flower, leaf, and stem showed quantitative and qualitative differences in components. Twenty-eight volatile components were identified by their mass spectra (MS). beta-caryophyllene, carvacrol, spathulenol, and terpinen-4-ol were the four major components, of them in relation 0.1 M citronellol, the 0.1 M carvacrol was the best repellent of the termite. Essential oils from A. jocotepecana exhibited a termite repellent effect due to their major components. Additionally, more research about the termite repellent action of carvacrol is still needed.

Los aceites esenciales obtenidos de nuevas especies de plantas con metabolomas inexplorados o poco conocidos son un recurso natural para encontrar moléculas con efecto disuasivo (irritante). El propósito del estudio fue evaluar la composición química de los aceites esenciales de Ageratina jocotepecana y su actividad repelente de termitas. El efecto repelente fue determinado por el comportamiento de las termitas de la madera seca de pino Incisitermes marginipennis de sentir el contacto de la pared del túnel en la colonia de madera en la presencia de un obstáculo irritante causado por los aceites esenciales. El análisis de cromatografía de gases de los aceites esenciales de flores, hojas y tallo mostró diferencias cuantitativas y cualitativas en componentes. Veintiocho componentes volátiles fueron identificados por sus espectros de masas (MS). beta-cariofileno, carvacrol, spathulenol y terpinen-4-ol fueron los cuatro componentes mayoritarios, de ellos en relación con 0,1 M citronelol el control positivo, el carvacrol 0,1 M fue el mejor repelente de la termita. Además, más investigación sobre la acción repelente de termitas de carvacrol se necesita realizar.

Variabilidad química del “tomillo silvestre” (acantholippia seriphioides, verbenaceae) en la meseta Patagónica / Chemical Variability of “tomillo silvestre” (acantholippia seriphioides, verbenaceae) in the Patagonian plateau

El tomillo silvestre es una planta aromática y medicinal de amplio uso en varias regiones de Argentina como medicinal y saborizante. Se estudiaron poblaciones de Acantholippia seriphioides en dos zonas de la meseta chubutense, los parajes El Pajarito y La Rueda. Las partes aéreas oreadas fueron extraídas por hidrodestilación y los aceites esenciales se analizaron por GC-FID-MS. Los rendimientos en promedio de aceites esenciales fueron de 5.2 ml/kg y 3.2 ml/kg, para La Rueda y El Pajarito respectivamente. Los tipos químicos encontrados fueron: ipsilon-terpineno/timol/carvacrol en La Rueda y mirtenol/geraniol/carvona en El Pajarito. El probable quimiotipo de este último sitio difiere marcadamente de los reportados en trabajos previos para esta especie y presenta además importante variabilidad cuantitativa, según el estado fenológico.

“Tomillo silvestre” is a widespread medicinal and aromatic plant with medicinal and flavoring uses in numerous regions of Argentina. Acantholippia seriphioides populations from two areas of the Chubut’s plateau: El Pajarito and La Rueda, have been studied. The dried aerial parts were extracted by hydrodistillation and the essential oils were analyzed by GC/FID/MS. The average yields of oils were 5.2 ml/kg and 3.2 ml/kg for La Rueda and El Pajarito, respectively. The chemical profiles found were: ypsilon-terpinene/thymol/carvacrol in La Rueda and myrtenol/geraniol/carvone in El Pajarito. The feasible chemotype from the latter area is significantly different from those previously reported for this species, and it also showed an important quantitative variation according to the phenological stages.

Chemical composition and biological activity of essential oil of achyrocline ramosissima briton ex rusby (asteraceae) / Composición química y actividad biológica del aceite esencial de achyrocline ramosissima britton ex rusby (asteraceae)

Essential oil from fresh aerial parts of Achyrocline ramosissima Britton ex Rusby (Asteraceae) collected in the Venezuelan Andes was obtained by hydrodistillation and analyzed by GC/MS. A yield of 0.10 percent w/v was afforded, and thirty seven components were identified by comparison of their retention indices (RI) and mass spectra with the Wiley GC-MS Library Data. The major components identified were rosifoliol (31.69 percent), beta-caryophyllene (8.61 percent), guaiol (3.95 percent), beta-eudesmol (3.33 percent) and selina-3,7 (11)-diene (2.99 percent). Antimicrobial activity of A. ramosissima essential oil was also evaluated against Gram positive, Gram negative bacterial strains and Candida albicans yeast. The results showed that, this oil is effective against Gram positive bacteria Staphylococcus aureus ATCC 6538 with MIC values ranging from 50 to 100 μg/mL and MBC values > 200 μg/mL as well as Bacillus subtilis CECT 39 with MIC values of 50 μg/mL and MBC of 100 μg/mL, however a low activity was observed against Gram negative bacterial strains, Pseudomonas aeruginosa AK 958, Escherichia coli CECT 99 and C. albicans yeast performing MIC and MBC values > 200 μg/mL. Cytotoxic activity was also determined against HeLa (cervix carcinoma), A-459 (lung carcinoma), MCF-7 (breast adenocarcinoma) human cancer cell lines and against normal Vero cells (African green monkey kidney), exhibiting antiproliferative effects with IC50 values of 28.2 μg/mL (HeLa cells). This is the first report regarding the chemical composition, antibacterial and cytotoxic activities of the essential oil from this species.

El aceite esencial de las partes aéreas frescas de Achyrocline ramosissima Britton ex Rusby (Asteraceae) recolectada en los Andes venezolanos fue extraído por hidrodestilación y analizado por CG/EM. Se obtuvo un rendimiento de 0,10 por ciento m/v, treinta y siete componentes fueron identificados por comparación de los índices de retención (IR) y sus espectros de masas con los datos de la biblioteca Wiley GC-MS. Los principales componentes identificados fueron rosifoliol (31,69 por ciento), beta-cariofileno (8,61 por ciento), guaiol (3,95 por ciento), beta-eudesmol (3,33 por ciento) y selina-3,7 (11)-dieno (2,99 por ciento). La actividad antimicrobiana del aceite esencial de A. ramosissima fue evaluada contra cepas bacterianas Gram positivas, Gram negativas y la levadura Candida albicans. Los resultados mostraron que el aceite esencial fue activo contra las bacterias Gram positivas Staphylococcus aureus ATCC 6538 con una CIM entre 50-100 μg/mL y CBM de valores > 200 μg/mL y Bacillus subtilis CECT 39 con CIM de 50 μg/mL y CBM de 100 μg/mL, sin embargo se observó una baja actividad contra las cepas bacterianas Gram negativas Pseudomonas aeruginosa AK 958, Escherichia coli CECT 99 y la levadura C. albicans cuyos valores de CIM y CBM fueron > 200 μg/mL. La actividad citotóxica fue determinada frente a las líneas celulares cancerígenas HeLa (carcinoma de cuello uterino), A-459 (carcinoma de pulmón), MCF-7 (adenocarcinoma de mama) y frente a las células normales Vero (células renales de mono verde), mostrando efectos antiproliferativos con valores de CI50 28.2 μg/mL frente a las células HeLa. Este es el primer reporte sobre la composición química, actividad antibacteriana y citotóxica del aceite esencial de esta especie.

Lipophilic metabolite profiling of maize and sorghum seeds and seedlings, and their pest spotted stem borer larvae: A standardized GC-MS based approach.

In order to better understand the biochemical interactions and to identify new biomarkers for plant resistance against insects, we proposed a suitable lipophilic profiling method for insects and their host plants. The critical components of GC-MS based analysis are: sample amount, extraction, derivatization, temperature gradient, run time, and identification of peaks. For lipophilic metabolite profiling of maize and sorghum, and their insect pest, spotted stem borer larvae, we recommend 100 mg sample weight for seeds and insect samples (whole insect body), and 200 mg for seedlings. Maize and sorghum seeds required less time for fat extraction in comparison to their seedlings and the pest fed on these seedlings. GC-MS was standardized for better separation and intensity of peaks using different temperature gradients in the range of 180-300 C. A total of 48 lipophilic compounds encompassing various classes based on their functional groups such as fatty acids, fatty alcohols, hydrocarbons, sterols and terpenoids, vitamin derivative, etc. were separated in the seedlings (30), seeds (14), and the pest (26) in the retention time range of 3.22 to 29.41 min. This method could be useful to study nutritional aspects of different field crops in relation to various stresses apart from the analysis of lipophilic compounds for better understanding of insect-plant interactions.

Isolation of Polysaccharides and Terpenoids from Some Basidiomycota and Their Antibacterial Activities.

Aims: Antibacterial chemicals were isolated from fruit bodies of three basidiomycota [Coltricia perennis (L) Murrill, Onnia tomentosa (Fr.) P. Karst., and Polyporus mori (Pollini) Fr. ] fungi and their antibacterial potential were screened against five bacteria. Study Design: All experiments were performed thrice in completely randomized design (CRD) each, with five replications per treatment (antibacterial activity). The data was subjected to ANOVA. Means of three observations were compared with Duncan’s Multiple Range Test (DMRT). Place and Duration of Study: Molecular Mycopathology Laboratory, Department of Botany, Ramakrishna Mission Vivekananda Centenary College, Rahara, Kolkata, between January 2012 and February 2013. Methodology: During the rainy season in the year of 2012, a survey for mushroom collection in the forest beds, infected logs in the plain of west Bengal was conducted .The fruit bodies of some basidiomycota were collected in sterile biodegradable polythene begs and brought to laboratory. The morphology, anatomy of fruit bodies and measurement of reproductive organs were recorded. The spore prints of all collected basidiocarps were taken.The collected basidiomycota were identified. The polysaccharides from the basidiocarps of the test fungi were isolated employing the methods of Mizuno et al. [17] and Wang et al.[12].Terpeniods were isolated according to the method followed by Anke and Werte [24] and Chairul et al. [25]. Their antibacteral activities were assayed against five bacteria [three Gram positive bacteria (Staphylococcus aureus, Micrococcus roseus and Bacillus brevis ) and two Gram negative bacteria (Ralstonia solanacearum and Escherichia coli )] following the agar plates cup diffusion techniques. Results: Terpenoid isolated from Coltricia perennis was most active in inhibiting the growth of all five bacteria. This terpenoid inhibited maximum (25 ±2.4mm) growth against Staphylococcus aureus and minimum against Micrococcus roseus (17±1.1mm). The polysaccharides isolated from these three mushrooms were less active against the test five bacteria. The terpenoids isolated from Onnia tomentosa and Polyporus mori also inhibited the growth of the test bacteria. Conclusion: These three basidiomycetous mushrooms have antibacterial activity. After further research, their activity can be employed in medical science.

Sedative and anesthetic activities of the essential oils of Hyptis mutabilis (Rich.) Briq. and their isolated components in silver catfish (Rhamdia quelen)

This study evaluated the sedative and anesthetic effects of the essential oils (EO) of Hyptis mutabilis (Rich.) Briq. and their isolated components on silver catfish (Rhamdia quelen). Quantitative chemical differences between the EOs obtained from leaves and inflorescences were verified, and a new chemotype rich in globulol was described. Although there were no significant differences in the time of induction for sedation and anesthesia between the EOs, only the leaf EO at 344 mg/L anesthetized all fish without side effects. Fractionation of the leaf EO was carried out by column chromatography. The isolated compounds [(+)-1-terpinen-4-ol and (-)-globulol] showed different activity from that detected for the leaf EO in proportional concentrations and similar sedation to a eugenol control at 10 mg/L. However, fish exposed to 1-terpinen-4-ol (3 and 10 mg/L) did not remain sedated for 30 min. Anesthesia was obtained with 83-190 mg/L globulol, but animals showed loss of mucus during induction and mortality at these concentrations. Synergism of the depressor effects was detected with the association of globulol and benzodiazepine (BDZ), compared with either drug alone. Fish exposed to BDZ or globulol+BDZ association showed faster recovery from anesthesia in water containing flumazenil, but the same did not occur with globulol. In conclusion, the use of globulol in aquaculture procedures should be considered only at sedative concentrations of 10 and 20 mg/L, and its mechanism of action seems not to involve the GABAA-BDZ system.

Ceramides and terpenoids from Russula austrodelica Singer / Ceramidas y terpenoides desde Russula austrodelica Singer

A mixture of ceramides and known terpenes, was obtained from the fruiting bodies of Russula austrodelica. The structures were determined from chemical and spectroscopic evidence. R. austrodelica is a mycorrhizal fungus that grow in the Nothophagus forests of southern Chile. This is the first report of the isolation of ceramides in Chilean mushrooms.

Una mezcla de ceramidas y de terpenos conocidos, se obtuvo de los cuerpos fructíferos de Russula austrodelica. Las estructuras fueron determinadas a partir de evidencias químicas y espectroscópicas. R. austrodelica es un hongo micorrícico que crecen en los bosques de Nothophagus del sur de Chile. Este es el primer informe del aislamiento de ceramidas en hongos chilenos.

Cytotoxic terpenoids from Satureja macrantha C. A. Mey

From the aerial parts of Satureja macrantha C. A. Mey, one monoterpene [1], two triterpenoids [2,3] and one sesquiterpene [4] were isolated. Their structures were determined to be thymol [1], oleanolic acid [2], ursolic acid [3] and caryophyllene oxide [4], by using 1H and 13C-NMR, FTIR and EIMS spectra. Brine shrimp cytotoxicity effects of the crude extracts and isolated compounds were examined. Among them compounds 1 [612 microM], 2 [17 microM] and 3 [29 microM] were effective against Artemia salina larva

Antidepressant activity of hyperforin conjugates of the St. John's wort, Hypericum perforatum Linn.: an experimental study.

Nine extracts of H. perforatum, containing hyperforin in conjugated forms, but devoid of free hyperforin and adhyperforin, were subjected to antidepressant screening using the forced swim test (FST). The observed activity was compared with that of SJW extracts containing hyperforin and adhyperforin (in free form). Results indicate that hyperforin conjugates exhibit significant antidepressant activity as evidenced by the reduced immobility period in the FST in rats.

Oxidative stress in rat liver and lung induced by furanoterpenoids isolated from Fusarium solani infected sweet potatoes.

A crude extract containing some toxic furanoterpenoids was isolated from F. solani infected sweet potatoes. Chronic administration of the crude extract to male albino rats at a dosage of 1 mg/kg body weight/day for 21 days brought about a sharp increase in the thiobarbituric acid reactive substances and a depression of glutathione levels in the lung and liver homogenates. The antioxidant defense system was affected as evident from a significant fall in the activities of the enzymes, superoxide dismutase, catalase, glutathione peroxidase, glucose-6-phosphate dehydrogenase and glutathione-S-transferase. Such an alteration could be the reason for the lung and liver damage caused by these toxic furanoterpenoids.

Actividad antifúngica y antibacteriana de Ageratina ibaguensis / Antifungal and antibacterial activity of Ageratina ibaguensis

De la parte áerea de Ageratina ibaguensis (Schultz-Bip.ex Hieron) R.M. King & H. Robinson se aisló un terpenoide que presentó actividad antimicrobiana. La concentración crítica antifúngica está comprendida entre 500 y 2000 mcg/ml y la actividad antibacterina entre 190-930 mcg/ml

Diterpene quinones from the roots of salvia lanigera poir

Fractionation of the antimicrobial petr. extract of Salvia lanigera Poir. roots, afforded two more diterpene quinones deoxyneocryptotanshinone I and 7-oxoroyleanone II. Their structures were elucidated using 400 MHz 1H-NMR and other spectroscopic evidences

Bioactive glycosides from Chinese medicines

Glycosides are the bioactive components of many famous Chinese medicines. Here reported are some bioactive glycosides we discovered from Chinese medicines in recent years. (1) Pheolic glycosides from Chinese medicines: Gastrodia elata, acontium austroynanense and Helicia erratica, three bioactive phenolic glycosides were discovered and two of them have been developed into new drugs. (2) Terpenoidal glycosides: a) Monoterpenoid: the sweroside from Swertia mollensis has been developed intro an anti-hepatitis drug; b) Diterpenoid: Phlomis betonicoides contains sweet glycoides; c) Triterpenoid: many biologically active triterpenoid glycosides were isolated from Panax plants and Siraitia grosvenorii. (3) Steroidal glycosides: a) C21-steroid: Cynanchum otophyllum and C. atratrum contain anti-epilepsy and-tumor glycosides; b) C27-steroid Hemostatic saponins were found in Paris polyphylla.