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China Journal of Chinese Materia Medica ; (24): 2464-2470, 2023.
Article in Chinese | WPRIM | ID: wpr-981322


This paper explored the chemical constituents of Boswellia carterii by column chromatography on silica gel, Sephadex LH-20, ODS column chromatography, and semi-preparative HPLC. The structures of the compounds were identified by physicochemical properties and spectroscopic data such as infrared radiation(IR), ultra violet(UV), mass spectrometry(MS), and nuclear magnetic resonance(NMR). Seven diterpenoids were isolated and purified from n-hexane of B. carterii. The isolates were identified as(1S,3E,7E,11R,12R)-11-hydroxy-1-isopropyl-4,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadeca-3,7-dien-5-one(1),(1R,3S,4R,7E,11E)-4,8,12,15,15-pentamethyl-14-oxabicyclo[11.2.1]hexadeca-7,11-dien-4-ol(2), incensole(3),(-)-(R)-nephthenol(4), euphraticanoid F(5), dilospirane B(6), and dictyotin C(7). Among them, compounds 1 and 2 were new and their absolute configurations were determined by comparison of the calculated and experimental electronic circular dichroisms(ECDs). Compounds 6 and 7 were obtained from B. carterii for the first time.

Molecular Structure , Boswellia/chemistry , Diterpenes/chemistry , Mass Spectrometry
China Journal of Chinese Materia Medica ; (24): 96-104, 2023.
Article in Chinese | WPRIM | ID: wpr-970505


By various chromatographic techniques and extensive spectroscopic methods, 17 abietane diterpenoids were isolated from the dichloromethane fraction of the 95% ethanol cold-soak extracts of the seeds of Pseudolarix amabilis, namely pseudoamaol A(1), 12α-hydroxyabietic acid(2), 12-methoxy-7,13-abietadien-18-oic acid(3), 13-hydroxy-8,11,13-podocarpatrien-18-oic acid(4), 15-hydroxy-7,13-abietadien-12-on-18-oic acid(5), 8(14)-podocarpen-13-on-18-oic acid(6), holophyllin K(7), metaglyptin B(8), 7α-hydroxydehydroabietinsaure-methylester(9), 7-oxodehydroabietic acid(10), 15-hydroxy-7-oxodehydroabietinsaure-methy-lester(11), 15-methoxydidehydroabietic acid(12), 7-oxo-15-hydroxy-dehydroabietic acid(13), 15-hydroxydehydroabietic acid(14), 8,11,13-abietatriene-15,18-diol(15), 8,11,13-abietatriene-15-hydroxy-18-succinic acid(16), and 7β-hydroxydehydroabie-tic acid(17). Compound 1 was a new compound. The isolated compounds were evaluated for their antitumor activities(HepG2, SH-SY5Y, K562), and compounds 8 and 17 showed potential cytotoxic activity against K562 cells, with IC_(50) values of 26.77 and 37.35 μmol·L~(-1), respectively.

Humans , Molecular Structure , Neuroblastoma , Diterpenes/chemistry , Antineoplastic Agents
Chinese Journal of Natural Medicines (English Ed.) ; (6): 551-560, 2023.
Article in English | WPRIM | ID: wpr-982724


Phytochemical investigation on the ethanol extract of a well-known medicinal herb Leonurus japonicus, led to the separation of 18 labdane type diterpenoids (1-18). Through comprehensive spectroscopic analyses and quantum chemical calculations, these compounds were structurally characterized as six new interesting 5,5,5-di-spirocyclic ones (1-6), two new (7 and 8) and six known (13-18) interesting 6,5,5-di-spirocyclic ones, a new rare 14,15-dinor derivative (9), and three new ones incorporating a γ-lactone unit (10-12). An in vitro neuroprotective assay in RSC96 cells revealed that compounds 7 and 12 exhibited neuroprotective activity in a concentration-dependent way, comparable to the reference drug N-acetylcysteine.

Magnetic Resonance Spectroscopy , Leonurus/chemistry , Plants, Medicinal , Diterpenes/chemistry , Plant Components, Aerial , Molecular Structure
Chinese Journal of Natural Medicines (English Ed.) ; (6): 298-307, 2023.
Article in English | WPRIM | ID: wpr-982701


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.

Terpenes/pharmacology , Viburnum/chemistry , Molecular Structure , Diterpenes/chemistry , Plant Leaves/chemistry
China Journal of Chinese Materia Medica ; (24): 3765-3773, 2023.
Article in Chinese | WPRIM | ID: wpr-981509


Small-molecule compounds with rich sources have diverse structures and activities. The active ingredients in traditional Chinese medicine(TCM) provide new sources for the discovery of new antitumor drugs. Aconitum plants as Chinese medicinal plants have the effects of dispelling wind, removing dampness, warming meridian, and relieving pain. They are mainly used to treat inflammation, pain, rheumatism, and tumors, improve heart function, and dilate blood vessels in clinical practice. Diterpenoid alkaloids are the main active components of Aconitum plants, including C20-, C19-, C18-diterpenoid alkaloids and bis-diterpenoid alkaloids. Stu-dies have demonstrated that diterpenoid alkaloids can effectively treat lung cancer, liver cancer, breast cancer, colon cancer and other cancers. Diterpenoid alkaloids are considered as the most promising natural compounds against cancers. In this review, we summarized the chemical structures and antitumor activities of C20-, C19-, C18-diterpenoid alkaloids and bis-diterpenoid alkaloids extracted from plants of Aconitum, aiming to provide reference for further development of diterpenoid alkaloids from Aconitum as antitumor drugs.

Humans , Aconitum/chemistry , Molecular Structure , Alkaloids/analysis , Diterpenes/chemistry , Antineoplastic Agents/chemistry , Plant Roots/chemistry
Bol. latinoam. Caribe plantas med. aromát ; 19(2): 236-246, mar. 2020. ilus, tab
Article in English | LILACS | ID: biblio-1104216


Chloroform extract (CE) and fractions obtained from Aldama arenaria roots were evaluated for their in vitro antiproliferative activity against 10 human tumor cell lines [leukemia (K-562), breast (MCF-7), ovary expressing a multidrug-resistant phenotype (NCI/ADR-RES), melanoma (UACC-62), lung (NCI-H460), prostate (PC-3), colon (HT29), ovary (OVCAR-3), glioma (U251), and kidney (786-0)]. CE presented weak to moderate antiproliferative activity (mean log GI50 1.07), whereas fractions 3 and 4, enriched with pimaranetype diterpenes [ent-pimara-8(14),15-dien-19-oic acid and ent-8(14),15-pimaradien-3ß-ol], presented moderate to potent activity for most cell lines, with mean log GI50 of 0.62 and 0.59, respectively. The results showed promising in vitro antiproliferative action of the samples obtained from A. arenaria, with the best results for NCI/ADR-RES, HT29, and OVCAR-3, and TGI values ranging from 5.95 to 28.71 µ -1, demonstrating that compounds of this class may be potential prototypes for the discovery of new therapeutic agents.

El extracto de cloroformo (CE) y las fracciones obtenidas de las raíces de Aldama arenaria fueron evaluadas por su actividad antiproliferativa in vitro contra 10 líneas celulares tumorales humanas [leucemia (K-562), mama (MCF-7), ovario que expresa un fenotipo resistente a múltiples fármacos (NCI/ADR-RES), melanoma (UACC-62), pulmón (NCI-H460), próstata (PC-3), colon (HT29), ovario (OVCAR-3), glioma (U251) y riñón (786-0)]. CE presentó actividad antiproliferativa débil a moderada (log GI50 promedio de 1.07), mientras que las fracciones 3 y 4, enriquecidas con diterpenos de tipo pimarane [ent-pimara-8 (14), ácido 15-dien-19-oico y ent-8 (14), 15-pimaradien-3ß-ol], presentaron actividad moderada a potente para la mayoría de las líneas celulares, con un log GI50 promedio de 0.62 y 0.59, respectivamente. Los resultados mostraron una prometedora acción antiproliferativa in vitro de las muestras obtenidas de A. arenaria, con los mejores resultados para NCI/ADR-RES, HT29 y OVCAR-3, y valores de TGI que van desde 5.95 a 28.71 µ -1, lo que demuestra que los compuestos de esta clase pueden ser prototipos potenciales para el descubrimiento de nuevos agentes terapéuticos.

Plant Extracts/pharmacology , Chloroform , Plectranthus/chemistry , Cell Line, Tumor/drug effects , Cell Proliferation/drug effects , In Vitro Techniques , Plant Extracts/chemistry , Ethnobotany , Cuba , Diterpenes/pharmacology , Diterpenes/chemistry
An. acad. bras. ciênc ; 89(3,supl): 1961-1969, 2017. tab, graf
Article in English | LILACS | ID: biblio-886788


ABSTRACT The in vitro metabolism of a widespread natural product, trachyloban-19-oic acid (1), by the fungal species Mucor plumbeus was studied in a sucrose-yeast liquid medium. Two products were isolated, and their structures were determined by spectroscopic means as 7β-hydroxytrachyloban-19-oic acid (5) and trachyloban-19-O-β-D-glucopyranosyl ester (6). To the best of our knowledge, compound 6 is herein reported by the first time in the literature. These compounds were assayed for acetylcholinesterase inhibition along with some related compounds. Compound 6 showed the highest acetylcholinesterase inhibitory activity at 10000 µg/mL among the tested compounds, a result (92.89%) comparable to the activity of the positive control, galanthamine (94.21%). Therefore, biotransformation of the natural product 1 by M. plumbeus produced a novel compound with potential as a new lead to develop anti-Alzheimer medicines.

Cholinesterase Inhibitors/metabolism , Culture Media/chemistry , Diterpenes/metabolism , Mucor/metabolism , Glycosylation , Plant Extracts , Biotransformation , Cholinesterase Inhibitors/chemistry , Diterpenes/chemistry
Arq. bras. cardiol ; 106(6): 481-490, tab, graf
Article in English | LILACS | ID: lil-787323


Abstract Background: Labdane-type diterpenes induce lower blood pressure via relaxation of vascular smooth muscle; however, there are no studies describing the effects of labdanes in hypertensive rats. Objective: The present study was designed to investigate the cardiovascular actions of the labdane-type diterpene ent-3-acetoxy-labda-8(17), 13-dien-15-oic acid (labda-15-oic acid) in two-kidney 1 clip (2K-1C) renal hypertension. Methods: Vascular reactivity experiments were performed in aortic rings isolated from 2K-1C and normotensive (2K) male Wistar rats. Nitrate/nitrite (NOx) measurement was performed in aortas by colorimetric assay. Blood pressure measurements were performed in conscious rats. Results: Labda-15-oic acid (0.1-300 µmol/l) and forskolin (0.1 nmol/l - 1 µmol/l) relaxed endothelium-intact and endothelium-denuded aortas from both 2K-1C and 2K rats. Labda-15-oic acid was more effective at inducing relaxation in endothelium-intact aortas from 2K pre-contracted with phenylephrine when compared to the endothelium-denuded ones. Forskolin was more potent than labda-15-oic acid at inducing vascular relaxation in arteries from both 2K and 2K-1C rats. Labda-15-oic acid-induced increase in NOx levels was lower in arteries from 2K-1C rats when compared to 2K rats. Intravenous administration of labda-15-oic acid (0.3-3 mg/kg) or forskolin (0.1-1 mg/kg) induced hypotension in conscious 2K-1C and 2K rats. Conclusion: The present findings show that labda-15-oic acid induces vascular relaxation and hypotension in hypertensive rats.

Resumo Fundamento: Diterpenos do tipo labdano induzem uma queda da pressão arterial por meio do relaxamento do músculo liso vascular; todavia, não há estudos que descrevam os efeitos de labdanos em ratos hipertensos. Objetivo: O presente estudo foi desenvolvido para investigar as ações cardiovasculares do labdano ácido ent-3-acetóxi-labda-8(17),13-dieno-15-óico (labda-15-óico) na hipertensão renal dois rins-1 clipe (2R-1C). Métodos: Foram feitos experimentos de reatividade vascular em anéis aórticos isolados de ratos machos 2R-1C e normotensos (2R). A medição de Nitrato/Nitrito (NOx) foi feita nas aortas por meio de ensaio colorimétrico. As medidas de pressão arterial foram feitas em ratos conscientes. Resultados: O ácido labda-15-óico (0,1 - 300 µmol/l) e a forscolina (0,1 nmol/l - 1 µmol/l) relaxaram as aortas com endotélio intacto e as aortas sem endotélio dos ratos 2R-1C e 2R. O labda-15-óico mostrou-se mais eficaz na indução do relaxamento em aortas com endotélio intacto de 2R pré-contraídas com fenilefrina em comparação àquelas sem endotélio. A forscolina mostrou-se mais potente do que o ácido labda-15-óico na indução do relaxamento vascular nas artérias tanto de ratos 2R-1C quanto de ratos 2R. O aumento dos níveis de NOx induzido pelo ácido labda-15-óico foi menor nas artérias de ratos 2R-1C em comparação a ratos 2R. A administração intravenosa de ácido labda-15-óico (0,3-3 mg/kg) ou forscolina (0,1-1 mg/kg) induziu hipertensão em ratos 2R-1C e 2R conscientes. Conclusão: Os presentes resultados mostram que o labda-15-óico induz relaxamento vascular e hipotensão em ratos hipertensos.

Animals , Male , Rats , Vasodilator Agents/pharmacology , Blood Pressure/drug effects , Colforsin/pharmacology , Diterpenes/pharmacology , Hypertension, Renovascular/drug therapy , Aorta, Thoracic/drug effects , Phenylephrine/antagonists & inhibitors , Vasoconstrictor Agents/antagonists & inhibitors , Vasodilation/drug effects , Vasodilator Agents/chemistry , Colforsin/chemistry , Rats, Wistar , Disease Models, Animal , Diterpenes/chemistry , Drug Evaluation, Preclinical , Hypertension, Renovascular/physiopathology , Muscle, Smooth, Vascular/drug effects , Nitric Oxide/analysis
Cad. saúde pública ; 31(4): 837-849, 04/2015. tab, graf
Article in Spanish | LILACS | ID: lil-744855


Comprender el significado del capital social de la diabetes tipo 2 según género, dentro un contexto urbano colombiano. Investigación cualitativa del interaccionismo simbólico. 25 mujeres y 16 hombres, diabéticos, familiares, vecinos y personal asistencial participaron en seis grupos focales. Emergieron 850 códigos que se integraron en un set de 142 códigos de códigos para el ego, el alter y alter ego. Tres categorías y veinte subcategorías fueron identificadas para el diseño del "paradigma de la codificación". El significado no es igual para hombres y mujeres. Los vínculos sociales de las redes sociales, creados cotidianamente por la confianza y la solidaridad para el cuidado, son valorados de manera diferente, debido a experiencias y hechos sociales resultantes de la autoconfianza, la autoeficacia para el apoyo social principalmente y, la autoestima frente al manejo y control de la enfermedad. Los recursos sociales de un individuo son reificados para el manejo y cuidado de la enfermedad como estrategia para disminuir las inequidades en salud.

The aim of this study was to understand the meaning of social capital in relation to type 2 diabetes according to gender, within an urban setting in Colombia, based on a qualitative design for symbolic interactionism. Twenty-four women and 16 men with diabetes, family members, and healthcare personnel participated in six focus groups. A total of 850 codes emerged that comprised a set of 142 codes for ego, alter, and alter ego. Three categories and 20 subcategories were identified for the "coding paradigm design". The meaning differed between men and women. Social ties in social networks, created daily through trust and solidarity for care, were valued differently due to the social experiences and events resulting from self-confidence, self-efficacy for social support, and mainly self-esteem vis-à-vis management and control of the disease. An individual's social resources are reified for the management and care of the disease as a strategy to mitigate health inequalities. .

Compreender o significado do capital social, diabetes tipo 2 por sexo, um contexto urbano da Colômbia. pesquisa qualitativa do interacionismo simbólico. 25 mulheres e 16 homens, diabéticos, familiares, vizinhos e cuidadores participaram seis grupos focais. 850 códigos se que foram integrados em um conjunto de 142 codes para o ego, o alter e alter ego. Três categorias e vinte subcategorias foram identificados para o projeto de "codificação de paradigma". O significado não é o mesmo para homens e mulheres. Laços sociais das redes sociais criadas diariamente pela confiança e solidariedade são valorizados cuidado diferente, porque as experiências sociais e fatos resultantes da auto-confiança, auto-eficácia e de apoio social, principalmente, auto-gestão e controle em relação a doença. Os recursos sociais de um indivíduo são reificadas para a gestão o cuidado da doença como uma estratégia para reduzir as desigualdades na saúde.

Humans , Analgesics, Opioid/chemistry , Receptors, Opioid, kappa/agonists , Acetamides/chemistry , Acetamides/pharmacology , Analgesics, Opioid/pharmacology , Arrestins/metabolism , Computer Simulation , Databases, Chemical , Diterpenes/chemistry , Diterpenes/pharmacology , Dynorphins/chemistry , Dynorphins/pharmacology , GTP-Binding Proteins/metabolism , High-Throughput Screening Assays , Ligands , Protein Transport , Receptors, Opioid, kappa/chemistry , Receptors, Opioid, kappa/metabolism , Signal Transduction , Structure-Activity Relationship
Rev. paul. pediatr ; 33(1): 82-87, Jan-Mar/2015. tab, graf
Article in English | LILACS | ID: lil-744697


OBJECTIVE: Investigate the relationship of the tumor volume after preoperative chemotherapy (TVAPQ) and before preoperative chemotherapy (TVBPQ) with overall survival at two and at five years, and lifetime. METHODS: Our sample consisted of consecutive patients evaluated in the period from 1989 to 2009 in an Onco-Hematology Service. Clinical, histological and volumetric data were collected from the medical records. For analysis, chi-square, Kaplan-Meier, log-rank and Cox regression tests were used. RESULTS: The sample consisted of 32 patients, 53.1% were male with a median age at diagnosis of 43 months. There was a significant association between TVAPQ>500mL and the difference between the TVBPQ and TVAPQ (p=0.015) and histologic types of risk (p=0.008). It was also verified an association between the difference between the TVBPQ and TVAPQ and the predominant stromal tumor (p=0.037). When assessing the TVAPQ of all patients, without a cutoff, there was an association of the variable with lifetime (p=0.013), i.e., for each increase of 10mL in TVAPQ there was an average increase of 2% in the risk of death. CONCLUSIONS: Although our results indicate that the TVAPQ could be considered alone as a predictor of poor prognosis regardless of the cutoff suggested in the literature, more studies are needed to replace the histology and staging by tumor size as best prognostic variable. .

OBJETIVO: Investigar a relação entre o volume do tumor após a quimioterapia pré-operatória (VTPOS) e antes da quimioterapia pré-operatória (VTPRE) com sobrevida geral aos dois e cinco anos e tempo de vida. MÉTODOS: A amostra foi composta por pacientes consecutivos avaliados de 1989 a 2009, em um serviço de onco-hematologia. Os dados clínicos, histológicos e volumétricos foram coletados a partir dos registros médicos. Para análise, usaram-se os testes qui-quadrado, Kaplan-Meier, log-rank e regressão de Cox. RESULTADOS: A amostra foi composta de 32 pacientes, 53,1% do sexo masculino, com mediana de idade ao diagnóstico de 43 meses. Houve associação significativa entre VTPOS >500 mL e a diferença entre o VTPRE e VTPOS (p=0,015) e os tipos histológicos de risco (p=0,008). Verificou-se também uma associação entre a diferença entre o VTPRE e VTPOS e o tumor de predomínio estromal (p=0,037). Quando se avaliou o VTPOS de todos os pacientes, sem um ponto de corte definido, observou-se associação dessa variável com o tempo de vida (p=0,013), isto é, para cada aumento de 10 mL no VTPOS houve um aumento médio de 2% no risco de morte. CONCLUSÕES: Embora os resultados indiquem que o VTPOS poderia ser considerado um preditor isolado de mau prognóstico, independentemente do ponto de corte sugerido na literatura, mais estudos são necessários para substituir a histologia e estadiamento pelo tamanho do tumor como melhor variável prognóstica. .

Animals , Humans , Mice , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes/pharmacology , Drug Resistance, Multiple/drug effects , Drug Resistance, Neoplasm/drug effects , Macrocyclic Compounds/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Proliferation/drug effects , Diterpenes/chemistry , Diterpenes/isolation & purification , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Euphorbia/chemistry , Macrocyclic Compounds/chemistry , Macrocyclic Compounds/isolation & purification , Molecular Conformation , Phenotype , Structure-Activity Relationship , Tumor Cells, Cultured
Rev. méd. Chile ; 143(1): 14-21, ene. 2015. ilus, tab
Article in Spanish | LILACS | ID: lil-742546


Background: Domperidone is widely prescribed in patients with gastrointestinal disorders but some cardiac adverse effects have been recently reported. Aim: To evaluate the risk of QT prolongation, ventricular arrhythmias and sudden cardiac death associated with the use of oral domperidone in adults without cancer. Material and Methods: Systematic searches in MEDLINE, LILACS, SciELO, the Cochrane Library and regulatory agencies websites were performed, followed by a manual search of cited references. The search strategy consisted of combining free and indexed text words without any date or language restriction. Results: Three case-control studies met the inclusion criteria; none of them evaluated QT interval prolongation. With low risk of bias, each study quantified the risk of ventricular arrhythmia or sudden cardiac death (VA/SCD). The odds ratios for these events in these studies were 4.7 (95% confidence interval (CI): 1.4-16), 1.59 (95% CI: 1.28-1.98) and 11.02 (95% CI: 2.02-62.3) respectively. A significantly increased risk was observed in patients older than 60 years of age or receiving doses > 30 mg/day. Conclusions: Heterogeneity between selected studies did not allow the computation of a summary measure. However, evidence was found that an increased risk of VA/SCD is associated with the use of oral domperidone in adults.

Animals , Female , Humans , Mice , Antineoplastic Combined Chemotherapy Protocols/therapeutic use , Breast Neoplasms/drug therapy , Diterpenes/administration & dosage , Epoxy Compounds/administration & dosage , Paclitaxel/administration & dosage , Antineoplastic Combined Chemotherapy Protocols/chemistry , Apoptosis/drug effects , Breast Neoplasms/genetics , Breast Neoplasms/metabolism , Breast Neoplasms/pathology , Cell Line, Tumor , Diterpenes/chemistry , Drug Synergism , Epoxy Compounds/chemistry , Lactones/administration & dosage , Lactones/chemistry , Mice, Nude , Oxidative Stress/drug effects , Poly(ADP-ribose) Polymerases/genetics , Poly(ADP-ribose) Polymerases/metabolism , Reactive Oxygen Species/metabolism , Structure-Activity Relationship , Transcriptional Activation/drug effects , Tumor Burden , Xenograft Model Antitumor Assays
Bol. latinoam. Caribe plantas med. aromát ; 13(1): 31-37, ene. 2014. ilus, tab
Article in English | LILACS | ID: lil-726601


Two compounds from the hexane extract of seeds of Byrsonima crassifolia were isolated and their structures elucidated using extensive spectroscopic analyses. These compounds are derived from the new labdane diterpene Labda-17-(1) and the known antimicrobial Labda-8 (17)-(2). The present study was aimed to study the effect antimicrobial of novel diterpene 1 against bacterial pathogens showed a moderate activity with MIC values 18.79-70.12 ug/ml and a MBC ranging between 250-1000 ug/ml against all assayed microorganisms.

Se aislaron dos compuestos del extracto de hexano de semillas de Byrsonima crassifolia y sus estructuras se dilucidaron por medio de extensos análisis espectroscópicos. Estos compuestos derivados del labdano corresponden al nuevo diterpeno Labda-17- (1) y el conocido antimicrobiano Labda-8(17)-(2). En el presente estudio se estudió el efecto antimicrobiano del nuevo diterpeno 1 sobre algunas bacterias patógenas mostrando sobre de estas una actividad moderada, con valores de MIC de 18.79-70.12 ug/ml y un rango de MBC que oscila entre 250-1000 ug/ml frente a todos los microorganismos ensayados.

Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Diterpenes/chemistry , Plant Extracts/pharmacology , Malpighiaceae/chemistry , Seeds , Gram-Negative Bacteria , Gram-Positive Bacteria , Diterpenes/isolation & purification , Microbial Sensitivity Tests
Bol. latinoam. Caribe plantas med. aromát ; 11(6): 520-525, nov. 2012. ilus, tab
Article in English | LILACS | ID: lil-723582


The family Trimusculidae produces labdane diterpenes, which differ in the degree and type of esterification with acetoxy and isovaleroyl ester predominantly. Here we describe the isolation from the marine pulmonate Trimusculus peruvianus, collected on intertidal rocks of Chilean coasts, of a new diterpene closely related to the above mentioned characteristics. It structure was determined by spectroscopic data. The compounds were subjected to toxicity tests using nauplii and cysts of Artemia salina. The known compounds isolated in this study have shown an ability to inhibit egg hatch of A. salina.

La familia Trimusculidae produce diterpenos tipo labdano, que difieren en el grado y tipo de esterificación con esteres acetato e isovalérico predominantemente. En este trabajo describimos el aislamiento de un nuevo diterpeno con las características ya mencionadas y de otros ya conocidos desde el molusco marino pulmonado Trimusculus peruvianus, recolectado en la zona intermareal del litoral chileno. Su estructura fue determinada a través de métodos espectroscopicos. Los compuestos fueron sometidos a ensayos de toxicidad y eclosión de los huevos de Artemia salina.

Animals , Diterpenes/isolation & purification , Diterpenes/chemistry , Mollusca/chemistry , Chile , Esterification
An. acad. bras. ciênc ; 82(4): 823-831, Dec. 2010. tab
Article in English | LILACS | ID: lil-567792


A recent reinvestigation of aerial parts of Wedelia paludosa D.C. is described and reports, for the first time, the isolation of iso-kaurenoic acid from this species.

Uma recente reinvestigação das partes aéreas de Wedelia paludosa D.C. é descrita e relata, pela primeira vez, o isolamento do ácido iso-caurenóico desta espécie.

Diterpenes/isolation & purification , Plant Extracts/isolation & purification , Wedelia/chemistry , Diterpenes/chemistry , Diterpenes/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology
Rev. Inst. Med. Trop. Säo Paulo ; 50(1): 26-28, Jan.-Feb. 2008. ilus, tab
Article in English | LILACS | ID: lil-476759


The objective of this study was to evaluate the larvicidal activity of diterpenoids obtained from the oil-resin of Copaifera reticulata against Aedes aegypti larvae, the principal vector of dengue and urban yellow fever. Four diterpenes were obtained from oil-resin extraction with organic solvents and subsequent chromatographic and spectroscopic procedures allowed to isolation and identification of these compounds as 3-b-acetoxylabdan-8(17)-13-dien-15-oic acid (1), alepterolic acid (2), 3-b-hidroxylabdan-8(17)-en-15-oic acid (3), and ent-agatic acid (4). Each compound was previously dissolved in dimethylsulphoxide, and distilled water was added to obtain the desired concentrations. Twenty larvae of third instars were placed into plastic beckers, containing the solution test (25 mL), in a five repetitions scheme, and their mortality, indicated by torpor and darkening of the cephalic capsule, was recorded after 48h. Probit analyses were used to determine lethal concentrations (LC50 and LC90) and their respective 95 percent confidence intervals. This study showed that only diterpenoids 1 and 2 exhibited larvicidal properties with LC50 of 0.8 ppm and 87.3 ppm, respectively, revealing the former as the most toxic compound against third instars of Ae. aegypti. Therefore, this compound seems to be an interesting source for new metabolite to be exploited.

O objetivo deste trabalho foi avaliar a atividade larvicida de diterpenos isolados do óleo-resina de Copaifera reticulata sobre Aedes aegypti, principal vetor de dengue e febre amarela urbana. Quatro diterpenóides foram obtidos a partir da extração do óleo-resina com solventes orgânicos e, subseqüentes procedimentos cromatográficos e espectroscópicos permitiram o isolamento e a identificação desses compostos como ácido 3-b-acetoxylabdan-8(17)-13-dien-15-óico (1), ácido alepterólico (2), ácido 3-b-hidroxylabdan-8(17)-en-15-óico (3) e ácido ent-agático (4). Cada um desses compostos foi previamente solubilizado em dimetilsulfóxido, acrescentando-se água, até se obterem as concentrações desejadas. Em cada bioensaio foram utilizadas 20 larvas de 3° estádio de Ae. aegypti colocadas em 25 mL da solução-teste. Foram feitas cinco repetições, e a mortalidade avaliada 48 h após a exposição, indicada pela ausência de movimentos e escurecimento da cápsula cefálica. Os dados obtidos da mortalidade x concentração (ppm) foram analisados, em gráfico de Probit para avaliar as concentrações letais (CL50 e CL90). Este estudo revelou que os diterpenóides 1 e 2 mostraram atividade larvicida com CL50 de 0,8 e 87,3 ppm, respectivamente, sendo o diterpeno 1 o composto mais promissor a ser usado como larvicida para o controle de Ae. aegypti.

Animals , Aedes , Balsams/chemistry , Diterpenes/isolation & purification , Insecticides , Diterpenes/chemistry , Larva/drug effects
An. acad. bras. ciênc ; 78(1): 17-21, Mar. 2006. tab
Article in English | LILACS | ID: lil-422257


O estudo fitoquímico de Salzmmania nitida D.C. (Rubiaceae) conduziu ao isolamento e identificação de dois novos terpenoides, (+)-3-oxo-thermarol e 11-acetoxi-4alfa-metil-5alfa-eudesmanol além do (+)-termarol. As estruturas foram estabelecidas com base na análise de espectros de IV, Massas e RMN de 1H e 13C (1D e 2D).

Abietanes/chemistry , Diterpenes/chemistry , Rubiaceae/chemistry , Sesquiterpenes, Eudesmane/chemistry , Abietanes/isolation & purification , Diterpenes/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Structure , Sesquiterpenes, Eudesmane/isolation & purification
Electron. j. biotechnol ; 8(3)Dec. 2005.
Article in English | LILACS | ID: lil-448793


Grindelia pulchella callus and cell suspension cultures were established from seedling leaves. When several phytoregulator supplementations were assayed in solid Murashige and Skoog medium containing 3 percent (w/v) of sucrose (MS medium), combinations of indole-3-butyric acid (IBA) and N6-benzylaminopurine (BA) resulted the most appropriate conditions to generate fast growing friable calli with detectable levels of grindelic acid. Moreover, the same basal media supplemented with 20.0 µM IBA/4.4 µM BA was found to be optimal for cell growth in submerged cultures (µmax = 0.26 days-1) while the addition of 20.0 µM IBA/18.0 µM BA resulted in a relative higher metabolite production (4.55 mg/gDW) when the inocula was 5 percent (v/v). Furthermore, three different stress factors and combinations of them were used to elicit cell suspensions. These experiments demonstrated that the combination of CuSO4 and dimethylsulfoxide (DMSO) increase the grindelic acid production to 2.63 mg/gDW in the elicited essay versus 0.756 mg/gDW in the control, at expense of cell growth. In contrast, the addition of jasmonic acid (JA) alone and combined with DMSO neither affected cell growth nor grindelic acid accumulation.

Cyclopentanes/metabolism , Dimethyl Sulfoxide/metabolism , Diterpenes/chemistry , Copper Sulfate/metabolism , Fatty Acids, Unsaturated/metabolism , Cells, Cultured , Diterpenes/isolation & purification
Rev. Soc. Bras. Med. Trop ; 37(supl.2): 96-97, 2004. ilus
Article in English | LILACS | ID: lil-723328


Clinical and experimental studies have consistently incriminated the medicinal plant germander (Teucrium chamaedrys L.) in epidemic and sporadic cases of liver diseases. The sacaca (Croton cajucara Benth), a common plant in Brazilian Amazon region also comes being incriminated in similar clinical cases. Of both plants were isolated diterpenoid coumpounds with similar chemical structures.

Estudos clínicos e experimentais tem incriminado, de forma consistente, na França, a planta medicinal germander (Teucrium chamaedrys L.) em casos esporádicos ou epidêmicos de hepatopatias. A Sacaca (Croton cajucara Benth), uma planta comum na Amazônia brasileira, também vem sendo incriminada em casos clínicos semelhantes. De ambas as plantas, foram isolados diterpenóides com estruturas químicas semelhantes.

Humans , Croton/toxicity , Diterpenes/isolation & purification , Chemical and Drug Induced Liver Injury/etiology , Teucrium/toxicity , Croton/chemistry , Diterpenes/chemistry , Diterpenes/toxicity , Teucrium/chemistry
Braz. j. microbiol ; 31(2): 83-6, Apr.-Jun. 2000. ilus, tab, graf
Article in English | LILACS | ID: lil-297641


Parameters for a more effcient biotransformation of diterpene-like compounds by the fungus "Cephalosporium aphidicola" were established by carrying out microscale feeding at several conditions. Experiments were guided by thin layer chromatography and gas chromatography analysis. It was observed that the substrate should be added in ethanol at concentrations between 15 to 14 mg per 100 ml of medium. The extraction of the product showed to be more effcient when carried out from both mycelia and broth and using ethylacetate as the extracting solvent. The experiment should be stopped six days after feeding the substrate to the fungus for the best product yield.

Acremonium/enzymology , Biotransformation , Diterpenes/chemistry , In Vitro Techniques , Chromatography, Gas , Chromatography, Thin Layer , Incubators/standards