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1.
Chemistry ; 30(62): e202402426, 2024 Nov 07.
Artículo en Inglés | MEDLINE | ID: mdl-39158373

RESUMEN

Herein, we report the synthesis of seleno-substituted chromenes from selenoalkynes and phenols. In this cascade reaction, the applied gold catalyst not only functions as a π-acid, but also as a Lewis acid, enabling the propargylic substitution in the first step to connect the oxygen carbon bond. Under the optimal reaction condition a total of 26 chromenes were accessible by this modular access. During scale up experiments, the hydrolysis of the vinylselenium substructure to the corresponding chromenones was observed. By revisiting the electron-rich starting materials, four chromenones were produced following a one-pot reaction using a single gold catalyst. To better understand the interaction of gold and selenium, a series of nuclear magnetic resonance studies and high-resolution mass spectrometry studies were performed, which led to the proposal of a mechanism for this transformation.

2.
Exp Appl Acarol ; 91(4): 697-714, 2023 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-37985606

RESUMEN

Rhipicephalus sanguineus sensu lato 'tropical lineage' (Acari: Ixodidae) is considered a sanitary concern due to its role as a disease vector. Tick strains resistant to synthetic acaricides have caused difficulties in their control, besides synthetic acaricides are harmful to the environment and to the health of non-target animals. The research of plants with acaricidal and repellent properties has proved to be an efficient alternative in tick control. The genus Tagetes spp. excels for its use as traditional pest control in households and plantations and also for its potential as an acaricide against R. sanguineus under laboratory conditions. The first aim of the present study was to evaluate the effect of different doses of Tagetes minuta essential oil (TMEO) on the central nervous system (synganglion) in unfed R. sanguineus adults. The histological analysis of synganglion exposed to the different concentrations of TMEO and amitraz 12.5% (50% of the recommended dose in the package insert) showed a significant effect with signs of cell damage including volume increase, loss of shape, and vacuolization, in addition to chromatin alterations such as condensation, margination, and fragmentation. TMEO were analyzed by gas chromatography coupled with mass spectrometry showing the presence of 21 compounds that according to their chemical structure are classified as terpenoids. Among them (Z)-ß-ocimene, ocimene, (Z)-tagetone, and verbenone were found in major quantities.


Asunto(s)
Acaricidas , Aceites Volátiles , Rhipicephalus sanguineus , Tagetes , Animales , Rhipicephalus sanguineus/fisiología , Aceites Volátiles/farmacología , Aceites Volátiles/química , Acaricidas/farmacología , Tagetes/química , Sistema Nervioso Central
3.
J Org Chem ; 87(22): 15050-15060, 2022 11 18.
Artículo en Inglés | MEDLINE | ID: mdl-36302502

RESUMEN

We describe here for the first time the synthesis of 2-(chalcogenyl)-3H-benzo[f]chromenes and the new 3-(phenylselanyl)-2H-chromenes by the radical or electrophilic cyclization of propargylic aryl ethers in the presence of diorganyl diselenides or ditellurides using Oxone as a green oxidant and acetonitrile as solvent in a sealed tube at 100 °C. In this study, thirty-one chalcogenylchromenes with a broad substrate scope were prepared in moderate to excellent yields (50-98%), including compounds derived from natural products.


Asunto(s)
Benzopiranos , Éteres , Ciclización , Estructura Molecular , Éteres/química , Benzopiranos/química
4.
J Org Chem ; 86(20): 14016-14027, 2021 10 15.
Artículo en Inglés | MEDLINE | ID: mdl-33750133

RESUMEN

A new method was developed for the synthesis of 4-chalcogenyl-1H-isochromen-1-ones through the 6-endo-dig electrophilic cyclization of 2-alkynylaryl esters and diorganyl dichalcogenides under ultrasound irradiation. The reactions were performed under mild conditions, using Oxone as a green oxidant to promote the cleavage of the chalcogen-chalcogen bond in diorganyl diselenides and ditellurides to generate electrophilic species in situ. A total of 25 compounds were selectively obtained after 30-70 min, in good to excellent yields (74-95%). This procedure was extended to prepare 5H-selenopheno[3,2-c]isochromen-5-ones. Additionally, for the first time, the 4-chalcogenyl-1H-isochromen-1-ones were used as substrates in the thionation reaction, using Lawesson's reagent and microwave irradiation under solvent-free conditions, obtaining the thio derivatives in yields of up to 99% in only 15 min.


Asunto(s)
Estructura Molecular , Catálisis , Ciclización , Solventes , Ácidos Sulfúricos
5.
Beilstein J Org Chem ; 17: 234-244, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-33564334

RESUMEN

We described herein a selective method to prepare α-organylthio esters and α-organylthio ketones by the reaction of ß-keto esters with sodium S-benzyl sulfurothioate or sodium S-alkyl sulfurothioate (Bunte salts) under basic conditions in toluene as the solvent at 100 °C. When 4 equivalents of a base were used, a series of differently substituted α-thio esters were obtained with up to 90% yield. On the other hand, employing 2 equivalents of a base, α-thio ketones were achieved after 18 h under air. Furthermore, after a shorter reaction time, the isolation of keto-enol tautomers was possible, revealing them as significant intermediates for the mechanism elucidation.

6.
J Org Chem ; 84(9): 5471-5482, 2019 05 03.
Artículo en Inglés | MEDLINE | ID: mdl-31020836

RESUMEN

A simple method for the direct mono- and bis-organylselenylation of N-substituted pyrroles through a multicomponent reaction promoted by ultrasonic radiation was described. These sonochemical promoted reactions were performed between different primary amines, 2,5-hexanedione and dialkyl, diheteroaryl, or diaryl diselenides, using catalytic amounts of copper iodide. Depending on the amount of copper iodide and diorganyl diselenide used in the reactions, mono- or bis-organylselenylation products were efficiently synthesized in high yields.

7.
J Org Chem ; 84(19): 12452-12462, 2019 10 04.
Artículo en Inglés | MEDLINE | ID: mdl-31509698

RESUMEN

Herein, we describe a new strategy to prepare chalcogen-functionalized isoxazolines. The strategy involves the reaction of ß,γ-unsaturated oximes with electrophilic selenium and tellurium species, affording 19 new selenium- and tellurium-containing isoxazolines in good yields after 1 h at room temperature. The method was efficiently extended to the synthesis of 5 new (bis)isoxazoline ditellurides. One of the prepared compounds, 3-phenyl-5-((phenylselanyl)methyl)-isoxazoline, demonstrated better anti-inflammatory and antiedematogenic effects than the reference drug Celecoxib.


Asunto(s)
Antiinflamatorios no Esteroideos/uso terapéutico , Edema/tratamiento farmacológico , Isoxazoles/uso terapéutico , Oximas/uso terapéutico , Animales , Antiinflamatorios no Esteroideos/síntesis química , Antiinflamatorios no Esteroideos/química , Aceite de Crotón , Relación Dosis-Respuesta a Droga , Oído , Edema/inducido químicamente , Isoxazoles/síntesis química , Isoxazoles/química , Masculino , Ratones , Estructura Molecular , Oximas/química
8.
Chemistry ; 23(55): 13760-13765, 2017 Oct 04.
Artículo en Inglés | MEDLINE | ID: mdl-28763120

RESUMEN

The retro-Favorskii reaction is an excellent way to achieve terminal alkynes. Methodologies that connect the synthesis of terminal alkynes and organochalcogen motifs are important for the construction of novel compounds. Fourteen new terminal alkynes containing either Csp -S or Csp -Se bonds were selectively prepared through the retro-Favorskii reaction from the respective carbinol precursors. It was discovered that terminal chalcogen alkynes were stable for weeks if stored as a solution in hexanes.

9.
Beilstein J Org Chem ; 13: 694-702, 2017.
Artículo en Inglés | MEDLINE | ID: mdl-28503204

RESUMEN

The use of sonochemistry is described in the organocatalytic enamine-azide [3 + 2] cycloaddition between 1,3-diketones and aryl azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl azidophenyl selenides, providing an efficient access to new ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones in good to excellent yields and short reaction times. In addition, this protocol was extended to ß-keto esters, ß-keto amides and α-cyano ketones. Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very mild reaction conditions.

10.
An Acad Bras Cienc ; 88(1): 281-92, 2016 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-26839997

RESUMEN

Salvia officinalis (Lamiaceae) has been used in south of Brazil as a diary homemade, in food condiment and tea-beverage used for the treatment of several disorders. The objective of this study was to characterize chemical compounds in the hydroalcoholic (ExtHS) and aqueous (ExtAS) extract from Salvia officinalis (L.) by gas chromatography-mass spectrometry (GC-MS) and by high-resolution electrospray ionization mass spectrometry (ESI-QTOF MS/MS), evaluate in vitro ability to scavenge the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH•) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+), catalase (CAT-like) and superoxide dismutase (SOD-like) activity, moreover cytotoxic by MTT assay, alterations on cell morphology by giemsa and apoptotic-induced mechanism for annexin V/propidium iodide. Chemical identification sage extracts revealed the presence of acids and phenolic compounds. In vitro antioxidant analysis for both extracts indicated promising activities. The cytotoxic assays using tumor (Hep-2, HeLa, A-549, HT-29 and A-375) and in non-tumor (HEK-293 and MRC-5), showed selectivity for tumor cell lines. Immunocytochemistry presenting a majority of tumor cells at late stages of the apoptotic process and necrosis. Given the results presented here, Brazilian Salvia officinalis (L.) used as condiment and tea, may protect the body against some disease, in particularly those where oxidative stress is involved, like neurodegenerative disorders, inflammation and cancer.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Antioxidantes/farmacología , Extractos Vegetales/farmacología , Salvia officinalis/química , Línea Celular Tumoral/efectos de los fármacos , Proliferación Celular , Cromatografía de Gases y Espectrometría de Masas , Humanos , Inmunohistoquímica , Estrés Oxidativo/efectos de los fármacos
11.
Pharmaceuticals (Basel) ; 17(7)2024 Jul 17.
Artículo en Inglés | MEDLINE | ID: mdl-39065804

RESUMEN

A new series of compounds planned by molecular hybridization of the nucleobases uracil and thymine, or the xanthine theobromine, with coumarins, and linked through 1,2,3-triazole heterocycles were evaluated for their in vitro anticancer activity against the human tumor cell lines: colon carcinoma (HCT116), laryngeal tumor cells (Hep-2), and lung carcinoma cells (A549). The hybrid compound 9a exhibited better activity in the series, showing an IC50 of 24.19 ± 1.39 µM against the HCT116 cells, with a selectivity index (SI) of 6, when compared to the cytotoxicity against the non-tumor cell line HaCat. The in silico search for pharmacological targets was achieved through molecular docking studies on all active compounds, which suggested that the synthesized compounds possess a high affinity to the Topoisomerase 1-DNA complex, supporting their antitumor activity. The in silico toxicity prediction studies suggest that the compounds present a low risk of causing theoretical mutagenic and tumorigenic effects. These findings indicate that molecular hybridization from natural derivative molecules is an interesting approach to seek new antitumor candidates.

12.
J Org Chem ; 78(8): 4123-31, 2013 Apr 19.
Artículo en Inglés | MEDLINE | ID: mdl-23570264

RESUMEN

A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not require the use of a large excess of organometallic reagent. Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated.


Asunto(s)
Acetamidas/química , Ácidos Borónicos/química , Cloroacetatos/química , Compuestos Heterocíclicos/síntesis química , Indicadores y Reactivos/química , Paladio/química , Sales (Química)/química , Catálisis , Ésteres , Compuestos Heterocíclicos/química , Estructura Molecular , Temperatura
13.
Chem Asian J ; 17(8): e202101394, 2022 Apr 14.
Artículo en Inglés | MEDLINE | ID: mdl-35294794

RESUMEN

A metal- and catalyst-free photo-promoted cyclization of properly substituted vinyl selenides was developed using UVA irradiation. A total of eighteen new C3-unsubstituted 2-selanyl benzochalcogenophenes (benzofurans, benzothiophenes and benzoselenophenes) were prepared in 30-86% yield after irradiation with UVA at room temperature. The usefulness of the title compounds was demonstrated in the easy functionalization of the remaining free C-H bond of the benzochalcogenophenes to form new C-Se and C-Br bonds by simple procedures. Furthermore, the reaction can be performed under natural sunlight irradiation and the solvent is easily reused further in several subsequent runs.


Asunto(s)
Benzofuranos , Rayos Ultravioleta , Catálisis , Ciclización , Solventes
14.
Ultrason Sonochem ; 67: 105165, 2020 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-32416574

RESUMEN

Ultrasound-assisted approach was successfully applied for the synthesis of mayenite from calcium and aluminum hydroxides and then subsequently impregnated with Ni by the wet impregnation method. The synthesis was performed with a 13 mm probe-type ultrasound, operating under an acoustic power of 30.5 W and a frequency of 20 kHz. Ultrasound application was studied in detail from a 3k experimental design, where the variables studied were ultrasound time (10-50 min) and calcination temperature (900-1200 °C). Ultrasound promoted an effective dispersion of the precursors in a short time of 10 min leading to a high conversion to mayenite after calcination at 1200 °C. Ultrasound treatment also had a positive effect on Ni impregnation, increasing the dispersion of the metal in the support and leading to a stronger interaction of nickel-containing species with mayenite support. The use of ultrasound application has proved to be attractive both for catalyst properties and for facilitating catalyst synthesis.


Asunto(s)
Biomasa , Níquel/química , Sonicación , Catálisis
15.
Food Chem ; 326: 126997, 2020 Oct 01.
Artículo en Inglés | MEDLINE | ID: mdl-32422511

RESUMEN

The increased demand for pesticide-free foods has also increased the search for healthier and environmentally friendly alternatives in agriculture. Essential oils are known to possess natural antifungal properties, becoming a reliable alternative for commercial fungicides, especially for postharvest decay control. However, essential oils are volatile and photodegradable, which reduces their long-term activities. This work presents the development of a lemongrass essential oil-containing poly(lactic acid) nanocapsules. They have shown in vitro antifungal activity against Colletotrichum acutatum and Colletotrichum gloeosporioides with a MIC dosage of 0.1% (v/v) for both phytopathogens. In the in vivo assay with postharvest apples, the ones treated with encapsulated essential oil showed bitter rot lesions three times smaller than the ones treated with non-encapsulated essential oil, or in comparison to the apples in positive control. The methodology led to stable nanocapsules with spherical morphology, a mean diameter of 96.4 nm, and with an encapsulation efficiency of 99%.


Asunto(s)
Antifúngicos/farmacología , Colletotrichum/efectos de los fármacos , Cymbopogon/química , Fungicidas Industriales/farmacología , Nanocápsulas/química , Aceites Volátiles/química , Poliésteres/farmacología , Malus/efectos de los fármacos , Malus/microbiología , Poliésteres/química
16.
J Pharm Biomed Anal ; 174: 104-114, 2019 Sep 10.
Artículo en Inglés | MEDLINE | ID: mdl-31163344

RESUMEN

The bioproduction of lactobionic acid and its salts can be performed by enzymatic complex glucose-fructose oxidoreductase (GFOR) and glucono-δ-lactonase (GL) of Zymomonas mobilis. Considering the applicability of these compounds in pharmaceutical area, the aim of this study was to assess the accelerated and long-term stability studies of sodium, potassium, calcium lactobionate, and lactobionic acid. Furthermore, stress tests were performed to evaluate the stability against pH, temperature and oxidation. The samples submitted to degradation tests were analyzed by high-performance liquid chromatography (HPLC) and high-resolution mass spectrometry analysis (HRMS-ESI-QTOF). Sodium, potassium, and calcium lactobionate were stable for six months of analyses considering the accelerated (40 °C and 75% RH) and long-term (30 °C and 75% RH) stability studies. The presence of lactobiono-δ-lactone and a significant increase in moisture were observed for both biosynthesized and commercially available lactobionic acid samples. Against the forced degradation tests, all the lactobionate salts and lactobionic acid showed to be stable upon alkaline and acid pH conditions, at 60 and 80 °C, and also against UV light exposition. Furthermore, the presence of lactobiono-δ-lactone form was observed in lactobionic acid samples. However, the degradation of both lactobionic acid and lactobionate salts was evident in the presence of hydrogen peroxide. This degradation kinetic profile suggests, that lactobionate salts follows a zero-order reaction model and lactobionic acid follows a second-order kinetic. The MS analysis of the main degradation product suggests a molecular formula C11H20O10 resulting from the oxidative decarboxylation. This report brings an amount of results as contribution to the scarce information regarding the chemical and physical-chemical stability of sodium, potassium, calcium lactobionate, and lactobionic acid. These data may be useful and serve as reference, in view of the multipurpose applications of the cited compounds.


Asunto(s)
Calcio/química , Disacáridos/química , Potasio/química , Sodio/química , Zymomonas/química , Reactores Biológicos , Descarboxilación , Estabilidad de Medicamentos , Peróxido de Hidrógeno/química , Concentración de Iones de Hidrógeno , Cinética , Lactonas , Espectrometría de Masas , Estrés Oxidativo , Oxidorreductasas/química , Oxígeno/química , Temperatura , Rayos Ultravioleta
17.
Front Pediatr ; 7: 293, 2019.
Artículo en Inglés | MEDLINE | ID: mdl-31355171

RESUMEN

In human immunodeficiency virus and acquired immune deficiency syndrome (HIV/AIDS) patients with very low CD4 cell counts, there is a temporal relationship between administration of antiretroviral therapy (ART) and an increased inflammatory response state known as the immune reconstitution inflammatory syndrome (IRIS). The predominant clinical presentation of IRIS is an infectious disease that can be life-threatening. IRIS-related infectious events are distributed similarly between adult males and females, albeit a few studies have shown a skewing toward the male sex in pediatric IRIS. Here, we assessed sex-specific differences in the causes and extent of IRIS infectious events in HIV-infected pediatric patients on ART. We carried out a prospective clinical analysis (from 2000 to 2018) of IRIS-related infectious events after ART in a cohort of 82 Brazilian children and adolescents infected with HIV-1 through mother-to-child transmission as well as a comprehensive cross-referencing with public records on IRIS-related infectious causes in pediatric HIV/AIDS. Twelve events fulfilling the criteria of IRIS occurred exclusively in 11 females in our cohort. The median age at IRIS events was 3.6 years. The infectious causes included Mycobacterium bovis, varicella-zoster virus, molluscum contagiosum virus, human papillomavirus, cytomegalovirus, and Mycobacterium tuberculosis. In one female, there was regional bacillus Calmette-Guérin dissemination and cytomegalovirus esophagitis. There was complete health recovery after 10 IRIS events without the use of corticosteroids or ART interruption. One case of IRIS-associated miliary tuberculosis was fatal. The biological female sex was a significant risk factor for IRIS events (odds ratio: 23.67; 95% confidence interval 95%: 1.341-417.7; P = 0.0016 and P < 0.01 by the multivariable analysis). We observed an effect of the advanced HIV/AIDS variable in IRIS females as compared with non-IRIS females (mean CD4+ T cell percentage 13.36 vs. 18.63%; P = 0.0489 and P < 0.05 by the multivariable analysis), underpinning the exclusively skewed distribution toward the female sex of this cohort. Moreover, the IRIS females in our cohort had higher mean CD4+ T cell percentages before (13.36%) and after IRIS (26.56%) than those of the IRIS females (before IRIS, 4.978%; after IRIS, 13.81%) in previous studies conducted worldwide. The exclusively skewed distribution of pediatric IRIS toward the female sex in the cohort was not linked to preferential X-chromosome inactivation rates. We concluded that the exclusively skewed distribution of pediatric IRIS toward females is associated with more advanced AIDS.

18.
PLoS One ; 13(2): e0191797, 2018.
Artículo en Inglés | MEDLINE | ID: mdl-29390009

RESUMEN

Most studies of Brazilian red propolis have explored the composition and biological properties of its ethanolic extracts. In this work, we chemically extracted and characterized the essential oil of Brazilian red propolis (EOP) and assessed its adjuvant, antiparasitic and cytotoxic activities. The chemical composition of EOP was analyzed using gas chromatography with mass spectrometry (GC-MS). EOP was tested for in vitro activity against Trichomonas vaginalis (ATCC 30236 isolate); trophozoites were treated with different concentrations of EOP (ranging from 25 to 500 µg/mL) in order to establish the MIC and IC50 values. A cytotoxicity assay was performed in CHO-K1 cells submitted to different EOP concentrations. BALB/c mice were used to test the adjuvant effect of EOP. The animals were divided in 3 groups and inoculated as follows: 0.4 ng/kg BW EOP (G1); 50 µg of rCP40 protein (G2); or a combination of 0.4 ng/kg BW EOP and 50 µg of rCP40 (G3). Total IgG, IgG1 and IgG2a levels were assessed by ELISA. The major constituent compounds of EOP were methyl eugenol (13.1%), (E)-ß-farnesene (2.50%), and δ-amorphene (2.3%). Exposure to EOP inhibited the growth of T. vaginalis, with an IC50 value of 100 µg/mL of EOP. An EOP concentration of 500 µg/mL was able to kill 100% of the T. vaginalis trophozoites. The EOP kinetic growth curve showed a 36% decrease in trophozoite growth after a 12 h exposure to 500 µg/mL of EOP, while complete parasite death was induced at 24 h. With regard to CHO-K1 cells, the CC50 was 266 µg/mL, and 92% cytotoxicity was observed after exposure to 500 µg/mL of EOP. Otherwise, a concentration of 200 µg/mL of EOP was able to reduce parasite proliferation by 70% and was not cytotoxic to CHO-K1 cells. As an adjuvant, a synergistic effect was observed when EOP was combined with the rCP40 protein (G3) in comparison to the administration of each component alone (G1 and G2), resulting in higher concentrations of IgG, IgG1 and IgG2a. EOP is constituted by biologically active components with promising antiparasitic and immunostimulatory activities and can be investigated for the formulation of new vaccines or trichomonacidal drugs.


Asunto(s)
Adyuvantes Inmunológicos/farmacología , Antiparasitarios/farmacología , Aceites Volátiles/química , Aceites Volátiles/farmacología , Própolis/química , Animales , Formación de Anticuerpos , Células CHO , Supervivencia Celular/efectos de los fármacos , Cricetinae , Cricetulus , Femenino , Cromatografía de Gases y Espectrometría de Masas , Ratones Endogámicos BALB C , Trichomonas vaginalis/efectos de los fármacos
19.
Ultrason Sonochem ; 34: 107-114, 2017 01.
Artículo en Inglés | MEDLINE | ID: mdl-27773224

RESUMEN

We described herein the use of sonochemistry in the organocatalytic enamine-azide [3+2] cycloadditions of ß-oxo-amides with a range of substituted aryl azides. These sonochemical promoted reactions were found to be amenable to a range of ß-oxo amides or aryl azides, providing an efficient access to new N-aryl-1,2,3-triazoyl carboxamides in good to excellent yields and short times of reaction.

20.
Fitoterapia ; 114: 127-137, 2016 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-27639415

RESUMEN

The Tabernaemontana genus belongs to the family Apocynaceae comprising about 100 species spread throughout tropical and subtropical regions around the world including Brazil, which contains around 40 species spread all over its territory. Because of the territorial space and climate diversity, these species already identified in Brazil are the largest collection of Tabernaemontana, which are representative (about 30%) of worldwide distribution. The monoterpene indole alkaloids present as major secondary components in all parts of the plants of the genus Tabernaemontana, have attracted the attention of the scientific community for new alkaloids derivatives and bioactivities. This review covers relevant references about Tabernaemontana species found in Brazil, its geographical distribution, occurrence of monoterpene alkaloids and phytochemical activities. Additional information about the South American species activities are also reported in this review.


Asunto(s)
Alcaloides Indólicos/farmacología , Monoterpenos/farmacología , Fitoquímicos/farmacología , Tabernaemontana/química , Brasil , Extractos Vegetales/farmacología , Tabernaemontana/clasificación
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