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1.
Chem Biodivers ; 21(7): e202400388, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38739854

RESUMO

Myrtaceae family includes many species with taxonomic challenges, making it one of the most complex families to identify. This study used DNA barcoding to find molecular markers for species authentication based on the Myrtaceae family's chemical composition and genetic diversity. Essential oils and genetic material were extracted from the leaves of six different species: Eugenia uniflora, E. patrisii, Myrcia splendens, Psidium guajava, P. guineense, and Psidium sp. The samples were analyzed based on compound classes and grouped into two categories. Group I included samples with high amounts of oxygenated sesquiterpenes (3.69-76.05 %) and fatty acid derivatives (0.04-43.59 %), such as E. uniflora, Myrcia splendens, and E. patrisii. Group II included samples P. guajava, P. guineense, and Psidium sp., which had a significant content of monoterpene hydrocarbons (0.69-72.35 %), oxygenated sesquiterpenes (8.06-68.1 %), phenylpropanoids (0.45-22.59 %), and sesquiterpene hydrocarbons (0.27-21.84 %). The PsbA-trnH gene sequences had a high genetic variability, allowing the species to be distinguished. A phylogenetic analysis showed two main clusters with high Bootstrap values corresponding to the subtribes Eugeniineae, Myrciinae, and Pimentinae. The results suggest a weak correlation between genetic and chemical data in these Myrtaceae species.


Assuntos
Código de Barras de DNA Taxonômico , Myrtaceae , Óleos Voláteis , Brasil , Óleos Voláteis/química , Myrtaceae/química , Myrtaceae/genética , Folhas de Planta/química , DNA de Plantas/genética
2.
Chem Biodivers ; : e202401161, 2024 Jul 27.
Artigo em Inglês | MEDLINE | ID: mdl-39073007

RESUMO

In this study, essential oils and waste hydrosols of leaves of Ocimum tenuiflorum in four different geographical locations were extracted by hydrodistillation method and using gas chromatography/mass spectrometry (GC/MS) for chemical composition analysis. All four essential oil samples contained the main components (E)-ß-caryophyllene (27.8-49.0 %), trans-ß-elemene (20.3-37.1 %) and eugenol (9.0-44.0 %). Three of the four hydrosol samples had eugenol in absolute content (94.5-98.6 %), while the remaining hydrosol sample had two main components, elemicin (77.8 %) and eugenol (14.2 %). Essential oils and hydrosols demonstrated larvicidal activities against four important disease-transmitting mosquito species including Aedes aegypti, Aedes albopictus, Culex quinquefasciatus, and Culex fuscocephala with 24-h LC50 values in the range 15.42-56.01 µg/mL and 53.88-97.80 µg/mL for the essential oils and the hydrosols, respectively. Essential oils and hydrosols strongly inhibited the acetylcholinesterase (AChE) enzyme of electric eels with IC50 values in the range of 25.35-107.19 µg/mL. Microemulsion (ME) can be considered as a sustainable pesticide formulation over 300 days and has improved larvicidal activity compared to free essential oil. The O. tenuiflorum in Vietnam can be considered a low-cost source of eugenol, botanical pesticides that control disease-transmitting mosquitoes, as well as having therapeutic potential to be further investigated.

3.
Molecules ; 29(6)2024 Mar 20.
Artigo em Inglês | MEDLINE | ID: mdl-38543021

RESUMO

As part of our interest in the volatile phytoconstituents of aromatic plants of the Great Basin, we have obtained essential oils of Ambrosia acanthicarpa (three samples), Artemisia ludoviciana (12 samples), and Gutierrezia sarothrae (six samples) from the Owyhee Mountains of southwestern Idaho. Gas chromatographic analyses (GC-MS, GC-FID, and chiral GC-MS) were carried out on each essential oil sample. The essential oils of A. acanthicarpa were dominated by monoterpene hydrocarbons, including α-pinene (36.7-45.1%), myrcene (21.6-25.5%), and ß-phellandrene (4.9-7.0%). Monoterpene hydrocarbons also dominated the essential oils of G. sarothrae, with ß-pinene (0.5-18.4%), α-phellandrene (2.2-11.8%), limonene (1.4-25.4%), and (Z)-ß-ocimene (18.8-39.4%) as major components. The essential oils of A. ludoviciana showed wide variation in composition, but the relatively abundant compounds were camphor (0.1-61.9%, average 14.1%), 1,8-cineole (0.1-50.8%, average 11.1%), (E)-nerolidol (0.0-41.0%, average 6.8%), and artemisia ketone (0.0-46.1%, average 5.1%). This is the first report on the essential oil composition of A. acanthicarpa and the first report on the enantiomeric distribution in an Ambrosia species. The essential oil compositions of A. ludoviciana and G. sarothrae showed wide variation in composition in this study and compared with previous studies, likely due to subspecies variation.


Assuntos
Artemisia , Óleos Voláteis , Óleos Voláteis/química , Artemisia/química , Ambrosia , Idaho , Monoterpenos/análise
4.
Molecules ; 29(8)2024 Apr 18.
Artigo em Inglês | MEDLINE | ID: mdl-38675665

RESUMO

In the search for new bioactive agents against the infectious pathogen responsible for the neglected tropical disease (NTD) mycetoma, we tested a collection of 27 essential oils (EOs) in vitro against Madurella mycetomatis, the primary pathogen responsible for the fungal form of mycetoma, termed eumycetoma. Among this series, the EO of Santalum album (Santalaceae), i.e., East Indian sandalwood oil, stood out prominently with the most potent inhibition in vitro. We, therefore, directed our research toward 15 EOs of Santalum species of different geographical origins, along with two samples of EOs from other plant species often commercialized as "sandalwood oils". Most of these EOs displayed similar strong activity against M. mycetomatis in vitro. All tested oils were thoroughly analyzed by GC-QTOF MS and most of their constituents were identified. Separation of the sandalwood oil into the fractions of sesquiterpene hydrocarbons and alcohols showed that its activity is associated with the sesquiterpene alcohols. The major constituents, the sesquiterpene alcohols (Z)-α- and (Z)-ß-santalol were isolated from the S. album oil by column chromatography on AgNO3-coated silica. They were tested as isolated compounds against the fungus, and (Z)-α-santalol was about two times more active than the ß-isomer.


Assuntos
Madurella , Micetoma , Óleos Voláteis , Óleos de Plantas , Santalum , Sesquiterpenos , Madurella/efeitos dos fármacos , Óleos de Plantas/farmacologia , Óleos de Plantas/química , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Micetoma/microbiologia , Micetoma/tratamento farmacológico , Santalum/química , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Antifúngicos/farmacologia , Antifúngicos/química , Testes de Sensibilidade Microbiana
5.
Inflammopharmacology ; 32(5): 3375-3388, 2024 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-39039347

RESUMO

Ayapana triplinervis (M.Vahl) R.M.King & H.Rob. (Asteraceae), popularly known as japana, is a tropical, aromatic subshrub widely used as tea to combat some diseases. The essential oil was obtained from the leaves by hydrodistillation (3 h), and the chemical composition was analyzed by gas chromatography coupled to mass spectrometry. For in vivo assays, Mus musculus/Swiss mice were used to evaluate oral acute toxicological (at dose of 2000 mg/kg); peripheral and central analgesic for abdominal contortion (doses of 6.25, 12.5, 25, 50 and 100 mg/kg), hot plate test (12.5, 25, 50, and 100 mg/kg) and formalin (25, 50 and 100 mg/kg); open field test (100 mg/kg); and anti-inflammatory by ear swelling induced by xylene (6.25,12.5, 25, 50, and 100 mg/kg). The yield of A. triplinervis essential oil (AtEO) was 4.6%, and the oxygenated monoterpene 2,5-dimethoxy-p-cymene was the major compound in this study (63.6%). AtEO at a dose of 2,000 mg/kg orally did not change the behavior patterns or mortality of the animals; liver and kidney biochemical levels were similar to the control group, indicating no liver and kidney toxicity. Moreover, AtEO, at doses of 6.25, 12.5, 25, 50, and 100 mg/kg, reduced abdominal contortions by 21%, 54%, 91%, 58%, and 55%, respectively. In the hot plate test, AtEO showed a significant increase in latency time in the 60-min interval at doses of 25 mg/kg (11.3 ± 3.3 s) and 100 mg/kg (11.9 ± 0.9 s). In the first phase of the formalin test, AtEO decreased paw licking time at doses of 25, 50, and 100 mg/kg, with inhibition of 22%, 38%, and 83%; in the second phase, the same doses, decreased licking time with inhibition of 24%, 34%, and 76%. AtEO did not present a significant change in the spontaneous locomotor activity of the animals. Doses of 6.25, 12.5, 25, 50, and 100 mg/kg significantly reduced ear edema induced by topical application of xylene with percentages of 40%, 39%, 54%, 45%, and 45%, respectively. So, AtEO demonstrated low acute oral toxicity and exhibited significant antinociceptive and anti-inflammatory actions, consistent with the use of A. triplinervis in traditional medicine.


Assuntos
Analgésicos , Anti-Inflamatórios , Óleos Voláteis , Animais , Óleos Voláteis/farmacologia , Óleos Voláteis/isolamento & purificação , Camundongos , Analgésicos/farmacologia , Analgésicos/isolamento & purificação , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/isolamento & purificação , Brasil , Masculino , Relação Dose-Resposta a Droga , Asteraceae/química , Dor/tratamento farmacológico , Dor/induzido quimicamente , Edema/tratamento farmacológico , Edema/induzido quimicamente , Folhas de Planta/química , Benzoquinonas/farmacologia , Feminino
6.
Chem Biodivers ; 20(3): e202200210, 2023 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-36732885

RESUMO

There is an ongoing interest to identify alternative pesticidal agents to avoid the chronic problems associated with synthetic pesticides. Essential oils have shown promise as botanical pest control agents. In the present study, the essential oils of four members of the Lamiaceae (Callicarpa candicans, C. erioclona, C. macrophylla, and Karomia fragrans; Vietnamese names: Nàng nàng, Tu châu lông mem, Tu châu lá to and Cà dien, respectively), obtained from wild populations in Vietnam, have been obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry. The essential oils were formulated into microemulsions and the essential oils and their microemulsions were screened for mosquito larvicidal activity against Aedes aegypti, Aedes albopictus, Culex quinquefasciatus, and for molluscicidal activity against Pomacea canaliculata. Atractylone and (E)-caryophyllene dominated the volatiles of C. candicans (CCEO) and C. erioclona (CEEO), while the major component in C. macrophylla (CMEO) and K. fragrans (KFEO) was (E)-caryophyllene. The essential oils and microemulsions of both C. candicans and C. erioclona exhibited excellent larvicidal activity against all three mosquito species (Ae. aegypti, Ae. albopictus, and Cx. quinquefasciatus) with LC50 values <10 µg/mL. Additionally, the larvicidal activity of the microemulsions were significantly improved compared with their free essential oils, especially for C. candicans and C. erioclona. All four essential oils and their microemulsions showed excellent molluscicidal activity with LC50 <10 µg/mL. In most cases, the essential oils and microemulsions showed greater pesticidal activity against target organisms than the non-target freshwater fish, Oreochromis niloticus. The in silico studies on physicochemical and ADMET properties of the major components in the studied essential oils were also investigated and most of the compounds possessed a favorable ADMET profile. Computational modeling studies of the studied compounds demonstrated a favorable binding interaction with the mosquito odorant-binding protein target and support atractylone, ß-selinene, and caryophyllene oxide as potential inhibitors. Based on the observed pesticidal activities of the essential oils and their microemulsions, the Callicarpa species and K. fragrans should be considered for potential cultivation and further exploration as botanical pesticidal agents.


Assuntos
Aedes , Callicarpa , Inseticidas , Lamiaceae , Óleos Voláteis , Praguicidas , Animais , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Praguicidas/farmacologia , Vietnã , Inseticidas/farmacologia , Inseticidas/química , Larva
7.
Chem Biodivers ; 20(10): e202301120, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37691004

RESUMO

This work aims to evaluate the chemical composition, in vitro antioxidant capacity, and in vivo antitumoral activity of S. guianensis essential oil against Ehrlich's ascitic carcinoma and the effects on oxidative stress. The animals (Mus musculus) received a daily dose of S. guianensis oil orally (100 mg/kg) for 9 days. The main constituents of essential oil were curzerenone (16.4±1.5 %), drimenol (13.7±0.2 %), and spathulenol (12.4±0.8 %). S. guianensis oil showed antioxidant activity, inhibiting 11.1 % of DPPH radicals (95.7 mgTE/g); and 15.5 % of the ß-carotene peroxidation. The group treated with S. guianensis showed a significant reduction in tumor cells (59.76±12.33) compared to the tumor group (96.88±19.15). Essential oil of S. guianensis decreased MDA levels and increased SOD levels in liver tissue. The essential oil of S. guianensis reduced oxidative stress, and showed antitumor and antioxidant activity, being characterized as a new chemical profile in the investigation of pathologies such as cancer.

8.
Chem Biodivers ; 20(11): e202300392, 2023 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-37715705

RESUMO

Mikania micrantha is utilized as a therapeutic for the treatment of various human ailments including insect bites, rashes and itches of skin, chicken pox, healing of sores and wounds, colds and fever, nausea, jaundice, rheumatism, and respiratory ailments. This study aimed at summarizing the traditional uses, phytochemical profile, and biological activities of M. micrantha based on obtainable information screened from different databases. An up-to-date search was performed on M. micrantha in PubMed, Science Direct, clinicaltrials.gov, and Google Scholar databases with specific keywords. No language restrictions were imposed. Published articles, theses, seminar/conference papers, abstracts, and books on ethnobotany, phytochemistry and pharmacological evidence were considered. Based on the inclusion criteria, this study includes 53 published records from the above-mentioned databases. The results suggest that fresh leaves and whole plant are frequently used in folk medicine. The plant contains more than 150 different phytochemicals under the following groups: essential oils, phenolics and flavonoids, terpenes, terpene lactones, glycosides, and sulfated flavonoids. It contains carbohydrates and micronutrients including vitamins and major and trace minerals. M. micrantha possesses antioxidant, anti-inflammatory, anti-microbial, anti-dermatophytic, anti-protozoal, anthelmintic, cytotoxic, anxiolytic, anti-diabetic, lipid-lowering and antidiabetic, spasmolytic, memory-enhancing, wound-healing, anti-aging, and thrombolytic activities. No clinical studies have been reported to date. M. micrantha might be one of the potential sources of phytotherapeutic compounds against diverse ailments in humans. Studies are required to confirm its safety profile in experimental animals prior to initiating clinical trials. Moreover, adequate investigation is also crucial to clarify exact mechanism of action for each biological effect.


Assuntos
Mikania , Plantas Medicinais , Animais , Humanos , Fitoterapia , Etnofarmacologia , Etnobotânica , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico , Flavonoides , Extratos Vegetais/química
9.
Int J Mol Sci ; 24(11)2023 May 25.
Artigo em Inglês | MEDLINE | ID: mdl-37298210

RESUMO

Depression is a mental disorder that affects more than 300 million people worldwide. The medications available for treatment take a long time to exhibit therapeutic results and present several side effects. Furthermore, there is a decrease in the quality of life of people suffering from this affliction. Essential oils are traditionally used to relieve the symptoms of depression due to the properties of the constituents of these oils to cross the blood-brain barrier acting on depression-related biological receptors associated with reduced toxicity and side effects. In addition, compared to traditional drugs, they have several administration forms. This review provides a comprehensive assessment of studies on plants whose essential oil has exhibit antidepressant activity in the past decade and the mechanism of action of the major components and models tested. An additional in silico study was conducted with the frequent compounds in the composition of these essential oils, providing a molecular approach to the mechanism of action that has been reported in the past decade. This review is valuable for the development of potential antidepressant medications in addition to providing a molecular approach to the antidepressant mechanism of action of the major volatile compounds that have been reported in the past decade.


Assuntos
Óleos Voláteis , Sesquiterpenos , Humanos , Óleos Voláteis/farmacologia , Óleos Voláteis/uso terapêutico , Óleos Voláteis/química , Simulação de Acoplamento Molecular , Qualidade de Vida , Antidepressivos/farmacologia , Antidepressivos/uso terapêutico , Antidepressivos/química , Monoterpenos/farmacologia
10.
Molecules ; 28(6)2023 Mar 08.
Artigo em Inglês | MEDLINE | ID: mdl-36985451

RESUMO

Conifers are of great economic value in terms of lumber production, important for construction and other uses such as pulp and paper. They are also important sources of essential oils. Conifer species have been vital to the ethnobotany and traditional herbal medicine of many different Native American groups. The objective of this work was to obtain and analyze the essential oils of several conifer species (Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata) growing in Idaho. The foliar essential oils were obtained by hydrodistillation and then analyzed by gas chromatographic methods, including GC-MS, GC-FID, and chiral GC-MS. The essential oils were obtained in varying yields from 0.66% up to 4.70%. The essential oil compositions were largely dominated by monoterpene hydrocarbons and oxygenated monoterpenoids. The chiral monoterpenoids were generally rich in the (-)-enantiomers for members of the Pinaceae, but the (+)-enantiomers predominated in the Cupressaceae. The essential oil compositions obtained in this work are qualitatively similar, but quantitatively different, to previously reported compositions and confirm and complement the previous reports. However, this is the first comprehensive analysis of the chiral terpenoid components in these conifer species. Additional research on essential oils of the Pinaceae and Cupressaceae is needed to describe the chemical profiles, chemical compositions, and enantiomeric distributions more reliably in the various species and infraspecific taxa of these two families.


Assuntos
Abies , Óleos Voláteis , Picea , Pinus , Pseudotsuga , Thuja , Humanos , Picea/química , Cycadopsida , Idaho , Monoterpenos
11.
Molecules ; 28(9)2023 May 02.
Artigo em Inglês | MEDLINE | ID: mdl-37175263

RESUMO

Grindelia squarrosa is an arid lands herb that has been used in Native American traditional medicine, is a potential source of pharmacologically active compounds, and has been explored as a source of biofuel. The purpose of this work was to examine the essential oil composition of G. squarrosa from southern Idaho. Gas chromatographic methods revealed the essential oil of G. squarrosa var. serrulata to be rich in monoterpenoids, α-pinene (21.9%), limonene (17.1%), terpinolene (10.6%), and borneol (6.5%). The essential oil composition of G. squarrosa from Idaho is similar to that previously reported from specimens collected from Montana and confirms the volatile phytochemistry of plants growing in North America. The major essential oil components were screened for antimicrobial activity against respiratory and dermal pathogens. (-)-ß-Pinene showed strong antibacterial activity against Streptococcus pneumoniae (MIC 39.1 µg/mL) and (-)-borneol showed strong activity against Staphylococcus aureus (MIC 78.1 µg/mL).


Assuntos
Grindelia , Óleos Voláteis , Antibacterianos/análise , Antibacterianos/química , Antibacterianos/farmacologia , Grindelia/química , Idaho , Testes de Sensibilidade Microbiana , Óleos Voláteis/análise , Óleos Voláteis/química , Óleos Voláteis/farmacologia , Monoterpenos/análise , Monoterpenos/química , Monoterpenos/farmacologia , Streptococcus pneumoniae/efeitos dos fármacos , Staphylococcus aureus/efeitos dos fármacos , Antifúngicos/análise , Antifúngicos/química , Antifúngicos/farmacologia
12.
Molecules ; 28(2)2023 Jan 05.
Artigo em Inglês | MEDLINE | ID: mdl-36677603

RESUMO

Cymbopogon species essential oil (EO) carries significant importance in pharmaceuticals, aromatherapy, food, etc. The chemical compositions of Cymbopogon spp. Viz. Cymbopogon winterianus (citronella) Cymbopogon citratus (lemongrass), and Cymbopogon martini (palmarosa) were analyzed by gas chromatography−mass spectrometry (GC-MS), enantiomeric distribution by chiral GC-MS, and antimicrobial activities of some selected pure major compound and root and leaves EOs of citronella. The EO of leaves of Cymbopogon spp. showed comparatively higher yield than roots or other parts. Contrary to citral (neral and geranial) being a predominant compound of Cymbopogon spp., α-elemol (53.1%), α-elemol (29.5%), geraniol (37.1%), and citral (90.4%) were detected as major compounds of the root, root hair with stalk, leaf, and root stalk with shoot of citronella EO, respectively. Palmarosa leaves' EO contains neral (36.1%) and geranial (53.1) as the major compounds. In the roots of palmarosa EO, the prime components were α-elemol (31.5%), geranial (25.0%), and neral (16.6%). Similarly, lemongrass leaves' EO contains geraniol (76.6%) and geranyl acetate (15.2%) as major compounds, while the root EO contains a higher amount of geraniol (87.9%) and lower amount of geranyl acetate (4.4%). This study reports for the first time chiral terpenoids from Cymbopogon spp. EOs. Chiral GC-MS gave specific enantiomeric distributions of nine, six, and five chiral terpenoids in the root, root stalk with a shoot, and leaves of citronella EOs, respectively. Likewise, four and three chiral terpenoids in the root and leaves of lemongrass oil followed by two chiral terpenoids in the leaves and root of palmarosa EOs each. Additionally, the root and leaves' EOs of citronella exhibit noticeable activity on bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes and fungus such as Candida albicans, Microsporum canis, and Trichophyton mentagrophytes. So, geranial-, neral-, geraniol-, and citronellal-rich EOs can be used as an alternative antimicrobial agent.


Assuntos
Anti-Infecciosos , Cymbopogon , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Cromatografia Gasosa-Espectrometria de Massas , Cymbopogon/química , Nepal , Anti-Infecciosos/farmacologia
13.
Molecules ; 28(5)2023 Mar 03.
Artigo em Inglês | MEDLINE | ID: mdl-36903605

RESUMO

Using essential oils to control vectors, intermediate hosts, and disease-causing microorganisms is a promising approach. The genus Croton in the family Euphorbiaceae is a large genus, with many species containing large amounts of essential oils, however, essential oil studies are limited in terms of the number of Croton species investigated. In this work, the aerial parts of C. hirtus growing wild in Vietnam were collected and analyzed by gas chromatography/mass spectrometry (GC/MS). A total of 141 compounds were identified in C. hirtus essential oil, in which sesquiterpenoids dominated, comprising 95.4%, including the main components ß-caryophyllene (32.8%), germacrene D (11.6%), ß-elemene (9.1%), α-humulene (8.5%), and caryophyllene oxide (5.0%). The essential oil of C. hirtus showed very strong biological activities against the larvae of four mosquito species with 24 h LC50 values in the range of 15.38-78.27 µg/mL, against Physella acuta adults with a 48 h LC50 value of 10.09 µg/mL, and against ATCC microorganisms with MIC values in the range of 8-16 µg/mL. In order to provide a comparison with previous works, a literature survey on the chemical composition, mosquito larvicidal, molluscicidal, antiparasitic, and antimicrobial activities of essential oils of Croton species was conducted. Seventy-two references (seventy articles and one book) out of a total of two hundred and forty-four references related to the chemical composition and bioactivity of essential oils of Croton species were used for this paper. The essential oils of some Croton species were characterized by their phenylpropanoid compounds. The experimental results of this research and the survey of the literature showed that Croton essential oils have the potential to be used to control mosquito-borne and mollusk-borne diseases, as well as microbial infections. Research on unstudied Croton species is needed to search for species with high essential oil contents and excellent biological activities.


Assuntos
Croton , Culicidae , Inseticidas , Óleos Voláteis , Animais , Óleos Voláteis/química , Croton/química , Vietnã , Mosquitos Vetores , Óleo de Cróton , Inseticidas/química
14.
Molecules ; 28(8)2023 Apr 11.
Artigo em Inglês | MEDLINE | ID: mdl-37110606

RESUMO

Hyptis crenata (Pohl) ex Benth is used in traditional medicine as an analgesic to treat general pain. Six Hyptis crenata samples (Hc-1 to Hc-6) were collected in Pará state, Brazil. The leaf essential oils were obtained by hydrodistillation, and GC-MS and GC-FID were used to analyze their chemical compositions. The antioxidant capacity was measured in vitro using DPPH and carotene/linoleic acid assays. Chemometrics analysis (PCA, HCA, and clustered heat map) were used to identify the sample relationships between those collected in this study and those from the literature (Hc-7 to Hc-16) samples. According to the main chemical constituents identified in the samples described in this work and the literature, the sixteen samples were classified into ten groups. Group I was characterized by 1,8-cineole (31.0%), α-pinene (13.6%), (E)-caryophyllene (7.8%), and ß-pinene (7.6%); and Group IV was characterized by 1,8-cineole (17.4-23.5%), α-pinene (15.7-23.5%), ß-pinene (10.5-13.4%), and limonene (8.5-9.7%). Both groups are described for the first time. The total antioxidant capacity was expressed in Trolox Equivalent Antioxidant Capacity values (TEAC): TEAC of Hc-5 (551.9 mg.TE/g) and Hc-6 (475.1 mg.TE/g). In the ß-carotene/linoleic acid assay, the highest inhibition was from Hc-2 (40.0%), Hc-6 (39.0%), and Hc-3 (29.4%).


Assuntos
Hyptis , Óleos Voláteis , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Antioxidantes/farmacologia , Antioxidantes/química , Hyptis/química , Eucaliptol , Brasil , Quimiometria , Ácido Linoleico
15.
Molecules ; 28(8)2023 Apr 14.
Artigo em Inglês | MEDLINE | ID: mdl-37110711

RESUMO

Pouteria macrophylla (cutite) fruits are rich in phenolic acids, resulting in antioxidant and skin depigmenting activity. The aim of this study, then, is to evaluate the cutite extract stability under three variations of light, time, and temperature using a Box-Behnken experimental design to analyze through the surface response the variations of the total phenolic content (TPC), antioxidant activity (AA), and gallic acid content (GA). A colorimetric assay was also performed, and a decrease in the darkening index was noticed due to the high phenolic coloration in the presence of light, indicating less degradation to extract stability. The experimental planning showed variations in all responses, and second-order polynomial models were calculated and considered predictable, as well as the effects were significant. The TPC exhibited a variation in less concentrated samples (0.5% p/v) at higher temperatures (90 °C). In contrast, the temperature was the only influential variable for AA, where only higher temperatures (60-90 °C) were able to destabilize the fruit extract. Differently, GA showed only the concentration as the influential variable, exhibiting that neither temperature nor time of exposure could affect the gallic acid content stability of P. macrophylla extract. For this, P. macrophylla extract was shown to be highly stable, providing a great perspective on cosmetic application.


Assuntos
Antioxidantes , Pouteria , Antioxidantes/farmacologia , Ácido Gálico/análise , Frutas/química , Extratos Vegetais/farmacologia , Fenóis/análise
16.
Molecules ; 28(22)2023 Nov 09.
Artigo em Inglês | MEDLINE | ID: mdl-38005226

RESUMO

The essential oils of five Vietnamese Syzygium species (Syzygium levinei, S. acuminatissimum, S. vestitum, S. cumini, and S. buxifolium) were first hydro-distilled and analyzed using GC-FID/MS (gas chromatography-flame ionization detection/mass spectrometry). Monoterpene hydrocarbons, sesquiterpene hydrocarbons, and oxygenated sesquiterpenoids were the main chemical classes in these oils. All these essential oils showed good-excellent antimicrobial activities against Gram-positive bacteria Enterococcus faecalis, Staphylococcus aureus, and Bacillus cereus, and the yeast Candida albicans. S. levinei leaf essential oil, rich in bicyclogermacrene (25.3%), (E)-ß-elemene (12.2%), (E)-caryophyllene (8.2%), and ß-selinene (7.4%), as well as S. acuminatissimum fruit essential oil containing (E)-caryophyllene (14.2%), α-pinene (12.1%), caryophyllene oxide (10.9%), ß-selinene (10.8%), α-selinene (8.0%), and α-humulene (5.7%), established the same MIC value of 8 µg/mL against E. faecalis and B. cereus, which were much better than the positive control streptomycin (MIC 128-256 µg/mL). The studied essential oils showed the potential to defend against mosquitoes since they caused the 24 and 48 h LC50 values of less than 50 µg/mL against the growth of Culex quinquefasciatus and Aedes aegypti larvae. Especially, S. buxifolium leaf essential oil strongly inhibited Ae. aegypti larvae with 24 and 48 h LC50 values of 6.73 and 6.73 µg/mL, respectively, and 24 and 48 h LC90 values of 13.37 and 10.83 µg/mL, respectively. These findings imply that Vietnamese Syzygium essential oils might have potential for use as supplemental antibacterial agents or as "green" alternatives for the control of mosquitoes.


Assuntos
Aedes , Anti-Infecciosos , Inseticidas , Óleos Voláteis , Syzygium , Animais , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Syzygium/química , Vietnã , Cromatografia Gasosa-Espectrometria de Massas , Anti-Infecciosos/farmacologia , Inseticidas/química , Larva
17.
Molecules ; 28(22)2023 Nov 14.
Artigo em Inglês | MEDLINE | ID: mdl-38005295

RESUMO

Aniba canelilla (Kunth) Mez essential oil has many biological activities due to its main compound 1-nitro-2-phenylethane (1N2F), followed by methyleugenol, a carcinogenic agent. This study analyzed the influence of seasonality on yields, antioxidant capacity, and 1N2F content of A. canelilla leaf and twig essential oils. Essential oils (EOs) were extracted with hydrodistillation and analyzed with gas chromatography coupled to mass spectrometry and a flame ionization detector. Antioxidant capacity was measured using the free radical scavenging method (DPPH). Chemometric analyses were carried out to verify the influence of climatic factors on the production and composition of EOs. 1-Nitro-2-phenylethane was the major constituent in A. canelilla EOs throughout the seasonal period (68.0-89.9%); methyleugenol was not detected. Essential oil yields and the 1N2F average did not show a statistically significant difference between the dry and rainy seasons in leaves and twigs. Moderate and significant correlations between major compounds and climate factor were observed. The twig oils (36.0 ± 5.9%) a showed greater antioxidant capacity than the leaf oils (20.4 ± 5.0%). The PCA and HCA analyses showed no statistical differences between the oil samples from the dry and rainy seasons. The absence of methyleugenolin in all months of study, described for the first time, makes this specimen a reliable source of 1N2F.


Assuntos
Lauraceae , Óleos Voláteis , Óleos Voláteis/química , Lauraceae/química , Estações do Ano , Antioxidantes/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Folhas de Planta
18.
Planta Med ; 88(14): 1341-1347, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-35468649

RESUMO

Cryptococcus neoformans is an opportunistic fungal pathogen that has limited treatment options. Natural product plant extracts offer a cost-effective option for the discovery of new anticryptococcal lead compounds. The acetone bark extract of Verbesina turbacensis was found to potently inhibit C. neoformans and was subjected to bioautography. Two compounds that inhibited the growth of C. neoformans were isolated and displayed minimum inhibitory concentration values of 10 and 310 µg/mL. The compounds were identified as the bornyl hydroxycinnamic esters bornyl caffeate and bornyl ferulate, respectively. To better understand initial structure-activity relationships, anticryptococcal activity was characterized for similar compounds. All compounds were further evaluated for mammalian cell toxicity using the MTT assay with MCF-7 and HEK-293 cell lines. Overall, bornyl caffeate demonstrated promising anticryptococcal potential given its potent inhibition of C. neoformans and low mammalian cell toxicity.


Assuntos
Cryptococcus neoformans , Verbesina , Animais , Humanos , Células HEK293 , Relação Estrutura-Atividade , Antifúngicos/farmacologia , Mamíferos
19.
Chem Biodivers ; 19(10): e202200337, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-36068087

RESUMO

The Ocotea complex accommodates most of the taxonomic diversity of Neotropical Lauraceae with economic importance and biological potential attributed to their essential oils (EOs) and extracts. However, the botanical taxonomy has had limitations due to the difficulty of identifying and delimiting species and genera. The chemical and molecular markers of Ocotea complex species in Pará state, Brazil, were assessed according to their EO compositions and DNA sequences of matK, trnL-trnF, and ITS regions. The multivariate analysis of EOs constituents has classified them into two main clusters characterized by oils rich in (I) terpenoids and phenylpropanoids and (II) sesquiterpenes. We conducted a phylogenetic analysis of species based on DNA barcode sequences on the Bayesian Inference (PP: 0.70-1,0) and Maximum Likelihood (BS: 72-100 %). The comparison between the volatile profiles and phylogenetic data indicates two main groups for these species collected from the Ocotea complex.


Assuntos
Lauraceae , Ocotea , Óleos Voláteis , Sesquiterpenos , Ocotea/química , Lauraceae/genética , Lauraceae/química , Brasil , Código de Barras de DNA Taxonômico , Filogenia , Teorema de Bayes , Óleos Voláteis/química , Terpenos , Extratos Vegetais
20.
Molecules ; 27(19)2022 Sep 23.
Artigo em Inglês | MEDLINE | ID: mdl-36234812

RESUMO

Citrus essential oils are routinely adulterated because of the lack of regulations or reliable authentication methods. Unfortunately, the relatively simple chemical makeup and the tremendous price variations among Citrus varieties encouraged the interspecies adulteration of citrus oils. In this study, a sensitive UPLC-MS/MS method for the quantitation of 14 coumarins and furanocoumarins is developed and validated. This method was applied to screen the essential oils of 12 different Citrus species. This study, to our knowledge, represents the most comprehensive investigation of coumarin and furanocoumarin profiles across commercial-scale Citrus oils to date. Results show that the lowest amount was detected in calamansi oil. Expressed oil of Italian bergamot showed the highest furanocoumarin content and the highest level of any individual furanocoumarin (bergamottin). Notable differences were observed in the coumarin and furanocoumarin levels among oils of different crop varieties and origins within the same species. Potential correlations were observed between bergapten and xanthotoxin which matches with known biosynthetic pathways. We found patterns in furanocoumarin profiles that line up with known variations among the Citrus ancestral taxa. However, contrary to the literature, we also detected xanthotoxin in sweet orange and members of the mandarin taxon. Using multivariate analysis, we were able to divide the Citrus oils into 5 main groups and correlate them to the coumarin compositions.


Assuntos
Citrus , Furocumarinas , Óleos Voláteis , 5-Metoxipsoraleno , Cromatografia Líquida , Citrus/química , Cumarínicos/química , Furocumarinas/química , Metoxaleno , Óleos Voláteis/química , Óleos de Plantas , Espectrometria de Massas em Tandem
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