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1.
Oxid Med Cell Longev ; 2022: 9354555, 2022.
Article in English | MEDLINE | ID: mdl-36246399

ABSTRACT

C. camphora is a renowned traditional Unani medicinal herb and belongs to the family Lauraceae. It has therapeutic applications in various ailments and prophylactic properties to prevent flu-like epidemic symptoms and COVID-19. This comprehensive appraisal is to familiarize the reader with the traditional, broad applications of camphor both in Unani and modern medicine and its effects on bioactive molecules. Electronic databases such as Web of Science, PubMed, Google Scholar, Scopus, and Research Gate were searched for bioactive molecules, and preclinical/clinical research and including 59 research and review papers up to 2022 were retrieved. Additionally, 21 classical Unani and English herbal pharmacopeia books with ethnomedicinal properties and therapeutic applications were explored. Oxidative stress significantly impacts aging, obesity, diabetes mellitus, depression, and neurodegenerative diseases. The polyphenolic bioactive compounds such as linalool, borneol, and nerolidol of C. camphora have antioxidant activity and have the potential to remove free radicals. Its other major bioactive molecules are camphor, cineole, limelol, safrole, limonene, alpha-pinene, and cineole with anti-inflammatory, antibacterial, anxiolytic, analgesic, immunomodulatory, antihyperlipidemic, and many other pharmacological properties have been established in vitro or in vivo preclinical research. Natural bioactive molecules and their mechanisms of action and applications in diseases have been highlighted, with future prospects, gaps, and priorities that need to be addressed.


Subject(s)
Anti-Anxiety Agents , COVID-19 Drug Treatment , Cinnamomum camphora , Analgesics , Anti-Bacterial Agents , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/therapeutic use , Antioxidants/pharmacology , Camphor , Ethnopharmacology , Eucalyptol , Hypolipidemic Agents , Limonene , Phytochemicals , Phytotherapy , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Safrole
2.
Chemistry ; 28(61): e202201997, 2022 Nov 02.
Article in English | MEDLINE | ID: mdl-35938698

ABSTRACT

Chiral sulfoxides are versatile synthons and have gained a particular interest in asymmetric synthesis of active pharmaceutical and agrochemical ingredients. Herein, a linear oxidation-reduction bienzymatic cascade to synthesize chiral sulfoxides is reported. The extraordinarily stable and active vanadium-dependent chloroperoxidase from Curvularia inaequalis (CiVCPO) was used to oxidize sulfides into racemic sulfoxides, which were then converted to chiral sulfoxides by highly enantioselective methionine sulfoxide reductase A (MsrA) and B (MsrB) by kinetic resolution, respectively. The combinatorial cascade gave a broad range of structurally diverse sulfoxides with excellent optical purity (>99 %  ee) with complementary chirality. The enzymatic cascade requires no NAD(P)H recycling, representing a facile method for chiral sulfoxide synthesis. Particularly, the envisioned enzymatic cascade not only allows CiVCPO to gain relevance in chiral sulfoxide synthesis, but also provides a powerful approach for (S)-sulfoxide synthesis; the latter case is significantly unexplored for heme-dependent peroxidases and peroxygenases.


Subject(s)
Methionine Sulfoxide Reductases , Sulfoxides , Oxidation-Reduction , Safrole
3.
Org Lett ; 24(11): 2214-2219, 2022 03 25.
Article in English | MEDLINE | ID: mdl-35285237

ABSTRACT

The combined use of BnS(O)CF3/BnSe(O)CF3 with Tf2O as SCF3/SeCF3 reagents was implemented to realize an efficient synthesis of biologically interesting 4-(trifluoromethylthio/trifluoromethylseleno)isocoumarins from 2-alkynylbenzoates. The mechanistic pathway was postulated to involve formation of the electrophilic SCF3/SeCF3 species via interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.


Subject(s)
Selenium , Sulfoxides , Indicators and Reagents , Molecular Structure , Safrole/analogs & derivatives
4.
Biomed Res Int ; 2021: 6699033, 2021.
Article in English | MEDLINE | ID: mdl-33829063

ABSTRACT

Asarum is a traditional medicine and has been widely used as remedies for inflammatory diseases, toothache, headache, local anesthesia, and aphthous stomatitis in China, Japan, and Korea. Our previous research found that safrole and methyl eugenol were vital compounds that contribute to distinguish the different species and raw Asarum and its processed products apart. The pharmacokinetics of safrole and methyl eugenol after oral administration of Asarum extract has not been reported yet. In this study, a rapid and simple gas chromatography-mass spectroscopy (GC-MS) method that has a complete run time of only 4.5 min was developed and validated for the simultaneous determination and pharmacokinetic study of safrole and methyl eugenol in rat plasma after administration of Asarum extracts. The chromatographic separation was realized on a DB-17 column (30 m × 0.25 mm × 0.25 µm). And detection was carried out under selected ion monitoring (SIM) mode. Plasma samples were pretreated by n-hexane. The pharmacokinetic parameters provided by this study will be beneficial for further developments and clinical applications of Asarum.


Subject(s)
Asarum/chemistry , Eugenol/analogs & derivatives , Gas Chromatography-Mass Spectrometry , Oils, Volatile/administration & dosage , Plant Extracts/administration & dosage , Safrole/administration & dosage , Safrole/pharmacokinetics , Administration, Oral , Animals , Calibration , Eugenol/administration & dosage , Eugenol/blood , Eugenol/chemistry , Eugenol/pharmacokinetics , Limit of Detection , Male , Rats, Sprague-Dawley , Reference Standards , Reproducibility of Results , Safrole/blood , Safrole/chemistry
5.
PLoS One ; 16(1): e0244159, 2021.
Article in English | MEDLINE | ID: mdl-33400695

ABSTRACT

The application of reclaimed asphalt pavement has been widely encouraged due to its significant economic and environmental benefits. However, it is necessary to add rejuvenators to ensure its performance. Currently, bio-oil-based regenerants have attracted attention owing to their advantages of renewability and cost savings. The purpose of this paper is to study the use of recycled vegetable oil waste (R-oil) and recycled polyethylene particles for the regeneration and modification of aged asphalt. Physical, rheological, and chemical tests were used to figure out their influence on the pavement performance of aged asphalt. According to the physical test indices (penetration, softening point, and ductility), the performance of the rejuvenated asphalt was better than that of virgin asphalt. The workability and low-temperature performance of the rejuvenated asphalt were basically the same as those of virgin asphalt, and its fatigue and high-temperature performance were better. Infrared spectroscopy showed that R-oil diluted the high-polarity sulfoxide base of aged asphalt. Gel permeation chromatography showed that its molecular weight dispersion was better than that of aged asphalt. Therefore, R-oil and polyethylene can improve the pavement performance and chemical properties of aged asphalt.


Subject(s)
Construction Materials/analysis , Hydrocarbons/chemistry , Plant Oils/chemistry , Polyethylene/chemistry , Chromatography, Gel , Cold Temperature , Feasibility Studies , Molecular Weight , Recycling , Safrole/analogs & derivatives , Safrole/analysis , Time Factors
6.
Molecules ; 25(19)2020 Oct 06.
Article in English | MEDLINE | ID: mdl-33036279

ABSTRACT

Acne is a common skin condition observed in adolescents. Nutmeg (Myristica fragrans Houtt) (MF) is a well-known traditional Chinese medicine; its major toxic components, safrole and myristicin, are rich in essential oils. Essential oils of MF (MFO) were extracted by hydrodistillation; the residue was extracted using 50% methanol (MFE-M). The minimum inhibitory concentration (MIC) of MFE-M against Cutibacterium acnes and Staphylococcus aureus was 0.64 mg. Four compounds were obtained from MFE-M: myristicin (1), (+)-erythro-Δ8'-7S,8R- dihydroxy-3,3,5'-trimethoxy-8-O-4'-neolignan (2), (+)-erythro-Δ8'-7-hydroxy-3,4,3',5'-tetramethoxy 8-O-4-neolignan (3), and erythro-Δ8'-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (4). Compound 2 exerted the strongest antimicrobial activity, with MICs of 6.25 and 3.12 µg/mL against C. acnes and S. aureus, respectively. Moreover, 2 inhibited NO, PGE2, iNOS, and COX-2 levels in RAW 264.7 cells induced by LPS or heat-killed C. acnes; NO production at 50% inhibitory concentrations (IC50) was 11.07 and 11.53 µg/mL, respectively. Myristicin and safrole content was higher in MFO than in MFE-M. MFO and MFE-M caused no skin irritation after a single topical application in Wistar rats. MFE-M, with low safrole and myristicin content, did not cause skin irritation and exhibited an anti-acne effect; moreover, 2 was identified as the active substance. Therefore, MFE-M could be employed to develop anti-acne compounds for use in cosmetics.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Lignans/chemistry , Myristica/chemistry , Allylbenzene Derivatives/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Dioxolanes/pharmacology , Female , Propionibacteriaceae/drug effects , Rats , Rats, Wistar , Safrole/pharmacology , Skin/drug effects , Staphylococcus aureus/drug effects
7.
Food Chem Toxicol ; 145: 111585, 2020 Nov.
Article in English | MEDLINE | ID: mdl-32702506

ABSTRACT

In 2015, the Expert Panel of the Flavor and Extract Manufacturers Association initiated the safety re-evaluation of over 250 natural flavor complexes (NFCs) used as flavor ingredients. This publication, 4th in a series focusing on the safety evaluation of NFCs, presents an evaluation of NFCs rich in hydroxyallylbenzene and hydroxypropenylbenzene constituents using a procedure initially published in 2005 and updated in 2018 that evaluates the safety of naturally occurring mixtures for their intended use as flavoring ingredients. The procedure requires the characterization of the chemical composition for each NFC and subsequent organization of the constituents into defined congeneric groups. The safety of each NFC is evaluated using the conservative threshold of toxicological concern (TTC) approach together with studies on absorption, metabolism and toxicology of the NFC and its constituent congeneric groups. By the application of this procedure, seven NFCs, derived from clove, cinnamon leaf and West Indian bay leaf were affirmed as "generally recognized as safe (GRAS)" under their conditions of intended use as flavor ingredients. An eighth NFC, an oleoresin of West Indian bay leaf, was affirmed based on its estimated intake, which is below the TTC of 0.15 µg/person per day for compounds with structural alerts for genotoxicity.


Subject(s)
Cinnamomum zeylanicum/chemistry , Flavoring Agents/toxicity , Laurus/chemistry , Syzygium/chemistry , Allylbenzene Derivatives , Animals , Anisoles/chemistry , Anisoles/toxicity , Consumer Product Safety , Escherichia coli/drug effects , Eugenol/chemistry , Eugenol/toxicity , Female , Flavoring Agents/chemistry , Humans , Male , Mice , Mutagenicity Tests , No-Observed-Adverse-Effect Level , Plant Oils/chemistry , Plant Oils/toxicity , Rats , Safrole/chemistry , Safrole/toxicity , Salmonella typhimurium/drug effects
8.
Regul Toxicol Pharmacol ; 105: 36-41, 2019 Jul.
Article in English | MEDLINE | ID: mdl-30935955

ABSTRACT

Food-borne alkenylbenzenes are potential risks for human health because they are known to induce liver tumors in rodent bioassays at high dose levels. This carcinogenicity is ascribed to the conversion of their 1'-hydroxymetabolites to the ultimate DNA reactive and carcinogenic 1'-sulfoxymetabolites. The aim of this study was to investigate the in vitro genotoxicity of some botanical extracts used as Plant Food Supplements (PFS) and to compare it with the individual substances, estragole, safrole and their 1'-hydroxy-derivative activity. The genotoxicity of the PFSs was evaluated in HepG2 cell line by comet and micronucleus assays. Unlike the 1'-hydroxy derivatives, PFS extracts and parent alkenylbenzenes did not show genotoxicity at any of the tested concentrations. The sulfotransferase inhibitor pentachlorophenol (PCP) reduced the 1'-hydroxy compound-induced response in the comet and micronucleus assays, thus confirming that the formation of sulfoxy-metabolites is essential for inducing genotoxic effects. When the cells were treated with hydroxylated alkenylbenzenes in the presence of PFSs, a reduction in genotoxic activity of synthetic compounds was observed.


Subject(s)
Anisoles/toxicity , Benzene Derivatives/toxicity , Plant Extracts/toxicity , Safrole/toxicity , Allylbenzene Derivatives , Benzene Derivatives/chemistry , Comet Assay , Hep G2 Cells , Humans , Micronucleus Tests , Mutagens/toxicity , Plant Extracts/chemistry
9.
Rev. biol. trop ; Rev. biol. trop;66(2): 826-835, abr.-jun. 2018. tab, graf
Article in Spanish | LILACS, SaludCR | ID: biblio-977348

ABSTRACT

Resumen La leishmaniasis es una enfermedad con una alta incidencia en el ser humano, que puede ser controlada, pero como los tratamientos tienen efectos secundarios importantes se han realizado estudios de diversas plantas con el fin de encontrar compuestos con actividad antileishmaniásica que presenten pocos efectos nocivos para el ser humano. El presente estudio consistió en realizar un tamizaje fitoquímico de la planta, para identificar la presencia de cumarinas, terpenos, triterpenos y azúcares reductores. El objetivo fue encontrar componentes químicos puros con actividad contra el parásito Leishmania sp. Por tal razón se purificaron los compuestos: trans-Z-alfabisaboleno y el Safrol, a los que se les realizaron pruebas del efecto anti parasitario que presentaron un CI50 de 50.0 µg/mL y 0.0 µg/mL, respectivamente. Además, se discute la importancia de estos nuevos hallazgos. El compuesto mayoritario presente en los aceites esenciales (Safrol) no es el componente que presentó la actividad. Es importante realizar estudios sobre su proyección en el tratamiento de la leishmaniasis.


Abstract The leishmaniosis disease incidence is high in tropical regions, and its current treatment has shown severe secondary effects. Considering this problem, many studies have focused on plants, looking for chemical components that have anti-leishmanial activity, and are free of adverse effects for human beings. The purpose of this work was to find a chemical component with this kind of activity in Piper auritum. In a phytochemical screening of this plant, we found some cumarins, terpens, triterpens and reducing sugars; and later, we identified the components trans-Z-α-bisabolene epoxide and Safrol. The first component presented a CI50 of 50.0 µg/mL of anti-Leishmania activity. The Safrol, which is the major component of the essential oils of this plant, did not show antiparasitic activity. These results are discussed considering treatment of leishmaniasis. Rev. Biol. Trop. 66(2): 826-835. Epub 2018 June 01.


Subject(s)
Safrole/therapeutic use , Leishmaniasis , Trypanosomatina , Piperaceae/parasitology , Epoxy Compounds , Phytochemicals/administration & dosage , Monocyclic Sesquiterpenes/therapeutic use , Leishmania
10.
J Econ Entomol ; 108(3): 1208-14, 2015 Jun.
Article in English | MEDLINE | ID: mdl-26470247

ABSTRACT

Lycoriella ingenua (Dufour) (Diptera: Sciaridae) and Coboldia fuscipes (Meigen) (Diptera: Scatopsidae) are two of the most economically important insect pests of cultivated mushrooms. The toxicities to the fly larvae of the three phenylpropanoids (methyleugenol, myristicin, and safrole) from aerial parts of Asarum sieboldii Miquel (Aristolochiaceae) were compared with those of the currently available carbamate insecticide benfuracarb. In a contact+fumigant mortality bioassay with L. ingenua and C. fuscipes larvae, methyleugenol (1.46 and 2.33 µg/cm2) was the most toxic compound, followed by safrole (2.03 and 2.59 µg/cm2) and myristicin (3.59 and 4.96 µg/cm2), based on 24-h LC50 values. The phenylpropanoids were less toxic than benfuracarb (LC50, 0.75 and 0.55 µg/cm2). In vapor-phase mortality tests with the larvae, the phenylpropanoids were consistently more toxic in closed versus open containers, indicating that the effect of the compounds was largely a result of vapor action. Global efforts to reduce the level of highly toxic synthetic insecticides in the agricultural environment justify further studies on A. sieboldii plant-derived products as potential fumigants for the control of mushroom fly populations in mushroom houses and mushroom compost.


Subject(s)
Asarum/chemistry , Benzyl Compounds , Dioxolanes , Diptera , Eugenol/analogs & derivatives , Insect Control , Insecticides , Pyrogallol/analogs & derivatives , Safrole , Allylbenzene Derivatives , Animals , Benzofurans , Diptera/genetics , Diptera/growth & development , Fumigation , Larva , Plant Extracts/chemistry , Species Specificity , beta-Alanine/analogs & derivatives
11.
J Food Prot ; 78(4): 772-7, 2015 Apr.
Article in English | MEDLINE | ID: mdl-25836404

ABSTRACT

Water-distilled essential oil from Illicium henryi (Illiciaceae) root bark was analyzed by gas chromatography-mass spectrometry. Thirty-four compounds, accounting for 97.86% of the total oil, were identified. The main components of the essential oil of I. henryi root bark were safrole (46.12%), myristicin (20.39%), and 1,8-cineole (6.17%), followed by α-cadinol (3.784%) and linalool (3.22%). The essential oil had higher levels of phenylpropanoids (66.89%) than of monoterpenoids (14.83%) and sesquiternoids (16.14%). Three constituents were isolated from the oil based on bioactivity fractionation. The essential oil possessed fumigant toxicity against booklice (Liposcelis bostrychophila), with a 50% lethal concentration (LC50) of 380.39 µg/liter of air, while the two isolated constituents myristicin and safrole had LC50s of 121.95 and 322.54 µg/liter, respectively. Another constituent, 1,8-cineole, showed weaker toxicity, with an LC50 of 1,120.43 µg/liter. The essential oil also exhibited contact toxicity against L. bostrychophila, with an LC50 of 96.83 µg/cm(2). Myristicin (LC50, 18.74 µg/cm(2)) and safrole (LC50, 69.28 µg/cm(2)) exhibited stronger acute toxicity than 1,8-cineole (LC50, 1,049.41 µg/cm(2)) against the booklice. The results indicated that the essential oil and its constituent compounds have potential for development into natural insecticides for control of psocids in stored grains.


Subject(s)
Illicium/chemistry , Insecta , Insecticides/chemistry , Oils, Volatile/chemistry , Plant Oils/chemistry , Plant Roots/chemistry , Acyclic Monoterpenes , Allylbenzene Derivatives , Animals , Benzyl Compounds/chemistry , Cyclohexanols/chemistry , Dioxolanes/chemistry , Eucalyptol , Gas Chromatography-Mass Spectrometry , Lethal Dose 50 , Monoterpenes/chemistry , Pyrogallol/analogs & derivatives , Pyrogallol/chemistry , Safrole/chemistry , Terpenes/chemistry
12.
Cancer Prev Res (Phila) ; 8(1): 1-8, 2015 Jan.
Article in English | MEDLINE | ID: mdl-25348854

ABSTRACT

Consuming plants for their presumed health benefits has occurred since early civilizations. Phytochemicals are found in various plants that are frequently included in the human diet and are generally thought to be safe for consumption because they are produced naturally. However, this is not always the case and in fact many natural compounds found in several commonly consumed plants are potential carcinogens or tumor promoters and should be avoided.


Subject(s)
Neoplasms/drug therapy , Phytochemicals/toxicity , Phytotherapy , Plant Extracts/chemistry , Plants/chemistry , Amygdalin/therapeutic use , Aristolochic Acids/therapeutic use , Capsaicin/therapeutic use , Cell Line, Tumor , Cycasin/therapeutic use , Diet , Drug Screening Assays, Antitumor , Humans , Indans/therapeutic use , Phorbol Esters/therapeutic use , Phytoestrogens/therapeutic use , Pyrrolizidine Alkaloids/therapeutic use , Safrole/therapeutic use , Sesquiterpenes/therapeutic use
13.
J Biomol Tech ; 25(3): 67-76, 2014 Sep.
Article in English | MEDLINE | ID: mdl-25187757

ABSTRACT

Naturally occurring (+)-trans-isoalliin, (R(C)R(S))-(+)-trans-S-1-propenyl-L-cysteine sulfoxide, is a major cysteine sulfoxide in onion. The importance of producing it synthetically to support further research is very well recognized. The (+)-trans-isoalliin is prepared by chemical synthesis and reversed-phase (RP)-HPLC. First, S-2-propenyl-L-cysteine (deoxyalliin) is formed from L-cysteine and allyl bromide, which is then isomerized to S-1-propenyl-L-cysteine (deoxyisoalliin) by a base-catalyzed reaction. A mixture of cis and trans forms of deoxyisoalliin is formed and separated by RP-HPLC. Oxidation of the trans form of deoxyisoalliin by H2O2 produces a mixture of (-)- and (+)-trans-isoalliin. Finally, RP-HPLC is used successfully in separating (-)- and (+)-trans-isoalliin, and hence, (+)-trans-isoalliin is synthesized for the first time in this study. In addition, the (±) diastereomers of cis-isoalliin are also separated and purified by RP-HPLC.


Subject(s)
Cysteine/analogs & derivatives , Onions/chemistry , Allyl Compounds/chemistry , Catalysis , Chromatography, High Pressure Liquid , Cysteine/chemical synthesis , Cysteine/chemistry , Hydrogen Peroxide/chemistry , Isomerism , Safrole/analogs & derivatives , Safrole/chemistry
14.
Int J Clin Exp Pathol ; 7(5): 2265-72, 2014.
Article in English | MEDLINE | ID: mdl-24966935

ABSTRACT

The aim of this study was to study the anti-hepatoma effect of safrole and elucidate its molecular mechanism, the human hepatoma BEL-7402 cells were incubated with various concentrations (40, 80, 160, 320 and 640 µg/ml) of safrole and the cell proliferation and apoptosis were evaluated. The results showed that both the cell proliferation determined by 3-(4,5-dimethyl-thiazolyl-2)-2,5-diphenyl tetrazolium brominde (MTT) assay and cell colony determined by soft agar assay were significantly suppressed by safrole in a dose-time-dependent manner. Characteristic morphological and biochemical changes associated with apoptosis, including cells shrinkage, deformation and vacuolization of mitochondria, nuclear chromatin condensation and fragmentation, formation of apoptotic bodies were observed when treated with safrole for 24 h and 48 h. Cell cycle changes evaluated by flow cytometry analysis showed that the safrole could induce accumulation of cells arrested at G1 and S phases of the cell cycle. These results demonstrated that safrole is potent anti-hepatoma agent and the underlying mechanism may be attributed to suppress tumor cell growth by inducing cell apoptosis.


Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Carcinoma, Hepatocellular/pathology , Cinnamomum/chemistry , Liver Neoplasms/pathology , Oils, Volatile/chemistry , Plant Oils/chemistry , Safrole/pharmacology , Antineoplastic Agents, Phytogenic/isolation & purification , Apoptosis/drug effects , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , G1 Phase Cell Cycle Checkpoints/drug effects , Humans , Mitochondria/drug effects , Mitochondria/pathology , Phytotherapy , Plant Leaves , Plants, Medicinal , S Phase Cell Cycle Checkpoints/drug effects , Safrole/isolation & purification , Time Factors
15.
Bol. latinoam. Caribe plantas med. aromát ; 13(1): 10-19, ene. 2014. ilus, tab
Article in English | LILACS | ID: lil-726599

ABSTRACT

Stored grain insects have shown resistance to synthetic insecticides, fact that has promoted the use of vegetable species for integrated pest management. Piper auritum and P. multiplinervium are two plants from the Piperaceae family present in the department of Chocó, Colombia, one of the most important hot spots of biodiversity in the world. This study was conducted to determine the repellent activity and toxicity of essential oils (EOs) isolated from these plants against Tribolium castaneum, using the area preference and contact toxicity methods, respectively. P. auritum EO presented greater repellency than P. multiplinervium, the first showed 100 percent lethality at minimum tested exposure period (24 h) whereas the second reached 16 percent at 72 h. EOs were analyzed by gas chromatography-mass spectrometry. P. auritum major components were safrole (93.2 percent) and miristicine (4.3 percent), whereas for P. multiplinervium were beta-elemene (9.0 percent), trans-beta-caryophyllene (5.3 percent) and caryophyllene oxide (4.1 percent). It is speculated that the repellent effect of P. auritum may be related to its safrole content, a known repellent. These results evidenced Piper species could be used for development of repellents against T. castaneum.


Los insectos de los granos almacenados han mostrado resistencia a los insecticidas sintéticos, hecho que ha promovido el uso de especies vegetales para el manejo integrado de plagas. Piper auritum y P. multiplinervium son dos plantas de la familia Piperaceae presentes en el departamento del Chocó, Colombia, uno de los puntos de biodiversidad más importantes del mundo. En este estudio fue determinada la actividad repelente y toxicidad de los aceites esenciales (AE) aislados de estas plantas contra Tribolium castaneum, utilizando el método de área de preferencia y toxicidad por contacto, respectivamente. El AE de P. auritum presentó mayor repelencia que el de P. multiplinervium, el primero mostró 100 percent de letalidad al menor tiempo de exposición (24 h), mientras que el segundo alcanzó el 16 percent a las 72 h. Los AEs fueron analizados por cromatografía de gases-espectrometría de masas. Los componentes principales de P. auritum fueron safrol (93.2 percent) y miristicina (4.3 percent), mientras que para P. multiplinervium fueron beta-elemene (9.0 percent), trans-beta-cariofileno (5.3 percent) y óxido de cariofileno (4.1 percent). Se cree que el efecto repelente de P. auritum puede estar relacionado con su contenido de safrol, un repelente conocido. Estos resultados evidencian que las especies de Piper podrían ser utilizadas para el desarrollo de repelentes contra T. castaneum.


Subject(s)
Oils, Volatile/pharmacology , Plant Extracts/pharmacology , Insecticides/pharmacology , Piper/chemistry , Tribolium , Oils, Volatile/chemistry , Gas Chromatography-Mass Spectrometry , Safrole/analysis , Sesquiterpenes/analysis , Toxicity Tests
16.
Nat Prod Res ; 28(5): 294-300, 2014.
Article in English | MEDLINE | ID: mdl-24274027

ABSTRACT

Ocotea puchury-major Mart. is a tree native to the Brazilian rain forest, where it is popularly known as puxurì. In local folk medicine the leaves are used for their sedative, gastroenteric and antireumatic properties. The morphoanatomical study determined those features useful in distinguishing this species from other closely related taxa. Chemical analysis was focused on the study of the volatile oil. Gas chromatography-mass spectrometry analyses indicated safrol as the main compound of the volatile oil (39%). The results confirm and authenticate the use of its leaves in folk medicine. Furthermore, safrol is economically important as the starting material for hemisynthesis of several products. The antimicrobial activity of the essential oil was studied which showed promising activity against environmental microorganisms as well as anti-inflammatory activity.


Subject(s)
Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Ocotea/chemistry , Anti-Infective Agents/chemistry , Anti-Inflammatory Agents/chemistry , Brazil , Gas Chromatography-Mass Spectrometry , Medicine, Traditional , Oils, Volatile/chemistry , Plant Leaves/chemistry , Plant Oils/chemistry , Safrole/pharmacology
17.
Forensic Sci Int ; 229(1-3): 108-15, 2013 Jun 10.
Article in English | MEDLINE | ID: mdl-23683915

ABSTRACT

Safrole, the main compound in the essential oil of several plants of the Laurel family (Lauraceae), and its secondary product piperonylmethylketone are the predominantly used precursors for the illicit synthesis of 3,4-methylenedioxymethamphetamine (MDMA) which is, in turn, the most common active ingredient in Ecstasy tablets. Analytical methods with adequate capacity to identify links and origin of precursors, such as safrole, provide valuable information for drug-related police intelligence. Authentic sassafras oil samples from police seizures were subjected to comparative analysis based on their chemical profiles obtained by comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry (GC × GC-TOFMS). The enhanced separation power and increased sensitivity of GC × GC allowed for the detection of minor compounds present in the essential oils which were of particular interest in case of very pure samples whose impurity profiles were not very pronounced. Discrimination of such samples was still possible even in the absence of characteristic main compounds.


Subject(s)
Gas Chromatography-Mass Spectrometry/methods , Plant Oils/chemistry , Sassafras/chemistry , Allylbenzene Derivatives , Benzaldehydes/chemistry , Benzodioxoles/chemistry , Benzyl Compounds/chemistry , Cyclohexane Monoterpenes , Dioxolanes/chemistry , Eugenol/analogs & derivatives , Eugenol/chemistry , Forensic Toxicology , Hallucinogens/analysis , Illicit Drugs/analysis , Molecular Structure , Monoterpenes/chemistry , N-Methyl-3,4-methylenedioxyamphetamine/analysis , Phenols/chemistry , Pyrogallol/analogs & derivatives , Pyrogallol/chemistry , Safrole/chemistry
18.
Zhong Yao Cai ; 35(2): 188-94, 2012 Feb.
Article in Chinese | MEDLINE | ID: mdl-22822661

ABSTRACT

OBJECTIVE: To analyze the genetic diversity and the volatile components of Asarum sieboldii from seven habitats in Qin-ba region. METHODS: The genetic diversity of the herb was analyzed by ISSR (inter simple sequence repeat) markers; The relative content volatile components of the herb were dectected by head space solid-phase microextraction gas chromatogrphy-mass spectrometry (HS-SPME-GC-MS). The contents of the 3 main components were analyzed by steam distillation gas chromatography-mass spectrometry (GC-MS). RESULTS: 57 bands were amplified from 7 populations by 6 reliable primers, 51 of which were polymorphic (89.47% of the total). The cluster analysis presented that these resources were divided into two main groups. There were differences in the chemical components and the contents of Asarum sieboldii from the 6 wild habitats. Except for some same components, many unique components were identified in them respectively. In addition, some components could be detected only in some populations which had smaller genetic distance. CONCLUSION: Cluster analysis shows no direct correlation between genetic distance and geographic distance of Asarum sieboldii in Qin-ba region. The accumulations of some volatile components of Asarum sieboldii are possibly related to genetic diversity.


Subject(s)
Asarum/chemistry , Gas Chromatography-Mass Spectrometry/methods , Genetic Variation , Oils, Volatile/analysis , Plants, Medicinal/chemistry , Asarum/classification , Asarum/genetics , Cluster Analysis , Oils, Volatile/chemistry , Plant Roots/chemistry , Plant Stems/chemistry , Plants, Medicinal/classification , Plants, Medicinal/genetics , Quality Control , Reproducibility of Results , Safrole/analysis , Solid Phase Microextraction/methods
19.
J Enzyme Inhib Med Chem ; 27(1): 101-9, 2012 Feb.
Article in English | MEDLINE | ID: mdl-21612374

ABSTRACT

We describe herein the discovery of (E)-N-methyl-N'-((5-nitrofuran-2-yl)methylene)benzo[d]( 1 , 3 ) dioxole-5-carbohydrazide (9e), named LASSBio-1215, as a novel antiplatelet agent belonging to the N-methyl-N-acylhydrazone class, which exert their antiaggregating actions on human and rabbit platelets induced by different agonists, through cyclooxygenase-1 (COX-1) or thromboxane synthase inhibition. This compound was elected after screening of a series of functionalized furyl N-acylhydrazone derivatives, synthesized from natural safrole 10. In vitro assays showed that compound 9e presents platelet-aggregating activity in rabbit platelet-rich plasma (PRP) induced by arachidonic acid (IC(50) = 0.7 µM) and collagen (IC(50) = 4.5 µM). Moreover, LASSBio-1215 also inhibited almost completely the second wave of adenosine diphosphate-induced platelet aggregation in human PRP, and this effect was correlated with their ability to block the production of pro-aggregating autacoid thromboxane A(2).


Subject(s)
Benzodioxoles/pharmacology , Biological Products/pharmacology , Hydrazines/pharmacology , Platelet Aggregation Inhibitors/pharmacology , Safrole/chemistry , Animals , Benzodioxoles/chemical synthesis , Benzodioxoles/chemistry , Biological Products/chemical synthesis , Biological Products/chemistry , Blood Platelets/drug effects , Dose-Response Relationship, Drug , Drug Evaluation, Preclinical , Humans , Hydrazines/chemical synthesis , Hydrazines/chemistry , Molecular Structure , Platelet Aggregation/drug effects , Platelet Aggregation Inhibitors/chemical synthesis , Platelet Aggregation Inhibitors/chemistry , Rabbits , Reference Values
20.
Int J Mol Sci ; 12(11): 7720-31, 2011.
Article in English | MEDLINE | ID: mdl-22174627

ABSTRACT

Chemical composition, antioxidant and antimicrobial activities of the fresh leaves and stems oils of Piper caninum were investigated. A total of forty eight constituents were identified in the leaves (77.9%) and stems (87.0%) oil which were characterized by high proportions of phenylpropanoid, safrole with 17.1% for leaves and 25.5% for stems oil. Antioxidant activities were evaluated by using ß-carotene/linoleic acid bleaching, DPPH radical scavenging and total phenolic content. Stems oil showed the highest inhibitory activity towards lipid peroxidation (114.9 ± 0.9%), compared to BHT (95.5 ± 0.5%), while leaves oil showed significant total phenolic content (27.4 ± 0.5 mg GA/g) equivalent to gallic acid. However, the essential oils showed weak activity towards DPPH free-radical scavenging. Evaluation of antimicrobial activity revealed that both oils exhibited strong activity against all bacteria strains with MIC values in the range 62.5 to 250 µg/mL, but weak activity against fungal strains. These findings suggest that the essential oils can be used as antioxidant and antimicrobial agents for therapeutic, nutraceutical industries and food manufactures.


Subject(s)
Anti-Infective Agents/analysis , Antioxidants/analysis , Oils, Volatile/analysis , Piper/chemistry , Bicyclic Monoterpenes , Bridged Bicyclo Compounds/analysis , Gas Chromatography-Mass Spectrometry , Linoleic Acid/analysis , Lipid Peroxidation/drug effects , Microbial Sensitivity Tests , Monoterpenes/analysis , Phenols/analysis , Plant Extracts/analysis , Plant Leaves/chemistry , Plant Stems/chemistry , Polycyclic Sesquiterpenes , Safrole/analysis , Sesquiterpenes/analysis , Sesquiterpenes, Germacrane/analysis , beta Carotene/analysis
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