Safrole and the Versatility of a Natural Biophore

Lima, Lı́dia Moreira

doi:10.5935/1984-6835.20150023

Cited by 8 publications

(5 citation statements)

References 52 publications

(58 reference statements)

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“…Henceforth, multiple studies on its carcinogenicity and metabolism have been conducted, as recently summarized by Kemprai and colleagues [ 219 ]. According to these authors, the hepatotoxicity of safrole is associated with metabolic bioactivation, leading to the formation of electrophilic metabolites [ 228 , 229 ]. Thus, the carcinogenicity of safrole is believed to be mediated through 1´-hydroxysafrole formation by CYP450 oxidation, followed by sulfonation to an unstable sulfate, which forms DNA adducts [ 230 , 231 ].…”

Section: Essential Oils From Selected Rootsmentioning

confidence: 99%

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Back to the Roots—An Overview of the Chemical Composition and Bioactivity of Selected Root-Essential Oils

Lunz

Stappen

2021

Molecules

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Since ancient times, plant roots have been widely used in traditional medicine for treating various ailments and diseases due to their beneficial effects. A large number of studies have demonstrated that—besides their aromatic properties—their biological activity can often be attributed to volatile constituents. This review provides a comprehensive overview of investigations into the chemical composition of essential oils and volatile components obtained from selected aromatic roots, including Angelica archangelica, Armoracia rusticana, Carlina sp., Chrysopogon zizanioides, Coleus forskohlii, Inula helenium, Sassafras albidum, Saussurea costus, and Valeriana officinalis. Additionally, their most important associated biological impacts are reported, such as anticarcinogenic, antimicrobial, antioxidant, pesticidal, and other miscellaneous properties. Various literature and electronic databases—including PubMed, ScienceDirect, Springer, Scopus, Google Scholar, and Wiley—were screened and data was obtained accordingly. The results indicate the promising properties of root-essential oils and their potential as a source for natural biologically active products for flavor, pharmaceutical, agricultural, and fragrance industries. However, more research is required to further establish the mechanism of action mediating these bioactivities as well as essential oil standardization because the chemical composition often strongly varies depending on external factors.

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Section: Essential Oils From Selected Rootsmentioning

confidence: 99%

“…Based on its strong structural versatility, safrole has remained an important synthon for the synthesis of numerous bioactive molecules through small chemical transformations [ 219 , 229 ]. This includes prostaglandin analogues, non-steroidal anti-inflammatory agents, and antithrombotic compounds [ 249 ].…”

Section: Essential Oils From Selected Rootsmentioning

confidence: 99%

Back to the Roots—An Overview of the Chemical Composition and Bioactivity of Selected Root-Essential Oils

Lunz

Stappen

2021

Molecules

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“…Toxicity of the methylenedioxy group has been associated with the capacity to generate electrophilic intermediates [16]. Methylenedioxy-containing compounds may exert inhibitory effects on cytochrome P450 enzymes (CYP450s) [17].…”

Section: Transmission Electron Microscopy (Tem)mentioning

confidence: 99%

A Triazole Hybrid of Neolignans as a Potential Antileishmanial Agent by Triggering Mitochondrial Dysfunction

et al. 2019

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In the search for new compounds with antileishmanial activity, we synthesized a triazole hybrid analogue of the neolignans grandisin and machilin G (LASQUIM 25), which was previously found highly active against both promastigotes and intracellular amastigote forms of Leishmania amazonensis. In this work, we investigated the leishmanicidal effects of LASQUIM 25 to identify the mechanisms involved in the cell death of L. amazonensis promastigotes. Transmission electron microscopy (TEM) analysis showed marked effects of LASQUIM 25 (IC50 = 7.2 µM) on the morphology of promastigote forms, notably on mitochondria. The direct action of the triazole derivative on the parasite was noticed over time from 2 h to 48 h, and cells displayed several ultrastructural alterations characteristic of apoptotic cells. Also, flow cytometric analysis (FACS) after TMRE staining detected changes in mitochondrial membrane potential after LASQUIM 25 treatment (64.83% labeling versus 83.38% labeling in nontreated cells). On the other hand, FACS after PI staining in 24 h-treatment showed a slight alteration in the integrity of the cell membrane, a necrotic event (16.76% necrotic cells versus 3.19% staining in live parasites). An abnormal secretion of lipids was observed, suggesting an exocytic activity. Another striking finding was the presence of autophagy-related lysosome-like vacuoles, suggesting an autophagic cell death that may arise as consequence of mitochondrial stress. Taken together, these results suggest that LASQUIM 25 leishmanicidal mechanisms involve some degree of mitochondrial dysregulation, already evidenced by the treatment with the IC50 of this compound. This effect may be due to the presence of a methylenedioxy group originated from machilin G, whose toxicity has been associated with the capacity to generate electrophilic intermediates.

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“…Meantime, it could be noted that derivatives 5a and 5d were less toxic than their propyl analogs 5a and 5d . In vivo, the allyl group can lead to toxic metabolic products [24], but it is not always a toxicophore, since this will depend on other structural factors associated with the whole molecule.…”

Section: Biological Evaluationsmentioning

confidence: 99%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b , 5c, and 5d ) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b and 5d ) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization.

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Safrole and the Versatility of a Natural Biophore

Cited by 8 publications

References 52 publications

Back to the Roots—An Overview of the Chemical Composition and Bioactivity of Selected Root-Essential Oils

Back to the Roots—An Overview of the Chemical Composition and Bioactivity of Selected Root-Essential Oils

A Triazole Hybrid of Neolignans as a Potential Antileishmanial Agent by Triggering Mitochondrial Dysfunction

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

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